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Hookup : Men Reveal Their Most Embarrassing Sex Stories

(Photo Credits: Joshua McKnight from Pexels)

When you hear the word sex, there are plenty of adjectives you could use to describe it: messy for instance, hot, awkward, and sweaty. Hilarious is probably the last word you would use to describe it but you know unexpected things happen, and then there’s this: embarrassing. 

If you already experienced an embarrassing sexual encounter or two, all we can tell you is that it’s fine and if it’s any consolation, I think it’s safe to say that we’ve all been there. As a testament to this statement, here is a list of hilarious and embarrassing “getting walked in on moments” in bed as told by the gay men of Reddit.  

  1. Caught by a cop – this is probably more horrific than anything else, mind you. One of the commenters shared how a cop caught them having sex in a car but they told him, “Our parents didn’t allow us to be together so we had to resort to doing this.” The cop, who felt sorry for them, let them go. 
  2. Caught by the boyfriend’s brother and friends – the commenter shared how they were left alone at the apartment of his boyfriend’s brother while visiting. The couple was getting hot and heavy when the brother and his roommates along with their friends came back and caught them in the living room while he had his boyfriend’s cock in his mouth.
  3. Caught while orgasming – it was Halloween 2010 and the couple was getting their costumes ready but then things between them had gotten a little frisky. The thing is, the commenter’s boyfriend had a photographer roommate whose clients were mostly celebrities and some of them “came over for a Halloween evening.” Thinking that the couple is already out and on their way to West Hollywood, a visiting actress opened the door to their room to return a borrowed jacket just as they were climaxing. Needless to say, the actress ended up seeing their orgasm face. 
  4. Caught by the parents – the couple was horsing around after sharing a night full of passion. They were running around the house naked, giggling and screaming complete with hard-ons, when out of the blue the front door opened and in came one of the guy’s parents who dropped by for a visit. The boyfriend naturally ran back to the bedroom for cover while owner of the house could only tell his parents, “Ummmm we will just grab some shorts.”

What about you, guys? Do you have a “walk in on” moment in bed? What’s the most awkward or embarrassing thing that’s ever happened to you during sex? Share it with us in the comments section below!

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  1. Darrell1

    As a teen, my best friend and I were sucking each other in the bathroom. My brother and his brother very quietly got to the window and started watching us then began laughing.

    There went our secret

    • R L

      When caught, it’s hard to think of this, but didn’t it strike you odd that both of them would be peeping in a bathroom window? That’s the best defense when you’re being private and somebody snoops. “Tell on me, tell on yourself.”

  2. Maxocala

    This episode wasn’t embarrassing… nonetheless hilarious… and takes the notion of “I can make you come with one one finger” to the next level.
    I had an encounter with a 40something married man who lived an hour away but travelled to within a mile of me on business or to attend NFL games. Our first encounter was strained at best… as he was nervous and had anxiety over performance, premature ejaculation & cock size. This man is smoking hot- both dressed & undressed. I reassured him that I could care less about cock size or his ability to get hard… as long as he was having a good time. Well… not 2 minutes into our encounter he got off… then took his time getting me off orally. No complaints here…
    The following encounters were much more relaxed on his part as he realized that he wasn’t being judged… he could let loose a bit. On our 4th or 5th tryst we were lying naked in bed with him between my legs slowly sucking my cock. We learned if he got me off first he was good to go in seconds… The way we were positioned I was able to get a foot between his legs & my big toe found his hole. Within a minute he was grunting while sucking me & came hands free!
    While cleaning up I nonchalantly told him that “I can make you come with one toe…”

  3. MattK

    Age 23, in a car in an empty parking lot, clothes off, sucking a beautiful fellow 23-yr-old, then lights suddenly from behind and we can see it’s a cop approaching. We scramble to get our clothes on, have ourselves mostly covered but not entirely, when the cop comes to the drivers side window. Tells us we can’t hang out there. Doesn’t acknowledge what we had been up to, thankfully, and just tells us to move along. Embarrassing for sure; as a complete closet case then and now – very fortunate he didn’t do anything.

  4. Adam

    I met a hot top and we really hit it off and got the steam going. Unfortunately I had just recently had an outbreak of hemorrhoids which was embarrassing & painful but the worst part is I had also eaten a very poor diet that day so SPLAT all over him. So damn disturbing. Good thing we were both drunk & he was from out of town.

  5. Casanova Brown

    This dude I met and I were making out in the car in the park with the radio on. After we finished I tried to start the car but the battery was dead. This was about 2:00 in the a.m. I called my best friend who came and gave me a jump. After we got the car started my best friend informed me that he had the same dude in the same park about a week earlier.

  6. mike

    I was between the legs of a Adam4Adam member in his living room with his beautiful 9 inch cock in my mouth , when we heard a noise at the front door . His neighbor a 60’s something woman thought he was gone and had come over to make sure everything was ok . He hollered something , I opened my eyes with his cock buried in my throat and she and I locked eyes ,, She screamed and slammed the door and ran home ! We talked about it for a bit and I finished sucking him off !

  7. Jockn2cbt

    Blowing a guy forgetting I had a wad of gum in my mouth. Ended up in his pubes. BJ faux pax. The worst was messing around in my treehouse with a buddy in fifth grade. After a little frottage we were climbing diwn the ladder and I thought it’d be funny to drop my jeans. He laughed. Challenged him to a “sword” fight and the two of us were out in the open slapping dicks. Somewhere along the way, I made the decision that I had lost and that the loser was to be “executed”. Turned a nearby pumice block on end and presented the condemded laid out on the cold brick. I handed the victor a hoe and he made some convincing practice swings and woul lay the blade across the base of my cock and saw back and forth and was driving me crazy. It was just about then I catch something out of the corner of my eye, it’s my mom out pulling sheets off the clothesline with this horrified expression on her face. This time I knew I went too far. My father would be home soon, he would kill me and bury my body in the woods. Most of my disciplining just involved a don’t do that again and the belt would fly. Imagine when my dad sits me down and in about ten words tells me what I was doing today I should only do with girls. I was stunned. Years later I kinda start getting the idea my old man wasn’t the fag-hating mean old bastard he let the world see and that the PlayGirl mags under his bed I visited with some frequency weren’t for my mom’s benefit. He had to have had some stones buying those back then, guy buying PlayGirl….oh Biff I loved you so hard. The rest of his mags were couples having sex and just a couple years ago tracked down his long talked about air force buddy on facebook and the guy was in complete denial of even knowing my dad.

  8. Mike

    Lets face, sometimes getting fucked is more pleasurable than others. One of the times I was REALLY enjoying it, I forgot that I had eaten some blue raspberry licorice the night before. This fuck was spontaneous so I wasn’t able to plan. I was getting fucked from behind and it felt amazing and we were both enjoying it. We wanted to change positions so he pulled out. To my embarrassment it looked like there was a small serving of bright blue soft-serve ice cream on the head of his cock. Needless to say, the moment was ruined :-))

  9. MattK

    I have another one…sort of. As a closeted married (to my wife) guy, who’s gotten plenty of dick discreetly & safely over the years, I often wonder if I’ll ever find a guy on a4a or another site, who turns out to be a married friend or acquaintance of mine. Yikes! right? Mind you, I take “closeted” and “discreet” to the Nth degree always, but my thinking has always been, if we essentially were to “catch” one another seeking homosex, then we both have the same thing to lose, therefore, I don’t worry about it. That all said, for better or worse, it’s never happened…yet.

    • Hunter0500

      I’ve worked for two large local companies over the years. Am a member of a large church. Involved with a large school system. Involved with a large charity, too.

      I’ve encountered two guys from those. One we decided we weren’t play material. The other was at a play party some miles out of town. The guy was pretty far up the Management totem pole. We smiled at each other but kept our distance. We have seen each other in social situations since. We just smile and move on.

      As they say about honor among thieves…

    • Darrell

      That is my fear as well. But a year or so ago I made the same determination as you: if he and I are both seeking the same thing, then it’s our secret. I have run into sex partners in public places at times when I was with my wife. They never acknowledge me which has been a relief.

  10. Miguel

    Always wondered in my small town if I’d run into someone I knew. Yep, answered a CL ad and there at the door was a classmate from years before. He was married then, and his wife sometimes would peg him with a strap on. I asked if he wanted something bigger. It took a while, but he really enjoyed it. Sent me an email later to explain he asked his wife for a bigger one, but she already had a bigger dildo she used on herself but was afraid to try it on him. She’s keeping him satisfied now.

  11. Tom

    When local-boy-makes-good movie star the late Jan-Michael Vincent was the centerfold of an issue of Playgirl, I bought an issue of it as a joke for my mother’s birthday but really wanted it as jack-off material for myself. I had it in the bathroom during a period when they were out of town for the weekend but forgot to remove it before they came home. I paniced when I realized I’d left the magazine lying open on the counter. The magazine had disappeared, never to be seen again, and nothing was ever said about it. However, reading material was never kept in the family bathroom…, so…its “use” had to have been fairly obvious to my P’s !

  12. NotAnAngel

    During the Dark Days, I used to head to a bathhouse to get my rocks off and have a few loads in return. Back then, my profession frowned upon homos, although not so much anymore. I kept my business private.

    As I was going up the stairs, low and behold, a mostly naked colleague passed me. He didn’t recognize me. Cool, no fuss no muss. Wife, five or so kids, heavy stature, pretty famous locally…. and not for being bi or gay.

    In the private rooms area, things were hopping. There was a pretty good ass inside one door, upright, lube on the left, condoms on the right. Looked tasty. I made him moan with my tongue in his ass. Nice. I picked up a condom and was about to open it when he whispers: if you’re neg, just gimme a load. My hole’s hungry.

    I was. I shrugged and lubed up my cock. Nice. I sank in there in one nice long push as he groaned out loud. Wait a minute. I knew that voice. Uh oh.

    Suppressing the desire to laugh out load, I drilled that fucking ass. He loved it, and so did I. There had to be another load or two up there, making it all the more thrilling to add mine to his hot hole. And so I squirted it, far up his chute while choking his cock to his own orgasm. Mighty fine, that ass.

    He whispered loudly, “Thanks!” I answered, “You’re welcome, James.”

    The look on his face was priceless. Deep deep red was the color. “Oh fuck!!!” he said. Yep.

  13. Garfield

    In a gay chat room, I made a good friend who lived on the other side of the world. We sometimes jacked off together on cam with each other, but mostly just talked about stuff. He ended up marrying a guy here in North America, so I finally got to meet him in person a couple of times. The second time his husband was out of the country, and their marriage was falling apart, and my friend invited himself to my hotel room one night. We crawled in bed (clothed) to sleep, but then he started touching me, and eventually we ended up naked and kissing and fondling. At some point he lay on top of me (he’s somewhat smaller and lighter than I), and then we both fell asleep. Sometime later we woke up with him still lying on top of me. We had a good laugh, he got back on the other side of the bed, and we went back to sleep. So we didn’t actually have sex, and no one caught us, so maybe it wasn’t exactly embarrassing, but it was funny to both of us.

  14. Married

    A few years ago, I had set up an early morning project meeting with a colleague in a rural village 3 hours away. I booked a hotel in a city about 30 minutes from the rural village. This city just happened to have a bathhouse. I called the colleague, and asked him to dinner, but he declined telling me that he was staying in the small village because he had work to do prior to the morning meeting. I decided to go to the bathhouse. As I walked around the dimly lit bathhouse, I saw a shadow that was familiarly shaped like the colleague I was meeting in the morning. The shadow seemed to move quickly away from me each time I went towards him. I finally cornered this person outside hiding in a corner- he was the colleague I was meeting in the morning. We had an interesting conversation that evening. When we have met subsequently, he would always talk about his wife / son /family. He never mentioned the encounter ever again.

  15. cckscker65

    I was 14 or 15 years old and home alone. started masturbating in the livingroom to a mag that I got from a friend. Pants and underwear around my ankles. In walk my mother and sister. The embarrassment was horrific. I jumped up and ran to my bedroom and locked the door. Almost ran away that day. Needless to say it was never talked about.

  16. John

    An adult bookstore I frequented before it closed was where I’d go for mansex before the internet. The setup was a maze of booths with no doors so not much privacy. But the place was 30 miles from my home and I’d always hoped I wouldn’t encounter any guys I know even though we’re there for the same thing. The surprise I got was hearing a familiar female voice. It was a childhood neighbor girl. It was known she was the mistress of a prominent attorney. I’ll be damn there they were at this seedy place! I scooted out of there quick!

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