Really bad sex. What is the worst sex you’ve had

That’s not sex, that’s foreplay.

I want more about that encounter, please, OP!

With a 27 year old man who neglected to tell me that he was a virgin when we had sex for the very first time. He was good looking, had a great body, and a perfect cock that he had no idea how to use.

He actually proposed to me. It was really sad and highly inappropriate.

2 exes.

Ex number 1 had a pencil dick.

Ex number 2 was inept in sex, although he thought he wasn't.

Both had hygiene issues.

Probably me - I can lose interest between the bar and the cab ride home. I've started and ended a hookup many times before sex. Yes, I'm a jerk.

R4, hygiene issues? Deal breaker from the get go.

Tried it with a Thai boy when I was living in Honolulu. Back in the late 80’s, all the hunky guys I wanted wanted Thai boys. So I tried it. Sweet kid, Brought him home. He didn’t kiss, but kind of pecked at me. It was like making love to a bird. So I stopped, and explained he had better go home, which he did without complaint.

I agree r6, but they didn't get lazy with the hygiene immediately.

Why would you want to remember

R7: you had bad sex with a fucking kid? Are you serious or are you trolling us?

Went home from the club with a guy who was so drunk he fell asleep while I was sucking his dick. As in started snoring loudly. Way to rattle my fragile self-esteem, ya goober.

That feeling of orange Tang on my poontang.

One Halloween night in the 1980's, I had a bit too many holiday drinkies and went with a bar pick-up back to his apartment. He fucked me in the ass, which was easy to do as I was wearing a ginghamsquare dance dress.

But the booze won out and while he was fucking me, I puked on his bed.

Yup. That was it. The worst sex I ever had. Probably the worst that guy ever had, too.

R13, I puked on a guy once while having sex, but having sex with the 27 year old virgin was actually worse.

Buck toothed bareback

I found out a guy was missing a hand during sex. I went to grab it and realized there were no fingers. In my defense the bar he picked me up in was dark.

How horrible!

LOL R16.

Mine is reg. vanilla boring.

Entered me. Couldn’t stay hard (despite the Viagra).

Used fingers (finger?) terribly and probably tore something. Gave him a satisfying hand job.

These stories help confirm my decision.

It involved road house whiskey.

Any time a guy shits on my dick when we're fucking. WHY DO THEY DO THAT????

Guy kept interrupting everything with questions such as "So are you nervous?", "How long since you last relationship?", "Tell me what you want to do?" multiple times during what seemed like an endless encounter. It was like terrible sex with an amateur psychologist.

R21, a commentary on your performance?

[quote]Any time a guy shits on my dick when we're fucking. WHY DO THEY DO THAT????

Thats the problem with hooking up with guys without planning. Bottoms need notice if you want to fuck, they need time to clean out. That's why dates are better than instant hookup.

I had a date steal money from my home. I foolishly left out my rent money on a table, which is something I usually never do, and after he left I saw it and counted he had taken most of it. Nice of him to leave me something, I guess. That was more memorable than the actual sex.

But, I just figured that was my payment!

One time a guy threw up in my bed. One time a guy threw up on my dick while blowing me. One time I went home with a guy and as I was fucking him his 4 year old appeared and asked where mommy was. A separate time I was blowing a guy and his child came in and thought I was someone named "Marty." He at least was married to a man. One time I was fucking a guy on a blow up mattress and it started to deflate and his friends came home and I knew them. I used to be pretty indiscriminate and drink a lot.

You could write a book!

R16, I think you are winning the thread at the moment. I keep chuckling.

One guy I was fucking kept saying thank you, thank you, everytime i went into him. Most offputting.

And I had one guy projectile vomit on my cock when he sucked me off.

I had protected sex with this guy. When we were done, he pulled the condom off me, went into the bathroom and started squeezing it over the toilet to see if there were any holes in it. WTF? Like I sabotaged the rubber...

when you grab his dick for a handie and realize the head doesn't extend past your palm....tiny? Definitely!

A couple times when a disgusting, lazy ass bottom didn't clean out properly ahead of time.

Trauma! Tragedy! Tribulation!

THANK YOU!! THANK YOU!!!

I’m an eldergay. The best thing about not having sex anymore is not having bad sex anymore.

Not to mention the time and effort saved by not having to go looking to get laid.

[quote]One guy I was fucking kept saying thank you, thank you, everytime i went into him

This was the funniest one so far.

Oy,pick one. One of the absolute worst was the guy with a baby arm for a dick that I swore on a stack of bibles I wouldnt shit on.He was so reluctant to have anal because of multiple bad experiences,but I starved myself for 2 days beforehand and douched several times,so I just knew I was good to go. When he finally got that huge thing all the way in he got about a dozen pumps and I projectile shit all over him. I mean it shot out like a firehose.He was of course repulsed,and I was mortified beyond belief. Another was the hot to death biker daddy and his wife who I agreed to have a 3 some with. It was readily apparent he and I had a groove on and she was sort of ignored.Right as he shoves that juicy dick into me,she jumps up and starts screaming at him.He screams back as he is still pumping.I wriggle out from under him,grab my clothes and book out the door,the whole time they are still screaming at each other.

I am legitimately cackling, R39!

R7, I’m a haole who also lived in Honolulu in the late 80s, and can corroborate what you said about Thai boys.

One of them wanted me to move to Bangkok with him and enjoy the fruits of his success as a Barry Manilow impersonator.

Nothing came of that, but we did have some *great* meals - it makes a difference, being able to order in Thai.

I got drunk at a party once and passed out, woke up with a dudes dick in my mouth, puked on him.

Thats the story.

What's with all the throwing up??? Drunk/on drugs?

I understand shitting. But I don't know why people just don't go in a few inches. After that you're clear up in a guy's intestines, then you wonder why it happens?

r43 A surfeit of alcoholic beverages had been consumed. ( I was young and stupid.)

R16, how do you know the guy didn't lose his fingers inside your hole?

NYC circa the early 2000s.

The model James King.

Heroin.

Loose bowels.

Nutella time.

That's all I'm giving you.

[QUOTE]I starved myself for 2 days beforehand and douched several times,so I just knew I was good to go. When he finally got that huge thing all the way in he got about a dozen pumps and I projectile shit all over him.

That makes no sense. The guy's dick must have been laced with some powerful laxative or something.

Spent the entire weekend in Montreal with platonic traveling companion and we both want the same hot guy. Took him everywhere with us buying drinks, breakfast etc. flirting to let him decide who he wants and other guy winds up with him.

The next day I put poncho and sunglasses on to walk my dog and see same guy in the street, he doesn’t recognize me and asks me for a dollar.

I realize the guy was homeless.

Kept hitting the mother lode when fucking my uber-bottom bf-he didn't understand the concept of douching. He found a hung compliant Mormon. That sex doesn't bear thinking about.

[quote]I realize the guy was homeless.

Or your friend forgot to tip.

IT INVOLVED A DUCK BOAT AND A CRAIGLIST “FRIEND.”

A Grindr hookup who had major hygiene issues. I gagged when he entered my apartment and told him to leave.

I dated a really nice guy for a couple weeks and the first time we went to have sex I discovered he had a 3 inch dick. He said. "Sorry, I know it's tiny." That was our last date.

I was also someone's worst. I was fucked up on ludes and literally passed out inside him.

Brought home a skinny guy and he pulls out the biggest cock I ever seen in my life. It looked like a third leg. It was as thick as a beer can. He tried to stick it in my ass and it wouldnt fit. I tried to suck it and it fucked up my jaw and my jaw was sore and popping for a month.

R52 and R53 - I've "had" both extremes (I never let either fuck me, though). It's such a bummer when a dick just won't do. :-|

It has taken a number of years to learn my lessons from the bad sex that I had in my teens, 20's and 30's. Thankfully I now have two regular fuck buddies who make me happy. Hope they are happy too. Never had poor hygiene issues with my guys, only a few scat instances, no missing limbs, a few very small cocks, and a few bad blow jobs. Probably the very worst is when I was with a really nice guy and we had terrific sex for the first couple of months in our relationship, then it got boring and predictable. For me, that is the worst. To have a great guy and the passion fades.

This is disgusting, but you asked. This guy I was drilling doggy style who had sudden bad diarrhea. I literally fucked the shit out of him. Even thinking about it today makes me heave.

This thread makes me never want to have anal sex.

R16, the missing fingers issue would have had me screaming my head off...!!

Anybody who says "does that feel good?" while they're doing something to me makes me feel like I've had a bucket of cold water thrown on me. A total turn-off.

R59 - actually most verbal feedback needs to be limited. I also hate when some guys role play to the extreme - this is NOT PORN! This isn't how you have sex - by saying ahhh...yeah...you like that...ugh...more...yeah...i'm your slut...do I feel good?...you like that dontcha...?

Shut the fuck up!

R60 - You have me LOLing! SO true!

I have to admit, I've become ridiculously self-conscious about what I say when "moaning" during sex now, cuz I feel pure porn even if I'm saying, "Oh, FUCK yes!"

But in fairness, it’s difficult to not say all that stuff we learned in porn during sex. After being raised on Sean Cody and other internet, how do we break from the tools that taught us what to do?

R62 - I try to keep that in mind, actually. I forgive my porn-brained self.

R62 - actually, they don't talk that much in Sean Cody - the scenes are pretty good with choreography and everything. Or course it takes several hours to shoot those scenes, but he edits pretty fucking well. But there is one scene with that salt and pepper handsome guy getting fucked where he just goes over the top with talking - but it looks real because he is about to cum in a huge way. That's forgiven and understandable and even appreciated.

All the other shit - a little goes a long way - just sayin'.

That time when I got pneumonia and coughed so hard I broke my ribs. I also had a sprained back so each cough was like a hammer to the back and a stab to my lungs.

Wait, what are we talking about?

R16 LOLOLOLOL

Airplane toilet with the purser banging on the door while we're in the throes of.

^ Did you not have the occupied sign on?

Some of you could write a homosexual survival guide.

R60 I had sex with a guy who made no noise at all. Not a single moan, no “I’m going to cum”, barely any heavy breathing. It was VERY weird. Afterwards he said it was great and asked to see me again. WTF. I’ll take an odd “oh yeah, more” over that creepy dead silence any day.

The sex didn't actually happen. Met up with a guy I knew, and took his underwear off and his cock was black and purple. Like he'd been torturing it. He told me to ignore it, took me to the bed room and pulled back the bedclothes. The under-sheet was covered in skid marks. I left.

Met a guy when I was up in Edinburgh. I fucked him so hard he pissed himself all over the hotel bed. The next year I met him again and while fucking him he shat everywhere, like a fountain of shit, all over the hotel bed.

He actually asked to hook up a third time. I refused.

Me and my mate were keen for a 3some. We put an ad on CL. A guy responded, said he was 24. He sent a body shot, looked tight. When we opened the door, our hearts sank. He was indeed 24, and slim and toned. But he had Progeria. Aka "Methuselah's Syndrome", where you look geriatric before your time.

Me and my mate were still so young and both had a people pleaser streak, so we let him inside. He was over the moon. My mate ran to the bedroom and threw a red cloth over the lamp, to dull the light. We let him suck our cocks for a bit, then he wanted me to fuck him. I couldn't do it, because whilst he had the face of a wrinkly old man, his body was actually tiny.

My mate pretended to come, and I said I was feeling tired. We all got dressed, and the guy looked at us and said "what do you think of me?" We felt so bad for him. He worked at a chicken factory, plucking feathers. It was probably the only sexual encounter of his life. It was so gross for us, but also a funny story to remember.

[quote]He fucked me in the ass, which was easy to do as I was wearing a ginghamsquare dance dress.

Possibly the gayest sentence I've ever read.

It was a guy I had a crush on for a couple of years and was very happy when he hit on me, but we never got to the sex part because when we started fooling around he kept saying “oh yeah, good boy, that’s nice isn’t it. Yeah that’s making me hard, good boy” Good boy? Im a grown man, not a puppy or a 12 year old boy. He said it so many times and it was so off putting, I left. There’s no way the sex was going to be any good with a person who sounds like my dog trainer. Months later I run into his housemate who tells me my (non) hook up died in a car accident just weeks after I “left him high and dry” and storms off. Still not sorry I didn’t fuck him.

I met a guy at a bar and went to his place. He kept saying over and over “I’m gonna be the best you ever had!!” as he kissed me aggressively and sucked my cock really hard. It was more comical than sexy

I came and got out of there fast. I laughed all the way home because it was so ridiculous.

[quote]The next day I put poncho and sunglasses on to walk my dog

And now, maybe the second gayest phrase I've ever read.

I fucked a married guy and when I pulled my cock out it looked like I'd dipped it in a can of chocolate frosting...I'm now more of an oral only guy now.

He'd have to jerk off to get it up, which quickly went away. He'd always blame heart medication on it. Would lay there like the lazy ass he was and expected me to do everything. Then, he'd lay there and jerk off to cum and scream out in pain. I thought he would have a heart attack at any moment. Horrible kisser whose tongue was always cold and wet from drinking water. He'd walk around the apartment naked with his little nubbin barely sticking out of his gut.

Major turn off, yet I spent 4+ years with this douche. That's what no self-esteem gets you, I guess.

After dropping their pants I saw their shameful tiny meat. Ugh! 😫

[quote]Airplane toilet with the purser banging on the door while we're in the throes of.

The purser? What else does the purser do on the plane...I mean officially?

R78, Betty Crocker?

R73 Kind of you guys.

R81- I think it’s what the head flight attendant is actually called.

R73, that was very sweet of you. And you don't have his death on your conscience, the way R75 SHOULD.

Got picked up at the Seattle Eagle in the early 1990s. Hot bear, I thought out of my league. Back to his place. We're in bed, I'm rimming him. Clean ass. I moves around to his cock and start lickingand sucking. Then he starts farting. And farting. And I pick up my clothes and get dressed and leave. A few weeks later I'm talking about this with some guys and one of them says that's his way of getting out of sex if he decides you're not hot enough for him.

The time his wife walked in while I was pounding his ass and asked if she could watch.

But, R86, not in your case. He'd eaten Mexican earlier that night.

R81 - Maybe Gopher was moonlighting?

There was this real hot muscled dude with a deep sexy voice and pretty hair I've ways talked to from an app but never met.

One day he calls me in the middle of the night for a quickie and once we start kissing I realize he was wearing a toupee ( which is silly since bald man are hot as hell) when he notices I was surprised sice the hairpiece was moving as I grabbed his hair he drops his masculine demeanor and turns to me in the most effeminate voice: gurl didn't you know?

My boner was gone. I laughed and he got really pissed and left.

Same here R90. We met at a bar in Amsterdam - dark, drunk. He was Asian and I thought he looked like 24. Having sex and the hair came off. Looked like a drag queen. Impossible to continue.

"... I put poncho and sunglasses on...."

MARY!!!

This involves no sex: I offed a gogoboy in Bangkok. This was the second time I took him. We go back to my hotel and he goes to the bathroom to “clean up”. I had a corner room so the bathroom is huge - possibly same size as the main room. From my bed I can hear the water spray sound of him douching. And douching and douching. I remember thinking what the hell is taking so long. About 20 minutes later he comes out. I quickly go in to wash my hands. What do I see ? The whole room is flooded with floating diarrhea bobbing up and down. The floor drain is clogged up with shit. I quickly sent the boy away, said nothing. But he acted completely normal, as though nothing was wrong. Too embarrassed to call reception, I took a mop from the floor’s utility closet (mercifully unlocked) and spent the next half hour cleaning up the mess.

God that's disgusting R93. I really shouldn't have read it whilst eating dinner

Only do anal with people you know and trust. Otherwise....surprises. Which actually should not even be a surprise.

So many tears could have been avoided if you bottoms just added to your diet a spoonful a day of psyllium husk.

They never learn.

R96: Thanks, Heloise!

Bottom with a micropenis who cried after I stuck my dick in his ass.

THE WORST.

I traded face and dick pics with this cute little otter on Scruff. We decide to hook up. I get the pants off, and BAM, I learn she’s and FTM with a phalloplasty (see below). I was horrified, repulsed, insulted, you name it. I made her leave without getting dressed, and told her that if I ever saw her on the apps again, I would stage a crime and frame her for it (I work in law enforcement). I took a picture of her face while she was leaving just so she knew I would remember her. She was crying but I just repeated “too bad, you shouldn’t lie to people”.

I kept her pants (they’re good to work out in). As harrowing as it was for me, I still chuckle at the thought of her taking the bus home naked from the waist down and looking like Frankenstein’s monster. Maybe that’s cruel, but I think she learned a lesson.

What R70 wrote. Silent sex is the pits, and too much “porn talk” sounds asinine. Because both extremes are bad, meet me somewhere in the middle.

If you can’t think of any occasion when you had terrible sex, YOU were probably the terrible sex.

[R99], you’re a total cunt. Congratulations.

This thread was fun until we got to r99's sociopathic post.

R73, a person with progeria has a very short life expectancy. They usually die right before or during puberty. Some MIGHT make it past puberty, but that’s quite rare and unlikely.

The ones who make it past puberty are usually girls, and almost none make it into adulthood. The ones who do, still die relatively early, and don’t make past their late teens, early 20s.

I’ve had a few instances where guys have lied about their age and been clearly, obviously much older than they stated. I’ve shut the door in their face immediately.

When I was 19, the first guy I fucked shit all over my dick. It was thick and viscous. Absolutely revolting, and to this day I can’t get a hardon for anal, and don’t like to receive it either.

But recently, I met a guy off Grindr last month who was looking for head. My city is over saturated with thirsty cocksuckers, so I went for it. We traded pics . He was 24, decent looking. I arrived at his place at 2am, and he was acting so strange.

He asked me on three different occasions where I was from, asked me if I wanted water twice after I said no the first time, and was walking around his apartment acting like a total weirdo. After 10 minutes of this shit, I finally ask, “so do you want to do this?” And he says “Do what?”.

Losing my patience I say “suck your dick”. He says “oh yeah” and then proceeds to go fiddle with something in the living room. At that point, I grab my shirt, shoes, and practically run out of the apartment. He was saying “but wait” as I unlocked the door. I blocked his crazy ass on Grindr and haven’t seen him since.

While I agree R99 was wrong, what she did was also wrong. And as harsh as he was, it could have ended up much worse for her—she’s lucky she wasn’t physically harmed, as I can imagine some guys would have wanted to inflict pain after such a betrayal.

She shouldn’t have lied. FTM’s that prefer guys are an odd bunch indeed. They severely restrict their sex/dating options because most gay guys are bottoms and not interested in anyone with a vagina or fake dick. Most straight men won’t want them because straight men are attracted to femininity.

In any case, I bet she never did it again. Hard lesson. But she deserved it.

I went on a few date with this guy just to be nice. His face wasn't bad and he had stunningly beautiful blue eyes. I'm talking like piercing blue eyes. Almost surreal. He wasn't really my type and seemed like he might be a little dull. His body was pretty gross. He didn't take care of himself well. He was nice enough when we went to the state fair, but he was so fucking boring the entire time. We ended the night and that was that.

It was a few days later and he texted me later at night. It was after 10 or 11 and wanted me to come over and fuck (which we hadn't done yet). I had a free evening, so I figured "why not? Maybe he's actually very good at sex." I went there and we got in the shower. He started rimming me almost instantly and I couldn't feel a thing, but I moaned along with it. We get to the bed and he puts on a condom and starts fucking me and, not only is it small, but it won't get hard at all. I swear, we spent 10 minutes trying to get that sucker in and stay in. It was so awful and awkward. Finally, I told him this wasn't going to work and he sucked me off (which he actually wasn't too bad at) and called it a night.

Sometimes, you give people a chance and they exceed your expectations, but this guy was just about as I'd imagined he'd be.

I also got fucked by a really hot guy and I accidentally shat on his dick. I was mortified and I've never done that before or since. Weirdly enough, it didn't stop him. He washed me up in the bathtub himself and continued playing with my hole. Brave guy.

Unsolicited spanking is a dead turnoff for me. as is any reference to Daddy.

R99 I hope you get flattened by a steamroller.

Oh yeah r108, mention daddy or spank me and I’m gone. Men’s daddy issues are a turn off.

Bump

R24, if you STAY ready, you don’t have to GET ready.

I always thought BDSM was stupid but since the tops fucking were kind of boring I decided to give it a try, under the wrong assumption a dominant top would cater to my needs.

We met, he wouldn't kiss (major turn off for me). Then, he proceeded to gag me with his dick (another turn off) and began calling me all sorts of stupid names like vermin etc, so I laughed because it was actually funny to me.

We still tried once more and then he smacked my face so hard I've automatically pushed him away and punched his chest. The moment I did this his dick went limp and he couldn't get it hard again.

We ended up talking a bit about this. He called me a sub in the closet who would one day admit he likes to be spanked. Nonsense.

It was very sad after this. He had a boyfriend he NEVER kissed and I realized he looked like a robot, almost a psychopath, no emotion towards anything. I felt sorry for him.

I've never interacted with a BDSM person again and find them all to be either full of person traumas (the subs) or sociopathic bordering psychopathy (the doms).

Very enlightening experience. I finally found lots of top guys who enjoy kissing and fucking a big dicked bottom. (Please Mary! me. I deserve it).

[quote]R111 if you STAY ready, you don’t have to GET ready.

I'm telling you NOW, so I don't have to tell you THEN.

One of my earliest sexual experiences was with a super tall guy who'd done some modeling jobs. He was stunningly beautiful.

In our second week of dating we went to a house party and he got coked up. Then we went to his apartment. We hadn't had sex yet and he really wanted to fuck me badly. I'd never bottomed before and was reluctant to try. He said he'd be gentle, so I gave in.

He took out his cock which was long, thick, and beautiful. I straddled him as he lay flat and he slid it up inside me. He was gentle at first, but then I guess the coke took over and he started fucking me really hard like a madman. I was trying to decide if I enjoyed it but it soon got really painful. I made him stop and was angry, and he was really apologetic.

Still feeling pain days later, I scheduled an appointment with my doctor and learned I had hemorrhoids. I told him I had been experimenting by putting stuff up my ass. Guessing he didn't really believe that, haha.

I still saw the model guy for a few more weeks after that because as I said, he was really hot. But we didn't have sex again. On the bright side, the experience made me realize that I'm (mostly) a top.

BTW: years later the guy had a scary heart incident due to his coke habit and saw it as a sign from God that he shouldn't be gay. He now runs a ministry that caters to ex-gay organizations and is married to some chick. Of course, the ministry spends a lot of time in Thailand, lol. I found out all about his story while Googling him out of curiosity.

Can't make this stuff up.

Hooked up with incredibly hot daddyish type in his 40s. Great dick and bod. Clean all around. Oh and an incredible fuck. So heres the issue.. his breath smelled like metal. I couldn’t figure out what was going on. I love to kiss and I tried to give him, and it still didn’t work. Sad because everything else about him was perfect. I later found out that he was on lithium for bipolar and that makes your breath smell like metal. I feel like an ass.

You don't feel like a cock?

When I was a young military boy, I was banging my downlow roomie who was dating a recently divorced civilian girl. She'd walked in on her husband, his brother and another guy in a three way - him in full drag.

Years later, I picked up a very hot army guy. He asked if we could stop by the barracks before going to my apartment. He comes back with a suitcase. Alarm bells go off in my head. At my place, he takes a long time to get ready for sex.

He comes out in ... A wig, make up, women's underwear and a peignoir. Sex was a damn chore because he smelled like a woman and cooed like a pigeon. I tried to come up with a reasonable plot to get rid of him. Early the next morning, my neiy calls "what's up girl?"' I answered "oh nothing him, just sitting around in our nightgowns". He said "I'll be right there"

While we were talking he told me he'd been married but his wife threw him out when she caught him in a 3 way wearing her clothes. Before I could explore this train wreck further, my buddy showed up and threw her out.

I took my buddy to breakfast and told him the entire store. I think I told the entire restaurant the story, in German. This brought more peals of laughter than you'd expect from normally dour Germans.

Still today, I emphasize "masc for masc" and to hell with hurt feelings.

Any top with a semi-active sex life has been chili dogged, so that is nothing new. My freakiest moment was fucking this gorgeous 6'3" muscular Adonis with a handsome face, etc. This stud was ridiculously hot and an insanely talented bottom. He ONLY liked to be fucked doggie over the side of the bed (refused other positions) and actually requested that I not pull out and re-insert which I was fine with but later scrutinized after the deed was done. I didn't know or trust him well enough to bare fuck (which he wanted but I refused before he arrived) and assumed that a bottom this hot was "particularly well experienced" so I wrapped up and got down to businesses. His shapely naked ass was instantly boner-inducing and he reached back and spread both cheeks wide before I shoved balls deep with one forceful thrust. He moaned with every hard skewering insertion so I made sure to trow my weight into every impaling thrust. His hole felt amazing as he squeezed down on me tightly and then relaxed loosening completely - milking my cock like an utter with his talented anus. Never changing positions, we fucked at a punishing pace for 30 min or so when I did decide to pull out; his ass felt a little "too good" and my flared out head (a little too flared out for condom sex) kept slamming against some firm object deep inside his hole. As I pulled out, I looked down to what appeared to be a rubber band around the base of my dick and nothing else. The lube smeared on my now bare dick was a mixture of sticky water-gel mixed with a white creamy substance. It took me a few seconds to conclude that he had sabotaged my condom by filling his ass with Crisco before coming over to my place. I was alarmed and more than a bit pissed. I quickly blew my load all over his hole. He begged me to finger the cum up inside of his ass and I obliged. I instructed him to push it back out and he obliged. When the stud squatted and squeezed - he farted a tattered condom out on the sheets. Thank God I tested STD free a week later. When he begged to come back over for another round, I agreed only if he brought a hairbrush with him. Upon arrival, I put him over my knee and paddled him hard until he admitted what he had done and begged forgiveness. Seeing that his ass was full of Crisco yet again - I fisted him (or attempted to) rather than anal sex. I fucked him about 4 other times and we never had that problem ever again. He did request another spanking however..

I feel physically ill after reading this thread. I wish I could "un-read" it.

I'm surprised this hasn't popped up yet... so, it was very late and went home with a very cute guy who I thought was just very soft-spoken and had a minor speech impediment, which is no big deal. I actually asked him if he had a lisp at one point and he just shook his head. I just thought he was shy. So, we get back and he immediately gets on his knees and starts blowing me (we hadn't even kissed yet) and I realize he is missing the entire top row of his teeth. As gross as it sounds, the old granny blowjob joke is true and he clearly knew how to utilize his disadvantage. Needless to say, I never want to experience it again... and, no, this was not in flyover land.

R118: "chilli dogged" lol - I love that term!

[quote]When the stud squatted and squeezed - he farted a tattered condom out on the sheets.

R118, I don't quite understand. How could loading his ass with Crisco have destroyed your condom? Also, what was the " firm object deep inside his hole" that you rammed against?

[quote][R111] if you STAY ready, you don’t have to GET ready.

Don't eat again, ever.

r16 ...and we're assuming you lubed-up his stump and guided it towards your hole?

R118 contribution is charmingly stomach-turning.

This wasn't the worst sex had by me, but someone I observed.

I was visiting friends in Iowa and they took me to a gay club that was a converted McDonald's (signature roof, drive-through boarded-up... now it was a gay club). The inside was quite dark, and one of the bathrooms was set up really awkwardly. The one-person-only bathroom was too brightly lit and just had one big door that opened right into the club, if you opened it the light came streaming across the bar and anyone could clearly see the white tile and toilet and sink. At some point everyone at the bar started cheering. We looked over to see a skinny twink on his knees in the bathroom blowing a very overweight, kinda gross guy. I guess they forgot to lock the door and someone just opened it. Ta-da! The horrified twink got up and slammed the door dramatically and, moments later, flung the door open and everyone cheered and threw napkins at him as he stormed out of the club in tears. It was like something out of CARRIE.

Is that the guy who two days later drove into a tree?

R123 - latex is not compatible with dollops of Crisco (if you are new to the world of condoms, then I understand - if not, you had better research what lubes work with safe sex). The hard object was at the very least my condom that for all intents and purposes ripped off near the beginning of the anal session (and likely those of the men who fucked this stud that day before I did). Who knows, perhaps he was hiding a lead pipe up there too - no clue. He clearly did not take no for an answer when it came to being bare fucked.

I was fucking a guy who asked to be fucked but then complained of the fucking causing him pain around the surgical mesh that repaired a hernia.

Too complex. Way too complex.

Was with a guy who was basically unemployed, although he sold stuff on eBay, He was in his 30s and still living at home. The house had Catholic saints everywhere and he lived in his sisters pink bedroom. He looked fine in clothes but naked you could see deep red, picked stretch marks and extreme sagging from weight loss. He also had bacne and a little dick. I tried to do it, but couldn’t stand having the sweaty, fat slug on top of me. I made an excuse that I don’t like hairy chests. He contacted me later and said he shaved his chest for me. Lol I still get sick thinking about how saggy and gross he looked.

Bump

So many guys don’t know how to fuck or suck. How can anyone be bad at sex? I don’t get it.

But, R133, not everyone can be the stud that you are.

[quote[everyone cheered and threw napkins at him as he stormed out of the club

LOL

whoops.

R127. My friend Andy owns that bar.

[quote]When he finally got that huge thing all the way in he got about a dozen pumps and I projectile shit all over him. I mean it shot out like a firehose.He was of course repulsed,and I was mortified beyond belief.

JESUS, what do you do after? What was the conversation like besides “I’m sorry.” I’m knocking on wood that it’s never happened to me. By the grace of GOD because I’ve certainly thought it was going to. I don’t think I’d have sex for a while if it ever did.

Lived in NOLA for awhile.

Went out with this man, after dinner we proceeded to climb into bed. He picked up a picture of a couple at their wedding reception. He stated this is my brother and his wife. let's masturbate while talking about them having sex. Later heard he was terminated as a teacher from a Catholic school for cussing out a Nun.

A man came back to my place, removed his shirt and said, by the way , I have to inform you. I'M A REGISTERED SEX OFFENDER. BYE FELICIA.

Walked with this guy home from a bar, because he was quite drunk. He came out of the bedroom in a bathrobe and started kissing me. Reached for his penis, it was a half inch at most. I said let's make it harder. He said it is hard. proceeded to tell me if I took him to Commanders Palace for a $400.00 dinner, we could fuck all night. I TOLD HIM, FOR THAT DICK, I WOULDN'T TAKE YOU TO MICKEY D'S.

He cursed me a blue streak while he showered and stormed out R138 ! There was no conversation,and I avoided the bar I picked him up at for a very long time. The sad part is I had worked for a long time trying to get that dick,like weeks! All I can think is he must have hit SO deep it hit something,I had prepped so carefully because he had misgivings about anal sex,having had shitty experiences! I didnt eat for 2 days beforehand,and douched several times.Lesson I learned was sometimes a cock CAN be just too big.

Soooooooo glad I'm celibutt!

when i was six, one of the high-school aged boys used to take me up to the loft of the hay barn, hold me down and fuck me. happened in the woods off the corner of the soccer field, our garage, the attic, my bedroom. i hated him because it hurt but he told me he’d kill me if i told anybody, and a six year-old believes that.

my longest-term boyfriend in college had a dick that was maybe the size of my thumb, and i thought i loved the worthless turd so i’d spend my time trying to get him to let me suck it to try to make him happy. why on earth i wasted three years with him, especially in undergrad...

for two years in my twenties i dated a man-child who wouldn’t have sex with me, like, at all. we didn’t even kiss. again, i thought i loved him, but i probably just thought he was the best i was going to get.

i was wondering if total absence of sex counts as bad sex, but i’ll stick with abusive, cheating worthless turd from paragraph two as the worst.

R142 Gurl,you sound like a nightmare. Your post sorta repulsed me,it was so fraught with neediness.Its not them honey,its YOU.

i don’t need anyone these days, r143.

thank you for your input.

Congratulations, R143, you've won this year's DL award for Most Disgraceful Shit!

R142, please don't blame yourself for being victimized and get some top-notch therapy.

Micropeen, my ass barely felt it and I was only 17 so no jokes about my hole being too big. He was a teacher at my high school and had a bit of a belly, claimed to be 26 but was probably lying. Oh, and he was married with a baby. The wife was the breadwinner and worked late nights, we had sex in his room while the baby was in the next room.

Then there was the Catholic guy who still lived with his parents in his late 20's and was super hung up on sex, his parents really did a number on him. He would fuck me, then afterwards be all judgmental and act like I was a whore. I dumped him after we fucked at his parents place, then he immediately began to sterilize his room with sprays and wipes like a crime had occurred.

R142 i'm so sorry this happened to you when you were a child, and I agree with R146 about therapy. Something like that would mess up anyone and it will help to go talk to somebody about it so you're not living out some part of that trauma and dysfunction in relationships over and over.

R142 that’s not bad sex, that’s rape. It happened to you, not with you. Not your fault.

r149 I understand and agree, but rape strikes me as pretty bad sex, so there we are.

To honor r143’s characterization of me as a needy nightmare, I’ll add one more: the underhung, top-only former football player who would come – in two minutes at most – then immediately roll over and start snoring. He complained that we didn’t have enough sex.

Don't you dare buy into that schmuck's characterization of you. He's the nightmare.

The time I vomited in the guy’s lap. Definitely the worst.

R142/r150 you’re lucky you got two minutes. The guy inserted his dick and promptly blew. I could barely hide my shock. He said it had never happened before. He was so hot, so I gave another chance, but once again, bang, same thing. Tried to tell me that it was a freak coincidence. I don’t think so. I felt bad for him, he was really embarrassed, but I just couldn’t give him a third chance.

R153 I wonder why all the lead up to sex is even worth it if someone only lasts one minute?

R119 simply isn’t getting enough credit for that reaction photo. Too perfect.

Listen bitches,I totally skimmed the whole molestation thing on R142's post,I only saw the 2nd and 3rd part or Id have certainly worded my response differently. Sorry R142,Im a bitch but not that big of one. Mea culpa,and Im so sorry you went through that.

Well, we're not mindreaders, toots.

r156 i had merely assumed that all those large penises you were complaining about had rendered your eyes incapable of focusing at close range.

and yes, i was incredibly needy in my 20s and had no self-respect... but that’s how i had so much bad sex.

the one time i had really good sex, the kind you never want to end, was with a straight-up hoe in san francisco. i was dickmatized, he was ready for his next conquest, it didn’t work out.

Exactly r154. The poor guy though, every sexual encounters must be mortifying. I have no idea if that’s even treatable.

[quote] One guy I was fucking kept saying thank you, thank you, everytime i went into him

I once fucked a guy in a bookstore who mumbled I'm so ashamed I'm so ashamed with every stroke.

What was he reading?

Ah a millenial. There used to be these things called adult bookstores that had glory holes, backrooms, basements and the like.

r16 - similar experience. I was really drunk and brought a cute guy from a bar home but I didn't realize he had some kind of physical problem until we got back to my place and he had difficulty walking up my stairs to my bedroom.

only then did I realize that he had a clubfoot and couldn't walk up the stairs without help. I, of course, made no mention of it and helped him up the stairs, and we actually had a good romp in the hay. I'm not some "ableist" asshole but the fact I didn't notice the clubfoot beforehand is beyond measure. so glad i don't drink like that anymore.

PS: this was not in some 3rd world country, it was in SF, CA and he was American. So how that didn't get fixed as a child is beyond me.

r163, I can tell you how it happens. A coworker's son's girlfriend gave birth to a baby boy with a club foot that was paid for by Medicaid. The doctor said the club foot could be fixed by a brace. When the coworker adopted the grandchild and then became eligible for our wonderful, publicly-regulated-utility health insurance plan, there were all kinds of treatments including surgery to fix that club foot. It's pretty much about the money.

This was not a one night stand, we had been fooling around for a few weeks. He was extremely closeted and wouldn't even admit he was gay. After he came, something he had never done with me before, he started moaning like he was in pain. "I shouldn't have done that" he said, "I think I am going to be sick to my stomach". Then started screaming for me to get out. Get out. Get out.

I guess the sex wasn't really that bad, just his horrible reaction afterwards. Today he is an out happy gay man in a relationship and totally accepting of his sexuality and we are great friends.

[quote]Listen bitches,I totally skimmed the whole molestation thing on [R142]'s post,I only saw the 2nd and 3rd part or Id have certainly worded my response differently. Sorry [R142],Im a bitch but not that big of one. Mea culpa,and Im so sorry you went through that.

This is when the "Sure, Jan" gif would be utilized.

I think this thread is a toss up (a topic that came up often, BTW) between the guy with no hand and the serial farter.

R167 - another vote for the serial farter! LOL

[quote]r162 What was he reading?

Judith Krantz, I bet. At the bargain bin.

[R165] Thanks for telling my store to the world.

R160 as much as that sucked for you, it made me laugh.

R171 It was rather funny, even then. Good lord I've had so much bad sex it isn't funny.

How was it the other guy's fault, R21?

You're the one who poked the lil' brown bears. Hehe.

I've already told the story of the weird character I hooked up with whose house looked fine from the outside, and he had a brand new car to boot-but the inside of the place was so dirty, decrepit and worn out, I half expected to see Ed Gein sitting at the kitchen table with one of his skull cups (g). I sat on my better instincts and allowed him to blow me, he stated that he lived to swallow-well, it felt like I was attached to some sort of extraction machine..I wasn't getting off at all. My inability to orgasm only made him angry, he was cursing at me through his relentless assault on my dick. The sound of that provided the encounter's only touch of levity. I finally got fed up and grabbed his beard, pulled him away somewhat and finished myself off so he could have his "reward", or whatever it was by that stage.

In spite of everything, he asked me to stay the night, but my hands were already reaching for my keys. Very depressing and reflective ride nome. Didn't think about sex for weeks afterwards.

Grabbed his beard and pulled him away. I chortled r173 you made me chortle.

Well chortle my balls!

Well, then the day hasn't been a complete toss-off, R174..hehe.

The story is funny NOW, at least.

R176 I knew a guy, Jewish mind you, who said he held a Hasidic man by his sidelocks when he was being blown. These things come in handy.

R161 "what was he reading?"

"The Confessions of St. Augustine," Rose.

Best thread of 2018

All these sad tales.

Sex really IS overrated!

R178, lol.

Years ago I was at a sex club. It was pretty dark. Exploring one of the room, I saw a cute guy sitting on what I guess was a massage table. I wasn’t sure if he was into me, so I stood on the other side of the room hoping he’d come to me. Waited. Waited. Pretty dark so I guess he didn’t see me or wasn’t interested so I gave up on him.

I hear a big thud from across the room and then see him scooting on the floor. Bitch had no legs.

Multiple Germans who stuck their tongues up my nose. What's up with that? And the one that blew air up my ass while he was rimming me. What's wrong with Germans? I also shit on a guy's dick in a sex club but, to be fair, I told him a few times it was a bad idea. He was a douche so finally I was, like, knock yourself out. I laughed and laughed.

r142 Baby, I'm 60 and I was raped as a kid and I've had a horrible life. I'm finally in therapy and it's really helping. You are worth being loved. Please don't wait as long as I did.

R105 's date was high on meth.

R182 , because of your ass I now have to clean chewed up ham sandwich off my screen. I hope your happy!

R183 - speaking of sex clubs and shit, the Slammer in Silver Lake literally reeks of it the times that I have been there. Judging from the looks and smell of things - every anal sex encounter there involved chili dogs. I have never seen so much bareback dirty-dicking going on in one place - not pretty. Head for the Zone instead

[quote]I'm telling you NOW, so I don't have to tell you THEN.

I'm getting hard NOW, so I don't have to get hard THEN.

There. Fixed that for you R113.

Met a guy through online personal ad, went out for drinks on a Friday night. Back to my place. Kissing and touching later, I asked if he wanted to move to the bedroom. He said he didn't have sex on a first date. Whoop dee doo. He called me the next day to ask if he could come over that night. Having no other plans, I agreed. He showed up around 8 with dinner. Unexpected and thoughtful! We had chicken parm with pasta, red sauce and ceasar salad. Watched a movie, showered, then went to bed.

His dick was okay -- probably 8" but pretty thin. He shaved his balls, which is a turn off, but whatever. I go down on him and he's telling me to slow down after a minute. Fuck -- a premature ejaculator. I stop sucking him and he wants to 69. I'm 6'6" and he's 5'6". Not gonna be easy, but he turns around and starts to blow me. His dick was long enough, so I could take him, too. He tried to deep throat me, something I have never liked, but I figure maybe he's hinting at what he likes. So I take him all in my mouth. He starts convulsing and shooting his load and plunges his head down on me. As his dick is spurting the last of his load, his head spewed chicken parmesan, partially masticated linguine, and red cellulose puke all over my dick, legs, sheets, pillows. He started crying and saying he was sorry. I shot up, ran to the bathroom, and got into the shower. I stayed in there for a more than ten minutes, came out, dried off, and walked back to the bedroom WHERE HE WAS SLEEPING! I grabbed his shoes from the living room, and brought them back into the bedroom, turned on the lights, and yelled at him to get up, get dressed, and get out.

[quote] Judging from the looks and smell of things every anal sex encounter there involved chili dogs.

That comment made me laugh.

I had sex with a woman, once.

Ew.

Never again.

R180 party pooper

R191 I'll say!

Agree - sex (attempts) with women. As a teenager in group party houses. One house we had a slutty girl come over and she was giving blow jobs to everyone in the house. Finally it was my turn and I could not get hard - talk about stress. With all 6 guys watching. So embarrassing.

Another time, a girl dragged me into a bedroom and was all over me trying to have sex. I gave her oral sex for at least an hour hoping I could eventually get hard - but couldn’t. And as you can imagine, thoroughly unpleasant experience. Finally after an hour, one of her friends came for her. She wanted to keep going but I saw my opportunity to bail. My tongue was sore for 2 days.

[quote]With all 6 guys watching

Now, see, THAT would have got me going!

[quote]I gave her oral sex for at least an hour

that was your first mistake right there. OF COURSE it was unpleasant!

Ewwww he licked the kitty cat,

Despite being the premise of so many frat boy gang bang pornos, having other guys stand around and watch is not erotic - just stressful. Even for the straight guys. Especially sexually inexperienced, insecure 18-19 year olds. It’s more of a masculinity proving experience. Once again, porn does not equal reality.

R189, how horrible!

Friend of a friend introduced me to a guy who was obese, like 400 lbs or so. But, I was a horny fat chick with poor self-esteem, so I agreed to go back to the guy's apartment for the night.

I don't know if he was afraid that our combined weights would break his bed, or if it was already broken or was filthy or something, but he didn't invite me to his bedroom. Instead, we stayed in the living room on the carpet.

He wasn't able to successfully go down on me, claiming it was too hard for him to breathe. And when I tried to give him head, his sweaty junk literally smelled like an outhouse and I gagged. And then, we couldn't even successfully fuck, cuz his smaller-than-average dick couldn't reach far enough past our respective fat bellies.

So, we both went to sleep on the floor... or at least HE did, but he had sleep apnea and his loud snoring kept me wide awake, plus the quiet moments between snores when he didn't breathe made me fear he wasn't gonna live through the night.

And then, THEN, after ALL of that, when the sun finally rose and I could go home (had to wait for public transit to start up for the day)... I realised that the stimulation of the previous night had apparently kick-started my period, as there was a puddle of blood on the carpet (not to mention all over my panties). I tried to clean up what I could, but I was exhausted and embarrassed and just wanted to gtfo of there so I left before he woke up.

👆 This is one of the thread’s winners.

Lmao oh R199. You truly are a DL'er.

Agree R199 is a winner. Honest, real and funny.

Yuck, R199.