Chapter One: Prologue to Sissy Slavery
“I said you’ve become the new Sadler School Sissy, Mr. Morgan. Do you know what that means?” My balding Vice-Principal didn’t give me time to answer or think. He continued in his matter-of-fact tone, “It means that over the next three years you will be forcibly feminized for the pleasure of others. You will answer to all commands, and if you do not, you will be punished.”
“Forcibly feminized? Answer to all commands? Is this a joke, do you know who I am!?”
Mr. Wingett finally broke his poker face, giving a wry smile. “I know exactly who you are, the new Sadler School Sissy.” Wingett leaned back in his chair. “Let me explain. As you well know, we are a prestigious, illustrious and exclusive school who offer a path to success to the next generations best and brightest. And to make this possible, we need sluts and slaves. Quite simply put, young men are a raging bag of hormones who spend all their time chasing pussy. So not only do we give our students the very best education, we give them the very best pussy, so they are a hundred per cent focused on their academics. This method has proved highly successful, and I hear similar systems are being installed in schools all over the country.”
“I know all that, Wingett, what about me!?”
“You have become one of Sadler’s slaves, Mr. Morgan. You were offered your scholarship not on your ability at playing football, but on the basis of how you look. Like a sissy. And Sadler always has at least one Sissy Slave on hand.” My jaw almost hit the floor. The reality of what was happening to me had just kicked in. “Your parents only stipulation in the contract selling you to Sadler, other than an exorbitant amount of money, was that your younger sister join the school. They said they still wanted at least one child with a bright and promising future.”
Feelings of anger and hurt pride rolled over me. “I don’t care what they say or you say, I’m getting the fuck out of here!!” I jumped out of my seat and turned to leave Wingett’s office, but he simply continued talking unflustered in his matter-of-fact tone.
“You will recall your mysterious illness last year? While in your coma, the doctors at our Infirmary took the opportunity to insert three devices in to your body. The first was a simple tracking device, much like ones used for household pets. The second device slowly releases a mix of chemicals and female hormones to keep you young and feminine looking. It seems to be working quite nicely.” Wingett gave me a smile another man had never given me, a look that turned my stomach and ran chills up my spine.
The aging, thickly built man then picked up something from below his desk that looked like a garage door opener. “The third is a control device, activated by this. One button will release a drug that will put you unconscious almost instantly. The other button will release a drug that will kill you. I hope you understand this well.”
I nodded my head dumbly and fell back into my seat. I was simply in shock. Wingett leaned over to hit a button on his intercom. “Send her in.”
A beautiful girl, dressed neatly in the school uniform, blue tartan skirt and white blouse, walked confidently into the room. I instantly feel my dick stir, her golden tan, long blonde hair and shapely figure were hard not to stare at. She coughed, and I broke my gaze from her tits to see her looking down at me.
“Hello, Kevin, you can call me Ms. Pascoe. I will be your Mistress, you will follow all my commands from now on. Take off all your clothes.”
“Right now? Here?”
“My instructions were quite clear.”
I turned to Wingett, expecting to see a look of disgust at seeing another man naked, but it was just the opposite.
“Do it over there, Ashleigh, in the light.” He said, pointing to a spot directly in the middle of his well appointed office.
My new mistress grabbed me by the arm, forcing me up out of my chair with surprising strength and shoved me to the middle of the room. “Strip.”
I had lost all confidence. I just looked at my feet that were shuffling nervously.
“If you do not do it, we will do it for you.” With this, she held up an identical device to the device Wingett had still lying on his desk. “And you won’t like how we do it.”
I had no choice. I had seen the horrible things they had done to other disobedient slaves. The thought that that’s what I had become was the worst possible feeling. A lowly, humiliating feeling. I looked up to the see the beautiful woman, her arms crossed under her large breasts, her large blue-green eyes looking sternly down at me, waiting not-so-patiently to respond to her command. My Mistress. I had no choice. I gulped, and began slowly taking off my tee shirt.
“There, that’s a good boy.” Ms. Pascoe cooed.
“Good, almost no musculature. This shouldn’t be too difficult at all.”
“Not a single hair on his chest. We can put it on him right here.”
Red-faced at their inspection and regretting what was to come, I slowly reached down and began untying my shoes. Even in these circumstances, I couldn’t control my eyes from looking up at the long legs of this woman, trying to catch a glimpse of the panties under her short skirt. I don’t know if it was my imagination, but she seemed to adjust her stance so I could see her white cotton panties. I instantly felt the blood rush to my dick.
“This is taking too long. Stand up and put your hands above your head, and do it quickly.” The authority in her voice made me jump to attention, my hands high above my head. I felt so small and stupid. She quickly got to work on the belt of my jeans. She more than incidentally rubbed my cock through the rough material sending waves of pleasure coursing through m body. I knew that she had had a very good feel of my now completely hard cock. She gave a sneaky smile to me as, in one quick motion, she pulled my jeans and boxer shorts down to my ankles, my cock popping out fully erect. “Ooh, Gary, I think he likes it!”
I quickly covered my crotch with my hands in a vain attempt to hide my erect member. Sexy Ms. Pascoe just looked bemused, but there was a genuine look of lust in the eyes of the cankerous Mr. Wingett.
“Did I say to move your hands? Answer me, now.”
Ms. Pascoe gave me a look a mother gives an infant when they’ve been naughty. “No, what?”
“No… Ms. Pascoe.”
“That’s better. Now, step out of those pants around your ankles and move those hands so we can get a good look at you.”
I nervously obeyed her commands, kicking my jeans off and awkwardly holding my hands to my sides as these two looked intently at my pale, shivering body.
“Good, good. I’d say three and a half, maybe four inches. Shouldn’t be a problem.”
Ms. Pascoe stooped in to get a better look. “Pubes aren’t very thick at all. Ever shave down there, honey?”
“No…Ms. Pascoe. I haven’t needed to.”
“That’s an effect of the hormones. This particular specimen has been on anti-aging compounds since Middle School.”
“That might explain this.” She said, touching my erect penis with her index finger, making it swing side-to-side for a moment. “Is this as big as it gets?”
“I think so, Ms. Pascoe.”
“Well, I guess it’s a good thing that you’re becoming a sissy, you never could’ve pleased a woman with that little thing between your legs. Don’t you think so?” The gorgeous girl stared intently at me, waiting for an answer.
I felt an outrage at what had been done to me. What was happening to me over the last few years now make complete sense, like why I hadn’t grown an inch while all my friends have shot up like beanstalks. I was being manipulated in to becoming a sissy and they were ruining my whole life in the process, and now this woman wanted me to nod my head and consent to what they are doing!?
“No, if I hadn’t been on all those drugs, I would have chicks lining up around the block to get into my pants! And when I get out of here and off those fucking drugs, that’s exactly what’s going to happen!”
The bitch looked at me very calmly. “No, what?”
“What?” She suddenly slapped my face so hard it swung my head to the side. I felt a little dizzy from the attack, I could feel the blood rush to my cheek.
“No, what!?” This time, she asked the question much more sternly.
“That’s better. Now, can you please turn around for me?”
I felt like punching this woman and running as fast as I could, butt naked and all. But I know they would just put me in a coma and then punish me for doing it. And I had seen too many punished slaves, and I didn’t want to become one of them. I turned around, still angry, but nervous about what was going to happen.
“Now bend over.”
The words sounded horrible. The fact that I did it was worse. In this moment, I decided every free moment I had was going to be spent to plotting my escape from Sadler and my Sissy slavery.
“You must understand that we are not transforming you into a sissy, but we are in fact, helping you realize that you are a sissy. Understanding this will make this whole process so much easier. Can you spread your cheeks, please?”
My head screamed no, but I felt my hands reach to my backside and spread my cheeks. I waited nervously, listening to footsteps and the shifting of objects coming from the room behind me, feeling more vulnerable than I imagined a person could be. Very quickly, a metal choke chain was looped over my head and around my neck by the strong hands of Wingett. He pulled the chain tight, cutting off my breathing a little, with his hand so high on the chain that is closed fist was resting on my neck. With him pressing down, I had to spread my legs to stop from toppling over. I feel a strong breeze on my asshole, and tears start to well up in my eyes.
“Don’t move.” was all he said.
“I didn’t want to do this until you received your first enema, but I can see by your outburst, urgent action is required.” With that, I hear my mistress spit, and I feel it land roughly near my asshole.
“No…don’t do this…” I gasped.
“Kevin, I live to do this to little girls like you.” She said lustily as I feel a large cold shaft enter my hole and high up into my ass. After the initial shock, my ring started to burn like it was on fire. I squirmed and screamed in pain as my body tried to squeeze the invader back out of me. “Relax those muscles, mister, this thing is going in with or without your help!” Ms. Pascoe said as she gave the shaft another push further up my ass.
“Now Kevin, this is for your own good, you’ll see. Now relax those muscles and I’ll give you a treat.”
Her words were distant and foggy, I couldn’t process them through the extreme pain and humiliation I was feeling as this gorgeous woman shoved a steel dildo up my ass as I spread my cheeks for her. But, for a moment, my body stopped fighting the dildo, and suddenly the entire length popped in past my ring and was held securely in place.
“Aah, there you go. Job done.”
Tears flowed freely, landing in a pool on the hardwood floors. I couldn’t believe this was happening to me, the powerlessness that I felt. Mr. Wingett released his grip on the choke chain, and removed it from my head.
“You may now stand up.” As I obeyed Ms. Pascoe’s command, I felt the huge butt plug up my ass. It was so uncomfortable! “Still hard! I knew you were going to love this!” I looked down to see my dick still standing completely upright. I shuttered with the humiliation, and for the first time the thought that I may indeed be a sissy entered my brain. “Alright, let me give you the lowdown. We call that little plug up your butt The Educator. Any time a Mistress or a Teacher or a Administrator, or whoever wants to teach you a lesson, they can press a little button,” she said, motioning to a black bracelet she was wearing around her wrist, ” this little button will make your little plug give you an electrical shock. It is excruciatingly painful, the butt is such a sensitive area. You would be wise to avoid such lessons.” Her last sentence had a threatening overtone, and I got the message loud and clear. “The plug once activated, as it now is, responds to the body’s temperature. Whenever it is out of you, I will be alerted. If I’m not present, I will instantly put you into a coma where I will come and find you using the tracker and reinsert the Educator. Understand, honey? You can’t take this plug out without my permission.”
I lowered my head, defeated. “Yes, Ms. Pascoe.”
“Good. Now I said I would give you a treat, and as you will work out, I never break my word.”
It was at this point I noticed a bag sitting on Wingett’s desk that had not been there before I was turned around and bent over. Ms. Pascoe reached in pulled out something small and pastel pink. It was a pair of cotton panties. With love hearts on them. I looked at them with a brand new kind of fear.
“Yes, I know, how will you wear a pair of panties without ruining their line with your disgusting little thing there. Well I have a solution.” She again reached into the black bag and pulled out something I had never seen before.
It looked like a corset, but it was made out of a rubber that seemed near identical to flesh. It even had a belly button and the contours of a sexy, young girl. I don’t know if it’d fool anyone at the beach, but under clothes, you would look just like a sexy 16 year old girl. The corset thinned out down the front, eventually becoming a strap made out of the same fleshy material. I struggled to understand the contours on the strap, until it hit me, the strap looked like a pussy. The strap was to hide my balls and make it look like I have a pussy!
“There’s no fucking way- ARGH!!” I fell to the floor as I feel a blinding pain up my ass. Again, tears flowed as I thought I smelt burning flesh and hair and I realized I never, ever wanted to feel that pain ever again.
“Good girls don’t use that kind of language.” She said moving in to stand over me holding the dreaded corset. “Anyway, I wanted you on the floor. Roll over onto your hands and knees.”
I looked up at her, my ass on absolute fire, her white panties in the corner of my eye, but I dare not look at the risk of another shock. Instead, I looked into her eyes. I saw no remorse or sympathy, only a combination of bemusement and sexual desire. I quickly turn away, getting on my hands and knees as quick as I could. I cringe, trying to keep my yelps quiet as the large shaft moving with the shift of position causes my tortured, burnt rectum to scream in pain.
“Good girl.” I heard her move around me so I was again looking at her. She held up the fleshy corset. “This is your Sissy Suit. You will wear it 24 hours a day, 7 days a week. You will not like it. It is designed to reshape your body, giving you womanly curves. Of course, you will probably receive breast implants, and possibly even hip and buttock implants, but this is what will give you a tiny feminine waist.”
I couldn’t believe what she had just said, couldn’t believe what they were planning for me. Who would do this to a person!? I simply nodded, not believing the pain my ass was in.
“Unfortunately, your little cockette is still hard, and I want to make sure the suit is going to fit fine.” She sighed and spat into her hand. “I think someone up there likes you, Sissy.” She said as she stepped back around me.
Despite it all, the hair on the back of my neck stood on end at the thought of this beautiful woman getting me off. I feel her smooth, delicate fingers wrap around my cock and she began to pump. I close my eyes, gasp and orgasm almost instantly. After only three pumps. Ms. Pascoe gives a whole hearted laugh as I look down at the thick white goo lying in a pool in between my knees. I’m not sure if my face is burning red because I just got off or because I was so embarrassed at lasting only a few seconds.
“Alright, you had your fun, now lick it up.” She said in between her laughter, cleaning off her slimy hand in my hair.
“What…” I said dumbly.
“Lick up your goo. You don’t want to leave a mess in Gary’s office, do you?”
Defeated and still on hands and knees, I spin around to position myself over my jizz. I desperately did not want to be shocked again, but the idea of licking up my own semen was absolutely revolting. I look up at her with pleading eyes.
“…please-ARGH!!” My arms buckled under me as pain rang from my ass through my body. My face landed with a splat into the semen. Screams of pain turned to sobs of humiliation as I laid naked, face down in a pool of my own semen, clutching at my ass which felt like it was on fire from a training butt plug.
“You have five seconds to lick it up. Five, four…”
Despite the excruciating pain, I got back on hands and knees and began feverishly licking the semen. The thick salty goo made me gag and spit some back on my chin. I felt it run down the back of my throat in thick globs as I reluctantly licked the seemingly bottomless pool of semen. When I had finished, I looked up at the laughing Ms. Pascoe.
“Honey, look at yourself, your face is covered in cum. Clean yourself up.”
“…how? There are no-“
“With your fingers, babe! Scoop it off and lick them clean.”
I lowered my head and slumped down on my backside, causing a genuine yelp of pain and another laugh from Pascoe. I began using my fingers to clean up the goo from my face, trying to suck my fingers in the most manly way possible. I couldn’t look up at my new masters as I sucked the bitter jizz, tears flowing freely due to the unbelievable pain coming from my rectum.
“Some man you are. Crying, naked, pathetic, licking cum off your own fingers. The perfect sissy. Now stand up, we have to get this suit on before you get another stiffy.” Still feeling great, big smears of cum on my face, I stopped cleaning myself and stood up. “Raise your arms, Sissy, didn’t I just tell you I was putting your Sissy Suit on? You should be excited!”
I just raised my arms and looked down at the floor. She moved behind me, wrapping the fleshy corset around my waist. It didn’t even come to close to fitting, and for a moment, I thought I had had a lucky break thinking they would have to find another suit.
“You’ve probably wondered why the Sadler tailors are so thorough in taking their measurements. Well, it’s for times like these. This should fit perfectly, and for a time too considering your measurements haven’t changed since you were 11. All your measurements, by the looks of it.” She sneered, glancing down to my now limp and unimpressive cock.
Ms. Pascoe retrieved a flesh-toned cord from the bag sitting on Wingett’s desk and began running the cord with a trained hand through the concealed holes in the back of the corset. I was expecting her to pull the corset tight, but she left it quite loose, exposing much of my back. The cord was very long and had two long strands still left over after the corset had been fully strung up. Ms. Pascoe grabbed the strands, and even though she was standing behind me, I could tell she was making a tight knot with them. Then, using a lighter I hadn’t seen, lit the knot on fire for a moment, causing the synthetic material to seal into a ball of cord. She then moved to the other side of the large office, carefully positioning a waist-high stool.
“Now, stand on this.” As I walked cautiously with my legs wide apart to avoid myself more rectal pain, I could hear the swivel of Wingett’s chair as he turned, not wanting to miss a moment of my humiliation. Despite my efforts, stepping up onto the stool caused another yelp of pain and another unimpressed chortle from my Mistress. She looped the now seamless cord through an eye socket installed in the roof with an experienced hand. “Alright, now take a deep breath.”
From the stool, I looked down at my Mistress with fear, dreading what was about to happen. “Take a deep breath sissy!” I suddenly took a deep breath, half obeying my command, half out of fear as I saw her reach for the bracelet around her wrist to activate the Educator.
Pain flooded through my body. As I collapsed for the third time, the looped cord held me up and began tightening the corset dramatically. Suddenly, Ms. Pascoe kicked the stool out from me violently causing me to fall with a thud causing extreme pain in my brutally tortured ass and for the corset to seal up all the way in a very quick and painful manner. I tried to scream, but all I could muster were short little yelps in between short little breaths as the now completely done up corset extremely limited my ability to breathe. I felt like I had been cut in half. I was almost too scared to look at my waist it was causing me so much pain, but when I did, I couldn’t believe how tiny the corset had made my waist. Between my raped ass, and new extremely confining corset, I did not want to move from my slumped, sitting position on the ground, strung up by the cord hanging from the ceiling.
“Okay, stay still, honey.” Ms. Pascoe proceeded to put her knee in my back, making sure the corset was as tight as possible. She cut the looped cord as close as possible and sealed the two ends of the cord trapping me in the Suit with the lighter. The damn thing had been sealed on! There was no way I could take it off! “Aaah, good girl. You can stand up now.”
For a moment I hesitated, the idea of moving and the amount of pain that was going to bring was too much to bear, but I quickly remembered the standard punishment for disobedience. I was learning, just like they wanted me to. As I stood up with the now expected yelps of pain, I realized the corset changed my posture, forcing to have my chest out forward and backside pushed out. It was an incredibly tight squeeze this horrible thing was putting on my body, and I didn’t know how I was going to live with this awful pain.
“Oh, the Sissy Suit makes you look just great!! I love how it makes you look like you’re presenting your ass for everyone’s inspection!” Ms. Pascoe squealed with delight. “Just one or two more things and then we’ll get a mirror and show you the new you! Spread your legs, honey.”
The last command filled me with feelings of disgust, and when I did spread my legs for these demons, I felt waves of shame. Ms. Pascoe moved behind me and I heard her rustling through the black bag, searching for another device to further turn me into a Sissy.
“Now stay very still, this could hurt a pinch.” I took this comment very seriously, considering the amount of pain already inflicted on my naked body. I felt a cool plastic cupping my cock and balls, and looked down just in time to see Ms. Pascoe’s hands in between my legs, clicking the top half of a clear plastic chastity device in place. I cried in pain as the device felt like it was crushing my cock and especially my balls. I looked down at my crotch to see a tiny plastic bubble, resembling the size and shape of a few marbles, where my dick used to be. On closer inspection, I could see how squeezed my cock and balls were in the device, a small hole at the end of the modulated plastic had been made so I could pee, and the head of my penis was trying to squeeze through this small hole adding to the overall discomfort of the horrid device.
“This will help your…thing shrink into a more appropriate size for a Sissy. And when you do get small enough, we’ll move you to a smaller chastity device.”
“Smaller…” I moaned.
“I know, isn’t it great! You’ll eventually get so tiny down there, no cock-lock will ever cause you pain again, no matter how small! You’ll become the Sissy you’ve always wanted to be!” I couldn’t believe what I heard.
The blood rushed from my face and I must of turned a pale white. I was already self-conscious about the size of my dick, and now they were talking about making it miniscule! My life will be ruined! I have to get out of this…somehow.
“Now only one last simple step and we’re finished!” she said as she pulled the strap hanging off the Sissy Suit that looked like a 16 year old girls virgin pussy up between my legs. I shivered as I adjusted my legs to allow Ms. Pascoe to position the long end of the pussy strap between my ass cheeks where it was finally hooked into place with a firm tug at the back of the bodice. This strap was also very tight, firmly pushing my dick upwards into my body in a very uncomfortable manner. I gulp when I realize there is a hole in the strap to allow access to my asshole.
Ms. Pascoe hurriedly stepped in front of me to get a good look at my new Sissy body. She immediately put her hands in front of a huge smile on her face. “Oh my god, he, she’s absolutely perfect! Here, quickly, have a look at yourself in the mirror.” She said opening a large cupboard revealing a full length mirror on the reverse of the door.
I audibly gasped as I saw myself. The first thing I noticed were my red, teary eyes, cum and tear soaked cheeks, and the upright strands of stiff, dried-cum soaked hair. It was shocking to see the perennially happy, confident and good looking face I usually saw in the mirror looking so lowly, humiliated and degraded. But the second thing I noticed was far more shocking. Where my perfectly normal, straight up-and-down male torso had been was replaced by the sexy curves of a sexy, teenage girl. It looked even more realistic than I had imagined, with a belly button and subtle muscle and bone definition and everything! But what looked more realistic than I could of imagined was my…this Suit’s pussy. There was absolutely no hint of my manhood. I dumbly reached for my crotch, feeling only the soft, puffy lips of my…the Suit’s hairless pussy. Other than my flat chest, I had the body of a horny teenage girl!
“It’s great! The pussy strap has custom-made padding to hide your cockette and give the realistic feel of a young, tight snatch! Isn’t it just the best, darling!?” she said, pushing up my shaggy hair, giving it a feminine look. It was scary how my face, with no make-up or a real girls haircut, perfectly suited my new sexy body. I realized why I was chosen to be the Sadler Sissy when I saw what a sexy girl I had become. The thought turned my stomach. What a sexy girl I had become…
“Yes, Ms. Pascoe” I said dully, remembering my lesson about answering questions quickly and in a manner she liked.
“Oh! I almost forgot!”
She dashed off out of sight. I couldn’t take my eyes off the image of the scared, flat -chested, naked girl in the mirror.
“Here, raise your foot for a sec, hon.” I was awoken out of my trance to see Ms. Pascoe at my feet holding the pastel pink panties. I felt tears welling up as I raised one foot and then another. Ms. Pascoe pulled the panties up my legs, firmly tugging the panties between the cheeks of my ass. I turned to see the panties were very high cut, revealing the lower half of my cheeks. It was only now that I realized that with the Suit changing my posture so I was permanently sticking my ass out and my waist looking tiny, it now appeared I had a very feminine, rounded ass that was perfectly framed by the sexy panties. I felt sick as I realized I had a girl’s incredibly tight, sexy ass. As I turned front on, I immediately heard Ms Pascoe’s laughter. I quickly worked out why. I had a clear and distinct camel toe. “Wow, these Sissy Suit’s have really come a long way , haven’t they Gary?”
Wingett merely grunted in response, and it was only now that I realized he had been jerking off to my humiliation. Knowing it was my degradation that got this man off sent waves of fear through my body. I turned back to the mirror red-faced in shame. I noticed the panties completely hid any sign of the lower edge of the suit, and when I saw Ms. Pascoe reappear in the mirror holding a thirteen year olds training bra, I knew the upper edge was soon going to be hidden as well.
“For the moment, it has been decided your sissification will be kept secret. As a result, you won’t have your large, bouncing breasts just yet, but I’d hate for you to leave this room not feeling like a complete sissy, so this special training bra has been arranged. Raise your hands!” I reluctantly obeyed the command so she could put the training bra over my head and around my chest. “You’ll notice the sewn-in inserts, they’re to give you just a hint of boob and feminine nipples. I’m sure no will notice. The inserts are special because they release a mixture of hormones and chemicals directly into the skin, so you’ll soon have your own jiggling, sensitive bosom in no time!”
I release a low groan on hearing this. My own set of tits, to match my sexy hips and ass. This is a nightmare come true. Looking at myself, my white training bra with the same pink love hearts as my pink panties, my new cute nipples poking through slightly, my tiny waist giving the impression of wide, feminine hips, sexy naval, an all-too-obvious camel toe, and to top it off, one of the sexiest asses I had ever seen; I had to accept the fact that I had a body that looked like a smoking hot teenage girl. I broke down in tears. At this, I heard a guttural moan coming from Wingett. I turned and couldn’t but notice the jizz splayed all over the table.
“Perfect, just in time!” Ms. Pascoe said as she put my arm in hers and scurried to the desk. I let out a long, exhausted moan as pain screamed from my cock and ass with the quick movement in the new, confining suit. “Lick Mr. Wingett clean, fix up his pants and get your tongue to work on this desk.”
I stood dumbfounded by my latest command. I looked at this old, ugly man and his slimy, shrinking dick with his shaggy salt and pepper pubes and felt like vomiting. I had endured so much humiliation already, but this was so much worse. I could never get myself to suck this man’s dick. But the pain ringing out of my waist, balls and especially my ass, and knowing that disobedience would bring so much more pain, as well as more severe humiliation, I knew this was no time to fight. I slowly and reluctantly lowered myself on to my knees between the legs of Wingett. Up close, the dripping penis looked disgusting and smelt worse and as I leaned in, trying to ignoring the incessant giggling of my Mistress, I gagged on the horrible smell.
“…please…” as I muttered the one word, I saw Ms. Pascoe reaching to the her bracelet to give me another horrible shock. I instantly opened my mouth and put my tongue on the tip of Wingett’s penis and began licking off his juices.
“That’s good Sissy, you’re learning quickly.”
I slowly and surely began licking the flaccid dick clean, trying desperately not to breathe in the musty smell or picture what I was doing. I hated how the old man’s pubes tickled my nose and got into my mouth. I hated how the salty taste of his cum hung in my mouth, reminding me constantly what I was in the process of doing. I hated how I was praying that this man’s dick didn’t get hard while I had it in my mouth. What had I become?
“Well done, Sissy! Your first taste of a man’s dick! I know you’ll never forget it!” For once, I think we agree. “Now button him up, and clean this desk.”
I hesitated a moment, briefly looking up at Wingett from his crotch. Totally content, totally in control, I saw no sympathy in his eyes. From my position at his feet, I felt like a possession of this man, something not so far from the truth. I awkwardly put the man’s soft dick back in his boxer shorts, trying to touch it as little and lightly as possible. I felt disgusting.
I got on my feet and gulped when I saw how much cum had been spread across the table. I looked up to see Ms. Pascoe’s arms crossed, framing her large breasts, tapping her foot impatiently with a stern look on her face. The Educator had taught me well to not keep this woman waiting. I hesitantly bent over to lick the semen, closing my eyes, trying to imagine that I was somewhere else, doing something else. The reality hit home as the think, salty goo entered my mouth and slid down the back of my throat.
I now realized I had bent over directly in front of Wingett, and he now began kneading my ass cheeks. “…oh yeah, what a great ass…” I heard him gasp under his breath, as I cringe as he lightly plays with my ass, gently fingering my tortured asshole. I could not believe the depravity I was being subjected to!
As I continue to lick, and moan every time Wingett touches my hole, Ms. Pascoe moves in front of me and begins speaking as if reciting a memorized speech. “Kevin, consider tonight your birth in to a new life. You are a slave, and you are a sissy. You are a possession whose sole purpose is to pleasure others. To do with as others please. If you do not please us, if you do not do what you are told, you will be thrown away as a malfunctioning possession should be.” Tears began welling up, as I continued gulping down the warm cum, as my horrible fate was being spelled out for me. “You will be a sissy slave. You will go to every measure to dress like a girl, look like a girl, act like a teenage girl. You will be humiliated and degraded for the pleasure of others. You will become something inferior to an average person or the average slave.” Tears flowed from my eyes as I tried to focus on licking up the cum and not the nightmare being described to me.
She started again in a more relaxed tone of voice. “For now, your sissification will be kept a secret. You are not quite yet ready to handle the responsibilities of the Sadler School Sissy. That means you can wear your ugly boy clothes in public. But you must always wear your panties and bra. The other Sadler mistresses will know this and they will personally inspect you to confirm this. If you are not wearing them, the Educator will punish you. You will be moved to another room and have a new roommate who is also in slavery. This will give us greater freedom to continue your Sissy training. And the last piece of house business, you must be at the showers at Building J every morning at 8am. Understand the rules, Kevvy?”
“Yeth, ooowww, yeth, Mth. Pathcoe.” I said, not wanting to stop cleaning the desk with my tongue, Wingett now inserting two fingers up my asshole.
“Good, now that desk was clean long ago, so when Gary’s finished having his fun, get dressed and return to your old room for one last night. We’ll move you tomorrow.”
“I’m just playing around, just get him to lick my fingers clean and get him out of here.”
“You heard him, Sissy, suck those fingers!”
I lowered my head defeated and turned to suck my ass juices of this cankerous, old man’s fingers. I began to stoop down when he said, “No.” I stopped, and he shifted me so I was now sitting in his lap. “Now open your mouth.” I opened up dumbly, and he put the entire length of his smelly, disgusting fingers in my mouth. “Suck, bitch.” I could hear Ms. Pascoe laugh whole-heartedly, and I felt Wingett’s dick stir under my ass as I sat in bra and panties sucking my ass juices off this man’s fingers like they were a cock. “Alright, that’s enough. Get out of here, I’ve got work to do.”
I hopped out of the man’s lap and, as quick as I could with my restrained waist and balls and my tortured ass, I moved to my clothes and got dressed. I was never so relieved to put on a pair of pants. When I finished dressing, all they lay on the ground were my boxer shorts.
“Here, I’ll take that. You’ll never wear boxer shorts again, mister.” Ms. Pascoe said, throwing them into the fireplace. “Now, I’ll see you at 8am tomorrow, understand?”
“Yes, Ms. Pascoe.”
As I, head down, began walking out of the room, I caught a glance of myself in the mirror. Feminine, cum and tear soaked face, with budding breasts and wide curves that my thin t-shirt did little to hide, I looked how I felt. A Sissy Slave.
Chapter 2: Slaves, Sluts & Showers
I stood in the empty hallway in front of the showers of Building J, nervously looking at the double-doors, my eyes still red from this morning’s crying session, my torso aching in its tight corset, my poor butt still ringing in pain from yesterday’s torture in Wingett’s office. I just don’t know if I can take this sudden change in my life. Usually this was a ‘Girls-Only’ dorm, but the Admin seemed to recognize why I was there and I had no problem freely walking around the halls, regardless of my thick, baggy boy clothes and shaggy, boys haircut. And now I was here, standing in front of the showers, listening to the giggling of girls coming from within, too terrified to take one more step closer.
“Ah, Kevvy, right on time!” I spin around to see the sexy Ms. Pascoe proudly trotting down the hall in a too-short pink terry-cloth robe that revealed a deep cleavage, holding a big cup of coffee. “I was afraid you might not show and I’d be forced to punish you, maybe even drag you down here naked in front of the whole School. It’s very common for new slaves; but here you are, keen as mustard!” With this, she gives me a congratulatory pat on the head. “But look at your terrible outfit! Tsk tsk. I cannot wait till I get to dress you myself, you silly little boy. Well, we better get to it, but first, let’s see if you are still wearing my little additions to your outfit.”
She gives me a playful wink as she snakes her free hand into my jeans and snaps the elastic of my pink panties, making me flinch a little, my corset offering surprising little protection. “Good girl!” The sexy Ms. Pascoe leans over me, suddenly grabbing my chest, rubbing her thumb over my little inserts’ nipples. “Very good girl!”
I just stand dumbly in front of her, part from shock, part from fear, letting her probe my body, trying to ignore the footsteps I hear echo around the hallway and my cheeks burning red from embarrassment.
“Well, what are you waiting for, Kevin, time to get in the showers!” Ms. Pascoe said just a little too loudly, spanking my ass to get me moving in the general direction of the Girls Showers. The hand-spank over my jeans wasn’t too bad, but as it shifted the butt plug inside my tortured ass, I cringe in pain. “Heh, you really are a big baby, aren’t you? Born sissy, I guess. Don’t you think so?”
My cheeks burn even more, from anger and embarrassment, but I know what she wants to hear. “Yes, Mistress, of course.” I mutter as I shuffle in to the showers, gulping as I open the door and I hear the girls chattering get distinctly louder.
“Hurry up, Sissy!” Ms. Pascoe commands loudly as she pushes me into the Showers’ Changing Rooms. I wince in pain with the sudden movement in the very constrictive Sissy Suit. I look up to see three gorgeous girls, all who have abruptly stopped talking to stare at me, all half-dressed in lingerie and short, tight-fitting outfits, all attempting to cover themselves as they look down at me with quizzical faces. “Sissy, say hello to Caitlin, Ellie and Liz. Girls, say hello to the newest Sadler School Sissy.”
All three suddenly burst out in high-pitched laughter. “Oh, you poor little thing!”
“Yeah, you’re right, I remember this one, he is a little thing!” All four of the girls break out in another round of laughter, as they relax and uncover their sexy bodies, obviously not fussed about a Sissy seeing them get dressed.
“Hello.” I mutter, wishing the ground would open up and swallow me whole.
I had seen these girls before. These were some of the Sadler Sluts, super-sexy girls who were paid to service the people who attended and worked at Sadler. As a member of the Junior Soccer Team, I was lucky enough to have earned a session from one of the Sluts, who happened to be the gorgeous Italian girl, Ellie. Her dark hair, perfect olive skin, and her gorgeous large breasts made her impossible to forget.
“Oh yeah, this one was impossible to forget. No hair, no muscle, hardly any cock at all. It was like fucking a twelve year old. No wonder they chose you to be Sissy.” Ellie said snidely as she continued to slip the tight, black mini-dress up her legs and over her curvy figure. As I stare at her unbelievable body, her breasts straining against the tight, strapless bra, I felt my dick get hard, and then instantly the pain as my dick began crushing itself in its tiny chastity cage.
“Why is he making those silly faces?” Caitlin asked innocently, covering up her breasts and pale, puffy nipples with her crisp, lacy, bright pink bra and hooking it up at the back as my cock tried to break itself out of its tiny chastity cage, making my eyes water, as it felt like my dick was crushing itself.
“I think you hot-as-hell girls might be making poor Sissy’s little cockette hard. You see- hmm, It might be easier if I just show you. Kevin, take off your jeans.”
I gasped when I heard the command and I forced myself to remember the incredible pain that came with any sort of disobedience or delay. “I have to get out of this, somehow’ was the thought running through my brain as I unbuckled my belt and dropped my jeans to the floor. I looked up to see the Sadler Sluts pointing and laughing at my cute cotton panties and I quickly lowered my head back down, cheeks flaming red.
“Oh, how cute! They remind me of my little sisters panties!” Said Caitlin, bending over, revealing her full and shapely ass, to slip her white stockings up her legs, pausing briefly to move her long blonde hair out of her face. I wince in pain again, making me grab at my crotch whimpering a little, as I feel my hardening cock strain against its cage.
“Well, they remind me of the panties I used to wear when I was six! Perfect for a sissy!” Ellie said between her laughter. “Although, I have to admit, she looks damn sexy in them!” She said, forcibly spinning me around so the girls could get a look at my ass in the high-cut panties that left the bottom half of my cheeks on display.
“Wow! Great ass! I think the guys are going to love you!” Said Liz as she slipped a slutty tube top over her bare chest, completing her outfit of stockings, a mini skirt that could be mistaken for a belt, and red high heels. She looks like an ebony goddess in her very revealing outfit, her beautiful body completely on display, her long black hair shimmering in the light. I bend over in pain as my dick gets harder.
“I still don’t get it, what’s he doing?” asked Caitlin, carefully positioning her garter belt.
“Alright, alright, I’ll show you. Kevin, lose the panties. In fact, take off everything except your bra.”
Waves of degradation and humiliation rolled over me. I felt so small and stupid being belittled by all these stupid whores, forced to strip in front of them for their pleasure. But I guess this is the life of a Sissy Slave. ‘My life now’, I thought as I tried to blink away my tears. “I have to get out of this, somehow.’ I step out of my shoes and jeans around my ankles and I slip my heavy sweater and tee shirt over my head revealing my wide feminine curves and training bra, with its synthetic little breasts and perky nipples. I stand there, shivering in the cold air, awkwardly holding my hands to my side as these girls inspect my tortured body.
“Oh my god! He does look like a twelve year old! The perfect twelve year old girl!” cried Ellie when she saw the cutesy training bra, covered with the same little hearts as my cotton panties.
“Well, he’ll be becoming a woman soon enough, trust me.” Ms. Pascoe added with just a hint of menace in her voice.
My ego was almost completely shattered, comparing my eighteen year old male body with a twelve year old girls was too much! And what really stung was that I realized the truth in the comparison. And they hadn’t even seen the worst part.
“I don’t know, with those wide hips and sexy, toned stomach, he looks more like a flat-chested 16 year old. It’s just the cutesy bra and panties that make him look prepubescent. How’d you give him the curves, Ash?”
“They call them Sissy Suits. Essentially it’s a very thin, very strong corset made of a rubber that looks identical to human flesh. It even has pores and the shape of a toned female body! It really is amazing!” Ms. Pascoe announces proudly, looking over her Sissy prize. “Kevvy doesn’t like it much. It is very constricting and he has to wear it almost 24/7 so that his body will reshape, giving him a sexy feminine waist forever. Now enough dilly-dallying, Kevin, take off the panties!”
After being hit by another wave of humiliation, I obediently slip off the panties, revealing my pink, bald, cute pussy to a wall of laugher. This was the worst part. I feel my cheeks burning red with embarrassment.
“Aww, how cute!”
“Oh my God, Ash, what did you did with his little dick!?” Liz squealed. “I thought you said she was a sissy!”
Ms. Pascoe just smiled as she unhooked the strap at the back of the bodice of my corset, moving my fake pussy out and tucking it out of the way under the bodice, revealing my cock locked away in its miniscule, clear plastic cage. To my surprise, there was no laughter, only shocked faces with hands covering their wide open mouths as I feel the cool morning air touch my sensitive, trapped cock. Maybe this was the worst part.
“How is that even possible!?”
“Oh my god, you’ve made him like a toddler down there!”
“Now I can explain why he was making all those faces. It was because you gorgeous girls were making his little dickie hard, which must be very uncomfortable for poor little Sissy.” said Ms. Pascoe as she traced a finger around the base of the chastity cage, caressing my sensitive skin, laughing as she does it.
I buckle over, groaning from pain and lust, as my cock continued to strain against the chastity device, my legs barely holding me up as she tickles my balls with her fingernails. I don’t know if I am going to faint from pain or cum as the three Sluts just watch with stunned faces.
“Oh, Ashleigh, you’re hurting him!” cried Caitlin, with sympathetic eyes, as she slipped her pink micro- miniskirt up her legs, making Ms. Pascoe finally stop her fondling, making me gasp in relief.
“We could butt fuck him until he squirts, make him soft that way. Would that make you feel better?” Ellie cheerfully suggests, although it is a suggestion that sends shivers down my spine, especially when I see Ms. Pascoe seriously considering it.
“The whole idea is to hurt him, you guys, he’s a Sissy Slave!” Liz says, looking away from her little handheld make-up mirror only for a moment as she applies the finishing touches to her exquisite face. “They are the lowest kind of slave, the lowest kind of person, and Ashleigh has the responsibility to teach him that.”
“Oh…” says Caitlin, looking over my naked body, other than my training bra, pink panties scrunched up at my ankles and a near-invisible chastity lock. My whole body blushes red as I see her wide blue eyes soak in my utter humiliation and exposed flesh.
“That’s not quite right, Liz. It is all our responsibility to teach Kevin his new place in life.” Ms. Pascoe informs the group of girls. “I’m about to get Kevin here ready for his first day of service, and may be it would teach you girls something by watching him, maybe even helping him.” she says, patting my naked butt cheek.
“Oh, I don’t know if I want to do that, Ashleigh…” said Caitlin with wide, sympathetic eyes as she buttoned up her near-transparent white blouse, leaving her bright pink bra on display.
“That’s okay, Caitlin, it’s alright if you don’t want to help. How about you girls?”
I lower my head as I hear the girls enthusiastically volunteer to assist in my torture. But, at the very least, Caitlin has shown some kind of remorse for what was happening to me. Everyone else thought it was totally natural to turn me into their helpless girly play-thing, just like Liz and Ellie were going to do right now, but Caitlin seems to care. Maybe she would, could, help me somehow. She gives me one last sympathetic look with her wide blue eyes as she walks out of the changing room, leaving me surrounded by the three gorgeous girls towering over me, naked, shivering and alone.
“Now, as you may have guessed, Kevvy, it takes a lot of work to turn a dirty old boy into a gorgeous girl, like Liz and El here.” Ms. Pascoe continued as she lowered herself to my feet and took the panties from around my ankles. “Now here at Sadler, we just don’t put make-up on you, glue a wig in place, stick you in a dress and shove you out the door. No, you will need to undertake a strict regime of training and medical treatment if you want to become a really desirable, really sexy female. That is what you want, isn’t it Kevin?”
“Yes, Ms. Pascoe.” I mutter, my face red, trying to ignore the smirking faces of the two remaining Sadler Sluts.
“I’m glad you said that, because this is a very serious commitment.” She says, looking at me as she folds my clothes neatly and placing them in an open locker. She retrieves a few items from the locker before closing the door, revealing that it has ‘Sissy’ written on a piece of tape stuck on it, indicating that this is my locker.
“Won’t you need my b-bra, Mistress.” I stammer out.
“Firstly, you wear a training bra, honey. And no, we will need it to replace the inserts. Mr. Wingett wants you to have a set of very big, natural, bouncing breasts with very sensitive nipples. That means we will have to replace the inserts daily so that you get the proper hormonal treatment.”
“Wh-” I bite my tongue. I know the slightest disobedience will result in the triggering off of the Educator, and the last thing I want to do is become a crying, sniveling ball on the ground, desperately clutching at my ass in front of these three girls.
“What was that, sweetie?”
“Wh- wh- when do you think I will get my breasts?”
Ms. Pascoe smirks, seeing my growing obedience, while Ellie and Liz just full out laugh. “It will be a gradual process over years, but I expect your chest will start budding tiny breasts and perky nipples within the week, babe. Isn’t that exciting?”
Oh God, I wish I hadn’t asked. “Yes, Mistress.”
Ms. Pascoe laughs at my answer. “Good girl. Now, enough chit-chat, it’s time to introduce you to your new daily routine. I think you’re really going to like it.”
With this she takes me by the hand and starts leading me to the showers, naked other than a cutesy training bra and a tiny, almost invisible, chastity cage. My body can’t help but struggle a little, and I cover up my crotch with my free hand.
“Now, none of that” says Ellie from behind me, giving me a firm spank on my naked ass that makes me jump, leaving a stinging red mark on my butt cheek. “Be a good girl and follow Ash- I mean, Ms. Pascoe’s instructions or we will make this very embarrassing for you.” With that, she takes the hand covering my manhood, although it seems more like boy-hood, and begins leading me by the hand as well.
Now I am walking in to the Girls Showers, naked other than a training bra and chastity cage, both my hands being held by two sexy girls towering over me. I’m beginning to feel like what they want me to feel- like a hopeless sissy.
I am relieved when I see the showers have stalls, but less relieved when, as I pass by, I see all the girls stop and stare at me, and my crotch, from behind the stalls sporting shocked and bemused expressions.
“Relax, honey, this shower is for us, these are some of the other Sadler Sluts and Mistresses. Your, heh, little secret is safe with them.” Ms. Pascoe’s comments did not save me from the sheer humiliation of being marched down a hall with my hands being held, my tiny cock on full display.
I notice at the end of the long line of stalls there is a more open area, with showers tracing the walls, with a collection of benches in the middle of the room. As I am led closer I notice this area is filled with gorgeous women. The girls who grab my attention first are the naked ones, who wear only thick leather collars and cuffs around their necks, ankles and wrists and a black ball gag in their mouths. Most have their hands locked around the shower head while they are inspected and scrubbed down by nurses wearing sexy, pink latex outfits. I notice two slaves who are washing themselves, but have stainless steel chastity devices running around their waist and in between their legs. None of the girls look happy. I begin squirming as I again begin to get hard, crushing my dick and balls in their tiny chastity cage.
“And these are the famous Sadler Slaves.” Ms. Pascoe announces, motioning to the slaves with her free arm, ignoring my squirming. “These girls do all the horrible, disgusting things that someone would simply not volunteer for but our School body demands. Take Renee over here, she is a slave to a sadist. She’s been branded four times! Not to mention countless other cruelties.” I hear Renee whimper behind her gag as Ms. Pascoe runs a hand over the welts on her backside and the branding reading ‘Fuck Slave’. “And take Jessica here, she’s about to have an operation that will leave her with no bladder control at all. She’ll have to wear pull-ups every moment of every day for the rest of her life!” Jessica begins struggling against her bondage and lets out a muffled sob from behind her gag after she hears this comment. “Oh, did I ruin the surprise? I’m sorry.” Ms. Pascoe says laughing to herself. I shivered at the cruelty being inflicted on these girls. “And now, I’m afraid, you have become one of the Sadler Slaves, Kevvy.” With this, she and Ellie hold out my hands. A gorgeous Latino nurse with large breasts and full lips steps in front of me and promptly clicks pink leather cuffs around my wrists.
“Just gonna take a wild guess and say this is the new Sadler Sissy.”
Chapter 3: The Morning Ritual
The beautiful, caramel skinned nurse says through her wide grin, her eyes transfixed on my locked-up cock. Her dark wavy hair, big brown eyes, large natural breasts and sexy, round ass makes my cock harden and makes my face cringe in pain.”I’m Rebecca, I’ll be his Nurse. Girls, you can call me Becky,” and turning to me and pointing a finger in my face, and suddenly wearing a stern expression on her face “And you, you can call me Nurse Rebecca. Got it?”
“Yes, ma’am.” I mutter.
“This one doesn’t learn very fast, does it?” With that, she casually reaches to her wrist and hits a button on her bracelet. A tremendous electric shock radiates in my ass, sending waves of pain through me. I yell and cry out and my knees fall out from underneath me, but Ms. Pascoe and Ellie hold me up easily. I am crying in pain now, sobbing, and Nurse Rebecca has no trouble at all forcing my mouth open with her hands and putting a black ball gag in my mouth, pulling its straps very tightly, and locking it shut at the back of my head. My sobs become muffled murmurs. I look up through tears eyes, trying to find some sympathy in the four women witnessing my torture, but all I see is bemused and lustful looks. I even see Liz pinching her nipples through the thin material of her tube top, her face flustered with sexual arousal.
“There, that’s better. I think it’s important to establish authority with the Slaves. That way they know to respect you.” Rebecca says, tugging harshly at the straps of my gag, making sure it was on me as tight as possible as I let out muffled whimpers from behind it. “Now, I told you to call me Nurse Rebecca, didn’t I? Not ma’am, not Mistress, Nurse Rebecca! Got it!?” She says, cruelly slapping my face. I simply nod dumbly, scared out of my wits by this woman. “Good. Well, let me take this opportunity to introduce the new start to your daily routine. I want you to consider this just like the first cup of coffee in the morning- this is just part of your morning ritual. You will be here promptly at eight o’clock, every morning. Understand?” I nod my head dumbly. “Good, because I have other slaves to look after and I have a tight schedule. Tardiness will not be accepted and you will be punished for it severely. Understand?” I nod my head dumbly, still sniveling from my shock by the Educator.”Good. Now, it is my job to keep you clean and presentable and making sure you are healthy and on track with your…change. If I see you are breaking rules, or simply that you’re not on track with your change, you will be severely punished. understand?” I just nod my head, scared out of my mind. “Good, I see there is not much fight in you, that will help you a lot.”
The tall, curvy nurse drags me across the shower area, my tortured ass screaming in pain with the movement, and lifts my arms, slipping my training bra up over my head and locking my two cuffs over the shower head in front of the door to the Open area of the showers. I am hung up and exposed to the whole corridor! Next, she puts more tight straps around my ankles, tugs my feet back and locks them into eye sockets on the ground, leaving my feet more than a metre from the wall. The bondage leaves me stretched out on a near 45 degree angle, my legs spread wide apart, and I have to stand on my tippy-toes to relieve the incredible pressure on my wrists. It is extremely uncomfortable, and leaves me stretched out, my shivering naked body completely exposed to everyone in the Showers. And when I feel the cool morning air against my cock and ass, I know that the most private, sensitive parts of my body have been made completely accessible by these maniacs.
“Hmm, we’re not used to having Slaves as short as you. You must be not much more than 5 foot tall. That looks painful, Sissy.” I just nod my head mournfully as pain racks my body.”Well, I guess that’s fine for you, though, isn’t it? Well, isn’t it, Sissy?” she says, giving my defenseless ass a firm spank. I just nod my head dumbly, cringing as my plug is shifted in my aching ass, my thoughts being fogged through the incredible pain. I hear some shuffling from behind me and then some giggling. I see Ms. Pascoe step in front of me.
“You may have been wondering how are meant to go Number Two’s when you are supposed to have the Educator in you all the time. Well, here is the answer-” Ms. Pascoe motions to one of the girls behind me and I feel soft fingers crawling over my ass cheeks, spreading my cheeks as another set of fingers begin lightly probing my sphincter. I immediately begin squirming and squealing behind my tight gag. “You see, we have to lock you in bondage every time we take the Educator out. You know, just to be safe”. Ms. Pascoe says rubbing my naked, smooth butt. The fingers finally penetrate my hole and remove the large butt plug that has been in me since yesterday, stretching my hole out horribly for a moment as it is roughly tugged out. For a second, I feel strangely empty, like my ass is missing the butt plug, before the stinging of my tortured asshole takes over and I begin squealing again.
Ellie begins laughing. “What a little girl. This plug is tiny!”
“This little undeveloped boy will feel more than enough of that plug.” Ms. Pascoe informs the girls as I continue letting out muffled moans from behind my gag. ” Besides, you wouldn’t want him stretched out before Wingett takes his virginity. After that, we’ll move on to bigger plugs so we can train his ass to take any cock in the school.”
The girls all begin giggling at this, while I feel fresh tears come to my eyes as I see a horrible glimpse of my future as the new Sadler Sissy.
“Lube or no lube?” I hear Nurse Rebecca ask from behind me.
“Do you think he deserves the lube?”
“It’s a Sissy and a Slave. What do you think?”
With that, I feel plastic pushing at my sore, tortured asshole, and finally inserted past my sphincter by feminine fingers. I can’t help but wince and squirm. “Now, relax these muscles, Sissy, I’m going to inflate the stopper.” I didn’t know what Nurse Rebecca was talking about when she said stopper, but I knew inflating something inside me was going to be sheer hell. I turn to see the Latino woman begin to pump a small bag, and I feel the stopper in my ass inflate up rapidly. I begin squirming and squealing again, but the pumping does not stop and I fight on my bonds even more.
“Be careful, he might explode.” Ellie chirps in, laughing at my squirming.
“The secret to looking after any Slave is no sympathy. They have to be constantly reminded that they are completely under control, completely under our thumbs. I find the stopper does a good job of that. Sissy, do you want me to stop pumping the stopper?”
I nod my head frantically, tears rolling down my cheeks. “Aww, too bad.” She says with a sinister tone, giving a few more hard pumps. “See, this Slave is under the mistaken impression that it still has some say in what happens to it. I can fix that.” She says, giving a final few pumps before finally stop pumping up the inflatable stopper. It feels like I am going to explode. “Okay, let it flow.”
My body tenses as I feel lukewarm water enter past the stopper. After a moment, it soon begins to sting my insides. After a few more seconds, the water is beginning to burn my insides and I resume my futile struggling against my bonds.
“Oh, the burning. I totally forgot. This is a typical Slave’s enema. We add plenty of soap and disinfectant to the water to make sure they are nice and clean. Although, it does make it awfully uncomfortable for the Slaves. But who really cares about that?” Nurse Rebecca informs me from somewhere behind me, as the amount of water entering me starts to get painful. “Don’t worry, you’ve just made the halfway mark!”
I whimper from behind my gag, the combined pain of the stopper, the tight Sissy Suit, the amount of water being pumped into me and the burning from the disinfectant is too much, and I begin to feel my stomach cramp, my muscles clamping together in a very painful way.
“What’s he doing with his stomach?”
“It’s cramping, Ellie. this is normal for a Slave receiving their first enema. It’s okay, it’ll get used to it” Nurse Rebecca said in a matter-of-fact tone like I wasn’t even there. I squeal and whimper from behind my gag, and I struggle against my bonds with everything I’ve got as the pain gets past the point of bearable, my stomach cramping horribly. I see some of the girls from down the hall crane their neck to see what the commotion is all about. I feel a firm swat on my butt. “Stop fussing, Sissy, you’re almost done!” I let out another long, muffled whimper and look at my nurse with teary eyes, trying to elicit some compassion, but I see her eyes focused on a plastic bag with a rubber tube running to my butt. “There…you…go- all done! Now, just hold that for 5 minutes and you’ll be all done with your little butt cleaning!” I let out another squeal from behind my gag, but I am simply too exhausted from pain to continue to fight and struggle against my bonds futilely, even though I really want to.
“Ms. Pascoe, I believe you have something to say at this point?”
“Thank you, Becky. And let me just say, it is a pleasure to watch you work.”
“Thank you, that’s an honour coming from a Mistress with your reputation.”
Ms. Pascoe just smiles at the compliment. “Now, I just want to tell Sissy here what we will be doing today and for a few years to come. We are feminizing you, Sissy, and we aim to do a good job. Some of the key differences between the appearance of men and women is bone structure, especially in the shoulders and the jaw-line. Obviously we don’t have a problem with you there, it’s the very reason you were picked in the first place. You look as fragile a girl I have ever seen.” She says, running a delicate finger along my soft, tear-soaked face. “Another difference is breasts and hips, but you know we are working on that.” she says, running her hand along my naked butt cheek. “No, why we are here is because of the next key difference- skin. Men typically have much courser skin than females. What we want with you is to have such soft, smooth, supple skin that no one will ever think that you are, were, a man. We want to take you beyond even the normal softness of female skin, we want to give you the soft, sensitive skin of a newborn baby! Your hormonal implants and the chemical concoction we have on the inside of your Sissy Suit and training bra helps, but we still need to apply another special lotion everyday to every inch of your body, directly to your skin. We call it Sissy Sauce, It will keep you hairless, smooth, soft, and will also act as a strong perfume. It’s a beautiful rich Vanilla smell! You’re going to love it!” I simply give another long moan, part from the new torture revealed to me and part because another painful cramp hits my stomach.
“Alright, that should be enough.” After what seems like hours, Nurse Rebecca finally decides it’s time to take the burning water out of me. I hear her fiddle around with something behind me, then a slight hissing. I feel the stopper start to deflate and I breathe a huge muffled sigh. But instead of the stopper being taken out, I feel something round and plastic being pressed against my hole. My stomach muscles are begging for release and my ring is on fire because of the amount of torture it has had to suffer in the last twenty-four hours and I moan when I think something else is about to enter my ass. Up until yesterday, my asshole was untouched, sacred ground, now it seems its these girls playground. The round, unlubed plastic object is roughly forced up my hole, making me squeal in pain. I then feel the stopper roughly pulled out of me, but slips out very easily due to what must be a short tube holding my sphincter open, as now the water is gushing out of me with me being in no control whatsoever. They have even worked out a way for me to shit without me having any say in it! But I have to admit, it feels like heaven for a moment as the tremendous pressure on my stomach has finally been relieved. The shame comes rushing back when I hear the water and my own feces drop at my feet with a splutter, landing roughly near the large, open drain also at me feet.
“Eww, gross!” cries Ellie when she sees the spectacle.
“I know, honey, but this is the only proper way to clean out slaves.” Replies Ms. Pascoe, who is obviously not fussed or surprised to see the cruel enema, as I remain hung up by my wrists, legs tied back and far apart, gagged, and a plastic tube sticking out of my ass with water gushing out of it. “That feel better, Kevvy?” I nod my head dumbly, as I see Nurse Rebecca grab a hose and start spraying everything down the drain. I feel the water splash up on my legs, and it feels cold. I was already dreading the next part of my new morning ritual.
“Let’s just give it a few minutes, usually the water works its way pretty high up there, and then we’ll move on to the next part.”
I hear the girls gossip amongst themselves for a few minutes, only momentarily checking up on me as I squirm in my bonds as I feel the last little squirts of water come out of me, my asshole being held wide open by the plastic tube up inside it, my wrists now aching as much as the rest of the body, as all I can do is cry as I contemplate my new ‘morning ritual’.
“All done!” Nurse Rebecca exclaims, cruelly tugging out the plastic tube making me cringe.
“Good girl, good girl…” Ms. Pascoe reassures me, rubbing my tender bottom. “You took that very well! I’m proud of you, Sissy!” I simply give a muffled groan in response.
“Not very appreciative, is it?”
“He’s just tired and cranky. He’ll get used to it!” Again, all I can do is groan.
“Okay, I better let you do the next part, Ash.”
“No prob, Becky.” I see Nurse Rebecca pass something to Ms. Pascoe. “Now stay very still, Sissy, I wouldn’t want to knick you.”
I couldn’t move a muscle even if I wanted to, I was so tightly hung up, but I was scared none-the-less. I feel Ms. Pascoe’s soft fingers at the small of my back, and I hear cutting. I realize she is cutting the cord holding on my Sissy Suit! Oh thank god! When the cord is cut, I feel a tremendous release in pressure across my whole chest, waist and abdomen. Having the suit on so long, I forgot how constrictive it was to my breathing, and I enjoyed taking deep breathes through my nose. I feel Ms. Pascoe very carefully slip off the flesh-like corset and place it on one of the benches in the middle of the open shower area.
“We have to be very careful with this suit, it is very expensive and very hard to replace as you can imagine.”
“Yes, ma’am.” Nurse Rebecca said, rubbing a hand along my now naked chest. “Is it my imagination, or is his body beginning to become more curvy already?”
“Well, he has been on female hormones for a number of years, secretly of course, so it’s possible.”
“Possible!? Look at him, he’s curvy! He’s half girl already!” squealed Ellie in delight. I shivered as their eyes ran over my naked body, reporting the horrible status of my body.
“Well, the Sissy Suit is designed to give him the small waist and wide hips of a Playboy model, not the body of a girl, so there’s a long way to go with Kevvy’s transformation.” Ms. Pascoe cheerfully informs the group. ” Anyway, we have to be quick now. The guide says he should only be out of the suit for a maximum of ten minutes a day.”
“Well, lucky there’s a few of us today. Let’s get to it, girls!”
I see Nurse Rebecca handing out big scrubbing brushes that looked they were made to scrub floors, or at best, clean horses. Without any soap or water, they beginning roughly scrubbing my body. It is incredibly painful, and I can’t help but squirm amongst the four girls hands that were all over my body.
“Stay still, Sissy!” cried Liz, giving me a hard spank on my ass.
“This is just to get rid of all your dead skin, to make your skin more receptive to the Sissy Sauce. Just relax, okay, Buttercup?” Ms. Pascoe’s soothing tone did not help as I watch these girls very successfully transform me into a panties and bra wearing girl.
I feel hands all over my body, scrubbing every surface with no thought at all about my dignity. It was particularly humiliating feeling one of the girls gently cup my cock in her hand and begin to scrub around it gently, making me wince with every agonizing scratch. Curiously, I feel something that seems like leather touch the base of my cock and balls. I give an incredible scream as I feel that leather wrap around my cock and pulled tightly, putting me in pain impossible to describe.
“Sorry, honey, the whole idea behind your specially designed cock cage is to prevent blood from entering certain parts of your penis, thereby, over time, shrinking and collapsing the veins and arteries that make your little cockette swell and expand, but not the ones that don’t. In other words, your penis will shrink. You will get horny, your cockette will get hard, probably a lot, but it won’t grow because the veins can’t expand. Pretty clever, huh? It means no cock cage should hurt you again. Doesn’t that sound nice, Kevvy? And the best part is because you will have the same amount of receptors in your skin, only on a much, much smaller space, you’re little tinkle will become incredibly sensitive!” Ms. Pascoe informed me proudly to my horror, my face going white, my stomach tied in knots. They were going to make my cock completely useless other than for my own embarrassment! “Well, Kevvy, doesn’t it sound nice that getting horny won’t hurt your little cockette?” I just sniffle back my tears and nod my head dumbly from behind my large ball gag. “Good girl. Of course, you will have some surgeries done, especially to tuck back these disgusting things out of sight,” Ms. Pascoe says, rolling my balls around in her hand for a moment, making me moan. “but the majority of the work will be done by this chastity cage, and the smaller ones we have planned for when your little pee pee shrinks. To achieve the proper effect, you cannot have an erection for twelve months. But it will probably be longer.” I give a pained, muffled moan upon hearing the news. “This means every time we take you out of the chastity cage, your cock must be completely tied up. I’ve been told that when your cock becomes a bluey-purplish colour before I take you out of your cage. Sorry, babe.” Ms. Pascoe says, rubbing my head behind my ear like I was some animal. The pain around my cock was agonizing, and I squirmed in my bonds, tears coming to my eyes.
The girls finally stopped scrubbing me down, but they had left my body pink and raw, and I feel stinging all over my body. I cringe as I see Nurse Rebecca pick up the hose at her feet and begins to wash me down with the cold water, my body shivering.
“Is it purple yet?”
“Close enough, I’ll take off the chastity cage now.” I see Ms. Pascoe fetch out a tiny key from her cleavage connected to a thin, gold chain draped around her neck, and she bends down to unlock what must be a lock made out a clear, transparent plastic like the rest of the cage. I realize that I have almost no feeling in my cock as I see Ms. Pascoe hold the tiny, clear plastic cage in her hand. I hear the girls giggle as they play with my purple penis.
“C’mon girls, we’re racing the clock. Lather on the Sissy Sauce.”
I feel liberal amounts of cream squirted onto my back, my legs, my arms, all over my body. This time, I feel soft, feminine fingers rubbing my body. The cream is cool and tingles on my skin, even burning a little, and the smell of the Sissy Sauce, a sweet Vanilla, is very strong, almost overpowering. Oh god, I won’t be able to hide this perfume from my girlfriend with a thick sweater!
I squirm in between the slippery hands, gasping as they trace their fingers across my nipples and in between my butt crack and around my hole, where they are particularly thorough. I moan behind my gag in pleasure as I feel the cream applied to my cock, despite the lack of feeling it stills sends waves of ecstasy race through my body, and I can’t help but strain to push my cock into the hand that is massaging it.
“Whoops what, Ellie?”
“Well- well- Sissy kinda squirmed, and I knocked and loosened the leather strap around his little dick, and, well, I think his got a little chubby.”
“Oh, Ellie, you stupid- if you were one of these slaves, you would have received a spanking so bad you couldn’t sit down for a week! I just explained he can’t have a hard-on for a year, at least, and we couldn’t keep it down for a day!”
“I’m sorry, he was squirming his little thing into my hand!”
“He’s a pathetic sissy, Ellie! What do you expect to happen when you beginning rubbing his winkie with cream!?”
Nurse Rebecca cranes her neck to get a better look at my half-hard cock, still a far from impressive two and a half inches. She says, with a wide grin on her face as she soaks in my tiny cock, “I suggest, Ash, you use some sort of clamp, with a screw-down lock-on feature, like a carpenter or a metal worker might use. It would be impressive if it could get hard with that thing hanging off its cock.” I cringe from her inspection and than from her suggestion.
“Good idea, Becky, I just might do that. I realize now it was my mistake to trust a simple leather strap. Oh well, you live, you learn. In the meantime, we’re going to have to milk Kevvy so we can get his cage back on.”
“Oh god, I don’t want to touch that thing.”
“I don’t mind touching his limp little toddler dick, but stroking it hard so he can get off? I’m not doing that!” says Ellie, momentarily pausing from rubbing the lotion in to my butt cheeks.
“That’s okay girls, there’s more than one way to milk a sissy. Wash him down, make sure he has no body hair at all on his body and reapply the second coat. I’ll find a satisfactory way to milk Kevvy.”
Cold water is immediately sprayed all over me, including my cock and ass which was especially cruel, and then every inch of my body inspected by the two Sadler Sluts and Nurse Rebecca. It was so embarrassing feeling the girls fingers all over my body, my only resistance a futile squirming.
“I think Kevin here must like this stuff, hey?” says Liz, as she pokes my hard cock with her finger, making it sway from side to side under me, sending waves of shameful pleasure through my horny body. I simply blush red with their comments as I feel the fingers continue to explore my body.
“I can’t see any hair.”
“Okay, girls, reapply the Sissy Sauce. And remember, it has got to be rubbed into the skin, it’s not being washed off this time.”
I whimper when I hear this. No body hair? Not even on my cock or ass? Gawd, how am I meant to explain that? And the strong Vanilla smell was already extremely strong after the rinsing, how bad was it going to be when they reapplied a second layer? The girls eagerly began spreading the lotion all over my body, paying particular attention to my butt, my nipples, which they couldn’t help but trace their long fingernails along sending pleasure running through my body, and my face, where they pinched my cheeks and squeezed my face as they giggled away. But they paused when the last thing to do was my fully erect cock, the blood returning the feeling to it, the beautiful girls soft fingers making a trickle of precum leak out of it.
“You big babies, I’ll do it.” Sighs Nurse Rebecca as I hear her snap on a rubber glove.
“Oh, Becky, be careful!’ Ms. Pascoe exclaims as I hear her walk to us from across the open shower area. “He’s a little preemie, he will shoot with only a bit of fondling.”
“Fondling? Really? It’s that pathetic?”
“Oh, most definitely. He will cream in your hand after only a gentle rubbing.” I groan in disgust and shake my head in denial. “It might be cleaner if we milk him my way. Can you spread his cheeks for me?”
I begin squirming vigorously as I feel Nurse Rebecca’s plastic gloves spread my ass cheeks and I feel the short plastic tube inserted back into my ass, making me scream in pain behind my gag as the hard plastic pushes its way into my sensitive hole, spreading it wide open.
“This will be a good test to see if he is a true Sissy. I’m going to massage his prostate with my finger. A man would be disgusted, getting off the last thing on his mind. A sissy, well, a sissy will shoot creamies all over the place. Let’s see what happens…” Ms. Pascoe says ominously as I hear another snap of a plastic glove.
I shiver in fear, and then moan in pleasure as I feel Ms. Pascoe’s long, latex-covered finger enter my wide open ass and begins to gently rub my insides. After the torture my behind has suffered, this anal massage feels like a dream. I hear the girls begin laughing loudly as I realize I am squirming on the finger, trying to get it deeper into my ass, as I continue to let out muffled moans.
“Oh my God, he loves it!”
“Well, this is enough for me. He’s clearly a born sissy.” says Liz cruelly.
“Just wait for- ahh, here it is.” Waves of pleasure rock my body, and I arch my back, pressing the finger deeper onto the sensitive spot my Mistress has found. “The prostate- shouldn’t be- well, there he goes.” I feel my orgasm build-up and release in mere moments, and I spray white goo all over the shower stall. I hear the girls laughing hysterically as I come back to my senses, realizing that I have just orgasmed after my ass was finger fucked! And only for a few seconds!
“Born sissy! It’s all I can say, born sissy!” says Liz in between her fits of laughter.
“I can’t believe it, they told me about Sissies, but- but, I just can’t believe it!”
“He could of never pleased a woman, obviously, it really is rather lucky for him, er, her, that Wingett made her the Sadler Sissy.”
“And just think, Becky, he’s all yours for thirty minutes a day, every day! Have fun teaching this sissy how pathetic he really is.”
My face is beet red and flustered as I hear their conversation, making me feel two inches tall, as I feel gloved hands massage the Sissy Sauce onto my dick, making it tingle, and then the incredible pain of the chastity cage being locked on, absolutely crushing my limp dick. As I let out muffled screams and squirm to no effect in my bondage, pain racks my body and tears flow freely down my burning, red cheeks.
Ms. Pascoe leans in to me, revealing a deep cleavage, so she can whisper “Well, that is your new morning ritual. It won’t be this much fun every day, but you get the idea.” She gives me a little kiss on the cheek and stands upright. “He smells absolutely lovely! Sweet Vanilla, it’s just lovely. Just string him up, put the Sissy Suit back on and get him to clean this goo he just sprayed everywhere with his tongue. Sissy has to earn his creamies. I’ll get his outfit ready for the day.”
Chapter 4: New Arrivals
The last couple of weeks had been the worst in my life. The terrible sessions with Nurse Rebecca were just the beginning. I had to avoid everybody I know; friends, team mates, especially my girlfriend. As soon as she found out I was a sissy, I knew the whole school would find out not long after. I ended up spending all my time sulking in my dorm or spending time with Ms. Pascoe and her friends, who spent all their time teasing me mercilessly. But at least they were talking to me, even if they did insist on calling me ‘Miss Kevvy’.
Ms. Pascoe gave me a long list of all the rules I was to follow and each and every person at Sadler could enforce them. I cringe every time I think of the countless people who have snaked their hands down the front of my pants to make sure I was wearing my panties and Chastity Cage. I will never forget the cruel, smiling faces of all the girls who cupped my locked up cock in their hand, most with a snide remark letting me know I would never get to use it again, let alone with them. The worst of them played with the butt plug poking out from my butt, sometimes openly in the school corridors! They just laughed as I squirmed and blushed shyly, praying that no one would see or catch on, trying not to whimper in pain in front of the gorgeous girls.
Near the top of the list of rules was wearing the clothes Ms. Pascoe instructed me to wear any time I wasn’t in public. As I walk into my dorm room, breathing a sigh of relief that I made it through another day of classes without someone spying my training bra through my shirt or my pink panties poking out from the top of my pants, I dump my backpack on the ground and check out my phone to see what super-feminine outfit Ms. Pascoe is making me wear tonight. I still found it extremely weird to be wearing the tight, thin panties and prepubescent training bra, I couldn’t help but feel feminine and girly when I looked down at my bra and panties.
The worst part of the last week in particular had been my growing horniness. I hadn’t been allowed to cum since my first session with Nurse Rebecca. Nurse Rebecca had fun everyday stroking and teasing my body as I squirmed my bonds furiously, but she never allowed me release. I couldn’t help it, I hadn’t been able to think straight for days, I was so overcome with lust as I licked Ms. Pascoe’s feet last night, I begged her, begged her to let me cum. And she told me what I was terrified to hear- ‘when we begin your Anal Sex Training regime you’ll be able to cum as much as you want. Just be patient, Sweetheart.’ The answer terrified me. I had to escape. I just had to escape.
Maybe the scariest part was that torturous parts of my life before, the incredibly constricting corset and butt plug did not hurt anywhere near as much as they did. I knew my body was slowly changing shape, my waist shrinking while my poor asshole is stretching, and it made me sick just to think about it.
I slip my t-shirt over my head and slip my baggy jeans to my ankles after stepping out of my shoes. I hate the feeling of being naked other than bra and panties, and I quickly slip the training bra over my head. I almost burst out crying when I catch a glimpse of the puffy nipples of a young teenage girl in the mirror. I can’t help but walk slowly to the large mirror, not taking my gaze off my distinctly larger, distinctly puffier, distinctly feminine nipples. My once strong, hard, manly chest was becoming soft, and now I had the nipples of a teenage girl! I almost burst out crying right there, the reality that I was becoming the girl they wanted me to be finally hitting home.
Unconsciously, my hand goes to my naked chest and starts rubbing my pink nipples, sending electrical waves of pleasure through my horny body. The soft, sensitive nipples begin to harden making them stand erect and pointy- just like a girls. That is it, and I feel the tears start to roll down my cheeks as I start to cry openly. Two week ago, I was a promising football player with a promising future. Now I am standing crying at the mirror as I inspect my young teenage girls breasts while considering what else lies ahead of me in my life as Sadler’s Sissy Slave.
I hear keys working their way into the locks of my dorm’s door, and I just stand there shocked, covering my chest instinctively, not expecting my new roommate’s arrival so early.
“Hello, lovely!” Ms. Pascoe says cheerily as she pokes her head past the door. “Oh my gosh! You look so adorable in those lacy, frilly panties! I love how they are so ‘little girly’, but they are still tight and high cut enough to show off that great ass of yours!”
“Th- thank you, ma’am.”
“And instinctively covering your chest! Oh, that is especially girly!” Ms. Pascoe says, giving a little clap of her hands in joy. “Oh, another crying session? Poor, Kevvy. That’s okay, honey, I know the last couple of weeks has been hard and no one really expects you to take it like a man.” Ms. Pascoe says, chuckling to herself. “It could be an effect of the hormones, but I’m not really sure. But I have to say, I am extremely proud of you for taking this change so seriously, Kevvy. I talked to the other Mistresses and Masters, and they said they never caught you once out of your cute panties and training bras.” I shiver in humiliation as I recall again the countless checking of my girly underwear by complete strangers in every corridor of the school. “Tell me, how did you ever explain your pretty panties to your meathead football team mates in the locker room?”
“I- I- told the coach I had a back injury and my back was in a brace. I haven’t been playing…”
Ms. Pascoe giggles in delight. “Tsk tsk, naughty sissy, lying like that! Little girls aren’t meant to lie!”
“I’m- I’m sorry, ma’am.”
“Don’t be, Sissy, you’re just a little shy. It’s totally understandable for a young girl to be shy around those big, strong men. But, let’s see what you are so shy about in front of your Mistress.” Ms. Pascoe says as she moves behind me, her gorgeous figure moving into the mirrors reflection, still looking incredibly sexy in just her tight t-shirt and small denim shorts revealing her long, tanned legs, her long golden hair tied in a neat ponytail. Her smiling face and confident demeanor make quite the contrast to my already visibly softer, tear soaked face, as I stand naked other than the girliest pink and lace panties I had ever seen. She grabs me by the wrists and moves them to my sides. I can hear her audibly gasp when she sees my new pale, puffy nipples. “Oh my- I was expecting a change, but not so much so soon! You have breasts now, Kevvy! Isn’t that just great, darling!?”
“Y-yes, ma’am.” I mutter, squirming slightly in the grip of my Mistress, almost dying of embarrassment as she inspected my body and my new budding bosoms.
Ms. Pascoe releases her grip on my wrists and gives a slightly disappointed ‘hmph’. “Well, I for one am very excited. You just haven’t seen how much fun we can have now.”
With this, she begins squeezing my nipples with her fingers, racking my body with pleasure. I cannot believe how sensitive my nipples are now! I arch my back and begin moaning. “Ooh, Sissy likes it.” Coo’s Ms. Pascoe. I open my eyes to see our reflection in the mirror. Ms. Pascoe’s gorgeous face, her perfect smile and blue eyes glowing in delight as she reaches under my armpits from behind me to tease and massage my nipples with her fingers, my face is red and flustered and contorted in pleasure as my horny body squirms up and down against Ms. Pascoe’s body. I look like a horny, moaning whore.
“This is a lot of fun, isn’t it Sissy?”
“Yes, ma’am!” I manage to get out between my whines and moans as my incredibly sensitive nipples are teased and twisted.
“But do you deserve all this fun?”
“Wha- what do you-” I cannot finish my sentence as Ms. Pascoe suddenly pinches my nipples hard, making me scream in pain.
“The correct answer was ‘No, ma’am’, got it, Sissy?”
“Ahh- ahh- yes, ma’am! No, ma’am! Ahh, please let go- ahh!” I scream, squirming wildly now between the delicate fingers of my Mistress.
“Tell me first why you don’t deserve to have Mistress play with your nipples?”
“Ahh- ahh- because I am a Sissy and a Slave, ma’am!”
Ms. Pascoe laughs at this, before pulling on my nipples harder, making me scream and squirm even more. “Aww, that’s cute, but Sissies are made for fun! Guess again, Sweetums.”
“Ahh- I- I- I don’t know, ma’am!”
Ms. Pascoe leans in and whispers, “Where are your high heels, honey?” My face goes pale as I realize I have forgotten to follow one of Ms. Pascoe’s instructions.
“Oh, ma’am, I am so sorry, I was just getting changed, and- and- oh, please don’t use the Educator! Please!” I was almost shocked by my own begging, my own desperate pleas. But I just couldn’t help myself.
“I told you to wear your high heels every moment you weren’t in public, didn’t I?”
“Yes, ma’am, I am so sorry, ma’am! I promise it will never happen again! I swear Just don’t shock me, please!”
Ms. Pascoe finally releases my nipples, and I gasp in relief. But as the pain subsides, I realize that all this playing with my nipples has left my body on edge and I’m sure I can feel precum leaking out of my chastity cage.
“Oh, I am glad you are learning so fast! Because you are your making your Mistress so happy today, I will give you a choice for your punishment. Forgetting to wear your high heels when not in public is a very, very naughty thing to do, so I’ll either shock you with the Educator-” Ms. Pascoe says pointing to the button on her bracelet around her wrist that would send an electrical shock through the punishment plug up my ass.
“No! Anything but that!”
“Well, I was going to give you the option of ten spanks, but for interrupting me I am going to make it twenty. How does that sound, Kevvy? Sound like a nice change from the mean, old Educator?”
“Yes, ma’am, twen- twenty spankings sounds very nice.” I manage to stammer out, my body shaking in fear, absolutely defeated. How have they conquered me so easily?
Ms. Pascoe walks over to a locked cabinet sitting in the corner of the small living room, the one she says is filled with ‘tools of the trade’, opens the small padlock with a key and removes a scary looking riding crop, before sitting down on the couch.”Now, come over here, Kevvy.”
I gulp and look at the light blue carpet on the ground as I begin to make my way over to the beautiful girl who I call my Mistress. I have been racking my brain trying to think of a way to escape my slavery. But it seemed so hard… “Forgetting something, Kevvy?” Ms. Pascoe says, looking at me sternly.
“Oh, sorry, ma’am.” I scurry to the cupboard to fetch a pair of bright pink, four inch high heels. Tracking devices planted under my skin, a butt plug that will send a signal that will make me unconscious if it doesn’t feel my body heat. I lean down, sulking a bit as I slip my sore feet into the cute heels that had caused them so much pain. ‘How was I ever meant to escape their perfect trap? There must be a way…’ I think to myself as I daintily walk back to Ms. Pascoe, teetering on the pink high heels. Never have I felt more like a girl as I put one foot in front of another like I have been instructed, making my wide hips and tight butt swing from side to side, wearing only my frilly pink panties, my new nipples pointing erect.
“Oh Kevvy, your heels and your new tiny titties make you look so sexy right now, but you’re going to have to practice walking in high heels. Sure, you look dainty, but not graceful.”
“Yes, ma’am, I shall try harder in the future, ma’am.” I say, looking straight at the ground.
“Oh, good answer, Kevvy. You are getting me so hot right now.” Ms. Pascoe says in a sultry tone, her eyes looking up and down my almost naked body. “It’s just not that you look so sexy in just those cute panties and high heels,” Ms. Pascoe says lustily, reaching out to grope my soft ass, making me cringe, “It’s that nothing gets me hotter than humiliating little boys like you.” I only whimper in response. “Oh yeah, that’s so sexy. Now get into position and count the spanks, got it Sissy?”
“Y-Yes, m-ma’am.” I say, shivering in fear, wishing I was somewhere else as I carefully lie myself over Ms. Pascoe’s lap in my pink high heels, trying to prepare myself for my first ever spanking.
“No, no, no, silly Sissy. I want to try out your new breasts. Kneel down in front of me with your hands behind your head.”
“Are you arguing with me, Sissy?” Ms. Pascoe says in a stern and scary tone that makes me slide off her lap very quickly.
“No, ma’am!” I quickly reply, kneeling down in front of the sexy girl so she is now looming over me.
“Good girl. You’re so well behaved most of the time, I forget that you are a brand new slave. Remember, honey, that sexy as hell ass of yours is your main attraction at the moment, and we wouldn’t want any punishments ruining the show for the boys.” Ms. Pascoe says with a wink, as I am very much reminded of my new purpose in life- pleasing men.
I wonder how bad a spanking on my chest can be, after all, they are only new breasts, I am still very much a man, regardless of how look with my new breasts and the Sissy Suit that gave me my wide, feminine curves. As I see Ms. Pascoe raise the black riding crop and feel the first stroke come down flush onto my right nipple, I hear a loud slap of leather on skin and my own scream as I see white lights in my vision, and suddenly all my questions are answered- this is going to be torturous. “One, ma’am!”
“Good girl.” says Ms. Pascoe bringing down another firm stroke to my left nipple. Tears come to my eyes as I scream again, the pain making it feel like my chest was on fire.
“Two, ma’am!” I say through the tears. When Ms. Pascoe brings the crop on my right nipple for a second time, I scream loudly and begin sobbing, the pain is so much worse than the first painful stroke. As Ms. Pascoe raises her arm to bring down the riding crop on my left nipple, I can’t help but flinch, turning the best I can in my tight Sissy Suit and covering my body so the riding crop hits my shoulder.
“Bad girl! Bad girl!” Ms. Pascoe says like an owner talking to her pet, as she brings down the riding crop on my shoulders a few times, the leathery slapping sound ringing in the small room. “You are being a very bad Sissy! Now, are you going to behave and sit still or am I going to have to tie you up and get my studded paddle?”
“No, ma’am! I’ll be good, I’ll be good, I promise!” I say through my tears, forcing myself to sit upright and move my hands off my soft, smooth chest. I have learnt that Ms. Pascoe doesn’t make idle threats. I close my eyes, grit my teeth and put my hands under my legs as it takes every effort to not to move from the feet of my Mistress. I yelp in pain and squirm involuntarily as Ms. Pascoe resumes the spanking with the hard, leather riding crop. I squirm and squeal and begin to sob as Ms. Pascoe continues to bring down the riding crop on my super sensitive chest. I can hear Ms. Pascoe laughing to herself as she watches me uncontrollably squirm and sob at her feet.
“Oh, this is so hot. You look like a sexy girl just beginning to get breasts, crying at my feet in only panties and high heels. And to think you used to spend all your time trying to prove yourself a man’s man on the football field.” Ms. Pascoe says, her lusty tone returning to her voice. ” Agreeing to be in charge of your training was the best decision I ever made.”
And all I can do is say “Yes, ma’am.” in between my sobs.
“Ashleigh, the door was unlocked, so I- what the hell!? What are you doing, I thought you wanted me to give a make-over to your latest boy-slave?” I hear someone walk in to my dorm from behind me, and I can’t help but cover my now red and swollen nipples, making me cringe as I touch them.
“Oh, hello, Natalie. This is my latest slave- his name is Kevin. He was very bad earlier, he forgot to wear his pretty high heels.”
“He’s a boy!? He looks just like a girl to me…” I whimper when I hear the comment, but it is the familiarity of the voice coming from behind my kneeling position that sends shivers down my spine. “Kevin? Kevin Morgan?”
I look up through my teary eyes to see my girlfriends best friend standing over me, looking at me with a shocked face. “H-hello, Natalie.”
“Oh my, you two know each other? How delightful!” Ms. Pascoe’s says with a big smile on her face. “Kevvy is the latest Sadler Sissy. Mr. Wingett wants to make him the sexiest Sissy yet, and he has put me in complete charge of the whole thing! I am so excited about it all!” Ms. Pascoe giggles, making me realize for the first time what an honour and huge show of faith it must be to be entrusted with a slave, with a life. Obviously she is good with slaves, I think to myself as I feel a sharp whack on one of my hands covering my chest. “Did I tell you that you could cover your chest!” Ms. Pascoe growls, pointing down at me with that damn riding crop.
“No, ma’am.” I mutter as I blush red when I uncover my chest and I hear Natalie burst out in fits of laughter.
“I cannot tell you how many conversations I’ve had with Alex going on and on about how sexy Kevin is, despite how tiny he is. I wish she could see him now! Look at those pointy nipples! He has tits!”
“Alex? I don’t think I know her.”
“Alexandria Hadlee, that’s Kevin’s girlfriend and my best friend. I can’t believe he hasn’t told you.”
“Tsk tsk, keeping secrets from your Mistress, Sissy? That’s very naughty.” Ms. Pascoe says giving a sharp whack to my right nipple, making me yelp in pain. “I was just in the middle of a punishment. Do you mind if I finish up before we get started.”
“No problem, I’ve got to get a control of myself, anyway.” says Natalie in between her fits of laughter.
Ms. Pascoe laughs at this herself. “Okay, thanks for that.” she says in a cheery voice before turning to me with a stern face and tone. “Okay, count them out, Sissy.”
I could feel my face burning with embarrassment as Natalie laughed at my body and I simply submitted myself to a titty-spanking, kneeling at the sexy Ms. Pascoe’s feet, seemingly naked other than pink girly panties and high heels, my hands sitting on top of my head. “Yes, ma’am. Ahh! Fourteen, ma’am. Ahh! Fifteen, ma’am. Ahh, ahh! Sixteen, ma’am! Ahhhhhh!! Seventeen, ma’am! Ahhhhhh!! Ahhhhh!! Eighteen, ma’am! Ahhhhh, ahhhhh, ahhhhh!!! Nineteen, ma’am! Ahhhhhhhhhhhhhhhhhhhhhhh!!!!! Twenty, ma’am!!” Ms. Pascoe puts all her remaining strength in the last, hard slap of leather on my super sensitive chest, turning me into a sobbing, squirming mess kneeling at her feet.
“Alex could not stop telling me what a big, strong man he was! And now he looks like a sniffling twelve year old girl!” Natalie manages to get out in between her laughter, her face bright red from the effort.
“Oh, trust me, Kevvy is far from a real man, he is most definitely a born sissy. Honey, stand in the corner while Natalie and I get ready.”
“Y-yes, ma’am.” I stammer, my lower lip shaking uncontrollably after my harsh punishment. I get up and daintily walk to the corner, provoking another round of laughter from Natalie.
“Silly, Sissy, turn around and face the wall with your hands on your head.”
“Yes, ma’am.” I mutter, following the instructions, secretly happy that I was covering my naked chest from the two.
“Oh my God, look at that incredible ass! So tight and yet rounded. I love it!” Natalie screams with delight as she races to the corner where I am standing. She unceremoniously tugs my panties up my butt crack, effectively giving me a wedgie and turning my panties into a thong, so she can get a better look at my reshaped ass. “So sexy!” she says, still holding the waistband of my panties, putting an uncomfortable pressure on my cock and balls trapped in their tight chastity cage under the Sissy Suit.
“I know! Isn’t it fantastic? Let me show you something else.” I hear Ms. Pascoe say as she walks across the room before I feel her placing her hands on my naked shoulders so she can spin me around. With my panties wedged high up my butt crack, the panties are extra tight around my crotch, revealing my shameful camel toe.
“Oh- my- God!” I can’t believe it! You’ve taken away his cock!?”
“No, it’s a new feature of the Sissy Suits. It comes with a strap that looks just like a young girl’s pussy. His tiny dicklet is trapped under it, not that you can notice.” I whimper at this comment. “Okay, this is a lot of fun, but Sissy’s new roommate will be here soon and you know first impressions count.”
“You’re right, let’s get to work.”
Ms. Pascoe spins me back around so I am once again facing the corner like a naughty child. I hear the unzipping of bags and items being placed in front of the mirror as the two shuffle about. ‘I wish they would tell me what’s going on…’ I think to myself, as I realize too late that my hand has wandered off my head and began fumbling with the panties uncomfortably lodged high up my ass.
“Sissy, what are you doing!? Did I give you permission to take your hands off your head, never mind the audacity of touching your panties without permission! I can’t believe you are embarrassing me like this in front of Natalie! I told her you were a well behaved slave. What do you have to say for yourself?”
“I am so sorry, ma’am, I wasn’t thinking! I- I- please, please don’t use the Educator on me!” I say, turning over my shoulder, where I see Natalie with a broad grin on her face as she sees me beg and plead. I was very mean to her, as I was to almost every girl I know, and now I think I’m going to pay for it.
“You’re very lucky, Sissy, that we can’t have you crying right now, and since you seem to burst out in tears from the mildest things these days, we can save your punishment for later.”
“Oh, thank you, ma’am!”
“Now, please put on your matching baby doll night gown and return with a chair.”
“Yes, ma’am!” I say, barely containing my gratitude that I have avoided punishment for a serious offense, Ms. Pascoe gave me strict instructions to never touch my panties or bra. And not only this, I was being allowed to cover my nakedness in front of Natalie.
I had to admit, I had never seen the night gown that matched these girly panties, and I cringed when ! saw it hung up in the closet of my bedroom. It was pink, frilly and lacy, just like the panties, but it was also very sheer. As I slipped the thin, light material over my skinny body, I immediately notice my new nipples were almost pointing holes through the barely-there material. As I looked further down, I noticed I could see my wide curves and bright pink panties through the material. The final humiliation was how short the dress was, the bottom of the pink, baby-doll night gown didn’t cover the bottom of my ass cheeks. I was blushing furiously as I returned, both Natalie and Ms. Pascoe wearing huge smiles on their faces as they looked my body up and down.
I grabbed a wooden chair from the other side of the room. Last week, this would have been an effortless task, but I grunt as I lift the chair, and it takes serious effort to hold it in my grip as I move it in front of the mirror. One of Ms. Pascoe’s new rules says I could not lift a weight of more than two hundred grams, barely enough to cover one of my text books. You can forget my rigorous weights regime. Obviously, the atrophy of my muscles has taken an immediate effect, and this scares the hell out of me.
“Good girl. Now take a seat.” I nervously take a seat in front of the mirror. I see my scared, tear-soaked face, as well as the smiling faces of Natalie and Ms. Pascoe standing behind me in the reflection. The image leaves no doubt who is in control here. “You may have been wondering what Natalie is doing here. Well, if you ever listened to her, I take it you were quite the jerk before you became my Sissy Slave, you would know that Natalie is an excellent cosmetologist who has come here to help you out.” I must of given a confused look, because Ms. Pascoe quickly adds, “That’s a beautician, silly Sissy, she’s here to give you a make-over!”
“What!? But- but- I thought it was going to be kept a secret!”
“And you said you would be a good little Sissy, didn’t you? Don’t worry, we won’t be doing anything too drastic, today. Consider this more for practice. You will have to learn to do this yourself soon, I expect you to be immaculately made-up every day. I will tell you when this rule will come in to effect, okay Sissy?”
“Y-yes, ma’am.” I say, horrified about my latest humiliating task.
“Look, he’s about to start crying again. This could be tricky.”
“Sissy, no more crying! If I see even one more tear, the first thing I am going to do is teach you a lesson with the Educator! Got that!?”
“Good, then let’s begin. Close your eyes.”
I close my eyes and I hear Ms. Pascoe and Natalie move in front of me. I feel a warm, thick goo placed on my eyebrows, and before I realize what it is, I feel it ripped off, taking a lot of my eyebrow hair with it.
“Ah! What are you doing!? Waxing my eyebrows? Everyone is going to see!” Ms. Pascoe simply slaps my face hard.
“Sissy, quiet! Don’t you realize we’re working on your face! One more move, one more sound, and I promise that I will use the Educator all night long!” Ms. Pascoe didn’t make idle threats. I shut up and closed my eyes and tried to ignore the fingers all over my face.
The girls talked about different things, like foundation and eye shadow and all sorts of stuff., but I was too shocked, too scared, too embarrassed to process what they were saying. It was scary as they slowly waxed my eyebrows into two fine arches. It was scary as they made me purse my lips so they could apply a bright pink glossy lipstick on my already full lips. It was scary when they spent an age filing and polishing my nails. It was scary when they glued huge, heavy fake eye lashes onto to my eye lids. It was terrifying when I was finally presented my new face- bright pink lips, cheeks and eye shadow that matched my pink, transparent night gown. My new, large eyelashes gave my face a more feminine look then I could ever imagine, only highlighting how wide and vulnerable my eyes already looked. It took every fibre in my body to stop myself from bursting out in tears.
“What do you think, Kevvy? Don’t you look just adorable!” Ms. Pascoe squealed in delight, obviously overjoyed at how well I came out.
“I think he is going to cry again. Oh, I forgot something.” with this, Natalie pulls out a pink ribbon with a bow in it. I gulp as I see the latest addition to my outfit. Natalie carefully positions the pink ribbon in my hair, using it as a hair-band, pulling my boys haircut back so that it looked just like a young girls. I could not believe the image staring back in the mirror. I looked like a cute, young girl with wide, teary eyes. A month ago, if I had this walking down the street, I would have stop and changed direction so I could walk and flirt with her. And now I am this sexy girl!
“Natalie, you have truly outdone yourself! She is gorgeous!”
“Oh, so he’s a she now?” Natalie says, giggling.
Ms. Pascoe laughs at this. “I can’t help it, look at him! He looks like one of the cutest girls I’ve ever seen!”
I hear a key enter the lock of my dorm door, but to me it sounds like ominous rolling thunder. I instantly try to get out of my seat to run and hide so no one else can see me looking just like a sexy girl, but the hands of Ms. Pascoe and Natalie keep me firmly in place in my chair. The door swings open and a large, young, muscular black man steps through.
“Oh sorry, I must have the wrong room.” the tall man says in a deep voice.
“Are you John? The new Sadler Stud?”
“Yeah, that’s me. Look, you just can’t come bursting in to my room, there is a roster I have to adhere to-” John is interrupted by Ms. Pascoe’s laughter.
“Oh no, you misunderstand. I am the Mistress of your roommate.”
John laughs at his own assumption. “Oh sorry, I thought you were, you know, one of the girls looking to get with me.”
“Don’t worry about it.” Ms. Pascoe says, giving a little laugh at the misunderstanding.
“So where is my new roomie then?”
“Right here.” Ms. Pascoe says proudly, tugging me up by the arm so I can be presented to this man who towers over me. His jaw almost hits the floor when he sees me in my short, transparent nightgown that does not hide my pink panties still wedged high up my butt crack revealing my ass cheeks, my nipples pointing through the thin material, my face made-up immaculately so I looked just like a horny teenage girl on the prowl.
“But- I thought I was rooming with a guy?”
“He is a guy. His name is Kevin Morgan, you may remember him from a few of your classes.”
John scratches his chin, and a look of recognition eventually comes across his face. “Yeah, yeah, I think I do remember him. He was a real soccer superstar, wasn’t he?”
Natalie just laughs at this. “Certainly not any more!”
“Damn right. he looks like one of the sexiest girls I’ve ever seen. She might need some bigger tits, but she is still god damn sexy.” he says, his eyes leering as they look up and down my body, making me feel extremely self conscious, but with Ms. Pascoe and Natalie holding my hands on either side of me, all I can do is shuffle nervously on the spot. I could not believe a guy was looking at my body with just lust in his eyes!
“Kevvy, something I should tell you about John. He is a Sadler Stud, someone with the responsibility of serving the women of Sadler. He has been placed on a special regime of drugs, basically designed to make him sexually insatiable.”
“It basically means he is always hard and horny. That could drive a man crazy!” This is particularly frustrating, considering I have been constantly horny for a week with no sign of being allowed to cum anytime soon. “Now I am no one’s fool, a big strong man and a weak little girl living alone together, things are going to happen. I want to make it perfectly clear that John is not allowed to fuck you up your ass…yet. You must use your mouth to satisfy him.”
“What!? You want me to blow him?”
“I don’t know if I’m comfortable having sex with a man.”
“Oh John, the last thing you should think of Kevvy is as a Man. He is a Sissy, a born Sissy, designed for the pleasure of others. If he can’t get you off, then what good is he?”
John slowly nods his head. “I guess, and I mean look at her, she looks damn sexy.”
“That’s the spirit! Now, I have an early start tomorrow and I want to teach Kevvy the ropes before I go. Do you mind if we start right away?”
I am absolutely shocked by this conversation and I struggle with all my strength, but I can barely budge the tight grip of Natalie’s and Ms. Pascoe’s grip around my wrists. “You can’t do this- please, don’t make me do this!” I plead.
Natalie gives me a firm spank on my ass, making me flinch. “Shush now, Sissy.”
“Do we have to call him Kevvy and Sissy? I kinda want to imagine that she’s- it’s just a girl.”
“Hmm, well Mr. Wingett hasn’t given me the name he has picked out yet, and I don’t want to get Sissy confused, so why don’t you just call her Slut for now.”
Jon laughs at this. “Awesome, sounds great!”
Ms. Pascoe turns to look down at me. “Okay, first thing you need to do, Ke- I mean, Slut, is to massage his cock and make sure it is nice and hard. If it’s hard, that means it’s your job to suck it. Understand?”
“But- but- wha-“
This time it is Ms. Pascoe who gives me a firm spank to the ass, making me jump a little. “Stop playing games, Slut, you know the price of disobedience!”
For the first time, I seriously consider suffering the incredible pain of the shock of the electrical butt plug shoved up my poor ass instead of following one of Ms. Pascoe’s commands as I look at the huge, growing bulge at the front of John’s jeans. But as I feel Ms. Pascoe release her grip on my wrist and begins to reach up to her bracelet, I quickly scurry across the room, putting my new clear-polished fingers on John’s large cock through his jeans. I did it before I even realized, and now that I am standing holding another man’s cock in my hand, I realize I have never felt more ashamed, embarrassed or humiliated.
“Good Slut, very good Slut.” John says, running his hands through my hair.
“Is it hard, Slut?”
“Good. Okay, unzip him and bring it out.”
The command hits me like a ton of bricks, and my hands start shaking wildly. But I slowly unzip the jeans, the zipping sound echoes in the quiet room ominously. I am sweating, feeling so extremely nervous as I reach into John’s open fly and pull out his huge, rock hard black cock. I have never see another man’s erect penis in real life and I am absolutely shocked at how it puts mine to shame.
“It must be quite a revelation to see a real man’s cock, huh, Slut?” Ms. Pascoe chirps cheerily. “Okay, get on your knees and begin licking up and down the underside of the shaft.”
“Y-y-yes, m-ma’am.” I am so nervous it feels like I am going to be sick. I am so ashamed as I get down on my knees, listening to Natalie’s laughter, that my face is burning red and I feel tears welling up in my eyes. I try to blink them away, remembering Ms. Pascoe’s terrifying command, but as the huge black cock bobs in my face, its musky smell hitting my nostrils, I can’t help but whimper and cry.
Ms. Pascoe, ignoring the tears, I think, continues to instruct me sternly. “What are you waiting for, Slut? Lick that dick!”
I nervously poke out my tongue and I hesitantly lean in until the large, warm member is brushing my face. I slowly begin licking the underside of John’s huge penis. I instantly hear him let out a long, deep moan.
“Good, he likes it Slut, that’s very good. Now while you do that, begin to massage his balls with your hands.” I whimpered when I heard the awful command, but I simply kept licking, the horrible musky smell dominating my senses, as I reached up and began massaging his heavy balls. “Very good, Slut. Now put the balls in your mouth one at a time. Roll them around in there, press your tongue hard up against them.”
My mouth fell open when I heard this, but I soon found myself lowering my head, opening my mouth as wide as it could get so I could put John’s large, smelly testicles in my mouth. They filled my mouth completely, stretching it out. In the corner of my eye, I see Natalie positioning herself so she can get a good angle of the photo she is taking with her camera phone. I release a muffled squeal as I realize that my girlfriends best friend is taking pictures of me dressed up as an incredibly sexy girl, my mouth stretched by John’s large testicles.
“Don’t get distracted, Slut, you have a job to do. John, has she worked enough on your testicles?”
“She needs to work the tongue against the sides. She is being too soft.”
“You heard the man, really work and press down with your tongue on his balls.” Tears are now freely flowing as I massage John’s balls with my tongue. He releases a moan of pleasure as I begin to do so.
“That is awesome, Slut!”
“The nice man just gave you a compliment. What do you say, Slut?”
With John’s balls still filling my mouth, I give a muffled ‘thank you’.
“Now, take the balls out of your mouth and begin massaging them in your hands again. Lube John’s cock with your tongue completely, and then put it in your mouth.”
My body now is in a complete state of shock, barely hearing Natalie’s laughter or John’s guttural moans. But I hear Ms. Pascoe’s commands clear as a bell, and I follow obediently. I begin massaging John’s now slimy balls , looking huge in my small hands, as I begin licking all over John’s cock.
“Pay particular attention to the head of his cock, lick it like you would an ice cream.”
As I begin swirling my tongue around the head of John’s bobbing cock, I can’t help but imagine when my girlfriend did this for me once. It felt so great that I could never forget it. Now here I was, sucking off the biggest cock I had ever seen, and I realize I will never forget this nightmare either.
“Now open up your mouth wide and go as far down as you possibly can.” I cringe when I hear this. I feel sick, I feel like I’m going to faint, but all I do is close my eyes, open my mouth and push the cock into my mouth until it hits the back of my throat. I cough and splutter as I gag and take the cock out of my mouth so I can gasp for air. “That was a good try, Slut, you will soon lose that gag reflex. But keep your eyes open, a cock sucking slave should keep eye contact with her Master. Understand, Slut?”
“Yes, ma’am.” I say in between my gasps, red faced from the exertion, red faced from the sheer embarrassment and humiliation of being forced to suck a cock against my will.
“Try again, Slut, and this time, don’t go down so fast, okay?”
“Yes, ma’am.” I position myself to face the dripping, bobbing cock, a trail of precum reaching out to the floor.
“Oh, lick that up Slut before you make a mess on the nice clean floor.” I open my mouth and begin sucking up the cum before I open my mouth and slowly lower myself onto the cock.
“Very good, very, very good Slut. Now begin bobbing your head up and down, just so the cock is hitting the back of your throat.” I follow the commands. My eyes watering as the cock bounces around in my mouth. “No, no, no- not like that. It has to be quick and smooth like this…”
For a second, I thought Ms. Pascoe was about to relieve me and demonstrate how I should be sucking a cock and end my torture. But then I feel two hands grab me by the side of the head, and begin forcing my head back and forth, up and down the big, black cock. Her pace is much quicker, and the cock is hitting my throat very hard, making me gag, but Ms. Pascoe doesn’t release her firm grip, instead forcing the cock deep down the throat. She then pulls me back, allowing the cock out of my moment, letting me desperately gasp for air, before pushing me back down the length of the cock, the cock going deep down my throat. Back and forth, I am pulled in a cycle of gagging and gasping. Suddenly, I hear John give a very loud moan and I feel the head of his cock engorge. With this, Ms. Pascoe pushes me down onto the cock as far as it will go, John’s short, curly pubes scratching my nose before I feel streams of hot cum hit and slide down my throat. Ms. Pascoe keeps me pressed right down, making me swallow down every last drop of John’s cum before finally releasing her grip. I feel the thick, warm goo make its way down my throat, I have never felt worse or lowly- cum dripping from my face, dressed like a girl, as three people look down at me on my knees with beaming faces.
“Smile, Slut!” Natalie says, shoving the camera in my face. I don’t know what to do other than follow her command, and I give a very weak smile as I hear the click of the camera. I wish the ground would just swallow me whole right now.
“Very good, Slut! That was excellent for a first time!” Ms. Pascoe says, patting me on the head like a well behaved pet. “As a Sissy still with their training butt plug, it is very, very important that you take your cocksucking training seriously. But I have to say, you’ve taken to it like a duck in water! Now lick John clean and tidy him up.”
Still gasping for air, I begin to lick the remaining cum off John’s long, softening cock.
“Babe, that was the best blowjob I’ve ever had. From now on, Roomie, I want you to sleep in my bed with me. I want to wake-up every morning with my Morning Wood in your mouth. Got it? You’re going to suck me off every morning and every night. It’ll be the first and last thing you do everyday. Got it, Slut?”
With my mouth still wrapped around John’s cock, all I can do is give a muffled ‘Yes, sir’ as I feel tears rolling down my cheeks.
Chapter 5: Ex Girlfriend
Something wakes me up from my sleep. At first I think it’s John’s huge, erect cock pushing on my back, as he sleeps with his large muscular arms wrapped around me. Or was it the familiar aching pain of my cold, metal butt plug stretching my ass hole? But then I hear the girl’s shrieking again, and I realize it is her who has woke me up. I open up my eyes wide and scared to see my girlfriend standing over me with a furious look on her face.
“It’s true! I can’t believe it’s true! How could you do this to me!?”
“Take this outside you two, I’m trying to sleep.” John mumbles, his eyes still closed, as he pushes me out of the small, single bed.
I fall in a heap at Alex’s feet wearing pink cotton panties with teddy bears on them with a matching short pink camisole that reveals my midriff and wide hips.
“Oh my God, look at what you’re wearing! I absolutely can not believe this!! Did you ever think how this looks for me!?”
“Outside you two!” The large, black man says in an angrier tone.
With this, Alex grabs me by my hand, forcing me to my feet, and drags me into the Living Room of my dorm. “I can’t believe this! I just can’t believe it! You’re throwing away your whole life so you can be the Sadler Sissy?”
“It’s not me, Alex, it’s-“
“What, you’re going to say it’s not your fault? You were born a Sissy or something and you can’t help it?”
“No, it’s not like that at all!” I can’t help but feel pathetic as I look at Alex’s short denim skirt and a neat light blue shirt that showed off her sexy curves. It made quite a contrast to my prepubescent girls sleepwear.
“Well, it’s what all the girls are saying! Natalie told me she found you dressing yourself in the frilliest, pink dress she had ever seen! All I needed was to see it for myself, and it looks like I’ve found it.” she says, with a disgusted look on her face as she looks me up and down.
“Please, Alex, don’t do this! They are making me do it! Wingett and his cronies! I wanted to tell you, I really did, but I was just way too embarrassed! But now that you know, you have to help me!”
“Forget it. I’ve seen the pictures. Your smiling face, covered in cum and make-up. I thought Natalie had faked them, as some kind of horrible joke. But now- now I see she was telling the truth like a true friend. Not like you, asshole.”
“But- but- but she’s lying! She told me to smile!”
“Oh yeah, she told you to smile. I’ve had enough of you and your bullshit. If you want to play dress-up, that’s fine. But no more doing it in hiding, I want everyone to know what a stupid Sissy Slut you are!”
“I’m going to show the entire football team what you’re doing, you disgusting freak. Training starts in two hours, well in two hours and five minutes everyone is going to know about you and your little secret.”
“Please, don’t show them the pictures! It will ruin me! I’m a man, they are making me do all of this!”
“Sluuut, I’ve got Morning Wood! Why aren’t your big, luscious lips wrapped around my cock!?” I hear John yell from his bedroom.
I could have died, and Alex just looks at me with a bemused look. “Oh, you’re a real man alright.” she says with a laugh. “Well, go ahead, wouldn’t want to keep your boyfriend waiting.” she says, grabbing my hand and leading me back to the bedroom.
I simply lower my head and let myself be lead. “Yes, Sir, I’ll be right there, Sir.”
I scurry back to Jon, his huge erection forming a tent in the bed sheets.
“Who is this bitch waking me up at this hour?”
“This is Alex, my girlfriend.”
“Ex girlfriend.” Alex quickly points out, crushing my feelings as she gives me the evil eye.
“I was wondering how a Sissy like you could keep a girlfriend.”
“Well, I wasn’t sure he was sissy until right now. So what’s your two’s deal? You boyfriends or something?” Alex says putting a hand on her hip, brushing her long, black hair out her face with her other hand.
“I’m one of the Sadler Studs. They’ve got me on a bunch of drugs that pretty much make me horny all the time. They gave me the Sissy here as a kind of compromise or whatever.” Jon explains before taking a much more direct tone with me. “What are you waiting for, Slut, get to work!”
I gulp, the idea of sucking another man’s cock in front of my girlfriend, my ex girlfriend, sounded like a nightmare. I rip off the sheets and get in between the large, black man’s muscular legs. A few days ago, the image of the large black cock bobbing up and down in my face was the most terrifying thing I have ever seen, now it was just a regular feature of my day, and sucking it off is just one of a hundred humiliating tasks I have to do everyday. I spit on the large, black cock and wrap my fingers around it, my fingers barely able to wrap around it. Giving a few jerks up and down, I quickly put the huge cock in my mouth and begin lowering my head up and down, trying to get him to cum as soon as possible so I can end this new humiliation as quick as possible.
“Slow down, Slut. What’s the rush?” Jon moans as he grabs my hair, forcing my head up and down his cock at a much slower pace. I want to scream at him, to bite down on this cock as hard as I can, but I just relax my muscles as his strong hands force me up and down his cock. All I can do is give out muffled moans and whimpers as my cocksucking training kicks in and I begin rolling my tongue around the underside of the massive black cock in my mouth.
“Wow, he sucks cock like a whore!”
“Yeah, Slut has been in-training all week. Mine, dildos, random strangers. She’s crazy, this girl.” I feel the tears well up again when I remember all the cocks that have been in my mouth in the last seven days, Ms. Pascoe’s glowing face when she would bring another boy into my room for me to please.
I can see in the corner of my eye Alex’s red and furious face after she hears what I’ve been up to. “Oh yeah, is that right? I think I’m going to have to teach her a lesson right now.”
I feel the head of Jon’s big cock engorge, his hands pushing me right down his cock so my nose is in his pubes as he finally spray a stream of thick cum onto the back of my throat. I obediently swallow it down , closing my eyes, trying to ignore my lover standing over me with crossed arms and tapping her foot patiently waiting for me to finish up cleaning up Jon’s juices. I release the cock from my mouth with a pop, before slurping up the rest of the spit and cum before slipping his cock back into his boxer shorts.
“You’re getting better, Slut. Keep it up.” he says turning on to his side, closing his eyes, trying to catch a few more minutes sleep before he has to get up.
“Slut was it? Okay, you’re coming with me.”
My mouth fell open. What was she going to do!? “I can’t, I have an-” I was about to tell her about my daily appointment with Nurse Rebecca, but I could see by her expression she wasn’t interested in hearing excuses and I realized I didn’t want to tell her what happened in those appointments. And besides, maybe if I didn’t show up, they would come looking for me and save me from this mess. “Can I change my clothes?”
“No, I’ve got some great outfits for you at my dorm, you can change there.”
“What you are wearing is fine, just grab a bathrobe and some heels and we’ll be on our way.” she says, the threatening tone in her voice more than obvious.
“As long as you don’t tell anyone about my… you know.” I say desperately, motioning to my womanly body and cute pink panties, showing just a hint of the very realistic pussy the thin material was covering. “This is all meant to be secret! I don’t know what they would do if you let everyone find out about this.”
“Oh, that’s right, you are being forced into all of this.” Alex says skeptically, with a big smile on her face. “C’mon, go get your things and come with me.” she says holding her hand out expectantly.
God, she thought I wanted to do all this? And what would Ms. Pascoe do if Alex broke the big secret? “Don’t show those pictures to the team, please. I’ll do anything you say, just don’t tell anyone, okay?” I hated how sad and pathetic everything I said was these days, but what choice did I have? I knew if she walked out of here as angry as she was, she would tell all my friends on the soccer team in a heartbeat. I had to convince her that I was being forced into this. Who knows, she might actually understand and take sympathy on me.
“Don’t make me repeat myself, Sissy. Grab a robe and something to put on your feet right now and then take my hand. Got it!?” Alex sounded like a drill sergeant giving me orders.
I just gulped, scampered to the closet, and tried to ignore Alex’s eyes fixed on my new, sexy ass as I retrieved the few items. I hoped to God my plug wasn’t showing through my panties. I’d hate to have to explain that to her this morning as well. I came back wearing the short, pink, silk robe barely covered my butt, and my most modest set of heels, pink with only a three inch heel.
Alex looks me up and down with a disgusted look on her face as I shift self-consciously in my heels in front of my girlfriend. Ex girlfriend.
“Okay, let’s go.”
“But- ahh, Alex, you know I have some wigs, too. Maybe-“
“A wig!? Why am I surprised? Okay, I’ll go pick out one. I’m sure your team mates will appreciate it.”Alex says with a wink, as she spots the three wigs sitting on my dressing table amongst the assortment of make-ups sprawled across it. “But we’ll save the wig for later. I want to make sure everyone knows who is mincing through the school in high heels and pink panties.”
I almost cry when I hear these last words. The idea to hide my identity with a wig blew up in my face, and now I’m about to be trotted through the school wearing girls underwear, high heels and a too-short, silk bathrobe. My secret is finally going to well and truly revealed. I looked at Alex as she carefully picked up the wig with the tresses of long, red hair before I realize that my panties were quite visible, the short robe not quite closed properly. I quickly pull it shut, blushing slightly despite Alex seeing me in only panties and camisole a moment earlier.
“Aww, aren’t you a blushing beauty? That’s cute. C’mon, we’ve got to get ready for your big coming out party.” Alex says, a smile finally coming to her face as she walks back to me the red wig in her hand, holding out her other for me to take.
“Please, Alex, I’m begging you, don’t do this!”
Alex’s face completely changes, her expression turning stern and angry. “Do you know how humiliating it is to find out my boyfriend’s turned sissy. Natalie is already telling everyone. It’s going to ruin my life! No, I have to show to everybody that this,” she says motioning to my body, my high heels and short, pink robe, “has nothing to do with me.”
“But- but-” Alex ignores my pleas, her expression switching back to cheerful as she simply grabs my hands and starts pulling me out the front door.
I pull back, absolutely terrified at the idea of being seen like this, let alone by my old friends and team mates on the soccer team. What the hell would they think? I expected to be able to resist Alex’s pulling, the small girl only slightly taller than myself. But she gives a mighty heave and I stumble on my high heels out the door, where I promptly fall over, my robe flying over, my pink panties fully revealed to the three male students in the hall, all looking on with open mouths and shocked faces.
I am so incredibly embarrassed! It’s one thing for professional Mistresses to see the pink panties with the cute teddy bears on them, but a complete other for an acquaintance to see!
Alex is laughing heartily as she pulls the door shut, the click of the lock making me realize I had no escape. As quick as I can, I pick myself up from the floor, pull my silk robe shut and hide my body the best I can behind Alex.
“Don’t be shy, honey. You weren’t shy sucking a big cock in front of your girlfriend, I don’t know why you’re so shy about flashing your pretty panties.” Alex said loud enough that the whole hall could hear.
I felt my face burn with embarrassment. Of course, she was right, I don’t know why I found this so humiliating, but the fact of the matter is, I did. I hated everyone knowing what I had become- a panty wearing sissy.
“Please, can we just get this over with?” my quiet begging makes Alex spin around and grab my face with her hand, making my lips turn into a ditzy pout.
“You listen to me, faggot, I call the shots! Not you! Got that!?”
“Yes, ma’am.” I manage to mumble out with Alex’s hand mushing my face.
“Good, now let’s go.” Alex says grabbing my hand as she begins stomping down the hall in between the male students who are left stunned as they ogle the panty-wearing sissy scurrying behind her.
Sadler was a huge school, filled with crowded buildings and busy pathways. I tried to concentrate on my feet, which wasn’t that difficult as I struggle to keep up with Alex as she dragged me along in my high heels, weaving in between the many students on the brisk, Autumn morning. While it wasn’t uncommon at all to see someone walking around in just their sleepwear, it is not often you seen one of the school’s soccer players walking around in a short pink robe, smooth, hair-free legs and high heels. I couldn’t help but tug my robe closed every five seconds, but it didn’t help stop the feeling that everyone could see the teddy bears on my pink panties.
“Kev? Kev, is that you?”
“Oh hey, Jim.” I say, my face somehow finding a deeper shade of red as I recognize one of the guys I sit with in my classes.
“What are you wearing?!”
“Oh, I couldn’t find my robe, so I borrowed my girlfriends.”
“Ex girlfriend.” Alex points out as she does not break stride to chat.
“But why the high heels?”
“Ahh…” Not being able to think of any possible reason why I’d be wearing high heels as I was dragged through the busy school, I just ignored the question and turned away from his shocked face and followed Alex as she led me down the walkway.
I was so relieved when we approached Alex’s dormitory, which thankfully, is not too far away from my own dormitory. This feeling was changed when the shocked and bemused faces I saw outside were replaced with apathy. They didn’t even recognize me as a boy in girls clothing! It was obvious that the girls thought it natural for the girl with a boyish haircut to be walking around the halls of a girls dormitory. I almost felt like crying.
“Here we are, honey.” Alex says as she opens the door to her room.
It is neat and tidy, as to be expected from a girl who keeps herself constantly neat and tidy, her small but still shapely figure always draped in the most fashionable clothes. She never had a hair out of place, her face made up immaculately. I step in to her room, relieved to be inside, away from peoples prying eyes, even if they did think that nothing was unusual.
“Who’s this?” I spin around scared to see Alex’s chubby, bespectacled roommate, Martha.
“Don’t be silly, you’ve met Kevin before.”
Martha puts a hand over her gasping mouth in shock. “That’s Kevin!? What happened?”
“Kevin has decided that he is a Sissy and can no longer keep living a lie like he was.”
“You know, a boy who wants to be a girl. I just caught him sucking the cock of that sexy, black Stud Jon.”
“And check this out!” with that, Alex grabs my robe and rips it off my body in one quick motion, revealing my pink panties and camisole. I want to die as I desperately cover my body from Martha’s eyes which are currently looking at me up and down.
“Well, ahh, well I certainly respect your choice, and I appreciate the courage it must take to make that kind of decision, Kevin. Oh, I’m sorry, what should I call you now?”
“Well, Jon was calling him Slut, but I think he said he wants to be called Kelly.”
“Well, you’re being very brave, Kelly. “
On one level, it felt kind of nice to get some sort of support. I was getting very tired of beautiful women pointing and laughing at my emasculated body. But at the same time, I was revolted that people were believing that I actually wanted to do this. Why did people so readily believe that I would want to change myself to a girl? I’m short, yes, but I always thought of myself as a man’s man.
“We’ve just come to pick out a new, sexy outfit for Kelly. I think her boyfriend might have some wild fantasies.” she says in a playful tone, giving me a broad smile and a little wink.
“Oh, that’s nice.” Martha says with a weak smile, making me blush and look at the floor in shame. “Well, um, I think I’ll go. I have an early class.”
“Suit yourself, but we’re going to have lots of girly fun.”
“No, you two enjoy yourself, I have to go.”
I can’t help but notice as Martha hurries through the door that she has no books or pens and according to the clock on the wall to see it’s just past eight o’clock in the morning, too early for any classes to be on. This is just the time I would usual be strung up my Nurse Rebecca to get my daily enema and scrubbing down in that feminine goop that leaves my skin hairless and smooth and supple like a teenage girls. I hated to say it, but I was hoping Ms. Pascoe was going to burst through Alex’s door to find out where I was and save me Alex’s demented plans of ‘revenge’.
“I’m glad she’s gone. She is way too understanding to know how to handle a Sissy like you properly. Stay here why I go get your outfit.” I just shuffle nervously in my camisole and panties. As I listen to Alex shuffle through her closet, I look down at myself and cringe when I notice my new nipples are trying to poke two little holes through my pink top. “Ah, here they are.”
I see Alex return holding two outfits on coat-hangers. One is a sexy schoolgirl outfit, very short white blouse, and very, very short red and black tartan skirt. The other is a blue, white and gold cheerleader outfit, with a sleeveless top and a skirt that barely looks like it would cover my butt. I recognize the outfits from the sexy games we used to play in the bedroom with each other, and I know from experience, neither outfit covers very much flesh. And now she wants me to go outside in this outfit? She wants me to go to soccer training in a costume meant for foreplay!?
“Okay, you have two options. Which one do you want to wear for the boys?”
“Oh, please don’t make me choose…”
“No, no, no, this is something a girl must learn, how to dress to please a man. The only reason I bought these outfits is to make you happy. We’ll now you’re going to learn to give the same pleasure. Now choose!”
I shuffled nervously in my high heels as I saw the threatening look in her eyes. But I couldn’t do it, I couldn’t wear one of these slutty outfits in front of all my friends and team mates. Who knows what else she has planned to do to me.
“Alex, please, listen to me, your lover. They are making me do this! I hate every moment of it! I swear!” I beg and whine.
“What are you talking about? I saw you suck a cock thirty minutes ago! I didn’t see anyone making you do that! And what about the pictures of your smiling face covered in cum? They made you smile?”
“Fine, you don’t believe me, okay, but you have no right to do this to me. I’m leaving.” With that, I pick up the short silk robe and turn to the door, leaving Alex standing speechless holding the two sexy outfits. “Mmpf!”
I hit the ground with a grunt as Alex tackles and drags me to the floor.
“You’re not going anywhere!”
“Get off me you crazy bitch!” I scream, squirming and kicking my legs, trying to get off me, but using all my strength, I can barely make the small girl move a muscle. “Help! Someone help me!” I scream desperately, hating that I have to call for help to get a call off me.
“Shut up, whore!” she says, slapping her hand over my mouth before being giving me a hard knee to the balls.
The pain is so bad that I see white lights in my vision for a moment, and I can’t help but grab at my crotch and roll around on the floor in pain. Alex sits up, straddling a thigh on each side of my body, before gritting her teeth and using her skinny arms to tear my panties along the hip, ripping them painfully off my body. I gasp as I feel the thin cotton material whisked off my body in a painful manner, allowing Alex a moment to shove the torn up panties in my mouth.
“Mmmph!!” I try to protest, to scream for help, but the cotton panties, slightly smelling of my own frustrated body’s precum, means all I can make is a muffled moan.
“You keep those panties in your mouth, Missy, or I’m going to make this really embarrassing for you!” I push and kick, and I finally manage to spit the panties out of my mouth.
“Get off me! Please, get off!” I beg, but Alex just grabs me by the wrists and forces them back on the ground above my head.
“Oh, you are being a very naughty Sissy!”
Alex, holding my wrists, gets up off my body, allowing me to squirm like mad for a moment, before she repositions herself, before plonking down on my face, holding my upper arms down with her knees. Her ass is now smothering my face! The position has my nose digging into her pussy hidden behind her white cotton panties, while my mouth is practically on my ex girlfriends asshole. I can barely breathe, and I can’t move my arms or upper body at all as I am pinned down by her knees, while my legs flail about uselessly, unable to kick Alex off me.
As I squirm, I feel my nose invade her pussy, and I can smell her juices beginning to flow. “Lick my asshole, Slut.” she moans in lust as she reaches down with her now free hands to move her crisp cotton panties out of the way. I have no choice but to comply, my arms, face and chest now held down by her entire body weight, as little as that was. I felt the tears come to my eyes as I feel truly helpless and hopeless as my girlfriend lifts her denim skirt up over her hips and begins to buck up and down on my face. My ex girlfriend begins to buck up and down on my face. “What did I just say? Lick you fucking whore!”
I tentatively poke out my tongue, tasting the awful, horrible taste of Alex’s asshole. My tongue is soon swirling in circles around her tight sphincter. For a moment, I consider biting down on her private parts until she got off me, but then a vision of the sort of punishment I would get for that, from Alex and Ms. Pascoe has me soon sucking and licking on her tight hole like it was an ice cream.
“Poke out your tongue as far as you can!” The tears are flowing freely now as I follow Alex’s order, and stick my tongue out as far as possible. I feel Alex lower herself up and down, my tongue invading her asshole. She is fucking her asshole with my tongue!
Alex twists her body, still moaning in pleasure, so she can rip off my pink camisole, in several, straining efforts using both her hands. I feel so stupid, now lying naked on the floor, my so-called ‘lover’ sitting on my face, making me fuck her asshole with my tongue.
“Look at your body. Natalie told me you were wearing some god damn thing to make you look like a girl, but I just can’t believe how much like a girl you look like.” Alex manages to get out between her moans of pleasure, as she reaches down and begins stroking the folds of my prosthetic pussy.
My cock was trapped in a chastity cage, hidden under a layer of extremely tight rubber, but the light fondling of my locked-up cock made my horny body go wild, and I was soon pressing my crotch into the palm of my girlfriend.
“Yes, I can still feel you down there when I really press in there.” she moans, as she digs two fingers deep in between the folds of my pussy, making me give a loud groan, making me buck my hips wildly. “Oh, and I thought you didn’t like this?” I have no chance to protest, no chance to say I hadn’t been touched down there for weeks othen than with a course scrubbing brush, let alone been allowed to cum. But all I can do is stick out my tongue, while Alex rubs her pussy and asshole up and down my face and moan and squirm in pleasure. Soon, Alex’s juices are freely flowing over my face. ‘I’m glad, I bet it will hide my tears’, I think to myself.
“What the fuck is this!? These titties aren’t fake! You have real tits!” Alex screams, groping my new breast hard, making me give a muffled squeal. “You’ve been on hormones, haven’t you, you fucking ass whore!” Alex begins grinding her asshole in to my face, pinching and twisting my nipples hard, leaving me squirming and squealing underneath her, barely able to breathe, but screaming anyway because I am in so much pain.
“Lick, you whore, keep licking my asshole.” she screams between her moans, as she begins slapping my pussy, sending waves of pain and pleasure rocking through my body as I do my best to stick my tongue up Alex’s hole. “How long have you been on pills, you prick!?” she screams, grinding her pussy and ass up and down my face, her knees effectively pinning me down as she again reaches down to fondle my pussy, making me moan in pleasure..
Alex’s own moaning gets louder and louder as she begins to grind my face much faster, and she bites down on her finger to quieten herself down. Streams of juice are flowing from her pussy, ending up all over my face, before she finally orgasms, pressing her mound hard down on my mouth, so I am forced to suck down the flow of pussy juice..
“Oh my God, that was fantastic!” she says huskily, panting heavily. “Who knew dominating a guy could get me so hot. I could get used to this.”I could not really respond, as she had leaned back on my face, smothering me once again. All I cared about was the hand that disappeared from my crotch, leaving my whole body on edge and begging for release.
Alex reaches down to grab my torn pink camisole top and begins tying my wrists together with it. I strain to resist, but Alex only allows enough movement to inch my wrists together. “I’m going to make you pay for this. You’ve known for ages you’re a cocksucking Sissy, but you dated me anyway, just to embarrass me! Well we’re going to see who’s going to be embarrassed now!” She wraps my wrists together and ties them in a tight knot, leaving a tail of left over pink material. She finally gets off my face and arms, making me gasp for air, groaning in pain as the blood rushes back to my arms, before being tugged to my feet, Alex using the tail of material as an impromptu leash.
“Oh, look at you!” she says, staring intently at my crotch. I know what she’s talking about without even looking as I feel trickles of my own precum rolling down my inner thighs, leaking out from my soaked ‘pussy’. “Oh, you look so much like a real girl right now I can’t believe it! I’m going to leave you like that so the boys can see how wet and willing you are!” she says, with a huge smile on her face. I take a breath, again about to scream for help, to save me from this crazed woman, but I find my torn up pink panties very quickly shoved in my mouth, as if Alex was just waiting for me to scream. “Now, now, Sissy haven’t you learned you cannot do anything about this? If you were a real man, maybe, but not now, I’m too strong for you. You keep those panties there, Missy, or I’ll think up something else horrible for you to do.”
My face is a bright shade of red as I stand naked and tied up, gagged with my own panties, my face covered in Alex’s juices, leaking my own juices down my thighs like the slut they were all calling me. The thought I had been beat up and dominated by this cute looking girl in front of me is still lingering in my mind, just like the taste of her asshole on my tongue. But mostly my face was red from my sheer horniness, my cock is straining against its cage, making me cringe with a familiar pain, and soon the only thing going running through my mind is the hope of sexual release. I barely process that Alex is leading me to the bathroom, talking and laughing the whole way, before tying my wrists up on the rail of the shower curtain, leaving my hands way above my head and my shameful body totally on display for my small, smiling girlfriend.
“Time to get you ready for your big date, sweetie. Now tell me again, what do you choose?” she says as she holds up the cheerleader and school girl outfits up for my inspection, before using a hand to roughly remove the panties from my mouth.
“The cheerleader outfit, ma’am.” I say foggily.
“Oh, good choice. Why’s that?”
“Because- because- because it makes me look good for the boys.” I say red faced.
“Good answer!” Alex laughs, shoving the panties back in my mouth roughly. “And I just know the boys will like these.” Alex holds up the almost transparent, fluorescent blue thong with lace flowers in the embroidery up to my face. I recognize them as my favorite lingerie, the panties I made Alex wear all the time. ‘I just like them, honey, they are so cute and sexy, and barely leave anything to the imagination!’, that’s what I used to say. I just look away from Alex, not wanting to see me cry as she leans down and slips my feet through the panties, before sliding the soft, silky material up my smooth legs, tucking them in place, so the thong is sitting up high on my ass.
“Wow, has anyone told you how great your butt looks now?”
I nod my head pathetically, almost instinctively, trying my utmost to imagine I was somewhere else. Alex laughs heartily at my response.
She leans down again, this time guiding my feet through the short skirt. She tugs the skirt in to place and buttons it up, again making sure that the skirt was sitting high on my hips, ensuring that it only barely covered my ass cheeks.
“Oh my God, so sexy! I’ll be right back!” Alex returns holding a pair of stockings, and at first I think she is going to put them on me, but I find she quickly wraps them around my ankles a few times before tying a tight knot. “I just have to untie your hands, so I can put on your top and make-up.” I groan behind my panties when I hear this.
Alex unties my wrists from the shower curtain before she turns to sort through the various items she had prepared in the bathroom. To my surprise, she turns around holding a light blue bra that matches the panties I’m wearing.
“I know, I know, this is my bra, how will you ever fill it out?” Alex asks in an ironic, caring tone as she puts the bra on me, clasping it up at the back before tightening the straps so it fits my small frame. “But that’s okay, I hear lots of young girls just use cotton balls and tissue! I’m sure the boys won’t notice!”
A heap of cotton wadding and tissue paper is shoved in to the cups of the bra, making them look very big, filling out the D-Cup bra easily. I am still looking at my chest, squirming as I feel the unfamiliar, tight sensation of the bra straps on my shoulders, all a little dumbstruck. When Alex slips the sleeveless blue, white and gold cheerleader top over my head, guiding my arms through like she was dressing a toddler, the top short enough to leave my midriff on display, I notice that it is impossible to tell I don’t have real breasts. It looks like I have two large breasts under this cheerleader uniform!
I am in a state of panic when I feel Alex brush my hair back, before placing the red haired wig on my head. After a few more strokes with the hairbrush, she takes a step back and soaks in the image of me.
“I can’t believe it, I just can’t believe it. if someone had told me a week ago you were my boyfriend Kevin, I wouldn’t believe them!” I just groan behind my pantie gag, tears beginning to roll down my cheeks. “Oh, you’re crying! I can’t believe you, you pathetic little faggot, beat-up and crying at the hands of a girl.”
Alex walks up to my and slaps me across my face. “Well no more crying! We can’t have crying for this next part!” she says as she grabs a few tissues to wipe the pussy juice and tears from my face. “If you move a muscle while I do this, if I seen one tear, I’m going to knee you in the balls again, understand? I might just spend the whole day torturing your balls, how does that sound, Sissy?” I shake my head vehemently as I hear her threat spelled out to me. “Good, now sit down and be still!”
I sit in the tiny seat in front of the large mirror in her bathroom, opening my mouth slightly to make it easier for Alex to take the panties back out of my mouth. She grabs her huge make-up bag sitting on the counter, and begins shuffling through the seemingly hundreds of vials and little glass bottles, putting an assortment on the table in front of me. In only a few minutes, Alex’s quick hands turn my face into that of a beautiful teenage girl. My lips were painted a glossy orange-red color, while the rest of my face was left natural looking, but still clearly wearing make-up. She even turned my eyebrows red using an eyeliner pencil. I couldn’t believe the image staring back from the mirror. Long red hair, beautiful, made-up face, sexy toned stomach on display, large breasts bulging out proudly behind my cute, crisp cheerleader sweater; the boys were going to eat me up.
Alex squeals in delight, clapping her hands. “Oh, you look so sexy! No one is going to believe you are Kevin! Until I rip that sexy wig off, and then won’t the boys get a surprise!?” she says, laughing wildly now. I can barely believe her plans, I am so shocked! Alex stoops down and unties my feet, as I sit dumbfounded, realizing now that my life will never be the same after today. No more soccer, no more friends…
Alex grabs my hand and begins tugging me to the door, taking me to my nightmare. “Oh, I forgot one thing!” she says, guiding me back to the bathroom, still holding my hand. “Here, these should be your size.” she says smiling, handing me a pair of, what looks like, six inch black high heels. “We call these ‘fuck me’ heels. You only wear them when you are on the prowl.” she says with a wink.
I gulp when I see the heels. “I- I am not used to wearing such high heels-“
“Well the only way you are going to get better is through practice. Now, put them on.”
I should do something, use them as a weapon and get out of this horrible situation. But my body just takes the heels, and leans down to put them on. As I do so, I feel the very short skirt ride up, and I feel the cool morning air on my naked ass. I feel the tears coming back as I realize almost my whole ass is showing. I look up at Alex, trying to find some hint of sympathy or compassion, but all I see is her face with a beaming smile, eyes glued on my ass, shaking her head in disbelief.
“You really do make one sexy girl. Come on, let’s go or we’ll be late for soccer training!” Alex says grabbing my hand before leading us out the front door, as I teeter behind her on my ‘fuck me’ high heels.
Chapter 6: Crescendo
I teeter along the uneven path, one hand being held by Alex, the other desperately holding down the hem of my unbelievably short skirt, surely flashing my bright, blue panties to every student I walked past. It was almost nine in the morning now, and every walkway, every bench, every space, was taken up by a Sadler student; every single one stopping and turning to get another look at the redhead in the barely-there outfit. I shivered in shame with every shocked look and whispered comment. The skirt was not much more than a cotton belt that barely hid my bright blue-semi transparent thong, completely showing off my legs and toned stomach, Alex’s bra barely containing the mountain of wadding she had put in the cups under the skimpy, sleeveless cheerleader top.
“Alex, nothing is going to happen, you can’t make me do anything to those boys.” I whisper, trying to keep the conversation quiet as we squeezed our way through students as we travelled down the path.
“I’m serious, you can’t make me and I don’t want to do it.”
“So when I drag you in to the locker room you’re simply going to explain that your ex-girlfriend beat you up and made you dress like a sexy cheerleader?”
“Quiet! People are listening!”
“And what if I beat you up again, and show them all your budding bosoms? How are you going to explain that? I made you take pills for months, did I?”
“It’s not like that!”
“No need to explain it to me, Sissy,” she says , drawing the attention of everyone within earshot, my cheeks flushing red as I scurry faster trying to get away from all the probing eyes, soaking in my naked legs and sexy body, “you’ll have to explain it to your team mates.”
“Please, I’m begging you, this is my life!”
“You’re life is as a Sissy now, so you better start enjoying it!” I whimper with the finality of her statement and her glaring eyes, knowing that all chance of this girl helping me was gone forever.
“Please… don’t do this…”
“Look, Sissy, you made this decision a long time ago! Consider this… just a push out of the closet.” she says with a laugh as I do my best not to begin crying in front of the crowd that has assembled around me.
I feel a cold burst of wind and the back of my skirt hit the small of my back, and I feel the cold, crisp morning air on my naked butt cheeks and my wet, clammy panties. The crowd produces am audible gasp as they stare in disbelief at my pert, naked butt, and my wet bright blue panties. Alex laughs hysterically as I desperately tug down on my skirt, tears welling up in my eyes as my cheeks burn bright red. I hear the crowd break out in a chatter, all talking about my dripping wet panties, unbeknownst to them that it was my tortured and unsatisfied cock’s precum. Alex just tugs me along, and I thankfully scurry behind her, doing my best to keep up in the extremely high heels while holding my skirt down so hard that I’m slightly worried the material might rip.
The path started to clear up as we began approaching the more isolated large, modern gymnasium, a large, emerald green soccer field hiding behind the steel building. I instinctively beginning tugging back on Alex’s hand, forgetting for a moment the scene I was making, a dozen or so students still watching with mouths wide open in shock from behind us. I tried to control my staggered breathing and force myself to follow Alex to the quiet Gymnasium.
She stops just as we approach the large, double doors, and looks at her small gold watch before turning to me. “Looks like we have about five minutes, so let me tell you what you’ve got to do.”
“I’m not going to do it, I’m not doing anything to those boys.”
“Ah huh, I’m sure. You’re going to do it, or I’m going to take my outfit back, and send you trotting back to the other side of the school naked. I might let you keep those sexy heels.” Alex says with a wicked laugh. “I guess you could say your options are humiliate yourself in front of a dozen of your friends, or humiliate yourself in front of the whole school. So what do you choose?”
“I choose to get away from you, you crazy bitch!” I don’t know what came over me, maybe the remnants of the masculine side these bitches were trying to strangle out of me, but regardless, I find myself screaming at Alex angrily, shoving her, before turning to walk away.
I just here an aggravated sigh, before something big and strong wraps itself around my wrist and pulls me down, making me topple over easily in my high heels. To my surprise, Alex catches me before I fall over completely, grabbing me by the waist to holding me up, but all too late do I realize what she has done. She has me by the waist in one arm, my body resting on her hip bent over at the waist, the bottom of my ass cheeks on display from under my short skirt. ‘She has pulled me over she can spank me!’ I think terrified as I hear Alex spit on her hand. I cry “No!” at the last second, but I hear the loud slap of flesh on flesh before I feel the burning stinging pain emanating from my ass. One slap, two slaps more and it feels like my ass is on fire. I begin squirming like mad, trying to break from her grip, as I see people begin to approach us through my teary eyes.
“Please, not here! Gawd, I’ll do anything, just please don’t spank me here!?” I say desperately, not being able to imagine anything worse then been given a spanking by my ex girlfriend in public, a crowd sure to gather any moment now.
“Aaaanything?” Alex says, bringing down one more cruel spank as I see the strangers make surprised faces as they approach the girl being bent over and spanked in a sexy cheerleader uniform.
“Yes! Yes! Anything!” I squeal through my tears and cries of anguish as a few strangers wander closer, not sure whether they should be aroused or whether they should help the girl.
“Good girl! I didn’t want your ass too red for the boys anyway.” Alex says with an evil smile and a wink to the teenage boys who had just arrived before she finally pushes me through the swinging doors, the onlookers giving a disappointed groan. “Don’t worry, she just loves showing off her body in public, I’m sure you’ll get to see her again real soon.” she says laughing, the handful of boys just left scratching their head, wandering what the hell just happened.
As soon as I am away from the terrible prying eyes of the strangers outside, I immediately begin rubbing my sore behind under my short skirt and sniffling back my tears, not believing how desperate and pathetic I sounded in front of all those people. I had never felt more ashamed in my life, as I thought about the countless amount of people who had just seen me dressed like a red-headed, cheerleading slut.
“That was so much fun!” Alex sings from behind me as she lifts up my short skirt to have a closer inspection of my reddening butt cheeks.
“Are you crazy!? You just can’t spank me in front of the whole school like that!” I whine, whirling around to hide my butt before wiping the tears from my face.
“Oh, please, grow up! Hardly anyone saw the spanking, and besides, everyone has seen a girls butt before!”
“But I’m not a girl!”
Alex just gives a skeptical look, motioning to my body with her eyes. “Yeah, why don’t you ask the people who just saw your butt what they think” Alex says with a cackle. “Now as I was saying before you rudely interrupted me, was that I want you to do a dance for the boys. Kind of like a cheerleader, but more like a cheap stripper.”
“A stripper!?” I cry, my words echoing through the corridors of the large gym.
“Yes, I want you to do a strip tease, just like one of those sluts at a cheap nightclub. Doesn’t that sound just so fun?!”
“There’s no way I’m doing that! You’re crazier than I thought!”
Alex bites her lip and looks at me with her big eyes before saying “I tell you what, you do this little dance for me, and I won’t rip off your wig and reveal your secret.”
“But I thought the whole point-“
“I thought I wanted to reveal your secret, but I guess what I really wanted is to watch you suffer. You really hurt me, you know? I just want some payback. But I can see you’ve suffered a lot. So, I’ll let you off easy, you be a cheap stripper for me and the team and we’ll call it even.” Alex says, her tone of voice showing how genuinely hurt she was that I ‘betrayed’ her, but not hiding her malicious intent either.
I nod my head pathetically. I was coming to realize over the last few weeks that girls can get immense satisfaction out of making a man squirm under their thumb and Alex is definitely no exception. “But- but-“
“Do you- do you think the team will- will- think I’m a girl?” I nervously splutter out, making Alex laugh.
“I’m your girlfriend, I’ve seen and touched all your whole body, and I can say, this morning, I barely recognize you. You look more like the photos of your younger sister you showed me!” Alex says, struggling to contain the huge smile trying to break out across her lips. I just groan with disgust and disappointment to the frank reply to my question.
It didn’t matter how hard I tried, I seemingly could not escape Alex’s grasp. I couldn’t beat her up, and if I tried to run away, she’d just catch me and make things worse. I’m sure the wig protecting my identity would be first thing to go. Then it’d probably be the barely-there piece of material that was now my panties. And now Alex was giving me a choice, don’t strip myself naked in front of my teammates, but have my secret as a Sissy revealed, or convince these guys I was a girl, and keep my secret safe. The thought process in my head was very short. If I could escape this whole nightmare soon, there’s no reason why anyone would ever have to know about any of this. But if all my friends on the team found out, I’d be branded a pathetic, panty-wearing sissy for the rest of my life.
“And you won’t tell anyone I’m Sissy?”
“O-okay, I’ll do it.” I say meekly and nervously.
“Awesome!” Alex practically shouts, immediately pushing open the door to the Men’s’ locker room.
The sweaty room is dotted with naked and half naked men, who all begin grabbing their towels to cover themselves, yelling at us ‘to get the fuck out!’ and other similar comments, but Alex simply walks proudly into the room holding the hand of a gorgeous red headed cheerleader tottering on skyscraper heels, wearing one of the most revealing outfits you could imagine. I feel myself shaking. I had been in this room many times before, I’ve been half naked in this room many times before, but as I teetered on my ‘fuck me’ heels and brushed the long tresses of red hair out of my made-up face, I knew this was going to be very different.
“Boys, boys, boys! This is your lucky day! Young Kelly here lost a bet at her sorority last night, and you fine young men here will all be the beneficiaries! She now has to do the sexiest, the sauciest, most titillating dance you have ever seen!” Alex does her best impersonation of a ringmaster at a circus as suddenly all my friends break out in to cheers and hollers and begin looking up and down my body with raw lust. I gulp, as I spy my best friend Steve move from the corner to take a front row seat at the bench Alex is dragging to the center of the locker room to use as a narrow catwalk.
As all the boys chant and holler, Alex leans in and whispers in to my ear “Make this good, Miss Morgan.” giving me a light spank on my butt, encouraging me to step on to the low bench all the boys have gathered around.
My hands begin to shake violently and my stomach twists itself into to knots, making me feel like I want to throw up. “C’mon, girl, we’re not going to bite!” Jeremy, the sweeper yells.
“We’ll take real good care of you!” Tom, the right wing, says suggestively as he lends me his hand to help me step on to the bench. I look at the floor and grab the big hand as I step up onto the long wooden bench as the guys break out in a cheer in unison. Someone grabs a radio, and turns up the music to some R & B track real loud. I look down at all the expectant eyes on the faces of all my former friends and team mates with sheer horror as they begin clapping the hands to the music. The room is now filled with a dozen crazed guys, all clapping and joking, expect for one person. Alex, with her arms crossed and tapping her foot, gives me an unimpressed look.
I begin to slowly move my hips to the music, walking down the bench, trying to ignore all the guys leaning down to peer up my short dress. “Oh my God, she is absolutely dripping wet!”
“I bet they twisted her arm real hard to come and do this for us!” The guys say joking, my cheeks blushing a bright red.
I groan to myself quietly as I look at all my friends and team mates crane their neck low so they can see my sopping wet, bright blue panties. My body desperately wants to press its knees together and pull the skirt close in to my body and keep the eyes away from my underwear. But I just try to focus on swaying my hips to the music sexily, feeling my skirt dance in the air, showing off my butt, as I see a series of tents forming under the towels and shorts of my happy audience. I begin swaying my arms, and moving my hips in wide circles, and in general, trying to impersonate the strippers I saw dancing on television.
“Take it off!!”
“Yeah, let’s see those big titties!” One of the meatheads shout, as I feel the first hand grope my tight ass, making me jump and squeal like a little girl.
“What? No touchies?”
“C’mon Kelly, you said you would act just like a cheap, dirty stripper. Let them touch you, at the very least, to slip a dollar bill under that sexy thong!” Alex cries out, watching the show with a huge, satisfied smile on her face.
All the guys suddenly spring off their seats, creating a cacophony of noise as they knock over seats and benches and each other as they race to their stalls to find their wallets. I can hear them all talking, talking about my sexy body and wet panties. I cringe when I see them return, most with thick wads of cash and large grins. Suddenly, as I do my amateurish dance making my way back down the narrow bench, I feel hands all over my butt, fingers fondling all over my ass and hips in a very invasive manner. I squirm and squeal as I feel the fingers slipping crinkled paper notes into my tight thong. The next thing I know, I feel big hands fumbling with my skirt and then, as I look down shocked and mortified, the skirt falls down to my feet, a large cheer resonating around the small locker room.
I stand for a moment in absolute disbelief, feeling a dozen hands all over my thong and backside, slipping the dirty, scratchy notes next to my sensitive skin. I try to sniffle back the tears as I guide my ‘fuck me’ heels out the skirt, stepping out of the small, blue piece of cloth, doing my best to dance to the beat of the music as I moved up the bench surrounded by my horny team mates, doing my best to ignore the barrage of hairy hands playing with my thong.
“Take off your top!”
“Yeah, let’s see those melons!” I cringe when I hear the calls, and I feel worse when I see Alex motion to rip off my top. I close my eyes tight, as I run my hands along my sides like I saw the strippers in the movies do, before holding the hands at the bottom of the top. My lower lip trembles wildly before, in one quick motion, I lift the sleeveless top over my head and fling the garment into the crowd. There is a disappointed groan as the boys see the cotton wadding filling the matching blue bra, and I see Alex give a stern expression, giving me a very clear impression of what she wanted me to do next. I try to control my breathing, trying to stop the wave of tears from coming, as I quickly reach behind my back, and try to undo the clasp. Even in the commotion of stripping in front of all my team mates, revealing my ‘new’ body, I think how strange it is to be undoing a bra clasp from the position of the wearer. My thoughts are broken as I see tissue and cotton wadding rain down on my team mates as I fling the unhooked bra over the boys head, making them jump out of their seats to grab it. The boys are now yelling and hollering like mad men, as they all stare fascinating at my small, pert breasts and erect nipples.
I have never felt more exposed, naked except for a blue thong and ridiculously sexy high heels, all my friends and team mates who I worked, played and joked with for months, all stroking themselves or touching my naked legs and ass. It takes all my concentration to keep dancing up and down the bench for the dozen or so guys, all reaching up to my thong, taking their time to slip in an old, dirty dollar bills, usually with a firm grope of my butt as they did it. I almost fall off the bench when I see my best friend Steve whip out his hard, pulsating cock and begin to jerk it up and down, and I feel the first, verified tear roll down my cheek.
Still looking at my best friend jerking off his large cock as he looked up and down my body, I see Alex move behind him, almost knocking Steve off his seat as she barges through the crowd before wrapping her hand around my wrists and tugging me down from the bench to a chorus of disappointed boos.
I am so thankful as Alex drags me quickly across the locker room, struggling to keep up in my heels as I cover my breasts with my free hand. But as I look at my crumpled skirt and cheerleader top lying on the ground getting further and further away, and the large door to the locker room getting closer and closer, I begin to pull back on my ex-girlfriends hand.
“Alex, what are you doing!? I can’t go outside like this!” I plea, as I grab the doorframe, trying desperately not to be pulled outside in only a thong and heels, my new, naked breasts completely on display for the world to see, not to mention the dozens of crinkled, dollar bulls in my thong, virtually announcing to the world that I was a cheap stripper.
“What? You want to lose the pretty panties as well?” Alex says with a snarl.
“Well, if you didn’t want to walk through the school naked why did you dance like that?”
“What? You said-“
“You reminded me of a eleven year old boy at a school dance.” she says angrily before trying to tug me out the door again.
“No! Please! I’ll do better!”
This stops Alex, and she turns to me with raised eyebrows. “Really?”
“Really!” I say, as a few more tears roll down on my cheeks, my knuckles white from gripping onto the doorframe.
“Okay, if you do exactly what I say, I’ll let you wear that cheerleader uniform so much to our first class. And if you don’t, I’m going to cut the uniform, and that thong in to shreds. How does that sound, honey?”What choice did I have? I just nod my head dumbly, sniffling back my tears. “Good girl. Oh look, you’ve ruined your make-up. Stay still while I fix it for you.” Alex opens up her small purse and pulls out some tissues and more pastel vials of mysterious make-up.
She squeezes my cheeks before she carefully applies her creams and lotions, saying almost absent mindedly while she does so “Before, you were just moving your hips and swaying your arms about stupidly. What’s that? I want you to gyrate those hips like a cheap whore. I want you to spread your legs and finger that pussy through your panties. I want you to blow kisses and lick your lips and give sexy winks to all your old friends. And absolutely no- more- tears! Got it?”
I do my best to nod my head with my face in her tight grip, terrified at my latest humiliating task, doing my best to blink away my tears. Alex finally puts the make-up back in her purse. I cringe as she roughly pulls out the course notes out of my thong.
“Good girl.” she says as she flicks through the wad of dollar bills before putting them in her purse, a look of satisfaction on her face. She spins me around by the shoulders sharply and gives me a firm spank on my exposed butt cheek to get me moving. “Now, go give them a show they’ll never forget.”
I stutter forward on my high heels with the force of the spank, the boys, my team mates, all celebrating as they see the almost-naked girl walking back to them, her face freshly made up. I gulp, never feeling more nervous in my life, as I try to muster up the courage to step back up on the bench and do a sexy strip tease for all my friends. That changes when I see Alex make her way across the room to pick up the slutty cheerleader top in her hands, positioning it in her fists as if she was about to rip it in half, just like she had done with my pink camisole an hour ago. Except this time, I don’t think she was going to replace it with another piece of clothing. Almost in panic, I hop back on the bench, making all the boys scream in delight, and I begin kicking my legs high in the air, doing twirls as I run my hands up and down my body, and smacking my own ass while I blow kisses to all my old team mates. The boys seem much more excited by my dance, and I see Alex smile and release her tight grip on the top.
The boys go crazy as I follow Alex’s instructions, moving my hips wildly with the loud beat of the pop song on the radio, licking my lips as I wink to Steve and my other team mates, my cheeks burning red under the layer of make-up on my face. I close my eyes, biting my lip to distract myself from the shame as I spread my legs, and begin to probe my prosthetic pussy through the thin, semi-transparent and sopping wet blue thong. I hear the boys reach a new level of excitement, comments like ‘I can’t believe this bitch!’ and ‘What a slut!’ can’t detract from the pleasure my fingers are giving me as they rub my trapped and tortured cock sensually.
“Play with your nipples!” Steve pants, his eyes glazing over with lust as he stares at my small, sexy body.
I don’t why I do what I am told, moaning slightly as I feel the electric feelings of pleasure radiating from my chest as my fingers begin to tease my nipples, but the crowd goes crazy, and I see a wide smile and a nod of the head from Alex. As I follow Steve’s directions, I can’t help but remember the good times we used to have. Soccer, double dates at the movies, countless friendly conversations talking about what we were going to do in the future. But as I continue to play with my tiny titties while he played with his cock through his towel, licking my fingers and rolling my nipples in between them making me moan harder, feeling my cock strain against its tiny cage, I knew I would never be able to look at my friend the same again.
“This girl absolutely loves it!!” Steve screams as his hard cock springs up from under his towel before he starts jerking it up and down. I cringe, closing my eyes, forcing myself to turn away from my best friend.
As I make my way back down the bench, big, meaty hands shoving wads of cash in my thong, my ass groped by strong hands making me jump slightly. I notice the damp feeling return to my thighs, knowing that I am leaking precum as I moan and roll my nipples in my fingers. But in this moment, I didn’t care, enjoying the waves of pleasure rolling through my body.
“Take off those panties before you ruin them!” Alex yells, barging her way through the crowd of guys. “Sorry, but these are my panties and I don’t want them ruined.” Alex says without remorse as she puts her thumbs under the waistband of the tight thong before tugging them down in one motion.
The crumpled notes go flying everywhere while the crowd goes nuts, their eyes lighting up as they see my naked, bald pussy, the boys cheering for what seems like minutes. I gasp, feeling light-headed, looking down at my naked body, my wide hips, small, perky breasts and cute pussy; doing absolutely everything in my power not to move my hands to cover myself, as I feel the blood rush to my cheeks, my face feeling like it is burning I am so embarrassed
“Don’t stop the show, honey!”
“Yeah give us our money’s worth!” I hear them call, all laughing.
My vision is blurred by tears, but as I make my way back down the wooden bench naked other than a pair of ridiculously high ‘fuck me’ heels, completely surrounded by hollering, cheering guys that I used to call my team mates, I can’t help but notice every single one of them has pulled out their hard cocks and are not taking their eyes off my body. I feel like I’m going faint, I feel like I’m going to die I am so mortified, but I just do my best to dance to the beat of the pop song, doing my best to ignore the precum slowly leaking down my inner thigh.
I begin playing with my sensitive tits again, the pleasurably sensations racking my body, and for a moment, I feel better. I can’t help but slowly trace a hand down my toned stomach and begin fingering my bare pussy, rubbing my balls tucked under the pussy of the Sissy Suit. I can’t help it, I moan like a whore when I enter two more fingers into my slit, rubbing my balls hard. For a moment, I forget about all my friends cheering as I strip for their entertainment, jerking off to my body, I forget the torture after torture that has been the last month, all I can feel is wave after wave of pleasure radiating from my crotch and my chest, all I can hear are my own lustful moans.
I open my eyes foggily to see the crowd yelling something at me, but I can’t really understand it. I feel sweaty hands grab me by the shoulders and waist, and they begin to bend me over. I know what they are doing, but I can’t resist as the hands bend me down from the waist, making me groan in disappointment as I take my hand off my rock hard nipples to plant it flat on the bench, saving myself from toppling over onto my face. My pussy and ass are now on complete display to the room of horny guys and hard cocks, and I can hear them gasp when they see the small, stainless steel end to my training butt plug.
“This girl is a freak!”
“That explains the dripping pussy!” I hear someone cry from over my shoulder. I just close my eyes, trying not to cry, trying to take my frantic fingers out of my pussy, as all these guys watch with dropped jaws.
“This girl is the biggest fucking tease! Do we get to fuck her what!?” I hear Steve yell at Alex, his cock bobbing up and down as he moves out of his seat to get a closer look at the steel plug and the fingers plunging in and out of my pink pussy.
“I don’t know about fucking but I can tell you this girl absolutely loves to suck cock!” I look up in horror to see Alex’s eyes lit up as she sees me bent over in the hands of the group of big, muscular men. “Isn’t that right, Kelly?”
My wide, scared, teary eyes should have told the guys the truth, but I don’t think they were looking at my face as I leant forward, naked, my whole body on display. My mouth wide open in shock, my lower lip trembling, tears beginning to roll down my cheek, I see Steve step in front of me, effortlessly slipping his dripping and veiny cock in to my wide open mouth. “I’m first!” he says, as he moans in pleasure as my lips instinctively wrap around the large piece of meat in my mouth.
Bitter tears roll down my flushed cheeks as Steve, my best friend, bucks his hips, pumping his cock in and out of my mouth, while my fingers plunge in and out of the folds of my pussy, a group of men groping my ass and tits. I squirm and squeal and moan, but it is all muffled by the thick cock in my mouth and the strong hands holding me in place. The nightmare is topped off with Alex’s smiling, laughing face, clearly having the time of my life as my friends thrusted his slimy cock in and out of my mouth.
I am crying my eyes out, but I can’t help but give muffled moans of ecstasy as my fingers massage my trapped cock, while the boys twist and tease my erect nipples. But my eyes open wide when I feel large fingers begin to probe my asshole, taking a grip of my butt plug. I squeal, first in pain and then in delight, as I feel the plug moved out stretching my hole wide, before being slipped back in. I arch my back as my body is consumed by the feelings pouring through my body, giving a loud , horny moan from behind the cock in the mouth.
“She fucking loves it!”
“Holy shit, this is the hottest fucking thing I’ve ever seen!” I hear voices say, as the boys go nuts, all jerking their cocks over my body. I cringe when I feel the first wad of warm, hot goo splash against my back.
I feel Steve’s cock somehow harden ever more, making it like a steel rod is thrusting into my throat. “I can’t- can’t hold on-” Steve gasps before he pulls me down to the bottom of his cock before erupting into my mouth.
Steve pulls out his large cock from my mouth with a pop, and I immediately begin desperately gasping for breath in between my swallowing of Steve’s salty cum and my loud, feminine moans as I feel the fingers wrapped around the base of my butt plug quicken its pace. The butt plug invading my hole brings groans of pain and moans of pleasure, and I find myself squirming around the plug, bucking my hips, letting the invader get further inside me, almost making me forget the cum slowly dribbling down my chin.
Almost immediately, another big, muscular man with a large, bobbing, dripping cock stepped in front of me. I looked up miserably to see Jeremy smiling down at me, his eyes glazed over with a look of lust. My moaning reaches a crescendo, and I feel the butt plug moving in and out of my poor ass speed up to a frantic rate, and I scream in a high-pitched and gasping voice “Nooo!!” as I feel my body reach orgasm and a thick load of white goo erupt from my pussy and splatteronto my naked thighs. I open my eyes to see the look of lust on the face staring down at me gone, replaced by one of disbelief.
All the cheering, all the crude comments, all the groans of pleasure end in a heartbeat and the room is filled with an eerie silence. Everyone seems absolutely mesmerized by the thick cum slowly trickling down my pale thigh.
“Kevvy, just what are you doing!?” I go pale as I hear Ms. Pascoe’s very familiar voice.
All the boys just take a step away from me, almost all shouting in unison “KEVIN!?!”
Jeremy takes the time to rip off my red wig, before stepping back to analyze the made-up, cum-covered, sobbing face of his team mate. The arm holding me up in my bent position suddenly feels weak, and my cum-covered body falls in a heap in the middle of the circle of men.