Storyteller
- 2 years ago
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My Story 2 - Something Different free porn video
This is part two of my story. It's stand-alone and complete but does
make occasional references to the first part - "Taking the Plunge." If
you haven't read that, then I recommend you do so in order to add
proper context to this one. If you don't want to read it then "Nicki"
was the friend who gave me an impromptu makeover at a dinner party and
started the trans fire burning deep inside me. Pete was my former
drinking buddy and the guy who took my female virginity!
Anyway, when you're ready, sit back and enjoy the latest instalment of
my amazing journey from bored guy to fully fledged shemale and, once
again, experience the unrivalled joy of being fucked as only a trans
girl can be!
TC x
----------
One week had passed since I'd felt the ecstasy of Pete erupting deep
inside me. It doesn't sound like a long time, particularly compared to
the several months I'd gone without putting my cock into some
unsuspecting girl who was looking for true love but ended up finding
out after the fact that it was destined to be a one-night stand like
all the others I'd lured into bed.
Don't get me wrong, I loved putting myself about but, in the end, it
was hard to see who was more disappointed - me for failing to excite my
conquests or them for having to endure a cock that promised so much but
delivered so little. And as I thought back to that amazing night of
passion with Pete, I understood their frustration. No, any girl who
had the misfortune to end up between the sheets with me has my unending
gratitude for managing not to look at my diminutive member and say "is
that it?!"
But in realising that there was an alternative to the deeply
uninspiring sex I'd been pursuing in my adult life, I had also come to
realise that the desire to have a cock hard up inside me did come with
some conditions attached. Because deep down, I saw myself as
heterosexual whether as a guy trying to satisfy a girl or as a girl
being rogered senseless by a guy. So it definitely wasn't a case of
going down to the local gay bar in pursuit of some guy that didn't look
like an extra from a Village People music video. Put simply, if I
couldn't desire myself, then the idea of allowing a guy into my most
intimate of places just wasn't on the cards. And whilst I was
increasingly able to focus in on the more feminine aspects of my face,
a flat chested bloke with a small dick was, in my book, anything other
than desirable.
And not only did I want to find myself desirable, any man who wanted to
stand a chance of getting inside my knickers had to find me desirable
too. He had to want the whole me, not just the orifice in which to
unload himself. And whilst my internet sessions had revealed that many
girls ran a mile at the merest mention of tranny chasers - sorry,
admirers - so what if a guy gets off on the idea of shagging a chick
with a dick? That's what I was offering after all! And whilst many
cis-women lament the fact that the best looking guys are married, I
couldn't care less; the advantages of being fucked by a guy who was not
looking for any commitment (and, through having limited sexual
partners, was more likely to be disease free) more than outweighed any
disadvantages as far as I could tell.
So there I was, alone on a Saturday afternoon. Under normal
circumstances I'd have been looking forward to a night out but Pete &
the guys had cut off all contact with me. And the girls had had their
bit of fun with me and whilst Nicki had said that they had no plans for
the evening, I got the distinct impression that it was more a case that
they had tired of the novelty of having a tranny friend and having no
plans that involved me was probably a more accurate description of the
situation.
So if I was going to stand any chance of getting anywhere near a hard
cock, I was on my own.
I googled "trans friendly venues" and it quickly became a apparent that
there was a concentration on the south coast. And let's face it,
wherever there's a trans friendly venue, there will be no end of guys
after a girl with "something special." But it was a 90 mile drive each
way so I'd need somewhere local to sleep, and of course to get laid!
Luckily, plenty of rooms were available so I booked a room in a
nondescript chain hotel where the bored receptionists were bound not to
care about any of the goings on I had planned.
It was then that I realised that I was literally on my own. No one to
give me support or to be my "wingman." No shaggable cis-female to
divert attention away from me or hunky guy to give me protection. I
decided to play it safe as far as travel and check in was concerned; I
picked out some androgynous clothes and decided to leave the wig,
makeup and breast forms off for the time being. I went through Nicki's
bag of things and picked out a shortish dress and packed this, along
with assorted underwear, shoes and accessories to get changed when I
arrived. After having double checked that I had everything, I set off
and just under two hours later, I pulled into the hotel car park and
made my way to reception. Check in was uneventful and I was soon in my
room unpacking.
After a walk around the town and a bite to eat, I returned to my room
to get ready for the evening ahead. It's strange; I was a bag of
nerves as I gathered my outfit together and sat down to apply my makeup
but, as all vestiges of Tony gradually disappeared and Tanya emerged, I
started to feel calmer and by the time I was standing in front of the
mirror admiring myself I was raring to go. I mean what guy can resist
a woman in a dress cut so low that it gives onlookers a full view of
her cleavage, high heels that, combined with the high hemline of her
dress, make her legs look like they go on for ever, loose blond curls
cascading down onto her shoulders and makeup that just seem to scream
that they were well and truly up for it? And up for it, I definitely
was! With a final spray of perfume, I grabbed my coat and handbag and
made my way to the lifts.
The receptionist who'd checked me in was still there as I walked
through the lobby. I clearly looked very different to the last time
she'd seen me and yet there was an air of recognition as she smiled
broadly and wished me an enjoyable evening. Perhaps it was the
legendary female intuition we hear so much about or, more likely, with
the town being so LGBT friendly, she'd seen it all one hundred times
before and could spot the trannies a mile off, even when they checked
in as their usual male selves.
The club was only a short walk from the hotel and as I approached the
door, the bouncer moved the rope and waved me straight in. After
paying my entrance fee and dropping my coat off at the cloakroom, I
made my way up the stairs and into the main club room.
As I walked to the bar, surveying my surroundings as I went, my heart
sank. The fact that the club was trans-friendly was irrefutable -
there were plenty of girls there whose "provenance" was blindingly
obvious from their poorly applied makeup and ill-fitting clothes. And
there were plenty of admirers too, mostly sweaty stressed-looking guys
old enough to be my father in crumpled and stained suits with their
hands in their pockets having, I don't doubt, a good old "fumble" at
the thought of all the trannies in the place. And to think I'd paid
?20 to get in!
Perhaps I'm being a little unfair. There were guys there that
warranted further investigation but they were being surrounded by the
unconvincing trannies like bees round a honeypot so there was no way
I'd get a look in. And the girls who, like me, had made an effort were
just having to fight off the tranny chasers and I was soon in the midst
of the melee too.
"Wanna drink love?" seemed to be the stock chat up line of the chasers
and even after I'd got myself a triple vodka and coke and it was
patently obvious that I would turn their offer down, still the offers
kept coming. And when one particularly persistent individual didn't
take no for an answer and proceeded to put his arm around my shoulders
and tell me his "fascinating" life story, engulfing me with his foul
smelling breath as he did so, I'd just had enough. I downed the
remains of my vodka in one and excused myself to go to the ladies" room
where I sat in one of the stalls for a good five minutes trying to
summon the fortitude to go back to the cattle market.
Nice though the toilets were, at least compared to the rest of the
club, I knew I had to emerge so I went over to the washbasins and,
after drying my hands, started to touch up my lipstick.
At that moment, the door burst open and in flew one of the better-
looking girls who seeing me, exclaimed
"If I have to fight off another tranny chaser who thinks that, because
I've got a dick, I must be gagging to be fucked by him, I swear I'm
going to top myself!"
I took in the sight before me. Facially, she was stunning, makeup
perhaps a little OTT but not out of place against her outfit which was
a metallic silver micro-dress with matching stiletto shoes. Her hair,
which was clearly a wig, was a similar silver colour to her dress &
shoes.
"I know exactly what you mean," I laughed, "the only thing that's
making me gag tonight is smelling their stale breath!"
"At last, a normal person," declared my new friend.
"Well, normalish," I giggled "anyway, I'm Tanya, nice to meet you."
"Ophelia" replied my friend "Ophelia Cockburn" She was very careful to
emphasise each syllable of her surname - Cock-burn - and, as I repeated
her name to myself, I started giggling. Something told me that Ophelia
and I were going to get on just fine.
"So why are you here?" she asked. "There are surely much better places
that a beauty like you could spend her Saturday evening?"
"To be honest, I just want to get laid tonight and this seemed like as
good a place as any. At least before I came in that is!"
Ophelia looked at me with one of those "I'm up to something" type
smirks.
"Come with me" she urged and taking my hand, led me back into the club
and over to a sofa on the far side
"sit here and wait," she commanded before disappearing to the bar and
reappearing with a bottle of champagne in an ice bucket and two
glasses.
"So, tell me what you're looking for"
I thought for a moment.
"To get up close and personal with someone who doesn't make me want to
throw up even thinking about it!"
"Yeesssss," replied Ophelia slowly, moving a little closer to me as she
did so, "and exactly what do you mean by getting up close and
personal?"
This was clearly not the time to hold back in my description.
"To feel their throbbing cock buried deep inside me depositing its
load."
Ophelia laughed and moved a little closer.
"Tell me more," she whispered into my ear. "I'm not sure I understand
exactly what you mean!"
The smirk on her face as she said it indicated that she knew exactly
what I meant. And as I felt her warm breath in my ear, my whole body
started to tingle with excitement. This was clearly a long way away
from my plans to get laid by a guy but here was I being offered
something on a different level - sex with a chick who hopefully still
had her dick - and I would have been mad to walk away.
We looked deep into each other's eyes for just a moment before our lips
touched.
That was it. We were soon kissing with a passion, the like of which I
had never experienced before. Our tongues danced their ritual dance
and soon, my hand had strayed to Ophelia's lap leaving me in no doubt
that, despite appearances to the contrary, she was indeed the proud
owner of the one thing I wanted that evening, a rock-hard cock.
It was a strange feeling, almost a conflict. The guy in me wanted her
because she was drop dead gorgeous and would give most cis-women a run
for their money. The girl in me wanted to feel her cock deep inside me
and I just couldn't figure out which was the dominant feeling. Anyway,
whichever it was, we certainly weren't going to get much further in
that club and were soon on our way back to my hotel room, leaving the
untouched champagne and glasses for any poor soul that felt the need to
get very drunk, very quickly (which, up to around 30 minutes earlier,
accurately described me!).
The sound of our stilettos on the hard floor reverberated around the
hotel lobby, deserted other than the night porter who did a double take
as we walked past.
"Good evening ladies."
Ophelia blew him a kiss as we stepped into the lift. He was quite cute
and it seemed such a shame that we would not be enjoying his company.
I suspect that he would have given his right arm to join us but who
knows what his reaction would have been when he discovered our little
secret? Oh well, I just hope he had a nice wank thinking about a
threesome with us!
But cute though he was, he was soon forgotten. My hands trembled with
excitement as I fumbled with my keycard in the door lock. Finally we
were in and there was no standing on ceremony; Ophelia just pinned me
against the wall, her tongue deep inside my mouth and her hand
vigorously rubbing me down below. She pulled me away from the wall
slightly and I felt her unzip my dress. I followed suit with hers and
we both let them fall to the floor and I was pulled over to the bed.
She let go of me, reached behind herself to undo her bra and then WOW!
She had tits. Real tits. Amazing tits!
"My god," I gasped they're incredible.
"600cc each side - had the surgery last year!" giggled Ophelia with
more than a hint of pride, and who could blame her?
I then looked at my own efforts with more than a little sadness." My
cleavage was convincing enough but the only thing that could lay claim
to being surgical was the tape I'd used to compress the skin on my
chest and removal of my bra would bring the whole illusion, and my
breast forms, crashing down. Ophelia sensed my embarrassment.
"All in good time," she said soothingly, gently running her beautifully
manicured fingers over each of my tiny nipples in turn. "Anyway, we're
not here to compare boob sizes"
And we weren't there to compare dick sizes either but that's exactly
what was about to happen when she saw the diminutive size of mine.
Well that's assuming she wasn't a genetic woman because those tits just
looked to good to be true.
I needn't have worried, about her gender at least, because her panties
were soon on the floor revealing a cock that any guy would have been
proud of. And it quickly became apparent that any hopes I had of
keeping mine hidden were fruitless as Ophelia was soon pulling down my
panties.
"Oh, what a cute clitty," she squealed, taking it in one hand and
gently kissing the tip before cupping her mouth around it and sucking
on it until I was about to cum.
"Not so fast," she laughed, "that was just the appetiser, time for the
main course now."
She quickly applied gel to her cock and, as I let out a sigh of
ecstasy, thrust it purposefully into me, rhythmically working it to and
fro, gradually increasing the pace until I felt it starting to pulsate.
She grabbed hold of my still rock hard dick and with a couple more
thrusts, we came simultaneously, her warm cum spurting inside me whilst
mine shot up like a fountain over both of us.
And as her erection finally died down and she withdrew, she moved down
and licked every last drop of my cum from my body before we finally lay
together on the bed, holding each other tight.
And as I lay there, the realisation set in. I'd been fucked by a
shemale and it was the best shag I'd ever had by a large margin.
Getting laid by Pete had been amazing but this was just on another
level. And we'd only just started!
Soon, our cocks were letting us know that they were ready for more. I
couldn't wait to feel Ophelia's deep inside me again but she had other
ideas. She lifted her legs to reveal her "pussy" and whispered, "Your
turn."
Now, apart from the fact that my dick is, shall we say, a little on the
small side, my sole aim that evening was to feel a cock inside me as
many times as possible. The thought that I would be expected to take
the sexual lead had not entered my mind. It's not that I had anything
against the physical side of it but just that emotionally, I wanted to
play the female role.
But as I felt Ophelia rubbing gel onto my dick, I knew that I was
either going to have to go along with it or call a halt to the evening.
And, as I looked at her lying there, every inch the gorgeous female
that, as Tony, I would have shagged at the drop of a hat. The decision
was a no brainer so in went my "cute clitty!"
Never having had sex in this way before, I'm not sure what I was
expecting but it just felt completely normal and, as I got into a
rhythm, there was no stopping me. And while all of this was going on,
Ophelia's cock was standing proud as we both cupped our hands around it
and caressed it.
And then the tingling started, my thrusts became faster and more
vigorous as I tried to hold off cumming for as long as I could. But
then, as a tingling sensation engulfed my whole body, I could hold it
in no more and my throbbing dick erupted inside her. And a few seconds
later, Ophelia came too, erupting like a volcano while her cock
pulsated in my hand.
And as I returned her earlier favour and licked her clean, it hit me.
I'd actually made her climax which is more than I'd ever achieved as
Tony with any of my female partners although some had made a half-
hearted attempt at faking it. OK, I know that the more bigoted members
of society would contest the female thing but believe me, as I saw her
lying there, looking as beautiful as any other woman I'd ever seen and
with those mountainous breasts pointing skywards, I would challenge any
of those bigots to resist her charms.
We fucked each other twice more that night before we finally admitted
defeat and fell asleep in each other's arms.
I was woken the next morning by a gentle kiss on my lips, its
tenderness nothing like the raw passion of the night before but no less
sensual even so. And now, devoid of makeup and her long brown hair
freed from the contraints of the wig she'd been wearing the night
before, Ophelia looked different. The sexy siren had gone, and in her
place was the cutest girl that any lucky guy would have been only too
happy to take home to meet his parents.
But the truth was, I felt a fraud. Nothing about me felt genuine - my
hair and tits were fake and strip away all of the feminine accessories
and I was just plain Tony, a guy with a weird wish to live a female
life because it seemed like fun. With Ophelia, there seemed to be no
fakery, what you saw is what you got. She sensed that I was a long way
away.
"What's the matter?"
"I'm sorry," I started. "I feel like such a fake compared to you.
You're the real deal and I'm just, well you know."
"I know," she said tenderly, "but we all have to start somewhere.
There was a time when I was just like you and with all the insecurities
that go with it but, bit by bit, I dealt with them either by realising
that my worries were groundless or, as with the boobs, making changes
towards becoming the person I wanted to be. I could argue that my
boobs are just as fake as yours and the only real difference between us
is that I no longer care!"
"But Ophelia," I started before she interrupted me.
"And that's my biggest act of fakery - my name! It would take someone
far braver than me to go through life being called Ophelia with a
surname of Cock-burn! I'm afraid that in daily life, I'm just plain
old Penelope, or Penny to my friends. My surname is my real one but
it's pronounced Co-burn!"
And as I looked at her, somehow Penny "Co-burn" seemed to be a far more
suitable name for her than the contrived drag-queen moniker she'd given
herself the night before. Penny continued.
"And look at last night, my fakery was in overdrive. Like any other
girl, I like to have fun and even get a little outrageous but that's
not the normal me. I'd need to be a sex worker to live like that all
of the time."
I thought for a moment and started to fear that I too was part of her
fakery.
"So was the sex fake?"
"Absolutely not. I was turned on as soon as I saw you fixing your
lipstick in the mirror. You looked hotter than most of the clientele
and you probably sensed my determination to get you into bed. I can
fake a lot of things but not my reaction to someone I'm desperate to
have sex with."
"But why me? I'm sure that someone like you could have the pick of any
guy or trans girl she wants."
"Why not you?" she answered. "OK so you're wearing a wig and your tits
are fake but real women spend a lifetime faking it. Even the most
beautiful models don't look that polished all the time."
And as I thought for a moment, I realised that she was right. But
there was one more thing that was puzzling me.
"Please feel free not to answer this if you don't want to but, as a
woman, why were you so keen to take the male role last night?"
Wouldn't you just prefer to lie there and let some hot guy do all the
work?
Penny laughed.
"I do it because I can! Imagine all those guys who'll never experience
the sheer pleasure of feeling a hard cock thrusting deep inside them.
Or the women who'll never experience what it feels like to slide into a
warm pussy. We special girls have the best of both worlds and I was
just as happy in your pussy as I was feeling you in mine."
I couldn't fault her logic and the truth was that I wanted her more
than ever. And as we lay together, it soon became apparent that she
was ready for more and, as I saw her reach for the tube of lubricating
gel, I tingled with excitement.
Life was just getting better by the minute!
----------
Epilogue
Finally it was time for us to go our separate ways. Luckily, I'd
arrived in casual clothes but Penny had nothing to change into so just
put her clubbing clothes back on and fixed her makeup. As we made our
way across the lobby, the night porter was just finishing his shift but
turned and walked back when he saw us coming. He was probably in his
mid 20s and, it has to be said, very good looking. He smiled as he saw
Penny looking just as gorgeous as she'd been the night before
completely oblivious to me as I handed back my room key.
"Err, I was wondering whether I could perhaps take you to dinner
sometime. I've not been able to stop thinking about you since I saw
you last night"
Penny looked at me then smiled at him. He looked flustered.
"Oh, I'm sorry," he stuttered, "I understand."
Penny laughed and then in her male voice which was quite a bit lower
than the feminine tones she usually used when talking replied.
"Oh, that sounds wonderful and I'm sure Tanya would like to join us too
wouldn't you."
"Ooooo yes, thresomes are such fun!" I replied in an equally deep
voice.
"Here's my number, call me!" said Penny handing the porter a piece of
paper before we both left the hotel to walk to my car. As we passed
through the doors, I looked back to see him, still in shock, starting
at the paper in shocked disbelief at what had just happened.
"Poor thing" laughed Penny, her voice back to its more feminine timbre
"he'll never be the same again. I doubt he'll call but if he doesn't,
he'll never know what he he's missing!"
"Can I drop you off anywhere?" I asked as we arrived by my car.
"Oh, don't worry, I only live a few minutes' walk away," she replied.
"Please call me," I urged as I handed her a piece of paper with my
number hastily written on it.
Penny just looked at the paper and smiled before wishing me a safe
journey and giving me a gentle peck on the cheek. And then she turned
and was on her way with just a final wave as she disappeared round the
corner.
As I drove back home, I tried to imagine Penny's lifestyle. Weekends
out at tranny clubs with the sole aim of getting fucked (and looking
like her, she'd be able to pick whoever she wanted and they'd be
powerless to refuse) and weekdays spent just being a normal girl,
perhaps smartly dressed for the office and blending in completely. How
I so badly wanted that lifestyle for myself.
But my mid was spinning. I thought back again to my feelings when I
was with her and how she said that she had the best of both worlds.
I'd never have thought that I would experience the conflicting
viewpoints of my male side wanting to fuck her senseless and my female
side wanting to be like her but that was exactly how I'd felt.
I'd had one night stands before and by lunchtime the following day, had
practically forgotten the name of the poor unfortunate I'd shagged.
But Penny was different; she was everything both male me and female me
could ever wish for in a partner. I kicked myself for letting her go
without at least getting the means to contact her again but that was
now the reality - I had to wait for her to contact me but there was
something about her reaction when I gave her my phone number that just
seemed to suggest that I was going to have a very long wait.
Life as a shemale was supposed to be the making of me and yet it was
just leaving me feeling wretched. I'd been fucked by two people - each
time the greatest sex I'd ever had - but now it just felt like I'd been
fucked up by them. I could cope without Pete, after all he was just a
bloke with a large cock and there'd be plenty more of those but Penny
was something special and I'd just let her slip through my fingers
without putting up a fight.
And that was the moment that I crumbled. I pulled into the side of the
road with tears streaming down my face, the feeling of rejection far
more intense than anything I'd ever experienced before. And as I sat
there sobbing, I knew that if I was going to get anywhere in the new
life I'd planned for myself, I was going to have to toughen up
considerably.
At that moment, though, it just seemed like an impossible task against
the knowledge that I had fallen head over heels in love. How would I
ever get over Penny?
Annalisa
- 17.09.2021
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