tagTranssexuals & CrossdressersFulfilling A Girl's Male Fantasy

Fulfilling A Girl's Male Fantasy

bystarbelliedboy©

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, and we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up, so she invited me back to her place. It turned out that she was eighteen and still living at home, so we locked her door and did our best to keep quiet as we fucked the night away. Now it was noon, her parents were at work, she was on half term from sixth form college, I had the day off uni and we were in the sitting room. We'd both put on the same clothes we'd worn last night when we got up, and she'd removed her make-up, but she was still stunning, her hair a bit messy and her ample breasts squeezed into her tight black lacy v-necked vest top. She took my hand when I was done, picked up a bag she'd brought from her room, and led me on to the cold tiles of the kitchen.

"Now Jack," she said, kneeling at my feet and rummaging in the bag, "This is a fantasy I've had for a long time, so please let me do this. I'm going to shave you, so keep very still." She pulled out a razor and some shaving cream. Applying it to my left leg she quickly began shaving it with smooth, confident strokes. In no time my left leg was bare up to the hip, tingling, and she started on the right leg. That done, she turned me around to do my arse. I was quite enjoying all this, when she made me gasp in horror by plastering my balls and cock with shaving cream. Hoping she had a steady hand and keeping absolutely frozen still, I allowed her to shave my bollocks, the skin tight from the cold.

The slight stinging was helped by her squeezing my balls a bit for a while, as she shaved under my navel. Up she went, any body hair disappearing quickly, finishing with my cheeks and chin, so that I was as smooth as the day I'd been born. Jennifer wiped the remaining cream off with a damp towel and stood back to admire her handiwork.

"There," she said smiling, "you look good enough to lick all over." We returned to the sitting room, where she quickly stripped naked, throwing her knickers over my face so I could inhale the sweetness of her sweat and juices, and handed her clothes to me. "Now put them on, Jennifer. I'll be Jack." So she began putting on my clothes.

This was a new thrill, I thought, getting into her still warm black lace briefs, my stiffening cock poking out the top. Next I went for the black bra, and Jennifer gave me a bit of help, standing in my boxers, socks and unbuttoned white shirt, then gave me two little cushions to pad it out. While she buttoned the shirt and put my trousers on, I put on her garter belt and had fun putting on her black fishnet stockings, which felt nice on my bare skin. Jennifer admiring herself in the mirror, I got into her black mini-skirt, a snug and comfortable fit, although it restricted my movement a little, and then finally the vest top, which didn't feel too strange with my shaved armpits.

A bit of adjustment to my fake tits and I thought I was done, but then she brought the finishing touch: a pair of high-heeled stiletto shoes. I put them on and walked about, wobbling at first but soon swinging my hips like a good slut, making her giggle. We kissed, Jenny on tiptoe to reach my new height. She sat me down in an armchair, and got out some make-up. Delicately, she applied dark red lipstick to my mouth and outlined my eyes with black eyeliner, so that when I looked in the mirror above the fireplace I could see that she'd given me her goth look.

Again we kissed, this time for longer and more passionately. Her hands moved to my legs, moving up the stockings, under the skirt to squeeze my buttocks. I untucked the shirt to slip my hands around the soft flesh of her waist. My lips moved down her neck, her head thrown back, and I found myself undoing my own shirt to get at her breasts. We kissed again, my hands cupping the warm firm shapes of her tits, before I had to bend down to reach them with my mouth due to the high heels. Brushing the sides of the shirt out of the way, I kissed the sides, sucking and licking gently at the undersides and between them, teasing her until she grabbed my head and pushed it on to her right breast. Taking the hint, I began sucking on her nipple, gently pulling and nibbling at it with my teeth and flicking my tongue over it until it was hard and erect. I shifted my attention to the left nipple, rolling the right between my thumb and forefinger.

Once her nipples were nicely stimulated, she covered them with the shirt again and pushed me down on my knees, my face now at crotch level. I undid the flies of the black trousers and pulled them down to her ankles, followed by my boxers, the smell of my own sweet sweat starting to mix with that of hers. Faced with a gorgeous unshaved pussy, there was no doubt in my mind about what I had to do. Slipping my arms between her legs to reach her buttocks, I pulled myself towards her and began peppering her inner thighs with kisses, working my way slowly up towards her slit. I licked around the entrance and deposited a large glob of saliva in her dark brown pubic hair just above her clit, watching it roll down over it and mingle with the juices of her glistening cunt.

As it formed to drip off, I held out my tongue to catch it and then slowly licked up her inner lips, pushing it inside her but keeping the speed agonisingly slow until she twitched with anticipation. Reaching her clitoris, I licked around it and under the hood, milking suspense for all it was worth. The circles my tongue was making gradually zeroed in on her clit, so finally I was burying my nose in her bush, sucking and licking, making her moan. Hungrily, I lapped and sucked at it, then dove down to stick my tongue in her hole, nibbling at the lips with mine before returning to her clit.

Jennifer moaned and whispered to me, caressing my head. To anyone looking through the open curtains though, it would appear that a shorthaired brunette goth was deep-throating a short guy with long brown hair. As her legs began to wobble, she shuffled back pulling me with her, and fell into an armchair. Here I could more comfortably eat her out, and moved my left hand to stroke her stomach and my right to insert a finger into her. This allowed me to concentrate on licking and sucking her swollen clitoris while I finger-fucked her. Within a few minutes her moans turned to cries of ecstasy as she climaxed, secreting more and more juices, soaking my hand and running down my arm. I redoubled my efforts and added a second finger, which before long yielded a second orgasm, and then more. Finally, after over twenty minutes she became too sensitive, so I stopped, a little relieved as my tongue was feeling a pretty tired.

Getting up off my knees I straddled her lap, resting my bare buttocks on her bare legs, the fishnet and high heels at my ankles touching them at the edges too. Jennifer took my wet face in her hands and kissed me on the lips, thanking me, and for a while we hugged and kissed, her hands caressing my arse and the lace that divided it. I was almost painfully erect now though, and was wondering when she would return the favour. I needn't have worried.

Soon she began to squeeze my balls gently and to run her thumb and forefinger up and down my shaft through the material of her knickers covering them. Once she'd fully recovered from her orgasms, she asked me to stand up, and immediately knelt between my legs. Lifting the front edge of the black mini-skirt to tuck it into the waistband, and pulling down the front of the panties, she pulled my erect cock and balls out. Immediately she set about licking my hairless scrotum, taking each testicle on her tongue and allowing it to roll off, then licking repeatedly between them, leaving a glob of spittle on them. Her big brown eyes looked up at me as, her tongue extended, she caught the saliva dripping off and then slowly sucked each of my balls into her mouth individually, her chin shining with her own dribble. With both in her mouth, warm and wet, being sucked on and teased with her tongue, the feeling of the hardness and sharpness of her teeth lightly touching the skin of my sack just below the base of my dick reminded me that I was at her mercy.

Presently she widened her attention to the base of my shaft, licking around it and the skin just above it where previously a thick mass of pubic hair had grown, never allowing any area of skin that she had wetted to dry. I became aware of her hands, stroking my stockinged legs and bare cheeks, occasionally slipping between them to rub the material over my anus, or to caress my unslobbered penis lightly with her fingertips. This was quickly running out with Jenny licking and sucking her way up, though not fast enough it seemed to me, being driven mad with anticipation, running my hands through her long brown hair. As she neared the head she pulled the foreskin back and forth over it, then she was sliding the tip of her tongue around the edge, licking the head itself, flicking the tip of her tongue over the little slit.

If I had not cum twice in the early hours I'm sure I would have with what she did next, though as it was I was a long way from it. She simply sucked the entire head into her mouth, sucking hard whilst swirling her tongue around it again and again. Then with a pause for breath, she put her tongue under it but pushing up so that the top of my cock touched the roof of her mouth, and sucking harder than ever took more of me into her, until I almost thought she was going to deep throat. However, she pulled back slowly so only the head was in, and sucked me in again. She did this slowly twice more, and then another three times quickly before she ran out of breath and released me.

Once again she licked and sucked all over my balls and cock before giving me the full blowjob again. After the second lot I shuffled over to the sofa and sat down while she carried on with it, now giving me a gentle wank when she wasn't sucking on the end of my knob. Each time she did, she did it for longer, moaning to add the vibrations to the intensity, squeezing my balls at the same time, so that my pubic skin, her knickers and her chin were all soaked in her slobber. Nearly ten minutes in and she forgot about licking the rest, concentrating on the head with her bobbing and licking, sometime everything, sometimes just the tip, whilst massaging the shaft and balls with her hands. For my part, I could feel an orgasm coming on, closing my eyes and bucking my hips to encourage her, the movement of my hands on her head less under my control. Just as I could feel myself reaching the point of no return, Jenny stopped and pulled back completely, the orgasm fading but for a small stream of precum that she daintily licked up.

"I don't want you cumming just yet Jennifer," she said smiling. "Now, you've been very good so far in wearing my clothes. I wonder, would you go a bit further?"

"In what way?" I asked, intrigued.

"Well," she began, evidently finding it awkward. After a pause, she finished. "I want to bugger you. Sorry, that's a silly way to say it... I want to fuck you in the arse with a dildo. Apparently it's even more fun for blokes than girls, and I love it! So, will you let me?"

"Of course," I replied, obviously to her surprise. I explained my bisexuality, and she seemed pleased. Returning to her bag she pulled out a big strap-on fleshy coloured dildo, which she put on, and a tube of KY jelly. She came towards me, the seven or eight inches of nearly two inch thick pink dildo poking out from the ends of the shirt towards me, the black trousers around her feet forcing her to shuffle. Taking the tube from her I lubricated the fake prick liberally and passed it back to her, getting down off the sofa on to my knees facing it and leaning forward on my elbows. Looking at the cushions in front off me I felt her pull the knickers aside, almost hooking them on my arse cheek, then smearing the cold jelly around my anus, her finger slipping in and twisting around, followed by the click of the cap closing on the tube.

Now I could feel the sliminess of her fist covered in lubricant pressing into the soft flesh around my forbidden hole, in the centre of which she held the cold tip of the dildo. The front of the skirt had become untucked and hung down with my limp genitals, while Jenny lifted the back up and out of the way with her free left hand, which held my hips just under the garter belt, preventing the skirt from falling back. Carefully, she pushed forward at the same time as I relaxed and tried to push my muscles open, and the head of the dildo squeezed through the ring of my sphincter. I gasped at how good it felt, and pushed back to meet her, more of the dong sliding in over my prostate, eventually feeling her skin meet mine to indicate it was all the way in. My arse ached a little, but I soon ignored that as she began to thrust in and out, and before long I was groaning in pleasure, even clenching myself tighter around the fake cock as it pumped in and out.

Jennifer really started getting into her role, pounding like she was some guy fucking a slut in a porn movie, calling me a whore, pulling playfully at my hair and slapping my cheeks occasionally, telling me to beg for it. After a while though, she became bored of this position, and pulled out, ordering me to lie on my back on the floor and pushing my legs up and back until they almost reached my shoulders. Kneeling down, she reinserted the dildo, and then leant forwards over me, screwing me missionary style while I wrapped my legs around her back, pulling her closer to cup her breasts with my hands, straining upwards to kiss her. My cock was erect again, and sticky from all the precum that was being produced by her fucking, but although I was really enjoying being her slut, I needed to have an orgasm soon or I might go mad.

Thankfully, she was becoming bored with being the man, so she stood up and started taking the strap on off, while I got out of the vest top, skirt, knickers and stilettos. "Right Jack," I told her, and she giggled as she slumped down on the sofa, now only in my shirt, ready for me, "It's your turn to be fucked." I spread her legs and slipped my cock inside her wet pussy. We began fucking in hard and fast, as I knew I couldn't last much longer, Jennifer fingering her clit with one hand while with the other she held my thigh, still in her fishnet stockings. I leant down to suck on her tits, and she began moaning again, but I felt myself near an orgasm finally, and told her so, pounding her cunt faster still.

"Cum in my mouth!" she gasped, so as fast as I could I pulled out of her, her fingers still working to pleasure herself, and climbed up on to the sofa. I wasn't quite fast enough though, as the first spurt splattered on to her breasts, and the second streaked over her cheek, but then she took me in her mouth and caught the rest, while I stroked her hair in gratitude, her tongue working to prolong my climax for as long as possible until I began to soften up. I slid down next to her, completely spent, and just kissed her while she slowly brought herself to another, final orgasm, then sat together, leaning on each other for support until we could muster the energy to get to the shower.

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