My first time was with a dark haired escort, I phoned and had her to come to my place. She was South American, slim build, nice face and breasts, cute accent. I was really nervous and not sure what I wanted or what was safe, I had all sorts of thoughts running though my mind, anyway, I ended up asking her to do a striptease for me. I thought at least I could get to see a shemale for real, after a while she got down to her birthday suit and holding her tool. She waved it in my face, laughing, saying did I want to suck it, part of me did, (in fact part of me just wanted to bury my face on the end of it) but I just did not know what to do, so I said 'no' and asked her to wank off, which she did standing in front of me, she left a pool of cum on my wooden floor for me to clean up later.

The one good thing about this rather poor performance on my part was that it got me over my doubts, 'what will happen', 'will I be able to stop it', 'does it mean I’m gay if i suck cock', and worse of all ‘What if she tries to fuck me, am i prepared to be a bottom', etc. A week later I called the same girl, as she came in I could she her smiling and straight away she asked if I was now ready for more; so I just said yes and we both stripped got onto the bed. We played with each other for a while, I was mainly fondling and kissing her breast, I was still unsure about heading south but slipped my hand down there and started to play with it, she soon got hard, it was smooth and wet, and was maybe 6 or 7 inches, it felt good to finally hold/touch a TS cock. She turned the pace up notch by turning round and going down on me (69 position), this left her cock in rubbing up on my face, it was uncovered wet with pre cum, but by this point I did not even think about it, I just put my head forward and sucked, it felt strange to have a cock in my mouth and I could feel it hit the back of my mouth as she pumped forward - face fucking me. After years of wondering what it would be like it was good to finally be doing for real.
After a while it was clear she wanted to do more, she had been steadily using one finger and then two up my arse as she was sucking away on my cock, which was more of a turn-on than I could possibly imagine. I thought that I may as well find out now, so I allowed her to slowly pull my legs up and over my shoulders as I lay on my back, she covered up and pushed forward, as I watched her slip into me, I had expected it to hurt but it was ok, she pumped away for a while and I could feel her cock getting stiffer and her pounding harder and harder, as she looked down at me saying 'you are my bitch now' and smiling, she came as she was pulling out.

Having just been fucked up the arise for the first time in my life I was somewhat unsure what to feel but one thing I was sure of, was that I wanted to fuck her back, partly because I was horny, but also because I wanted to be ‘even’, now, I know its stupid but I did not want her to leave feeling I had been her bitch. So I pulled the duet off the bed and put it over a nearby table which was a just the right height, and asked her to bend over, she bent over face down, leaving her arse in the air, she said to go slowly as she had, At first I did, but then as I got more and more into it I went faster and deeper, I’m by no means superman but I am quite large and thick and the thought / sight of her being fucked up the arse by me and her whole body slapping up against the table with every stroke I took was such a turn-on, I just could not hold back and fucked her arse for all I was worth, watching her squirming about on the table top with my cock buried all the way up her arse. Then I shot my load inside her, covered, and collapsed on her back panting and moaning.
She left shortly afterward looking dazed and confused, as if to say what happened to the quite shy guy I met last time, I can’t say I blame her!

Overall it was a good time and although I normally go for girls, every once in a while I still find a stiff shemale to have some fun with.