That Escalated Quickly



What’s your gender? Man
How old are you? 44
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (not currently in college)
What’s your occupation? IT Professional
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? more than a few

That escalated quickly

How long ago did this hookup happen? 16ish years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a year

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? She is about 5′ 6″, latina, super cute, petite, with an amazing smile. She was my almost ex-wife’s good friend. I always found her very attrative, and pleasant. I was told (by my ex) that she didn’t like white guys, and she was her friend so I never gave it any thought.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at a club, hanging out, dancing, drinking, and having a good time, along with other friends. As we were dancing, she was grinding on me a bit, though I still didn’t think much of it until we were close and I went in for a kiss, and she enthusiastically kissed me. We made out while dancing for a while, still taking it all pretty innocently, until a couple more drinks and me (kinda jokingly) asking if she wanted to get a room.

“I have a room. Let’s go!” was her response.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We walked over to the hotel, got in the elevator, and hands were all over each other. We made out, her hand was in my pants, and the elevator door opened. We never selected a floor. The couple that was waiting for the elevator was cool… said they’d get the next one. I thanked them, hit the door close button, selected the 10th floor, and resumed. I had her shirt un-buttoned, sucking on a tit, and a hand reaching under her skirt to find no panties… while she was taking my belt off and saying we should fuck right there.

I turned her around, pulled her skirt up, and rubbed my dick on her pussy. Just then, the door opened. It was our floor. Up to this moment, I forgot we were even going somewhere.
We stumbled out of the elevator, went to her room, and she was struggling with the key as I rubbed her clit. A minute of that and she realized it was the wrong room. Over a couple doors to the right room, in and to the bed, clothes thrown all over, and we were fucking. Missionary. I stopped before coming, and gave her oral. She came really loudly, then we immediately started fucking again.. and again, missionary. I pulled out and came on her stomach, and I immediately slipped/fell off the bed. I stood up, noticed that the room door was wide open and there was an older couple walking by at that exact moment. I can’t tell for sure, but I could have sworn the guy gave me a thumbs up. We were laughing and having a blast.

I closed the door, grabbed a bottle of sparkling wine from the mini bar, and back to the bed. I can’t remember who’s idea it was, but I ended up pouring the wine on her and licking it off, then vice versa.

I went to bring my dick to her mouth, when she told me she doesn’t do that. Damn. OK, back to fucking. I wanted to spoon, but she said she can only come with missionary. OK, not a problem. Somewhere along the way I rubbed her asshole and she LOUDLY said she doesn’t do that either. OK, well, pussy is pretty awesome. She came even louder than the first time. I pulled out and she wanted me to cum on her stomach again, to which I obliged. To my surprise, the volume was pretty incredible. More than the first time. She rubbed it on her stomach and tits, tasted it, and said maybe next time she’d let me cum in her mouth… but no dick in the mouth.

We showered together, kissed a bit, and she said she was probably done for a couple days since she came a couple times and is now too sore. I was pretty erect, which she seemed to still like… she gave me a hand job for a while, but it wasn’t really going anywhere. Add to that there would be no oral, no more vaginal, anal is off the menu… I just enjoyed the touch and the company.

We dried off, and went to bed. She woke me up early in the morning with a (dry) hand job. She went to the bathroom, got some lotion, and continued. I came, but the lotion didn’t exactly feel good: I’ve got a PA piercing, so the lotion gets pulled into the urethra somewhat. She rubbed the cum on her tits again, then got dressed. It was like 6am. We were up to at least 2am. I was wiped out and wanted to sleep… but apparently it was time for her to have breakfast and go to the gym.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We had breakfast together, and parted ways. She called the following weekend and asked me to be her “fake date” to a work event. I’d pose as her boyfriend, which would keep other guys away from her, then we could go have fun afterwards.

I did, and we did. The party was fun, then we went to a hotel room she had and got naked. She actually gave me a blowjob, and wanted me to cum in her mouth. It wasn’t a very good blowjob, but I gave instruction where I could and she tried pretty hard. I later found out it was the fist time she’d ever done that.
We hooked up a couple more times over the following couple months. She wanted to try anal, too, but it didn’t work out too well. Guess that’s another story…

Turns out she does indeed like white guys 🙂

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Birth control pill / patch / ring / injection / implant, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, I was feeling lonely

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A friend of mine. He thought it was great “revenge sex” towards my ex… since after all, we were slowly breaking up at the time. I never thought of it that way at the time, but he was right.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I really had fun with her. I “wanted” her for at least 6 months, but never really gave it any real thought because she was my wife’s friend and I kept hearing how she didn’t like white guys.

What was the WORST thing about this hookup? Well. Looking back at it, the sex itself could have been a lot better, and part of that was probably my fault and my lack of really understanding intimacy at the time.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Looking back at it, there was a nice emotional attachment that was not romantic in nature. Sex could happen, along with there being emotions, and it’s OK if that is the entire extent of it.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I kinda forgot all about the experience, and to some extent her, until writing this.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? It’s great.

What do you think about the Casual Sex Project? The more I write, the more I like it. I’m remembering past experiences, sharing them, re-evaluating how I feel & felt at the time. I also enjoy reading other’s experiences.

You have a hookup story to share? Submit it here!