Should I shouldn't I - first time trans
I live in a provincial city where the escort women travel through. By the way, paying for sexual action is legal in my country. So there is a constant stream of different women offering their service. I was feeling the need one night so rang an advertiser offering massage with happy ending. The address was a local hotel so off I went.
On reaching her room I discovered that 'she' was a transsexual woman with a cock. She was Japanese with small breasts an average size cock, quite feminine and attractive and overall pleasant personality . Decision time. I had from time to time fantasised about this situation so what the hell - I decided to stay and try a new experience.
She started with the massage experience, me lying on my front and her straddled over my bum, oiling my back. Pretty soon I could feel her five inch cock bouncing on my back. Turnover came pretty soon and she was riding on my chest with her cock a few inches from my mouth. She enjoyed me playing with and sucking her pointy tits but what she wanted was quite clear and she said 'feel free to suck me if you want, I won't cum cos I have ejaculated so often today there is nothing left'. Again,, what the hell? I took her firm cock in my mouth and found that I really enjoyed rolling its soft firmness around my mouth as I sucked on the glans. This evoked some heavy sighing from her as I noticed her balls tighten up. She did cum but no spurts.
We spent some time resting on the bed and talking. By this time I was so far down the rabbit hole when she asked 'Would you like me to fuck you'? I said yes. 'Have you ever been fucked there before'? was the next question, 'I don't want to hurt you if your new to this'. As it happened I have had a number of medical procedures on my lower colon so my rosebud is used to large metal objects. I said ok go for it. Another new experience and bloody big surprise. I liked it. She had me lie face down with my bum raised a bit, got behind me and with plenty of lube pushed the head of her now hard again cock into my bum just a few inches and rode me gently. As she did she reached under me and wanked my cock till I came. Benefit for her being as I cum the contractions of my anus gave her another thrill. After another chat I left saying to myself 'Wow did I just do that'? Would I do it again for a change of pace - probably.
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