by Jenna


Gender: Female
Age: 30
Race/ethnicity: White (Nordic)
Location: Western Massachusetts
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Attorney
Relationship status: Married
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12-15
How many hookup stories have you here posted before? None

The Headboard Knocks More Than Twice

How long ago did this hookup happen? 5 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-Time Wonder!

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I was dating a guy who I knew from Law School. I knew him as a friend for a few years and then we found ourselves working in the same building downtown, so we had met for lunch, drink, etc. He was good looking in a slightly nerdy sort of way, taller than me like I like them I didn’t think it would be anything long-term but we had some laughs and eventually gone on a few dates. By the second date we had made out pretty heavily, but his two roommates had come back as we were fooling around on the sofa, so it was cut short. It was clear that we were going to sleep together soon.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had dinner out one night, had more than one bottle of wine and then were back to his apartment. It didn’t take long to realize that we were going to end up in bed. I had been reaching between his legs to fondle his crotch as he drove home, and he was really hard. As soon as we got there I could tell that his roommates were home, but they were in one guy’s bedroom playing XBox and I really didn’t care at that point.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We went into his bedroom and closed the door, and put on some music – I think it was Bob Marley – and started going at it like crazy. He had my top and bra off real fast and I started to give him a blow job to feel him in my mouth. We got into bed and got each other really hot and then he got on top to do me. I stopped him and had him put on a condom, which thankfully he just did without making a big deal. Then he did me with him on top missionary, but with my legs pretty far back around my shoulders. He was slamming into me pretty hard, and the headboard of the bed was slamming into the wall pretty good, and I guess the guys in the next room heard, because I could hear them laughing and eventually yelling at us to slow down. Knowing that someone was listening to me getting fucked like that sent me into a real deep orgasm, and he came right after. 

He got up to go get us each some more wine, and when he came back I could see that the other two guys were right behind him. I pulled the sheet over myself and kind of play-acted shocked that they had walked in. The better looking of the two guys said that he had heard what had been going on and it seemed like I was pretty crazy and did I want a little more company? I have no idea why I said it, but I told them both that they could sit on the floor and watch us as long as they jerked off for me while we were doing it. It took them about 10 seconds to drop trou, and my guy seemed a little dazed. Anyway, I dragged him back in the bed and started to give him head to get him hard, then put on another condom on his cock and got on top, putting his hands on my boobs. I really like that kind of riding. This time it was unreal, because I could watch the other guys staring and pulling on their cocks while I had him inside me, and that just set me off again and again. I’m not usually that multi-orgasmic but this was different. And that headboard was really knocking against the wall! 

After he came, I sat on the edge of the bed and told the other guys to come over, and I jerked them off, one in each hand. The cuter one said he wanted to return the favor, so I spent what seemed like the next hour getting licked and fingered, and I’m not quite sure who was who. I think I came at least once, but it mostly just felt really good and really hot. I think one guy jerked off on me, but I couldn’t really tell.
Eventually all that attention down there was a bit too much and I told the guys that I had had enough, they were too much for me. I think the two roommates had thought I was going to fuck or suck them off, but that was it, and they let it go at that. I hung out for a bit longer, and then I asked my date to drive me home.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I use birth control and he wore a condom.

What were your REASONS for having this hookup? I didn’t think it would go that way – I was just ready to finally sleep with the one guy. But once it all happened, I was really REALLY turned on and did not want to stop.

Were alcohol or drugs involved? If so, how much? Two bottles of really good pinot noir at  the restaurant greased the wheels, if you know what I mean.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? It was him who wasn’t cool about things afterwards. He didn’t call the next few days and when I saw him in the building getting coffee he was really awkward. Eventually, he just let me know that he wasn’t into that kind of relationship and that was that. Like I wanted that every night? I guess he couldn’t deal with a woman who is up front and open about her sexuality. I think he told some people that I was a slut or something, because I’d get a few looks from men and women in the building after that.

To whom did you talk about the hookup? How did they react? I told my sister about it about six months later and she was pretty shocked. Then about a week later she called and said she had fantasized about it with her husband and wanted more details!

Was this a consensual and/or wanted experience for you? For your partner? Yes and yes – but it seems like he just couldn’t deal.

Do you regret this hookup? If so, why? Not really – I’ve never gone that way again, and I’m not looking to – this one just sort of happened. I regret that the guy was such a pussy about it, and that’s about it.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best – a fantasy fulfilled. The worst – that people might think I was a slut.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? I’m not much of a super casual sex person, but this was what my sister would call a real “Penthouse Forum” moment! LOL

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