Tops and Bottoms - What was your worst ever lay?

[YourNoLimitsBottom]

I hooked up with a guy who was better than six inches shorter than me. He wanted me to bend over his kitchen table so he could fuck me, but logistics being what they were obviously this didn't work. So then he wanted me to bend over the back of his couch, which again didn't work. I saw he had straight porn playing on his living room TV and I put two and two together that he was used to fucking women, and probably ladies shorter than he was. He was getting flustered so I convinced him to fuck me missionary. He came and I went.

This is one of the reasons when talking to a guy unseen I stress my height and I like to find tops that are either taller than me or who like positions that will allow them to fuck comfortably. If the top isn't into the fuck, it all tends to fall apart.

AND this is why I like tops that are gay, I know they are interested in fucking ME, and not using me as a substitute for a woman they couldn't get in the heat of the moment. To this day I usually only play with gay men.

[NWUSHorny]

5 hours ago, YourNoLimitsBottom said:

I hooked up with a guy who was better than six inches shorter than me. He wanted me to bend over his kitchen table so he could fuck me, but logistics being what they were obviously this didn't work. So then he wanted me to bend over the back of his couch, which again didn't work. I saw he had straight porn playing on his living room TV and I put two and two together that he was used to fucking women, and probably ladies shorter than he was. He was getting flustered so I convinced him to fuck me missionary. He came and I went.

This is one of the reasons when talking to a guy unseen I stress my height and I like to find tops that are either taller than me or who like positions that will allow them to fuck comfortably. If the top isn't into the fuck, it all tends to fall apart.

AND this is why I like tops that are gay, I know they are interested in fucking ME, and not using me as a substitute for a woman they couldn't get in the heat of the moment. To this day I usually only play with gay men.

I always find it baffling that there are so many guys that only fuck in one position, and if it doesn't work for a particular hookup are completely unwilling to try to find one that works for both guys. Too many inhibitions and a lack of adventurism does not make for great sex.

[J0nn1eb0y]

Though years later we became friendly and fuck buds we had a horrible first time. I was in my mid 40’s. I had only come out at 45 to wife and moved out on my own at 48. I could now be whatever kind of gay I wanted to be. I vowed that I would try everything that presented itself to me and try it 3x before I could say I didn’t like it. I took to fisting rather quickly. 
i made plans to meet up with this sexy German fucker. He wanted loads and to get fisted. At this time I was 100% top. No chems erection that never went down and could cum many times. When he arrived he asked to use my bathroom. No worries. I put on my gear while he readied himself. We started with kissing, then nipple play. My nipples are huge and sensitive. I started to play with his ass which clearly was the entrance to the pig farm. He was so wet I had to eat his ass. I was in his ass deep. Chewing, sucking slurping. It had an odd tangy taste. Clean but not lube or cum as I thought when playing with it. I then stood and pushed him down to his knees. I further pushed his chest to the floor before I slid my Dick in. I didn’t have my Prince Albert at this point. I started to use his ass with a rhythm of long strokes followed by short. At this point my body starts feeling strange. My right hand started to tingle. As I wondering am I having a heart attack. My tongue feels like a dead fish in my mouth. Then my lips and lower jaw line has lost all sensitivity and I couldn’t feel shit with my right hand but with my left my face couldn’t couldn’t feel my hand touching it. I am a recreational hypochondriac. I know the symptoms of every disease. I try to communicate that I might be having a stroke.  I sound like Dick Clark on New Year’s Eve when he is allowed to come out and say “happy do year”. In a final yet crushing blow my Hard on collapses  like a outdated casino in Vegas after the dynamite was detonated. He’s asking what’s the matter with me.  He didn’t have visual contact as we were facing the same direction. He looks over his shoulder and says he’s got to go. Just as well. He leaves. I go to wash up because I believe I may have to go to the ER and in the waste bin I see a used tube of lidocaine. He had put it on his ass in anticipation of getting fisted. That was the tangy. 

[Guest]

As a cumdump bottom and a dues paying faggot, I take a lot of cock and cum in my cunt. I regularly (weekly) take multiple loads from anon strangers and am available for use by any man that wants to breed me.

About 5 years ago I had (what I hope will be) the most unsatisfying encounter. to be fair to the top in question, it wasn’t entirely his failure. On this occasion, I had been hosting ass up in a hotel room and had already taken 7 loads from 6 tops.  My hole was wrecked and sloppy — literally leaking cum.

Top number 7 pushed open the door to my hotel room and positioned himself behind my hole. I didn’t get a look at him because I was head down and didn’t really care who fucked and bred me. But I could hear him undress and, before too long, felt his hand squeezing my asscheek as he began to eat my cummy hole. This normally curls my toes, but in this case, the top just licked it a few times like a popsicle and he finished in less than a minute. But, whatever — a quality rimjob is great, but I was here for cock and cum, and I looked forward to getting fucked.

I felt the top place is hands on my hips as he positioned himself to enter me. I felt his first press against my ass. And that was it. I literally didn’t feel his cock penetrate me or feel him inside me. He began to pound away at my hole, but he was not well equipped, and I felt nothing.

I realized that, while he was tiny, it didn’t help that I was so stretched and sloppy. He didn’t seem to mind and after about 2 minutes he climaxed and (I assume) came inside me. He pulled out and presented his cock to clean off his dick. I opened my mouth and began to suck him clean.  I actually felt badly for the guy; he was maybe 4 inches and no thicker than my index finger.  I finished quickly and he left. 

When I’m taking anon loads — ass up and head down in a hotel room — part of the thrill derives from the anticipation; when I hear that door open, I get excited because I know that my hungry hole will soon be feed cock and cum. In this case, the anticipation was never made real. It was a terrible fuck — my loose, worked over cunt and his pretzel stick conspired to deliver disappointment. It was the cumdump equivalent of eating a plain rice cake — boring, bland and unsatisfying.  

[descartes70817]

The ones who made sex a dismal failure for me all claimed they were experienced bottoms although I think most of them maybe had a pencil dick in his butt and convinced himself that all dicks were much the same. The one thing I hate hearing is "Stop, please, it hurts too much". especially if I haven't bottomed out in his ass yet. I finally reached the position that once my cock is in your ass I'm not stopping until I cum, not matter what happens. So yeah, I've had a few guys shit all over me.

[Bibttmmiami]

I’m a bottom/vers so I do occasionally top every now and then. Back when AOL chat rooms were a popular way of hooking up I met a bottom that sounded pretty hot.  He talked a great game about being submissive and liking to get humiliated ect. When we actually hooked up he turned out to be mostly show with very little go. He was very hesitant to do anything, and when I fucked him… let’s just say he wasn’t very clean and it got messy. That was a total turn-off. Ended up showing him the door and rubbing one out instead. Met him twice, was disappointed twice. The other time we met was at a local spot that was known for hooking up and fucking in cars, both gay and straight people went there. He would barely suck my cock because he was afraid of being arrested. No cops were around and I had mirror tints. He chickened out and just asked me to watch him jerkoff and cum on himself.