What's the worse sexual encounter you've ever had?

[viking8x6]

Normally I'm very good at forgetting the awful ones. Sometimes the good ones, too... but there you go.

I happen to remember this because it only happened a couple of weeks ago. Strictly speaking, it doesn't qualify as bad sex, but it definitely belongs here.

My BF happened to be visiting, and we're cruising the apps for a little 3-way fun (and just to see what's out there). Suddenly I get this message (on Grindr I think) out of the blue from a guy over 100 miles away who wants me to fuck him that afternoon. Apparently he's driving through my (rather small) town on his way from his city to his final destination about 5 hours drive from there. And took the trouble to do the searches for guys along the way (which is a pretty substantial pain) and pick out the one(s) he likes. I'm flattered.

So I explain my BF is visiting and that we'd be cool with a 3some if he's up for that. Pictures are exchanged. The guy is quite nice-looking - mid-40s is my guess and well worked-out, obviously takes care of himself. My BF is a teddy bear type, furry and round, and I'm a daddy wolf, and both of us are in our 50s, decently preserved for our ages. I mention that my BF would be into 69ing him while I fuck him. He gives me an ETA of 3-4 pm.

Along about 3:30 or 4, he contacts me saying he's been stuck in traffic for half an hour (true, I can see it on Google maps) and will be delayed. I do the math to get a new ETA and get 6pm, so obviously he was running late already. But there really was traffic, and we don't have plans, so fine.

He shows up (right when I expected) and yes, he's hot, but he says it has to be a quickie, which doesn't surprise me nor put me off, I'm fine with that. So we cut to the chase. Everyone into the bedroom and get undressed. He's clearly very into my dick, although when I suck him off a bit, he's not getting all that hard - he's just vocal about how much he likes it and wants it. Fine, I guess he's more of a bottom, but that wasn't mentioned and it's cool.

It doesn't take long before he's bent over the bed anxious for me to fuck him. Well, BF is kind of left out in that position and is clearly interested in sucking the guy, so I flip him over and put his feet over my shoulders. I grab the lube and am just applying it to my dick as my BF goes to suck him, when...

He suddenly bursts out with "I'm sorry, I can't do this," jumps up and slaps his clothes on, and bolts for the door! By the time I can pick up my phone he has already blocked me.

I'm pretty sure he could have figured out that it wasn't going to work before I got to the point of lubing up. Just sayin'.

But whatever. Karma's a bitch, dude. Hope she dishes you out exactly what you deserve.

 

Edited August 31, 2021 by viking8x6
Formatting

[Studpony123]

My worst fucks had a condom involved. it was long ago before I had adopted the BB lifestyle. I was at a bathhouse made the guy where the condom, he couldn't stay hard. he couldn't even get it in my hole. it was embarrassing and definitely awkward. The second time, my man asked to fuck me bareback and I let him for about 5 minutes and it felt amazing, and then I was afraid he would cum, so I made him put on a condom. he then proceeded to fuck the dog shit out of me. I bled for a few days after, and decided condoms were terrible.

[120DaysofSodom]

Invited this dude over to my place to breed me. He came over and he gave me a good load. The sex was great. Afterwards we were just chatting for a bit on the couch and finishing our beers. He was looking around at all my art and I have a lot of satanic imagery around. He started to tell me all about his faith in Christianity and that bullshit, and then after about 20 minutes of him badgering me about being closed minded about religion because im an atheistic satanist, I said to him that being called closed minded by a religious person is a lot like being called yellow by a bunch of bananas. He then spit in my face and told me he would punch me. I told him to get the fuck out and as he walked out, he said, "lets do this again".

[plymsleazebear]

Once met a guy while cottaging about 20 years ago, ended up meeting him for a drink a couple of nights later and went back to his to play.  Whilst he was a sexy older guy, unfortunately he only practised very safe sex.  He wasn't into fucking & would only let me suck him if he was wearing a condom.  During one session I briefly managed to get his bare cock in my mouth before he freaked out & quickly grabbed a condom, but I hated the taste of the rubber in my mouth.  We dated a few times, even visited nude beaches together but the whole safety thing really turned me off.  Think that was the point where I decided I only wanted to play bare in the future.  So there was an upside to the encounter!

[UDontHaveToPullOut]

I had just moved to the area a few weeks prior, and hadn't met any people yet. I was feeling pretty damned horny this particular Friday night. I wrapped up work early, showered, and started looking on the apps. This cute guy hit me up, shorter vers guy with a nice trim beard and fit body, and he was ready to fuck. He was hanging with his buddy in a hotel room, an attractive guy. The friend also hit me up and both seemed decent, so I decided to drive the 15 miles or so and meet them. I got to the hotel and asked for the room number - no response. After a few messages to both of them, and waiting for about 15 minutes, I figured I had been catfished and was about to leave. I cranked my Jeep, flipped the lights on, and as soon as I threw it in reverse there was a loud knock at the window, which was the bearded guy - wearing just a jockstrap and t-shirt, no shoes, no pants. He said they fell asleep and apologized and to come on up.

I followed him up, where the friend was asleep in a chair. More like passed out. He eventually woke up, went to the bathroom and came out a few minutes later high as a kite. The other one did the same - but the bearded one, when I say he didn't stop talking, I mean he literally talked at me non stop, asking questions (but not waiting for the answer) and was barking orders to everyone on how he wanted things to go. Then the friend pulls out a pipe, lights it up, and immediately sets off the fire alarm, which goes off endlessly until the hotel people show up to see what's up. They didn't bother to put clothes on, and the first thing they said to the hotel people was "There's no drugs here, we swear!" while both are in jockstraps. As soon as they left, saying the police would have to come to file a report, I booked it. Most nerve wracking, crazytunes hookup ever.