by Sarah

Gender: F
Age: 40
Race/ethnicity: White
Location: Tokyo
Highest education received: College degree (eg., BA, BS)
Occupation: IT Sales
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? No
How many hookup stories have you here posted before? 0

Impotent Over the Ex

How long ago did this hookup happen? 1 year

How would you best classify this hookup? One night stand

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? Met through a dating site. First emailed, then texted and then sexted over a few months before meeting up as our work schedules kept interfering with plans to meet. He was a 25-year-old personal trainer and had sent many very hot photos of himself, and I had sent one or two on his request.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met for coffee but it had been more or less decided before meeting that we would hook up if the other person agreed. It was clear from all the messaging that we had nothing in common aside from the older woman/younger guy fantasy.

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 to a hotel and stripped as soon as we got in the room. He put on a condom almost immediately, and we started having sex. He was very rough and frenetic. He kept changing positions without giving me any indication how he wanted me to move or what he was trying to do. It was very awkward and uncomfortable. After about 10 min, he suddenly lost his erection and stopped. He apologized and said he wasn’t over his ex-girlfriend and couldn’t do this. I started to give him a massage to help him relax, but even with lots of stroking, he couldn’t get hard again.

When I gave up, he said he wanted to leave, got up out of bed, and started dressing without even checking if he could do anything for me. I was stunned by how brusque he was but got up and dressed too.

It was a huge disappointment after all the months of buildup, but I said some reassuring things about his problem because I felt sorry for him being so young and messed up.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom. When he lost his erection, he pulled out but the condom was stuck inside. He freaked out even though he hadn’t cum. I eased the condom out myself. We had not discussed STI history.

What were your REASONS for having this hookup? I thought it would be really fun and an ego boost to be with a hot young guy. The messaging over months had been intense and super sexy. I thought our chemistry would be incredible.

Were alcohol or drugs involved? If so, how much? None.

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? I thought the situation must be really embarrassing for him so I said some reassuring things in the hotel room and then some more as we left the hotel and walked back to where we had met. He said ‘thanks for being so great about it’ a few times, but I felt really miffed that he didn’t care at all about my pleasure and had not given me one compliment about my body or looks in the hotel or afterward. It would have felt nice to get something out of being with this hot young guy but he was completely lost in himself and his memories of his ex. I was really annoyed that he built up my expectations for months and still don’t understand why he went through with meeting up with me if he had all these mixed up feelings for his ex. I guess he just didn’t realize how he felt about her. I was really glad he didn’t cry. He said the breakup was a couple years before he and I got together and that I was the first person he had had sex with since her. Since this is now a year ago and three years since they broke up, I hope he has gotten himself sorted out by now.

To whom did you talk about the hookup? How did they react? One friend. She said the guy sounded like an immature asshole.

Was this a consensual and/or wanted experience for you? For your partner? Yes, though he changed his mind.

Do you regret this hookup? If so, why? Yes, because I was so kind to him and felt like he didn’t consider my feelings at all by his words or actions.

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? The sexting had been a lot of fun but I would never hook up with a stranger again. Though he said losing his hard-on was about his ex, I did wonder if I just wasn’t hot enough for him. My self-image took a bit of a dive for a while.

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup or anything else? Although this was just one isolated experience, I realize this kind of thing is not for me. I was unprepared for what happened and how bad I would feel looking back at the whole thing.

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