Date: Fri, 23 Mar 2001 04:30:29 -0800 (PST)
From: einhard <einhard@excite.com>
Subject: A night on the town, pt. 1

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