I had been invited to a restaurant by a young man who had
been educated at a very expensive public school and had inherited a position in
a large city bank. He first spotted me at a trans club in Kings Cross, which
was hot and sweaty and dark and full of girls eager to have admirers hands roam
around their bodies and full of men leaving work early and stopping off before
returning to the wife in the suburbs in the hope of getting to screw or fuck
one of the tall sashaying transgirls in mini-dresses constantly parading in and
out of the dark red painted ‘playrooms’ of the club basement.
I had been stalking
around the club like a she-cat, twitchy and skittish and in the mood for some impersonal,
energetic and sweaty, lustful sex. He had collared me after seeing me leaning
over at the bar ordering a coke and leaning over enough, that my dress hem rose
up enough at the back to show the dark lace of my stocking tops against the
smooth flesh of my thighs. He had sidled up to me with an opening chat-up line
that sounded as though it had come from a Beano comic, It made me stare at him
in mild astonishment, while he continually followed me around trying to grope
my bottom and generally get his hand into my knickers.
As a result he managed to scare off various, good-looking,
roaming, potential, horny males, with his persistent chatting and slipping his
arm around my waist and pulling me tight up against his expensive blazer.
He was so insistent that after a couple of hours my
resistance was worn down and I let him have a good feel with my legs slightly
parted, while he stood behind me and rubbed his cock through the flannel
material of his trousers up against the crack between my buttocks. He said that
I was such a beautiful girl and he was so enamoured of me that he wanted to
invite me out to dinner to an expensive little restaurant he knew in town.
Quite why I accepted this invitation I don’t quite know,
although by then I was feeling tired and in need of an escape from his constant
chatter and attention and thought it was the easy way out. He said he was very
rich and would treat me to a wonderful meal and a night out, going clubbing
afterwards and because I am a little bit of a venal vixen at heart ..the
prospect of dating him left images quickly flicking through my mental cinema,
of a rich, not very bright man and possibly some easy sex, which might just
prove to be entertaining and a little sample of the kind of life I’ve always aspired too!
So I accepted his offer and gave him the number to one of my
mobile phones.
A week later as I was getting ready for our date when he
called and said he’d been held up at work and that I should go along alone and
he promised he’d join me shortly. The table was booked in his name, so there
should be no problem. At that point I almost cancelled but something made me
pick up the phone and call my local minicab company to take me into town.
An hour later I was sitting in a very very expensive
restaurant, wearing a short bright red mini-dress, white hold up stockings, red
5 inch heels and a pair of very small dark red lace knickers. I told the
maître’d that I was waiting for my boyfriend and was duly shown to the booked
table. The waiter asked if I’d like anything while I waited, so I ordered
breadsticks, some dipping olive oil and a glass of white wine and sat and
waited while the tables around me buzzed with conversation and the happy chatter
of the other restaurant clientele. Half an hour past and my hooray henry had
still not shown up, I was now begging to feel foolish and more than a little
let down, even in 2016 a women clearly dressed for a date left on her own, at a
table, is the object of slightly sarcastic sympathy. I was feeling more and
more exposed and embarrassed as other diners glanced over at the women in red
sitting alone at a table laid for two, I could almost hear them wandering if I
had been stood up by my prospective date and what might have caused it or was i
just some tart on the make, when suddenly a man appeared at my side and in a
low voice said.
“I noticed you were alone and wondered if you’d care to join
me at my table as I am also alone and it would be nice to have someone to chat
to and have some company while waiting for the food to arrive. I looked up into
a friendly warm and handsome face with twinkling eyes. By this stage I was ‘boiling’
inside with the tawdry way I had been treated by my date so without hesitation accepted
the offer and got up and moved to a table along the side wall of the restaurant
and away from the gaze of the rest of the room. My relief was palpable and I
said
“Would you excuse me a moment I just need to send a text to
my date!”
I texted a suitably rude message, which would leave my
chinless wonder in no doubt as to my opinion of him and his so-called dinner
date.
“Thanks” I said “I’ve been rather badly stood up, so many
thanks for coming to rescue me, it was beginning to get very embarrassing sitting
alone out there in the middle of the room!”
We started chatting and my new friend told me he had worked
in large companies in IT but was now a lone consultant and enjoying the freedom
that brought. The evening passed quickly and we were enjoying each other’s
company and the growing attraction between us. When the meal was finished I
beckoned over the maitre’d and asked whether my date who had stood me up had dined here before.
“absolutely madam, he replied…. he comes here on a regular
basis we have his card details as well to help speed up the payment process” he
smiled at me pointedly “I think madam that perhaps in the circumstances we
should put your meal on his bill for this evening, no?” I smiled and realised he was suggested that
we entered into a little subterfuge, a little plan to help me get my revenge on
the useless twit who had so rudely stood me up. “I shall put your bill for you
and the gentlemen onto Mr woodruff’s standing bill”
“That would be wonderful and appropriate and thank you” I
said
His eyes were twinkling with the conspiracy, which showed
what his general feelings towards Mr Woodruff must have been, as he pulled out
our chairs and we got our coats to leave.
My new date offered me a lift home and after a wonderful
meal of lively talk, I was warming towards my new dining companion and feeling
a warm feeling, a sort of glow, growing in my knickers, so I readily agreed!
We set of after getting in his car and as it was very late I
suggested it would be nice to have a little stroll in the warm evening summer
air before going home. We drove around for a few minutes till we found a parking
space near the Thames. got out and I put my arm through his as we walked and talked
gently along the deserted river embankment. We talked and talked and finally
sat down on a lone bench that looked out across the dark river to the sparkling
lights in the classic buildings on the other bank.
By now I had decided that this ‘new man’ in my life needed a
small reward for saving my evening and rescuing me from embarrassment in the restaurant,
so I reached across and kissed him hard and passionately on the lips. He responded
in return by kissing me firmly, pushing his tongue into my mouth…. and just to
make sure he realised that I was ‘available’ I grabbed his hand and planted it
firmly under my dress on my stocking topped thigh.
He started to feel all around the tops of my thighs and I
yielded to him, gently parting my legs so he could explore further. I waited,
slightly nervous, as to what sort of reaction I would get when he discovered
that I had a little extra in my knickers. I held my breath as his hand inched
nearer the warm lacy centre of my knickers and I felt it freeze for a moment as
he discovered my little ‘extra’, by now quite wet and sticky with pre-cum, but
fate was on my side and I heard him give a slow “MMMMmmmm” of approval and his
fingers encircled my little erection and began fondling me only making me
wetter in the process and making me part my legs even further.
The tempo of our kissing and fondling now went up a step,
having discovered my ‘trans’ status as a sexual partner, he clearly was aroused
by the prospect of having me and his kissing became more urgent and ardent,
spreading down my neck and onto the front of my chest, kissing the top of my
breasts.
I worked my hand into the fly of his trousers, having
managed to pull the zip slowly lower and lower, till I could push my hand into
his tight underpants explore the large and hardening penis. I managed to find a
way to uncoil the stiffening rod and get a couple of inches of the fat head to
poke up out of his trouser fly, then quickly bending over his lap, I opened my
mouth took and sucked as much of his erection as I could, covering the purple veined
skin with my red lipstick in the process and began circling the tip of my tongue
around the underneath of his cock head.
He groaned quietly and just by judging from the various noises
coming from his throat I knew I was having the desired effect and getting him
ready to service me.
As I sucked carefully, making sure that my tongue and warm
mouth was having the maximum effect on the now rampant rod filling my mouth and
wetting the back of my throat with a steady dribbling stream of lubricating pre-cum,
I felt his fingers begin to explore the tight sphincter of my ass.
First one finger, pushing and forcing its way past my tight entrance,
then another finger and finally a third, all squirming and twisting their way
inside me and making me let out little sharp mewling noises even though my
mouth was full of cock.
I was now extremely aroused and could only think of one
thing, and that was that I had to have this large twitching cock buried to the
hilt in my now gaping pussy hole. I sat up and said “don’t move OK!?”
I reached behind me into my handbag, expertly opening it
with one hand and rummaging around till I found the cool metal tube of KY jelly
that I always carried with me for just such occasions as this. I quickly
squirted out a large dollop of lubricant and rubbing with my jelly covered
fingers, quickly covered the upright shaft of his cock. A second dollop was
quickly and efficiently pushed and spread around my ass, my fingers making sure
it was pushed as far into the velvety depth of my hole as possible, preparing
me for his large cock.
I now said “just keep kissing me” and crouched to face him
on the bench, I planted both of my legs either side of his lower body and
holding the upright phallus just under my open wet hole with my hand, my
knicker’s gusset pulled tightly to one side, to give clear access to my waiting
ass. I slowly lowered myself. Manoeuvring with my hand, I positioned the tip of
the fat penis until it was pushed up hard against my small rosebud puckered sphincter.
I then took a few deep breaths and using the weight of my body lowered myself slowly
down onto him and felt the sudden release as his cock pushed through and then
past my tight ass entrance and I felt all my insides compressed and re-arranged
around the sudden intrusion of this large hard piece of male flesh.
He was now in me and judging by the sensations flooding up
from my groin, he was inside me very very deeply. I felt the large penis head
moving and twitching very high up in my belly and for a moment, pressing my
hand against my stomach, I could feel the movement of this swollen fat, invading
male body, deep inside me.
We continued kissing while joined together at the crotch and
I now carefully perched over him to begin a gentle rocking motion, starting a good fucking rhythm of cock thrusts, sending
sparkles of feeling radiating out from my stomach to the rest of my body. There
were now loud slurping noises coming from between us, as his large swollen
penis slammed in and out of my wet hole making a clear sticky noise as it was
slammed back inside me with each upward thrust.
We rocked and bounced, my insides tightening and gripping
his rod in my attempt to milk this glorious cock of its sperm. Finally after a
few minutes of concentrated thrusting and squelching, I felt my orgasm building
and realised that my small cock was dribbling copious amounts of clear fluid onto
the trouser front of my impaling lover.
I could feel his cock begin to swell, getting even harder
and I guessed that he was now very close
to cumming, the same as me. At that exact
moment, seconds before our bodies began to explode with a joint orgasm, another
middle aged couple walked past and seeing us in full, energetic, sexual union…..muttered
disapprovingly about being ‘filthy beasts’ and how disgusting that we were blatantly
and unashamedly having sex in public.
That clearly was a trigger for the both of us, as I felt a
sudden hot wet flood in my belly as the cock I was riding, began to pump a long
stream of frothing, fresh sperm, squirting up me with each thrust, higher and
higher inside my boi-pussy. As I was being filled with his ejaculate, I let out
a stream of muffled yelps that were in unison with his more bass growling and
groaning as he rocked his hips and pushed up with his hips to inject me deeper
with his seed.
My own orgasm erupted in complete synchronicity and I soaked
his already damp trouser completely with my thin girly emissions.
As the last drop of spunk was squeezed into me I semi-fainted
on his lap, leaving both of us breathing as if we had just completed a 100
meter sprint, his hot breath in my ear and my mind focusing on the glorious sensation
now flooding my abdomen as my deeply female persona revelled in the earthiness
and delightful urgent crudity of our shattering, wet, glorious fuck.
Later we recomposed ourselves and our underwear ……and he took
me back to his flat, where we repeated the whole exercise on his large bed,
only this time I gave him the benefit of a little private strip-show, showing
him my sticky wet cum-covered red lingerie and white stockings before having
him take me all over again and deposit another large fresh load of sperm deep
into my hole.
