Share Your Fun and/or Interesting Sexcapades

[MaybeMaybeNot]

I thought it would be fun to hear of any interesting or fun sexcapades from years past, anything unique that was hot or fun that really happened. As someone who lost his virginity at 32 and took it slow (and was scared of getting outed by another gay man), I missed out on a lot of fun opportunities to connect and cum. So, help me live vicariously through you (and entertain us all through this isolation).

 

Perhaps you had a hot hook up with someone and then ran into that person later. Maybe you stumbled onto your buddy jerking off. Maybe you had a good friend who you started sleeping with. Maybe you had a great roll in the sack with your Uber driver, hotel clerk, or your professor in college. Perhaps you had a surprise threesome. Share the details of how it happened (like, what led to you to get naked with a platonic friend), what you did, and what the aftermath was (like, did you remain friends or run into the hotel clerk again).

 

I don't really have any exciting stories of my own because I played it cautious for too long. I do have one from a former suck buddy, and he had a story I always found fascinating. I'll tell you about him, us, and his story.

 

My buddy "Mark" (about 13 years older than I am) was a great closeted sub cocksucker. He loved to kiss and took instructions on sucking dick very well. He liked to make me feel good, and I could tell him how to vary his technique throughout our time together. He always made sure I came at least twice, often three times. He was closeted, loved to be sub, and loved cum. He was Catholic (it was very disconcerting to be stripping and rolling around in his bed with a picture of Jesus staring down at me--he eventually replaced it) and had permanently separated from his wife because they didn't believe in divorce. He had two adult daughters whom he was crazy about.

 

Mark had a group of drinking buddies; they were all blue collar and would go out drinking together throughout the week. After his divorce, one of his buddies moved in with him. It turns out his buddy was closeted gay as well. They never had sex together, but sometimes when I'd come over, he'd grab his roommates porn and put it on for us. At first, I always insisted the roommate be gone when I came, and he would go drink the garage. Then I regretted starting that because I wanted to see him. It would have been hot to say hello to the guy, him knowing what we were up to. One night while I was over, the roommate had walked home from a nearby bar drunk. At Mark's instruction, we stopped moving. In the dark hallway, the drunk roommate walked right past us butt naked and hard in Mark's room. He didn't see us, and unfortunately, I couldn't see him.

 

Mark lived about 45 minutes away from me, but we managed to connect every few months over the course of four years. He lived in a smaller, farther out suburb from our city. He had been hooking up with a guy in another farther out town (we'll call it "Darwin") who loved to kiss and cuddle naked for hours like me, but he had stopped hanging out with him.

 

Before we connected, I had also met a hot guy in Darwin (also about 45 minutes from me). "Nick" was younger than I was by about four years, and he was in a wheelchair. He couldn't feel anything from the waste down. But, holy cow, we had a connection. In fact, the first time we got together, it was the first Craigslist hook-up where I didn't feel disgusting afterwards. We flirted and kissed, and he enjoyed sucking my dick. And we kissed a lot. Leaving after two hours was always disappointing. I wanted to stay in bed with him for hours. I stopped coming over when he started dating someone.

 

At some point, Nick broke it off with his boyfriend, and I started having fun with Nick again. (Truthfully, I probably could have really had something with Nick. The chemistry was intense, but I was so closeted and in denial.) He really wanted a husband, and when he started pushing it (to the point that his friend was going to be over any minute, and we were both still naked and he was pleading with me not to go), I felt it was better for both of us to stop it. I just didn't want to hurt him and knew that I was not available to be what he wanted.

 

I realized later that Mark and Nick had been hooking up as well. The intense connection I had with Mark and the very intense connection I had with Nick, we all shared together. What happened was that after Nick broke up with his boyfriend, he had posted on Craiglist looking for me, using my fake email name. Mark saw, replied because he also knew my fake email name, and they realized who the other was. It was surreal to realize we all had this amazing sexual connection together (even though all three of us never met together). Mark stopped seeing Nick for the same reason I did, because Nick really wanted a husband. And, Nick got his husband! I Facebook stalk both Mark and Nick periodically and toy with the idea of friending them. (Two years ago, I finally faced the truth that I was gay, was born gay, and was never going to be attracted to or able to have sex with a woman. I'm only out to a couple people, but it would be good to connect with them.)

 

Anyway, the sexy story with Mark is that he would always check Craigslist throughout the week. One day, he saw something unusual, someone posting from his small town. He replied, and the responding email had one of his married drinking buddy's name on it. Mark revealed who he was, and the two started hooking up secretly once a month. He had been attracted to this buddy ("I always wondered what he looked like naked"), and he not only got to see him naked, he got to suck his dick on a regular basis. I would have tried to initiate a threesome, but I don't fool around with married guys. After I moved across country, his buddy was the only one who would make out with him (his other regulars, who were all married, would only get a bow job from him). I email with Mark periodically to check in (he always just responds, "Everything is fine here. I don't know what else to say."), and the last I heard, he's still hanging out with his drinking buddies and sucking one of them once a month.

[+ poolboy48220]

I was at the bar with four friends. We struck up a conversation with two guys and found out they were part of the traveling troupe for "Ragtime" playing in town. Lots of flirting & touching, and we all headed back to my place to continue drinking. One of my friends and one of the actors headed upstairs immediately, the rest of us stayed downstairs drinking, until my friend came back downstairs and told the other actor "I need to see you naked right now". That set it off; one friend undressed the dancer and started sucking his cock and I moved behind to rim the dancer. We all moved upstairs, paired off, me with another friend, a little furry bear. We all ended up back in my spare bedroom watching the second dancer fuck my friend who'd been blowing him. All this to the tune of Ricky Martin...

 

That's the only time ANYTHING like that has happened to me.

[+ poolboy48220]

One more (and I only have a few more). I'd gone to the bar after seeing the first Tobey Maguire Spider-Man movie (so 2002-ish?) This cute twink with shaggy dark hair who kind of looked like Tobey, but barely looked 20, started flirting with me; very unusual for 40-ish me. I bought him a drink, and when we were waiting at the bar for our second, he took my hand and put it down the front of his pants. I don't think we finished that drink, I asked him to come home, and he said okay if I promised to drive him home, since he'd come with friends. We were all over each other as soon as we walked in the door, I rimmed him bent over the couch, and we headed upstairs. When I took his shirt off I was surprised, happily, to see a lovely furry chest; like @Mo Mason 's signature, I find "Furry young men are otterly adorable." At one point he was sitting on my cock and I asked him to put his hands behind his head so I could feel his furry armpits. We ended up not coming that night, it was late and too tired (well, I was probably too tired, he was young and probably could have gone all night) so we went to sleep. I woke up first and slid over to him and while he was still asleep, started rubbing my cock against his ass. I reached around and he was rock hard; either morning wood or the frotting was turning him on. I'm not sure if he was even awake yet when I started fucking him, but we did finally come then. We showered and dressed (and he'd apparently never felt a hand-held shower spraying his balls from underneath). I dropped him off on the way to my nephew's first communion. He didn't give me his number but said he and his friends would be at some bar later that night if I wanted to meet up, and to this day I kick myself for not taking him up on that.

Edited April 17, 2020 by poolboy48220

[+ Axiom2001]

I came out to two of my very good friends while at an approved after-hours club in San Francisco. A hot tune was being played by the DJ. I encouraged myself to get up to dance, and dance--dance I did. Later that same summer, I went to the Nob Hill Theatre on Bush Street (closed in 2018 or 19). While I viewed Boys in the Sand, one scene got to me big time. The setting was Fire Island, and a few friends had gathered in one of the summer rentals. In one hot scene, there was lots of fucking and sucking. At one point, this gorgeous actor (whose name I've forgotten) sat in a chair and sucked on a banana. To date, I keenly remember something going in and out of a hole but can't vividly recall the specifics. The scene was so intense that I blew a huge load in my undershorts and shuddered. At the end of this flick, I left and walked up Bush Street with the most visible and quite obvious wet spot on my pants. ...felt euphoric and mighty good yet intensely embarrassing.

 

While at The Barracks or another venue which offered all-out sex-- I walked upstairs and wandered around the glory holes. At one point, an older man neared me and offered me five dollars. I cordially shrugged him away. After a while, he approached me again and attempted to entice me again. This time a hot feeling stirred from within and beckoned my body to oblige his offering. I ventured inside the cubicle, took out my eight turgid uncut inches and placed them inside the nice sized, carved out hole. The man on the other side gently knelt and removed his teeth from his willing mouth while inviting "my gift" into his oral cavity where he sucked so, so fuckin' gloriously. That mighty mouth had me standing tiptoed in an aura of so much fuckin' ecstasy. That mighty talented cock sucker had me in one hell of a frenzy that I almost became light-headed. After the copious explosion- I gently pulled out of my recipient who had just received all of my thick, sweet, white nectar and left the cubicle in one hell of disbelief, for I had never had such expertise giving me what I had long yearned, and to this very day, I have yet to have found any man who possessed the pleasure that this man yielded.

 

For about five years, there was an escort in San Francisco who had one hell of a talented mouth. He kept my nips aflame and sucked cock with such aplomb. Unfortunately, he retired from the profession about two years ago and is gainfully employed in another field which he immensely enjoys. He and I are Facebook amigos. At times I yearn for his mouth and recount memories of the past.

Edited April 22, 2020 by Axiom2001