Quick Sex

by Dan

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business development
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 3

Quick Sex

How long ago did this hookup happen? 2009

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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

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 had to come to a low point in dating. I was on several dating sites, going speed dating every week, and nothing was working. After 40, I noticed a substantial drop in opportunities. I met Susan at a speed dating event. She looked beautiful: 5’7″,120 pounds, long curvy blond hair, and she dressed in a conservative yet stylish white dress. During our dating round, she came across as intelligent although she sounded a bit sad. She was divorced recently. To my surprise, we got a match. I found out she was 40 years old. While I had nothing against that, I wanted children in my future. She seemed too old for that. She told me she also wanted children, while her ex-husband did not. She was hoping now to start over. She also revealed that she picked everyone at the speed dating event, and she was glad I also picked her. My heart sank when I heard that. I also wondered: if she was such an attractive woman, did the other guys figure out something about her that I did not? I still followed up with a dinner date, since I thought she was such a beautiful woman. I picked a hip local neighborhood restaurant. I wore my best Italian leather shoes, designer jeans, and dress shirt (she told me later that I looked really hot that night). She arrived at the restaurant 30 minutes late. The dinner was fun, and we had a good conversation. As we left, I walked her to her car, and then she gave me a long kiss. It was so passionate, it gave me a hard-on. She said she looked forward to meeting again. Since I’ve been dating so long, I’ve gotten to know other single guys on the dating circuit. Her name came up a few times as I talked to these guys. Based on the description, I was 100% sure this was Susan. However, I never told anyone that I knew her. A friend of mine with similar tastes in women as me told me that he went on a date with her. He told me she was neurotic. At a later speed dating event, I saw three guys from the last event, and we debriefed about the last event. One street smart guy said this woman Susan was attractive but clearly screwed up, so he never picked her. Alarm bells were going on in me. Still, I had a second date with Susan. This time, we had dinner at a fancy Thai restaurant. After dinner, she asked me to drive her back to her car. As soon as we got in my car, she kissed me passionately again. This time, she also started fondling the bulge in my pants. This went on for quite a while before I dropped her off at her car. The progression of events all felt so contrived.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On our third date, she was wearing slim fitting slacks that showed off her long legs and tight ass nicely. We spent the afternoon walking around a neighborhood art festival. She suggested we go back to my apartment afterwards.

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 started talking over coffee, and then she started kissing me passionately. This led to more foreplay on the sofa, and then we moved up to my bedroom. I took off her clothes to see that she was wearing sexy lingerie underneath. Her pussy was already very wet, which turned me on. I started fingering her, which got her juices flowing even more. I licked her delicious juices from my fingers as I went to get a condom. We started having sex. I started slowly, since it was a long time since I last had sex. I wanted to make sure I was ready, but I couldn’t hold it. I orgasmed within a few minutes of penetration. She was disappointed and seemed nauseous. She got dressed and left almost immediately.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? She called me up a few times saying she was sorry about how the last date went. I was sure that my poor performance turned her off, but she did not say that. She told me she was sleeping with another guy, and told me his name. I knew this guy! All the things I heard about her that gave me alarm bells started to sink in. On the other hand, she also had this vulnerability that drew me in. I was hurt that she did not want to see me again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? She drew me in with a neurotic, sexual neediness.

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? I didn’t say anything. However, she called a guy (Adam) that she met on a speed dating event to ask for his advice. She told Adam she met me (she gave Adam my name), and she thinks she hurt my feelings, and she wanted to know what to do. She didn’t know that Adam and I were friends. When I saw Adam at a future speed dating event, he was standing around a whole bunch of other men. He just blurted out in front of everyone: “hey this Susan called me up. It sounded like you guys slept together. What happened?” I told them we had sex, and then she ghosted on me. Everyone laughed. Adam paused, thought about it for a few seconds, and then he said, “I’m proud of you!” We all had a good laugh.

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

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

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Somewhat

Why do you regret this hookup? First of all, I think it is always good to get laid. I don’t regret that part at all. I should have kept my feelings in check. Here was someone that I was not interested in, but I went along with it because I was at a low point in my dating life.

What was the BEST thing about this hookup? I got laid.

What was the WORST thing about this hookup? I should have practiced (masturbated) so I could have reconditioned myself to last longer, but I never saw it coming, no pun intended. It was over two years since I last had sex when we hooked up. Also, I noticed all the guys she hooked up with, including the guy she eventually married a couple years later (saw on her Facebook page), were not very attractive at all. A beautiful woman like that could do better if she had better self-esteem. It made me think that maybe I am not that attractive either!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Casual sex is no different than relationships in that you can get hurt in either one. Getting hurt is a part of maturing and learning. In this regard, casual sex is well worthwhile for emotional growth.

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

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

Anything else you want to add about this hookup? It impressed upon me the importance of good sexual performance. In my next hookup, I went the other extreme and had a marathon session. I really want to share those details, which I will post in the future.

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? We need to view casual sex more positively. When it is so hard to get a relationship these days, casual sex provides an excellent if not better alternative.

What do you think about the Casual Sex Project? A great opportunity to introspect and learn more from recalling and thinking about my past expereinces.

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