I've always been straight, always had girlfriends, never was attracted to or thought of anything besides that either. In a relationship I was in a long term one a few years back she wasn't as sexually energetic as I was. I felt as if sex wasn't as frequent as it should be. She wasn't cheating either we were always together when we weren't at work. So I started drinking a little much around this time and would jerk off quite often. I had never before watched tranny porn but stumbled across some and it really turned me on. Like badly turned me on. A lot actually. So I started frequently visiting tranny hook up sites trying to find a local one to meet. Not just any raggedy one she had to be attractive obviously. I started talking to one in particular but when it was time to meet I got scared and backed out. Fast forward a few months later the sex life still wasn't what I wanted it to be with my girlfriend at the time. So I was going to get an escort, something I never did either. Craigslist was still good at the time and I was like I'm definitely not gonna pay this money for something given the effort I can get for free essentially. That's when I clicked on TS escorts. Let's just say I found one I was very interested in, after much debate with myself I called her. Well texted at first and set up a time during work where I could meet her. I show up and got nervous my believing I made it this far. I was parked out front and thought I was gonna drive away when I called instead saying I was here. She came to the front and opened the door, wow.. even better than the pictures. I followed her up to her apartment and she shut the door. Here's some small background she really didn't have much of tits, she wasn't a post op, she did have prettt long hair to almost middle of the back, she was some type of Spanish but more of an Italian skin complexion, she had beautiful lips and a pretty face, she was thin but had a very cute tight looking bubble ass. Her legs were very cleanly shaved too. When I got there she had on this little skirt with stockings halfway up her thigs and like a very tight corset strapless top. So with that said after she shut the door she asked if this was my first time which it honestly was and I said yes. She asked if I ever was with someone like her before I said yes cause it really was. She said OK don't be nervous money on the table and I put the money on the table. I guess awkwardly I just stood there and she said that it was ok I shouldn't be nervous that need to just relax. She told me to take off my shirt and I started to unbutton it. She came over and took it off me and ran her hands all over my chest. She said it's ok you can touch me you know right? Hesitant still she came into kiss me, it seemed only natural then I kiss back. That's when I finally did start to touch her, wrapping my arms around her thin waist eventually grabbing at her ass and legs. She said come on, come to the room. So I followed her to this mattress on the floor in another room and she told me to take my pants off and lay down. I did, she comes down to the mattress and starts jerking me off then starts to give me a blowjob. Before her this was easily the best blowjob I ever received hands down. She was truly incredible at sucking dick, knew exactly what felt good. I was hoping to cum but she stopped and said do you wanna fuck me now? I said yes, so she told me to get up and I did, we kissed again standing on this mattress and then she broke away and got on her hands and knees, she pushed her skirt up and started to finger her ass. She instructed me to spit on it and I did and stared rubbing my dick around her hole. Not too long after I was fucking my first tranny. Her moans were ridiculous it was so fucking hot, I never got to fuck a girl anally before and even though this wasn't a true girl it was still fucking great. I loved fucking her like really fucking loved fucking her. When I came in her ass it felt like I never came before that. I ended up visiting her 2 more times down the road. I ended up meeting a different tranny escort off Craigslist who had really nice tits but we didn't fuck I just got a blowjob and she kissed me when I lied and said I never been with a tranny before. Since then though it's been back to strictly girls. Lately though I've been really wanting to fuck a tranny again, badly. Fuck you all who wanna talk shit, I'm not gay I love pussy, I just like to fuck I wouldn't fuck a dude who looks like a dude and isn't a tranny. I just think it's hot and taboo.

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