first time with a Tranny

My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits. We dated for about a month when talk her into just taking her shirt off, after a while without her shirt off she finally took her bra off. I would make out with her and suck on her tits, lick her nipples. One day we were together I decide to change it up so I took my pants off in the bedroom and walked out to the living room where she was at watching t.v. I don't wear underwear so my cock was hanging around, it was semi-hard. She saw it and gasp because she never saw a cock in real life before. I had to calm her down and we sat there and watch t.v. together I wanted her to get use seeing a cock. Couple days later we were in my car, just got off from work heading back to my place. We stopped at a light and she told me to go behind this building that was not in business anymore. So I went in the back and she surprise me by unzipping my pants and pulling out my cock. She wanted to touch sense she saw it and she started to stroke it. She was doing a good job stroking my cock and I told her to put her mouth on my cock and suck me off. She took a while but she put her head down there and started to suck on it. Bobbing her head up and down, my cock hard as a rock. She did it for 20 min. before I loaded my cum right in her mouth. She jumped up with some cum on her lip she opened the car down and spit the cum out. First time for all, she was a virgin well so was I. She told me if she ever suck my cock again warn her so she can be ready. So weeks went by and now at that time she love giving head, when I ask if I can eat her pussy out (still didn't know about her cock) she would tell me maybe next time then she would suck my cock more. Every time I ask I get a blowjob, by that time she was a pro doing it now. After dating her for about 2 1/2 months, she finally broke down and started to cry and she told me she didn't have a pussy. Of course I thought she was joking but when she pulled down her pants and panties and saw she had a cock, I was very shock. I went into my bedroom and thought about it while she was in the living room still crying. I asked her to come in the bedroom, she comes in and try to talk but had no clue what she was saying though all that crying. So I told her I was in here thinking about it and well you are a very beautiful woman and we don't have to tell anyone about this. She ask what I meant by that. I laid her down on the bed and started to kiss her on her lips, she was puzzled about that. I took off my clothes, and I told her I don't care you have two out of three holes to have fun in. I slowly took her pants off and then pulled her panties off. She was laying there half naked, her cock was about 4 in. long hard. I stroked it and she started to feel better about her self now. She sat up and took her shirt and bra off and we started to make out. She went and sucked on my cock for a few min. and I went and sucked on her cock for the first time. The I told her to lay on her stomach and I got up and got some Vaseline came back on put some on her ass. She jumped and wasn't sure if she wanted to do it yet. I laid down on top of her and rubbed my cock on her butt-hole but she kept trying to push me off. I sucked on her neck and she liked that and I slowly and carefully put my cock in her ass. She jumped again and ask my not to put it in, but I eased it in more. She told me to stop because it was hurting her, I took her hands and held them down and going up and down on here, I was only half way in. She try to break free of my hold, I went all in and she screamed in pain. I went slowly pumping her ass, while she started to cry. Then I let go of her hands and started to pound her ass, she started to moan more than crying. She finally stop crying and she was moaning real loud. She was telling me to fuck her harder. I was pounding her so hard I thought the bed was going to break, orgasm after orgasm. I fucked her for an hour and half before I came inside of her. I told her after I got off of her at least I can't get you pregnant. She laughed and said yeah, and she laid there and went to sl**p. We did brake up about a year later, I had a friend over who was a female, she was a BBW with C cup tits and I was in the middle of fucking her when she walked in and saw me. She stormed out pissed, I kept going fucking that nice warm pussy and came inside of her. Then I went and try to talk to her. I told her I needed some pussy too, but she told me to fuck off and have fun fucking fat woman. After she left I went back to the other woman she was about to get dressed and I told her no and laid her down on her stomach and fucked her up her ass and she loved it.
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Categories: AnalShemales
Posted by theho_1
3 years ago    Views: 4,435
Comments (8)
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8 months ago
Kinda of awkward but great story lol.
2 years ago
ha ha, nice
3 years ago
Great story!
3 years ago
Bravo! :D
3 years ago
Interesting
3 years ago
Good Story, Better Attitude.
jacquin001
retired
3 years ago
YES THE FIRST TIME IS ALWAYS THE BEST THAKS
3 years ago
Haha wtf