First TS sex

I think I was near my 35Th birthday and, believe it or not I had never had experience with a transsexual. I had plenty adventures with men and liked it very much as well as with women. Decidedly I was completely bi.

As I wrote in previous stories, I’m writing about near 30 years ago. It was not as common as today, no way thinking to come out of the closet.

I was working with a engineering group, developing housing projects and our working hours were far from normal. I was preparing a presentation for our customers and stayed specially long in the office. I came out from the underground parking near 11 PM. The street wasn’t to well illuminated. Arriving to the first corner I saw a tall girl standing there, dressed in a extreme short mini skirt and a top, with most of her beautiful boobs showing. I gave her a good luck and she made me a gesture indicating me to stop, but I continued. When I arrived home I was already regretting my stupid decision, but didn’t return. Had a quick dinner, took a shower and went in bed, were I wanked thinking off the beautiful stranger.

Next afternoon, when everybody started leaving the office, I told my boss I would stay a little bit longer, to complete my work.

I really worked on the presentation but my thoughts were somewhere else. Around 10 I left. When I came out I saw her standing at the same place, so I pulled slowly next to her and let the window down. She obviously recognized me, because she told me “Today you’re not afraid of me? Will we go somewhere or will you stay here looking?” If I had any doubt, her deep voice told me what she was. Finally I made up my mind, released the lock and she entered the car. I drove away, looking for not to busy streets. She asked me were we were going. In the meantime she was touching my legs and had already caused a proper erection. “I see you know what you like...wait until I have it in my mouth” Before leaving the office, I took with me the keys to our guest flat, as I knew that nobody was using it that day. I proposed to go to a very quiet place to have some drink and fun and of course she agreed.

We went into the building and I was praying not to be seen when we entered into the elevator. Once in the apartment really didn’t know what to do. It was all to weird for me. The girl went to the bar and prepared 2 very stiff whiskys on the rocks, took my hand and took me to the sofa, sitting next to me. She unbuttoned totally her shirt, exposing 2 firm and round breast. While I was staring amazed to them, she took my head and brought it down, putting her nipple in my mouth. At the same time she unzipped my trousers, taking my almost erected dick out and wanking it slowly. It took no long before we were both naked and me playing with her full 8” erection. We went to the bedroom were she started sucking me, At the same time she was running one of her fingers in and out of my asshole. I noticed she had brought Vaseline and was lubricating me. Once she had me panting, turned me around with a pillow under my belly and entered me strongly. It was a time since I had been penetrated and normally it was in a gentle way, step by step. Here it was different. With the first push I had over 5” inside me and it was thick! The sudden pain made cry out and she started fucking me, wile with one hand she was spanking me and saying “Now you know what it is to be fucked, do you like it? Tell me, do you like to have it all up your ass?” Finally I had it all inside me, here balls bouncing against my ass and slowly I started enjoying it. But as long as I didn’t answer she kept hitting me (and it was a very nice feeling) I didn’t say a word. But as soon I raised my ass, in order to allow me to play with my cock, she started again: “You like it you bitch, tell me you like my cock” As I was to busy to answer, concentrating in getting all of it, she told me “Or you answer or I take it out and we forget about it!” You can imagine that suddenly I was grunting “Oh yes, I love your big cock, push it all in, fuck me stronger” and similar (and I wasn;t lying) while she rod me like a rodeo cowboy! Finally I noticed that she was coming and at the same time my cock started to deliver on the bed sheets. When she finally took her tool from my ass, came in front of me and ordered to suck it clean.

We dressed and she informed that it would be only 50, as she had enjoyed the evening also. Still today I’m sure it was good invested money.

When we left, I made a mental notice that the next day I would have to give a special tip to the maid in charge of cleaning and taking care of the apartment.
85% (20/3)
Categories: Gay MaleShemales
Posted by bloodyhugo
4 years ago    Views: 869
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2 years ago
Was it worth $50.00 or more
2 years ago
Man that was so hot. Made me hard. Thanks
4 years ago
transeuxals can be so special they ahve everything and so everything thanks
4 years ago
Thanks, it's nice to know people like to hear my experiences
4 years ago
id love my 1st experience to go like this. awesome