I was fucking this dude I met on grindr in his bedroom, next to the door. He asked me not to cum inside his ass, so as soon as I was ready to cum I took my dick out of him. I masturbated for a while and when I finally came, his husband (I had no idea he was married) came into the room, getting my cum all over his clothes. He was a very nice guy and he understood my side, but he got really mad at his unfaithful man.
Most awkward sexual experience...
- Thread starter Kosmic
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Got a chance with a girl I had long fancied. I came in about three strokes. She actually gave me a second go to do better. I improved and lasted perhaps a half dozen strokes.
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- 80% Straight, 20% Gay
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We were out in the country at dusk parked on a quiet road, our clothes off and made out until she was wet and I was throbbing hard. I ate her pussy for a while then she gave me a blow job. As she said, "I want you so bad" I was getting on her and absolutely sprayed cum everywhere. She didn't say a word, didn't need to. Her pussy was great and that day the anticipation and her stroking it before I could attempt fucking her caused cum to fly onto the seat, her pussy and belly. I was very young so a few minutes later we fucked. She had the most beautiful pussy and a perfect amount of black curly hair. Yummy
I got two,
1. hookingup with a woman and mid sex her 12 year old daughter comes home and starts just pounding the crap out of the door, her aunt lived next door and knew that mom needed alone time lol.
2. A lady was in an open marriage and told me after popping my dick out of her mouth that we had to be quiet fucking in the living room because her husband was in bed....her female roommate wanted seconds too(she wouldn't share) but the husband in the next room thing was too much for me...I feel like if I knew him and he gave me the green light it would have been less unnerving.
1. hookingup with a woman and mid sex her 12 year old daughter comes home and starts just pounding the crap out of the door, her aunt lived next door and knew that mom needed alone time lol.
2. A lady was in an open marriage and told me after popping my dick out of her mouth that we had to be quiet fucking in the living room because her husband was in bed....her female roommate wanted seconds too(she wouldn't share) but the husband in the next room thing was too much for me...I feel like if I knew him and he gave me the green light it would have been less unnerving.
Wait, I'm not finished lol I have a third.....
She met me at a disc golf course and we decided to get busy in the woods behind one of the back holes. Well,I had her bent over a tree stump the poor thing just started to bleed all over me. She was so embarrassed we got totally eaten by mosquitos too. I wasn't upset she was fun but after that I never heard from her again.
She met me at a disc golf course and we decided to get busy in the woods behind one of the back holes. Well,I had her bent over a tree stump the poor thing just started to bleed all over me. She was so embarrassed we got totally eaten by mosquitos too. I wasn't upset she was fun but after that I never heard from her again.
The more I think about the more I recollect a catelogue of historical awkward sexual encounters/incidents. Hard to say which was the most embarrassing and/or uncomfortable.
In addition to the two incidents I have already posted about I have to give (dis)honourable mention to the time I had successfully chatted up a woman at a party but before we had departed for somewhere more private a drunk guy decided to flash her and the other ladies in the room. She laughed at him and made a comment about how he thought anyone would be impressed with his tiny dick.
It was on the small side but he was still significantly bigger than me.
I was just a tad trepidatious about her seeing my much tinier penis so tried to engineer it so we were in a darkened room. Thought I had managed this but she decided to switch on a lamp and her facial expression when she saw my teeny cock looked like a cross between surprise and disappointment.
Still had the sex but my poor performance was equally unimpressive.
In addition to the two incidents I have already posted about I have to give (dis)honourable mention to the time I had successfully chatted up a woman at a party but before we had departed for somewhere more private a drunk guy decided to flash her and the other ladies in the room. She laughed at him and made a comment about how he thought anyone would be impressed with his tiny dick.
It was on the small side but he was still significantly bigger than me.
I was just a tad trepidatious about her seeing my much tinier penis so tried to engineer it so we were in a darkened room. Thought I had managed this but she decided to switch on a lamp and her facial expression when she saw my teeny cock looked like a cross between surprise and disappointment.
Still had the sex but my poor performance was equally unimpressive.
Most awkward would be a petite young lady who decided she needed my cock- no argument there. I'm above average but not huge, and we tried all sorts of foreplay to get things working- which it was, just not with me inside her. Anyway, with some gentle insertion and lubing I managed to get inside, and after repeatedly being told to relax, was going along well. I looked down and there was blood, not just a little bit. When she noticed it she burst into tears, jumped off me and dressed in a hurry. I was left bloodied and wondering quite what I'd done, not into blood or pain.
I didn't hear from her for a few days but she turned up at my place again, looking very embarrassed but keen once she saw I was OK with her.
Never happened again and we never discussed it- had no need- she was a great lover
I didn't hear from her for a few days but she turned up at my place again, looking very embarrassed but keen once she saw I was OK with her.
Never happened again and we never discussed it- had no need- she was a great lover
Hahah dude it’s not funny when it happens to you .... lol
Unfortunately, I’m used to pulling out and the condom being a little dirty. The bottoms freak out but I tell them, “all good ... shit happens”. Usually laugh and clean up and usually have fun in the shower. Worst was a dude and we were fucking for about 2 hours and finally getting ready to nut when I feel pressure. I’m thinking ok he’s having another anal orgasm ... pulled out a little too far and he actually shit. All I could say was, “oh shit!”. He tried to stop it but couldn’t. I had to stop myself from laughing cause I didn’t want to make him feel bad. He was def embarrassed but helped him clean up to show I wasn’t freaked out or mad. Never heard from him again tho ... lol
A few weeks ago I was breeding a bottom and even though he was super clean (flushed till clear water came out) we had been going for so long you know it stirred up something inside. Like you, I felt something push against my cock. I left it in him for a second and let him know he needed to clean up. Lucky for me the shit on my cock wasn't that bad and was a quick clean up. Better than the guy who was "cleaned out" and it came out brown after 3 thrusts.
Within a few months of getting married, my wife and I were having sex. I was kneeling between her legs and had her feet on my shoulders penetrating her as deeply as I could. We both seemed to be enjoying things and I noticed that she felt REALLY slippery. I thought, "wow, she's into it" and felt even more excited by the act.
When I pulled out, my cock was coated in blood - she'd started her period. I hadn't experienced any intercourse during menstruation up to that point and I did cringe seeing the mess. My shock/disappointment lasted all of 5 seconds. LOL
When I pulled out, my cock was coated in blood - she'd started her period. I hadn't experienced any intercourse during menstruation up to that point and I did cringe seeing the mess. My shock/disappointment lasted all of 5 seconds. LOL
I won’t say how young I was when a willing girl had a crush on me. My best friend at the time had fucked her a few times and told me he was sure she would do me as well.
The following weekend we were in the woods together and I was encountering no resistance. I had never seen a naked girl before and it was all very exciting. I had always wanted to go down on a girl - I imagined it being the best tasting thing on the planet. When I saw that little triangular patch down by her crotch I couldn’t help myself - I lifted her legs up high and dove in. It tasted, well, like shit. It was nasty and I was disappointed. It never occurred to me that I had gone too far down. All was not lost however- I did get laid for my first time.
I never said a word about her pussy being the most foul tasting thing I could imagine. However, she did. My friends teased me relentlessly about missing her pussy and eating her ass instead.
The following weekend we were in the woods together and I was encountering no resistance. I had never seen a naked girl before and it was all very exciting. I had always wanted to go down on a girl - I imagined it being the best tasting thing on the planet. When I saw that little triangular patch down by her crotch I couldn’t help myself - I lifted her legs up high and dove in. It tasted, well, like shit. It was nasty and I was disappointed. It never occurred to me that I had gone too far down. All was not lost however- I did get laid for my first time.
I never said a word about her pussy being the most foul tasting thing I could imagine. However, she did. My friends teased me relentlessly about missing her pussy and eating her ass instead.
