A night on the town (M/M/F, oral, anal, inc, TV)
by einhard
PLEASE NOTE: This story is fiction from beginning to end. The characters don't exist, and the stuff they do, never happened.
Part I: Getting ready.
"Goodbye, Philip! Have a good time!"
There I stood at the front door, waving at my parents. They were going on holiday for a week, leaving me home alone the whole time. Yess! Not that I hadn't been home alone before; I was, after all, 18 years old. But I had plans for the coming week. If things worked out, I'd be having fun the coming week. A new kind of fun.
Closing the door on the grey October afternoon, I walked back inside. It was probably best to wait 20 minutes or so, just in case they forgot something and had to come back. I really didn't want them to catch me, so patience was in order. I'd been patient for months, so a few more minutes wouldn't be too hard, surely?
It was, especially since they didn't return. Sod that, my life could start now. My new life. First, I'd get all my stuff ready for use, putting it out on my bed, then a shower and a shave, and finally putting it all on. I didn't know how much time I'd need, and if it turned out all right, I would want to go out on the town rather late, but before it got really late. It was still only 6:30 p.m., but for all I knew, this might take four hours. Or then again, maybe only one hour. Well, nothing would happen if I didn't begin.
Into the bedroom, and out with the boxes that had been hidden in the cupboards. Oh, yes! This stuff was so hot! And to think I'd never tried dressing up in it before. Not for real, anyway. I hoped I wouldn't botch the job and look ludicrous or something.
As soon as everything was ready, I undressed. My bedroom isn't very big, but it has one feature I love: The big mirror! It's not full length vertically, but it's wide.
I undressed slowly. Socks first, then shirt. This was nothing new, and I loved the sight of the narrow shoulders, the flat chest and the androgynous face. But for one thing, I looked almost like a girl. I've got this great body, you know. Practically no hair, except for a few blonde strands in each armpit, hardly visible. Plus the pubic thatch, but even that's small. And the small growth on my calves is negligible. You almost have to know it's there to be able to see it. All of it on a 5' 3" frame, weighing 110 lbs. Just the right size!
Next, the trousers came down. Those boxer shorts are so unsexy! Still, it's the only sort of underwear that's comfortable. If you could have watched me as the boxers slid down, you'd understand why. Between my thin, smooth legs there hangs a monster. It's almost eight inches limp, and really fat, too. Fully hard, it will grow to 9 1/4 inches. I hate it! Why can't it be a nice 5 inches, like Tony's? I love Tony's prick. It's just the right size for sucking on, which is my favourite hobby. Not particularly sucking on Tony, but a cock in general. At the time,his was the only one I'd had. None had been up my arse. I mean, I asked him several times, but he never wanted to. He just wanted me to fuck him all the time. That boy is such a size queen!
We hadn't been sex partners for very long. In fact, it only began about a month earlier. I had wanted it for years, lusting after dozens of boys. As it happened, Tony was the one I finally scored with, back in September. We'd been out together, celebrating his birthday, and quite frankly I was sozzled. So much so that I was scared to go home. That's why I stayed over at Tony's. It was probably the booze that did it. Squashing all inhibitions, I mean. Almost before I knew what was happening, there I was on my knees, swallowing Tony's penis whole. I'd seen it before, of course, but never hard, and I had no idea it was so beautiful. Not like the rest of him. Tony's not ugly, but definitely plain. Most of him, that is. And the taste of it! I think I knew I was hooked before my lips touched it, and when he orgasmed down my throat...It was heaven! To think I could do that, just using my lips and tongue. A natural born cock-sucker, that's me. Who cares about brains and muscle when you can suck cock?
Tony had been even wilder, especially when he got his hands on my absurdly massive thing. He wanted to sit on it straight away. He told me later that night that he'd been fucked lots of times, but never by anything that big. Well, you could have blown me over with a feather! Tony, a pussyboy! He certainly had had lots of practice. Before the night was over, I'd had my prick up him three times. It was all right, I suppose, but sucking was the best.
After that, we did it lots of times. Usually twice or three nights every week. Tony gave me rimjobs every once in a while, but so far, he had never stuck anything up my arse except his tongue and once or twice a finger, and I was sick of waiting. So this particular night, I planned on going out on the town to find a man who would shag my arse from here to the end of the solar system. But wait! There's more! There's more? Oh, yes, quite a bit more.
I shaved in the shower. It's easier and more efficient that way. It's always easy, because I don't have much in the way of facial hair. And on my legs, well, that went quickly, too.
After drying myself off, I returned to the bedroom and sat down in front of the mirror. What a sight! A young, unblemished face staring back at me, long, wonderful hair streaming down the shoulders and back. And no sign of the absurdly big penis. I'm pleased with the way I look, but perhaps you've figured that out already.
Now for the first treasure: The make-up box. It hadn't been all that easy to compile the stuff I would need. I wasn't brought up with cosmetics, you know. I'm a boy, remember? And when you're not quite sure what everything is called, what it's for, or how to apply it, then how do you go about buying it? There was no way I was going into a shop to start trying things out. I'd die of embarrassment. Fortunately, I was old enough to buy things on mail order and online. So that's what I did: Searching for make-up and fashion tips on the web, and then buying the stuff I thought I'd need. And here I was, ready to begin. But how to begin? Where was this guide I'd composed for myself? Ah, yes, in the drawer.
Now, I'd need foundation, mascara, eye liner, eye shadow, lipstick and blusher. The guide had said to "keep it natural and go for the earth tones". So that was what I would do. With practice, I might try something more outrageous later on, but right then, keeping it simple was the order of the day.
Okay, foundation on. I had watched my mum using stuff like, so I knew a little bit about putting it on. But how much? Would it be possible to figure out if a particular colour tone worked before everything was on? Best not to worry too much. If the result was bad, I could try again.
I set to work as systematically and as patiently as I could, humming softly to myself. Somehow, it seemed easier than I had thought. Or maybe I was doing it wrong. Whatever the reason, this was fun! The strange sight of my facial features slowly growing even more feminine, of a young woman coming into sight, brought my most masculine part to life. The horse-cock was half hard, standing almost straight out in the air. I didn't stand up to watch myself with make-up and erection in the mirror, though. That would have to wait.
Right! The make-up was on, and I would just have to take my chances. I really didn't know what it would look like in this kind of light or that kind. If people thought I looked ridiculous, then so be it. There would be other chances. And even if my body is small and frail (with one exception), my mind isn't. I tell you, I'm as thick-skinned as they come. This was one reason I was never very popular in school; I always had the nerve to speak up. So all thoughts of a diplomatic career were shelved at an early stage.
But right at the moment, I was getting dressed. I'd spent hours agonizing over what to buy. I wasn't really on a budget, because my grandparents had left me quite a bit of money, which I controlled for myself now. But even with 30 000 quid in the bank, it's not smart to be extravagant. And if I started buying in bulk, my parents would get suspicious. I really, really wanted a place of my own. The problem is, London is so fucking expensive!
I digress. Looking over the stuff laid out on my bed, I decided on a combination of a garterbelt and black, sheer stockings. Garterbelt on first, then stockings, then attach stockings to gartebelt. Easy! I looked myself over. Was it sexy, or just funny? You know, small, hairless upper body, thin legs dressed in those wonderful stockings, garterbelt round the waist. Except for the missing boobies and the narrow waist, very feminine and ultra-sexy. Seen from behind, the illusion was almost perfect. Or so I thought, anyway. From the front...I really had to laugh. It was hanging limp again. Now, most boys' penises tend to be pretty short when limp. Almost negligible. In fact, for many of them, the balls and the pubic hair dominate over the penis. Me, I don't have much pubic hair, as I said. I've got massive balls, though. But the only thing anyone else ever seems to notice, is the ridiculous dong. I've seen quite a few pair of popping eyes in the locker rooms before and after PE class. To tell the truth, I've noticed many stares when I'm fully dressed, as well. Boys, girls, teachers. I think even my Aunt Eve lusts after it. To lots of people who know me, but don't know me well, I'm not even Phil. Just "Horse-prick". They think I don't know that that's what they call me, but I do. You sometimes hear women complaining that they're judged simply by the size of their tits. I know how they feel.
And that looked like it might be the tricky bit. Breasts, I mean. I'd bought two pairs of artificial ones from the USA, at 300 dollars each per pair. On the web it was promised that attaching them would be easy. The silicone used would mould to your body shape.
Triangle or tear-drop form? Hmm. Tear-drop would look great if they were fairly big, but they weren't. Better go for the triangular ones. I had studied the instruction manual closely several times, and felt confident I could do it. I was still surprised at how easy it was. They even looked quite good. Felt good, too. Heavy. Seen on my naked upper body in the good light I had in my room, they were clearly fakes, but good ones. Looking at myself in the mirror, my friend/enemy down between my legs was very much in evidence. The way he was striving to get higher and higher, it almost looked like he wanted so say hello to my new boobies. It takes a bit to get a cock this size to grow fully hard, but pretty soon it was throbbing. There was even a bit of glistening pre-cum visible. I scooped it up with my finger and smeared on the right tit. It would have been wild if I could feel it right on my skin, but of course I couldn't.
Oh, well, he'd get his fun later. Now to select something with which I could cover my exquisite, but artificial breasts. A cami or a bra? I had a small selection of both varieties. Actually, I had a pretty large selection of bras. They looked sexier than camis, so bra it would have to be. I was going out looking to be shagged, after all. Sexy was all-important.
I chose a black one, to match the stockings and garter-belt. I don't understand blokes who moan about the difficulties of getting the bra off a girl. I mean, putting it on is so easy, so how hard can it be to take it off?
Turning back to the mirror, I saw that the illusion was improving. Or maybe I was just getting more excited. My prick was getting painful, it was so hard. But even with that log pointing upwards out of my crotch, I mainly saw an incredibly sexy young girl staring out at me. I squirmed, and my left hand started caressing the straining erection.
"Oh, yes!" I whispered to myself, trying to pitch my voice a bit higher than normal. "You like the way Phillida is looking tonight, don't you? You want to get inside her mouth, hmm?"
I'm proud of my flexibility. When I was smaller, I had been a gymnast, but as puberty set in, it became evident that I had no future in that sport. The kind of gymnastics men do, requires a lot of muscular strength, much more than my slender frame could support. So, I switched to ballet, which I'd kept up until the summer, only months away. Me, twenty-two girls, and one small boy. I missed it, but I still exercised and stretched a lot by myself. And I had found out recently that I could give myself a blow-job. I probably could have done it years ago but the thought never struck me. How slow can you get?
So I lay down on the bed, pulled my legs up over my head and took in the head of my nine-incher. I wasn't able to swallow all of it, but that wasn't for lack of flexibility, it was because of the size. As two fingers on my right hand slid in and out of my sweet little bottom, I used the left to alternately stroke the perineum, pull and squeeze viciously on my balls or make masturbating movements round the base of the shaft.
It took less than a minute before the muscle spasms were a fact, and I was greedily swallowing the liquid shooting out of the slit. I can tell you, staying in position with your legs behind your head, so to speak, is not easy when an orgasm is raging through you. However, it was important not to spill any sperm over my underwear. Preferably not on the skin, either. It smells, you know. If I went out on the town smelling of cum, people might take me for a tart. Or even worse, they might suspect I was really a boy.
I eased myself to a prone position, then stood up. There were traces of sperm on my painted lips and traces of lipstick on the crown of the cock-head. Wild! I wiped it all off and watched for a bit as horse-boy down between my legs subsided.
"There! That might keep you quiet for a bit", I told him.
Now for the waist. I had a few panties, but have you ever tried to contain a mega-prick inside one of those small pieces of cloth girls wear down there? No? It's impossible, that's what it is. And in any case, I would have to wear something over it to give me a waist, so there wouldn't be much point. Now, this was an unsexy bit of clothing, but it had to be done. As a rule of thumb, a woman's waist needs to be about the same width as her shoulders. For men, the shoulders are generally quite a bit wider than the waist. My shoulders are narrow, of course, but so is my waist. Which meant I definitely needed help to achieve the full illusion of femininity, and that in turn meant large, padded undergarments. As I said, they were not sexy, but I trusted them to do the job for as long as I stayed dressed. I mean, after the outer layer of clothing was off, and I was getting ready for a prick up my hole, I couldn't really wear much down there, could I?
The web-site I'd visited, had two varieties: One for wearing with jeans, short skirts and the like, and one for long dresses and so on. So what would I wear? I had a lovely, lovely, long blue dress of something silky. I was dying to try it, but it might just be a little over-bold to try that the first time. After a short internal debate, I decided on jeans. They would be appropriate in most places, and were really the best all-purpose choice. That settled the question of which hip-padding garment to put on. Still, I quickly covered it with the jeans.
The shape was excellent. Protruding under-belly, wide hips, big bum. Nice! The only problem was... can you guess it? Yes. My prick. Whichever way I tried, it was either uncomfortable, in danger of becoming visible, or both. Drat! I finally draped it under my nuts, pointing backwards.
Now, this was illusion! A girl's small, dainty feet, clad in stockings, a girl's legs, hips and bum, covered by jeans, a girl's smooth, slender belly, wonderful smallish breasts hidden behind that incredible bra. I shuddered at the beauty of the apparition that tonight was Phillida. Not a common name, I know, but it's pretty, and can be shortened to Philly, which is very like Phil. Not so easy to forget when people are talking to you. It would be embarrasing to just stand there and who people meant when they said my name.
Going upwards, I considered my face. The small chin and the somewhat high, protruding cheekbones were just right for a girl. The make-up still looked good, though it would probably be wise to put on more lipstick after the little auto-fellatio session earlier. Hm. Something was not quite right. The eyebrows? Or the hair? No, the eyebrows. They were thin, which was all right, but not really feminine. Of course! They were much too straight. They should be curved. I tried to think about the women and girls I knew. Did they really have eyebrows that were more curved than mine? Or was it just part of the conventional beliefs of what women should look like? Whatever the answer, I quickly decided to leave the eyebrows as they were. It would be too risky to start anything funny at this stage. If I started plucking them, things might go wrong.
Finally, the hair. Now, my hair is really something. Shoulder length, blond, straight, luscious. That's the word, luscious. In all the meanings the dictionary gives. I love it. I could be a real narcissist if I don't watch it. Perhaps I already am.
A quick glance at the time. Bloody hell, it was past nine. Over two and a half hours had gone by. Time flies when you're having fun.
Another layer of lip-stick, and then for the blouse. I had decided early on to wear a white one. White blouses are like jeans; they're good for lots of different places and atmospheres. Best to make it simple this time. A bit awkward with this buttoning, though. Girls' garments button the wrong way, but a smart bloke like me would figure that out. A smart girl, I mean.
A small golden bracelet on the left wrist, and then the earrings. I'd asked my parents to have both ears pierced at fifteen. They refused, so I had it done anyway. I was grounded for two weeks after that, but the deed was done. These little bijous I was attaching were not my regular ones, though. They weren't ordered through the mail, either. I'd stiffened the sinews, summoned up the blood and gone to a good jeweller's to aquire a small stock. Not glaring, but stylish. And with a price tag to match.
Now I was pretty much finished, and what a sight I was. Woo-hoo!
"There is nothing like a dame, nothing in the woooorld.
Nothing else is built the saaame, as the silhouette of a daaame."
If I tell you I sing well, you'll probably think my self-love is going way over the top, but it's true. I'm not cut out for the big opera stages, but my voice is quite presentable.
I still had about an hour to spare. 10:30 was the time I had decided to hit the town, and it was 9:15. A wee drinkie to steady the butterflies. I didn't have carte blanche to raid the drinks cupboard, but mum and dad won't mind if I took the occasional snifter. They had said so.
With a gin and bitter lemon in my hand, I traipsed about the house for a while, trying to walk, talk and feel like a girl. Did a good job of it, too. It was cool to leave lip-stick marks on my drink glass. Somehow, that seemed to count as a confirmation that I was no longer Philip, but Phillida.
I also tried out shoes. I only had three pairs, and one of those were high stilettoes. No way was I taking them out so soon. The other two were of the low pumps variety. I went for the black ones. Red seemed slightly outrageous.I worried just a bit about colours. Maybe I was being less bold than I should? Ah, to hell with it! Boldness could come later.
For a jacket, I did the simplest thing possible, and took my own blue denim (Philip's, I mean).
So, at 9:45 I was all dressed up and with no place to go. At least not quite yet. I had planned to walk to the tube station and catch a train into the city. Then a pub, possibly two. Depending on what happened there, I had singled out some dance places for later on. The problem with all this was that they were gay places, and I went there dressed as a woman to land a man. And what's more, I didn't go as an obvious drag queen (or I hoped not), but with the express purpose of appearing as a woman. So, what were my chances of finding a bloke who would want to shag me? I didn't know, but I did know that I had no desire to be just an ordinary bloke obviously dressing up as a girl. Nor did I want to go to the hangouts of transvestites and transsexuals, even if I did see myself as a transvestite. I very much like being a biological male, even if all the maleness is perhaps a bit too concentrated in one particular place. You know which place I mean.
It helped that I had planned and thought things over. I was still nervous, but not half as much as I had expected. I mean, I looked good and I knew it. And whatever happened, I expected to return home with a sense of achievement. Plus a good wanking memory or two. At the very least
After one more drink, I started to get this pleasant buzz alcohol can give. My limit was almost reached, and I'd have to be careful later on.
Right after the second drink was finished, I discovered a problem: I needed to pee. And I couldn't exactly whip out my cock the way I usually do, could I? This bloody thing that gave me a waist wasn't the easiest thing to get off and back on. But if I was going to pee, it couldn't stay on.
It went well. I practised pulling it off and back on again a few times, until I could do it with a minimum of funny noises. The sound of me pissing wasn't quite like the sound of a real girl, though. Not the angry, spitting sound of urine coming out of a short pipe located high up. If I only peed in a noisy toilet, nobody would notice, and if nobody was making any noise, I'd have to make my own noise.
The moment of truth was approaching. The clock said 10:28 and time to move. Putting on the jacket, loading the purse with all necessaries and grabbing my mum's umbrella, I exited the front door. This was going to be risky; walking through my own neighbourhood and taking the tube from my local station. There were people around here who might recognise me. And even if they didn't, they might wonder who this young lady leaving the Petersons' house was. If anybody mentioned it to my parents, it might get awkward. The obvious answer, of course, would be that I'd had a girl in here. I hoped it wouldn't come to that, though, because it would be a lie. And it would make it even worse when I came out to mum and dad. Perhaps you've figured out that I was still a closet case at the time. I fully intended to come out to them, but only after I had moved out of their house. I didn't really think they would give me a hard time about being gay, but you never know. That's why I didn't want to live with them when the time came. And I certainly didn't plan to tell them about my new dressing habits anytime soon.
All went well. Nobody looked at me twice. Nobody I knew, anyway, but at least one fat, middle aged man turned round to admire me. I prefer to think that's what he did.
At 10:57 that Friday night, Phillida Peterson left the train, walked up the stairs from the platform and stepped out into the streets of London, looking for adventure.
This story is copyrighted by me, einhard. Copyright March 2001.
Any comments? You can mail me at: einhard@excite.com