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Describe in detail up to 5 of your most memorable or best hookups and explain why
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Describe up to 5 of your most memorable hookups and explain why they stood out to you. It's ok if you only have one story to share.

I'm a 30yr old bi top and most of my memorable experiences were with twinks and one was with a woman. Over the last decade I've had hundreds of hookups, many with twinks. I can remember maybe 20 to 30 of them if I sit down and think hard.

I can't really rank any one of them as number one as it would be like comparing apples and oranges so in no particular order:

  1. So I was on vacation in Florida and started talking to a cute 19yr old Latino twink. He was my ideal twink. Since he didn't have a car, I paid about $60 to have an Uber bring him to my place and back. Best money I ever spent. When he got on my bed, I asked him if he was on PreP which he said yes, then asked if he wants to bareback and he agreed. I got very excited because at the time I hadn't barebacked with that many guys before.

As I stick my dick in his hole in missionary position it felt like complete heaven. Was one of the best bareback experiences I ever had. Every position we did felt so amazing. I came inside him twice. After we finished, I offered him a dark chocolate in the kitchen, he did this thing where we split the chocolate with our teeth until we kissed which I thought was really cute. We ended up making some sex tapes that I still watch from time to time.

  1. I hooked up with another cute twink in Florida, same age. He also didn't have a car so I paid for an Uber to bring him to my place. When we finally met, I couldn't believe that I was going to get to hookup with this guy. His cute face and smile, and his slight lisp when saying certain words. We end up fucking and he just looked amazing in every position. My dick was a bit sore before the sex due to some friction injury, but it still felt good. We also made some sex tapes, I really liked the angles.

  2. I visited a swinger's village where straight couples are known to hookup with other couples and single men. I rented an airbnb and my neighbors were a Spanish couple in their 30s or 40s. Every time I'd go inside my apartment, they'd usually be there to greet me. I was a bit shy so I would only make short conversation. I wasn't sure if the woman was really interested in me or just being polite.

Then on the last night of my stay I noticed that she sprang up to talk me, I could tell right then that she was into me. So we arranged to meet later that night after they went out to a bar. Her husband came back really drunk and eventually sat on a chair passed out on the patio. She was also drunk but not as much. Inside she had her hands all over me and began unzipping my jeans. She got on her knees and sucked my cock really well. We got on the bed and I started fucking her doggy style. It felt like complete heaven, then after a while the condom completely broke except for the base and the pleasure increased by 20 to 30%. I didn't notice it at first until pulling out. We ended up deciding to continue fucking bareback.

My favorite was when she was riding on top of me and I would thrust my dick inside her pussy. Eventually, since we didn't fully close the door to the patio, a random single guy shows up to watch. I ignore him initially but eventually it started to make my boner go down so I told him to leave. After that it took me a while to relax and get hard again but she was very understanding and patient.

After I came on her the first time, she was so into me that she kept wanting more of my dick. So after some time she managed to get me hard again and we went for round two. We probably fucked for like 30 to 40 minutes. It was late at night when I went back to my apartment. As I'm laying in my bed I could still feel wave after wave of pleasure on my dick as if the experience was still going. It wasn't the first time I ever barebacked with a woman, but it was the first time I barebacked with a hot woman.

4. I had a blowjob experience with a twink that felt like one of the best I ever experienced. Basically a cute twink I hooked up with before was really horny one night after drinking. So horny that he began unzipping my jeans as I was making the short drive to my place. He pulled my cock out through the hole of the zipper and began to suck. It felt incredible, his lips were so soft and his mouth warm. I don't know why but having it done while driving felt so much better than on a bed.

  1. This was a hookup from a longer time ago, back when I was 23 or 24 and still capable of bottoming. While on vacation in Florida I met a super cute 18yr old twink who was only a top. He looked like he could be a model. I decided to let him fuck me. I was super relaxed and happy that day. As I got on my knees and took off his pants, he had a huge dick, nearly horse sized. I could only fit some of it in my mouth but it was so hot.

He starts to fuck me in missionary position and we were both surprised by how easily I took his dick. I think it helped that I was living completely in the present moment and fully relaxed. I got fucked like a pro bottom and it was the best experience I had as a bottom, just wave after wave of pleasure, but sometimes his dick would go too deep and hit a wall inside my rectum which hurt a bit when it happened but overall an amazing experience.


More recently, I've been thinking about getting back into bottoming to change things up as I've been a top for years but first I have to deal with my IBS, an anal warts breakout, and some other issues.

So yeah I'd say those are my top 5 though I'd say I have some more than that. A cute twink sucking my cock on the beach and when I had a short relationship with a guy and we fucked bareback on the beach.

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