Note: This story was dynamically reformatted for online reading convenience.
 
 A Teenage Tranny's First Time: by (c) Hamilton Joyce

   Jolyon stetched his legs out and enjoyed, as ever, the feel of the
glossy nylon as his thighs rubbed together.  In the ceiling mirror overhead
he was able to admire his own satin-clad slim form and that of the muscular
guy sitting propped like him against the bedhead.  This was a good way to
earn a living!

   After the first sixty nine, the guy....Jolyon knew him as "John" and
that he was a banker in the city like so many of his clients....while
Jolyon sucked his cock and licked his balls to get him up again the guy had
amused them both by telling the story of his first sex, seduced by an older
brother.  He had then pulled his partner's knickers aside and fucked him.

   Now they were each enjoying a cigarette in silence, and it was Jolyon
aka Samantha's turn to tell a story to arouse the limp-cocked John and fill
the third hour the banker had paid for so handsomely.

   The guy seemed to be into little boy sex.  Well Jolyon's first sex had
been as a teen.  He launched into his tale.

   ...............................................

   He had been a pretty boy as a teenager with girlish good looks that he
kept into adult-hood.  He must have been eleven at his first sexual
encounter: certainly he had entered puberty and was jerking off night and
day, his little cock misbehaving by becoming almost continually hard.  It
was his first term in the well-known private secondary school in Central
London.  His parents had considered sending him to boarding schoo;, but his
mother had won her way and it was this day-school.
It meant, however, a thirty minute journey twice a day on the

underground.

   The day it all happened for him there was a bus strike, which meant the
tube was very crowded.  The first train that came was impossible to enter.
The second was just as crowded, but the boy managed to wriggle and push his
way in and even managed to find a place where he could lean against a
partition, facing it.  At the next stop one woman managed to fight her way
off, and just one man from the throng on the platform managed to get into
the carriage.  He was big built and strong and made his way past two people
until he was right behind young Jolyon.  Jolyon was glad he was clean and
smart looking in a charcoal grey suit and not some scruffy smelly erk
because the man was crushed right up against him.

   The train started and almost immediately Jolyon could feel something
sticking into his back...the guy had something in his pocket and it was
uncomfortable for the boy.  He tried to move a bit, but the pressure was
still there, and the man seemed to be jigging up and down ever-so slightly
so it rubbed against the boy, felt even through his school blazer and
shirt.

   With a sudden realisation the boy guessed this was not the man's pocket
but his crotch, not a book, a key or something but a hard cock.  His own
cock had gone hard as it often did with the vibration of the train so he
was not surprised.

   It was at least interesting....different at any rate!  A bit alarming?

   He turned his head and looked up at the man, who gave him a lovely,
happy smile.  Jolyon smiled back and turned to face the advert-covered
partition again.

   But now, as well as the pressure of cock against the small of his back,
he could feel a hand round in front of him grasping his cock through the
thin summer-weight school uniform shorts.  This groping went on through
several stations and at last the boy turned again and smiled up at the man,
rewarded by another smile and a firmer grip on his cocklet.

   The train half emptied at Tower Bridge but there were still no seats,
and the groping had to stop as not hidden by many bodies.

   Jolyon's stop arrived and he managed a shy nod to the man as he left the
carriage.

   The man got off too and followed the boy through the station and out
into the High Road.

   'Did you like what I was doing?'

   Jolyon stopped and turned round.  The man had wavy blonde hair, greying
a bit at the sides, and his happy face looked as if it had been scrubbed
for hours.  His suit was well-cut....  had to be with those broad shoulders
and narrow hips, and his shoes were very polished.  All in all a hundred
percent decent-looking gent.

   The guy looked down at the boy, a wet dream in his school uniform of
black blazer, grey shorts, grey socks and black shoes.  His shirt was crisp
white and his tie carefully knotted in what they then called a "Windsor
knot" His hair was too long for the silly, old-fashioned school cap all the
boys had to wear, and it stuck out round the sides, almost inviting being
stroked.  But not here!  A delicious little blonde-haired boy, slender,
about 11 or 12 the man guessed.

   'It was OK.' The boy blushed delightfully and looked down at his shoes.
So innocent!  He looked up again and there was that shy smile.  The boy had
passed through puberty and his voice had part-broken, but his balls would
still be hairless.  The man almost shuddered with the pleasure of that
thought.

   His cock twitched in anticipation of pleasures to come....  and memories
of boy-pleasure past.

   'I'm Marcus.'

   'My names's Jolyon.'

   'That's a nice name.  That was OK for me too, and I'd like some more. 
How about you, Jolyon?'

   Again that little-boy smile, hardly daring to say yes.  But the man was
so nice, and it had felt good.  He could see the man had a hard cock too,
but that seemed very normal to a boy who at the onset of puberty so often
had an erection.

   'There's a quiet place just off the High Street.  Only a step.  Come
with me, Jolyon'

   The front of St Tibb's Church was gentrified and tidy, green sward with
the gravestones neatly displayed against the church wall, except for a few
larger vaults.  But behind the church it was all overgrown with brambles,
the gravestones still in place but at all sorts of angles.  Through the
undergrowth there was a small well-worn path that stopped behind a large
granite monument.  It was a very secret place, but some readers would
recognise an absolutely typical urban cruising ground!

   There was, however, no-one around, and Marcus again handled the boy's
cock though his shorts before unzipping them and reaching inside.  The boy
wore loose underpants and Marcus could see they were white as he fiddled
around inside and at last managed to pull the cocklet out through his
flies. It was a little-boy cock, of course, slender and so white as to be
nearly translucent.  No hair, not even a fuzz.  The pink cock head peeked
out from his foreskin, seemingly shy like its owner.  Marcus rubbed the
cock up and down a few times and then skinned the knob.

   Lovely!

   They were both silent, the boy's heart beating so loud that he thought
it must be heard and not only by this man, so loud perhaps even to the
street.

   But now the man crouched down and had his arms around the boy's bottom
to support himself, and beyond all expectation Jolyon felt the warmth and
wetness as his cock entered the man's mouth.  Nothing had prepared him for
this pleasure, though he had sometimes imagined being hugged and caressed
by a strong man in his night and morning masturbation.  And almost
immediately he was cumming: it was still a dry cum at his age.

   Marcus felt the tension in the boy and then the release as the boy came,
but was not surprised there was no boy-juice for him, or perhaps just the
slightest taste.  That would come later!  probably only a few months
away.....

   'Was that OK?'

   'It was....' the boy searched for an adequate word....'fantastic!'

   'Good.  I loved it too, Jolyon.'

   'Can I....  May I.....' he was too shy to say what he wanted.

   'Can you what?'

   'Can I....  may I see yours please, Marcus?'

   'Of course!'

   The boy's cock was still erect and sticking nicely out from his school
trousers as Marcus unzipped and pulled his cock out for the boy.  You and I
would consider it a normal, average cock, but to the boy who had never seen
an erect adult cock it was a real surprise, big, veiny, rising from a
jungle of golden hairs, and with a large purple-red, angry looking knob. 
None of the boys in Jolyon's class had been circumcised, so even in the
showers he had never seen a cut cock.  It was fascinating and shyness
banished by excited, heart-beating curiosity and, yes, lust, he reached out
and touched it.  It felt hot.

   'Oh yes!  Rub it Jolyon like you do yours at night.'

   'How did you know?'

   'Well, we all do it!  Boys and men.  Everyone!'

   That was good to know, the boy thought, and applied himself to wanking
this huge male member.

   A dozen rubs at the most and a sudden stream of white liquid flew
through the air, another, and then it oozed over his hand.

   Now that was a surprise....  this must be the sperm, the "seed" Mr
Hargreaves had told them about in the Biology lesson in the first week of
term: so much, so fantasticly, masculinely much as it splattered on the
ground.  Jolyon looked at his hand.  There was a sticky patch on the side
of it and without a moment's hesitation he licked it.  It did not taste,
but felt silky.  Nice!

   'You're a good boy, and did that well.  Was it good?'

   'Oh yes.  Can we do it again, please?'

   'Not here, Best we leave before anyone comes.  You know this has to be a
secret between us?'

   'Oh yes!  But it would be nice....'

   'I live in Epping.  could you get over there at the weekend some time,
and we can play in secret....  and in comfort.'

   'Easy!  Saturday morning would be best.  What time?'

   'About ten.  Now let's zip up and get back to the High Street.  I've got
a card here with my address on it, and phone number if you change your
mind.

   'I won't and I'll walk to the station with you.'

   Father and son, hand in hot, sweaty hand, attracted no attention, nor
did the chaste farewell kiss on the boy's forehead.....'

   ..................................................

   'You've got me well-horny again, Samantha.  But first I've really got to
know what happened the Saturday.'

   'Lots, John.  And if you want to know why I'm "bottom" and tv....  well
it was that Saturday that started it all...

   'Tell me, angel...'

   'I suppose the phrase "stranger danger" had not been invented when you
were a lad and had your first experiments, John, but we certainly had it
drummed into us, including by coppers who visited the school and lectured
us from time to time.  so I nearly didn't go....

   'But I did go....

   'I remember sitting on the train as the stations went by and it got
closer, feeling very nervous, but excited as well: my cock was certainly
stiff: but then it usually was.'

   'It still is...'

   'That's because you're so sexy, John.  Yes!  I like it when you do that:
I've got a very sensitive arse-hole!  Where was I?  Oh yes on the train
feeling anxious, horny, scared, eager, a real little-boy mish-mash of
emotions.  I hoped I was not gay, but feared that I was: the culture at
school was dreadfully homophobic back then and the thought I was gay was
alarming and overlaid by guilt.  And then I knew so little about
Marcus....if that was even his real name....  He had a card with his name
on it, but anyone could get them made, and although he looked respectable
and a gent, he might be one of those monsters you read about in the Sunday
papers!  But I knew I wanted some more of what he gave me when we first
met, and that my cock was even harder than it often got on trains.  I
wanted to see him naked, feel his strong arms around me....

   'These little-boy thoughts filled my mind and there we were, Epping.

   'I pulled the Streetmap plan I had printed off the night before: it
looked like about a ten minute walk, and as it was five to I would be about
on time.

   'The house was quite old...  sort of Edwardian I should think, big on
three floors, with quite a garden round it, though the front had been
tarmacked over.  There were four stone steps up to the front door and I
hesitated a moment at the bottom.  This was my last chance to beat a
retreat: up the steps and ring the bell, and then no going back!  Almost on
auto-pilot, but heart beating, I stood there.  Would he be wearing a suit,
casual clothes...  or nothing at all?  My heart beat even faster, but I
rang.
'No suit, no casual gear, no naked, no Marcus!  Instead a boy about my

own age, blonde like me and smiling.

   "You must be Jolyon.  I'm Peter.  My Daddy said to let you in and tell
you he's had to take the car to the garage for servicing, but he'll be back
very soon."

   'I was dumbfounded!  In all my imaginings I had not seen Marcus as a
family man with a son.  In a way it was reassuring, but then there were
inplications to be thought through.  I could not think of anything to say
as, tongue-tied, I let him take off my coat and hang it up.'

   "Best for us to go upstairs and get ready for him."

   A mobile phone bleeped and he took it from his trouser-pocket.

   "That's Daddy.  Text.  He's got the car back and should be here in
quarter of an hour.  My room's up here."

   'I wished I had a room as big and well-equipped as this.....  laptop,
tv, speakers, plenty of books.  Well, we undressed and I was pleased to see
Peter had a smaller cock than me and that like me his was stiff already. 
He was quite fit-looking, and about as hairy as me....  just a little
triangle of pubic hair, blonde like mine.

   'What he did next really did astound me!  He rummaged in a drawer,
pulled out something nylon, and as I watched put on a pair of pink, satin,
women's knickers.  His cock made a tent in them, but they were tight across
his bottom.  The white lace round the edges made them look especially
girlie.  He rummaged again in the drawer and it was black nylon this time.'

   "These are for you.  They're new, and my best at the moment."

   'He threw them to me and I stretched them out by the waist elastic. 
Black satin, with black lace round the edges, and strangest of all a
transparent black nylon panel at the front.'

   "Dead sexy!"

   "I can't wear these...."

   "Why not?"

   "They're girls'."

   "I expect Daddy will like you naked, but I'm sure he'll really love you
in knickers.  I know him!"

   'I held them against myself and looked in the mirror: they did look
sexy. I put them on and the feeling of the satin across my bum and the
satin crotch cradling my balls was delightful, as it has been all my life.
My little cock looked good, too, through the front panel.'

   .......................................

   'You look good in lingerie, Samantha....'

   'And don't you guys enjoy it!  You take some viagra earlier?.....you're
nearly hard again.'

   ........................................

   'Anyway we kissed of course, open mouthed and long, interrupted only by
the beep of a horn'

   "Daddy!"

   'We scampered downstairs and got to the door just as it opened.  Peter
rushed at his father and flung his arms around his neck: they kissed, a
lovers' kiss not a chaste father-to son.  All my doubts evaporated: this
was not at all a usual family!'

   'As Peter hung his father's coat beside mine, smiling Marcus first held
my hand welcoming me and then hugged me as he had his son and we kissed.  I
could feel the cold winter air on his clothes against my near-naked body.'

   "Brrrrr!  It's cold out there.  let's go upstairs and get warm!"

   'We lay on the bed, Peter and myself: there was a large mirror set in
the ceiling.....  I should get one put here, John.....  and I remember
thinking how sexy we looked in our satin panties and realising why Peter's
father liked his little boys to wear them.  So my gaze kept shifting from
the pretty boy beside me, to the mirror reflection of both of us, and
returning always to Marcus as he undressed by the bed, carefully hanging
his clothes up as he went along.  I could see why he always looked so
smart: he looked after his clothes as well as his body.  And what a sexy
body it was!

   'In the churchyard I had seen the lovely golden hair around his cock but
now, as he took off his shirt I could see those blonde curls covering his
belly and then in a line up his chest, spreading into a mat almosy hiding
his nipples: there were one or two grey hairs among them and that just
added to his sexiness for this little boy....  like yours, John!  Then his
trousers, and he had what looked to me like huge muscular thighs... 
golden-haired, like a heavy weight boxer's, I remember thinking.  And, yes,
as a boy I used to clip colour photos of boxers out of magazines and
imagine myself caressing their bodies as I jerked off.  He had white, tight
boxer-style shorts, and I remember his bulge, realising he was hard..... 
like Peter and me in our knickers.  But he soon had his under-pants off
too, and stood by the bed magnificent and naked, stiff cock pointing at his
two boys.

   'He must have liked what he saw, two twelve year old boys, slender,
still summer-tanned, blue-eyed blonde, both making little tents in their
suggestively feminine panties.  I say he must have liked the view as not
only was his cock erect, it twitched by itself and I saw a drop of precum
fall to the carpet.  I wanted to taste him again!

   'You think I was slutty, John?'

   'I guess all teenage boys are highly sexed, Samantha, and especially if
naked except for black see-thru panties!'

   'His son was just as pretty as me...  perhaps even prettier, but like
all you alpha males Marcus was more interested in new meat!  On the bed he
ignored Peter and was all over me, kissing me, fondling my bum, my thighs,
shoulders, nipples, running his fingers through my hair.  And then I felt
his hand on my cock and balls, holding the whole lot in their flimsy nylon
covering.

   'Peter now had his mouth around his daddy's cock.....  I hoped the boy
would leave some for me.....

   Marcus pulled my panties down,or rather he pulled the waistband down and
anchored the crunched-up nylon under my balls, making them push forward,
stretching the skin so it was less crinkly, and almost shiny when I looked
in the overhead mirror.  I watched as he licked my balls, and then closed
his mouth around my knob.

   'Then Peter did something unexpected....he got a bottle from the bedside
table and tipped some of the contents onto his palm.  Oil!  I knew it was
oil as I felt him pull my panties aside, spread some into my arse-crease
and over my anus.  It must have been pre-arranged with his daddy!

   'So now it was easy for his daddy to finger my arse his hand inside my
panties and I felt his finger pressing against my anus, and then slide in.
I cried out, not in pain or even discomfort, but it was so strange to have
your body invaded like this, unthought of and astounding.  He was still
sucking my cock, and Peter started stroking his daddy's cock, making it
glisten with the surplus oil, as I looked up at the mirror and saw the
whole scene.

   'As his fingers found out my prostate surprise soon turned to pleasure,
and pleasure to ecstasy, and very soon ecstasy to orgasm as I came.  My
first anal orgasm, John, and one of the biggest I ever had, before or
since. My young body had just been waiting for this!

   'His fingers still up my bum, Marcus kissed me on the mouth and I
fancied I could taste my own cum as he did so...  my little cock was still
hard and responding to his continued massage.

   "Are you going to fuck him, Daddy?  I'd love to see you fuck him.  So I
can suck him the same time."

   I could see a little dark, damp patch in the pink satin of his panties
where his cock had leaked a bit of pre-cum.  My cock was not doing this
yet, but a few weeks of sex with Peter and his daddy soon started that!

   'I was not asked, just positioned by the two of them so I was kneeling
on the bed my panties off and just draped over one ankle, my bottom
sticking up in the air.  I looked over my shoulder and saw Marcus kneeling
behind me, his cock inches from my anus.  I knew I was going to be fucked
and my heart was beating.  I was frightened of course...  it looked so big
and my hole seemed so small.  But from sexy playground talk I knew it was
possible, and had felt the pleasure of anal massage.  So fear was mixed
with excited anticipation.

   'The pressure of his knob on my arsehole was almost as pleasant as his
fingers had been, but not so pleasant was the sudden twinge as he pushed
his knob in.  I cried out.  But Peter was whipering softly that it would
soon pass and be good, that I should push out as if shitting, that I would
soon be loving it, so I bit my tongue and let him get on with my first
fuck. I felt him shove again and then his thighs were against my bum and I
knew that incredibly the full length was up me.  It started to feel good as
he pulled it out as far as the knob.....  good like a nice shit if that is
not too vulgar, John!  And then when he pushed in again he touched my
prostate with it and the promised pleasure began.

   'I told him it was nice now, and that was the cue for Peter, standing by
the bed, to grasp my head and slide his cock between my lips.  My first
fuck was a spit-roast!  Would you believe my luck, John?'

   'Lucky guy!  But you were worth the risk he took, angel....'

   'Anyway, he made it last and my prostate had a real good pummelling: I
came almost immediately and so did Peter.  there were a few drops of cum I
think, as I could feel a change in my mouth, but no real spurt.  Then the
boy was wriggling underneath me so he could suck my cock while his daddy
pounded away.  I was in some world beyound this by now, a wonderful world
of naked flesh, hot mouth, and above all that meat sliding in and out of my
bottom.  I can remember thinking it was getting better and better and I
wished I had learned about it earlier....  though I was only eleven, John.
As I thought how good it was, it ended with three or four mighty thrusts
and I could imagine each one terminating in a spurt of white "seed" deeep
inside me.

   'We all collapsed onto the bed, laying side-by-side.

   'My arse expelled the cock with a fart.

   'Peter giggled and his mouth left my cock.  I was still hard and so was
he.  But his daddy was limp now.  Not like you, John.  Fuck me again, and
make sure it goes on and on and on and on this time.'

   'Third time always does, angel.  But does the story end there?'

   'Oh!  We met a lot over the next two or three years, and gradually Peter
and I were transformed into proper little transvestites.  Peter always led
the way and I was always keen to follow.  First it had been panties, then
after a bit suspender belts and stockings....then high heeled shoes.  Then
tight little brassieres and full basques.  Finally it was wigs, make-up,
gowns, blouses, skirts, and trips out with daddy and son to a little club
in the East End, where I met some other lovely men too.  By the time I was
fifteen I was two people, Jolyon by day and at school, Julia with my
special friends....

   'And now Julia would like it on her back with her legs round your neck,
sweetie.....'

   Fin for now