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Sex with my best friend

806 words | 6 |4.20

My transgender friend and I had sex after I caught her dad and boyfriend fucking

My best friend growing up (David) was always rather flamboyant. Even at 9 or 10 it was very noticeable. We had always fooled around, as young boys sometimes do. I’ll show you mine if you show me yours kinds of things. We slept at each others house almost every weekend and always slept in the same bed and always in only our tighty whiteys. Never thought anything wrong of it. I grew up in a religious home but my mother didn’t have any objections to me having a flamboyant friend whose Dad was gay. Maybe she thought he was flamboyant because he was being raised by a gay couple, I dont know.

One particular night, lying David’s bed, we were 14 at the time, I felt his leg rub against mine. When it happened a second and third time I realized it was intentional. It lead to us kissing first without, then with tongues, but only went as far as him giving me a hand job. The next morning I left before he woke up feeling embarrassed and stupid. My dad taught me to be manly and tough, so why was I letting another boy jack me off?

I distanced myself from David for a few years after that night. It wasn’t until I turned 18 and was going off to college that I thought to reconnect with him, or at least apologize for everything.

I went to his house, his Dad answered the door and I could tell by his reaction to seeing me that my spontaneous arrival was a welcomed one.

It had been 4 years since I last was there. David’s Dad grabbed my bicep and in a flirtatious tone said “You’ve sure grown into this body”. I humored him by smiling and saying thanks. He casually pointed me toward the basement door as if to say David was down there. “We remodeled the entire basement” he said as he closed the door behind me. They had completely remodeled it so that David had everything except a shower down there.

I knocked on the bedroom door and entered before he could say come in, and what I saw shocked me more than anything ever has. David was transitioning to a woman. A rather beautiful one at that. She changed her name to Jasmine, had long black hair, make up was perfectly in place, and was wearing a tight little skirt, nylons, knee high boots, and a white tank top. I was blown away! She had next to nothing for breasts but still looked good. She was just as blown away to see me as well. We shared an awkward hug, I apologized, and we spent the entire evening catching up.

I admit, I was very attracted to her but the memory of how I felt 4 years ago still lingered. We talked so long that night had come and she asked me to stay the night. I reluctantly agreed.

I was taking a shower before bed and as I exited the upstairs bathroom I noticed her Dad’s bedroom door was cracked open. I had to walk by anyways, and when I did I peaked in and saw her Dad and his boyfriend having sex. Words cannot describe how quickly and hard my dick got! Wearing just a towel, my growing erection undid the towel and it fell to the floor. I picked it up and began making my way to the basement. Why did that turn me on so much? Does it mean I’m gay? A whirlwind of thoughts and emotions went thru my head. As I walked back in Jasmine’s room, she was laying bed under the covers, but noticeably naked. With everything going on in my head I didint realize I too was naked and still rock hard. I wanted sex so bad at that point I’d have screwed anything at that point. I crawled into her bed and immediately our tongues twisted together. Before I knew it she went under the covers and began sucking my raging hard on. Just when i thought I couldn’t take anymore she crawled out and straddled me. My cock in her hand she guided my cock in her tight petite ass. She started riding me faster and faster. Before I could say anything she said “I’m going to cum!” She then sprayed an entire load all over my stomach. She climbed off and started licking it all up. Every last drop. When she was done she kissed me long and hard. Drops of her cum still in her mouth, and taste of it turned me on even more! She got on all fours and began fucking her again. I’ve never came that hard in my entire life. We’ve both moved on in our lives relationship wise but we still get together once or twice a month and fuck like rabbits.

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  • Reply Jamie69 ID:1749916zj

    Love to taste some cum

  • Reply Jamie69 ID:1749916zj


  • Reply Peter ID:1cdjao7zfik

    Thanks for posting your story I really enjoyed it

  • Reply Jack ID:3zxjrywcqrd

    Now I’m cumming

  • Reply Shorthy ID:61jyxp5hj

    I had a friend like that when I was in my 20’s. I fucked her a number of times. Then o e night we got drunk and s.oked some good weed. We were both horny and she was real hard. I’d sucked her a few times, but this time she told me she was going to fuck me. I had been fucked before and the thought of her fucking me really turned me on . She fucked me good.

  • Reply Bill ID:9cg6p942

    Damn! So awesome