Note: This story was dynamically reformatted for online reading convenience.
 
 Trainee tranny: (c) Hamilton Joyce MM, Mm.  tv.

   My Dad was different from the other boys' fathers.

   My Dad was a "single parent father", unusual enough but that's just the
beginning of the difference.

   I was eight when my Mother walked out never to return.  She was ten
years older than Dad and was a City finance expert, quite high up in one of
the Banks.  Dad had been in the mail-room when she picked him out and first
used him as her main toy-boy.  They never married, but when I was born he
effectively became a "house-husband" while she climbed the corporate ladder
and I guess earned lots of money.

   I expect that by the time he was in his mid twenties she got bored with
him and found another cute seventeen year old.  She must have done some
sort of deal with Dad as we kept the apartment and all the furniture.  She
left with just three suitcases.  Big ones.

   I think there was some money each month to support me, but not enough
for the two of us so Dad had to find work, which is the start of his really
unusual difference.

   When other boys at school boasted that their dad was a fireman,
policeman or some such, I had to lie about mine.  I pretended he was a
train driver.  In fact he was a male whore, though he would have preferred
to be called an escort.  He really was quite handsome in a hippy sort of
way, and with his blonde hair in a pony-tail, his slim build and his ever
fashion-conscious clothes you could have taken him for a lad in his late
teens, not a man in his late twenties.  The gays liked him!



   I was nearly always left alone in the evenings, put to bed and then Dad
would go out to work.  Amazing he got away with this without attracting the
attention of the Child Care Department of the local council, but I was
never a problem so they never found out.  He would return in the early
hours of the morning, always with a client he had picked up in one of the
gay bars and clubs he cruised for trade.  Sometimes I would see one of his
guys in the morning as I got ready to school: mostly they were big, old,
fat and well-heeled, but some were clean cut young managerial types.  All
"suits".

   Dad took credit cards!

   Weekends and school holidays when I was at home, Dad would sit reading
and waiting for the phone to ring.  When it did there would be a minute or
two while Dad described what he could do and how much each service would
cost, then the address.  And a little bit later another of these clients
would arrive, usually stay an hour, and then leave.  I supposed he did this
all day when I was at school, and this was confirmed in the school
holidays.



   Dad was usually discrete, hiding from me what he and his customers did
behind the shut bedroom door, and I guess I would have been nine when I
found out.  I already knew a bit about sex from playground talk and jokes,
and boasting by older boys.  I knew in some detail what men and women did,
but my info about gay sex was mainly from listening to but only partly
understanding Dad's telephone chat, and enjoying playground dirty jokes: it
was altogether more vague, some of it frankly unbelievable to a nine year
old boy.

   One night changed all that!

   Dad came back unusually late, and both he and his "john" were at least a
bit drunk.  I heard dad saying "Sh!  Don't wake the lad." And then there
was a crash as one of them knocked over the telephone table in the hall. 
Another "Shush!" It was all rather Laurel and Hardy.

   Anyway I turned over and tried to go to sleep again.  It was half past
three, for God's sake!

   But there were all sorts of noises from dad's room: usually it was
impossible to hear anything as the bedroom between his and mine was used as
a spare-room and deadened all sounds.  I got up to see what was going on.

   Dad always shut his bedroom door at night or when he had a client in the
daytime, but I guess drunk he forgot or the two of them were in a hurry to
get it on: the bedside light was on too.  Clothes were strewn all over the
floor.  The bed was opposite the door, side on so I had a perfect view of
the action on the bed.  Dad was kneeling with his bum in the air and his
back bent forward so his head was buried in a pillow.  The guy was kneeling
behind him: he looked older than dad and although his cropped hair was dark
he had some grey hairs on his chest, lots of hairs there in fact and also
around his cock and balls that I could see clearly in profile.

   The guy had a boner, huge and hairy with an angry-looking knob.  He was
squeezing some stuff from a tube onto it and then from the same tube onto
dad's arse-hole.  I watched in awe.  A great mystery was going to be solved
for me.  Older boys joked about this, called it "bumming" and a standard
insult was to call another boy "bummer", but I had not really believed it
possible.  Just a story, I thought!

   I was about to find out exactly how possible it was!

   Dad looked over his shoulder and laughed.  His voice was slurred.

   "As hard as you like mister.  I'm relaxed.  Always am, especially when
pissed."

   "You've a cute bum, Simon.  You're worth the money.  Here goes."

   I watched as he first spread dad's bottom and then carefully placed his
huge knob between dad's buttocks, He held on with one hand but held his own
cock with the other and I saw his buttock muscles clench as he pushed with
all the power of a broad, muscular bum, and strong-looking hips.  The cock
disappeared up dad's poop-shute.

   I was shocked, but excited.  This was sex.  Adult sex.

   I thought dad's bum looked much less handsome than the guy's when that
hairy-holed, broad bottom clenched and unclenched its muscles as the guy
drove his pile-driver in, pulled it out, and drove it in again, over and
over again.  Dad's bum was pretty, sort of girlie, so smooth, white and not
at all muscular.  I was getting excited.  felt a tightness in my chest, and
my cock started to feel funny.  I felt for it and found it was stiff, like
dad's guy but his looked about ten times as big as mine.

   I watched as they enjoyed their sex, and without thinking I had my hand
inside the open flap of my pyjamas and was rubbing my cocklet.  That must
be instinctive, as I don't believe I had discovered how good it felt before
that night.  The guy's muscles rippled...  arms, shoulders, even his
massive thighs, especially his buttocks, and dad was obviously enjoying
it...  how could you enjoy having something that big hammering away inside
your bum.  I reached behind with my free hand and touched my anus.  My
finger would not go in.  I licked it, and moist it entered to the first
knuckle.  I was still jerking my cocklet.....  and I came.  To say it
surprised me would be an understatement: it nearly knocked me over the new
sensation was so strong and so good.  I sat on the floor!

   I wonder if my bisexuality, and my preference for gay sex was generated
that night, or merely confirmed....  Anyway, the noise of thighs smacking
against buttocks, and the slurping sound of a well lubricated cock in an
arse-hole filled the room.  Dad was moaning....  I was sure it was in
pleasure not pain.

   "Fucking hell!  You're lovely and tight, and it's fucking hot up
there..."

   "Shush!  Or the boy will hear.  Shush, mister."

   "Your fucking boy is watching us now, so don't worry about him hearing!"

   Dad lifted his head from the pillow and his eyes met mine.

   "Oh fuck!"

   The guy was still fucking in and out, his hairy pubes and thighs
crashing into Dad's smooth and nowhere-near-as-strong bottom.  He slapped
Dad hard on the buttocks.

   "Shut up, Simon.  Too late now.  And I'm fucked if I'm going to stop. 
This is too good!"

   I watched for at least ten minutes as Dad was fucked in the arse and the
guy spanked him in the same rhythm, sometimes pausing to run a finger nail
down dad's slender white back, sometimes kissing him there, sometimes
pausing and leaning over to kiss his neck while feeling his cock and balls
under him.  For the last five minutes Dad was moaning and almost shouting
things like .  "Yes!  Like that!  Fuck that's good.  You're hitting the
spot now, mister.  Jeez!  You're a great fuck.  Go on!  harder, faster,
faster." And at last, "I'm fuckin cumming.  You've made me cum.  Great
fucker.  Yeeeeees!  Yeeees!"

   I was to discover that dad always swore when he was being fucked,
sometimes much worse than this: I never heard him swear any other time!

   "Me too Simon.  Me too.  Greeeeeat!  You're a fuckin hot little fuck! 
Yeeeees!"

   They then fell sideways on the bed, still joined at arse and cock. 
After a couple of minutes I watched as the guy pulled out and I saw he was
wearing a condom (playground word was "spunk bag" and I now saw why the
boys called it that: it was full of what could only be sperm, an incredible
volume).  He tied a knot in it and threw it on the floor.

   I crept back to bed.  I awoke in the small hours with a stiffy again,
and put what I had just learned to good use by rubbing it and
finger-fucking my anus until I was rewarded again by a lovely orgasm.

   I was probably about ten.

   In the morning the guy was gone and Dad didn't mention my peeping at
all. But after that he always left the door open for me to watch and I made
no effort to hide.  My sexual education increased as I saw oral sex,
fucking in every conceivable position, and the "wilder shores of love too",
rimming, fisting, S&M, bondage, and really weird role-play.

   I now knew how so I wanked a lot (a lot for a pre-adolescent at any
rate) and started cutting out and collecting pics of men and boys I
fancied. I realised I was gay, or at least bisexual with a preference for
cocks over pussies, just like my dad.  When boys at school boasted about
girls or described probably imaginary sexual encounters I stayed quiet.....



   For several weeks I just loitered at the doorway watching, and it was
clear most of the guys enjoyed being watched by a lad in his pyjamas and
often our eyes would meet.  I learned then that even a young boy could be
sexually desirable to some men: the look in their eyes was unmistakeable. I
suspected for some of the guys a young boy was not only desirable, but
especially desirable!

   But one night a regular customer beckoned me over.

   "Come and watch, Lenny."

   I stood by the bed as the two sucked each other's cocks, watching them
fondling each other the man laying on top of my Dad, his hips shagging up
and down, his cock ramming into daddy's mouth and I wondered again how
daddy could enjoy it.  But he was loving it, with his arms round the guy's
hairy arse, one hand in the actual arse-crease and half the slurping noise
was from his cock in the guy's mouth.  I don't think either of them came,
but the guy came off daddy, greased his cock, a huge weapon it seemed to
me, straight and with blue veins on it like ivy up an oak tree, a purple
helmet at the top broader even than the shaft of his cock.  Amazingly it
went in and the guy fucked him, Dad on his back with his legs over the
guy's strong, beefy shoulders.  Any doubt as to whether it was good to be
fucked in the arse was removed by Dad's usual panting, moaning, and
foul-mouthed encouragement, and finally by the great streamer of white
spunk that splattered up over his hairless chest, over his face and into
his hair.  I rubbed my cock while I was watching and became so excited,
especially when the cum splattered that I had one of my own orgasms,
powerful but "dry" of course.

   The guy saw this, saw my breathless face and twitching cocklet, smiled
and winked at me.  I'm sure he would have reached out to fondle me if Dad
had not forbidden it.  I would have liked that....

   Dad said nothing about it, but when I next looked in there was a chair
by the bed.

   Dad had a "no touching" rule as far as I was concerned.  I was allowed
to sit and watch, but was not to play any other part.  When I tried to
fondle a particularly nice bum while the guy was being sucked off, dad
stopped, took me over his knee and spanked me.  The guy clearly enjoyed
watching that and to be honest I quite liked it too...  or at least my cock
did, but I certainly did not want to be banished from the room which was
the threat if I was ever tempted to join in again, however mildly or
fleetingly.

   Similarly the first time a "john" leaned over and fondled my bare
leg.... not able to reach my cocklet hard as usual....  he was told to
desist or he would not visit again.

   That did not stop me imagining what it would be like to be the toy-boy
for the more handsome of his guys, fantasising being fucked in the mouth or
the anus, being spanked like some of them spanked daddy...  Being tied to
the bed and used....



   I would have been about eleven, voice breaking and balls itching with
new fine-hair growth, when I saw a completely new side of my daddy, and an
exciting one too.

   It was a Saturday and daddy had been busy with three guys in the
afternoon while I watched sport on the TV.  I heard daddy singing in the
shower at about five....  the match had just ended.  He always showered
after his daytime business if he was going out to a club in the evening.

   Anyway, he was a lot longer in his room than usual and his door was
shut, I called out and asked when he wanted his burgers and chips which I
would microwave for both of us.  He said "Seven o'clock" and that he would
go out about eight.  Not to wait up!  I seldom did in any case, though his
night time clients were a better class of men than the day-timers.  Often
young and vigorous, and if older, fat and very rich.  If they made enough
noise to wake me it would usually be worth while getting up and watching
from beside the bed.

   Seven o'clock and I had just put the stuff in the microwave when she
appeared.  She?

   SIMONE!

   Dad transformed into a drop-dead sexy female.

   He stood in the doorway of the kitchen and pirouetted in his gold high
heels.

   "Will I do, Lenny?"

   He looked fantastic with his pony tail undone and that blonde hair
falling shining to near-naked shoulders.  Heavily made-up, with red
lipstick and eye-liner together, I'm sure, with lots of stuff to cover any
stubble, his face was a hundred percent feminine.  He was wearing a green
silk dress, tight over what must have been false breasts, high to the neck
and with a ribbon to the back of his neck, leaving his arms and shoulders
bare, and very white.  I had never before noticed how slender his arms are,
and his hands sort of elegant, red nails same as his lip-stick.  The dress
was mid-thigh length with a long slit up one side.  One of those Chinese
ones...Chongsans" or some such word.  He was wearing tan stockings: as he
spun round I could see they had straight seams.  The stockings and shoes
made his ankles look especially sexy.  The only thing not womanly about him
was his slender hips, and his bum was smaller than most fems.

   All in all, he was a convincing, tarty girl dressed to go clubbing.

   I told him just that, and he was pleased, glowed with pleasure.

   "I reckon I'll outshine the other trannies at Samantha's....  that's the
tranny club I've decided to go to tonight.  Get plenty of rich married guys
there who would not fancy a male rent boy, but into transvestites."

   That was more than Dad had ever said to me about his work, and I guessed
it was not only his appearance that was feminised by dressing.  He was
friendlier, and after dinner he kissed me before going out, not a sexy
kiss, but he would never have done that in his "Simon" persona.  He was
walking like a woman, hips wiggling.  Jeez!  Even his voice was up an
octave!



   From then on it was a Simon answering the phone morning and afternoon,
but early evening and always when he went out cruising it was Simone.  I
only occasionally watched from the bedside when he was male, but often when
he was female, and decided I was certainly bisexual.  I started a scrapbook
for girls and trannies....  in lingerie mostly....  and I loved ones of
trannies with stiff cocks.  I still kept up my male book, but used both for
masturbation fantasies...

   My masturbation had also taken an unusual twist.  What I found most
exciting to watch was when my daddy sucked his partner's cock, as Simone
with her flowing blonde hair, shapely legs always in stockings, sometimes
fishnet sometimes black and glossy, killer high heels, lacy bra covering
her false tits, sexy suspender belt, either no panties at all or a lacy
thong with open crotch.  He (she?) always swallowed, and I wondered what it
would be like to feel that hot meat in my mouth and the spurts of cum
against my palate and tongue.  Even the thought made me horny, and it was a
constant theme of my night-time fantasies.

   Then I discovered I could suck my own cock: it was difficult but worth
it to feel the warmth and wetness of a mouth around it, even if it was my
own.  I imagined myself as Leonora, a little girl sucking a gentleman's
cock.  My fantasy partner was always muscular, hairy, groomed.....  and
wealthy.  I wanted to follow my father into his (her?) chosen profession! I
think it was about this time I produced my first drops of cum, not spurts
yet, but I was entering adolescence.

   And my sexuality was becoming clear to me: I was bisexual with a
preference for strong, dominant males, and a lust for lingerie, for
make-up, for sexy shoes.  I wanted to be a transexual like my daddy and
have cocks to suck.  I practised anal sex with an old mahogany chair-leg,
polished smooth and as broad as a man's cock, finger fucked myself while
bent double sucking myself off, and was, to be honest, ready to be fucked
at the age of twelve.

   But all daddy would let me do was watch!  And his "no touching" rule was
not negotiable.  I remember thinking it was not fair that he would not even
let me feel one of those sturdy muscular bums, or handle one of those
fierce, angry red or purple-crowned shafts.

   Greatly daring I stole one of daddy's open-crotch panties from the
laundry basket and sat in my chair watching his foreplay with a man he had
picked up in Samantha's.....  wearing my scarlet nylon and lace confection.
No comment from daddy, but his eyes met mine and he smiled, a rare occasion
he even acknowledged my presence when he was "working".  The silk round my
balls and cocklet felt so good, and the guy positioned himself on the bed
when he came to fuck daddy so that he could see me...  pretty boy, trainee
tranny....  I knew he was looking at me while fucking daddy, and since my
cock was stiff I let it push through the opening and stand clearly visible.
The guy gasped, and I am sure he imagined he was fucking me while in fact
shafting my daddy.  He came quicker than usual, and I could so easily have
cum too if I had as much as touched my cock.



   Daddy knew what effect I was having on his customers and started
charging them more to have the boy-girl sitting by the bed.  To enhance the
effect he bought me some more panties and suspender-belts, stockings
(difficult to get good quality small enough but he found them) and a pair
of lovely, sexy silver high heels.  I took to wearing my long hair down to
my shoulders like Simone and spent ages shampooing, drying and then
brushing it till it shone.  (No problem at school: several lads wore
pony-tails, following the fashion: shit, even macho footballers were doing
it....  and waxing away their body hair!) I would have loved to wear
make-up, but probably I was quite pretty enough with my full lips and
English-rose blonde complexion without cosmetics.  Still a no-touching
rule, though.

   The rule was finally relaxed, presumably because the guy, a regular
visitor, had pleaded....  and I assumed paid more.  He was well-dressed,
obviously upper class with that bearing and accent (we can spot these
things in my country!), and wore a wedding band on his ring finger.  He was
charming, as well as being fit for his fifty or so years....  the body of a
man twenty years younger.  My sort of guy, muscles, hairy, groomed!

   I can remember everything about it: Simone was wearing a lilac satin bra
and the matching suspender belt along with black fish-net stockings and
black high-heeled sandals.  She was kneeling over the guy, who lay with his
head lolling over the edge of the bed so he could see little Leonora,
scarcely six inches away from him.  Simone was sucking the guy's cock, but
I was sure she would be stopped before making him cum as he always fucked
her and did not seem good for two bites of the cherry, as it were.  I had
black panties, high-cut and with a transparent front panel to show off my
cocklet, big enough now for the head to peep over the waistband.  I had
brand-new glossy stockings, black, and my silver high heels, that were too
tight to walk in now but sexy to wear sitting by the bed.

   The guy was watching me, and I slowly rubbed the front of my cock
through the black nylon, and as I did so I could see beads of sweat break
out on his forehead.  Then he reached out towards me, and touched my
stockinged leg.  It was like a jolt of electricity to me as his hand moved
up the hard glossiness to stroke my soft flesh above the stocking tops.  I
expected him to be told to stop in no uncertain terms, but daddy just
sucked away at that meat without apparently noticing.  The hand covered
mine over my crotch, and when I withdrew it, he was left felling the young
lad's cock through real sexy knickers.  He slipped his hand inside the leg,
and was holding my naked cock.  Then it was my balls, fingering them,
gently squeezing: back to my body, stroking my belly, pulling the waist of
my panties down to look closely.

   I reckon I was twelve when this happened, for two reasons.  The first is
I clearly remember him combing my new pubic hair with his fingers but I'm
sure my balls only had the lightest fuzz.  Second, when he rubbed my
cocklet I came, quite a lot of spunk covering his hand.  I saw him lick it
from his hand: he wanted my cum, but I never saw him suck Simone off, not
ever.  A boy in drag was one thing, a mature tranny's spunk less
appetising!

   From that evening on quite a few customers were allowed to fondle me,
though at arms' length, and I was never allowed to touch them with my hands
or lips.  Those who did get to grope me nearly always made me cum as I
found it very exciting to see their cocks twitch and the pre-cum well out
of the eyes of their crowns as they stroked my legs, fondled and
masturbated my cock.  Also, my cock was certainly growing: nature I
suppose, plus a lot of use!  The guys who could pay were, I think wealthy:
I found you could tell a guy's wealth by his shoes....  hand-made brogues
equalled well-to-do, trainers guys who had cobbled together just enough
cash for half an hour with Simone, none left for the lad's favours!

   There were several months of this half-way house to being a rent boy
before I was finally initiated.

   Daddy had been especially generous, buying me new high heels...  gold
this time, and ones I could actually walk in without pain, new
stockings.... the expensive fine sort that are not stretch, but made to fit
even a slender boy-girl....  new lingerie, knickers and suspender belt in
black nylon at the front with satin across the bum, cut boxer-shaped, but
transparent at the level of the balls, and with lace fern designs over the
penis.  I loved them, and got hard just looking at myself in them in my
bedroom mirror.

   When he came out of his shower after the daytime session, I expected him
to dress, have dinner and then go to the Club.  But tonight was different.
He had me shower and then showed me how to use an anal douche.  I was
fascinated: this was a sexual mystery I had never even heard of....  I had
wondered why daddy and his partners were never shitty but my fingers and
faithful chair-leg often were Now I understood.

   He watched as I dressed in my room....  new knickers, stockings, the
lot. And then for the first time he had me varnish my nails and use a
matching pale pink lip-stick.  With my blonde hair to my shoulders I looked
like a very pretty girl, flat-chested of course, but sexy as hell!  My cock
made a tent in my knickers but daddy just held it a second and laughed....
this was the first time he touched me sexually, and also the first time I
really felt like Leonora and not just Lenny in knickers...

   He did not go out, but dressed as carefully as if Simone was cruising..

   We ate the goulash I had microwaved and at eight our customer arrived.
It was the guy who first made me cum while I was watching, and I was to
call him Uncle Roger (I know his full name now...  and he is titled.) He
handed Daddy a bundle of notes that daddy did not bother to count, but shut
in the side-board drawer before taking us to his bedroom, where I sat on my
chair and watched Uncle Roger undress while Daddy lay on the bed waiting to
be fucked in the mouth as usual.

   The new lingerie and shoes, the make-up, the feeling that something new
and exciting was going to happen, all that tension made my cock stand and
spoil the line of my knickers!

   As usual the two lay on the bed, but this time they did not kiss: both
looked at me, and Uncle Roger smiled and nodded.

   "Come here, Leonora, on the bed with me..."

   Jesus.  This was promotion!  I was going to be allowed to join in at
last.  I think I was still four months short of my thirteenth birthday, but
I already had a huge knowledge of gay sex, without ever having experienced
it myself.  This was about to change, and I knew it, with a mixture of
eager anticipation and not a little sheer terror.  Would it really be good?
Might it hurt?  Suppose I was not what the guy had paid good money for?  I
can remember the pulse in my temples throbbing so loud I thought they must
be able to hear it too.

   I lay on the bed beside this hairy, muscular man, who smiled at me and
whispered, "We're going to make love, Leonora, I know it's your first time
and I want to try to make you enjoy it so you remember it with pleasure.  I
promise I'll be gentle."

   And he was, and I did, and I do!

   Daddy got up, went round the bed and now it was him sitting on my chair
and me kissing and caressing the 'john'.  Promotion indeed!

   The secret was, of course lots of foreplay plus the fact I was up for it
and really fancied this guy.  I had used him often to fuel my masturbatory
fantasies.  He pulled me over so I was laying half on top of him, his arms
around me, one hand stroking my back, the other fondling my bum through my
satin knickers.  Jeez, how these males love the feel of a firm little bum
in satin!  We kissed for a long time, his tongue in my mouth and then mine
in his.  I had my arms around his neck...  he was one of those guys so
hairy he even had tufts on his shoulders.  Lovely!

   After a while his mouth was on my nipples, licking and nibbling them,
then his tongue circling round my navel, poking into it and making me
giggle as it tickled.  He was feeling my stockinged legs all the while, and
his mouth slowly heading south over my newly waxed belly to nuzzle my
crotch through my knickers.  Another lingerie fetishist!

   I lifted my bum and he drew my knickers down.  My cock was standing for
him, of course, and I knew the warmth and wetness of a mouth not my own for
the first time.  He sucked me, his head bobbing up and down, and then he
licked my tight little ball-sack, taking one ball into his mouth and
sucking it.

   I could not reach his cock with my lips but I could with my right hand
and I held it, feeling the flaring knob, and the veiny shaft, so soft on
the outside so steely hard inside, so hot and with a pulse throbbing.

   "Can I kiss your cock, please, Uncle Roger?  I've never...."

   "What, not even Simone's?"

   "No!  She's my daddy!"

   "Oh, you little sweetie, of course you can.  I'll tell you when to
stop!"

   So I got to suck my first cock...  not counting my own!  The knob
stretched my jaws, so I mostly licked the shaft and kissed the knob, where
I tasted my first pre-cum....  no taste in fact but a silky feel I remember
enjoying.

   "That'll do, Leonora.  That's enough.  We're going to make love
properly...."

   He turned me over on the bed and I felt his hands part my buttocks.  I
know I tensed with sudden fear, a terror that his huge flaring knob would
hurt me, perhaps even split me....  too much porn fiction on the internet.
Rapes!  In fact he just wanted to look at my anus, and praise it as being
'a secret rose' before I felt his stubbled chin on my soft flesh and then
his tongue licking that secret place, penetrating it.

   That felt good, though I giggled as it tickled.  It certainly relaxed
me.

   The oil bottle was in it's usual place on the bedside table.  How often
had I seen it squirted onto Simone's anus?  Well this time it was mine to
lubricate Uncle Roger's finger as it penetrated.  That did not hurt...  but
he did not find my prostate, which I guess was not much of a lump yet at my
tender age.

   He turned me over and we were mouth to mouth as he finger fucked me,
completely relaxing me as he used two and then three fingers in me.

   "There, Leonora, I've three fingers in you and that's more than the
width of my cock.  OK?"

   "It's OK, uncle Roger."

   "Kneel down, your head in the pillow."

   I heard the spray as he lubricated his cock and than daddy interrupted.

   "Sniff this, Leonora.  It'll help relax your bottom and make it feel
good..."

   Poppers!  And, yes, they did work as I felt only the slightest pain as
Uncle Roger parted my buttocks, rubbed his knob a couple of times up and
down my cleft, positioned the knob and pushed.  He had prepared me well
with the fingers and the poppers and I gave only the slightest flinch as
his knob popped in, followed by his full eight inches till I felt his hairy
thighs against my bottom.

   It didn't hurt, but just felt very, very full!

   He slowly withdrew as far as his knob and then slowly in again.

   I felt nothing except that fullness, no pleasure but could hear from his
whispered comments it was good for him.

   "So lovely!  Little Leonora!  So tight and hot.  Jesus!  What a fuck."

   As he speeded up his knob must have started to hit on my adolescent
prostate because it began to feel good.  Strange, but sexy.  He reached
under me and grasped my cock, starting to rub it in time with his thrusts.

   "Uncle Roger, I'm gonna cum."

   He stopped rubbing and the moment passed.  But he was getting close, and
I knew it as his thrusts became sharp jabs, his thighs crashing into my
bottom.  Then with three huge stabs he came, and I imagined his hot cum
spurting deep inside me.  His cock moved easily, lubricated by all that
slippery cum, as his excitement wound down and he rested before pulling
out.

   I giggled, a bit embarrassed as his exit was accompanied by a fart!

   "You didn't cum, Leonora?"

   "I'm sorry, Uncle.  But it was nice."

   "Nice for me too, and now this will be good too."

   His mouth around my cock and this time no stopping as in seconds, it
seemed, I was squirting into his mouth and he was swallowing.



   From then on, favoured clients had me in the bed along with Simone, and
for a premium they could suck or fuck both of us.  More and more it was
obvious it was my teenage body they wanted, my cute little butt and cocklet
more than daddy's more conventional adult charms.  But he was earning lots
more money now and seemed content at first.



   This went on for a couple of years, but when I was nearly fifteen daddy
took me along with him to Samantha's.  I had been taking singing and dance
lessons each week for about a year and was persuaded by the DJ to follow
the usual drag artist act with a song and dance of my own.  I was an
instant hit: much prettier than the usual tvs and certainly younger and
fresher I had also been well taught and rehearsed.  I did a camp version of
"My Boy Lollipop"!  Several guys wanted me that night, but I selected the
best-looking, fittest one and took him home, along with Simone and her
catch for the night.

   This became our usual routine four or five nights a week, and we were
really coining it!  My school reports became woeful!

   Daddy enjoyed the money, but was jealous of my looks.  I knew that,
although he was never unpleasant, and never wanted sex with me.  I
respected him for that...  But more and more the guys wanted me, and less
and less him, and despite the money I'm sure it rankled.

   So it must have been something of a relief for him when Theo made me a
life-changing offer.  It came just right as it was two weeks before my
sixteenth birthday, and I had told the school I was leaving.  I had been
taking hormones for about four months, and breasts were just beginning to
grow.  One of my men from Samantha's was a medical doctor and he supervised
the treatment checking me each month and ensuring the mix of hormones
allowed me to start to grow tits, but still did not catastrophically affect
my cock's erections.

   The doctor did not charge me for the treatment, pills or injections, but
checked in person that my cock could still stiffen, and that I could still
cum with his cock in my arse.  I always dressed as Leonora for him.



   Theo was, is still, a hedge-fund guy in The City, fabulously rich though
he did not have the usual villas and country estates that go with that sort
of wealth, content as he was with a London town-house, a big one with lots
of additions, including a swimming pool and a garage under it and a top
floor altered so that from the back there was a view through huge windows
over the trees and buildings below.  Most of this was his living-space, but
his bedroom/playroom was alongside.  The front of the house was protected
as being in a conservation area.

   He knew I had an arrangement with my doctor and was not at all jealous
or possessive: in fact he used to lend me to his friends and colleagues,
and when he gave one of his parties I was treated not as his partner, but
as one of the show-girls, models, and tvs he had along to entertain his
guests.

   I had a good time: he was a fit and vigorous guy in his thirties, and
very very generous with his gifts, often of valuable necklaces and rings
Soon after I joined him he had my belly-button pierced for a big emerald
that I often wore for him.  He gave me other gems, red and blue, white
diamonds, gold too all with the connector to my piercing.  Lots more too.

   His friends were generous with money, and with my monthly allowance from
Theo (on my credit card) and presents from his mates when they enjoyed my
feminine bottom and masculine cock, I soon had a very substantial bank
account.  Money was of little interest to Theo...  he had so much!  I was
interested in money.....



   As the months went by my breasts grew and my skin softened (I kept my
whole body waxed as well): My hips broadened a bit, but I kept my tiny
waist and long, slender legs.  When I had nice, rounded B-cup tits I
stopped treatment, and I still had a serviceable cock!

   Now I was always Leonora and never Lenny!  It was towards the end of my
stay with Theo that he got me a new persona....  birth certificate,
passport, National Insurance number, driving licence and all the back
history needed to prove I was Leonora Motz, born in Pimlico same date of
birth as Lenny!

   After the first year of my stay with Theo he started to pimp me out to
business contacts: I did not have any choice in this, but did not need to,
as most were fit , young City go-getters like him, or if older then with a
life-style that included the gym.  I enjoyed the variety of partners.... 
my early life as a whore I expect....  and certainly appreciated the gifts
and discrete payments that followed these meetings.

   This idyllic life lasted nearly four years in all, but inevitably I was
replaced as Theo's favourite.....  by a girly-boy about fifteen years of
age, a pretty little thing half-Asian, half-Caucasian, with lovely glowing
golden skin, perfect teeth, long shiny black locks.  She was tv, and
slender with lovely legs.  I never had her, but got used to seeing her
about the house.

   At last Theo bit the bullet and told me it was time for me to move on.
He sweetened the bitter pill by handing me the keys and deeds to a flat in
St Johns Wood near the cricket ground....  the freehold worth a seven
figure sum!  I had one last week with him in The Bahamas before we kissed
goodbye at Heathrow, him back to Mayfair, me to NW8.  No hard feelings,
just gratitude.

   My contacts...  his City colleagues and friends....  stayed very much in
touch with me and formed the basis of a successful escort business.  Very
expensive I was!  When I ran into Theo at parties or clubs, the theatre and
so on, as I sometimes did we always greeted each other as old friends, and
we both meant it.....

   So if you are wealthy and into chicks with dicks, look out for Leonora,
the girl with the emerald in her belly button.