[m] My first one-night stand was so weird

I went to a wedding in Portland, Oregon when I was about 28, and I was supposed to go with a girl I had been dating. We dated for about 6 weeks and she left for a 7-week creative writing program in England. We stayed in touch almost daily the first 4-5 weeks before the emails started thinning out. Then the last week she was there: nada.

The reason? She fucked a guy named Teddy and liked him. Now they were dating. Seriously. Yeah, so Jen and I were supposed to go out west to this wedding (had the plane tickets and everything) like 3 weeks after she got back. Well, um, nope.

So I went solo. Only really knew the guy getting married (good buddy from HS) and like 3-4 of our friends, all of whom brought dates. I was the only single guy at the table. So awkward.

Halfway through the wedding reception, one of the bridesmaids (Sarah) I had been talking to came over to my table. I was sitting there just nursing a beer and honestly waiting for the thing to end. She was barely 23 — recent college grad, cute, brunette, big rack, decent body and nice little dimples. Not smoking hot, I thought, but on a tough-grading scale, she was an 8 or an 8.5 on a good day.

“Shot?” she asked. Sure. Why not? So we did a shot and I didn’t immediately have much else to say, even though she and I had talked earlier a tiny bit after being introduced. I guess I was drunk, tired, frustrated, thinking about how broke I was at the moment … so I had little game right then. She kind of wandered off eventually, and I assumed I had blown it.

Everyone ended up back at the hotel, and a party ensued in my friend’s room. People were drinking and getting stoned and shooting the shit — maybe 15 of us total. Then it ended up two couples (the one staying in the room included) and me and Sarah. Then the other couple left. Sarah and I awkwardly took our cue and walked out.

She did the whole “I’m trashed” defense-mechanism thing, and sometimes that means “you can have me” but I definitely took it to mean her saying “I want to pass out soon.” I tried as best I could to stave that off. “Want a nightcap?” I asked her. She reluctantly — and I mean it took her at least a minute to decide — agreed.

We went back to my room and finished a joint and drank from the bottle of bourbon I bought the night before when I headed back from the rehearsal dinner early by myself. She was getting hotter the more I drank. She was still in her bridesmaid dress and asked if I had a pair of boxers and t-shirt to change into. “But that doesn’t mean you’re getting laid,” she added.

She changed in the sink area (not all the way in the bathroom), and in the reflection I could see her tits as she took her dress off. They were huge, way bigger than I realized, and I wanted to bang her even more. I must have been drooling because she basically called me out on it. “I know you want me,” she said.

“Well, yeah, of course” was all I knew to say. She just sat there for a minute. Not saying anything. “Can we smoke in here?” she asked. I said yes, even though it was a non-smoking room. We both had a cigarette and fruitlessly blew the smoke out the cracked window, with most of it staying in the room. She didn’t say a word to me almost the whole time we smoked.

Then: “Ok, fine.”

That was it. That was all she said. She meant I could fuck her. That’s all, just this stone-cold response like 5 minutes later. Then she said, “Most guys want me, I get it.”

What the hell did that mean? Instead of figuring it out, I put the cig out and kissed her. She definitely didn’t reciprocate openly at first but then got into it. Next thing you know we are naked and I am going down on her. She took forever, I’m guessing 20 minutes at least, to cum. It was getting tough for me by the end. She made a little noise and said, “I’m cumming” but didn’t go crazy like some girls do when they’re wasted.

Then she had that look of wanting to pass out, but I had a different look: “What about mine?”

“OK, but don’t take forever to cum,” she said.

Thankfully, I’ve always been a fast cummer. Even with a ton of whiskey, I knew I wouldn’t go very long. Longer than if I had been sober, or just stoned — guessing I ended up lasting maybe 4-5 minutes — and I pulled out and shot it on her stomach. She seemed fine with it.

“Feel good?” she asked, sounding way more slurred now. I said “yeah” and next thing I know I was passed out cold. We woke up and felt guilty, but good lord, she didn’t. She woke me up at 7:45 (we passed out after 3) and said, “The breakfast starts at 9, and I have to be there. Want a quickie?”

About a minute later, after giving me enough of a blowie to get my dick wet to slide inside her, she was climbing on top of me. I guess because I had sobered up more or that I noticed that she was actually a lot hotter than I realized, I kind of lost control fast. I think she rode me for a minute, maybe two, when I started cumming.

“Jesus,” she said. “Did you cum that fast last night? I don’t remember.”

“No, it was longer,” I said, trying to save face for my premature ejaculation. “I got you off first with my tongue.”

She literally said nothing and shrugged. We went to the lobby to have a cigarette and it was quiet and awkward, with little eye contact either. She went back to her room and showered, and I did too, and we both went separately to the breakfast. I sat at the friends table, saying nothing about the hookup to anyone else, and I kept trying to make eye contact with Sarah. It was like she was trying not to look at me.

But you know how guys are. We still think we are smooth. I sneaked up behind her and said, “You know, I still have the room for another hour before I have to check out and get on a plane.”

She laughed. “Nah, I don’t think so,” she said. “I think that was our one night together.”

“Wow, was I that bad?” I asked, knowing full well that she only remembered the quick morning ride from, oh, about an hour before.

“Well, not bad, I guess, but really, really fast,” she said. “I know I said ‘quickie,’ but I prefer guys who can hold it way longer than that. But really, there’s a guy back home I am thinking about. It was fun, though, thanks.”

And that was it. I literally never saw her in person again. Fast forward like 5 years and I saw a picture of her at her wedding; the wife of the Portland wedding couple had liked her photo on Facebook and it showed up in my timeline. Sarah still looked hot, and her husband looked like a douche, but that’s what all guys say when they see the new husband of a girl they once fucked.

I just always regretted not being able to follow up on her. She turned out to be either the hottest or the second hottest — depending on when you ask me — girl I ever banged. I will jack off to the memory of that quickie at least once a month still to this day. Sad but true.

Source: reddit.com/r/gonewildstories/comments/326hpy/m_my_first_onenight_stand_was_so_weird