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My Best Friend

"My friend's reaction to me dressing as a girl caught me by delightful surprise."

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Famous Story
I always wanted to be a girl.

Every time I saw those pretty girls prancing around the college campus I’d become green with envy. Their feathery skirts caressing glossy thighs. Long, silken hair cascading across bare shoulders. High heels clicking on the pavement as they paraded their fit asses in front of all the guys. They were allowed to be sexy, and no one would stop them. And the warm summer days would convince even the most careful girl to parade her body.

In my mind I used to fantasize about being one of them, feeling the sheerness of silk and coarseness of lace slide along my naked body. When I finally decided to stop imagining and rather do something about it, it felt like something I should have done ages ago. Access to online clothing and lingerie stores was immense, and I felt like a child in a toy store. For every accomplishment at my studies, I would treat myself to a little online shopping spree. Once every week I would find an opportunity to indulge all by myself. Although every night ended with a joyful release, that wasn't the most important aspect for me. What I enjoyed the most were the fantasies, and the slight sense of reality the clothes applied to them.

The transformations themselves weren’t all that hard. All my years of fantasizing had kept my mind correctly attuned, and movements and attitude came easily. I had never really been a masculine boy, and when I let my hair grow, took good care of my body and expertly applied make-up, it wasn’t difficult to pass as a girl. When I looked in the mirror my eyes saw only the pretty girl I wanted to be, and not the subtle hints that gave me away as a boy. Over the weeks and months following, I became quite adept at changing my appearance. I was happy with the way I looked, and every day, as I came home to my dorm room, I would rush to the ever-more-crammed closet and change into some of the daring clothes I had stashed there. Every day a different outfit, and every time feminine and sexy.

As time passed, I wasn't merely satisfied with doing this in secret. I needed someone to confide in. Someone I could trust with my life. There weren't many to choose from. I only had one true friend; Dave had been my pal since childhood, and we'd shared every experience together. We even ended up applying to the same college.

When I confided in him, he laughed straight into my face. I instantly turned grey as a ghost, but he saw my expression and eased my terror.

"I know, I know. This is a serious matter for you. But do you really think I haven't suspected? You've let your hair grow out, and now it's glossier and softer than any of the girls on campus. Your long fingernails are somewhat of a give-away. Your sudden refusal to shower at the gym wasn't all that subtle either. But your biggest blunder was that time you forgot to hide the make-up in your bathroom."

I was at a loss. My embarrassment was obvious as I felt heat rise up my cheeks.

"Don't worry. Why should it bother me? You haven't noticed that I knew before, so why should anything change now? Go on. Get back to your room and change, then I can come over later and we'll watch tonight's movie like we always do. Then you'll realize that nothing has changed. You're still my friend, girl or not."

Stunned, I simply turned on my heels and went back to my room. I couldn't believe how easy that went! The thrill and relief of finally having someone to confide in was immense. Hurrying to my closet once more, I was determined to test my newly found confidence and put on my best performance.

I felt somewhat overdressed, but I knew that I needed to look my very best. After all, the desire to feel feminine was the main reason I enjoyed this. I was wearing a short, black skirt that covered the upper part of my thighs and the broad lace band on my stockings. The bottom hem was ruffled with lace, and the satin details shone in the lamplight. The stockings were held in place by a girdle with four garters.

If I hadn’t been sitting with my legs crossed, my tiny thong could easily have been seen covering the closely shaved crotch. The corset I chose had numerous black and red silk ribbons and lace details, making me feel like a Victorian lady. The breast forms were difficult to conceal, but I managed nicely enough by wearing a puffy, white blouse underneath the corset. My shoulders and neck were soft and naked above the tightly-laced upper strap of the blouse. A tight necklace with a large brooch at the centre of my chest completed the look.

The movie was quite long and boring. The dim light and soothing heat of the summer evening slowly made me dozy, and as the film was nearing its end I was fast asleep, leaning my head on the soft cushions. I slept through the end of the movie, and as usual my head filled with erotic dreams where I really was a girl. They were so life-like that I could almost hear the sounds I made as I was fucked in my pussy and driven towards orgasm. First a slap, then my high-pitched moan, followed by the slower, deeper grunt of my lover.

Suddenly the dream vanished, and with regret I noticed the images in my mind fade away. The strange thing was that, as I came to myself, the sounds never vanished. I could still hear myself moan with each thrust. My lover’s pelvis was hitting my ass with a sound like clapping hands.

I opened my eyes and found myself back in my room, lying against the pillows on the couch with Dave at my side. Before us, next to a tall mirror, was the telly. A glimpse of rapidly moving flesh on the screen caught my eye. A beautiful girl was sitting on her knees on a bed with a pair of strong hands forcefully gripping her hips. Her lover pounded his lower body against her rear. The large, unnaturally firm breasts rocked back and forth in opposing tune with the couple’s movements.

What surprised me most was the realization that the girl on the screen was in fact not a girl. While supporting herself on one hand, the other was between her legs jerking a large, erect cock. This made my comparison with her even more real, and I felt a strong surge of arousal rise up through my body from somewhere deep down. I imagined myself sitting on my knees being fucked in the ass whilst jerking my now rapidly-growing penis.

My short skirt lifted slightly under the movements of my member, and I glanced shyly to the side to see if Dave would notice. Like me he seemed fully preoccupied with watching the wonderful scene taking place on the screen before us. He had his right hand below the rim of his pants, and I could see the crotch move rapidly as he touched himself. I was a bit shocked. He was enjoying this? He who was the archetype of male bravado.... he was aroused by watching a shemale being ass-fucked by a guy?

I didn’t quite know how to behave in this situation. If I moved, he would know that I had caught him watching this, and I didn’t want to embarrass him. Still, if I pretended to be asleep, things might get worse. I looked over at him again, and this time I turned my head with a yawn to make him aware that I was awake. He startled, his hand flying up from his pants, and I could see his eyes dart towards the remote that was lying on the couch between us.

“Don’t turn it off. I wanna watch,” I said. ”I didn’t know you too were into that sort of thing.”

He looked embarrassed and didn’t speak a word. I looked at him teasingly.

“Don’t be shy. I don’t mind you touching yourself. I’m equipped just the same way, you know. It just might not look that way. To be honest, I get quite turned on by the film.” I looked him in the eyes with an expression that could hardly be misunderstood. A little devil awoke in me.

Still he said nothing. He just stared into my eyes with a baffled look.

I moved a bit closer, knowing that he would smell my perfume, and I couldn’t help glancing towards the large bulge in his pants. It moved and pushed harder against the fabric as if it yearned to escape and stand tall and free before me. I knew that my words had affected him the way I had secretly hoped.

“Feel free to continue. Or shall I do it for you?”

I laid my hand on his belly, just where his shirt had been pulled up somewhat. The little strip of hair guided my hand down towards his still-closed belt buckle. He didn’t resist, just sat there looking at my hand on his abdomen, slowly sliding down past the rim of his trousers. His entire body was quivering, and I was unsure whether it was from fear or excitement.

The moment I felt the incredibly warm, hard surface against my fingers, I felt myself shiver exactly like him. With calm and steady movements, I began to stroke the length of his shaft.

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My own penis was completely erect and protruded far beyond the thin waist of my panties.

“Let me see you,” I whispered softly.

“Oh, man. That feels good.”

He lifted my chin to see me better. With my eyes firmly locked in his gaze, I nimbly undid his belt and fly before sliding his pants down.

He pulled off his shirt at the same time. Slowly, whilst still stroking his cock, I moved down to sit on my knees before him on the floor. Through the tall mirror beside the telly, I knew that he could have a clear view of my ass. The short skirt covered only the upper part of the closely shaven bum, and the tiny triangle of the thong covering my testicles was visible between the top of my thighs.

The couple on the screen took a break in their frantic fucking, and the girl got to her knees before her lover, in much the same way that I was already sitting. She grabbed the cock, ripped off the sticky condom and put the shaft greedily into her mouth, sucking with great energy. Loud sucking noises reached my ears as I watched Dave's eyes shift between me, the screen and the mirror.

I followed her example and bent forward, giving him a hasty kiss on the tip of his penis. The taste of the syrupy pre-cum was strong, and the penis head was glistening with several drops of it. I licked him again, trying to get as much of it as I could. Whilst still jerking him, I let my tongue slide over the split tip and down along the tight string below. He twitched as I touched the coarse area where the string met the soft skin. His eyes were fixed on the mirror, and I tried to push my ass back as much as possible to give him a clear view.

I took a break in the sucking to pull my panties off. They slid with ease down my shaven legs, and I teasingly tossed the tiny garment onto his chest before continuing my previous caresses. With my free hand I spread my ass and rubbed myself on the tight opening. Dave was paralyzed, staring at the mirror, and I knew that he silently wanted to penetrate me. To be honest, I yearned for him to drive his massive cock into me myself. I really wished to feel completely like a girl, and knew that being fucked by a man was the only thing that could make me feel truly feminine.

Touching my ass made me remember my own hard cock, and I began stroking myself fervently. The thought that he might soon take me from behind made me horny as hell. With rapid touches I approached orgasm much sooner than expected. I had little self-control left, but I made sure to allow him a full view through the mirror. As the climax came, I moaned loudly whilst placing my hand under the tip to collect all the semen.

The surge of sperm was powerful, nearly filling my palm. Careful not to spill too much, I raised my hand and emptied it over my ass, feeling the warm liquid slowly run down between the round cheeks, covering my imagined pussy. Fully lubricated, I began to push two fingers inside the hole. I had done so on numerous occasions and with many different objects, and knew how to stretch myself to accommodate something the size of a man’s cock. Jizz covered my fingers and made them slide easily in and out as I fucked myself.

Now that I had climaxed I came somewhat to my senses, realizing what I was doing. Still, I had no problem with it. I yearned to feel every form of pleasure together with my friend. I wanted to feel and make him feel as good as possible. While pleasuring myself, I had forgotten about his needs. With a new burst of motivation I continued my sucking with more energy. His lips were open, breathing heavily and moaning, happy to once again be the centre of attention.

I could wait no longer. My eyes turned upwards, meeting his gaze, telling him that I was ready. Still on my knees on the floor I turned around and saw him through the mirror, staring at my glistening, lubricated hole.

“Please, Dave. Please let me feel your huge cock. I want you inside my pussy. Please.”

I begged him with my voice, eyes and ass, leaning down towards the floor feeling the carpet pressing against my cheek. The position opened my buttocks and showed him what was waiting for him. I felt the chill draft in the room brush against my wet cave, covering my fit bum with goose-flesh. My body was quivering with anticipation, and I braced myself for the awaiting moment.

Without touching me with his hands, he steered his rod against the gaping mouth, and I whimpered as the head of the penis, glossy with pre-cum and saliva, touched me. I wiggled my ass a bit, making him rub against me before pushing backwards. The feeling as he increased the pressure, slowly entering my asshole, was like nothing I had ever felt before. The warm, pulsating sensation of his hard flesh was so much more stimulating than the rubber dildos I’d used on myself.

I tried tightening my rear to prolong his entry, but his pressure was greater than my resistance. With a scream I lost the struggle and felt his penis enter me. He didn’t go all the way in, and slowly pulled himself out again whilst making unmistakable sounds of pleasure. Before entering me again, he waited for a few seconds, allowing me to get accustomed to his girth. The moment seemed like an eternity, but I could do nothing except lie panting on the floor and wait.

Pleasure surged through my body as he once again entered my ass, now more lubed by my semen and sliding further in than before. He retreated and went in for another try, and this time I could feel his abdomen reaching my behind, and his balls touching my own. From this moment on, as he took me again, he increased the speed and force of his movements, making us both cry out in pleasure with each thrust. His balls were now pounding against my perineum. The sticky sperm covering me made loud, slapping noises of raw sex.

I was thrown forwards each time he fucked me, and I loved the feeling as he slid through my opening with just a hint of resistance before reaching all the way inside. His hands held on to my hips, boring his nails into my skin. Neither of us took any notice. The pleasure and ecstacy we both felt fully occupied our minds and bodies, driving us nearer and nearer the edge of climax.

Finally, as I was rocking back and forth, adding my own movements to his thrusts, he stuttered out from between hasty breaths that he was about to come.

“Yes, come! Come inside me! I want to receive your load. Take me and do whatever you want with your girl!”

This was all he needed to let go. His movements were frantic and driven by sheer lust as he let loose his orgasm and rammed me, reaching further in than he’d ever been. I could feel how his crotch began a series of rapid pulses, driving the semen through his cock and releasing it within me. The feeling was incredible. Knowing that a strong man came as he had sex with me was on its own enough to bring me to the brink of yet another orgasm.

His movements inside me continued for several thrusts. Knowing that I had pleasured him greatly allowed me to focus on my own pleasure. My hand slid along my flat chest and reached the thoroughly shaven area between my legs. With my fingers I traced the crack just above my balls, touching his shaft and feeling how he vanished inside my hole. I began stroking my own cock, bending my head down to watch myself and to see for myself that he actually was inside me. Shortly thereafter, my own rod twitched before sending a powerful surge of hot, white semen out from the end. It crossed the gap towards my face, hitting me several times over on my lips and chin. I had tasted myself before, but never got tired of it. I readily licked my lips and felt the semen inside my throat as I swallowed.

The orgasm seemed to draw every ounce of energy from my body, releasing it in an orgasm more powerful than the last. My ass tightened rhythmically around his shaft, and I could hear him reacting to the sensation with delight.

At the same time, the room resounded with high-pitched screams from the telly as the shemale came and shot her load all over her own belly and tits. I could recognize my own climax in her and knew that I would never again watch porn without thinking of this wonderful adventure.

He was still standing on his knees, shivering with strain. Sweat was running in small streams down his forehead and torso. I turned around and smiled the widest, most natural smile possible. The childish girl in me took over and laughed with joy as I threw myself at him against the couch. My lips embraced his own in a long, passionate, wet kiss, loaded with sheer affection. Today, I had showed him how much I appreciated his understanding. I guess some things had changed after all.

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Written by Dividence
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