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The Fancy Dress Party

By: Benedikta



It was the day of Radley Hall's big fancy dress party, and the day I had chosen to show my true colours to the world. Well, it wasn't exactly my choice - Donna, my roommate, my best friend and my sometime lover had been on and on at me, and the party seemed to be the perfect excuse for me to dress up and have fun.

I'd been dressing up in women's clothes since I was six - growing up in a house with three older sisters and an errant father can do that sometimes, I guess! Anyway, my sisters had been dressing me up since I was little, and I'd grown to become accustomed to wearing dresses, skirts and little blouses. In fact, over the years, I'd grown to love the feel of women's clothes more than men's.

Of course, such behaviour was never encouraged at school - once I'd been beaten up when I forgot to take off the nail polish from my toes and had to change for gym. Since then, I'd become very careful to cover up my predilection. Until I started university, anyway!

Donna had been my friend since I was eight - she had been my sister Judy's friend originally and had joined in our games. She knew that I loved to dress up as a girl, and as we became closer over the years, she encouraged me and helped me. For a while we were the same size, so I used to go over to her house in the holidays and she would dress me up in her clothes and teach me how to apply make-up. We shared our first sexual experience together one summer, and had been casual lovers ever since.

Time passed, and we grew up, and somewhere along the line, we both discovered that we were both interested in our own sex. She loved girls and I thought I loved boys. My ultimate fantasy was to have a boy make love to me when I was dressed as a girl.

We both left school and decided to go to the same university, so we could be close to each other. In the first year I had had some experiences with both boys and other girls, but nothing special. 

In the second year, Donna and I rented an flat together. I spent most of my time in private dressed as a woman, but had never shown myself to anyone other than Donna. Until the day of the party, that is.

"Just imagine, you'll be able to go out dressed as some little slut and no one will really be able to think too much about it," Donna said to me as we talked about it in the bath together. "So what do you want to go as?"

"I don't know," I said as I massaged her feet. "Something sexy, but innocent - maybe a school girl..."

"Like Britney?" she asked. "Hit me baby, one more time!" she sang.

"Yeah, or Dorothy from The Wizard of Oz - but with a really short skirt, of course! How about you?"

Donna didn't need to think. "Madonna - Like a Virgin era of course!"

"Mmm, I can just imagine it now - basque, lacy stockings, fingerless gloves - you'll look so damn horny I could eat you up!"

"I may just hold you to that if neither of us get lucky!"

"Count on it, sweetie," I said as she sank into the foam.

Over the next few days, I mulled over my costume. I searched the internet until I found what I was looking for. It arrived a few days later, and I showed it to Donna when she got in.

"A cheerleader? Very slutty - definitely you! I think it's perfect. You may have even outdone me this time!"

"Somehow I doubt that's possible - you're the one with the boobs, remember?" I said, reaching around her and squeezing her large breasts.

"Yeah, but I like my girls small!" she said kissing me full on the lips and squeezing my dick through my jeans. She still had an effect on me and she knew it, but pulled away, giggling. "So, do I get a sneak preview?" she asked as she fell on the sofa.

"No, you're just going to have to wait until Saturday," I told her as I picked up the dress and went into my room.

"Oh, you spoil all my fun!" Donna shouted as she picked up the TV remote.

In my room, I sat on the bed and looked at my dress. It was tiny, barely big enough to fit me, and it shone with a dull gleam. I made a mental note to get some more latex polish as I posed in the mirror, holding the dress in front of me. It was mostly a dark burgundy colour, with a t-shirt style top. The tiny, flared skirt was trimmed with baby blue rubber. It would barely cover my bum, so I knew I'd need to get some new underwear as well. I held the dress up to my face and inhaled deeply, savoring the smell of the latex. I could feel myself growing hard as I thought about Saturday night, the night of the party. I wanted to put the dress on there and then. In seconds I was naked, and unzipping the rear of the dress. A zipper went all the way down to the top of the skirt. I stepped into the dress and pulled it up. It was quite snug on the top of my thighs and over my butt, but a gentle pull and the waist slipped into place. I reached behind me and pulled up the zip, feeling the latex close around my slim body.

My cock was quite hard under the skirt, making it bulge out unsightly in front of me, but the feeling was incredible, like tiny electric shocks in my genitals. I looked at myself in the mirror, and wondered what to do with my hair. It was quite long and blond, bleached by the sun, and Donna had cut it for me in a fairly androgynous way. I plucked one elastic band from the dresser and pulled most of my hair back into a short pony tail. I looked gorgeous, even if I did say so myself!

I twirled around, watching myself in the mirror and wondering what shoes I should wear for the big night. I realised I was going to have to go shopping. Life's a drag sometimes!

The week crawled past slowly, but finally Saturday arrived. In the afternoon, both Donna and I retired to our rooms to get ready. I spent a good hour in the tub, making sure I removed all the hair from my legs and my bum. Luckily, I had never grown hair on my chest and the ones on my arms were very fine and blonde, so I didn't have to worry about them. I trimmed my pubic hair, so it formed a small tidy bush just around the base of my cock. I considered removing all the hair, but felt it looked better with just a small tuft.

Once I'd dried myself, I rubbed scented moisturiser into my legs and body, and carefully painted my finger and toenails a deep burgundy red, to match my dress. Once they'd dried, I took out my outfit for the night and lay it on the bed. I'd polished the cheerleader dress the night before, and it shone with a dazzling gleam. I also lay out my underwear. Along with a pair of tiny baby blue latex shorts, I took out my latex bra. The cups had been filled with a heavy gel, similar to silicone, that made them feel like the real thing. I put the bra on and instantly I had a magnificent pair of breasts tipped with rubber nipples. They weren't huge, but perfectly shaped. I could never usually resist playing with them, but this time I was too excited. My stomach felt like it was filled with a legion of butterflies. I gulped down a shot of tequila to try and drown them. 

I pulled on the shorts next, easing them up my legs and snapping the tight material into place over my butt. I tucked my half-erect cock between my legs and pulled the tight shorts up, hiding most of the bulge. The shorts fitted like hot pants, and quite a large amount of bum cheek showed. I looked at myself in the mirror, pleased with my transformation so far. I looked like a horny teenager in her underwear, my blonde hair falling around my face.

The socks came next, creamy white knee length socks that appeared to make my legs look longer. I polished my underwear quickly with a soft cloth and a can of spray. As I polished my crotch, my restrained cock jumped in my shorts, threatening to burst its latex prison.

Then it was time for the dress. Once more I pulled it up my legs and pulled the zip up my back, and I was enclosed in soft, sensuous latex. This time, the material stretched over the bra and formed an impressive bust line. it shone brilliantly in the late afternoon sunshine. I ran my hands over the dress, fingers skittering over the slick surface, smoothing out any creases and kinks in the latex, and enjoying the feel of my hands over my body. Turning around I could see that the skirt barely covered my bum, and my shorts showed every time I bent over.

Sitting on my bed, I pulled my new shoes out of their box. They were a pair of clear vinyl and perspex platforms with a five inch heel that I'd found in a shop up in the Camden a few months earlier, but hadn't had the chance to wear before. I pulled the shoes on over the socks and wrapped the straps around my ankles before pulling them tight and fastening them.

Walking over to the dressing table, I caught a glimpse of myself in the mirror. The skinny boy that I had been a few hours earlier had been replaced by a tall, willowy blonde in a tiny latex cheerleader dress. I smiled at myself, feeling comfortable with myself for the first time in a long while. I sat down at the dressing table and began to finish my transformation. I pulled my hair up into two short bunches above my ears, and secured them with two hair bands that had deep red baubles attached to them, like cherries. I applied foundation and then applied a lipstick the same colour as my dress. I kept my eye make-up simple; just mascara, eyeliner and a pinky-red eye shadow. I fixed a pair of gold hoop earrings in my earlobes and festooned my wrists with bangles and bracelets that jangled as I walked. I was ready.

I walked into our lounge at the exact moment that Donna left her room. I let out a whistle as I saw how she was dressed. In a dress that was almost an exact copy of Madonna's from the cover of "Like A Virgin". It was almost as if the Material Girl herself was in our apartment. She was a mass of lace and net, fingerless lace gloves that went up to her shoulders, lacy cut off stockings, white spike-heeled ankle boots and a halo of back-combed and curled hair. She'd got the make up exactly right, from the heavy eyelashes to the beauty spot on her top lip. "Bloody hell," I said. "You look incredible!"

It was a while before I realised that Donna hadn't moved or spoken. I walked over to her, skirt swishing around the top of my thighs and waved my hand in front of her beautiful face. "Hi. Donna? Are you in there?"

"Okay," she finally said. "I don't know who you are, you little slut, but what have you done with Chris?"

She kept a straight face for a couple of seconds, before letting out a whoop and hugging me. "You look incredible, babe. A proper little cheerleader! Gonna dance for me girl?"

"Give me a while to get used to these heels and you're on," I replied, blushing under my make up. "I look okay then?" I asked quietly.

"Chris," Donna replied, "you look more like a woman than half the women on this campus. Most would kill for legs like those. I know I've seen you dressed as a girl before, but this time I think you really mean it. So, what am I going to call you?"

"What do you mean?"

"Well, what's your name going to be? Candy? Lola? Peach-Blossom?"

"Um, I hadn't thought about it really. I suppose I still want people to know it's me under here. I don't want Chris to go away altogether."

"How about Chrissy then?" Donna asked. "You'll remember it when I call you from across the room, and it's still your name."

"Okay," Chrissy replied.

We sat drinking for a while, admiring each others outfits for a while, before Donna got up. "Come on, Chrissy. It's time for your big debut."

I felt the colour drain from my face. "Already?" I asked.

"Yep," she said. "It's nearly nine o'clock, the party should be well under way by now, and I said I'd meet Angie and the girls there, so get your cute little bum off the sofa and out the door. There's no point chickening out now."

Eventually, she'd managed to propel me out of the door. It was a warm summer evening, and the sun was just setting. We walked across the campus to the hall on the hill. As we went, cars filled with lads followed us, calling out and whistling to us, asking us to show them our tits. I felt both petrified and horny at the same time. These boys thought I really was a girl. Donna smiled at me. "Work it baby, you know you've got it going on!"

We linked arms and kept on walking. I tried to walk like the girls on the catwalk, placing one foot directly in front of the other. It was a good thing I had worn heels around the house for many months and I was fairly confident on my five inch heels.

We shortly arrived at Radley Hall. A group of people were outside smoking, dressed as everything from bums to cowboys, French maids to vamps. They turned and looked at us. The cowboy walked up to us and tipped his stetson back on his head. "Evenin' ladies," he drawled in a terrible accent, looking us both up and down. "Come on in, the party's jus' gettin' started. And I'm sure you two know how to ride a buckin' bronco, if you know what I mean."

Donna elbowed me. "I'm sure I'll look you up later, cowboy," I said, inspecting his sheriffs badge. 

"I'll be right here, ma'am," he replied, holding the door open for us. The party itself was in the main lounge of the hall. A DJ booth was set up on a stage, and was pumping out some eighties dance music. Immediately, Donna and I started dancing, writhing up against each other. Soon more people were joining us as the music filled us. Boys pushed in between us and separated us. Soon I was dancing with surfers, astronauts and even a bullfighter. Hands were touching me, squeezing my butt, caressing my waist, and I was getting hotter and hotter. 

After about an hour, I headed for the bar and got a beer. I leaned against the bar and drank deeply from the can. I could feel sweat trickling down my back, collecting under my latex shorts and running down my thighs. As I looked over the now jumping dance floor, I noticed a group of Reservoir Dogs over in the corner, staring at me. I recognized them as being members of the rugby team. 

Draining my can, I walked through the crowd to them and started to dance in front of them. I wriggled and gyrated, bending over and showing them my latex covered butt under the short skirt. I moved closer to the lead Dog. His name was Dan and he was over six foot tall, and built like a brick shit-house (as my father would have said). I grasped his black tie and shimmied down his body, feeling his growing erection under his suit trousers. I writhed against his body, using all my best pole-dancer moves. The other Dogs stood and watched, some with their mouths open. After a few minutes, when Dan's dick was straining hard against his suit, I stood up and walked away, back through the crowd.

Glancing over my shoulder, I noticed that the Dogs were following me. Smiling to myself, I pushed through the party people and walked down one of the corridors leading off the lounge, swinging my hips like I was on a catwalk. The Dogs kept following, all five of them. 

I walked into the laundry room, deserted at this time, and sat crossed legged on one of the washers, swinging my stiletto heel. Soon the Dogs entered the room. "Hi boys," I purred. "Looking for something?"

Dan nodded to one of the other dogs, who closed the door. "Well, aren't you a cutie?" he said. "Dancing like that might give people the right idea - I hope you can help me out with a small problem - well, actually, a large problem?"

"What did you have in mind?" I asked, wriggling off the washer and walking over to him. "Maybe this...?" I reached down and grasped his cock through his suit. It was rock hard and felt big, over seven inches long.

"That'll do," he said. "For starters, at least."

I didn't need any further encouragement. Sinking to my knees, I pulled down his flies and reached into his trousers. I grasped his cock and pulled it free from his boxers. I was right. Not only was it long, it was thick as well - I could barely close my fist around it. I smiled and licked my lips.

Pulling back his foreskin, a clear drop of precum leaked from his eye. I bent my head to it and licked it, savouring the thick salty taste. A small moan came from Dan's lips, and I carried on, licking his red helmet while gently stroking his thick shaft. I couldn't wait to get this monster inside me, but I thought Dan needed a little more encouragement. After all, how would he feel when he knew I had a dick too?

Licking my red lips again, I took the whole of his helmet in my mouth. It was huge and soft, like a large meaty marshmallow. I swirled my tongue over his shaft, sucking gently. My hand moved up and down his dick, squeezing and stroking him. 

After a few minutes I decided to try to deep throat him. By now his shaft was leaking what seemed like gallons of precum. I swallowed deeply, enjoying his taste, and gradually move more and more of his dick into my mouth. His shaft stretched my lips as it pushed past my teeth. Gently I eased more of him into my mouth, but gagged slightly as his huge helmet touched the back of my mouth. Swallowing fiercely, I pushed further, the fingers of my right hand squeezing and massaging his hairy balls.

Before I could get used to his size, Dan grabbed the back of my head and started to fuck my mouth savagely. His dick pushed further and further into my throat, but I loved every second. This big stud was using me like a piece of meat, and it was turning me on incredibly.

I opened my eyes and noticed that all the other Dogs had their dicks out and were stroking them, turned on by the sight of this latex cheerleader going down on their leader. I reached out and grabbed the nearest cock and tugged hard at it. Soon, my other hand was similarly engaged. 

Before he came, Dan pulled away from me and signalled to the other Dogs. Eight hands grabbed me and hauled me onto the bench in the middle of the room. They lay me on my back and pulled my legs apart. My skirt fell around my waist and revealed the tight latex shorts. My heart was thumping, worried that this fantasy would be ending prematurely.

"Very nice, cheerleader," Dan said, taking off his jacket and tie, and unbuttoning his shirt, "but I want something else."

"All right," I said. "But, I must warn you, I'm not like other girls."

"Good," Dan said. "Come on lads, let's get those knickers off her, shall we?" My legs were lifted in the air, and my shorts were pulled from me. 

"Shit!" one Dog exclaimed. "She's a bloke!"

"What are you?" Dan asked. "Some kind of poof?" He seemed to be angry, but I noticed his dick was still hard.

"I told you, I'm not like other girls," I said. "But I can still give you want you want." I turned over and stuck my ass in the air. "Don't you want to fuck me? I want that hard dick of your inside my ass. Come on, don't tell me you don't like to give it to girls up the ass?"

"Nah, that's it," said one Dog. "This is too weird for me, I'll see you later." He zipped up his limp dick in his pants and walked out. Another Dog, who I recognized as Tom French from my English class, looked at me and then at Dan and followed his friend. Before he left, I noticed that he looked sadly at me and had trouble concealing his hard dick back in his pants.

That left just me and Dan and two other Dogs, who showed no signs of leaving. "Come on then," I said, looking over my shoulder at Dan. "This is a limited time offer here. And I want one of your dicks in my mouth too," I said to the other Dogs.

One of them sprang forward and lay down on the bench in front of me. His dick wasn't as big as Dan's, but it was still quite thick. I bent to my task quickly, taking his shaft in my mouth and sucking hard. As I sucked him, I felt my bum cheeks being forced apart, exposing my arsehole. I felt a saliva-lubricated finger push at the sphincter and relaxed my muscles, allowing the intruder access. More spit was dropped onto my arsehole which relaxed quickly to allow two, then three fingers inside my tight bum. I was glad I'd spent all those lonely nights with my dildos and butt-plugs now, so my arse was used to the invasion.


The Fancy Dress Party



After a hard finger-fucking, I felt Dan's dick nudging at my asshole, covered with a condom he must have had in his suit. The condom's lubrication helped him push himself inside me. I gasped as my sphincter stretched to accommodate his helmet, and had to postpone my cock sucking for a while. Once Dan's helmet was inside my arse I continued as he pushed further inside me. I was being stretched further and harder than ever before. My own cock was rock hard and leaking over the bench as I was being taken from both ends.

Dan's dick was being pushed further and further into me with each stroke. Each time I felt that he must be all in, but each time more of my ass was being filled with his large dick. Finally, with a large thrust that made me gasp and nearly choke on the dick in my mouth, he was totally inside me, his pubes scratching my bum cheeks. After a few seconds he began to thrust inside me, pulling his dick out nearly all the way, and then ramming it home hard. He pounded inside me harder and harder, while I sucked harder at the dick in my mouth.

Soon, the Dog in front of me couldn't hold back and he exploded, gasping as his cock filled my mouth with cum. I swallowed every last drop, drinking the thick liquid like a McDonald's shake.

As soon as he was done, the other Dog stuck his cock in my face. I carried on where I left off, enjoying yet another cock in my mouth. This Dog had obviously been jerking off in the corner watching me being double-ended, and he was close to coming. I squeezed his shaft at the base, trying to delay his orgasm. Meanwhile Dan was still pumping away at my sore bum. I was amazed he hadn't come yet, and similarly impressed at his control. 

I carried on sucking the Dog in front of me and soon felt Dan's orgasm building up in my ass. I doubled my cock-sucking efforts, trying to get the two of them to come simultaneously inside me. As it happened, Dan came first, grunting and giving two almighty thrusts inside me and then exploding, his cock jerking and bucking. The effect of these thrusts transferred to the cock in my mouth and the Dog came. I tried to swallow all his spunk, but couldn't, and it dribbled out of my lips and down my chin. He was still spurting as I pulled away, and my cheeks and hair got showered. 

I knelt up on the bench as Dan pulled out of my arse, leaving it wide open. The dress fell back down onto my hard cock, causing it to jerk and jump. I wiped the cum from my face and licked my lips, as some dropped down the front of my latex dress. I scooped it up, licked my fingers and smiled. "Right, who's next?"