Crossdressing at the Girls' Academy

"Well, now that everyone else has had their fun, I guess it's my turn at your pussy." I let out a halfhearted groan but couldn't bring myself to resist as he grabbed my shoulder and spun me so I was laying across the width of the bed on my back. My legs were now off one side and my head was slightly hanging off the other. It was really uncomfortable but all I could do was groan softly.

Without any hesitation, Todd positioned himself near my legs, spread them forcibly, and plunged himself deep into me with one thrust. My ass accepted him easily - I was loose from earlier and his cock was nowhere near as big as Dave's. I laid back and let him have his way, barely aware of his motions.

Dave didn't let me rest, though. He stood up and made his way to the other end of the bed, near my head. "Guess I'll take this hole," he proclaimed, then pressed his penis against my lips. It was still covered in cum from earlier but was already rock hard again. He forced his way inside without preamble, entering my mouth while my head was upside-down, hanging off the side of the bed. Now I was alert again. There were cocks in me at both ends! I couldn't see much except Dave's hairy ass but I was very aware of the sour taste of my own rectum as he forced his way deeper inside me. This was humiliating. I was being spit-roasted, reminding me again that I was nothing more than a toy to these three.

After a short amount of time, I noticed Dave wasn't stopping his dick's descent. He was forcing me to deepthroat him! I truly started to panic when I felt his head probe against the entrance to my throat and tried to pull back, but he had me completely pinned. He grabbed the back of my heard, steadying it.

"Oh yeah, baby, we're going all the way tonight." Dave moaned in ecstasy as he pushed his way further in. "I hear the trick is to swallow a lot. You better be ready." I screamed around his huge cock, but he wasn't stopping. Another inch went in and I began to gag. Desperately, I took his advice and swallowed rapidly, letting it sink in another inch. "Ooooooh yeah, that's what I'm talking about. Her pussy might not be so tight anymore, but this hole is like a vise," he proclaimed. Tears were streaming down my face as I struggled not to vomit. "Damn girl, it's so sexy when you make those noises. I could just eat you up!" He paused. "But I guess it's you that's doing the eating, huh?" He laughed evilly and thrust in another inch. Now over half his enormous cock was inside me, deep into my throat. His black ballsack hung directly above my face and I could smell its sweaty aroma. I thrashed in vain, my weak protests muffled.

Meanwhile, Todd had still been pounding into my asshole. I had been ignoring him, but then he started fucking me at a brutal speed. I could hear the sharp sound of his balls slapping against my skin. After a few minutes, he got even wilder and started spanking my bare ass with his hand. It stung like hell and now I was in misery at both ends.

Every inch was agony, but at last Dave bottomed out, every bit of his cock inside my mouth. His balls were pressed hard against my nose now, my vision filled with his asshole. His testicles were hairy and musky, and it was starting to block my breathing. I could barely move and it took every effort I had to suck in small snorts of air around his thick scrotum. I screamed as loud as I could, but it was completely absorbed. At this point, I didn't think it could get any worse. I just wanted the night to end or for me to pass out - whichever came first. Slowly, Dave slid his cock all the way back out; I could feel every contour, every ridge as it slipped through my throat. When it at last broke free, a huge gob of spit and precum still connecting it to my mouth, I coughed and sputtered, gasping for air.

The night wasn't over yet, though. I felt Todd pause his fucking, then the bed sunk as someone sat down. I still couldn't see around Dave, but it must have been Ricardo. I felt him lay down beside me, facing the same direction. Todd withdrew his dick and I wondered what was happening. Then, in one quick motion, Dave and Todd lifted me a few feet off the bed, letting Ricardo slide under me, then lowered me atop him. I was now laying across his body, and I could feel his sweaty skin, his naked chest pressing against my back. His cock was growing as it pressed between my legs against my own penis. Then, he lowered his hands to my ass, gripped a cheek in each hand, and thrust his cock inside me from this new position. I let out a pitiful moan as he started to fuck me again. The angle was different and I felt stimulation in strange new areas.

Before I could get used to it, however, he stopped his thrusting, dick still buried inside me. Then I felt something else press into my asshole, right up against Ricardo's dick. My heart pounded even faster as I finally understood what they were doing. They were going to double penetrate me! There was no way I could handle that. True, they weren't as big as Dave, but two cocks weren't going to fit. Despite my yells, Todd pressed on. He forced his cock in beside Ricardo's, pressing with all his might. I didn't think it would go any further, but something finally gave way. With a cheer Todd started to slowly inch his way into me. I was stretched beyond belief - it felt like an actual hole was being torn through my body.

Dave silenced my screams of pain by pressing his dick back into my mouth and thrust himself deep back into my throat. Now all three men were penetrating me. I didn't feel any of the pleasure from before. My asshole felt like pure fire as the two men slowly took turns thrusting into me. Dave's deep face-fucking was torture. I started to black out from the pain, barely conscious of anything. For a while, the only sounds in the room were the men's grunting, my low moans and gagging sounds, and the SLAP SLAP SLAP of Dave's ballsack smacking against my nose. My world was nothing but dicks, sweat, and pain as I was completely dominated, covered from all sides and violated in every orifice. I was nothing but a receptacle, unable to move and not conscious enough to even try. I wasn't even a whore to them anymore.

Just as I started to completely black out, the door suddenly swung open with a SMACK! "Don't move!" I heard an authoritative voice shout. I couldn't see, but I recognized the voice: it was Michael, Anna's boyfriend. Everyone in the room froze, my holes still stuffed with their dicks.

"Back away from him!" I heard Michael command. There was a rustling noise, then suddenly all three of my violators withdrew from me all at once. Ricardo shoved me off him and Dave backed away, leaving me alone on the bed, broken and covered in cum. But finally, I could see what was happening. Michael indeed stood in the doorway, in full police uniform and with a pistol in his hand.

"You fuckers are in a lot of trouble. It's going to be hard to talk your way out of this one." He was shouting at the other three with so much force that they were physically cowering in fear. I heard a noise behind Michael and suddenly Anna ran into the room, freezing in shock when she saw what was going on. A look of absolute horror filled her face and her hand flew to her mouth.

"Oh my god, Alex! What have they done to you?" she exclaimed, running to my side. She frantically dug into her purse, producing a handkerchief. "I'm so sorry! I thought you were enjoying yourself, maybe getting lucky tonight," she rambled, not pausing for breath as she began to futilely wipe at the filth covering my face. "But I had a really bad feeling when Diana told me some shady stories about these guys, then you weren't answering your phone and I got really worried and forced Michael to drive me down here..."

I didn't have the energy to respond, but I did feel a faint warm feeling of relief. Relief and...happiness? I don't think anyone had ever shown so much genuine worry about me before. Not even my parents ever acted like this. Yet here I was, a filthy, cum-soaked slut and all Anna cared about was my well-being. I did see her briefly eye my dick but she said nothing.

"Okay, that's the best I can do," she procalimed, putting away the cloth. "I'm going to take you home now while Michael deals with these scumbags." She produced a wool blanket and wrapped my body, then, with surprising strength for her size, lifted me into her arms like a baby. The feelings of gratitude and relief washed over me and I suddenly felt very tired. Before she even made it to the door, everything went black.

I woke up dazed and disoriented. What had happened? Where was I? I didn't recognize my surroundings at all. Why was I was tucked under the covers of a plain bed? I looked around. I was in someone's bedroom, very neat and proper, with a tidy desk, stark dresser, and painstakingly-arranged framed photos. I recognized Michael in a few of them and realized I was in his house, most likely his room. With that realization, the rest of the events of the night before started to slowly come back to me.

I became aware of a dull throb of pain in my ass and it all suddenly flooded my mind at once. The party. Giving Todd a blowjob. Being discovered as a crossdresser and then fucked into unconsciousness. I shuddered at the memories, then was mortified when I remembered that I had not hated it all. And then I had been rescued, my unlikely saviors presumably taking me here. I pushed down the covers and saw that someone had changed my clothes. I was wearing one of Anna's skirts and a girls' T-shirt with a floral pattern. I had also been washed at some point - my skin was smooth and pure again, no longer covered in cum. I wondered at how strange it must have been to wash my body, including my dick, only to then dress me in a skirt.

It was undeniable that both Anna and Michael knew my secret now. What did they think? Would they report me, forcing me to leave the school and go back home to my parents? I realized I'd miss Anna, and being her friend. No matter what happened, things couldn't go back to the way they were between us, that was for sure. Still, the trauma of the night before only left a faint ache all around my body, and I didn't appear to have any bruises. I even smiled to myself at the memory of my assailants' flustered arrest. Through the cracks in the blinds on the small window, I could see that it was sunset. I must have slept most of the day. I swung my legs onto the floor and started to rise when the door creaked open with a small knock.

"Alex?" It was Anna. "You're up! How are you feeling? You had us so worried." She walked to the bed and sat herself down on the small desk chair beside it after giving me a firm hug.

I was truly happy to see her, surprisingly so. "I think I'm doing alright actually, much better than I thought I would be. Have you and Michael been taking care of me?"

"Yes. Well Michael helped a bit but he's been busy with the police most of the day. He gave you his room and I helped get you cleaned up."

The kindness of these people was astounding. I was momentarily at a loss for words. Then I tried to articulate my thoughts. "Anna, you are a saint. Thank you for this." She started to reply, but I cut her off. "No, I mean..." I paused, my head lowered, then looked her directly in the eyes. "ALL of this."

She hesistated for a second, then composed herself. "Of course, Alex, anything for a friend. Or anyone, really. No one deserved to go through what you did."

I hesitated. "I'm surprised you consider me a friend after, well, you know..." I trailed off and both our gazes briefly fixed on my crotch.

She smiled awkwardly. "It's not a big deal, you know. I've known for months." She saw my eyes widen and chuckled. "Yes, it was actually a bit obvious, with the way you carried yourself and the way you talked. I found it adorable, to be honest. Well, and I could sometimes see your...bulge." She paused again. "Though I am curious about...why? If you don't mind me asking," she added hastily.

I recounted the story of my exile into crossdressing, including a shameful retelling of the party over the summer that got me in trouble to begin with. She was understandably horrified at my actions, but was still supportive throughout the story. When I finished I sat silent, anxiously waiting for her response.

"Well, you're a fucking pig for what you did to that poor girl..." I hung my head in legitimate shame. "...but I think you've more than learned your lesson. It's best if you just try to move on from everything that's happened, Alex." She trailed off, eyeing my clothes as I sat there meekly. "Oh, and...uh...sorry about dressing you in a skirt. I thought maybe it was a gender identity thing and...well, I didn't mean to emasculate you further.

I started to tell her it was fine, but she cut me off with a sudden snap of her fingers. "No, what you need is to be reminded you're still a man. And I know just how to do that!" She grinned and then suddenly reached for the hem of my skirt, flipped it up, and revealed my package, bulging obscenely against the lacy material of the panties. "Wow, miss, you might want to get that looked into!" she joked.

I was shocked. "Woah, Anna, that's okay, you've done more than enough! What would Michael think...?"

"Oh, don't worry about him. We have a very open relationship and do this kind of thing all the time. Besides, I WANT to do this! You're very sexy, Alex, regardless if you're a man or a woman."

I faltered at this unusual compliment, which gave her enough time to push aside the panties, springing my cock free, and then grab hold of my member with both her hands. Without preamble, she started jacking it off furiously. I felt shivers run through my dick as it began to awaken, responding to the pleasurable sensation. Before long it was fully erect. Anna noticed it and winked at me, then lowered her head and began an enthusiastic blowjob.

She absolutely gobbled me up and kept at it for several minutes, but I just couldn't seem to cum. The longer it went on, the more something felt...off. The feeling of her lips slide across my cock was incredible, but it just felt...wrong. I looked down at her and had the sudden wish that it was me in her position, engorging myself on a thick penis. As I thought about it more, I got more restless and my boner gradually died in Anna's disappointed mouth. What was wrong with me? I had just gone through one of the most traumatic nights of my life, but I was suddenly thinking back to it with something bordering on nostalgia. I vividly remembered the taste of Todd's cum, the thickness of Dave's dick as it stretched out my asshole. Why was I focusing on that?

The truth was, I had known all along. I was no longer a man. Something had awakened in me last night, and there was no going back. I was broken. I needed dicks now, no way around it. Like a slut. A cock-craving whore, hungry for my next meal. Who was I kidding? I wanted to be fucked! The thought was shameful. My cheeks burned red yet again and I felt my cock go completely flaccid.

Anna noticed and stopped her blowjob, frowning. She was quiet for a minute or so, then an understanding smile suddenly crossed her face. "Don't worry, Alex. I think I know exactly what's going on here. I have just the thing for you, actually." She stood up and abruptly left the room, leaving me confused and alone with my cock still obscenely exposed under my disheveled skirt and panties. I sat there in silence for a few minutes, trying to come to terms with my new desire - need - for cocks.

All of a sudden, the door swung open again and Anna re-entered the room, followed by...Michael. I swallowed guiltily at the sight of him. Here I was, in his own bedroom, with my dick still exposed from his girlfriend's blowjob. He didn't seem angry, though, just embarrassed. For some reason, he was shirtless. He stood right in front of me, not meeting my eyes. Anna crossed the room, sat on the desk chair, and gave me a huge smile. "Michael's just got back from the police station. I told him what's going on and he agreed!" Michael refused to return her smug smile. "So, help yourself, Alex!" She clapped her hands together. I was confused and speechless as I looked from her to Michael. What was going on here? Why was he so sheepish, here in his bedroom, and she so delighted?

Then, all at once, I knew exactly what was going on. I felt a pang of intense embarrassment, mixed in with a surge of excitement. Giddiness. This was it. This was my choice. There was no going back from this. The room was dead silent. I could hear my own heart beating. Anna was giving me an encouraging smile, while Michael's expression was unreadable. The next few minutes of my hesitation seemed to stretch on for an eternity.

Finally, something inside me gave in and my inner battle was over. Before I knew it, I was rushing off the bed towards Michael, heading straight for the zipper of his pants. In no time at all I had his jeans unzipped and his boxers down to his ankles. His cock was now exposed before me, in all its glory. It wasn't like Dave's monster; it was a manageable, delicious size. My mouth watered as I beheld my prize.

Wasting no time, I took his member in both hands and began jacking it off, just like Anna had done to me minutes earlier. Once it was completely erect, I eagerly wrapped my lips around its head and started my feast. He seemed to be enjoying himself, though he was still standing motionless. The texture, the smell, the taste! This was what I needed. This was the new me! I felt none of the shame from the other night, only excitement and anticipation.

After sucking on the head, I removed Michael's penis from my mouth and began working my tongue down its shaft, slowly making my way to its base. I heard Michael make a soft groan in satisfaction as I reached the bottom and suckled his balls, one and then the other. I made sure to cover every inch of his testicles, not leaving any surface uncovered, before making my careful way back up. Michael was in bliss now and making incomprehensible noises of satisfaction.

When I again reached his head, I withdrew my tongue. Michael looked at me expectantly, his eyes pleading for more. I gave him a grin and a wink and promptly gobbled his cock halfway down my throat in one go. I feasted on my meal, taking it to the edge of my throat before pulling myself all the way back to the top. Soon, Michael was moaning louder and I felt his hands work their way through my long hair and grip the back of my head. Before I could react, he started pushing, trying to press me further down his shaft. I wasn't too excited about deepthroating again, but Dave had more than prepared me for this. I remembered the lesson from last night and rhythmically swallowed, trying not to gag as Michael pushed deeper into me.

Soon he had bottomed out, his balls pressed against my chin. I was in control, though, and didn't let his sudden force intimidate me. I furiously ran my tongue across his shaft and worked my throat to squeeze it pleasurably. It wasn't long before Michael gave a short grunt of "Oh, fuck!" and released his cum straight down my throat. I frantically swallowed it, determined not to choke as I felt the slimy semen slide directly into my stomach. After half a dozen powerful spurts, Michael was finished at last and slowly withdrew his dick. As it exited my mouth, a thick trail of cum connected its tip to my lips. I hungrily caught it back into my mouth, then followed it back to its source. I traced the mixture of cum and my saliva down Michael's shaft yet again, all the way to the underside of his balls. I spent a few minutes giving attention to his taint before doing the whole thing in reverse and finally finishing my meal.

Still on my knees, I looked up at Michael patiently. He was catching his breath, but saw my expectant look. "That was amazing, honey...er, I mean, dude," he sputtered.