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!