My Story - Taking The Plunge free porn video

I didn't know whether to scream out in pain or ecstasy. I'd often dreamed of having a penis that big but, to be honest, those dreams were more centred on it being a replacement for the rather feeble specimen that I was stuck with. It was not without good reason that my school classmates nicknamed me "Pinprick" and whilst puberty helped a bit, it was nowhere near enough for me to feel confident in putting it, or myself, about. And now, it was just dwarfed against the amply sized organ that had just penetrated me, stretching my insides to the point of pain. But as quickly as the pain had come, it subsided, replaced by a shiver of delight which engulfed my body as it responded to the rhythmical thrusting. And like an accelerating steam engine, the thrusts got faster and faster until I felt the explosion of warm cum deep inside me, my suitor's member pulsating as it deposited its load! And that was the moment I saw the rest of my life mapped out in front of me. Sure, I could carry on as before and there'd be nothing wrong with that. But as my companion's penis, still deep inside me, gradually lost its hardness, I realised that all of my preconceptions were wrong. Despite all of his male bravado, his masculinity & manliness, his impressively sized cock and everything else, he was helpless to my charms. And as soon as that cock of his decided it was ready for action, he was helpless and I was in complete control. Because that's the power that women have and whether it was my stockings and suspenders, stiletto shoes, deep red lipstick or any of the other feminising items I was wearing that turned him on, I don't know but for all of his masculinity, the truth was that he was putty in my hands and did exactly what I wanted him to do. But I'm getting ahead of myself. Let me set the scene for you. To all intents and purposes, I was an ordinary guy called Tony - age 32, divorced and with a humdrum job in finance. And like most other guys, I had an eye for the ladies - in fact that's what drew me to Alison ten years ago. In those days, she was pretty in a plain sort of way but very shy. We were made for each other but I always felt that, under the surface lurked a minx so, for her 25th birthday I treated her to a makeover and photo session. Well I was right about her being a minx. Those photos were sensational and she was soon wearing heavier makeup and more feminine clothes which I wasn't complaining about. But then she became more critical of me. Somehow, I no longer measured up to her expectations of what her man should be like and the marriage quickly deteriorated until one day she decided that she'd just had enough, started shagging her boss and quickly demanded a divorce. Sadly for her, at the time we divorced there was hardly anything to split and after her boss decided to return to his wife and kids and seek forgiveness, she was on her own struggling to make ends meet. Big pity that she didn't hang around for another few months as my old man died leaving me a ?5M fortune in stocks and shares. He kept that very quiet while he was still alive and I always thought he was as poor as I was. So I quit my job and have lived the life of a playboy ever since. But I digress. I'd love to give you the usual story of realising I was different at age 5, sneaking into my sister's bedroom to try on her clothes when she was out, struggling with the feeling that I was trapped in the wrong body and finally discovering my "true self" but there was none of that. I had a happy childhood doing boy things, chased as many girls as the next guy when I got to puberty (not that I ever caught any of them but that's another story) and the thought of wearing women's clothes had never crossed my mind. And as for the thought of having sex with another guy - ewwwww! The turning point, when it came was one of those pointless discussions one has at dinner parties. Eight of us had got together, four guys and four girls. Somehow, we were all single - three had never married and the other five separated or divorced - and as usual, the conversation soon degenerated into a battle of the sexes with us guys complaining that we had to take responsibility for everything while the girls just seemed to spend hours putting on makeup and deciding which outfit to wear and the women all arguing that us guys had no idea how hard it was living up to society's expectations of how they should look. I'm still not sure what prompted me to declare that I was up for it when one of the women suggested that if being a woman was so easy, then we guys should have no problem showing the girls how it's done. The other guys became strangely quiet at that point although the look on their faces as they turned towards me left no doubt that they thought I had taken leave of my senses. And before I had time to reconsider my enthusiasm, Nicki the host got up and said, "OK Tony, no time like the present. Come with me." As I followed her upstairs to her bedroom, I was starting to mentally question whether this was a good idea but it was quite apparent that any U-turn now would garner even more ridicule from the other guests that me reappearing as a drag queen. So I sat on her bed as commanded while Nicki collected a few items that she thought would fit me and then sent me to the bathroom to get changed. Needless to say fastening the bra and the rear zipper on the dress got the better of me but with Nicki's help they were soon done up. I slipped on the heels and gingerly made my way to the door. "Where do you think you're going?" asked Nicki sternly. "I'm not finished yet." I sat back down and Nicki proceeded to apply all manner of cosmetics to my face before finally removing a medium length blonde wig from a box, brushing it out and then positioning it on my head. "I think we're finished," she declared as she stepped back to admire her handiwork. "Come over here and take a look." I walked over to the full-length mirror on the far wall and stopped in my tracks. "Fuck me," I exclaimed. "I look hot." "Not the sort of language I'd expect to hear from a lady's mouth," laughed Nicki, "but I will admit that you do make a surprisingly attractive woman." And I admit that I did feel a stirring "down below" as my male parts made their well tucked presence felt. What was causing this reaction, I don't know. Perhaps it was the blonde hair with its loose curls cascading down onto my shoulders that reminded me of Cameron Diaz, a poster of whom on my bedroom wall had provided me with plenty of wank fodder as an adolescent youth? Or maybe the smoky eyes and deep red lips that just seemed to be inviting me to come over for a blow job? Surely not the tits, created by Nicki with a couple of socks and judicious use of surgical tape that now seemed to be bursting out of the low-cut dress she'd given me? My newly feminised legs clad in black stockings that were just crying out to be spread to reveal a moist pussy? Or could it be the stilettos which are always a turn on to any red-blooded male seeming to signify, in my sexist mind anyway, that the wearer is "up for anything?" Whatever it was, I didn't really care because at that point in time, all I wanted to do to the woman looking back at me was to shag her senseless and my penis, still unaware that my reflection and the male it was attached to were one and the same person, was getting itself ready! The gasps as I made my way back to the dinner table were audible. Of course, the women made a big fuss telling me how gorgeous I looked and all of the other sycophantic small talk that women do so well but it was the guys" reaction that was the most telling - if the woman in front of them wearing a red dress, black stilettos and immaculately made up had been anyone other than me, they'd have all be sniffing around her like bees around a honey pot! But as it was, they were clearly battling with the idea that they were all sexually attracted to a woman who, until half an hour earlier, had been a guy just like them. Finally, one of them spoke. "Come on lads, let's go to the other room. All of this genderbending stuff is too much for me." As I was wondering whether I still counted as one of the "lads," Nicki declared that she and the other girls would like to get to know "Tanya" as she named me a little better so I stayed at the table and, as our wine glasses were repeatedly topped up, the conversation got a little looser. "You know," laughed Nicki, "any one of those guys would have been in your knickers at the drop of a hat!" "Yeah right," I replied unconvinced, "so you're telling me that they'd all overlook the slight issue of what's lurking in my knickers?" "Well, not exactly, but Jack blushed and looked down until he left the room, well at least that's when he wasn't sneaking furtive sideways glances at your legs, Dave couldn't take his eyes off your tits and Pete just crossed his legs and put his hand on his lap, presumably to hide the growing problem inside his trousers." The other girls cackled with delight as Julie, another of the guests piped up. "That's the thing about guys. They think they can control us but as soon as we put on a pair of heels and some lippy, they're helpless to our charms!" "OK, fair comment," I laughed, "but they're not going to be too happy when they realise they're confronted with a pole, not a hole!" More cackling from the girls. "Oh, don't worry about that," glggled Julie, "half the men I've met would stick it anywhere just to avoid wasting a good erection and I'm sure it won't take them long to realise that there's a perfectly good orifice for it a few inches back!" "Oh, Julie!" cried the others in mock disgust. "That's gross." "Maybe so," laughed Julia, "but I don't hear Tanya putting up a fight." And she was right. Granted, the thought of having someone's dick rammed hard up my arse wasn't exactly enticing, the whole idea of trying sex from a completely different standpoint - a female standpoint - was a real turn on and if that was the nearest I could get to having a vagina, then so be it. So I just smiled enigmatically and left the other girls to decide for themselves what they wanted to read into that reaction. At that point I noticed the clock on the wall which said it was well past 2:00am. It was time to go but I wasn't going anywhere until I had heard what the girls had to say about my performance. "So," I started, "how did I do?" "Well," started Nicki, "I have to admit that you took to being a girl much better than I expected. But you've only really scratched the surface and there's far more to being a woman than just looking gorgeous, especially when you've been helped as much as you have been tonight." "Typical woman," I laughed, "you'll never admit when you're wrong. Anyway, I'd better get changed back." "It's late," replied Nicki handing me a carrier bag containing his clothes, "go home as you are, I was going to get rid of that stuff anyway." And as I walked the short distance back to my own house, alone for the first time that evening and with the click click of the stilettos reverberating around the otherwise deathly quiet estate, I just couldn't help smiling. I'm sure a psychologist would have a field day suggesting that I had deep rooted gender issues caused by some childhood trauma or other but the truth is that whilst completely happy as a guy, being a girl for the evening had opened my eyes to a new world. And as I removed the final vestiges of femininity and flopped down onto my bed, I had no intention of walking away from that world - it was far too much fun to even consider not running headlong towards it. I normally sleep in on a Saturday morning but was woken by incessant banging on my front door. I pulled on a dressing gown and opened the door to see Nicki standing there with what looked like my phone in one hand and a large black plastic bag in the other. "Typical airheaded blonde," she laughed handing me the phone, "you left this behind!" "Oh yeah, sorry," I replied still half asleep. "And these are for you too," Nicki added handing me the black bag, "surplus to requirements as far as I'm concerned but I thought that Tanya may like them. If she's still around, that is." Nicki had one of those cheeky smirks on her face that indicated that she knew exactly what I was thinking but I wasn't going to let her get the better of me. "And what makes you think that Tanya is still around? I proved my point as you well know so why would I still need her?" This time it was my smirk that told Nicki all she needed to know. "OK, I get it," she laughed sarcastically, "anyway, girls night out this Friday. If you do happen to look in a mirror over the next few days and see Tanya looking back, tell her to come round to my place at 7:00." As I closed the door and walked to my kitchen to get breakfast I laughed out loud. This was getting even better by the minute, I'd often seen girls out together when I was out and about and could only imagine what they got up to. Now I was going to find out. But what I did know that I needed to do my homework. It was one thing being dressed up by Nicki in the safety of her house but holding my own on a girls' night out in full view of society at large was on a completely different level. Time to do some research. I sat down at my computer, opened google but what to search for? I decided to start on familiar ground so typed in t-r-a-n-n-y and pressed enter. That was no help - a few photos of individuals who quite definitely weren't presenting as the gender they were born into but were wholly unconvincing as the opposite gender. But then I caught sight of a message stating that safe search was enabled. After a couple of clicks to disable it, WOW! Image after image of beautiful women many engaged in all manner of sex acts! Full frontals of girls, girls being shagged by guys, girl on girl action, blow jobs, threesomes - it was all there. These girls looked amazing and any guy would have been gagging for sex with them. In fact the only thing that was out of the ordinary was that every single one of them had a cock - some tiny which I later discovered was probably due to them taking high doses of female hormones and some absolutely huge putting my own rather pathetic specimen to shame. Some of the girls also seemed to have had their balls removed; I'm not normally keen on seeing bodies with limbs or other bits missing but there was something strangely beautiful about seeing their dicks without the usual junk hanging below. I sat back in my chair. I've never once looked at a man as a sexual partner, in fact I've always found the idea quite repulsive, and yet as I looked at the hunks on screen with their members planted deep inside the girls," back passages, I felt a rush of envy. Not for the guys fucking those amazing girls (although having a dick as large as there's would have been nice) but for the girls themselves who were quite obviously not letting the fact that they had penises get in the way of being rogered senseless. Heaven only knows how many times I jerked myself off that afternoon as I dreamed of being taken from behind by a well-hung hunk, or perhaps even one of the better endowed girls who, paradoxically, seemed quite happy to adopt the male role in the sex act. So that was that. I forgot any ideas of going on a girls," night out to discover my "true self," bond with other girls or just to have a giggle over a few glasses of wine. I now had one and only one aim. To get laid by a guy! I already knew from Nicki's that I could turn guys on but if I was going to get a decent looking guy into bed, I had to up my game. And then some. Over the next couple of days, I joined a few online trans forums to learn everything I could about the trans world, where to get what I needed and the experiences of others, particularly those who were sexually active. And by Friday, I was ready to put my plans into action. I'd gone through the bag of things Nicki had brought over and found some fairly androgynous clothes & flat shoes that I could wear as a guy on my way to the makeover I'd booked in the local department store and which would not look out of place when I emerged in full female mode afterwards. Thanks to Amazon, I was now the proud owner of a pair of D- cup breast forms which helped in creating a more convincing cleavage than the socks did and I found the most gorgeous cobalt blue dress with a low cut front to show my boobs off while browsing in the store after my makeover. Calf length but with a deep slit up one side, it would give a tantalising view of my stocking tops and practically invite guys to fantasise about what lay above them! By 7:00pm I was ready and made my way to Nicki's. The other girls were already there by the time I arrived and whilst they all looked amazing and eminently shaggable, tonight was not the night to pursue any of them. The conversation started off normally enough. The usual girl fodder of compliments about hairstyles, enquiries about where dresses and shoes had come from and that sort of thing. But as the third bottle of wine was opened, Julie decided to make things rather more interesting. "So girls. When did you last time have a cock inside you?" The replies came thick and fast! "Not since I threw my bastard of a husband out!" "Three months ago but I blinked and almost missed it!" "Well I do try to give the dildo an outing every couple of nights but, as for anything attached to a guy, too long ago to remember!" Then Julie turned to me. "I hope we're not putting you off!" The smirk on my face left no doubt that my interest had most definitely been piqued and I was now getting seriously turned on by the thought. "Not at all, in fact the thought of ending this evening without some gargantuan cock unloading itself inside me is just something I don't want to contemplate," I replied to shrieks of laughter from the girls before adding "but all of this is new to me, what should I expect?" "Well let me tell you from experience that it doesn't matter where it goes - front, back or even in the mouth - nothing beats the feeling as it stretches everything as it goes in, the sheer joy of feeling it pumping backwards and forwards and then the climax as he erupts inside you, his throbbing dick disgorging every last drop of warm cum before he collapses in a heap on top of you and holds you tight, waiting until he can muster up the strength to do it all over again. Just make sure that you choose your man carefully as there's nothing more disappointing than getting all fired up, only to find out that you'd have got more pleasure from a pencil!" More shrieks of laughter and knowing nods from the girls. Talk about throbbing dicks! Mine was certainly starting to make its presence felt and I wanted to experience what Julie had described more than ever. I just hoped that I could control it long enough for the erection to die down without incident and not be faced with the deeply embarrassing alternative. "I think our Tanya is on a mission tonight," laughed Nicki who then passed me a small tube of gel and a couple of tampons before continuing, "you'll need the gel to lubricate him before he penetrates you and the tampon will stop any leakage when he's finished." By that time, it was getting close to 9:00 so we gathered our things and headed out to the taxi waiting outside. To avoid any potential embarrassment for me being seen by someone I knew, Nicki had suggested that we try a club around 15 miles away that had had good reviews online. She also enigmatically mentioned that she had laid on a little surprise for me but wouldn't tell me what it was. It was around 9:45 before we finally got inside the club. I looked around and instantly regretted all of the times I'd leered at girls in the past. Chests were being puffed out, lips licked suggestively and our group was quite obviously the topic of conversation as eyes looked our way. Did girls really have to put up with all of this pathetic crap every time they went out. But there again, I thought, if I really was going to enjoy the sensation of that throbbing dick so graphically described by Julie, I was probably off to a good start. But whilst I may have been deluded about my new found feminine charms, I'm not stupid and none of those guys would have taken kindly to finding out that the goddess before them was as male as they were. I needn't have worried as I turned back to the group and saw Jack, Dave and Pete walking over. So that was Nicki's surprise! "So," asked Nicki, "which of you gorgeous hunks is going to make Tanya a real woman tonight. By all accounts she's hot for it and won't take no for an answer." The guys looked uncomfortable, not quite knowing what to say. This was going to be fun and, given their various reactions when they first saw me at Nicki's, there was a reasonable probability that at least one of them would be a willing volunteer! But I did sense some reticence even so. "Oh come on," I laughed, "don't tell me that you're all getting cold feet? Jack, wouldn't you like to know what's above my stocking tops?" Jack went a dark shade of beetroot! If he's ever going to get anywhere with a woman, he really needs to stop blushing. There again, what dark thoughts or perversions could he be hiding? But I needed a man, not a ditherer so I turned to Dave. "Dave, aren't you just gagging to bury your face in my tits before taking me to heaven and back?" "Um errrrrrr." Try as he might, Dave just couldn't get the words out almost certainly because whilst his head was telling him that the gorgeous girl in front of him was one of his mates, his heart (or more likely his cock) was telling him something completely different. "And Pete," I continued turning to the final member (LOL) of the trio "is that uncontrollable penis of yours still telling you that I'm the girl of your dreams. Or should I say wet dreams?" By this stage, the men were speechless as the girls were helpless with laughter. Where had all their male bravado gone now? Desperate to diffuse the situation, Jack got up and said he'd get the drinks in and Dave quickly followed him to help leaving just the girls, Pete and me at the table. The girls were still laughing as Pete turned to me and very quietly whispered in my ear. "I'm up for it if you are but keep it quiet as I'm dead meat if the other guys find out." "Oh I'm definitely up for it," I softly replied, gently putting my hand under the table to feel the obvious bulge forming in his trousers, "and we don't want to waste a good hard on do we?" As I was saying this, my mind was in turmoil. I still had this nagging doubt about the homosexual angle and there was no way that this encounter was going to end in any other way than with Pete's organ inside the one orifice I had able to cope with it. And yet, as I looked down at my ample cleavage, the sheer black nylon encasing my legs and my beautifully manicured nails gently caressing Pete's now obvious bulge, this just didn't feel like the foreplay for a homosexual act. I felt just as female as I'm sure Nicki and our other companions did and, as a female, I wanted to end the evening with a man inside me. And I wanted it badly! "OK," smiled Pete "we need to get out of here. I'm going to need to say some pretty offensive things to avoid suspicion. Please just follow my lead and don't take offence." Jack and Dave returned with the drinks and taking their seats, passed them round. "What is that?" asked Pete pointing at my Bacardi & Coke. "What happened to the pints you normally sink Tony?" "It's Tanya if you don't mind," I replied, "and I just preferred something a little more feminine." "Oh, don't make me laugh, Tony. Don't you think it's about time you stopped this charade? You look ridiculous and what on earth were you thinking of even considering that one of us would want to fuck you?" By this time, Jack, Dave and the girls were just sitting open mouthed at the row that was developing. "Oh no," I replied getting into the swing of it, "you know full well that you and your mates can't take your eyes off me. What's the matter, are you all afraid you may just prefer a hot tranny like me to a real girl?" And as I said my piece, I gently stroked his hand with my manicured finger. "You fucking pervert," he shouted, "I've had enough of this. I'm going home." And with that, Pete stormed out of the club. Jack and Dave got to their feet to follow him. Time for some quick thinking. "Don't bother going. Pete's right," I exclaimed, "it started as a bit of fun but it's got way out of hand. You two stay with the real girls. I'm going home. I've had enough of this girl thing." I'll come with you called Nicki as I gathered my things and walked towards the door. Once we were out of sight of the others, both of us burst out laughing. "My god, you two were good! You had me fooled for a minute or two!" giggled Nicki helplessly. "Now you go and enjoy yourself but be careful. Pete's a good man but you just never know." "I will," I replied "now go back to the others to make sure they stay put for a while. And as I stepped out into the night air, I saw Pete waving to me from over the road so went straight over to him. "I'm sorry about that, I hope I didn't go too far," he said. I didn't reply, I just moved closer to him and felt his strong arms hold me tight. Our lips met and soon our tongues were teasing each other with their ritual dance. I felt my whole body relax as it was engulfed with a tingling sensation, the like of which I had never experienced before. As our lips parted for air, Pete said we needed to get out of there before the others decided that they too had had enough and caught us at it. So arm in arm, we walked to the taxi rank for the ride back to Pete's flat. Whether the taxi driver suspected anything, I doubt because neither of us said a word, our tongues being too busy exploring every square inch of each other's mouths. Finally, we were safely inside Pete's flat, and after I'd touched up my lipstick in the hall mirror (something I've always found a particular turn on when seeing women do it) we were sitting together on the sofa with me curled up on his knee and with his arm protectively round me. "Tell me," started Pete, "when Nicki asked which one of us was going to take you, did you think you'd get any willing volunteers." I thought for a moment. "I don't want to sound conceited but the honest answer is yes. In fact I thought it could be any one of the three of you because, thanks to your reactions when you first saw me last week, you were all battling with the simple problem that on the one hand, you knew it was one of your mates in a dress but, on the other, you were all getting turned on. Hell, I'm having enough trouble coping with the disappointment that I can't fuck myself!" Pete laughed. "You're right. Jack, Dave and I met for a beer in the week and, after we'd gone through the predictable "What on earth was Tony thinking?" comments Jack just came out and said that the biggest problem as far as he was concerned was that the best looking bird he'd seen for years was a guy and one of his mates. Dave nodded and said that that was the problem these days. You just can't tell and you could be shagging an amazing looking girl one minute and find out that she used to be a bricklayer called Kevin the next." "And what pearls of wisdom did you add to the conversation?" I asked in mock indignation. "Honestly? Very little. I've thought about little else since I saw you at Nicki's last week. I've masturbated while imagining having sex with you, then felt disgust when it was all over, only for the whole cycle to start again a couple of hours later. So while the guys were making their pronouncements, I just shook my head, told them it was all a bit too weird for me and changed the subject to the football results before they suspected anything." "And do you still want to have sex with me? You know it's going to be a little unconventional if you're not used to that sort of thing." "I know and to put the record straight, I will be going somewhere I've never been before but it's a small price to pay for realising my fantasy." And, as things started stirring underneath me, it was obvious that the time had come. And that was the cue for Pete to stand up, still holding me tight and carry me to his bedroom. Pete gently put me down on his bed and while I took off my dress, he unzipped his trousers and set his cock free. And it was definitely a cock not to be ashamed of. I handed him the tube of gel and told him to put it on while I moved my panties to reveal what I'd seen frequently referred to as my boi-pussy on the forums. Pete pushed me roughly onto the bed and I instinctively raised my legs and backside to give him uninhibited entry. And with one push, he was in, causing me pain of the like I had never experienced before but quickly subsiding as things stretched around him. And the description given by Julie earlier just didn't do the experience justice. And as Pete was thrusting backwards and forwards, even my diminutive penis decided it wanted a piece of the action and was soon standing proud. Unperturbed, Pete grabbed hold of it and soon we were soon both heading to climax with Pete erupting inside me and me simultaneously spurting upwards like a fountain. Needless to say, after that a clean up was needed by both of us and I was particularly keen for Pete's cock to be spotless because of what I had planned next. Back in bed together, it was soon apparent that Pete was ready for more. "Pass the gel please doll," he commanded. "No need for what I have planned," I replied as I moved down to his dick, once again standing proud like an obelisk. I gently took it in one hand and licked the pre-cum off the head before surrounding it with my lips and gently sucking it. Instinctively Pete pushed forward and soon I had several inches of it in my mouth almost causing me to choke. I playfully bit it and he retracted it enough for my tongue to dance around the head while I moved my head rhythmically up and down and sucked hard. All too soon, I sensed the unmistakable throb signalling that I was about to get a mouthful of warm cum. And when the inevitable happened, I just swallowed the whole lot, the salty taste with just a hint of sweetness lingering in my mouth for several minutes. But while Pete had climaxed I had not and my diminutive member was standing upright like a small puppy begging for a treat. And Pete, to his credit, realised that there was still work to be done and gently caressed it while, at the same time, experienced the taste of his own cum as his tongue explored my mouth. And soon, after I too had reached climax, Pete moved down and tenderly kissed the head of my retreating member. The significance of that simple act was not lost on me - a blow job or offering me the chance to penetrate him would have been weird for both of us - an unnecessary role reversal - but the kiss just signalled his respect for me and his acceptance of my burgeoning sexuality. But it was obvious what we both craved and soon Pete was back where he belonged, once again shooting what was left of his load inside me before cradling me once more in his arms. The human body has many fine features but as I lay there, I did lament the fact firstly that men needed time to recover between lovemaking sessions and secondly that they did not have an unlimited supply of cum. But even the thought of him inside me made me tingle with delight as I eagerly awaited more. My eyelids sadly had other ideas and I quickly drifted into a deep sleep. Epilogue I would never see Pete, or indeed Jack and Dave, ever again after that weekend. Pete was very sweet about it and, as we curled up together in his bed the following morning, he told me that sex with me was the best he'd ever had but he'd never be able to look Tony in the eye ever again. He went on to say that even if I stayed as Tanya from that point on, whilst he would never for one moment regret what we had done, those around him would be less tolerant and he needed a girl he didn't need to keep hidden. He said that he hoped that one day, people would be less judgemental about trans people and their partners but the truth was that that day had not yet come. But was I upset? Not a bit of it! Sex with Pete was amazing and I did have a pang of regret that, thanks to my chromosomes, this was not the start of a wonderful and loving relationship. But the thing was that my mind was already in a world a long way away from his. His world almost certainly involved him finally finding a sweet wife to settle down with while I was already dreaming of getting a real pair of tits to replace the fake ones, losing my balls which thanks to their endless ability to produce testosterone would only end up holding me back, and becoming a fully fledged "chick with a dick." It was not a case of trying to banish Tony from my life. In fact, as I sat there I couldn't help thinking that if I'd not discovered an alternative, I'd happily live out the rest of my life as him without a single regret. And yet here was another world beckoning me and I was walking towards it, not because I felt I had to but because I chose to. The rest of my life could be ten times better if I wanted it to be and, as I thought about Pete's amply sized cock thrusting away inside me, my mind was made up. And whist Pete would always be the guy who took Tanya's virginity, I was well aware from my internet research that there was an almost unending supply of guys bored with being the dutiful husband who were only too happy to try something a little different with girls like me. Maybe one day our paths would cross again. Perhaps the thought of missing out on the best sex he'd ever had would finally get the better of Pete and he'd be back begging for it once more. Maybe I'd tire of the shemale life, have a full sex change and we'd elope to some far-off land, away from the prejudice he feared to spend the rest of our lives as man and adoring wife. Or maybe, just as something inside me had clicked, Pete would find himself and start to frequent trans friendly clubs where we'd bump into each other and pick up where we left off. But for now, it was a Saturday morning, neither Pete nor I had anything else planned and if we were going to go our separate ways, I was sure as hell going to milk every last drop of cum from him before we did. And just as he had been the night before, he was powerless to resist.