35 awkward moments that can happen during man-on-man sex
| 09/23/24
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Because awkward gay sex happens even to the best of us
Don’t get me wrong, I love having sex with men. I’m blessed with an innate ability to see the beauty in all men. (My friends call this being an undiscerning slut, but they just don’t understand me!) As someone who’s had more than his fair share of sex with men, I can safely say that there are tons of hilariously awkward things that happen during man-on-man sex. This post is a tribute to all those delightfully awkward gay sex occurrences. Enjoy!
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1. When he wants to film you
There's a time and a place for everything, and these days, especially with a rise in OnlyFans accounts, there are more people who want to "document" their sexual experiences. Not everyone is into this, but it's usually made awkward when the conversation opens with wanting to film, and dies if there isn't mutual interest. Not everyone has to see your sexual experience for you to still enjoy it!
2. When you get facial hair in your mouth while kissing
While I love a bearded man, I have to say I’m somewhat turned off when I get his hair stuck between my teeth. Sure, maybe I needed to floss, but that’s not what I’m going for when I’m smooching a bear with a hairy chin.
3. When you’re lying on top of each other, and your erect penises keep poking each other
Honestly, I think this has to be one of the funnier things about having a penis. While, of course, you can cross swords, you usually end up tucking them up, so you can comfortably cuddle together.
4. Beard-burn from kissing
It’s a thing! Your cheeks get red and tender after making out with a scruffy man. It’s the only con of dating a man who keeps a perpetual 5 o’clock shadow. Lotion is key for recovery.
5. When you orgasm within seconds of him touching you
He should be flattered. You were THAT turned on. Besides, that doesn’t mean you’re done with all the fun. Keep cuddling, making out, and focusing on him until you’re hard and ready to go again.
6. When you can’t get it up
On the flip side, there’s the issue of not being able to get hard – something that happens to the best of us. It can be really uncomfortable if you can't get hard, especially if you want to. Utilize this as a time to be kind to yourself, you're not the only one! Which brings us to...
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7. When he doesn't get hard
We’re all human, so don’t be rude if the guy you’re with can’t get a stiffy, especially if you have that issue every so often yourself. Take it as a compliment. It probably means he found you so hot that he got nervous. And not to sound like a broken record, but there’s plenty of other fun things you boys can do to each other without being hard. You both got hands and mouths, right?
8. When he’s just too tight
This usually happens when the guy isn’t really a bottom or hasn’t bottomed in a hot second. You’re both so horny and ready to go, but no matter how much lube is used, you just won’t fit. #sad
9. When you keep falling out
When the man isn’t super well-endowed, and the bottom is used to something a tad bit larger, the issue of “falling out” occurs. When this happens, let the top take control. He knows how big his member is and (should) know exactly how far he can penetrate without his peen sliding out.
10. When you get a little poop on your penis
We’ve all been there. It’s like, what do you expect? You’re poking around in a goddamn butthole. As the saying goes, you can’t roll around in the mud without expecting to get a little dirty. The only thing you can do is laugh together. This shouldn’t be taboo to discuss.
11. When you’re peeling yourself off him
Instead of cleaning up after a hot lovemaking session, you and your man decide to cuddle. Twenty minutes later when you try to change from big spoon to little spoon you realize you’re glued to one another, due to, ya know, semen.
12. When you’re looking into his eyes…
And you can’t remember for the life of you what the hell his name is even though he drunkenly told you four times at the bar. Thank god there are words like “baby,” “sexy,” and “daddy” we can say during sex.
13. When you run out of lube
You resort to using spit, which doesn’t cut it. Or if you’re really desperate, you head into the kitchen and find some olive oil. It makes a mess, but it’s so much better than boning dry.
14. When he’s too damn big
There’s big and then there’s BIG. God knows I have some size-queen friends who believe there’s no such thing as too big, and would kill for a 10-inch monster, but as for the rest of us who don’t like being impaled, a foot-long can prove problematic.
15. When he ruins the mood by playing with your Prince Albert or nipple ring
You just want to screw, but he’s too distracted flicking and playing with your rings. Or worse, he pulls on them way too hard as if they’re not connected to a very sensitive part of your body.
16. When you accidentally catch a load in your eye
Did you know this is actually a fetish? It’s called an “eye shot” and there are numerous porn vids dedicated to this. Oh, and by the way, you’re not fooling anyone by claiming you have pink eye.
17. You can’t find his hole
You’re poking around down there to no avail, and he’s just twiddling his thumbs waiting for you to find the spot. Eventually, if he’s nice, he’ll go ahead and gently guide your dick inside him. That’s when both you and him can finally experience paradise together.
18. When he looks nothing like his profile
So was that 15 years ago, or did you have a botched plastic surgery recently? I’m confused what catfishers think is going to happen when they actually meet up with a guy. We obviously see that you look nothing like your pictures. Are you just hoping we won’t say anything and instead sleep with you out of pity? Seriously, what do you think is going to happen here?
19. When you can’t finish no matter what
It’s amazing when you can last for long period of times, but not being able to finish is downright frustrating. After a jaw and two hand cramps, he finally gives up. Still, don’t forget that sex can still be incredible without “finishing” so to speak. That shouldn’t be your endgame during sex.
20. When you realize you’re both tops or bottoms
Wait, how did you get this far without realizing it? You’re going to have to pick straws to see who takes one for the team. (Just kidding...but not really...)
21. When you have to pee during sex
You can’t decide whether to hold it, ruin the moment by getting up to leave, or just pee on him. (Hopefully he’s into golden showers.) This is one of the many reasons you shouldn’t have sex hammered. Urination gets in the way.
22. When you want to bottom more than anything, but you have anal fissures
As gay men, we like to get our bussies torn up metaphorically...not literally. So when you have rough sex, or he’s too well-endowed, it can actually lead to fissures (which are little tears in/around your anus). They can be really damn painful, and when you get them, you have to cool it with sex for a while. P.S. You’re not alone! They’re a lot more common than ya think...
23. When you thought he brought the condoms
And realize right before you’re about to bone that neither of you have. So you put on a pair of sweat pants and frantically sprint over to the nearest CVS.
24. When you finish having sex and it smells a tad bit poopy
At this point, it doesn’t matter. You had sex and it was GOOD. But for the sake of enjoying the post-coital cuddle, it may be worth it to hop in the shower and light a candle or two.
25. When he pulls your chest hair too hard
Running your hands through a man’s chest hair? That’s hot. Pulling it lightly? Also hot. Yanking it to the point of severe pain (when that clearly isn’t your thing)? No. Shut it down.
26. When the condom breaks midway through
...and you don’t know how long it’s been ripped for.
27. When your sheets look like a ghost exploded
And you know you should wash them, but like, you just did three days ago, and you know they’re only going to get dirty again. Still, I guess, it’s good to be a hygienic adult and wash your sheets after both you and he jizz all over it.
28. When you orgasm unexpectedly
Sometimes an orgasm sneaks up on you and you climax unexpectedly, spraying everything and everyone within a 5-foot radius. No number of Kegel squeezes can stop all the semen from rushing out.
29. When you see a hickey on his neck
You know you shouldn’t care (unless, of course, you’re in a monogamous relationship), but you can’t help but wonder who was there before you. Like, was he cuter than you? Are they serious? Does he actual have a boyfriend and is cheating?
30. When you discover your hookup lied about his age
It’s weird how often people lie about their age. Some guys pretend to be younger, while others claim to be older. If you’re hot, you’re hot! As long as you're the legal age of consent, age really shouldn't matter. Be proud of how old (or young) you are.
31. When he bites too hard
Biting is hot. Who doesn’t love a good nibble on their neck? But biting to the point of OW is not sexy at all. It takes you out of the moment, and also makes you wonder if this guy has ever hooked up with anyone else before.
32. When you learned midway through he’s got some kinky fetishes
For me, this is always an unexpected surprise, and I love whenever he asks me to do something that I didn’t even know was a fetish. (I was once asked to “toe-f*ck” a guy. He also identified as a top, so there was a lot going on there.)
33. When he calls you the wrong name…
This has happened to me on a handful of occasions. It’s another one of those times where you just have to laugh. Besides, if you take casual sex too seriously, then it’s not casual at all, now is it?
34. When you learn he has a wife
I’m not talking about a polyamorous bisexual man. I’m taking about the “straight” guy who you meet in the locker room sauna who’s cheating on his wife. You can’t help but feel bad for both his wife (and him).
35. When he hands you his designated cleanup towel
We all have one – there’s nothing to be ashamed of. Although it is a slightly awkward (and unsanitary) if he hands you a towel where you can see the stains of all the men who came (literally) before you.
