Crossdressing at the Girls' Academy

Story Info
Dressed as a girl, he's caught and forced into a gangbang.
12.4k words
4.64
117.9k
113
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
TiefBlau
TiefBlau
69 Followers

How do I start the story of my transformation, from a young punk to a cock-hungry whore? I guess it begins with the summer of senior year of high school, a night I still look back to with shame. Those were dark times, when I was mostly a bundle of hormones and vanity. Still, I guess I need to start from the beginning.

Looking back on the night, I never should have attended the party, but I was so unbelievably self-confidant then. I had just turned 18 and it had been weeks since I last had sex - the high school graduation party seemed like the perfect opportunity to talk myself into some young freshman's pants. But after I got there, none of my usual charm seemed to be working for me. What kind of prudes were these girls that they wouldn't jump at the chance to get fucked by someone like me? After a few hours, I began drinking heavily and tried to salvage a wasted night.

My chance presented itself when I noticed one of the girls who had had far too much to drink was all by herself, her friends gone. She was slurring at no one in particular and most people seemed to be ignoring her. Perfect! This was my chance. I made my way over to her and gave my patented charming grin, followed by a greeting. She responded, but didn't seem very interested in my advances.

After talking her up for an hour or so, I learned she was also 18 and quite a ditz, talking about a modeling career I'm sure was ill-fated. But she still wasn't responding to any of the pick-ups I was using. I got bored with this game and convinced her to follow me to a spare room with some bullshit story about losing my keys. She was drunk enough to buy it and soon we were alone in a dark bedroom, the music of the party muted through the walls.

"Okay, enough playing hard to get," I said as I started to unzip my pants. She looked panicked but was in no state to offer anything but a weak moan of dismay. "Time to put that pretty face of yours to work." I shoved her down to her knees and pulled my cock free. Without hesitating or waiting for her response, I pressed it against her lips and forced it between them. Usually being quick and forceful was the way to go with girls like this. I've done it dozens of times. They're always too drunk to put up a fight and let me have my way with them, forgetting it all ever happened by the next day.

The girl in front of me was no different, struggling weakly and grunting around my dick, but she allowed me to bob her head and pleasure myself. It didn't take long until I was ready to cum, so I plugged her nose and forced her to swallow it. I was just about to force her onto the bed and start the main course when the door swung open suddenly, filling the room with light and framing a young man and a giddy-looking blonde.

"Woah, sorry, dude, didn't realize this was taken. We'll just..." he trailed off as he began to size up the scene before him. My prey took the opportunity to pull herself away from me, coughing up cum and spit, and then started crying.

What followed is still a blur to me. The guy and his girl were sharp and my bitch turned out to be more coherent than I thought, running to them and sobbing out accusations. The outsiders quickly realized what had been going on, and it only took a few minutes for the rest of the party-goers to find out and paint me as some sort of criminal. I tried to protest that it was all a misunderstanding, but before I knew it someone had called the cops.

The next few months were nightmarish. I found myself caught up in conferences with the school, as the girl's family debated with my ex-teachers on whether to take me to court. Luckily for me, the school was reluctant to bring me in front of the courts, probably because it was worried about its reputation. Pathetic. By the end of the process, I was put on probation.

Since I had indicated I was planning to go to college, I was given a small list of private universities where I could attend and still complete the terms of my probation, which included community service and frequent visits with a correctional officer. If I wasn't accepted to any of them, I'd have no choice but to stay at home with my parents and their palpable disappointment. There was no way in hell I could endure more of my father's fits of anger or my mother's sobbing, so I applied to every college on the list.

The replies rolled in the following week, rejecting me one after the other. I guess it's not easy to get accepted into a college as a petty criminal, especially without a scholarship. Soon, the only school left on the list was some girls-only academy, but I was desperate enough at this point to try anything. Without a real plan in mind, I emailed the school and explained my situation, careful not to reveal my gender. Fortunately, my name, Alex, is gender-ambiguous, and the woman who replied didn't seem particularly interested in any details. After a few email exchanges full of ass-kissing, she seemed to take pity on me and sent me a link to apply, saying she would vouch for my admission.

I had started this without any idea how to follow through, but the ideas started flooding in. I used some software I found online to create false IDs listing me as female and prayed no one would pry too deeply. I sent the application and waited with bated breath. When I got the reply, my heart nearly jumped out of my chest. They accepted me! The false papers must have worked and someone had clearly not done their job, since I was now an official student of St. Elizabeth Girls' University, starting next month. Hopefully I could breeze through these next four years of probation as a "girl" and never look back. My life wasn't over! Sure, this wouldn't be easy, but I could get through it. I grinned to myself at my own cunning and got ready for my new life.

4 MONTHS LATER

Truth be told, school got off to a rocky start. I was all ready to coast through classes under my new girl persona, but reality gave me a rude awakening.

First of all, pretending to be a girl is HARD. It had taken the entire month of August to grow out my hair and buy girls' clothes, but I didn't have the first idea what to do after that. I ended up spending hours on the Internet researching women's underwear sizes, how to put on a bra, and how to act "ladylike." This was of course all done in secret while my parents were at work. I was grounded so hard that there wasn't much else I could do anyway, so I had plenty of time to learn.

What had taken the longest to learn was how to apply makeup. Every day I'd spend an hour or more in front of the mirror, trying to properly apply eye shadow, choose the correct shade of blush, and use the right coat of lipstick. Then I'd get tired of the sight of my disheveled face in the mirror, unkempt and streaked with botched makeup attempts. I looked like some wannabe drag queen and it sickened me. The worst step was shaving. It was obvious I'd never look like a girl with chest and leg hair - it was doing a lot to contribute to the drag queen image. I ended up spending an entire weekend painfully self-applying a Brazilian wax. It was excruciating, but by the end of it I definitely looked better in my outfits. It was weird seeing myself naked, with smooth legs and a hairless scrotum. I never had noticeable muscles, instead keeping myself lean and thin. Combined with my longer hair, I looked androgynous even without any clothes or makeup on.

One day, after applying my makeup and then donning my full outfit, I caught a glimpse of myself in a mirror and did a double take. I looked so...feminine. With my painted face, long, delicate hair, and simple skirt I honestly didn't recognize myself. I was like a doll. I had done it! I mean, I didn't think I'd be turning any heads but I could at least pass as a girl with no questions asked. I felt oddly proud of myself.

Once school started, classes proved to be equally challenging. I had thought they'd be a walk in the park like high school, but I was dead wrong. Between my homework and visits to the probational office, I had none of the free time I had hoped for and was struggling just to stay afloat.

Luckily, my roommate turned out to be excellent. Her name was Anna and she was a tall, sporty brunette. Back then I was used to judging girls solely on their sex appeal, but I diligently played the part of a girl and she accepted me as a friend. Surprisingly, we grew quite close. If she found it odd when my eyes lingered a bit too long when she changed in front of me she never said anything. Even if she didn't know the reason, she easily picked up on my occasional discomfort dressing myself. She never asked why, but offered to help me put on trickier outfits and learn some of the etiquette expected of a girl. This kindness was surprising to me and I was grateful that she never pried too much.

Anna had a boyfriend, Michael, who frequently hung out in our room with her. He was a police officer, confident and manly with broad shoulders and a confident personality. To be honest, I had even less of an idea how to deal with other men than the girls while dressed this way so I tended to leave him alone. That is, until one day when he invited Anna to a party one of his friends was hosting. A party with other men, apparently. She loved the idea and tried to talk me into going.

"C'mon, Alex, I know you'll have a great time. Michael can introduce you to a lot of his guy friends - maybe we can find you a boyfriend!" I couldn't exactly tell her why the idea didn't excite me, so I stammered out an excuse, my cheeks burning. "No, I can't. Er...I have a lot of work to do and, uh..."

"Don't be silly, you have the whole weekend. Look, I know you can be a bit...shy sometimes, but I promise you you'll feel amazing. Dress up a bit and the guys will be sure to check you out. You'll feel confident in no time." I couldn't come up with a better excuse, so that's how I ended up attending the second party to change my life.

On the big night, I nervously dressed as nice as I was able. I spent a full two and a half hours in the bathroom, applying makeup and adding some elaborate braids to my hair after a suggestion from Anna. She lent me some of her clothes so I could look "as cute as possible." I ended up wearing a lacy pink blouse, an uncomfortably short mini-skirt, and even some delicate lingerie. This was a first for me, so the soft, silky fabric against my balls felt more than a little strange. Anna then let me pick accessories from her embarrassingly large jewelry box, which turned out to be more fun than I was expecting.

Finally, I was ready to go. It was a strange thing to admit to myself, but I looked sexy. There was no trace that there was a man underneath all the clothes and makeup. I had never felt this way before - I mean, I'd fuck me, and it felt good to think that. When Anna and I left our room, I felt confident, and I realized I was actually excited for this party as Michael drove the three of us in his rickety old car.

We arrived a little after 8:00 and I quickly realized that the event was smaller than I had anticipated. There were about 20 people total, not a bad turn-out but nothing compared to the enormous ragers from high school. Still, I had a good time. Anna and Michael introduced me to their friends and I was easily welcomed into their group. Despite Anna's obvious hints when the guys turned away, I refused to let my mind think anything sexual (especially when I was wearing such a tight skirt).

One man, whom neither Anna nor Michael seemed to know very well, proved to be especially friendly. He introduced himself as Todd, the owner of the house we were in. He then proceeded to hover around me for the rest of the night. He was tall and muscular, probably a football player. He talked with an air of confidence bordering on arrogance, but he seemed like a cool enough dude and kind of reminded me of myself, at least before I had begun crossdressing.

After a few hours talking and drinking with the group, I noticed Anna start to herd them into another room. She then turned to me, gave me a wink, and left herself. It was obvious what she was doing, but I was engrossed in a conversation about Todd's time playing football and didn't stop her. Shortly after, Todd introduced me to two of his friends, Ricardo and Dave. Ricardo was a skinny, Hispanic man that Todd obviously had wrapped around his little finger. His shifty eyes kind of gave me an uneasy feeling. Dave was a huge, muscular black man that didn't seem to talk much. He answered mostly in grunts and just went along with the others' jokes.

I ended up talking to these guys for much longer than I realized. We went through quite a bit of beer as well. At first, it felt good to just "hang with the dudes" again. But I soon noticed their wandering eyes and furtive glances and realized I could never have that kind of relationship dressed like this. They were clearly checking me out and, to be honest, it felt good, giving me a strange sort of confidence. I wasn't half bad at this girl thing, was I? I was sexy and others obviously thought so too.

As we talked, the conversation moving from sports to school to drunken adventures, I began to subtly tease these men. I sat so my skirt hiked up a bit and let my blouse hang lose to give a hint of my hairless chest and (nonexistent) cleavage. The boys definitely noticed and I felt my cock twitch confusedly at the attention.

Eventually, Anna and the others decided to call it a night. Todd insisted I stay and offered to drive me home later, so I said goodbye to Anna and resumed the conversation. As much as it embarrassed me to admit it, I liked giving these guys a bit of a show and wasn't ready to leave yet. Soon after, I noticed my phone was almost dead. Todd offered me his charger, so I gratefully followed him down the hallway into a dark room where he promised it could be found, Dave and Ricardo trailing behind.

Todd fumbled for the light switch and flicked it on, revealing the house's master bedroom. It was sparsely furnished, with just a bed, loveseat, lamp, and cabinet. After we all filed in, Dave wordlessly closed the door. I looked towards Todd expectantly, but he just grinned and stood near the wall. Dave and Ricardo spread themselves out so all three men were surrounding me. It was then I noticed their bulging erections. They seemed to be unashamed and began staring directly at me with gazes that were less than friendly.

I suddenly had a sinking feeling in my stomach when I realized where exactly I was. I was in the bedroom of some guy I barely knew along with his two friends, all three of whom could easily overpower me. My own friend was gone and I had just spent the night acting like a slut. My heart started to pound and my cheeks flushed red when I realized what they expected. I edged towards the door, but found my path blocked by Todd, who was wearing a fake sympathetic smile.

"Leaving already, honey? What about your phone?" I mumbled out some excuse and tried to push past him, but he wasn't having it. "The party's just getting started!" He grabbed me by the arm and lead me back towards the other men. "You know, you've been teasing us all night and me and my boys here are all excited now. It would pain us to see you leave so soon." The others pouted mockingly at this. "Why don't you help us relieve some of this...excitement?"

My heart was pounding even faster. I knew where this was going - I've used some of those same lines myself. This was exactly the situation I should not have got myself into. I'm straight! I didn't want to do anything with these strange men! Why had I been so careless? And things could only get worse when they discovered my secret.

"Listen guys, I appreciate the offer; maybe another time, but I really need to get going..." I trailed off as I noticed Todd's smile vanish. Was I in too deep?

"You've been acting like a little slut all night, practically begging to be fucked. And now you think you're just going to go home? I don't think so."

I threw caution to the wind and made a break for the door. Todd was quick and caught me by the arm again, knocking my breath away as he swung me back around in front of him. As I tried to break away, Ricardo moved himself in front of the door. Todd's grip tightened, painfully so. This guy was really strong! I got the message: I wasn't going anywhere.

"Look who finally decided to be a good girl," he chided as he took hold of me with both hands and forced me to my knees. I reluctantly complied. It was too late to get out of this, but maybe if I went along with it I could escape before things got any worse. I allowed him to position me on the floor in front of the bed, and then he sat himself on its edge right in front of me. I gulped when he unzipped and kicked off his pants. Finally, he flung off his boxers, freeing a dick that was already rising to attention.

I involuntarily recoiled. It was huge! I had always thought myself well-endowed, but this guy made me look like, well...a girl. He was already over 7" long, veiny, and growing even bigger, inches from my face. Todd noticed my reaction and chuckled.

"Like what you see? The girls always do. This will be good for you, too, you know." He thought to himself, then added "But it's nothing compared to Dave's. Wait until you see that monster." Out of the corner of my eye I saw Dave grin evilly. "This must be a dream come true for a cock-hungry slut like you!" he continued. "Show me what you've got!" He spread his legs wider, casually leaned back, and waited for me to start.

I gulped and considered the dick before me. I glanced over to Ricardo, who flashed a sinister smile. I couldn't see any way out of it, so I hesitantly leaned forward and stuck out my tongue. I was now less than an inch from another man's penis and dressed as a girl. Could this get any more humiliating? I fought back a wave of nausea and reluctantly tongued the very tip of the cock. It didn't really taste like anything - yet. I timidly began to run across the head. Todd made a slight groaning sound, which I took as a sign of encouragement.

"Yes, that's it, bitch. Now work on the rest, too." I sighed and grudgingly turned my attention to the base of the cock. I inexpertly ran my tongue up the shaft, which produced another slight moan. This wasn't so bad. I mean, it was horrible, but my tongue was barely touching him. Could it even be considered gay? I would just finish him off like this (careful not to go too low near his hairy ballsack), go home, and forget this night ever happened.

I kept this up for five minutes before Todd became impatient. "Okay, enough teasing, on to the main course now." My cheeks flushed bright red, but I pretended not to hear him and continued at my hesitant pace. When I gave no response, he suddenly took matters into his own hands. "Fuck this weak shit!" he roared, then grabbed me by the back of the head with both hands and forced my mouth down his dick. Before I could resist, it was past my lips and halfway inside me. "Oh yeah, that's what I'm talking about," he sighed.

There was a human male cock in my mouth! I tried not to panic as I struggled to breathe and my tongue worked in vain to avoid contact with the intruder. I averted my eyes from the pubes that were now alarmingly close to my face. But I could still taste everything. It was a musky, slightly tangy taste and very, very wrong. It was the taste of another man's dick! After a few seconds frozen in this pose, Todd began using his hands to force my head back and forth along the upper portion of his shaft. To his credit, he was careful not to push past my throat, but it was hard for me to be too thankful. I was so horrified by my current predicament that I had given up all struggling and was practically catatonic as I let this man abuse me like some fuck toy.

In out, in out, in out. I felt the veins of his cock as they slid past my lips with every lunge. I kept my eyes closed, but it did little to lessen the experience. It was impossible to ignore the warm rod that was forcing its way into my mouth. This was all my fault - I had indeed been acting like a little whore, and now I was being treated like one. As Todd roughly had his way with me, my cheeks burned with shame. Before long, he began to pick up speed and thrust his hips forward while still pushing my head down. I started to lose my balance and was forced to grip his naked legs to steady myself.

TiefBlau
TiefBlau
69 Followers