u/BiFunMA

Back when I would top and occasionally now with groups I see a bottom whose hole has clearly been used. It’s shaped differently and swollen.I think it’s so beautiful. How did you get there? Over the past couple years I’ve been pretty active but I don’t see any of that happening.

Probably 2011 or 2012, I was in Santa Barbara for work. My afternoon flight out was canceled so I had an extra night with nowhere to be the next day but the airport. I'd been hooking up with men here and there for probably ten years at that point, two or three times a year when I didn't have a gf. It was also the era of Craigslist and casual encounters, so I posted there, and after sorting through some flakes I had a guy on the way to my hotel to fuck me. The whole thing was okay. He checked most of the boxes, reasonably attractive, clean, average cock. He was also visibly nervous and not much of a talker, and sort of rushed through everything but not in a fun, I'm just going to fucking use you kind of way. He couldn't have been there 20 minutes and we were done. He was also really worried about the condom, which I understood but didn't really help the mood.

So then I was alone again, and the way we had fucked I had just started to get into things when he finished, so my ass was sort of buzzing and I had no way to release that. In the past I would've just jerked off or cammed with someone or just gone to sleep but I was just horny enough not to. It was late, and I didn't want to invite someone else over because the odds of it being any better was low and the hotel was small enough that while the guy at the front likely didn't care I didn't like the idea of running another guy up to my room.

What I had also noticed with my Craigslist post was that there was an adult video store like six blocks away. That also made me nervous - I'd only hooked up in hotels and occasionally at someone else's place and it felt sketchy and like a bad idea, so I ultimately decided to just jerk off but as I got things going and my finger slid over my still open hole, I changed my mind. My head was swimming with nervousness and excitement on the walk to the video store.

It was pretty quiet when I walked in, just a couple looking at toys and it seemed like I'd probably be back at my hotel pretty quickly but I didn't want to lose my courage, plus I still really fucking horny, so I went back to the video booth to unload and at least add that to my list of things done.

It wasn't as quiet back there, though. A couple of guys were standing around, and some of the booths were definitely occupied. I didn't know what to do and it didn't seem like a q and a kind of vibe, so I found an empty booth and put on a video. I had barely started when a cock appeared through a glory hole to my left. I don't know why it seemed surprising but it did. It disappeared for a moment and I thought I lost my chance but then it was back. I didn't miss the opportunity. Sucking anonymous cock in a sketchy video booth got me immediately hard but I chose not to jerk off an instead just focused on sucking. I was inexperienced enough that I really only knew how to take my time, I liked to kiss and nibble and lick. This wasn't that. The guy on the other side was basically fucking the glory hole and therefore my mouth. I decided to just go along for the ride until he unloaded and quickly disappeared.

I gathered myself for a moment. I was in a random city at 130 in the morning, on my knees in a video store having just sucked off a stranger. I didn't feel badly but it was weird. After a few minutes I got up to leave. My cock will still hard but it seemed like a good idea to get back to the room - I had done this thing and could definitely jerk off when I got back. When I stepped out into the hall, there was another guy there, he hadn't been there on the way in, and he looked at me and was rubbing his cock through his pants.

Then the urge returned. I came down here because I wanted cock, and it was, right in front of me. I took a step back into the booth and he followed. Again, I was on my knees, unzipped him and got his pants down so I could put my mouth around it. He was leaking a ton of precum, and I focused getting as much of it as I could. He wasn't huge but he was bigger than me and cut with a nice fat head.

After a few minutes he pushed me off him. At first I thought he was going to jerk off onto my face, then when he didn't I thought maybe I'd done something wrong, but then he said stand up and turn around. His arms were around me from behind, and he kissed my neck for a minute and sort of pushed me up against the wall and his hands were at my belt and pants. He yanked them my hips, and I pushed my ass back into his cock. His hand cupped under me, between my legs, and I'll never forget the feeling when he pulled his hand back - he pressed his finger hard against my hole, not in it but around it and I knew he could feel that it was open the same way I felt it earlier. Then he stopped again, and I thought he was getting a condom but then his finger was back except it was slippery with lube. He rubbed it all over and around my hole, then slipped his finger in. It disappeared and he was back with more. I reached back with one hand and tugged gently on his cock. There was no condom. I don't want to romanticize it - I knew it wasn't a good idea and I knew that I could either stop or just suck him off and I thought specifically about leaving and how it would feel nice to wake up the next morning and not worry. I didn't. His fingers were inside me and the next thing I knew they were gone and his cock pushed in. It was not at all like the guy I had in my hotel room earlier, and he wasn't even much like the guy I started hooking up with here. The kissing was done, there were no hands around me - they were on my hips and he was fucking me, hard. Even then I thought, I'll make him pull out but I didn't. After a couple of minutes he was still going and I could feel my ass opening up and giving less resistance, and a few times he came all the way out and I heard that wet sucking sound, and then it was over. He went as deep as he could, and stayed there, then after a minute a few small, short strokes before he finally pulled out. I hadn't even caught my breath and he was gone.

Anyway, that was the first time I basically lost my mind in pursuit of cock. Not the last time either but I'm a lot smarter about it today. It was still amazing, though, I remember so many specific things.