by Mr U

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? NYC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? School Counselor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
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)? 35
How many hookup stories have you here posted before? 3

The Only One-Night Stand I Regret

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Single

How would you best classify this hookup? One Night Stand that was supposed to lead to more

How long did you know the person before this hookup? Just met that day

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? Lisa and I met on Match.com, but we recognized each other, and we eventually figured out that we had friends in common. It turned out that we had both grown up in NYC and had attended the same camp, school, and church functions, but we didn’t know each other well because I am two years older, so we traveled in different tribes, so to speak.

Lisa is blond and blue-eyed and about average height. She carries a few extra pounds but carries them well, and she has large breasts.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It turns out that while she works in NYC, she lives in Scarsdale, which is about 20 minutes away when there’s no traffic. She has a couple daughters who mostly live with her, so planning a get-together was tricky. We found a night when the kids were with their dad, and I made a dinner reservation near her place. It was not clear that I would be staying the night — we had never discussed it one way or the other — but I planned for it in case, taking along a change of clothes and a condom.

We met at the restaurant and hit it off immediately; chemistry was great, and we enjoyed each other’s company. I had brought along some photos from our church group days — there had been a yearbook of sorts — and during dinner I mentioned it. She wanted to see it, but I told her I’d left it in my car for later. She correctly interpreted this to mean that I was hoping to go back to her place, and I admitted that I was. She said something to the effect of “I don’t normally do that” but said that she felt comfortable with me, partly because of our shared friends and shared background.

After dinner, we put my car in her driveway and headed into her house.

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? She definitely wanted to make out and maybe give each other oral sex, but she clearly had a different view of penetrative sex than I do. To me, it’s just another way to give yourself and your partner pleasure, but I understand that for a lot of people, it signals a powerful shift in intimacy. Because of this, I made sure to point out that while I was interested in having whatever sex she was comfortable having, I couldn’t make any promises about a second date. I was concerned about the logistics because I was looking for more than a once-a-week girlfriend, and I had recently been in a relationship that involved more travel than I was prepared to do.

She was getting pretty drunk but was definitely not “wasted”. Still, I tried to be extremely clear with her before we headed to the bedroom, and I got the impression that short of ruining the mood, there was not much I could do to be clearer about my feelings and apprehensions. She seemed to understand that this might be a one-nighter, but I think she was hoping it would turn into something much more serious.

In the bedroom, we both took turns going down on each other, though I didn’t come. She was highly aroused but didn’t come right away when I went down on her as she lay on the bed. She was quite aggressive and bold in bed, which I loved, and just sat on my face and grinded as I licked her clit and squeezed her nipples. She came powerfully and squirted all over me — the first time I’d ever been with a woman who squirted. Then it was time to fuck, and we went at it in various positions for a long time (it takes me a long time to achieve orgasm). We didn’t use a condom because she was on the Pill and because we had both recently been tested, so that meant we could go back and forth between fucking and oral sex. Eventually I came, and after cleaning ourselves up, we found some dry spots on the bed and lay down to sleep.

Unfortunately, she snored loudly, so I didn’t fall asleep for hours, and as I lay there, I thought: This is never going to work long-term. I hoped that we could meet maybe once a week for some great sex, but I didn’t see it turning into anything serious.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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 a nice shower together in the morning, and she made breakfast for me. We chatted a bit, and she seemed excited about meeting again, but I said that I wasn’t sure when that could work given the distance and how she generally had her daughters every night. She deflected some of these comments as if to indicate that “we’ll figure it out.” I was too afraid to say that I wasn’t planning to see her again. I should have been more upfront.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) 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), Hoping or expecting it would lead to something more

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? In retrospect, I think she’d say that I had convinced her it was fine to have casual sex if things didn’t work out long-term. So it was definitely consensual, but she was expecting it to turn into something serious.

To whom did you talk about the hookup? How did they react? Many of my friends, men and women. They all agreed that Lisa had made it difficult to communicate afterwards — not answering my texts or calls — and that she had made me out to be the one who had hurt her. They thought Lisa behaved somewhat immaturely afterwards (by not wanting me to talk).

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative).

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? A little bit

Why do you regret this hookup? I should have bit the bullet in the morning (after sex) and told her that I didn’t think there was anything in our relationship more than FWBs. Instead, I hemmed and hawed and led her on to some degree. She ended up feeling very hurt and calling me up to yell at me a few weeks later. She told me that she just wanted to vent and to listen but not reply. I obliged, and I felt bad, as I listened to her, not because she was right but because her version of the story was clearly different from mine. Regardless of how either of us looked at the events of that night, clearly she wasn’t looking for (or ready for) a one-night-stand, and she regretted and was hurt, and I never wanted to take advantage. I’d have rather just jerked off than hurt someone.

What was the BEST thing about this hookup? Fantastic sex, including her squirting. She was a voracious and aggressive lover, and I think that any man who is with her is lucky.

What was the WORST thing about this hookup? Her hurt feelings afterwards.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? After this experience, I tried to be even clearer in my communication with partners. Sex is still something I’m nervous talking about with a partner — I’m not sure why.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Later on, I found out through friends that she had come to view this hookup as a learning experience. She realized that her communication could have been better, too. She was able to move on and to look at the experience in a more positive light.

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