Date: Sat, 14 Jul 2007 22:09:56 +0100
From: Karen Blush <kareninshortskirts@hotmail.co.uk>
Subject: Karen's First Date (transgendered story)

The following is (sadly) fictional.  Hoping it won't be for too long.


I finished work early in Thursday.  It had been an early start but I wasn't
tired, I was far too excited to be tired.  I got back to my flat and started
running a bath, stripping off my work clothes and leaving them strewn on the
floor wherever they fell.  I had to get ready, I was going on a date.  For
the first time in my life I was going to let someone else see me dressed as
a girl, as Karen.

I'd always dressed up, I don't even remember when I started.  I began
borrowing my mum's clothes, later aquiring some of my own and from time to
time I would have a fair stash of underwear, skirts and tops, until I went
through another 'purge' and decided I wouldn't do it again.  With me it was
always sexual.  I dressed because I found it a turn on, and I loved to
fantasise about sex with a man (or several).  Actually all my fantasies are
about that.  Now I was finally going to meet a guy and show my hidden self.

The bath filled, I washed and shaved myself and set out my clothes for the
date.  I'm not subtle when it comes to dressing, I'd already chosen the
'slutty whore' look and anyway, it was pretty much all I had.  The basque
went on first, tight to help shape my waist.  I don't have a natural 'girly'
look, I'm not really passable but I like to try my best.  The stockings slid
up my legs and the straining hard on I'd had for the last hour quivered as I
began to anticipate the night ahead.  I fixed my makeup (bright red lips,
too much blusher) and threw some jeans and a jumper over my underwear.  I
needed to drive to Mike's house and finish getting ready there.

Sitting outside the house I tried to summon the courage to get out of the
car.  My heart pounding, legs like jelly I made it over to the door and rang
the bell.  I was nervous as hell.  Mike opened the door.  "Hi, come on in"
He looked just like the picture he'd sent (fortunately).  Late forties, nice
if plain looking, reasonable shape if a tad 'spread out' round the middle.
Perfect.  I hated this bit, I was here to be Karen.  "Can I run up andget
changed?" I asked, wanting to get out of the jeans so badly.  Mike directed
me up to a spare room and said he'd be waiting downstairs when I was ready.

Upstairs the rest of the clothes came out - leather mini skirt, red silky
top.  3" heels.  Brown shoulder length wig tied back in pony tail.  I sat as
Karen on the end of the bed.  "well, this is it then" I told myself.  Slowly
on heels I wasn't used to wearing I walked down to start my date.

Mike was sat on the sofa as I walked in, flicking through a magazine.  I
took in the scene and noticed it was a Transvestite porn mag, hardcore by
the look of it.  He saw me looking and put it down, embarrassed.  We'd
agreed to meet and talk, get to know each other.  He knew I was
inexperienced and wanted to go slow.  He started to apologise but I laughed
and said it was OK.  Actually, I found it quite exciting.

We talked alot, got on really well, I was starting to feel pretty
comfortable.  He didn't try to force me, never suggested we do anything, it
just happened that way.  We'd been talking and there was one of those
silences you get sometimes.  I reached over and picked up the magazine.  He
looked at me as I opened a page at random.  There was a couple on the bed,
he was naked, lying on his back.  She (well, the tranny) was draped over
him.  Cock in her mouth, hand round the shaft, looking right at the camera.
"You like this magazine?" I asked cheekily.  Pretty obviuosly he did.  He
stared right at me and made me feel weak in the knees. Finally he said "Yes,
very much.  Do you?".  I looked again at the  picture, understood what he
was saying and found I could hardly speak.  My voice was quiet and hoarse as
I looked away from him.  "Yes" was all I could manage.

He stood and took my hand, leading me out of the room and up the stairs.  We
went into his bedroom together and I stood by the bed, not knowing what to
do.  I felt clumsy, awkward.  He adjusted the lights, fished some things out
of a drwawer and came up behind me.  I felt him kiss my neck, felt the hard
presence of his cock push into my bum, felt myself push back and grind into
it, loving how it felt and how it made me feel. He moved to the bed and lay
down in the middle, motioning for me to join him.  Lying by his side we
rolled toward each other and he kissed my mouth, it was odd, being led,
feeling him probe me, feeling his stubble.  His hand traced my back and
began to grope my bum, then lower and I felt him slide it up under my skirt,
causing me to catch my breath.  Damn I felt so bloody horny.  I knew what I
wanted to do now and reached one hand down to his flies, rubbing my hand
over his bulging crotch.  He stiffened his body, pushed into me as I rubbed
him through his trousers. In no time I had the zip down, fumbled for the
button and we both laughed as he had to roll onto his back to let me use
both hands.  Having got the trousers undone, I sat up to my knees and pulled
them down and off.  I was kneeling on the bed, my hand slipped into his
boxer shorts and grasped his cock.  The first cock I'd ever held apart from
my own. His eyes were closed, one hand over his face as he moaned "Mmmm,
that feels good". I withdrew my hand and drew down his underwear, returning
my hand to his hard dick.  I thought of the magazine, the girl leaning over
her man and positioned myself so I was resting on his stomach, leaning on
one elbow, the other hand stroking his cock.  I looked at it, felt its
hardness and warmth in my hand.  As I continued to stoke I felt his hand run
behind my head.  He didn't push, but the intent was clear - suck it.

I'd never given a blowjob although I've received many.  I know what to do,
maybe not for the best ever bj but enough.  I bent my head and began to lick
the tip.  It tasted a little like my own pre-cum (yes, I had tried it) but
also different.  A faint smell of muskiness and sweat greeted me as I pursed
my lips and gave a big sloppy kiss to the end of his cock.  He twitched, his
dick jerked in my hand.  I pulled back, held up his cock and licked along
the shaft.  I know that feels good but I could tell he just wanted it in my
mouth, so I came back up and slid the whole end right in, taking about half
his cock in my mouth.  Next I drew back up, swirling my tongue over the tip
as it reached my lips.  His hands began searching again, I felt them move
down to my bum and again got the thrill as they slipped under my skirt.  I
felt his fingers trace up my legs, running up to the top and my black silky
knickers.  He pulled back the elastic and a finger slipped in.  I moaned as
I felt it, moved myself to allow my legs to part slightly and felt him probe
for my hole.  Suddenly he stopped, pulled me off him and rolled over the
bed.  Confused I was about to ask what was going on until I saw him squirt
Lube onto his hand. "Trust me", he said.  I did.

we resumed our positions, me with his cock in my mouth, him with his hand in
my knickers.  I felt his finger return, this time it was wet.  It moved
purposefully to my hole and straight inside.  I nearly choked on his cock
but after the initial shock the feeling of being fingered whiile I sucked
him off was very, very horny.  My bum wiggled on his finger, he responded by
thrusting into my mouth. Again he stopped and drew me off him.  "If you
carry on like that I'm going to cum" he told me.  Quietly, nervously and
longingly i replied "sounds ok to me. Just one request"  "Whatever you want"
he said, keen to get back in me now he knew where it was going. "As it's my
first one, would you tell me when you're going to cum?"  He laughed, told me
I'd know, but yes, he would.

I took him back in my mouth, sucked faster now bobbing my head on his cock,
wanting to taste my first cum.  I didn't have to wait long.  He began to
writhe on the bed, force his finger deeper and harder into me.  I felt him
tense, his free hand holding my head in place and heard him cry "uuuuuhhh
I'm cuming!".  About a second later I felt the twitch as he started to shoot
into my mouth, felt the sticky hot cum pump into me  and tried not to gag.
A second, a third shot, my mouth full I began to dribble his cum feeling it
drip down my chin.  The twitching subsided.  I took his shrinking cock out
and swallowed down his hot spunk.  It tasted strong, spicy.  Odd.

I looked at Mike and he smiled at me. "How was your first blowjob then
Karen?" Just hearing those words made my buzz with excitement.  I felt hot,
wanton, sexy.  I wanted more.  "Nice. But now we have a problem" I told him.
  "What's the problem Karen?".  I smiled at him. "Well you see, I'm now so
incredibly horny having scucked your cock like a whore, that I'd really like
you to fuck me.  Problem is, you look a bit....soft?"

What happened next?  Want me to continue?

kareninshortskirts@hotmail.co.uk