Date: Thu, 21 Aug 2014 21:34:40 +0100
From: Vincent Fairclough <vincentf921@gmail.com>
Subject: Roxanne TS

Roxanne

It was a normal Saturday night apart from the fact that the world cup was
on and England where playing their opening match against Italy. I had
visions of most of the pubs being very busy for the 10 o'clock
kick-off. Now I have nothing against football but I am not a fan, my
parents where never into it and my friends often only passive
supporters. Being brought up in the north-west of England meant that there
was intense rivalry between Liverpool, Everton, Manchester United and of
Course Manchester City. I lived right in the middle of them, it wasn't any
better if you where a rugby fan, St Helens, Warrington, Widnes. I enjoyed
playing football, but I wasn't good at it, I was very small and my exposure
to sports at primary school was further disillusioned when one year someone
licked the football to me at full throttle, I froze and subsequently felt
myself lifted off the ground as the hard casey ball smacked me straight in
the stomach knocking the breath right out of me and leaving me in a
helpless bundle on the floor, much to the amusement of the other players.

So yeah, macho male pursuits where not my thing and I went out of my way to
avoid them for the duration of school life , I managed to fall in with a
couple of other wimps who also did not excel at sports either and after a
humiliating try for the sports day resulting in my failures being entered
categorically into my school report, finally they stopped trying. I left
school being barely 5 ft tall and weighing less than the insulting 7st
required to officially be a weakling, entering puberty late around age 15
was just the next insult as other boys laughed at my pathetic none-hairy
manhood or rather boyhood. Luckily a few years later I found a girl who
liked me for who I was and we married and had three lovely sons

So back to the present I was delighted that the Watchmakers' was not
totally packed and most of the footy fans where gathered at one end by the
biggest screen. This meant I could watch the match at a comfortable
distance from the tribal ritual shouts and whoops as goals where either
scored or allowed past the defences. As I got my second drink in I
manoeuvred closer to the entrance where I could both observe ladies
entering and introduce myself to any potential dates, or just chat to pass
the evening away. It was then that I somehow found myself talking to a
young Singapore gentleman, he had only entered the country a few weeks
before and as I asked him what he was studying I realised that I was
transfixed and I actually wasn't listening to a word he was saying. It is
not that he wasn't interesting, but as I moved closer to hear him over the
football chants and groans and my eye contact got more intense I realised
that I fancied him like mad. His skin was a lovely shade of light brown,
his eyes dark and mysterious, his skin soft and girlish. I had often been
attracted to Asian and Oriental women and he was having exactly the same
effect on me.

I was so entranced at trying to keep him talking that without thinking I
told him how beautiful he was. Sadly he did turn a shade or two redder and
made his excuses and left. Now as much as I am seeking a new life partner
of the female persuasion my urges are not limited to that direction only,
but they do vary from time to time, I do not consider myself so much
bisexual as flexual, I am capable of being attracted to either sex, but as
to how much on a given day or week, well it depends but I do not know what
on. So I decided to find myself a nice cock to play with and made for the
Queens Arms, a local gay friendly pub, I say gay friendly because these
days there are many straight people usually male/female couples or
couple/groups of girls who enjoy them as well as many single guys who want
to see what life is like on the other side of sexuality.

Recently refurbished and its sister night club closed after many years of
struggling, the Queens' was nicely busy and I bumped into a couple of
friends who where saddened to tell me that a mutual friend had recently
died and they where waiting for the post mortem. I glance around to see if
I was getting any male attention or if there where any guys in that I might
like to approach. But there was only a pretty lady sat on her own in the
corner that I usually occupied. Pretty, for sure. A second glance caught
her eye and I leaned forward as if that would help me to see clearer, she
made a quick glance at me then turned away shyly which I read to say she
liked what she saw. It must have worked because for the second time that
night my autopilot kicked in and I stood up and excused myself from my
friends in mid sentence. As I stood up I realised that this pretty lady,
some years younger than me and slightly large build, was indeed a very
attractive transsexual.

I went over and said, 'Hey, how are you?', with a smile. I am not into
cheesy chat up lines. I must mention here that two weeks previously I had
missed out on starting a conversation with a much younger blonde tranny in
the Watchmakers, I was not going to make that mistake tonight. I soon
discovered her name was Roxanne and she was quite demure but
confident. Later I would discover she was quite tall, certainly six foot in
her heels, she had quite long brunette straight hair and her eyes where so
delicately made up that at first I wondered if she had much make up on at
all, her lips where a pinky red that made her look classy. Her face was
round and very beautiful. I know a lot of trannies think that more make up
is more feminine. She had a cream dress on and she perfume was subtle and
delicate. I genuinely found it hard to believe I was not talking to a woman
until she put her hands on the table and as I asked what she did for a
living, she answered that worked in a recycling plant, her hands where
bigger than mine, OK mine are girly but these hands where workers hands but
her nails where decorated perfectly. She said she hated her job especially
as it was a traditional male job and she could not be herself at work for
fear of ridicule and stigma.

I went to touch her her to let her know that I knew how she felt as I have
a feminine side that I suppressed for many years, 'No, she said. My
girlfriend is at the bar. She will get so jealous'. I pulled back and and
the look in both our eyes said that we wanted to take the conversation
further another time. So I went to the gents and wondered if she would take
the hint and meet me at the other end of the pub. She did not so I went
outside and chilled in the cool evening air for a while and checked out who
else was around. When I went back inside Roxanne was just about to enter
the ladies, that's when I realised how tall this Amazonian beauty was, I
had already prepared a paper tissue with my mobile number and email address
and passed it to her. I had another large vodka and tonic and wondered if
she would contact me, I fell asleep thinking sexual thoughts of her of
course and realised I had fallen asleep on the sofa and it was four am,
there was a full mug of cold coffee and a half eaten chocolate biscuit in
front of me, I dragged myself to bed.

I did not get up until after eleven the next morning and I had left my
mobile on the living room table. I was amazed to find a missed call from a
number I did not recognise from about 5 minutes earlier, I must have just
got into the shower then. I debated if it was safe to call back as it was a
landline number. I called and Roxanne answered and asked would I like to
see her that evening in the Queens'. Of course I said yes and Sunday night
is tranny night in the Queens' so she would be right at home there. I
thanked myself for making the effort to overcome the anxiety that had
plagued me for so much of my life and congratulated myself for making a
move, what would she turn out to be like when we could talk comfortably
together.

I could not wait to meet her that evening, I found another decent shirt and
trousers so I would look different and had another shower and shave to look
and smell my best. I strutted confidently though town to the Queens' and as
soon as I went through the door she was sat there looking even more radiant
than last night. I went over to her and got us drinks, she drank cider, me
lager as they don't do decent bitter there (why do gay pubs never have
decent beer or music?). As I sat down I felt her hand on mine and I turned
to face her and we kissed full on the lips. Now I have kissed men before
and some are really good kissers, but this lady was as good as my ex-wife,
gentle and caressing my face and unusually it was me who pulled away
first. 'That was what I dreamt it would be like darling', I gasped.

Now I fully understand that people want to embrace their gender and
sexuality fully, I should because mine is complicated enough, but often
some trannies will be offended if you enquire into it. For me Roxanne was
made even more desirable because she was a transsexual or third gender,
like there are only three, I mean if you research and understand the
subject there are many variations as there are in people generally. I was
pleased that Roxanne was happy to explain her journey, she had always known
that she was mostly female inside, and that she was fully aware that her
large build might compromise her looks, she said she had been on hormones
for three years and her breasts where as big as they would develop as she
was 36 and ideally they need to be taken before puberty around 13 to allow
puberty to happen as a female. This is illegal in this and many other
countries which is a problem as if you wait till you are 18 the effect of
hormones is much reduced.

I acknowledged that as it was she could hide her breasts at work but if she
wanted to have augmentation she would have to change jobs to one that was
more sympathetic. I told her I would love to employ her if I could as I am
starting a business and could train her and she would not need to meet
clients till she felt ready. I also quickly injected into the conversation
that I am a fem-guy, that is one who has several female traits even if they
are not obvious as some trannies like to have masculine partners (even when
they are females) to compliment their femininity. Having seen her
girlfriend I thought this might be the case as she looked to be a butch
lesbian. Now you are probably thinking why would a butch lesbian want to be
with a tranny, but that's how it works for some, transsexuals can be
attracted to any flavour of gender just as straight men and women can.

I eventually plucked up courage to ask her if she was pre-op and if she was
planning on keeping it, as only around one in five decides to have a
vagina. My own point of view is that they should legally be allowed to
become female if they live a female lifestyle regardless of what is between
their legs. A small percentage of the population has suffered with CAH
growing up and has both genitals at birth, they are assessed an designated
their gender before puberty, which let's be honest is way too early for
them to make an informed decision as they are often stigmatised for having
both genitalia or being in the wrong gender role at school. Roxanne told me
she was going to college and increasing her basic skills so she could
broaden her career options and decide how far to take things as she could
barely afford breast augmentation let alone a full sex change if she
decided it was appropriate.

She told me that her girlfriend was getting quite possessive, but
originally she had said that she wanted an open relationship as she was
attracted to both sexes, but favoured men for a long term relationship. I
explained that I was bisexual too and that I favoured relationships with
women and that included transsexual females in that. Then she grabbed my
hand and said 'let's go outside I need some fresh air!'. She could
certainly walk fast even in four inch heels, I thought she meant she was
desperate for a cigarette but I had not seen her smoking. We went into the
smoking area outside and found a corner and she through her arms around me
as we stood with her towering over me, I am only 5'8 and she's 6'2 in
heels, she kissed me and pulled me close to her. I managed to control my
hands and keep them round her waist, well mostly, her body did have womanly
curves and her bum flared out below her waist and damn I was getting a
hardon and she was pulling me close to her so she could feel it.

My head was spinning and I felt that hers where too, she gently rocked in
my arms and she kept sliding to one side of me, so I pulled her to face me
and then I realised why. She had a big fucking hardon too! And I felt hers
was even bigger than mine. 'I hope there is plenty of room for that in your
knickers baby', I laughed between her kisses and at that moment I was
falling in love with this lady. We kissed and cuddled for about 20 minutes
and eventually sat down and got more drinks in. Roxanne asked if she could
discuss previous relationships as she felt this was starting off
differently. I told her I was open to all sorts of relationships and not
the jealous type, so yes it was fine if I could discuss things with her
too. She explained that she had a relationship with a guy she worked with
when she was still fully male (is that possible) or at least in the male
role, and he had got more and more possessive and jealous as she
transitioned to be more female, he had then threatened her with exposure at
work. As hard as the job was she felt comfortable in it as she could work
lots of overtime to save for augmentation and clothes as she was running
two wardrobes. Roxanne said she was still discovering herself in this role
and wanted to experiment sexually but would love to have a partner to share
this with when he came home. I told her that when I was married we had
started meeting other couples and occasionally single males and females
both separately and together, so I could handle that. She replied that if
we could do that together it would be a lot more fun as she still enjoyed
sex with women and a lot of women saw it as a step to having females, as
some men saw it as a step to having males while looking into a female face
and familiar dress.

I was quite surprised when she said, 'are you as gentle in bed as you are
when you are kissing me?'. I was worried that she needed someone more
assertive, 'Well yes I am, but I can be more physical if you want me
to'. She said she loved me being gentle as most men had been too rough with
her, I told her that most women where not even as gentle as her and I loved
her touch and wanted to make love to her slowly and completely. She drank
up and said, 'Well we had better get started then hadn't we?' and stood up
with her hands on her sexy hips. We got a taxi to my place and I put the
kettle on and drew the curtains in the living room and bedroom so we could
have the run of the house as we progressed. While the kettle was still
building up to a boil so was I so I went over to Roxanne and kissed her
deeply taking same of the control from her, I felt her begin to relax. I
ran my hands over her breasts through her dress and I could feel that
beneath the bra some of it was breast and some was padding. 'How do you
feel about them being padded?', she shyly asked. This was the first time
she had shown weakness. I told her that she had breasts and whatever she
had I would be perfectly delighted with. She admitted she was nervous about
getting naked, so I told her we would take it slow and she could get
comfortable at her speed. She kissed me again and as I squeezed her breast
she ran her hand over my crotch and grinned, 'See you are not the only one
who is small!', I giggled.  'I want it baby!, she replied as I broke away
to make the drinks as I wanted to take the edge off the alcohol, I like to
be fully in control of my senses with a partner.

We sipped coffee and said what we liked about each other physically, I told
her that I genuinely believed she was a woman at first. She had relaxed
quite a bit and started to undress me down to my undies and I was not
allowed to undress her till I was in my briefs. Each piece of clothing that
came off was accompanied by kissing and touching my chest, arms and
legs. Then she teased my cock and balls through my briefs for a minute or
two, then she said 'OK your turn'. Now I knew she was wearing stockings but
hadn't really wondered too much about what else she had on so this was
going to be a surprise. I undid her dress and eased it off, she had on a
bright purple bra probably only an 'a' cup and purple panties, now I prefer
less revealing panties than the skimpy ones young girls wear and hers where
lacy see through, and her cock stood up above the gusset and was big and
thick. She also wore a black suspender belt and her stocking where lacy
patterned which I had not noticed, those are my favourite! We kissed and my
hands where all over her back and arse then we broke the kiss and I undid
her bra. I felt her tense up as it fell away and each cup had cotton wool
padding in, as I dragged it down over her breasts exposing them, they where
small but shapely, slightly pointy with quite large areolas. 'Wow they are
lovely!', her face lit up as she looked into my eyes to see if I was
kidding her. I took each one in my mouth and sucked on it as my fingers
explored her thighs and panties then of course that thick cock which was
really throbbing and about 7 inches long, shaved and uncut, just how I like
them.

Looking at her in just her panties the image that presented was truly
something special, her hips where curvy, her legs so feminine and
delicious, her eyes so soft and sensual, it was really a woman, a woman
with a big hard cock waiting for me! I lead her to the bedroom having left
my hi-fi on to cover the noise because I live in a block of flats.  We lay
on top of the bed sheets and I teased her panties down to expose the head
of her cock, then I turned around and licked the shaft though the panties
making them wet. Then I took the end in my mouth and felt her push me onto
my back and sink my cock into her mouth in one go. I pulled her panties
down and did the same to her, fuck she tasted good, really good. I slapped
her arse and she loved it. Her fingers started to explore my balls which
are shaven like my cock, then her fingertip went right between my legs and
she squealed. I gasped as she had just found that my arse is shaven smooth
too, 'I love your bum baby!', she giggled and set about exploring it with
her tongue expertly. Both of us where in raptures of pleasure first one
then the other of us would pull one of us onto our backs or on top of the
other. Then we ended up face to face and I grabbed her cock and placed it
parallel to mine with my hand round both as we kissed forcefully and wanked
us both together. 'God I love that!', she gasped, 'but I have a slightly
unusual request, I want to fuck you babe!'.

At that moment I would have let her remove my legs with a chainsaw, I just
hoped that big cock wouldn't be as painful in my tight virgin arse, which
has only had smaller dildo's in. I told Roxanne I needed three simple
things for her to do me, lube, gentle, condom. I opened my top drawer and
produced lube and condoms and proceeded to slide on onto her cock and cover
it in lube as she did the same to my bum hole. Then she got me to lay on my
tummy and kissed and stroked my back and arse, it was heaven, then she
eased two fingers into me. I felt my arse stretch comfortably, she knew
exactly what she was doing. Then she proudly explained, 'Well I have 4
fingers in you quite deep so you should not have much trouble taking me'. I
was amazed and pulled her closer for a last kiss face to face before she
got on top of me and before I thought she had two inches in me I could feel
her balls and tummy against me, it was fucking ecstatic! She was an expert
and kissing and touching me and whispering loving comments all the time,
god I never wanted this to end.

It's one thing to hear a woman cumming, another to hear a man grunting to
ejaculation, but to hear a woman's voice lose control as her cock explodes
inside you is something different altogether. I felt the volume of sperm
and the intense heat even through the condom, each spurt so powerful. Then
she rolled me onto my back and lifted my legs up, my god she's just cum and
she's still going, I thought. She eased her fingers into me and worked them
in deeply then she took my semi hard cock in her mouth and sucked it. Her
fingers knew exactly what I needed and they explored until they found my
prostrate and synchronised the motion with her mouth, in less than a minute
I came so hard I genuinely felt that if I died right there and then I would
have been happy but for the want to do it again another time. She expertly
sucked my cream out and swallowed some, then came up to my face and shared
the last of it with a kiss, 'Next time you can fuck me darling!', and
collapsed half across my chest. I passed out and she must have done the
same, wonderful!