Have You Ever: Had Sex On A Roof?

gay sex on a roof, Out in Public, Tristan Jaxx

Back when I was living in New York, older men would often try to lure me onto their rooftops for a sexual rendezvous or two. It's the type of thing your mother would warn you about, as she lectured you on the dangers of meeting strangers in such locations. In other words, it was something I was especially prone to do. I mean, when have I ever listened to anything my mother's advice?

With that said, it probably goes without saying that I've had sex on a roof. The hottest time occurred after my very first invite, with a painter who we'll refer to as "Paul". You see, Paul wasn't the most attractive man in terms of facial features, but he looked like he had a decent body and I couldn't pass up the thrill of fucking on a roof. So we wound up meeting.

You know how I said he had a decent body? Turns out it was utterly amazing. You could tell he was doing his squats, because his thighs and butt were huge and solid. After slamming my cock down his throat with no mercy, I buried my tongue in those muscle cheeks. He moaned so loud that I was sure people on the street heard him.

Then it happened. This beefy hulk of a man–who was nearly twice my size–begged me to give him a thorough pounding. And who was I to turn down his request? I bent him over the side of the building and thrusted away until he shot a thick load all over the place. Then I pulled out, threw off the condom and exploded so far that even I was impressed. A few drops may have even flown over the edge, and I distinctly remember laughing at the thought of them hitting some passerby in the face… Surprise facial!

And there I go yet again boring you with my stories! If any of you have ever had sex on a roof, we'd love to hear about your experiences. In my next bout of public sex thrill-seeking, I'll be trying to convince a certain someone to bend over during a little hiking trip. Wish me luck, because I'm looking forward to sharing more tales with you!

– Dewitt

Photo credit: Out In Public

To check out these guys in some rooftop action, follow the JUMP:
















Picture 79

Picture 77


19 thoughts on “Have You Ever: Had Sex On A Roof?

  1. First off, it is quite often that when a person is involved in unplanned random sex will end up doing it bareback. After all who carries condoms in their man purse?
    Back to the topic, I fucked a guy on the roof once. I was 19 by then and was part of the moving crew in Boston. The owner who was in his 30’s took me to the roof and ended up fucking him. I was wicked nervous feeling like probably everyone else was watching. Well, that was back then.

  2. Hot Damn, This Tristan better be paid by this guppie for sex.
    This guppie better be twenty-one.
    Looks too young for me to fool around with.
    Nope, no sex on the roof on my part.

  3. @tresqboy:
    1) What does that first paragraph have to do with the topic at hand?
    2) What do rooftops have to do with unplanned sex?
    3) I always try to keep condoms and lube with me (unless I don’t have any loose pockets for it), just in case.
    Anyway, I haven’t had sex per se on a rooftop, but I did do a little nude sunbathing/jerking off on the roof of the physics building as an undergrad.

  4. like, i have lots of bare sex and even *I* carry around condoms and lube in my jacket… not having the with you isn’t much of an excuse, it’s not like they take up lots of space… if they do just run around with insertive condoms 🙂

  5. walking around with condoms…eh…too skanky. though I guess most gays think nothing of screwing random strangers out of nowhere.

  6. @furfriend
    According to the original poster (Dewitt), it is safe to make an assumption that the meeting was merely random. And we all know that most of the time, folks are pretty much unprepared when it comes to the unplanned sex, which quite often the will lead to bareback sex.
    Still, having sex with strangers without condoms, a person is taking a major risk in his life. But on the other hand, carrying condoms in your man purse, wandering around the block preying for strangers, makes a person a slut. Either way you are stuck in the paradox.

  7. Did everything on the roof top ( lots of 4 play ) but we where 2 nervous 2 go all the way ….. BTW whats with all carry condoms & lube N your pockets like lose change I mean I do not BARE BACK EVER but the whole idea of carrying condom & lube every time I go out the door just seems 2 be so promiscuous

  8. I mean I kind of fail to see how carrying a condom around’s slutty or promiscuous. I’m in college and I know I personally carry a condom around in my wallet. Mind you, it’s not like a roll of ’em and I don’t carry around lube, but like it’s not bad at all. I know a bunch of people who do it too.

  9. By the way, it is NEVER a good idea to always store condoms in your pocket/wallet. The constant heat and friction break them down, increasing the chance for failure.
    Short-term is ok.

  10. Based on what appears here most in wallet would be short term. Further more, from Dewtt’s alleged stories his appear to only make them out the door till used. But I could be wrong and have misread all his sex tales portrayed here.

  11. Everyone’s entitled to his opinion. Personally, I think carrying around condoms is being smart, not slutty. For the record, I haven’t used mine yet (haven’t had sex anywhere there weren’t already condoms), but I still like to know that I have them, just in case the opportunity does come up. You can’t always rely on Trojan Man showing up in the nick of time.
    The hard part is trying to figure out where to keep them in the summer, when I don’t have a loose jacket pocket or something to keep them in.

  12. And tresqboy, re-reading the article, I can see how it could be read as random, unplanned sex. I still think it’s equally valid that he was talking about pre-arranged hook-ups, however. Especially with the sentence, “So we wound up meeting.”
    At any rate, I’m sorry for berating your apparent off-topicness. We cool? 🙂

  13. i agree with all the posters saying carrying condoms are good.
    whats wrong with being prepared for anything

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