Date: Tue, 7 Apr 2015 10:07:07 +0100
From: John McQuillium <johnmcquillium@hotmail.co.uk>
Subject: My first transsexual sex part 1

My first transsexual sex part 1

The following is a true account of my first encounter with a transsexual.
It includes transsexual with boy, TS with B,B and TS with B & G sex.

Comments gratefully received at johnmcquillium@hotmail.co.uk

Usual blurb about don't read if you are underage, etc.

Also why not make a small donation to Nifty so they can keep up the good work.

  On my very first day of 6th form college, when I was a month shy of
turning 17, I was caught being fucked by another boy in a toilet cubicle on
campus.  Luckily the lad who discovered us didn't report us to the teachers
but he did spread the rumour that we were backdoor Berite's around the
college.  Matt and I had to work hard to convince everyone we were
bi-sexual as it was a co-ed college and we didn't want to scare off any
potential female dates.  Even more luckily not only did our co-students
accept our sexuality without issue it also led to some great sex with both
sexes.  The well known fact I was an out of the closet bi- sexual drew
transsexual Sadie to me.  We were like chalk and cheese with me being a
confident witty popular student who was already on the rugby team.  Sadie
was a quite shy wallflower who I had never even noticed until she spoke to
me and when she did she was shy and embarrassed about it.

  Looking at Sadie I thought she was a slightly geeky, plain looking flat
chested girl.  She had really dark blond hair that was almost hazel and
came down a couple of inches past her shoulders.  Sadie had a pale spot
free face that was geeky looking but with cute undertones.  You know the
type, spoilt by glasses but take them off and you see there is more to her
face than first meets the eye.  Looking at her face I had no reason to
doubt she was anything other than a girl.  It was a very feminine face and
gave not the slightest hint she had a cock and not a cunt between her legs.
She was wearing a zip up top that had alternating pink and light grey
horizontal stripes.  She had bumps for breast but they would have struggled
to fill a training bra let alone an A cup.  She was also wearing a pleated
tartan skirt popular with Japanese women trying to pass off as schoolgirls.
Her pale slender legs were silky smooth.

  Sadie first approached me in the student's common room one afternoon.
That lunchtime I had played in a rugby match and Sadie had been one of the
spectators.  At the time I was reading a book and was only vaguely aware
that someone had sat close to me.  "You played really well."  I heard a
feminine voice say.  When I looked up I saw a girl wearing glasses whose
pale cheeks had flushed light pink.  Her face was like those magic eye
pictures where it didn't stand out unless you looked at it hard.  On face
value it was plain, geeky and wouldn't stand out in a crowd of two.  But
the more I looked at it I saw it had some underlying cuteness.  "Thanks.
Are you a fan?"  I asked as after breathing rugby is the most important
part of my life and I could talk about it all day long.  "No.  That was the
first time I've seen a match."  Sadie said with her cheeks going a slightly
darker pink.  Despite my mind saying "if you've never seen a rugby match
how can you say I played well" I kept quiet.  There followed an awkward
silence as I didn't know why she had approached me and Sadie was painfully
shy.  "I'm John."  I said trying to either get a conversation going or
making introductions so that we could part.  "I'm Sadie."  She replied in a
voice that gave no hint that she was anything other than a girl.  "Is it
true you're bi-sexual?"  Sadie then blurted out with her cheeks going from
pink to bright red.  Well she doesn't beat around the bush I thought.
"Yeah."  I confidently replied as I prepared my sarcastic tongue to unleash
a counter-triad if she was homophobic..  "I'm so glad.  I'm a transsexual
and I've never been able to talk to anyone about it."  Sadie replied with
relief in her voice.

  And that was how it all started.  I won't bore you with the rest of the
conversation but it transpired Sadie was a virgin transsexual who was
attracted to mainly boys but some girls.  Needless to say Sadie didn't
remain a virgin for long as I saw to that.  After college I cherry popped
her virgin mouth and arse, gave her, her first ever blow job and let her
fuck for the first time.  The following lunchtime I sucked her off behind
the bike shed whilst Mark fucked her arse.  Mark was a raging bi-sexual and
was the boy who was fucking me when we got caught on the first day of
college.  Then that weekend I introduced Sadie to the bi-sexual girl who
lived next door to me for Sadie first taste of pussy.  It was hot watching
a chic with a dick fucking another girl.  It is those three encounters that
this write up is about.

  Appearing on the face of it a girl but with a cock between her legs meant
Sadie's choice of boyfriends was limited.  Being the subject of bullying
for cross dressing at secondary school had made her painfully shy and
lacking confidence.  Therefore I could have had a face like the back end of
a bus and Sadie would have slept with me as I was bi-sexual and she was
eager to lose her virginity.  However genetics have been kind to me and at
the time I had short blond hair spiked up at the front.  My face was as
cute and sexy as Alexander Ludwig's although mine was deeply tanned.  My
eyes were blue and I had lush red cock sucker's lips.  My body was as
tanned and toned as Tom Daley's but being a nudist meant my tan was an all
over one unlike Tom's.  My smooth chest was sculpted and my biceps were
buffing up.  My abs had a nice washboard and thin treasure trail leading to
a small dense bush of trimmed short blondish brown pubes.  My tanned cock
was uncut and a fat 9.5 inches.  Around back I had a tanned perfect bubble
butt arse that was just starting to grow peach fuzz.  Playing rugby and
cricket had given me sexily shaped legs covered with golden hairs.

  After college on the way to my house Sadie was like a shy but excited
giggling school girl.  Her girlish face, petite body with minor bump
breasts and her clothing suggested that she was a girl but to anyone
unaware they would get a shock when they dived into her knickers.  Sadie
had a love hate relationship with her cock.  On the one hand she hated the
look of it and the fact it reminded her she wasn't the true girl she
mentally thought she was.  On the other hand it brought wanking pleasure
and orgasms that all teenage boys enjoy.  As my parents wouldn't be back
from work for a couple of hours I decided to deflower Sadie in my bedroom
rather than the den above the garage which I used whenever I wanted to fuck
but my parents were in.  Sadie wasn't the first or last virgin to be
deflowered in my bedchamber but she was the first transsexual in there.

  As Sadie was a virgin I decided to take it slowly despite the fact I
wanted to rip her clothes off, see my first transsexual naked and then fuck
her senseless.  To begin with I just kissed her and squeezed her bum
through her pleated skirt.  It started with just lips but I soon brought
our tongues into play.  Once we were passionately snogging I started the
undressing.  First I unzipped her pink and grey stripped hooded top to
reveal a white tee shirt with a girlish floral print on the front.  That
came off to reveal a training bra containing two small bumps.  When I took
her training bra off I saw two small breasts which were similar to those of
a girl just starting puberty.  It wasn't the flat chest of a boy but they
were bigger than just being puffy nipples, yet were far from being well
formed breast of even a girl in her early teens.  Her stomach was flat and
firm and her skin all over was a milky white.  To catch up I pulled off my
tee shirt.  Sadie's hands went straight to my subtly sculpted chest and her
eyes looked at it with lust.  My tanned hands went to her tiny tits and
felt they were squishy but natural.  There wasn't much to play with but her
nipples did seem sensitive and rapidly stiffened.

  We resumed kissing as we groped each other's tits.  After a bit I undid
Sadie's skirt and let it drop to the floor.  Sadie was wearing white lacy
panties that contained the outline of a hard cock ending with a pre-cum wet
patch.  When I went to pull her panties down Sadie held them up as if not
wanting to shatter the illusion.  However she soon relented and I pushed
them down.  Sadie naturally had no treasure trail and she had shaved off
her pubes, but had they grown out they would only have been a really small
bush anyway.  Her cock looked like that of a boy in his mid teens.  It was
five inches long and slightly slimmer than average.  She was circumcised
with the swollen knob slightly bigger than the shaft.  It was pale although
slightly pinker than the rest of her and getting more so towards the knob.
Hanging below was two balls in a tight pale, naturally hairless sack.
Seeing Sadie naked she was a girl of four parts.  Her face was definitely
that of a girl in her late teens yet her breasts were those of a girl just
entering puberty.  Her girlishness then stopped at her sex organ which was
that of a boy in his mid teens.  Finally her legs were asexual as they
could have belonged to a boy in his early teens or those of a girl who only
needed to shave them once in a blue moon.  Being bi-sexual Sadie seemed to
me two for the price of one.  Already I had enjoyed the pleasures of being
fucked up the arse by girls wearing strap on dildos so sex with Sadie would
be similar but the cock would be real and could pump cum in my arse.

  After checking out Sadie's tackle I exposed mine.  As usual I was going
commando so when I pushed my tracksuit bottoms down all was revealed.
Sadie had never seen a cock before other than her own so she had no idea
what to expect but instinct told her I was well hung.  My tanned cock was a
fat 6 inches in circumference and 9.5 inches long.  It dangled down under
its impressive length and meaty weight.  Behind were two big balls that
were over- productive even for a teenage boy.  It was that meaty monster
than was going to pop her anal cherry.  Her eyes grew saucer wide and her
geekish but cute face had a shocked expression with her thin red lips an O
that I wanted to plug with my cock.  "Is it supposed to be that big?"
Sadie asked still staring at my cock with shock.  "No most boys my age are
5 to 7 inches, mines 9.5."  "It fits in a bum?"  Sadie than asked.  "Yeah
I've fucked plenty of arse with it, both boy and girl and I've taken even
bigger cocks up my own arse."  I said in the hope I wasn't about to lose
her.  "It'll hurt you to start with but that happens the first time for
everyone."  I said as I backed her up to the bed before laying her on it.

  With Sadie on the bed I got into the push up position above her.  So as
not to touch her cock I supported my weight on my forearms and knees.  My
big fat cock throbbed on her stomach and flooded her navel with pre-cum.
Then I started kissing her again.  This went on for about five minutes
before I started nibbling her left earlobe before nuzzling the side of her
neck.  Then I kissed my way to her tiny left breast and began nibbling her
bullet hard nipple.  Sadie moaned and squirmed with pleasure beneath me as
she had someone stimulate her small breasts other than herself for the
first time.  Her breasts might have been small but they were obviously
pleasure spots and not just the nipples and halos.  Every time I groped the
small mounds of squish flesh Sadie moaned with pleasure.  Each nibble of
her hard nipples made her cock jerk and slap my abs splattering them with
pre-cum.

  After giving her breasts a good working over I kissed down her flat firm
stomach to her hard throbbing cock.  Looking at her lustfully I licked from
the base, along the throbbing shaft to the swollen pre-cum soaked knob.
Sadie gasped with pleasure and arched her back when I took her swollen knob
into my mouth.  For the very first time Sadie was experiencing the
pleasures of a hot wet mouth sucking on her knob.  As I sucked it I swirled
my tongue all over but paid particular attention to the sensitive
underside.  Her geekish but cute face had a stunned expression not
believing that something could feel that good.  After a minute of sucking
her knob I wanted to show her there was something even more pleasurable and
swallowed her 5 inch cock whole.  Unfortunately it proved too much for
Sadie and she blasted a bolt of cum down my throat.  Quickly I pulled my
mouth up to catch the remaining seven squirts on my tongue.  Her cum had
the consistency of a teenage boy's but it was sweeter and less salty.  It
was still tasty and made my tongue buzz.  "I'm so sorry."  Sadie
breathlessly apologised with her once pale face now flushed pink from
orgasm.  "Don't worry it just means you'll last longer this time around."
I said after swallowing her cum.  Then I resumed sucking her cock which
didn't lose its hardness or get too sensitive after orgasm.

  The second time around Sadie did last longer but she still came within
ten minutes.  It was hardly surprising as Sadie was a virgin and I was an
expert cock sucker.  Also every teenage boy wanks at least once a day but
Sadie's love hate relationship with her cock meant that she wanked much
less frequently so it was less used to stimulation.  Again the first bolt
of her cum blasted straight down my throat with me catching the other seven
on my tongue.  Sadie might have been mentally a girl with girlish features
but she had the cock and balls of a virile teenage boy.  "Now time to eat
out your pussy."  I said after swallowing her tasty cum.  Pushing up her
legs I exposed her pale arse that was naturally hairless.  Seeing her tiny
pink pucker I knew she was going to be in a lot of pain when I popped its
cherry.  Sadie gasped with pleasure and her pucker quivered when I dragged
my tongue over it.  To start with I licked up and down it before circling
around it.  Sadie squirmed and moaned with pleasure as she had her arse
stimulated for the very first time.  She had never been tempted to stick
anything up it or finger it whilst wanking.  Now she had a hot wet tongue
licking it for all its worth.  Then I started tongue fucking it by stabbing
my tongue in and out and wormed it in as deep as I could.

  After eating out Sadie's pussy/arse for about ten minutes I told her to
pass me the tube of lube from my bedside table.  "Hold up your legs."  I
instructed Sadie.  Then I lubed up the five digits of my right hand.  Next
I took her swollen knob into my mouth and began sucking it as a diversion.
The tip of my middle finger pressed against Sadie's tight virgin arsehole
and pushed.  It resisted briefly but gave way with Sadie giving a slight
wince and gasp of discomfort.  Then I began to finger fuck her.  Her arse
felt so hot and tight as my finger slid in and out.  When I felt it start
to relax I added another finger.  This caused a slightly louder gasp and a
more distinct wince of discomfort.  These both became more prominent with
each finger I added until I was jabbing all five in right down to the base
knuckles.

  When the urge to fuck Sadie became too much I stopped fingering her arse.
A look of relief spread across Sadie's face but I knew it was going to be
short lived.  Using the hand I had been fingering her with I greased up my
big fat cock.  After wiping my hand on the sex towel come wank rag I keep
under my bed I got into the push up position above Sadie.  "Are you ready
to lose your virginity?"  I asked as my bulbous knob connected with her
arsehole.  Sadie nodded her head but there was uncertainty in her eyes.
"Please be gentle."  She meekly added.  "Trust me I know what I'm
doing. I've broken in plenty of virgins with my big thick cock."  I said
more to calm her than to boast.  Then I pressed my bulbous knob against her
sphincter.  It really resisted and I had to push hard to break through it.
"Take it out!  Take it out!"  Sadie screamed when the prominent ridge of my
big bulbous knob popped past her virgin tight arsehole.  "Trust me that's
the worst bit.  If I pull out you'll have to go through it again.  I'll
hold still until the pain has gone."  I said to reassure her.  Whether
Sadie believed me or not she didn't protest anymore.  When I felt her tight
little arsehole slacken slightly around my eye wateringly thick cock I
forced a bit more in.  Sadie cried out in overstretched pain and her
arsehole tightened its grip on my cock.  This carried on until a couple
minutes later I had most of my cock buried into her hot wet virgin tight
arse.

  As this was her first time I wasn't going to feed her the full fat 9.5
inches of my cock straight away.  Instead I forced in until my knob tickled
the entrance to her colon.  Then when I felt her arse slacken some more I
started to slowly fuck her to that depth.  Sadie groaned and squirmed at
the stinging burning pain in her overstretched virgin arsehole.  Her body
was tensed and her face was wincing but she had to learn how to be fucked.
Sadie might have been in pain but I was in pure pleasure.  Her virgin
arsehole had such a tight grip on my fat cock that it threatened to cut off
its circulation.  As I slowly thrust in and out her tight sphincter gave my
long thick cock an unbelievable wank job.  My big bulbous knob savoured the
dual pleasure of the hot wet velvety caress of her arse walls on it and my
foreskin fropping over it.

  It took Sadie ten minutes for the pain to begin to ease in her arse.
After about twenty minutes it was boarder line.  It was not until I had
been fucking Sadie for half an hour before her arse began to feel pleasure.
By now her body was limp, her face no longer winced and her cries of pain
were now purrs of pleasure.  It was time to give Sadie all of my cock.
With a hard thrust I buried my fat 9.5 inch cock ball deep into her arse.
My knob forced its way into the even tighter entrance to her colon causing
her to gasp in pain.  "Good girl, you've got all of my big cock in your
pussy now."  I said holding my long fat cock ball deep in her arse to
savour its hot wet virgin tightness soaking into its full length.  When I
felt her arse slacken after being penetrated so deeply I began to slowly
fuck her with the full length of my fat 9.5 inch cock.  Sadie's winces and
groans of pain returned but they were shortly lived this time around.
Within five minutes of full dick fucking her, her moans of pleasure
returned so I started stepping on the gas.  Each deep thrust became faster
and harder until I was fucking Sadie as rough and hard as I would do if
fucking a slutty toilet trader.  When I fuck girls I tend to be a bit more
gentle than when fucking a boy but I got carried away with fucking my first
virgin shemale and gave her everything I had.

  It takes me ages to cum normally but it took even longer that time as I
had had to go slow for so long.  Therefore I ended up fucking Sadie for
almost an hour before I was ready to blow.  Not that I was complaining as
there was so much pleasure to enjoy.  Her virgin tight arsehole was giving
my long fat cock a great wank job.  My knob loved rubbing against the hot
wet walls of her tight arse and slamming into the even tighter entrance to
her colon.  There was the twitch of her cock against my rippling abs.  My
eyes drank in her geekish yet cute face that was flushed pink from taking
her first fuck.  There was the thrill I was breaking in yet another virgin.
Already I had plans to pimp her out to Mark and the bi-sexual girl next
door.  Maybe Samantha knew some shemales she could introduce Sadie to.
Then the pressure in my balls reached critical mass.  However Sadie beat me
to it.  A stunned surprised expression suddenly appeared on his face moment
before I felt her warm cum splattering against our bodies.  Her orgasm made
her arse spasm uncontrollably around my rapidly thrusting cock which set
off my own.  "Oh yeah I'm going to cum."  I moaned as I slammed my cock
ball deep into her arse.  My big bulbous knob slammed into the entrance to
her colon where it swelled as it powerfully blasted out the first bolt of
cum.  Then with short deep hard thrusts I powerfully blasted a further
eleven large bolts of cum into Sadie's arse, taking it last vestiges of
virginity.  It had been fucked and now bred.

  When my orgasm ended I held my cock buried ball deep in her cum
splattered arse to savour my intense orgasmic high and recover from the
vigour of the fucking I had given her.  "You're no longer a virgin."  I
said smiling at her which she returned.  "You have one hot tight pussy that
is great to fuck."  I added.  "Thanks."  Sadie meekly said whilst bashfully
blushing.  Get used to having it fucked as I have some bi-sexual fuck
buddies who'd probably be up for fucking a very feminine teenage
transsexual I thought to myself.  Sadie was so meek and shy she would
probably go along with it as well.

  Once I had recovered from my orgasmic high I pulled my cock from Sadie's
deflowered arse.  Her once tiny pink arsehole was now very swollen, an
angry red and gapping open.  Sadie had received her first ever blow job and
had just been fucked for the first time.  Sadie only had two more cherries
to lose - suck her first cock and fuck for the first time.  We cleaned up
with Wet Wipes and then had a rest.  Soon I was horny again so I rolled
onto my back and pulled my tanned sports toned legs into my chest and out
to the sides so that Sadie could fuck my arse.  I had been fucked by girls
with strap on dildos before so I was looking forward to being fucked by my
first transsexual.  "Time to lose another cherry and fuck me."  I told
Sadie.  "Eat my arse first."  I instructed.  There was a faint glimmer of
disgust on Sadie's face but maybe that was overcome when she remember how
good it felt when I rimmed her.  Sadie buried her face in my bum crack and
gave my arsehole a couple of tentative licks.  When Sadie realised it was
clean save for salty sweat she became more confident in her licks.  Soon
she was lapping away at it as if it was her favourite lollipop.  "Suck and
chew it as well."  I coached after a minute or so of licking.  Fair play
for a beginner Sadie was picking things up quickly.

  After several minutes of an improving rim job I was ready to be fucked.
"Time to fuck me."  I said as I passed Sadie the lube Sadie greased up her
cock and got into the push up position above me.  Sadie then thrust forward
and her slightly slimmer than average 5 inch cock slipped into my slutty
arse with ease.  My arse might have been well used but daily exercise had
kept it tight and able to accommodate any sized cock as if it was a custom
fit.  Sadie gasped with pleasure when the hot wetness of my tight arse
soaked into her cock.  Her cute face had a looked of shocked surprise at
how good it felt.  She had to hold still for fearing of cumming straight
away.  The look of surprise grew when I clamped my arse tighter around her
hot hard throbbing cock.  "Fuck me."  I begged as the cock hunger in my
arse was at its most intense now that my cock and balls had been slatted.
"I might cum."  Sadie apologetically said.  "So cum.  Do what you did when
I sucked you off and keep going."

  Sadie started fucking me slowly with her 5 inch cock.  It was like
looking at a girl whilst being fucked by a boy.  My sphincter was tightly
clamped around the throbbing shaft of Sadie's cock and it burned with
pleasure as she thrust it in and out.  The ridge of her circumcised knob
scraped up and down the hot wet walls of my flexing and squeezing arse.
Despite my orgasm my cock was still hard and dribbled pre-cum every time
her knob hit my prostate.  My tanned hands contrasted with the milky
whiteness of her tiny tits and I groped them.  They were like the breasts
of a girl just starting puberty, being small squishy mounds topped with
puffy pink nipples.  Her geeky yet cute face, whilst looking so innocent,
had an adult expression of sexual pleasure on it.  Sadie was right about
cumming as within five minutes she was squirting her cum into me.  Girlish
whimpers of pleasure escaped her mouth as she spunked up in my arse.  Her
third orgasm of the day felt as copious as the prior two.  "Yeah cum in
me."  I purred as I felt seven jets of cum squirt into my highly receptive
arse.  "Keep fucking me."  I said when I felt her orgasm ended.  Sadie did
as asked and now that she had cum she could fuck faster and harder without
fearing of orgasming.

  The second time around Sadie lasted about fifteen minutes, fucking me for
a total of 20 minutes.  Over the following months Sadie's rarely stimulated
cock would get plenty of action and it quickly lost its hair trigger.
However it was her mouth and arse that would get the lion's share of the
action.  Sadie thought of herself as a girl who just happened to have a
dick and so she liked to pleasure boys rather than get off herself.  She
would go on to suck off many an unsuspecting straight boy and just say she
was on her period if they wanted to fuck her.  Sadie might have started off
a shy virgin but she quickly became a slut who grew in confidence but there
again with me as her teacher it was hardly surprising.

  When her orgasm ended she pulled her spent cock from my arse.  Sadie's
slightly slimmer than average 5 inch cock had made my arse feel good but I
knew I'd have to bugger myself with a dildo when she left to satisfy its
itch.  However the itch in my cock was outweighing the one in my arse.
"Put just your skirt on."  I instructed Sadie and she did as asked.  Then I
got Sadie to get on her hands and knees side on to the full length mirrors
in my wardrobe.  Then I hitched her skirt up to expose her pale arse that
could quite easily have been that of a girl's.  "You can watch yourself
getting fucked."  I said as I knelt behind her.  Her geekish but kind of
cute face had a look of slightly apprehension when she saw my fat tanned
9.5 inch cock approaching her pale arse.  She was right to be apprehensive
as I intended to fuck her with everything I had right from the outset.
There would be no gentle easing in this time.  If Sadie wanted to be a
transsexual girl she needed to learn how to be buggered like a gay boy.
Sadie screamed out and tears came to her eyes when I brutally rammed my fat
9.5 inch cock ball deep into her no longer virgin but still virgin tight
arse.  Giving Sadie no time to recover I launched into brutally hard and
relentless fuck.  Sadie whined in pain and her body tried to back off my
cock but my gip on her hips kept her firmly in place.  Her pale face
suddenly glowed red as she fought the pan in her arse and tears came to her
eyes.

  As I mercilessly fucked Sadie's pussy/arse my gaze wandered all over the
place.  Looking down I watched the long tanned fat shaft of my 9.5 inch
cock rapidly plunging between her milky white skinny buttocks.  Whenever I
pulled backwards I dragged her wildly stretched red sex swollen sphincter
with it.  Then I switched to watching the reflection of our fuck.  Sadie's
upper body had collapsed with her head resting on her forearms on the
floor.  Sadie was looking into the mirror watching herself getting fucked.
Free from her glasses her face didn't look quite so geeky.  The pain my big
fat cock was inflicting on her arse was obvious in her face.  Her eyes were
dripping tears and were red.  She was loudly groaning in discomfort but
didn't ask me to stop.  With her head on the floor this meant her pale arse
was stuck in the air.  My big thick tanned cock was a blur as it merciless
pounded her arse.  Although her skirt was pushed up at the back the front
dangled down hiding her cock so it looked like I was fucking a girl rather
than a transsexual.

  For about fifteen minutes I fucked Sadie with all my might but it became
too much for her inexperienced arse.  Fair play to her though anyone losing
their cherry to a big thick cock would bite the pillow.  Sadie begged me to
stop even though I was a long way off from orgasm so I asked how about if I
went slow and gentle but Sadie said her pussy hurt too much.  Reluctantly I
pulled out of the virgin tight, steamy hot wet confines of her arse.  Sadie
made to get up but I stopped her.  "Stay there I need to cum."  I ordered.
Sadie's upper body went back down so the right side of her face was resting
on her forearms with her pale arse stuck in the air.  Looking down I saw
Sadie's arsehole was bright red, very swollen and gapping open.  Taking my
cock into my left hand I began to furiously wank it.  Even though I had
been fucking for fifteen minutes I still needed to wank for a further ten
before I was ready to cum.  "Take my cum bitch."  I loudly groaned as I
rammed my bulbous knob into her arse.  Feeling her virgin tight sphincter
slip over the prominent ridge of my bulbous knob and then the hot wet
tightness of her arse soak into it fired off my orgasm.  Looking down I
watched my tanned fat cock twitching away as it powerfully squirted jet
after jet of cum into Sadie's arse.  Sadie gasped at the stinging burn when
my knob breached her arse but then as if a soothing balm she quietly moaned
as she felt my cum flood into her very sore arse.  Twelve large ropes of
cum later and my balls were drained and I pulled my bulbous knob from
Sadie's battered arse.  "Good girl."  I breathlessly said as I playful
slapped her right buttock.

  Then I led Sadie to the adjoining bathroom so we could clean up.  Back in
my bedroom Sadie pulled on her white cotton panties before bending down to
pick up her tops.  The lacy material stretched taut over her skinny yet
sexy bum.  It could be that of any teenage girl save for the giveaway orbs
of her balls.  Before Sadie could put her tops on I tried to make a peace
offering from fucking her as if she was a two bit whore rather than a shy
virgin transsexual girl. As I began kissing Sadie I gently backed her up to
the bed and laid her on it as we still kissed.  Then I twisted to Sadie's
left and broke our kiss.  Then my head reached over and began to lick and
nibble Sadie's right nipple as my left hand caressed down her flat stomach
and along her left leg to her knee.  My hand then worked its way back up
and under Sadie's skirt and started rubbing the front of Sadie's panties.
Her small cock was limp but with me rubbing it through her panties as I
nibbled her nipple it didn't stay that way for long.  Soon her slender 5
inch cock was throbbing in her lacy panties and she was cooing with
pleasure.

  For just over five minutes I alternated licking and nibbling each of
Sadie's pink pointy nipples as I rubbed her cock through her lacy panties.
"Stop you're going to make me cum."  Sadie squeaked.  This just made me rub
her cock faster.  "No stooooop." Sadie pleaded too late but I would have
ignored her anyway as I wanted her to cum in her knickers.  Sadie's petite
body began shuddering in the throes of orgasm as she squirted a small load
of warm cum into her panties.  Once her orgasm ended I pulled her cum
soaked knickers off and licked the traces of cum from her cock and groin.
"I need a trophy."  I said smiling at her.  Then I grabbed the boxer briefs
I had been wearing and put them on my cock making sure the crotch was
covering my bulbous knob.  As I wanked I looked at Sadie and made plans to
pimp her out to Mark the following day.  My plan was to turn Sadie from a
shy virgin to as big a cock whore as myself.  Sadie's mouth was still a
virgin so I'd get Mark to fuck Sadie behind the bike shed whilst I had her
suck my cock and give her her first taste of cum.  The thought of that had
me pumping a big load into my boxers and soaking the crotch.

  When my orgasm ended I handed my cum soaked boxers to Sadie.  "Here's
your trophy sexy." I said giving her a smile.  "Thanks but what am I going
to wear home?"  "Your trophy, it'll catch my cum leaking from your pussy
too."  "Eww that'll be sticky."  Sadie said at the thought of pulling on a
boy's pair of cum stained boxers especially as she was so used to wearing
girls knickers.  "Sex is a sticky business so you may as well get used to
it.  Now we'd better get a move on as my parents will be getting back soon.
Sadie put on her training bra, tee shirt and zip up hoody.  Then she looked
at my cum soaked boxers.  "Come on let's put them on."  I said taking them
from her.  Making sure they were the right way around I held them by
Sadie's ankles.  Hesitantly Sadie put first her left and then right ankle
through the leg loops.  Then I pulled them up until they were snugly
cradling her limp cock, small balls and skinny arse.  "Seeing doesn't
feeling my cum against your skin feel good?"  I whispered in her left ear.
"It'll get bigger when my cum leaks from your pussy.  Just imagine when you
get home you'll have a nice big cum stain in your panties to remember me
by."  I said as I rubbed my hand up and down the crotch of her panties.
Sadie giggled like a schoolgirl who'd just hear something rude.  "Do you
want to do it again tomorrow?"  I asked as Sadie pulled up her skirt.  "Yes
please."  She squeaked as if being asked if she wanted to go to the
funfair.  "Cool.  Meet me by the bike sheds after college."  I said.  There
was a reason to met Sadie there and that reason was Mark.  We went
downstairs and I kissed Sadie goodbye.  Once Sadie had gone I returned to
my room and took care of the itch in my arse by brutally buggering myself
with my biggest dildo and squirting out a huge load of cum over me.  Using
my fingers I scraped up my cum and ate it before going for a well earned
shower.

  The following day I met up with Mark and told him about Sadie.  Mark is a
raging bi-sexual who will fuck anything with a pulse but has a particular
liking for MILFs.  He got a sexual kick out of the power he had over older
women and sex starved housewives who would do anything to be fucked by a
virile teenage boy.  He was even fucking one girl and screwing her mother
behind her back.  So it was no surprise that Mark was up for fucking Sadie.
Like me he'd never been with a chick with a dick before and was eager to
have a go.  As for Sadie she was so shy and meek I doubted there would be
any protest.

  When the bell rang to signal the end of college Mark and I went to the
bike sheds to wait for Sadie.  That day she was wearing a black tee shirt,
pink pleated skirt and knee length white stockings.  "Hi Sadie.  This is
Mark."  I said when she approached us.  Sadie said "Hi" back with a puzzled
look on her face.  "He's bi-sexual too and wants to fuck you."  I said in a
matter of fact way.  "I've got a big cock."  Mark said as he blatantly
pulled down the hem of his boxers and tracksuit bottoms to show Sadie his
erect slightly thicker than average 9.5 inch cock.  Sadie blushed and
frantically looked around in case anyone could see us.  There were a few
lingering students but they were behind us and the teacher's common room
was on the other side of the college building.  "So what do you say?"  I
asked.  Sadie seemed uncertain.  "You've only got one cherry left and that
is to suck your first cock.  You could blow me while Mark fucks you, it's
called spit roasting."  I added.  "I can from my own experience its fun
taking cock from both ends."  Mark then chipped in.

  Whether Sadie meekly decided to go through with or actually warmed to the
idea I don't know but she agreed.  It took us slightly more to convince
Sadie to do it behind the bike shed but again she was too shy and lacking
in confidence to put up too much resistance.  Behind the bike shed there
was a gap just large in enough to stand sidewise on to the shed and the
high perimeter brick wall.  The straggling students had left and after
checking no teachers were about the three of us slipped behind the bike
shed with me backing in first.  Sadie then followed me with Mark coming in
last.  "Take off your panties and put them in your bag."  I told Sadie.
Sadie dithered as she decided if she really wanted to go through with this.
She had only lost her virginity the day before yet she was now faced with
not only her first spit roasting but an al fresco one at that and on
college grounds as well.  Mark and I intended to encourage her to max to do
it but if she decided to back out we weren't going to force her.  Again
whether she complied out of meekness or if she did want to go through with
it Sadie pulled off her knickers that were pink and frilly.  Mark already
had his tracksuit bottoms and boxers around and was greasing up his cock.
"Mark's cock isn't as thick as mine so it will go in easier."  I said when
Mark gave me the thumbs up sign to signal he was prepped and ready to go.

  Mark lifted up the hem of Sadie's pink skirt and aimed his cock at her
pale arse.  Sadie gasped and winced in pain but it was nowhere near as bad
as when I cherry popped her the day before.  Mark thrust his cock in ball
deep in one go causing another gasp and wince of pain when his knob slammed
into the entrance to Sadie's colon.  "Wow that is one tight pussy."  Mark
moaned as he savoured the hot wet virgin tightness of Sadie's arse soak
into the full length of his 9.5 inch cock.  Mark didn't hold it there for
long and began fucking Sadie with his trade mark vigour.  For a tall slim
lad he could fuck well above his weight.  He only had one fuck speed and
that was full tilt.  Sadie's geekish but cute face continued to wince with
the discomfort of being roughly fucked by a big cock but she bore it.
Leaning over slightly I watched Mark's cock plunging in and out of Sadie's
milky white arse.  Mark's cock was slightly thicker than average and 9.5
inches long.  It had Sadie's sphincter stretched but not to the extent mine
had done the day before.

  After watching Mark's cock fucking Sadie's arse for a bit I dropped to my
knees and stuck my head up Sadie's skirt.  Her pale circumcised cock was
limp but I soon rectified that.  Sadie's gasp of pleasure when I took her
limp cock into my wet warm mouth turned into a deeply penetrated oomph when
Mark's big cock bottomed out in her arse.  Her arse might have been feeling
discomfort but her cock rapidly grew in my mouth to its full 5 inches.
Once it was hard I pulled my mouth off to admire it.  Her cock looked like
the cock of a 14 or 15 year old boy.  It was slightly slimmer than average
and 5 inches long.  The shaft was pale but got pinker towards the knob
which was circumcised with a small neat scar below a mushroom knob that was
slightly thicker than the shaft.  Her balls were also those of a boy in his
early teens and were encased in a tight pale sack.  Sadie shaved her pubes
but even so they would only have been a small bush anyway.  After admiring
her cute cock I took it back into my mouth and sucked it.  My rapidly
bobbing lush red lips wanked the throbbing shaft of her cock as my tongue
tickled its underside.  When just her swollen knob was in my mouth I
strongly sucked it and swiped it with my tongue.  In no time Sadie's cock
was leaking tasty pre-cum.

  Unfortunately Sadie's cock still had its virgin hair trigger.  For just
over five minutes I sucked Sadie's cock before she started cumming in my
mouth.  Her cock twitched in my mouth as it powerfully blasted out eight
large squirts of thick cum.  Whether it was because Sadie's body had more
girl DNA in it than boy her cum was sweeter and less salty than that of a
teenage boy.  When her orgasm ended I pulled my mouth off her cock and
swilled and savoured her spunk before swallowing.  Then I came out from
under Sadie's skirt to let her have her first taste of cock and cum.  As
usual I was going commando so I just had to push my tracksuit bottoms down
to my knees.  With my left hand I lifted up my deeply tanned fat 9.5 inch
cock.  Then I placed my right hand on Sadie's left shoulder and bent her
forward.  "Go on suck your first cock."  I said when Sadie's face was a
whisker away from it.  Sadie reached out with her right hand and gripped my
cock allowing me to let go.  Sadie seemed mesmerised with the tanned fat
meaty cock in her pale hand.  From the surprised expression on her face it
was as if she was seeing it for the first time.  Not having a foreskin of
her own she seemed fascinated by my tanned foreskin peeling back and forth
over my big bulbous knob.  Then Sadie took her first ever cock into her
mouth.  My cock was so fat she could only suck my knob.  The hot wetness of
her mouth soaked into my sensitive cock head.  She then began to suck it
and swipe it with her tongue.  It was obvious this was the first blow job
she'd ever given but my achingly hard cock didn't seem to care.  The shaft
throbbed like a strobe light.  It leaked pre-cum like a broken tap.  Waves
of pleasure coursed down it straight to my brewing balls.  Despite having
had my obligatory morning wank and then Mark and I fucking each other in
the toilet at lunchtime I knew I had a huge load brewing for Sadie.

  As the spit roast went on my gaze went from one sexy sight to another.
There was Mark's sexy face that was similar to the Staxus and Bel Aim porn
star Mark Zebro.  He had dark brown hair which had dyed blond highlights on
top.  It was twink sexy with pale blemish free skin.  His bluish grey eyes
sparkled with sexual mischief and his kissable pink lips were curled up in
a cheeky grin.  My gaze would then drop to watch his pale slightly thicker
than average 9.5 inch cock rapidly plunging in and out of Sadie's milky
white arse.  Then I would admire Sadie's geeky but kind of cute face
sucking on the end of my big thick cock.  Her face looked so sweet and
innocent yet it was doing something so sexual.  Finally there was the
colour contrast of her small milky white hand wanking my long fat deeply
tanned cock.

  On top of the visual pleasure there were physical and mental ones.  My
achingly hard cock throbbed with the pleasure from the hand job Sadie was
giving it.  My big bulbous knob pulsed from the pleasure of feeling Sadie
strongly suck and lick it.  She was definitely out of the running for the
cock sucker of the year awards but she would turn out to be an eager and
quick learning novice.  The mental pleasures came from the kinky thrill of
having an al fresco spit roast on college property and the fact I was
corrupting a sweet innocent transsexual who had been a virgin the day
before but was now sluttily taking cock at both ends.

  It was Mark who came first out of the pair of us but not until after
pounding Sadie's pussy arse for nigh on thirty minutes.  "Fuck I'm going to
cum."  Mark moaned as he slammed his 9.5 inch cock into Sadie's arse one
last time.  Mark bucked and shuddered as he held Sadie fully impaled on his
long cock.  He loudly grunted as he powerfully blasted twelve ropes of cum
into Sadie's arse.  His twink cute face was a picture of sexual ecstasy and
release as he drained his balls into Sadie.  My mouth and arse had been on
the receiving end of Mark's cock a few times and I knew he came like a
stallion on Viagra.  To play catch up I pulled my cock from Sadie's mouth,
tilted her head up and began furiously wanking my cock.  Within a minute I
was ready to blow.  "Open up her it comes."  I told Sadie.  Sadie opened up
her mouth in time to take a direct hit from my spunk.  A large squirt of
cum went straight into her mouth and coated her tongue.  The remaining
eleven large jets went everywhere.  Milky white ropes of teen boy jizz
landed in her hazel hair, painted out one of the lens of her glasses,
splattered her geeky but cute face and landed in her mouth.  When my
intense and copious orgasm ended Sadie closed her mouth and sampled her
first ever taste of cum as she had never been tempted to taste her own.
Then I used my tongue to steer the cum from her face into her mouth before
kissing her.  Finally I got her to lick my cum off the len of her glasses.
It turned out Sadie liked the taste of cum and became a regular jizz
junkie.  She also confessed to enjoying the spit roast.  We then adjusted
our clothes and left.

   I hope this one got you off and you're sat there splattered in cum.  If
you did please let me know at johnmcquillium@hotmail.co.uk as although I
enjoy reliving it and writing it up it is nice knowing people read it.
Check out my other true encounters in the Sexual Experience folders on the
Gay Adult/Youth, Bi-sexual Adult/Youth, Gay High School and Bi-sexual High
School archives or search for John Mcquilliam under prolific authors