Most Embarrassing Sex Moments

[Rooker]

I predict this will quickly devolve into a series of humble brags and erotic fiction, but in a trying to keep things light around here.

Make us chuckle at an embarrassing (as an adult) moment of intimacy.

I broke up with a gf and foolishly stayed close to her. The breakup itself was quick and respectful on both parts, and handled well, initially. We had vastly different interests and after the initial month, I didn’t see us together long term. So I told her I didn’t think we were right for each other long term and she agreed.

Buuuuut, then it got a bit rough. I should have cut the cord but responded to her messages and in retrospect, was leading her on. I won’t go too far down that rabbit hole, but I was genuinely worried for her safety.

One Saturday, I foolishly went to her apartment on some (her) pretense of lending her a hammer or something. No entendre intended. I was actively dating and while there was nobody serious, I had a date that night. Well, my libido took over and my ex and I started going at it pretty hard, but I stayed dressed.

I’ll spare too many details, but she started grinding on me so much I did something I had never done, came in my shorts. She went to get me a sandwich and played it off like she didn’t know. They were a fucking mess. Luckily I had a gym bag in my jeep so I changed while she was at the takeout restaurant.

She came back, I fixed her counter, and then left.

Later, as her late night calls subsided, I got the hunch that it was her way of closing the book on our relationship and getting the upper hand.

Well played, ex from April of 2018.

 

[notthatguy]

Having sex in the confessional booth at church. The girl had some serious issues with god... even worse she would scream "oh god" over and over again while orgasming..

 

[latinluva]

Two things, first one was with a girl in the back of my car. I hadn't had an orgasm in three weeks. I was just so busy and tired from college athletics practice. I pulled her panties down ready for doggy style, shoved my cock in her wet latina pussy, gave her about four to five strokes really deep.....and busted a nut all over her ass. That was the only time I ever came that fast.

Second, I was sucking a mans cock in the adult video arcade. It was a gloryhole. HE had the biggest cumshot I had ever seen. Cum was flying ever where. When I thought I had cleaned myself up, I had left the booth area. As I walked towards the front door, two females were looking at the magazines and as they glanced over at me they had a look of shock and then started laughing at me. When I double checked myself in the car, I had a string of cum hanging from my goatee chin area and a big glob still on my shoulder, of course I was wearing a black shirt.

 

[halcyondays]

I've shared this one before. Well after midnight on a hot summer night a college girlfriend/fiancee was riding me hot and heavy by the light of the TV in their family room when her younger sister walked in on us. I wasn't paying attention but when she heard the door open my girlfriend jumped off of me to hide behind the couch but squeezed me so tightly I came. Her sister watched wide eyed while my cock fountained come. I was soooo embarrassed.

A couple years after we split I got a call from my ex's sister asking to relight the hot water heater at her apartment. While showing me her bedroom on the nickel tour she took off all her clothes standing by the bed. I took off mine. So began one of the hottest secret affairs I ever had. It lasted until she found a new boyfriend.

 

[Kinglmao]

I got pink eye after I ate this dudes ass.

 

[deleted25278651]

Ex girlfriends dad caught us fucking lol it was definitely an experience

 

[lapdog2001]

I think my most embarrassing sex moment was likely the first time I ever experienced premature ejaculation. It had never been an issue for me ever so it took me by complete surprise when I started to cum after only fucking my girlfriend for a minute or so. She didn't mind and even said I must of been so turned on that I couldn't hold back! Fortunately, 10 minutes later I was able to give her the proper (much longer) fuck that was our normal!

 

[stretch8888]

I was late 20s, in a relationship that was on the rocks, we were fighting more than anything. I had a good friends bachelor party to go to on a Friday night, something i'd had planned for MONTHS, week before she says she made plans for us, i say i can't because of my plans, she gets pissy and gives me the silent treatment the whole week.

Night of bachelor party i start getting texts/pics from an old friend with benefits who i'd had a long term affair with in my mid 20s, she was recently divorced, a little drunks, VERY horny and desperately wanted me to come fuck her, as much as i was interested, i had no way of getting to her as we were in the city.

The following night my GF was still giving me the silent treatment, after a few drinks i call up the FWB, she is a little hesitant and says we really shouldn't but i want it and with very little convincing, she tells me to pick her up at her parents farm, i pick her up, she tells me to find us somewhere to fuck and while i drive she leans over and starts giving me head, i find a dead end we'd used countless times, i head over to the passenger side and she is waiting, legs spread and i grab a condom from the glove box, she stops me and says "i'm a single woman now, you don't need that", i warn her i might not last long as it had been a week, she says she's sure i'll be fine, she guides me in and it feels like heaven, then wraps her legs around me and pulls me in quick, it happened so fast i couldn't help it and just unloaded inside her, i was embarrassed, she giggled but said she was kind of flattered she could make me cum that quick given how long i usually lasted, she didn't mind though, gave me head and we went for round two

 

[BobbyDick10]

very hard on nudist beach

 

[elklindoxxx]

One time when we were with another couple, for the first time. They were a younger couple and the guy was walking around with an erection that didn't go down. He was really excited and was all over my partner. After some foreplay, my partner was ready. As she was giving the guy a light hand job to put the condom on.... and...the guy ejaculated. And rather impressively as well.

He was embarrassed and my partner is understanding, because it happens on occasion. Apparently this fellow was so excited, shortly after, they were able to have intercourse. Without another premature ejaculation....

 

[Kinglmao]

Lowkey now that I think about it I probably should’ve been embarrassed more in some of my hookups but tbh I can’t remember some of them now . But oh well. I’m glad you guys are sharing because it actually helps me feel better to know a lot of us have gone through things like this . I thought I was just trash lol

 

[tomj77]

In college, I shared a nice townhouse with two other guys. Our landlord owned about six of these townhouses on our block. Surprisingly for three college guys we were pretty neat and tidy so she would use our townhouse as the “show house” for perspective renters. Usually she would call and let us know she was bringing someone by. One afternoon I got home from class, figured I had the place to myself and started stroking it. I didn’t see the light on the answering machine so I missed her message. About 5 minutes into my solo session, she popped the door to my bedroom open and saw me going at it. I had my headphone on and eyes closed so it took a minute for me to realize she was there. She slowly backed out and closed the door. And she apologized through the closed door. I was so embarrassed. I threw on some shorts and quickly cleaned the place up. She brought two pretty cute girls in on a tour about 15 minutes later. She was cool about it later. I think she may have been more embarrassed than me. A few weeks later she made a joke about penis size when I dropped off the rent, so I figured she must have been impressed.

 

[Kevyn7x6]

I was banging a GF after a day of surfing,
Missionary,
My nose drained snot water onto her eye balls

 

[chrisrobin]

The young man I got propositioned by this morning in a local loo. He was stroking his hard cock, nice round end so I offered my services, as one does. On my knees to give him a blow job to came off as soon as I closed my lips, his warm spunk just shot out and I just about manged to swallow it. He looed embarrassed, tucked his cock way and there was a hammering at the door and a womans voice saying "David, whats keeping you" - his mum!

 

[nomju]

Oh, and the time we were at a music festival. We were in our tent and my gf (now my wife) was on her knees blowing me, when our friend burst into our tent exclaiming 'Motorhead are on soon, are you coming'.
If I'd been more quick whitted in might have said 'Im not coming yet', but we just told them to fuck off.

 

[nomju]

The first house I bought was just around the corner from my mum and dad, and my mum would often pop round to clean my filthy bachelor pad. I didn't mind. Less for me to do.
Anyhow I'd got a new girlfriend (my future wife). Before meeting her I'd booked a guys only skiing holiday. The morning of my flight out, my hot new girlfriend called round to say goodbye. We were vigorously saying goodbye, on the living room sofa when my mum let herself in, so she could say goodbye.
My mum had never even caught me wanking before that day, so to find me balls deep in my new gf was a bit of a shock.
She ran out screaming 'Im sorry, I'm sorry'.
Funny part is, after the holiday I popped round to see my mum and dad, and while I was alone with my dad he leant over and whispered 'Your mum told me about the day you flew out. I hope she didn't put you off your stride.'

 

[User101823]

A Grindr hookup: a very tall, very hung young dude (early to mid 20’s) showed up. I thought I was just giving him head. He immediately took off all of his clothes, then all of mine, and then started to kiss me standing up. Then he began rubbing our cocks together. This went on for quite some time, to the point it got boring because he just kept repeating the same motions over and over (both kissing and rubbing). Finally, he asked me to get on the bed and lay down because he wanted to suck my dick. So I did. The moment my dick hit the back of his throat, he looked up with this strange expression on his face, then he just opened his mouth, and vomited all over my dick and balls. Then, he looked right at me and asked, “do you want me to keep going?”

I was shocked. I told him, “no, we have to clean this up.” I ran into the shower. He stayed in the bedroom. When I returned, I told him to go wash out his mouth and wash his face, and I took the comforter off the bed, and put it in one of those black plastic industrial bags, then told him this had all been a mood killer.

He didn’t want to leave, and still wanted to continue. I actually had difficulty getting him to leave. So bizarre!

 

[Vastian]

Had a good friend he used to come over every day and we would watch anime and play games. We really enjoyed the same stuff. We also used to screw all the time. He was a petite African American male. In great shape. More lean than buff. Amazing lips. And a 8 inch think cock. Cut. It also looked amazing aside from the size. And no leg hair. Really he was the whole package. I always bottomed for him and it was great. One day I asked to top. He agreed. His ass was smooth and tight. (He was my best friend..keep this in min) I came in like 20 seconds. And he turned to me and said that's it? I was devastated. ...still worth it though... been a full time bottom since then