I guess it would have to be my first with a transsexual. She was an escort and was drop dead gorgeous. I was very nervous, but she put me at ease and after 20 minutes of chatting she leaned over and kissed me and before I knew it I was sucking her cock. We wound up 69 and eventually jerking off and cumming on each other's clocks. I saw her 2-3 times a year and eventually had her cum in my mouth and fucked me.
Two ladyboys in Bangkok. One fucking my ass while the other fucked my mouth. They both came on my face…. Way fun… I also had sex with a female to male trans that was fun too.
My Ex and I were at a park and things got pretty hot. A little caressing and petting working my way to rubbing her pussy. We almost fucked right there but too many people started walking around the park. We went back to my apartment, we kissed and lifted her up on my counter where I devoured her sweet pussy. We ended up sucking and fucking on my bed. One of the hottest sex sessions I've ever had.
Didn't happen in bed, but on my big comfy leather recliner. Had my lovely wife sit back while I took off her cute socks and kissed nibbled and sucked her red painted toes which makes her crazy hot. Soon had her pull down her skinny jeans and slid them off. More toe sucking and kissing her feet, squeezing her calves getting her even hotter. Hooked my thumbs in her panties and slid them off. Pussy was very juicy and she loved being fingered whilst I reached for a small butt plug with a vibe built into it.
Licking her and slipping the plug slowly into her perfectly beautiful arsehole. Worked it in and around and as she threw her head back in pleasure I slid it out and saw it was just a little dirty. Rubbed it's head against her arse then had her get up on her knees so I could lick and suck and tongue kiss her musky little hole. Won't lie, there was a very little bit of brown on the toy and her hole.
I loved sucking her and the toy too.
In my senior year in highschool, which was my third school since my parents got divorced and I moved out with my mom and we moved again at the start of my senior year. I had to make up a math class and was the only senior in this class. I sat next to this little cutie who was a sophomore. She invited me to her house within the first week of school. We went right to her bedroom and fucked. In the middle of fucking her mom walked in the room and said oops, I didn't realize you were doing homework. I was startled and had rolled off Jamie and her mom looked straight at my dick and smiled at me and said she'd like to talk to me when we were done, and walked out of the room. I said shit we are busted. Jamie said don't worry mom does not care. So we finished and I got dressed and went out to the living room. Her mom was there and she looked pretty hot for a mom I thought. To make a long story short she asked if I had fun, I was like, uh yeah sure. She said she could show me even more fun if I liked. Took me to her bedroom, sucked my dick and then let me fuck her ass. My first anal. I loved it. I fucked them both for a few months until I met another girl who I fell in love with.
Fisted my friends Moms pussy , after that I had her deep throat me & swallow
It had to be that night my Bull-dyke bitch GF and I ass fucked some 21 year old Bi-Sub named K. with strap- ons ......( Thunder Buns )
I've fucked with my brother, many times, without protection and knowingly taking the risk of getting pregnant. We didn't do that often, but sometimes we were too horny to wait. Getting pregnant for my brothers baby would had made the hell break loose. That's one kinky thing I've done.
I have fucked a vase. The history of this vase is extremely fucked up. Our neighbor was an old man. We didn't knew what child m****ter was. I think even he didn't knew what it was. But our parents warned us to to not to hang around with him but never told us why. To us he seemed to not to be right on the head, but otherwise he was kind and harmless. He never forced us to do anything. Seriosly thinking, I think it was us who were abusing him more than he was abusing us. Our cousin, couple years older, was more raunchy and sexually "experienced" and he asked him to buy us smokes, candy and even new porn magazines. She sometimes let him touch her and few times even rode against his dick or knee, but both of them having clothes on. He had showed us that he had porn magazines, but that was the only really bad thing he did. We were secretly visiting him every now and then because we didn't want our parents to stop us.
One of those times when my brother were not with us, our cousin suggested him to stick his cock into that vase and then fuck it in his bed. We were watching him humping it, laying on his stomach and bare ass pumping up and down, He came inside that vase and we could see the liquid in it and my cousin always put it back on the shelf. To me, it was just funny to get him to do it but I think my cousin were horny.
Many years later he died. He had no family, and our dad, who was taking care of the apartment building, had to open the door and empty his house. Nobody claimed his stuff and they were too cheap to cover any expenses, so some of his more useful stuff like furnitures were given to charity and church took care of the other expences. But nobody needs vases, and because I knew its history and now it made me horny, I took it.
It is now sitting in my bookshelf, having plastic flower to keep it from collecting dust, and inside, it still has the all the smudges of all of his dried sperm in it. He might have cum ten times in it and never cleaned it and for over thirty years now, everything is still sitting there. It is quite thin, like his cock was, and I can push it inside me with lube. I've done it couple of times when I was reliving the memories of him fucking it and wondering how we would fuck now but I'm too afraid to do it, to not to break it.
