Dancing with a Tranny: A First Experience

I never thought about the reverse effects of fucking a crossdresser. She was beautiful, very womanly body, shapely, petite at 5ft7in and only 130 lbs. Dani was incredibly beautiful with long brunette hair past her shoulders. She always dressed sexy too. I was 15, horny as hell and wanting someone to fuck. I tried to fuck two of my cousins but that only ended up with me rubbing their pussies and them rubbing my cock not even a handjob. I knew that Dani was making herself available to some of the local boys, but much older, 18 plus. I tried to go out of my way to help her when I saw her working on something in her yard, or carrying groceries etc. She'd often bend over in her mini skirts and I could see her pantie covered behind. One day she went to the bathroom and came out in only a robe. I could see she had stockings on. "You know what I am right Charlie?" she asked. I asked what she meant, and she said that she was a woman, but was born with a cock. She asked again "You know that right?". Yes maam replied. So why do you help her all the time, you've become a staple around her, I'm not sure what I'd do without your help. She offered to pay me if I wanted, and I told her no. I was about to tell her, that I wanted her, sex with her even though I knew she didn't have a pussy. It took probably 15 or 20 minutes and I shot my second load up her butthole. I was in teen boy heaven. "Did you like me baby?" she asked "YES, YES" I answered. As she was moaning she moved my hand down to what was now a hard cock about 5 inches long. She reached over and got something and I felt cold on my butt. She was lubing me up. "What are you doing?" I asked her. She was lubing me up"You dont' want to do it without lube baby, trust me""do what?""What?"

I was still not fully getting it. I wanted to fuck, not get fucked. "Just hold it there" she told me. I was on my stomach and she got on top of me her cockhead at my butthole. "No, don't please, . . . please?" I asked her. It was too late, I had 5 inches of cock inside me all the way. Her landing strip of hair I could feel pressed up against my ass cheeks. "Hold still baby, get used to it, eventually you'll love it". I asked her if she did this to the other men who came over. "Only one guy, he shouldn't have married a woman anyway, but none of the others, this is just you and me. I made you feel good, you make me feel good." With that she was pumping she lasted about 20 minutes talking to me about how good I felt, how she hoped she made me feel this good. "Did you like doing it to me like this" she asked. I told her I did. "It will be over soon baby,"

Sex stories

Did you like this story? Dancing with a Tranny: A First Experience look, but like these, here Sex stories.