This is a porn site (obviously) and there's plenty of content to get off to so, I want to hear about those times that fucking just didn't work out quite the way you wanted it to. Whether it was painful, funny or plain mortifying let's talk about it because sex at some point was new and awkward for us all! I'll go first.

I'll set the stage real quick. One night, years ago, I made some bomb dinner for my girlfriend (super nachos to be exact) and, because I am true to my beaner heritage of making food heedlessly spicy, I garnished our dinner with freshly diced habanero peppers. I'm sure you can guess where this is going aha.
Dinner was ready and set before my hungry beauty but I made her wait a bit longer to cut up the peppers and sprinkled them lil shits all over like a gourmet chef (I like to be dramatic, sue me). Obviously she loved it and once finished we wanted to do the dirty and my smart ass didn't think to wash my hands after handling such dangerous utensils.
I lubed up my dick and while the lube didn't protect either of us from what happened next, I do believe it prolonged the process resulting in my poor girlfriend also suffering from my life choices that night. Next, I did some clit play with the head of my dick to tease her for a moment then I slid my shaft in, right to the base. We probably had only been fucking for 3-5 minutes before she stopped with a look of confusion and said something like, "my pussy is kind of burning hold up" and I immediately said, wait what, followed by a shock of horror and fear as I realized my mistake.
Backing away from her as a peculiar warmth was also beginning in my own penis, I gently explained what happened to the discombobulated woman before me. What followed has haunted my dreams and ensured I would never again forget to wash my hands after handling spicy, well, anything. In the matter of seconds, the warmth grew to an intense burning sensation that spread over my entire head and shaft. No amount of soap or water could diminish it for at least 45 minutes (give or take a few as it felt like an eternity in my head). Although I can assure you I did not suffer the worst fate that night, no fucking way. While I don't possess a vagina, Lady, my love, described the experience for me and I can't imagine. She said that it began from inside her pussy, which felt like someone might have been shoving a red hot metal pole up her and twisting it about. Then she explained, it felt like flames engulfed her labia and pussy lips moving outward.

Sounds awful right? God I am so glad we can look back and laugh about it now.. And no lasting effects/damages on either of us so after the initiate "what tf were you thinking" it was really no harm, no foul. There's my shame story though, I'll post Lady's story later but let's hear yours next!

 

Had a rather calamitous situation that comes to mind
Ex gf was riding me while I was sat on the toilet seat
She got carried away and leant on the towel rail and pulled the entire thing off the wall
So mid fuck I stood up forgetting she was attached to me and she slipped off my cock and hit her head in the bath
I couldn't help her for laughing

 

My ex dislocated my arm during sex. I was riding him reverse cowgirl, leaning forward with my hands on the bed, and for who knows what fucking reason, he swung his leg out and took out my arm and dislocated it. I fell onto the bed screaming, and he yanked me up and popped my arm back into place. We aren’t together anymore and this is one of the many reasons why lol.

 

The number one reason why I always want the panties or thong OFF - not just pulled to the side.

I was banging an old GH for the longest time with her thong just pulled to the side - well it must have slipped right back into her crack. I didn't notice for a little while after we were done, but my cock felt tender, and by the time I got up the next day, I had a full blown rash up one side and it hurt for days.

 

Biggest fail was when I got in bed with this girl and she wasn't there, WTF!

 

One time me and a ex where both really drunk we where on a trip at a casino after drinking a lot and gambling we went to care hotel room. We started having sex she was on top riding me when out of no where she blew chunks all over me all over the king size bed every where. Smelled like cheap beer and casino buffet food

 

We were fucking in a tent, heard noise in camp, thought it was a bear, coitus stillinsideus till the bear became a friend who showed up middle of the night

 

Was doing it in the car when we were in college and a cop showed up. Thank his he let us off with a warning.

 

I was giving a dude a BJ and in the middle of performing, I felt nauseated (it wasn't my gag reflex) and had to run to the bathroom to throw up -I have no idea what came over me lol. Just glad I didn't do it all over him...glad he was cool with it but it did ruin the mood.

 

In highschool I was out with a guy. We had fucked, then sucked each other. Well he wanted to fuck my ass. I told him no that I always had a enama before anal sex. He just wouldn't take no for an answer . I relented and he fucked my ass. When he pulled out his load followed by quite a bit more came with it.
Glad I wasnt around when he explained to his dad why the car smelled of shit.

 

My wife and o were fucking really hard on a plastic deck chair. She was on top of me pounding away when the damn chair gave way! Crashed under us. At first I thought she broke her arm. Thankfully no. But the laughter killed the mood but not the fun!

 

I had an experience like greeneyedg1rl.
Drank much too much 'Jungle Juice'. Took his dick in my mouth and started fellating him.
Vomited kool-aid and everclear.........profusely.......... all over his lap.

 

Had a Mustang hatchback. Got busy in the back and when my hand reached her prize I felt the string. She said that she’d understand if I wasn’t into redwings. I pulled the blood plug out and flung it out the open hatch and did the deed. When finished and driving out the park I looked into the rear view mirror. Stuck to the back glass was the bloody plug. That was pretty fucked up.

 

My most mortifying moment was crying after orgasm, my first fuck with an unexperienced guy.

He was super rough and I orgasmed hard in doggy. He misunderstood my goosebumps for being cold and my cumming sounds for pain. So he wrapped me in the covers and held me. I don't know why, but the intense happiness made me cry. He started apologizing..
I considered telling him everything was ok and I was just happy. But I was too embarrassed. So I pushed him away, called him an idiot, slapped him in the face, then got dressed and left

 

Wife and I had a particularly good round of fucking and I had her sit on my face to clean her up and keep things going. She always cums hard when we do this and there was no exception this time either . She came hard, lost her grip on the headboard and flipped over backwards. She flew off the side of the bed, head first (the back of her head) and smacked the carpeted floor with a sickening thud. Knocked her out cold for a few seconds. I thought I killed her. Right away thinking how the fuck am I going to explain this? She had an appointment with the chiropractor with a couple of.....awkward questions to answer the following day.

 

Tell them the truth - they never believe a word you say anyway.

 

I realise I have had a boring life when I read these kinds of threads.
The closest I've cum to something like this was when was invited to bed by a lovely young lady I'd spent the evening with. Needless to say I went willingly. Once in bed I realised how much she had actually had to drink by her inept behaviour so I faked ED and hugged instead. It didn't take her long at all to dose off. Naturally she rolled over and snuggled up into my manly arms and poked my groin with her very womanly bottom which gave up the lie to my ED when my erection made itself happy between her cheeks after a rather uncomfortable ten minutes for me she rolled over again and mumbled something to me, with my ear blocked by one pillow and her words slightly slurred I opened my mouth to ask her to repeat herself. Of course my timing was perfect, as I opened my mouth she vomited in it.
For the rest my sex life is boring, goats and sheep don't really do odd things .