My first sex was with a much older tranny - but . . .
I never thought about the reverse effects of fucking a crossdresser. She was beautiful, very womanly body, shapely, petite at 5ft 7in 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 I replied. So why do you help me 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 I still knew that men with men fucked in their butts and mouths and I wanted sex! But as I was screwing up the nerve her back doorbell rang. I overheard her "I can't now Tim, I have a young man her, he's helping me around the house OK baby?" The door shut and she came back. I asked who it was and she told me. She had sex with a few men that snuck around to her back door. Some teens, some older men who were married but wanted what she would do for them. "What do you do? I mean if their married don't they have what they want with their wives?" I asked. She told me that in most of the young guys they just wanted relief, but the married men wanted what sometimes wives wouldn't do for their husbands - blowjobs, swallowing, and buttsex.
"So they come here and you do that for them?"
"Oh yes, I love sex"
"So you do it for them in your mouth? In your butt?"
"Indeed I do, I just love being fucked. You see to me, I'm a woman, that's what I feel and act like"
With that she opened her robe, she was wearing black see through panties, bra and garter with black stockings and high heels. I looked at her panties and didn't see a bulge.
"Where is your. . ."
"It's here, just tucked between my legs, I like to look like a woman in all ways"
With that she took me by the hand and we went to her bedroom. She pulled down the panties and sat on the edge of the bed while she undressed me. She took my cock in her mouth and I was in heaven. I came probably within 5 minutes and she swallowed it all. "That was a lot of cum for one young man. You tasted so good baby, I loved it". I lain back on the bed. She leaned to me kissing me, pulling my hand to her small B cup tits. She leaned over and put one in my mouth and I was sucking like man. I reached down and was feeling her ass, putting my hand down the crack. Kissing me again, she broke off. "Looks like someone is ready again" point to my cock. She got on top of me and rode my cock. I could see her small cock now but I was finally fucking someone. 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 you just did to me"
"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 asscheeks. "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,"
She came pushing up inside me as far as she could. She was done. "Whew, I don't do that often but you are so young and so pretty. You can come and have sex with me as often as you want now, ok? We don't ahve to do that everytime, but sometimes I just need to. Is that OK?" I told her it was. With that She sucked me hard and this time missionary let me fuck her again.
I thought about it for a few days, she yelled at me from her back yard sometimes but I didn't respond. Finally one evening I went over. She sucked me, I fucked her twice, and she had me give her a blowjob and swallow. Since I go back probably 5 times a week, always cum two or three times. It's only about once a week I suck her cock, and maybe every two weeks I have to let her fuck me. But I got sex from a beautiful tranny.
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Comments (1)
Kenny: My first time with a trans was so exciting so erotic I fell in love with her
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