I have had a lot of sex for myself with many different partners over the years. I’ve had two very serious, very intimate relationships with women, I’ve had some casual relationships with women, and extremely casual ones with men, and then there has been the sex with total strangers who I’ve met only once each, and barely known anything about.
The thing that fascinates me is the intimacy, or lack of intimacy of two strangers having sex with each other. I’ve never had a “classic” one night stand. The type where two folks meet in a bar, and fueled by booze find a passionate connection and go home with each other and shack up. Having never done that, I’ve always wondered how that happens and how it works. I’ve done lots of hooking up with strangers I’ve met online, and most of those times there is precious little intimacy even though we are actually as close as two humans can get to each other. There might be kissing, there is licking, there is sucking and there is fucking, but there is no connection, no bond, it’s just friction and body contact leading to orgasm, and that’s it.
Very occasionally I’ve stumbled into an experience where intimacy happened, or maybe a better word for it is connection. In these encounters I have met with men, or women with whom I hit it off physically and mentally even though few words are exchanged, and the experience is incredibly incredibly hot. In fact, arguably the single best sexual experience of my life happened with a women that I met through OKCupid. We only met once, and we were naked in bed together within 7 minutes of me being in the door. We then went on to spend an amazing and sex drenched night together where we literally fucked till dawn in every possible combination. We’d never met before or sadly since, but it was perfect, hot and amazing, mostly because there was a flow between us, no awkwardness, no reserve, just two people melting together.
Two other times happened with men, the most recent being the last man I met, which was just last week. In both cases I met these men randomly through Craigslist. The first guy I met while on a ski trip. We met up and proceeded to have an amazingly hot encounter with passion that I have only rarely seen in another man. We only had oral sex, but we touched, with kissed, we rolled in bed and shared a delicious intimacy even though we hardly talked and knew nothing of each other beyond what each could see of the other. With this man I felt warmth, I felt passion, I felt that we were sharing emotion even though we never spoke about it, and likely will never see each other ever again. There was warmth and understanding, and despite all that society might judge as wrong, there was beauty to the encounter.
This most recent encounter was kind of fascinating to me because it was a surreal mixture of intimacy and total emotional disconnection. The man had advertised for someone to come over for oral play. I had been really eager to give a blow job particularly for a long time with no luck hooking up, so this seemed like a perfect opportunity. I got to the guy’s house, and he was a decent looking guy with a decent house, and he invited me into his darkened living room where he had porn on the tv. We sat on the couch together, knees touching like only men who are about to have sex with each other do. Nearly simultaneously we reached for each others thighs and started to stroke. We had hardly spoken, had barely made eye contact, but here we were about to have sex with each other.
In short order his clothes were off, and then my clothes were off. Slowly however this went from a transactional sexual encounter into a passionate one. I’m not exactly sure how it happened, but I soon found myself locked into a hot embrace, each of us making frenzied movements and sounds like only hot sex provides. Again, we only had oral sex, but at one point he had me on my back and was dry humping me and I found myself really hungering for that ultimate connection of having him inside me. I enjoy anal sex with a decent partner, but occasionally I have been with men who really making me want it, make me hungry to take them in. This guy was one of those guys. He wasn’t a very skilled or confident lover, but he made up for that in well directed passion, and I’ll take that any day over the dull and lifeless fucks that you often run into.
But for all that passion and hotness while we were in action, as soon as each of us had cum, the magic was over. With the first guy I described, I felt a sort of euphoria and kind of didn’t want the encounter to stop. With this guy, once the cum spell was broken, the magic was over, and we “came to our senses” and went back to being two dudes who were strangers. While I relished the actual passion that we shared, the post climax was kind of a let down and was mildly disconcerting.
I obviously am really ok with sex with strangers, and sex without intimacy, but I have to say that its a lot more fun when it is intimate. It’s just puzzling to me how detached men can be and how difficult it is to find a partner, of either gender, who you can really be intimate and connected with.
Post Modern Curious Man: 1 Man's Misadventures 
