This is a print version of story My first time with a tranny by feinor11 from

My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.

In August 2007 I was 24 years old and was constantly masturbating to shemale porn. My best friend was getting married and my friends and I threw him a bachelor's party at a friends house. I had been curious towards one day hiring a tranny for sex, and had been driving while d***k on weekends around the red light district in my city where all the trannys were.

At the party we got extremely wasted and it was fun. We hired some sexy strippers and I had sex in my friend's bathroom with one of them. But there was something off my sex drive that night and after fucking the stripper I wanted more. I thought that more drinking would calm my throbbing penis but nothing could do it. After meditating the idea that that day would be for experimenting I found an excuse to leave the party and finally tough up to go to a tranny.

Of course I was wasted and I felt like superman and in no time y reached the usual tranny hangouts. I drove by for a while. My heart was pounding in excitement, I had a massive erection and I was very nervous. Finally, after seeing one that I liked since it was very late and there were few trannys in the street I got the courage to stop and ask her for her services.

She told me the price for a blowjob, and to fuck... she also gave me the option to go to a nearby motel. But since I was very nervous and it was my first time I asked for a blowjob. She told me to drive around to a safe place since the cops are always on the watch. We parked behind some apartment buildings and she told me to put my pants down. I already had a massive erection and she started rubbing my cock. I could tell she definitely knew I was a newbie for she kept asking me what I liked and what I did and some smalltalk. She started licking my cock, and then my balls and started teasing me. I was getting hornier by the second and she knew. She asked me if I had ever been with a tranny and I answered that it was my first time. She smiled and kept going faster. I knew she would try to rip me off taking advantage of that but I was so horny I did not care.

She then asked if for some more money I wanted to fuck her... I said yes, so she got out of the car, went behing some bushes, put a condom on me and asked me to fuck her. I was very nervous that someone would see us and was very clumsy. I think she got annoyed so she finally told me the price of the motel and that she would not charge me extra. So I decided to go.

We arrived at the motel and I was very shy for the attendants to see me. The girl took charge of everything, asked me for the money and so we went to the room. In the room she asked me if I wanted to blow her. I had never had a penis in my hands before. I was so nervous but at the same time I was so horny. I wanted to taste that big cock in my mouth. Taste the precum. It was all so exciting and new.

I accepted her offer to blow her, and started by licking her shaft and balls, then she grabbed my head and put her cock in my mouth. As I was blowing her, all the scenes from all the shemale porn I had watched came to my head. I suddenly felt a rush through my body and my whole body was pulsating with pleasure. I kept blowing her and as she was moaning she told me she was going to fuck me.

I had become a complete slave. I was enjoying my role as a bottom and felt my ass throbbing. This was all a very strange sensation. I was enjoying every single moment. I accepted her invitation to fuck me. She told me she was going to be gentle.

She put me on my back while she put a condom on. Then she lifted my legs, and dropped a few squirts of lube on my ass. I could feel my whole body pulsating. I was very nervous, i had butterflies in my stomach. Then she grabbed her cock, I felt it near my ass and she started putting it in. It hurt like hell but I was very excited to get fucked. She got it all in and I moaned a little in pain. She then started pounding me with no mercy for my pain and I could feel my cock almost as if exploding. I could not describe the feeling but I enjoyed it. I could see myself getting fucked and that image turned me even more on.

She turned me over, got my on my fours and started penetrating me from behind. I moaned and moved around in pleasure. I could not believe what I was doing and that a man was fucking me. She started moaning as she scratched my back. I was close to cumming but I did not want it to end. I felt so horny, so gay, so weird. I thought only about her dick in my ass, about sucking her, about being a good bottom. She then started moaning with pleasure and told me she was going to cum in my mouth. I first felt scared since it was all going too fast but I did not even have time to think of an answer before I was turned over as she ripped the condom and put her cock in my mouth. I felt the warm squirts of cum and I could taste it. It was very warm and some of it slipped down my throat as some started dripping from my mouth. She finished and separated and started jacking me off. I came quickly and just laid there on the motel bed with my cum in my stomach and her cum in my mouth and chest. She went inside the bathroom.

As I laid there I came to my senses. I was blinded with pleasure and alcohol and lost complete control of myself. I started feeling very weird and nervous. I had just been fucked! She came out handed me some tissues and told me she was going to go on foot.

I laid there thinking about what I had done... thinking that I was only going for a blowjob and finished getting fucked myself and swallowing cum. All my bicurious fantasies had come true in 1 night. That was going to be the beginning of a delightful journey of transexual sex for me and the catalyst for exploring my hottest and hidden sexual desires.

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