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

[Guest]

11 hours ago, Bearhunter55 said:

Had a kind of hot top dad bear over - he said he was ALL top.   He comes over, we strip as we're standing - as we make out and I rub his cock, his kissing is basically mauling my face. Every minute or two (time kind of hard to measure since every min felt like 10 minutes) he'd pulled away and clear his throat which was all phlegmy. Meanwhile his cock never got the slightest bit aroused (and he wasn't touching mine).  He kept saying how he's going to fuck me good but I was like, with what? Not that cock that is soft and totally unresponsive. At some point I knew this was not ever going to work but had to figure out how to end it.  Finally after maybe the 20th throat clearing I said something like maybe we should try this another time (er, never) when you're feeling better and HE DID NOT KNOW WHAT I MEANT!  I'm also fine with a guy not getting hard for whatever reason but he kept acting like he was going to fuck me and it didn't seem to register.  I finally got him out and a few days later he messaged me and acted like we had a fun time and wanted to play again, no "I'm sorry it didn't work out, I was nervous, etc", he seemed to think it was a great connection. No. 

Eww, Did he try to French kiss you with that phlegmy mouth? 

[PendragonSpirit]

Many years past (thankfully), I kept running into the same person - whether it was cruising a local bookstore, park, or bathhouse. He was nice enough, relatively handsome, decently equipped... except every time we'd run into one another in the same place, he'd make a beeline right for me. And me, being a generous and patient sort, would indulge him and we'd fool around. Which was fine... right up until the point he was going to fuck me and he would inevitably ask "Do you like me? Will you be my boyfriend? Do you want to date?"

I mean, if that's a kink of his, that's fine, but there was never any discussion of it, and it was such an awkward moment it killed the mood.

Every. Damn. Time.

So I'd make some excuse-type noises and leave, until I ran into him again later.

Part of it's my own fault, I should have just pointed out that if I'm cruising for anonymous bareback breeding, I'm probably not out there looking for Mr. Right.

Haven't seen him in a long while, though; I can only assume he moved somewhere else.

[FunCheerSlut]

Great question. There have been many (more than I care to admit), but the ONE that stands-out most was just bizarre.

This happened at least 10 years ago now, so the details are getting fuzzy...but I was using "Plenty of Fish" a decade ago for hooking up. Had agreed to meet up with a guy late one weekend evening. He showed up and I welcomed him into my house; fortunately, I was not alone and my boyfriend was with me. We had offered this guy a two-mouth blowjob. So, it started as expected UNTIL he pulled out a hand-gun and put it on the table next to the sofa. He "explained" that he brought it with him for his own personal security, etc and it was for self-defence. I was like WTF (my boyfriend and I were looking at each like "what do we do"?)!!

So, we proceeded to move forward with the offered two-mouth blowjob. What was shocking more than anything was that this poor man's penis appeared as if it had been run through a meat-grinder and he wasn't left with much. Obviously, he had some type of medical condition and there was some type of surgery to try and make a "penis" for this person. Ironically, there was not enough real-estate for two mouths to even try and pleasure whatever it was between this person's legs.

We tried to get this person over the edge and to the point of climax as quickly as possible so we could reasonably conclude our end of the agreement and bid this person a quick and efficient farewell. I was happy when the guy and the gun had finally left my home. I never felt such relief from a stressful situation.

[tallslenderguy]

my worst happened in 1998, was at a cruisy restroom where i often took cock under the stall wall. Did the usual signals, tap foot and passing notes written on toilet paper to see if we both wanted the same thing. He asked what i wanted and i told him i wanted him to fuck me. He stepped outside of his stall, knocked on mine and when i opened the door, showed me a badge and told me i was under arrest. i was handcuffed and driven to the police station in the back of a cop car, then had to hang out for a couple of hours as i was photographed, finger printed and booked. Had to talk with a magistrate who shamed me to no end. i was still married at the time and on the DL, so i was terrified about being found out.  

When i was released a few hours later, i was charged using a 100 year old sodomy law and charged with solicitation for a felony, i ended up hiring a very expensive lawyer, feeling very vulnerable. i had to go to court 4 times before there was an actual trial, it drug out for a year.  When i was finally tried, the prosecutor was going for blood, the then attorney general was a conservative who hated gays and he wanted the worst for me. The judge was liberal and practically laughed telling me i needed to be more careful. He asked my lawyer what he wanted and my lawyer said: "i don't know judge, what do you suggest?"  The judge suggested reducing the charge to indecent exposure (even though there had not been any exposure), a misdemeanor and a $500 fine. i was so relieved though, i just agreed. Afterwards, the cop who had arrested me approached me and apologized for arresting me. Thankfully those days of entrapment are gone. This was Virginia and vice cops used to hang out at all the parks and cruising spots pretending to be gay and looking, then would arrest the guy when they asked for sex. 

 

[leatherpunk16]

I generally don't have bad sex stories - if they are unsatisfactory, I tend to not remember them. This one, however, is recent enough that I do remember.

During my first week in Seattle, I was living out of a hotel. A fisting pig approached me (probably through Recon), and came to my room. We chatted for nearly 30 minutes, I wore a red wrestling singlet and matching jock and red socks. This guy was definitely bugged, and that's probably what drew my initial interest. The back and forth was pretty good, and I expected a great time between us.

I mixed up the last of the J-lube, and got him naked. He knelt on the bed and bent over. I had a look at his hole. Did not look blown out from years of fisting, but maybe it just didn't show. Maybe it's been a while. Maybe he's all talk. (I quickly found out that it was the latter.) I gave him my good poppers, and slowly applied the lube. Got my hand good and covered. I got no more than two fingers into him when he suddenly leapt up, said "It's not gonna happen tonight," and before I knew what happened, he was dressed and running out the door. 

In his haste, he left behind his mobile phone. I'm standing there, dumbfounded, with a handful of wasted J-lube, and wondering what just happened. A couple minutes later, he dashes back into the room, grabs his phone, and leaves without a word. I heard his thunderous footsteps as he pounded down the hall in a hasty retreat. 

This led to me calling up someone else who was interested, but fighting was his fetish, and that was even worse. I'm not skilled enough to really punish someone physically, and he wanted to beat the snot out of me. Doesn't do any penetrative sex, which isn't what he advertised. Two shitty encounters in the same night.

Here's the fucked-up part: The alleged fist pig hit me up a week later, and asked to try again. I told him no. The fighting guy had nothing to say to me until months later when he asked if I knew where he could score some meth. I blocked his ass. 

Welcome to the PNW, right? LOL

[blackrobe]

31 minutes ago, leatherpunk16 said:

Welcome to the PNW, right? LOL

It makes me long for the directness of my home town.

[Guest]

This is turning into my favorite thread. 

[BlackDude]

8 hours ago, tallslenderguy said:

my worst happened in 1998, was at a cruisy restroom where i often took cock under the stall wall. Did the usual signals, tap foot and passing notes written on toilet paper to see if we both wanted the same thing. He asked what i wanted and i told him i wanted him to fuck me. He stepped outside of his stall, knocked on mine and when i opened the door, showed me a badge and told me i was under arrest. i was handcuffed and driven to the police station in the back of a cop car, then had to hang out for a couple of hours as i was photographed, finger printed and booked. Had to talk with a magistrate who shamed me to no end. i was still married at the time and on the DL, so i was terrified about being found out.  

When i was released a few hours later, i was charged using a 100 year old sodomy law and charged with solicitation for a felony, i ended up hiring a very expensive lawyer, feeling very vulnerable. i had to go to court 4 times before there was an actual trial, it drug out for a year.  When i was finally tried, the prosecutor was going for blood, the then attorney general was a conservative who hated gays and he wanted the worst for me. The judge was liberal and practically laughed telling me i needed to be more careful. He asked my lawyer what he wanted and my lawyer said: "i don't know judge, what do you suggest?"  The judge suggested reducing the charge to indecent exposure (even though there had not been any exposure), a misdemeanor and a $500 fine. i was so relieved though, i just agreed. Afterwards, the cop who had arrested me approached me and apologized for arresting me. Thankfully those days of entrapment are gone. This was Virginia and vice cops used to hang out at all the parks and cruising spots pretending to be gay and looking, then would arrest the guy when they asked for sex. 

 

Damn that’s wild. I know cruising is illegal, but we are basically wasting money on busting gays in restroom? And then to go to a trial…ridiculous….

[tallslenderguy]

12 hours ago, BlackDude said:

Damn that’s wild. I know cruising is illegal, but we are basically wasting money on busting gays in restroom? And then to go to a trial…ridiculous….

This happened in 1998, i hope no such thing would happen in this day and age. Straight people 'cruise' each other all the time, pick up each other in bars, etc. You don't find vice cops at straight bars busting straight people for asking each other  if they want to have sex, only if money is involved.  It's just an example of anti gay laws and those who love them.  Honestly, i think it's insane that it could happen even in 1998. 

[Spunkinmyarse]

Same year it happened to George Michael in Los Angeles, as it happens...  

[john54476]

I have to laugh about many of these but one in particular hit home.

I had posted and add on craigslist offering blow and goes, this guy shows up with two viscous doberman going crazy in his suv--I took him up to an apartment I was showing, get on my knees. He pulls up his shirt and pulls out a 357 and sets it on the counter, WTF, undoes his pants for me to get to work--I was scared shitless and thought he was going to kill me. It was the longest blow job I have ever given even though it was a only a few minutes. Took me a long time before I posted on CL again.

[blkoraltm]

Both occasions occurred during my unemployed time in 2008.  

1.  My first occasion was just a blow job but still was one of my scariest of my life.  I was sucking a guy's dick in the park and the police came into Loring Park in downtown Minneapolis and luckily they didn't catch us but it was time to move on.  So we got into his car; and continued.  When I went back to work we were now mobile and it started out ok; and then as he got more excited his foot got heavier on the gas pedal. And even though we were on streets I swear we hit near 50mph with me out of my seatbelt and my head under the steering column of his moving car.  NEVER AGAIN. 

2.  I once again met up with someone at Loring Park; and I wanted a little more than just having my throat used. So I invited this man who appeared to be homeless to my apartment.  We walked up the stairs went into my bedroom and had a good ole time.  He used my hole well and I enjoyed the experience it is what happened afterwards that caused the issue.  As he left he grabbed my phone and like an idiot the first call he made somehow ended up to my sister which started a emergency situation with my family.  She called my mom and my dad; and before I knew it at like 4am I had a ton of company.  Folks coming to check to make sure that I was ok; that I wasn't kidnapped, being held hostage or just mugged.  I let them know that I had left my phone on the table of a coffee shop late at night.

Since I was unemployed everyone knew I saved money by not having WIFI and would go out to the coffeeshop during the summer and "borrow" WIFI from a coffeeshop around the corner. And someone must have picked it up; I would go out and apply for jobs from like 12am to 2am since the coffeeshop closed at 10pm and the crew would be gone after cleaning up between 11pm-12am. Needless to say no more homeless folks invited into my home.

Edited August 12, 2021 by blkoraltm

[truepig]

Craigslist ad - Drove 20 mins. Turned out he had an extremely tiny dick, sucked him. Took him all of 2 mins to cum. Then kicked me out. Kept bugging me and bugging me to come back. 20 min drive for 2 mins sex was not worth it to me.  Years later, I'd let him come over to house after he got of work, cause he "stunk", pits were sweaty, pissy dick and a ripe hole. He still didn't last long before he shot his load but I'd get to lick his sweaty parts and he'd quickly fuck me raw. Then put his clothes on, no clean up or wipe down, I got to like him because of that. 

[backdoorjimmy]

I hooked up with a guy who begged me to sit on his face so he could be "smothered" while he ate me out. I told him to use his hands and guide my ass where he wanted it and he agreed. As soon as my ass came to rest on his mouth he panicked so I got up and he was pissed because he had a claustrophobic attack. He lost his erection so I made sure he was okay, then I left. Later he texted me to say I ruined the hookup and called me the three letter F word, then he immediately blocked me. 

[VersatileBreeder]

A Vers guy I had hooked up with had invited me over to his buddy’s place. His bud wanted to get fucked by both of us. Was kind of a late night spur of the moment hookup. So I show up.

First issue- I walk into the apartment with the guy I know and we see an old woman with an oxygen tank, sleeping in a wheelchair. I got nervous we were in the wrong apartment but he whispers to me “no it’s OK, that’s his mom. She can sleep through a war. But we have to be quiet.”

That already heightened my nerves but I walk into the next room and find the guy wanting to be fucked. Not at all what the guy had described to me looks wise and not the type I’m attracted to at all. I had half a mind to leave but it was one of those “fuck it, I’m horny, let me just bust one in this guy’s hole and go home and sleep” decisions.

The guy was so high on meth he hardly even acknowledged we were in the room. Was like a total spun out zombie. Anyway, I lube up and stick my dick in. Then I felt it. That extra warm squishy feeling. The dude was not douched, not even a little bit. Just ass packed full with shit. I immediately pull out and my cock is CAKED in it. I’ve had accidents with bottoms before but the smell of this one was horrific. I actually gagged and almost threw up. I ran into the bathroom and looked away as I scrubbed my dick with soap and hot water. The smell just kept creeping into my nose, making me gag. 

I got dressed and got out of there ASAP. Not a word from the bottom. No “sorry about that” just a total methed out, dirty hole zombie. Was actually kind of sad. I blocked both guys on BBRT after.

Edited August 31, 2021 by poptronic
Typo