tagTranssexuals & CrossdressersFulfilling A Girl's Male Fantasy Ch. 02

Fulfilling A Girl's Male Fantasy Ch. 02


*Note to readers: This is a sequel to my other story "Fulfilling A Girl's Male Fantasy", also in the 'Transsexuals & Crossdressers' category.*

Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a couple of months after our first encounter, we were both in her room talking and listening to music.

"Kat's having a party next weekend," she told me. Katrina, Kat for short, was one of her friends, who I got on with pretty well. "Will you be able to come?"

"Yeah, of course." I replied.

"Her parents will be away," she continued, not looking at me and starting to fidget with the carpet, "so we were talking about what we could do, and..."

"And what?" I asked when she came to a halt and began toying with her new tongue piercing.

"And... well, they know about, you know, what we do together..."

"Who's 'they?'" I asked, not really particularly joyful about the idea of all her friends knowing about me wearing her clothes.

"Oh, don't worry, I haven't told everyone, just those I really trust..." She still wasn't looking at me.

"Who?" I said, relieved, but curious anyway. I trusted her not to have told everyone if she said she hadn't.

"Just Katrina and Sophie. And Chandice. But no one else! They all get kind of turned on by guys dressed as girls too, you see..."

"Right, OK," I said. "So what was the idea for the weekend?"

"You don't have to do it if you don't want to you know, I'll understand," she said. I kept looking at her, waiting for her to finish. She took a deep breath and then said as fast as possible "Will you dress up for us four? It'll just be us, and then, you know, we can do our thing, they can watch, maybe join in..."

"Join in?"

"Well, if you don't want them too I'm sure they can do it themselves. Or with each other in Sophie and Chandice's case..." Sophie and Chandice were bi, and openly going out with each other, which caused them a bit of trouble at college, but they didn't seem to care.

"No," I said, after thinking. "No I don't mind if they join in. It could be fun a guess... Yeah, I'll do it." This earned me a hug and a kiss that knocked me back on to the floor, and then something more...

So the following Saturday Jennifer shaved me once again, and gave me the full beauty treatment of lotions and all sorts, jerking me off so I would last longer later, even giving me a dose of perfume, before we left for Katrina's house by bus. Luckily no one noticed that I was wearing perfume as my girlfriend wore the same and sat next to me. Although it was still fairly light, the curtains were drawn when we arrived, heavy metal playing fairly audibly as we rang the bell and were ushered in quickly by Jenny's friend.

My eyebrows raised and jaw dropped when I saw Katrina: I normally thought she was quite pretty, with a petite figure to rival Jenny's, but that night she looked stunning. Her very short, jet black hair was gelled up in spikes apart from the fringe sweeping down across the left of her face as usual, she was wearing a ring in her left nostril, big hoops in her ears and a tongue stud, but other than that she looked completely different. Her clear blue-grey eyes had heavy eye shadow, eyeliner and mascara along with black lipstick, then continuing the goth theme a dog collar with spikes that looked about two inches long, a metal spiral around her upper arm in the shape of a snake, then a black PVC bra to show off her pierced navel and the tattoo below it, with tight black lace up PVC trousers, making it clear her had no underwear on, with high heeled boots to complete the outfit.

"Wow Kat," I said, "you look gorgeous."

"Thanks Jack," she smiled. "Or Jackie, as you will be for tonight. Come with me, I'll help you get changed, and Jenny needs to as well. Did you bring the stuff Jen?"

"Yep, it's in here," she replied holding up the bag I'd not been allowed to look in. We went upstairs into her room, and I began to undress while the girls got out the clothes they wanted me to wear.

"Oh, don't be silly Jack," Katrina told me when I stopped at my boxers. "I'm going to see it later anyway." Reluctantly I pulled them off, but kept my parts hidden from her view despite what she'd said, and quickly got into the black lace briefs they had selected for me. Next on were a pair of black stockings with elastic tops so I didn't need suspenders, and then a bra, which Jenny filled with the small firm cushions we'd made to give me a vaguely realistic bust. The rest of it was a French maid's dress that showed my shoulders and cut away at the back, black with white frills around the edge and a white apron over the front of the very short skirt. I gave a little twirl for the girls and then sat down at the little table to let Katrina do my hair and make-up, while Jenny got changed into her outfit.

"Where are Sophie and Chandice, anyway?" I asked.

"Oh, I forgot to tell you," said Katrina, not entirely believably. "They've brought another friend, I hope you don't mind, they promised she can be trusted."

"Only one?" I asked, a little annoyed at having to perform for a stranger.

"Yeah only one. She's very nice. They're getting changed in my parents room and will meet us downstairs." Jenny had joined me at the table, putting on a little eyeliner and some dark red lipstick. She looked fantastic too, her hair all down and wearing a red and black corset that pushed her beautiful breasts up, a very short black mini-skirt with red trim, black fishnet stockings with the suspender straps clearly visible under the skirt, and some bright red, very high heeled shoes. All this came with a spiky dog collar and bracelets, all though the spikes were a lot shorter than Kat's

"You look amazing darling," I told her, and she grinned.

"So do you my sweet," she replied, mocking me a little, and stood up to attach the maid costume's headpiece to my newly gelled and styled hair. "Put your shoes on and I think we're ready." I did, slipping into the shiny black small-heeled shoes they'd got me, and all three of us carefully made our way down the stairs to the living room where the fun was to take place.

"It sounds like the others are already there," Kat said as we heard giggling, and she opened the door. "Everyone, this is Jackie."

A blanket had been laid out in the middle of the room, and on the far side sat Sophie and Chandice. Sophie was a little taller than her friends, and a little fleshier, which she was occasionally a bit anxious about, but I actually found her thick thighs and slight belly something of a turn on, and anyway they were more than made up for by her large E size breasts. She had long, bleached blonde dreadlocks, a nose stud, about three earrings in one ear and a whole load in another, as well as a pierced tongue and a ring through the right side of her bottom lip, today even more obvious as she had put on black lipstick to go with the heavy black eyeliner around her green eyes. I also knew she had a long tattoo down the length of her arm, and Jenny told me another large one on her back, but for the moment these were hidden as she had dressed in her old school uniform, her bust straining at the barely-fitting white blouse with green and yellow tie, and the top of her thighs that were not covered by the white elasticised stockings she was wearing, and in fact her white knickers, were not entirely covered by the short green and yellow tartan skirt.

Chandice her girlfriend was almost as tall as her, but thinner and had Jamaican parents, so she was very dark skinned, with her hair cut to about chin length all around except her fringe, and dyed alternately red and left its natural black, to make stripes around her head. She had studs in both ears, a ring in the upper part of one, a pierced tongue (they'd all gone to get their tongues done together), and a stud in the centre of her bottom lip, which wore white lipstick, outlining her eyes with white eyeliner, and even her nails were painted white, forming a kind of negative image of her friends. This was especially true compared to Kat, as Chandice's outfit consisted of white vinyl front zipped hot pants with matching cropped jacket, the single button all that held her tits in, and white go-go boots.

However, neither of these were what caught my eye and caused my jaw to drop. Who did was the person with shoulder length blond hair dressed in a sexy white nurse's uniform, because despite the bulges on the chest and totally clean-shaven face, it was unmistakably their friend Nick. I turned to Jenny in shock, although I noticed Nick was doing the same to the two girls behind him.

"Come on Jack," my girlfriend said. "You're bisexual, so is he. And we'd like to see you together. You can walk away if you want though..."

"No, it's just that..." I began, then glanced at him again. He really did look good in that outfit, and I hadn't been with a guy since before me and Jenny had got together. So the end of my sentence was a bit mumbled: "I just wish you'd told me that's all."

"We had to have a bit of fun and surprise though, didn't we?" Katrina said grinning and leading me to the centre of the room where Nick was standing. "Right, for tonight this is Nicola, Jack, and Nick, this is Jackie. Don't be shy guys, and we'll reward you." She stood back and there was silence, until one of the girls yelled: "Kiss then, lesbians!" and they all joined in. Awkwardly we put our hands on each other's waists and shoulders and leaned forwards, our lips meeting. It wasn't much at first, but I started to go a bit more passionate, and he reciprocated, pulling me closer, all our reservations disappearing as we let our desires take over, exploring each other's male bodies squeezed into women's clothes.

Nicola began kissing down my neck, her starched nurse's cap brushing against my face, so I was able to have a peek at what the real girls were doing. They each now had a few toys, some of which must have been in Jenny's bag, including as far as I could see three strap-on dildos, but they all seemed to be getting very excited at our antics. As we both sank down to our knees, I saw Sophie, who had been shaking her legs more than any of them, give in and lift up her skirt to slip her hand into her big white knickers. The others seemed to be about to follow suit, but at I stopped looking and turned my attention to the nurse in my arms, kissing down her neck now, inhaling her perfume and moving down to her fake breasts, pushing her back a little.

When I raised my head once more, all the girls had started playing: Sophie was still sat with her legs spread, using her fingers; Chandice had half unzipped her hotpants and was holding in what I assumed to be one of those little egg-shaped vibrators with her middle finger, the wire leading to the speed control in her other hand clearly visible on her black skin; Katrina was kneeling with her legs held together, the end of a silver torpedo-shaped vibrator sticking out from her PVC covered crotch, but from her expression as she watched us the vibrations were definitely getting through the plastic; and my own girlfriend was kneeling up, her legs spread a little, and was thrusting a large jelly dildo in and out under her skirt, where I assumed she had pulled the thong aside.

I was just watching Sophie reaching for a rabbit vibe when I lost my balance and fell back on to the blanket, Nicola on top of me, and our lips locked again. Moving my left hand down from her pert butt, I started stroking the back of her stocking covered thigh, slowly working up under the cotton and past the nylon to her warm, smoothly shaved flesh, then even further to her panties, rolling on top of her as I did so. We continued to kiss and fumble for several minutes, both getting hard from each other's fake femininity, the touch of each other through our clothes, and our friends' moans of pleasure and encouragement. However, our audience was getting impatient, and soon started to heckle calling for action, so I thought it was time I discovered what kind of equipment my lover for the evening had.

Sliding down to lie between her legs, covered by white nylon, and began kissing up her inner thighs as I liked to do to Jenny, at the same time pushing the white skirt up out of the way for when my face passed the top off her stockings, reaching her bare flesh, my cheeks brushing lightly against the suspender straps. Once I reached the lacy white briefs Nicola was wearing though, the sweet smell from the bulge beneath was unmistakably male, as I nuzzled into the cushion of her genitals, spreading her legs out more with my hands, seeking out the shape of the semi-erect cock beneath with my lips, and then peeling back the elastic waistband to release it. Nicola's dick was about the same size as mine, a little thinner perhaps, and circumcised unlike my own, but looked fantastic completely clean shaven.

I started with her balls, licking the smooth loose skin then taking each into my mouth, carefully sucking on them while holding her dick pressed against her stomach until I moved my mouth on to the base of her shaft and began slowly licking up it, enjoying my first taste of cock in months. Eventually I reached the head, and after circling it a few times, I took her into my mouth and eagerly sucked, feeling her get harder and harder, pushing my head further down so the tip pressed against the opening of my throat, trying to relax enough to swallow her. Nicola was moaning with pleasure from my attentions, her fingers stroking my hair around the headpiece and pulling me down on her. I was completely erect too now, getting excited from sucking her dick, and reaching back to rub mine through my panties.

Just as a little bead of precum leaked out on to my tongue, the real girls, who had been making louder and louder noises of appreciation, urging me on, decided that Nicola had had enough, and ordered us to swap. Reluctantly, I stood up and shifted around a bit so I was facing my girlfriend and Katrina who had moved closer together, and let Nicola kneel up and kiss up my legs, holding the short skirt and apron of my dress up out of the way so the other could see her as she moved closer to my crotch. While kissed over my thighs, I watched Kat and Jenny. Kat was lying down on her front, apparently with her vibrator still jammed between her legs, but as well as propping herself up on her elbows, she was resting her cheek on my girlfriend's thigh and stroking it with one hand and occasionally kissing it as she watch us in the middle. Her right hand was now holding Jenny's dildo, as Jen was still kneeling up but using both hands to rub her body and brush her hair out of her face, letting her friend do the thrusting.

The blonde nurse had now pulled my knickers down to around my ankles and was sucking my balls, pulling my foreskin back and forth over the head, then when she moved her tongue on to the shaft I couldn't resist looking down to watch, her bright red painted lips surrounding my cock and disappearing into her hot wet mouth. With her skirt down over her own erection, Nicola really did look very feminine, so still using one hand to hold my dress up I ran my fingers through her long silky hair, taking care not to knock her stiff white cap. Suddenly we were both distracted, Nicola stopping mid suck to glance sideways, as Sophie let out a shrill shriek. I turned too, in time to see her arching her back, her hips convulsing as she climaxed from the stimulation of the rabbit vibrator sticking out from her panties which she had pulled to the side to get it in her pussy, and Chandice pulled herself over to kiss her, moving awkwardly as she still had one hand in her very short shorts.

While us two fake girls were gawping at the real lesbian action, Kat and Jenny seemed to have decided it was time for some real fucking, and came into the middle with a big tube of lubricant.

"Eeny, meeny, miney mo," Jenny began, flicking her finger from one of us to the other, eventually landing on me. "Hey, Jackie, it's you're lucky night, you get to continued being the girl. Get you pussy nice want wet for Nicola."

I took the tube and pulled my knickers right off, and began to spread the thick gel around my anus, slipping a couple of fingers in as preparation, watching my girlfriend and Kat help Nicola out of her own knickers and her skirt, then made sure her dick was good and hard with they mouths. Jenny ordered me on to hands and knees, pulling the back of my dress up off my buttocks, and I felt her smooth hands on my skin, playfully slapping my cheeks, then two fingers of each hand were pulling my sphincter wide, and there was a brush of plastic against my other leg as Kat arrived to guide Nicola in. The nurse's legs touched mine as she kneeled behind me, and I sensed the tip of her prick against my entrance, the big event drawing Sophie, who had now also pulled off her knickers, to come and sit with legs spread in front off me, leaning back against her girlfriend knelt behind her.

Slowly, Nicola slid her hot seven-inch cock into my arse, and fuck was it good! Better than any of the strap-ons Jenny used on me, I hadn't realised how much I'd forgotten what a real one felt like. The two girls behind me moved away as the fucking got underway, and I could hear them moving around, but I didn't know what they were doing as I was concentrating on pushing back to meet Nicola's thrusts, moaning in pleasure. Chandice had begun playing with Sophie's breasts, while the latter had resumed fingering her clit as she watched Jackie the maid and Nicola the nurse fucking in front of her. The black girl undid the buttons on her girlfriend's blouse and pulled her bra down to get direct access to her large, erect nipples, kissing her bleached dreads at the same time, leaning down to nibble at her ear, until Sophie wriggled forwards off her with her legs on either side of me, her crotch almost level with my head.

"Come on maid," she said with a slight snigger, whilst moving Chandice around from behind to beside her with her hand on her vinyl covered arse. "Service me, you're our servant Jackie, just because the nurse is operating on you doesn't mean you can't continue your work." So as Chandice bent down to suck on her girlfriend's big breasts, I bent down to kiss her soft, wide inner thighs above her stockings, leaning on my elbows and trying to keep myself as still as possible despite Nicola pounding my arse. "Uh uh, Jackie, no need for preliminaries today," Sophie said, pulling me by my hair to stop the foreplay, and pushing my face straight into the dripping wet dark hairs of her pussy. She really was very wet from her playing before, but she tasted good as I licked over her swollen labia, a bit bigger and protruding further than Jenny's vagina lips, then up to her clitoris to a large sigh of satisfaction, although I wasn't sure if that was because of me or Chandice.

Once more, I was distracted by a cry of pleasure, but this time it wasn't the girl I was eating out, but a far more familiar voice, and glancing up I saw the source: Jennifer was on hands and knees next to us, her corset pulled down so that rather than just forming a sexy cleavage it was pushing her naked tits up. Behind her, Katrina, still fully dressed in PVC trousers was thrusting away like Nicola behind me, presumably wearing one of the strap-on dongs I'd seen earlier, although couldn't see it as they had positioned themselves so they could still watch. Turning back to attend to Sophie, I saw Chandice peeling off her white hot pants and straddling her girlfriend's face with her bald black crotch, leaning forwards towards me as she did so, her face close to mine while I inserted a couple of fingers in the other girl's vagina. She leaned further towards me and when I looked up she began licking Sophie's juices off my lips then we began kissing, until Soph stopped licking her pussy to complain that I was neglecting her, and Chan quickly pushed my head back into place.

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bystarbelliedboy© 4 comments/ 106522 views/ 13 favorites

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