This is my first ever story written about my first ever sexual encounter with a transgender woman. I really hope you enjoy and want to leave me some feedback…

I have slept with many women in my life. I have been married, had more girlfriends than I can remember, several fuck buddies and far too many one nighters to tally up. Up until recently I have always been a guy exclusively into women, natural born female variety. Sure, probably like most guys, I have considered other options but always recoiled at the thought of getting it on with another guy. Oh God no, I could never do that! I kind of always thought, I can understand why girls want to be with other girls, but how can chicks ever possibly really be into men? We are not attractive. So yeah, I guess that made me pretty much heterosexual as you can get. Well, I always liked cocks. I said liked, not licked, get your mind out of the gutter. So there was always hope for change? Maybe.

So lots of women had come and gone (yes, and cum) and I guess I was getting bored of all that action. Maybe I needed something more. Something I had not yet discovered. Hindsight is a wonderful thing, as they say, and it allowed me to realise that I had never actually been in love with any of those women. Maybe now I needed a relationship to help me to grow as a person after becoming tired of all the conquering that went before. Maybe I just needed a change of some sort, some new interests or something like that.

I had been aware of transgender women for a long time, however, I had not really paid any real attention. I guess my relatively narrow minded approach to my sexuality left me thinking, despite an interest in a good looking girl with a dick, that was too close to liking men and that just wasn’t going to happen. One day I was surfing around online looking for some inspirational material that was going to help me with some DIY, if you know what I mean. I had actually been jumping around many different tube sites starting then skipping many videos. That was when I happened on a video starring the lovely Bailey Jay. That was when I actually started getting seriously erect for the first time in my search. My hard on was getting stronger and stronger and I didn’t have any motivation to move on to the next video. Not until it had finished and I was compelled to search specifically for more of Bailey Jay. It was only my eagerness to find as much as I could that stalled me from actually taking care of business at this point. When I did take matters into my own hand it was a very short time until I was spurting my cream all over in pure appreciation of Miss Bailey Jay. I thought, wow, she is gorgeous, cute and unbelievably sexy. There was something special about her and I am not even talking about the very attractive dick between her legs. She has been called a trap before, basically because you would never know she wasn’t a woman. Best of both worlds, all woman and a cock! This was definitely something to rejuvenate me from my general boredom.

A few years passed before I even took things further and actually had relations with a trans woman. In that time I was still into women but I also did a lot of trans surfing online and built up quite a collection of pics and videos. There are so many beautiful women doing porn and a lot of the ones I regularly watch have a penis. I think now I am at the stage where if she has a pussy or a cock then it doesn’t matter, it’s all gravy. I find her attractive and she has a good personality is all that matters to me.

The only thing that seems to be a problem for me is that you can easily meet girls but you can’t easily meet trans women unless you happen to live in Brazil, Thailand or one of the trans centres elsewhere. I don’t and so that basically led me to escorts. I checked out several sites and looked for several months not quite being brave enough to actually book anyone. Finally I did pluck up the courage. Actually the tranny I booked in the end wasn’t quite what I wanted. I don’t mean she was ugly, but maybe not quite as passable as I was hoping for. I was so nervous when I got there and she opened the door to me.

Before she opened the door I had actually considered just leaving, but I pushed myself. When she opened the door and said hi, I just said hi back and smiled nervously. Her photos were pretty accurate to the woman I was looking at in the flesh, although I would say they were maybe a couple of years old. She was standing there in a PVC basque, PVC knickers, stockings and PVC knee high boots with high heels. She towered over me which was not helping to ease my nervousness. She invited me in and shuffled past her in the direction she indicated.

There I was standing in the darkened bedroom of a girl wearing all PVC underware and boots standing towering over me. I was lost for words and my eyes were in line with a huge heaving pair of breasts bursting to get out of that basque. I actually became aware I was staring at her breasts and looked up at her. She smiled and looked back at me asking if I liked them. I said yeah, feeling very shy and not quite myself. I looked down trying to take in the view a little without seeming too obvious. I saw that those PVC panties were bulging.

She asked me, in a softened sort of whisper voice, if it was my first time. I nodded and realised I had stood back and was practically staring with my mouth hanging open but still far too nervous to do anything. She told me not to worry she would take good care of me, after money had changed hands of course!

When I did manage to speak with my dry throat I finally asked her if she could put on the lights a little so that I could see what was going on better. She turned on a bedside lamp and then said just you undress honey, I will be back in a moment. That’s when the girl goes to hide the money in a safe place before anything else happens. I got undressed quickly when she was gone trying to make sure my cock was good and hard. I couldn’t do anything with it! I was shit scared to be honest.

She came back into the room and walked over to me and took my hand and led me over to the bed. She looked down at my cock and cupped my balls in her hand. I was frantically trying to induce an erection in my head but it just was not happening. She kneeled down before me and moved in closer lifting my cock up to meet her mouth. I looked up to the roof, as if asking for divine erection intervention or something. I still wasn’t even sure I wanted to do this but was determined to see it through so I knew what it was like. She kissed my cock and then snaked her head around to lick and kiss my balls. She pulled my foreskin all the way back and took my head into her mouth, swirling her tongue around my head and intermittently kissing and licking it too. As my head was in her mouth she began to slowly bear down further and further to take my cock all the way in her mouth and she used her tongue around me to good effect. Bingo! Erection! And fast too all of a sudden, she sure knew how to suck a dick hard and I loved feeling my head against the back of her mouth as I momentarily choked her on it. My dick looks, in my opinion, very small hanging soft, but when it’s proper hard it looks dramatically bigger and that’s not just my opinion. There have been quite a few girls watch me get hard, mesmerised and wide eyed usually with a big growing grin on their faces also.

Anyway back to the story, mercifully I was now hard and effectively being sucked off and fondled by a chick that I knew had a big bulge in her panties. I was enjoying her blow job technique and also the wet fingering of my ass and the sucking of my balls individually into her mouth and the simultaneous hand job but I just had to see and taste her dick… My very first ever dick in my hands, in my mouth, well as far as I’m aware of anyway.

By this time I was a lot more into it, very turned on, very hard and now desperate for her cock. I asked her to stop and stand up as we switched places. I pulled her panties down quickly and she stepped out of them for me. Her cock was semi hard, I was happy to notice, and I could tell it was so thick. I put my lips around her head and she started to get harder immediately. I think overall I would have to say her cock was no longer than mine bu way way thicker so it was kinda huge compared to me really. I tried to suck her cock and I assumed it would be easy to do but I was wrong, it’s not that easy to just do first time ever. I would later forgive the girls that I considered to be shit at blowing cock, especially the younger ones who definitely had not had extensive experience. I was getting a bit frustrated that I was clearly not making her feel good, and then she started to go gradually limp! She stopped me and she asked me what I wanted to do. All I could think was having that big thick cock stuffed up my arse! So I excitedly replied “fuck me!”.

She pulled me to the edge of her bed and lifted my legs up and apart, lubed up her thick hard cock then began easing it into my nervously tight hole. She told me to relax several times as she persevered with entering me. It wasn’t too long before I felt her full width stretching me open and pushing deeper into me. She began slowly moving her hips, pushing her cock in and out slowly and I began to seriously enjoy the sensation her wide hardness was creating rubbing my g spot. It was not long before I, rather pleadingly, asked her to fuck me hard. She certainly did not disappoint with this, getting faster and deeper until her balls were making a rhythmic loud slapping noise against me. She momentarily stopped to push me further onto the bed and pushing my legs back from behind my knees she entered me again at an angle and depth that had me gasping! Oh my fucking God, this was being proper fucked I thought. She was roughly forcing herself deep and fast inside me and it felt great! While being fucked and even though I was so turned on my cock was just bouncing around seemingly very flaccid. Apparently this is quite common although I can’t understand it really considering I was loving this and horny as hell. After a while of serious hard pounding I began to feel a slow tingling inside feeling I know so well. My dick was getting semi hard and I was getting ready to cum! Never in my life before have I ever cum completely hands free, this was crazy.

I could barely speak through the intensity of the thrusting she cock deep inside me and my throat was hoarse from my heavy breathing, grunting and moaning. I managed to regain eye contact with her and breathed “I’m gonna cum!”. I saw a grin spread across her face as she seemed to thrust harder and deeper somehow, she kept repeating encouragement to me to cum, sow my seed, release my pleasure. Again I said only “I’m gonna cum”, it seemed to be the longest stretched out rise of release I ever had. Don’t know if it really was but it sure as hell felt long drawn out and utterly pleasurable. She bore down on me kissing my head, cheeks, nose, mouth, whispering “cum for me baby”, and then it all reached a head and I began squirting spurt after spurt of hot creamy cum all over my belly. I completely lost all recognition of what was going on around me for however long and when I came round I was laying there gasping for air as she sat between my legs smiling and stroking my legs. I was getting those after cum twitches and tightening of my ass and could feel her still hard inside me as I tightened around her width. Slowly she pulled out of me and whipped her condom off and began jerking off furiously. Very quickly I could see she was nearing her orgasm and I just stared in awe as she emptied her balls spraying her cum onto mine all over my stomach.

When she had fully finished she look at me, smiled and said “you are a very naughty boy” with a wicked smile. Then with her fingers she mixed our cum together and scooped it up and rubbed it on her ample big round breasts. I just lay there admiring the view and seeing her breasts shine in the light covered in our mixed cum and breathing in the utterly filthy scent of sex that filled the air.

Actually I wasn’t going to mention this but when I had cum hands free and she was still inside me I had this incredible welling of emotion that almost made me want to cry. I am a guy, I consider myself to be pretty damn manly and I can’t remember the time before when I last cried. Of course I forced it away, thankfully I was able to. I had never had a cock in my ass before, I had played with dildos and plugs but never a real live throbbing cock. That and the cumming hands free and the excitement of the whole thing was probably just too much for me I guess.

I don’t really remember much of my first time having sex losing my virginity, not even sure the time I sort of remember was actually the first. I know I will never forget the first time I had a cock inside me though!