With all the transgender talk in the news lately, I decided it might be fun to date a tranny. Why not? I’m open minded, even a bit freaky. Have you seen some of the shemales on the Internet or any of those online tranny sites? Gorgeous. A pretty face, nice rack, and a huge cock? Tell me that is not a wet dream right there. I perused all the local ads and called only one. May, a beautiful bi racial tranny with a nice cock. I didn’t mind paying for the pleasure of her company, because the combination of that face with that cock, told me the pleasure would be all mine.
I picked May up at a local hotel as she was just in town for a week. Guess it was a good thing she did not live local or I may go bankrupt. The moment I laid eyes on her my pussy got wet. We had a nice dinner, surprisingly great conversation before she invited me back to her hotel room for some sexy shemale chat. I knew that was code for fucking. We were barely in the door when I had my body pressed up against her dark caramel skin groping at her nice sized cock. She kissed me hard and deep. I swear I came in my panties from her tongue probing my mouth.
May took charge. I was not her first rodeo. She went down and ate my pussy until I squirted all over her face. I of course went down on her tranny dick. Took every inch of her thick shaft in my mouth. She had to slow me down for fear she would blast a hole in the back of my throat from the jet stream of jizz. I showed May my ample cocksucking skills. It was really nice to be able to have a huge cock fill up my mouth while I played with a nice set of tits. I was a bit jealous. Her rack was bigger than mine.
After she could not take it anymore, she bent over and fucked my ass. As soon as she stuck her cock up my back door she apologized. I’m an anal whore, so I had no problem with her sticking it up my butt. I guess she is use to fucking guys! Her big cum filled balls fucked my hot ass good. We switched positions at one point and I got on top and rode her pretty dick reverse cowgirl. May pumped a hell of a lot of spunk up my ass. I’m not going to lie. She was one of the best fucks I have ever had. It was worth every penny I spent.
If you have never fucked a tranny, you have no idea what you are missing. A sexy shemale like May, really is the best of both worlds.























As soon as I met Erica I could feel the attraction between us. She was one hot bitch. All though there are times when I enjoy a good roleplay that calls for me to be a dominant tranny, most of the time I am submissive. When Erica walked in the room her dominance seeped from her pours and you could almost smell it in the air. My body responded instantly to it and I had to meet her. I continued to mingle until I saw her talking to a casual acquaintance across the room. A sissy that I had known for a long time that hadn’t decided if she wanted to actually have transgender surgery or just live as a sissy. Saul was in her Sally persona and seemed to be coyly flirting with this stunning beauty. I felt a pang of jealousy as I made my way across the room towards them. Sally embraced me and introduced us right off. I felt a shiver run up my spine when Erica looked me up and down. As the night wore on and the drink flowed more freely, the flirting became more intense and eventually I invited Erica back to my place. It didn’t take me long to discover that she was a sissy trainer and that she figured since I had a dick and lived as a woman that I must be a sissy and she was going to train me. There is a big difference between a tranny, even a submissive one and a sissy. I don’t know if it was the alcohol or if I was actually offended, but I felt challenged in a way. When I excused myself to “get more comfortable” for the evening, I decided to slip into my dominant roll. Needless to say it was a very interesting evening….
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