Being Discovered
- I'd just turned 25 and was working for an advertising company in London as a copywriter. Great job, good salary and plenty of girls. I was quite slim with a good body and good looking in the David Cassidy sense, pretty rather than rugged. Still, I had no problems getting laid.
But I had another side; I'd been a crossdresser for as long as I could remember and I was never sure whether my excitement at the sight of a good looking girl was a sign of my heterosexuality kicking in or my need to put on her clothes!
I always looked forward to Fridays. After work, I'd go to a bar somewhere in the West End with a group of girls and guys from the office, have a laugh, flirt a little, maybe get lucky and bring someone home. But I didn't mind going home alone. My flat was modern and cool, set on the first floor of an old Victorian house in south London. Two bedrooms, stainless steel kitchen, wooden floors and Habitat furniture. It was a haven.
The first thing I'd do when I got in on a Friday was wax my legs if they needed it. I'd been keeping them satiny for years and waxing was now relatively simple and painless. I'd also make sure my chest and underarms were smooth and my fine arm hair was properly bleached. I'd shower down and then have a real close facial shave, then spend a while lying on the bed thinking about what to wear. After maybe twenty minutes, I'd sit myself at the mirror and do something with my hair. It was long in those days which gave me the flexibility to choose any number of feminine styles. I liked to comb it back off my forehead and hot tong it a little at the sides to give it some body and bounce. Then I might slide a couple of pretty clips in at the sides, or tie it back in a cute pony tail. I'd already be getting pretty excited and, when my dick was hard, I'd slip on a condom to save making a mess in my panties later. Next, I'd apply a little foundation, some mascara and eye liner and a subtle red lipstick. I've never been into over the top make up.
I'd built a hidden compartment into my wardrobe -- I never knew who might be staying over and didn't want to be discovered -- inside of which I kept my stash. Panties, pantyhose, slips, bras, tops, skirts and dresses. I loved to wear stretchy high leg, high front panties which just concealed the top of my erect penis. I preferred seamless bras because the sight of my smooth, bulbous silicon breasts bulging out into a stretchy Lycra top was overwhelmingly hot. My favourite top was green, with half sleeves and a low V neck which showed off my `cleavage'. Pantyhose were my favourites though. I liked them stretchy and fine, subtle not shiny, nude not coloured. Pulling them on was always the best part, rolling them into my fingers them unfurling them up my legs, slowly and sensuously so that I could feel the cum boiling in my balls. Then, I'd slide on one of my skirts, my favourite being a stretchy black mini, feeling it pop into place around my waist.
After that, I'd spend a while walking around the flat, feeling the clothes cling and move with me, my penis, wedged tight between my body and the panties and skirt, sliding around in the condom which was now lubricated with pre-cum. I would often spew a load just flouncing like this, staggering to a halt in front of the full length mirror and watching myself, bent over, hands on knees, like a woman taking it up the ass. Other times, I'd let it go on longer, maybe spending an hour looking at T-girl sites on the Internet getting hornier and hornier before spreading my legs wide and thrusting my hips up to milk the cum.
And that would be the pattern for the weekend, sleeping in soft panties and a satin slip, dressing in a variety of outfits and cumming incessantly. Sure, I'd go out some evenings, or spend an afternoon shopping for my `girlfriend' but I preferred not to break the dressing/cumming cycle till Monday morning.
One Saturday morning in spring, everything changed. I was dressed only in my satin bra, panties and pantyhose, studying a short flared skirt in my hands. I'd taken it into the better light of my hallway to check whether the cum I'd just spewed had made a stain on the front of it -- condoms weren't always reliable! Suddenly, I heard a voice at the door. It was Francesca, the girl who lived in the flat below. I turned, slightly startled, towards my front door and noticed that the letter box flap was up and light was streaming in from the outside hall, either side of Fran's head! I could see her pretty green eyes, wide open with shock as she stared at my penis jutting hard against the front panel of the panties. Oh shit. The flap went down with a snap and I heard her run down the stairs and slam the door to her flat firmly shut. What now?
I sat at the table in the kitchen trying to figure out what to do. Fran had moved in a couple of years ago and we'd hit it off straight away. She was tall, slim and quite beautiful and I know there was a frisson of sexual tension between us, but she had a boyfriend, Peter, and so we just became friends, always going out or staying in together during the week whenever he wasn't around. But now I'd compromised that friendship.
The episode had shrivelled my dick, but as I sat there distractedly stroking the fine silky material of the pantyhose along my inner thigh, it started to rise again and before long, I found myself lying on the bed, pressing it into the mattress before cumming into the condom in bucketloads. I got up, showered and threw on my male clothes -- jeans and T-shirt -- and, heart beating wildly, went downstairs and knocked at Fran's door. She didn't answer, so I called out until she came to the door.
She looked sheepish and embarrassed, but I put my arm round her and said, Ok -- I've got some explaining to do.' I told her that I was hetero, that dressing was something of a fetish and that lots of guys do it. I thought she was going to cry, but after a long pause, she smiled and said, Not you as well.' Huh?' Can you keep a secret?' She already knew mine, so I nodded. Of course.' Peter's the same as you.' Peter?' I said, barely stifling my astonishment. Peter was a man's man, into rugby and pubs with the lads. I couldn't believe it. Yeah. It was a problem when I found out, but I've got used to it and it's a part of both our lives now.' So why are you so upset about finding out about me?' I'm not -- just surprised, maybe. It was kind of tough dealing with Peter, but now I've got to do it all again with my best friend. What is this, an epidemic!?' I felt it again, that link between us. Anyway,' she said, I've seen you now, so that's that. And I can tell you, you need work. So let's get to it.'
Fran sent me upstairs and told me to dress in some of my favourite clothes. She came up thirty minutes later to find me in a slinky, stretchy blue mini dress with long sleeves. I had on my seamless bra, shiny black panties and nude pantyhose, and I wore black suede court shoes with a three inch heel. She studied me for a minute then said, Not bad -- more convincing than Peter was when I first saw him, but not perfect.' So?' `So -- get ready. We're going out. Err...but you'd better change!' I ran into my bedroom and peeled off the dress. My cock was straining under the panties and I just had to grab it. I ran into my en suite bathroom and tossed off for about a minute, cumming hard into the bath. I showered the cum away, got dressed in my male clothes and rejoined Fran in the living room.
We spent the next four hours shopping for skirts, dresses, tops and underwear, her holding items up to her -- she was 5 feet 9, the same as me -- for me to nod at as though we were shopping for her. By the time we got back, the front of my underpants was soaked with pre-cum and I had to go into the toilet again and lose the load before I could go on. Most weekends, I would feel pretty spent after four orgasms in a day, but I was ready for more and it was only two o'clock.
I sat on the edge of the bed, stripped naked and stroked my silky-smooth legs. Already my dick was twitching back to life. I cracked open a brand new packet of nude pantyhose with the panties built in, then slipped on a deliciously tight body shaper with integral bra which gave me lovely smooth lines and a neat waist. I slipped the silicon breasts in place, using the adhesive I'd bought a while ago, then rummaged through the bagfuls of clothes we'd bought, pulling out a black stretch pencil skirt and long sleeved, tight fitting cashmere top. Putting this ensemble on was getting me hot, and when I slipped on the round-toed ankle strap shoes with clumpy four inch heels and twirled in the mirror, I almost came again. Taking a few deep breaths to calm myself, I sat down to apply a little make-up, then pulled my hair back behind my ears, before clipping on a couple of delicate pearl earrings.
I was nervous as hell when I stepped into the living room where Fran was waiting. I looked at her, hoping for approval. She stood up and walked round me like an exhibit, then sat down again. Nice,' she said, very nice.'
She beckoned me to her and patted the sofa beside her. I sat next to her, breathing hard with a mixture of excitement and nerves. She edged down onto the floor in front of me and prised my knees apart, then burrowed her head under my skirt. She slipped her right hand in and undid the poppers of my bodyshaper before tugging my pantyhose down so that my engorged cock sprang free. I could see the head of it prodding urgently at the material of my skirt. Then Fran wrapped her fingers round it and began stroking up and down. Something softer, warm and wet, then started tickling at the shaft -- her tongue! I threw my head back in ecstasy as she wrapped her lips around the end of my cock and started pumping up and down. I looked down to see the outline of her head bobbing under my skirt and the sight was too much. I came in jets into her mouth, a deep and lasting orgasm which, Fran told me later, was stronger than anything she'd ever experienced before.
I was shattered and Fran nestled into my body after hitching my pantyhose up again and smoothing down my skirt. We stayed like that for a while, but I couldn't help looking down at my breasts pushing out against the sweater, my smooth legs shimmering in the light, my feet encased in feminine shoes. And soon I was hard again. Fran started to rub my cock through the material of my skirt and made to get back on her knees to suck me off again. Instead, I pulled her around to face me, then gently pushed her onto her back. I reached under her flimsy flared skirt to remove her panties and pulled my skirt up around my waist. I dragged my rock hard cock out from the pantyhose which I propped against my scrotum, then knelt either side of Fran whose cunt was now dripping wet. I slid inside her and felt my pantyhosed legs rub against the smooth skin of hers, pumping harder and harder until she arched up and screamed out. A couple of seconds later, I spurted a huge load inside her.
That weekend, I stayed feminine and we made love several times, but Monday was looming and neither of us wanted it to end. At midnight on Sunday, we were lying in bed and Fran said. Peter's staying with me next weekend.' My heart sank -- I had a whole week ahead and next weekend would be me on my own again. Yes, it was good on my own, but now I'd been with Fran, it would never be the same again. She sensed my disappointment and straddled me, smiling. Don't worry,' she said, `I've got a great idea. Just prepare to be more girly than you've ever been before next weekend but, whatever you do, save your spunk this week -- you're gonna need plenty of it!'
With that, she edged down to my cock, sucked it to rampant life and brought me to an explosive orgasm. Cum dripping from her lips, she smiled and said, `Ok, that's your last load till Friday.'
- Discovering A New Way
It was tough week. I knew the weekend was going to be hot and tried not to think about it but had to relieve my almost constant erection on the Tuesday evening. When I went to pick up the post on Friday morning, there was a note from Fran which simply told me to be at her flat at 8 that night, dressed for a proper girls' night out. I could hardly stand it at work and told my boss that I had a migraine at three o'clock and had to go home. I was a hard worker who was highly regarded, so he didn't object. I made my way towards Oxford Street station but instead of going down to catch a train, I spent the next two hours trawling the ladies shops for some new outfits.
I got home at six, waxed everywhere, showered, shaved and made myself up. I tied my hair back into schoolgirl bunches which made me look incredibly cute. I stuck the silicon breasts to my chest and put on a skimpy seamless bra, nestling the breasts comfortably inside the cups. Running my hands over them made me impossibly hard, but rather than playing with myself, I slipped a thick condom over my cock and pulled on the tight shaper panties I'd just bought which flattened it to my tummy and helped shape my waist. I rolled on the most gorgeous pair of 7 denier pantyhose which evened out the natural colour of my legs without looking as though I was wearing anything. The top was blue and made of stretch lace. It was long sleeved and scoop-necked and clung magnificently to my boobs. I the pulled on my skirt, a white stretch number somewhere between a mini and a micro. My legs looked long, slender and sexy once I'd slipped into my strappy new black shoes. Wow! I breathed hard, trying to gain control of my cock which was begging for relief. I clipped on my pearl drop earrings, put a delicate gold necklace around my neck and about ten coloured bracelets on each wrist. I wrapped a white cashmere cardigan around my shoulders and checked the clock.
It was 8 and I was ready.
I tottered down the stairs, not quite used to the new shoes, and tapped nervously on Fran's door. When she opened it, two beautiful girls stood before me dressed in mini skirts and gorgeous Lycra tops. Fran smiled at me and said, `You know Peter, don't you.'
Christ! Peter was gorgeous and I almost creamed my panties there and then. Hi,' I said, unsure whether to shake his hand. Hi,' he said in a meek voice. This was Peter, the man's man? `He gets a bit girly and shy when he's dressed like this. And he prefers to be called Petra. Have you got a name?' My real name was Alan, but when dressed, I always thought of myself as Alma.
Alma,' I said. Girls,' said Fran, looping her arms through Petra's and mine, `let's go.'
Petra and Fran sat in the front of her nippy little Mazda, with me in the back. It was tight back there and my legs were squashed together at an angle to the front seats. The friction of the pantyhose material between my inner thighs was almost too much to bear, but I made myself think of bad smells and road accidents to distract myself! After a few minutes, Fran pulled up in front of a large house and turned to me. Shift up,' she said. One more to come.'
A minute later, she was walking beside a stocky man towards the car. She pushed the front seat forward and he got in beside me. Hi,' he said, I'm Bill.' `Alma,' I said in my best feminine voice.
There was a bit of tension in the car after that, borne of unfamiliarity and, in my case, trepidation. What was going on? Fran drove into the West End and found a meter near Regent Street. Stepping out into the packed street was my next problem. I'd never been out dressed before and this -- apart from the short walk from Fran's flat to her car on the way out -- was my first venture. Bill looked at me and, seeing the fear in my face said sweetly, Don't worry, nobody would ever know.' Shit, you and Petra look better than me,' said Fran reassuringly. Bill stepped out of the car and held his hand out. I took it and got out, trying to remain as ladylike as possible. Standing on the pavement, I pulled my skirt down and smoothed my clothes. Wow,' said Bill standing back to check me over. Magnificent.'
We walked for about five minutes, Fran leading the way. I'd never felt the rush of fresh air between my legs before, nor really experienced the bounce of my boobs over a distance. We went to a hip bar called `Lightening' in Derby Street. There were a few TVs in there, but I would guess that most of the guys and girls were straight. We drank enough to get merry and maybe lose a few inhibitions, but all of us seemed tacitly aware of the need to keep ourselves reasonably sober to avoid brewers wilt! Fran and Petra danced and spent some time in the corner petting, but Bill and I just talked. I'd never found men attractive, but I felt myself gradually slipping into the persona of a woman, my movements and responses utterly feminine, my flirting that of a girl, not a boy. Still, I was only playing the part, getting the best out of the evening, never thinking for a minute that I would go beyond my normal boundaries.
At about eleven, Fran came over and nodded at Bill and I to get up. Outside, the air tasted fresh and clean, and Bill took my arm to escort me back to the car. We were back outside Bill's flat inside twenty minutes. He slapped his palms into his thighs and, almost shyly said, `So -- anyone for a nightcap?'
Automatically, I started to shake my head, but Fran and Petra said `yes' in unison and before I knew it we were inside Bill's flat. What the hell, I thought, it's just a nightcap. His flat was large and stylish, and I spotted at least two bedrooms as we walked down a corridor towards the living room. I was busting for a pee and Bill showed me where the toilet was. Inside, I peeled my panties and pantyhose down, hitched up my skirt and, without thinking, sat on the toilet. My cock sprang up, the condom still in place and full of the pre-cum which had been leaking out all night.
I needed to soften up to pee, but despite my attempts to distract myself, I couldn't make it flaccid. No option. Working the condom up and down my shaft, I came hard within two minutes and after another couple of minutes, was able to relieve myself. I started to pull my panties up again, but was concerned that it might be another hour before I got home and, not wanting to stain my lovely new clothes if my cock got randy again, I decided to roll on a clean condom. I had stuffed four or five into my dinky little bag on the way out and was glad I had. Freshened up and sexually calm again, I stepped back into the living room. Fran was on the sofa with Bill and they were kissing. Petra looked meek and mild as she sat on an armchair, but not too bothered. Fran broke off her kissing and looked at me. `So? Ready to try somethng?'
`Err...no...what do you mean?'
She got up and told Petra to sit on a chaise longe near the window. Without another word, she nodded at Petra who shifted her hips slightly off the chaise longe and eased her stretch lace panties and diaphanous pantyhose down her thighs. Her cock jutted out and up from underneath her skirt, six inches long (I'd imagined more) and quite slender. The head was almost purple and I realised that Petra had been in the same excited state as me all night. I'd just come like a train, but already my own cock was jerking back to life. Fran put her arms around my shoulders and gently forced me to my knees. Petra's eager cock stood staring at me. `I think you know what to do,' she said.
And I did. Never before had I even contemplated touching a man, and now I was about to envelop a raging cock in my mouth. I leaned over, lips parted, and nibbled at the head. Petra wiggled and thrust upwards, wanting more. I nibbled again, then lowered myself down, feeling the head pushing into my cheek and the shaft rolling against my lips. I started to bob up and down and was only vaguely aware of Bill being ushered over by Fran to take up a position on the floor between me and the edge of the chaise longe. He fumbled under my skirt and tugged my panties and pantyhose down sufficiently to allow my cock to spring free. He chuckled, perhaps surprised to see the condom stretched long and tight over my straining cock. I carried on sucking hard on Petra's cock, feeling it swell some more in my mouth. Bill clambered up and wedged himself between me and Petra, forcing her cock out of my mouth with a resounding plop. I was a little irritated, but also curious as he staddled Petra who was groaning desperately for release. Fran motioned for me to go behind Bill who I now realised had no trousers or pants on, and grabbed my cock. Glad to see you're ready,' she said, teasingly masturbating me with the condom. Now let's see you use it.'
She guided me towards Bill's ass and I noticed that it was glistening -- he'd pre-lubed! I slid my cock inside him and whimpered. It was as good as any cunt I'd ever entered. Bill was now sucking Petra while Fran somehow wedged her head between Petra's knees and Bill's chest to slide Bill's cock into her mouth as she played with her cunt underneath her panties.
I was now sliding in and out of Bill with abandon, desperate for my first come inside a man. As I pushed him back and forward, his cock moved naturally in Fran's mouth while his own mouth slid up and down Petra's cock.
Petra started to squeal like a girl, thrusting her cock hard down Bill's throat. I started to squeal, then Fran, then Bill. In one shuddering, shattering moment, we all came together in this weird and wonderful four-person melange. My cum seemed to spray out forever, while Petra screamed like her orgasm would never end.
Finally, it was over and I slipped my deflating cock out of Bill's ass. He fell back onto his haunches, cum dripping from his mouth, while Fran and Petra collapsed where they were.
I went to the toilet and eased the overfull condom off my cock, chucking it down the pan and flushing. I sat down and peed, my heart still pounding in aftershock. A moment later, Fran knocked on the door. I told her to come in. So?' she said. Wasn't that bad, was it?'
It was great,' I said. I never believed I could...'
Shh' she said, and started to rummage in my bag which was on my lap. She pulled out another condom, ripped the packet open and looked up at me, smiling. I told you to conserve your spunk, so you should have plenty left.'
She slipped her lips over my cock and brought it to life, before rolling the condom on. `Why can't you finish me off?' I asked.
`Because, this weekend, I'm straight -- I'll only take Bill's spunk. You're bi, and you'll be playing with Bill and Petra.'
Back in the living room, Bill was gently sucking Petra's cock alive, his own already up and ready. Fran pushed me towards Bill and motioned for me to suck his cock. As my warm moist lips encircled it, Bill let out a low whimper and immediately disengaged his mouth from Petra's cock. Petra whimpered, but Fran smiled at her, a lubricated condom between her thumb and forefinger. Petra grinned and leaned back to allow Petra to roll the condom onto her cock. Fran then manoeuvred me round, forcing Bill's cock momentarily out of my mouth. She then squeezed a large dollop of KY Jelly out of a tube and smeared it liberally on my ass, gently easing the gooey gel into my hole making me stiffen slightly. `Relax,' she said soothingly, working the KY in and gently widening my hole with two, then three fingers. She told Bill to sit on one of the dining chairs. His cock was rigid and around seven inches long, but not too fat. Fran led me over to him and had me pull my panties and pantyhose down to halfway down my thighs. Then, with Bill's help, she manoeuvred me over his knees and grabbed his cock to guide it inside me. It hurt for a second as it pushed at my hole, but I was well lubed and stretched and, suddenly, it was buried deep inside. I looked into Bill's eyes and started to kiss him. But Fran wanted things to move on and started lifting me at the waist to get some friction going. I began moving up and down and felt Bill's condomed penis grow inside me. My own cock stood upright between us, jigging and dancing in the air as I worked Bill's cock. I felt my boobs bounce inside the bra and stretch top, making my stomach flutter with joy. I looked back at Bill and saw his eyes start to bulge. His cock was huge now and ready to blow. Fran guided Bill's hand onto my cock and he began pumping it like a piston inside the lubricated condom. He was gasping for air, his face red and his lips engorged with blood. And then he exploded. Even inside the condom, I could feel the gobs of cum jetting out against my innards. The feeling was too much to bear and I simply came in buckets in Bill's hand.
After a couple of minutes, I turned to look at Petra who had been enjoying every second. She smiled and said, `My turn.'
I shuffled over to her and eased myself onto her cock. She groaned with pleasure, then started moving inside me. I pumped up and down and felt my own cock miraculously spring to life again. Petra closed her eyes and almost lost consciousness as she spurted her cum into her condom planted in my ass. I looked down and saw that Bill was pulling my cum-filled condom off and was licking the rest off my cock. Soon, he engulfed my cock in his mouth and worked up and down with increasing speed until I shot endless jets into his mouth, while still mounted on Petra's cock. I could feel her cock growing again in my ass and I was soon pumping her again till she came in ecstasy a few minutes later.
And so the night progressed. Just when it seemed that one of us was spent, someone else needed relieving, which turned the reliever on so that he/she needed doing again. This circle resulted in me cumming at least eight times. I'm sure Petra and Bill matched that. I took at least five loads up my ass, the rest in my mouth, and, incredibly when we were ready to leave after a well earned breakfast on Saturday, I was ready for more.
Back at Fran's flat, Petra fucked me up the ass twice and I gave her a load in each orifice. Afterwards, I went upstairs to my flat to shower the cum off. Although all ass-fucking had been protected, our mouths were taking the cum down neat and eventually it got everywhere. I put my clothes in the washing machine, then took a nap on the bed. I was woken at seven by a knock at the door. It was Petra with another stunning girl, both dressed up prettily for a night out. They asked me if I'd like to join them, but in all honesty, I needed a rest. The other girl, it turned out, was a guy called Ed who, when dressed in high heels preferred to be called Eleanor. Petra had told Eleanor how good I was and wondered if I wouldn't mind showing her my prowess.
Oh well, in for a penny. I had to get dressed, of course. I could still only do this as a girl. So I slipped on a clingy bra top over my breasts which were still in place, thigh high stockings for easy access which came right to my crotch, filmy white panties and four inch court shoes. A little makeup and, voila, I was ready. Eleanor was very hot looking -- tall and slender with sultry looks. She wore a short denim skirt and a floaty blouse. Her legs were clad in black thigh highs, her feet in skyscraper heels. She pushed me onto my bed and burrowed underneath my skirt, taking my rigid cock in her mouth just to get me ready. Then she reversed and, after I'd rolled a condom on, eased her ass onto my cock and gave me the fucking to end all fuckings. I squirted a quart of cum into the condom -- where was it all coming from? -- then pushed her onto her back to suck her off. She came ferociously in my mouth. For good measure, Petra slyly slipped her cock up my ass and came like a train within a minute. Eleanor recovered quickly and wanted to give my ass a try. I was obviously ready! As she worked in and out of my ass, Petra sucked me off as she masturbated. We came together in a wild heap.
As Eleanor smoothed herself down and made to leave, she turned to me and said,' Petra was right. You are good. How about coming out with us next week?'
I smiled, a drop of cum trickling down my chin and said, `Sounds great. See you at seven