That One Time…

by David

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Jacksonville
Highest education received: Some college (not currently in college)
What’s your occupation? Caregiver
What’s your current relationship status? Single
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)? 1
How many hookup stories have you here posted before? 0

That One Time…

How long ago did this hookup happen? 2 months ago

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 1 to 3 years

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? We met in a support group for adult children who provide hospice for their parents. She is a widow, and her husband was killed by an IED in the Middle East in 2015.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at our workshop and sat together during the lunch break. She was telling me about how she missed her husband and it was hard to take care of her mother without some backup on occasion so she could go out shopping. I offered to help out. Then she asked about me, and I said I wasn’t married, I was taking care of both my parents and they’d been needing help since just after I left college. I never really dated, and hadn’t any experience, sexually, with anyone. She said she was lonely and was surprised that I was a virgin in my 50’s. I arranged to have a service come in and monitor my parents for a few hours and drove to her house about an hour away.

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 did some kissing, and then she could feel that I had an erection, so we took off our clothes. She touched me a bit, and I felt her breasts and pussy. I was surprised at how very wet a woman could get. She laid me back and tried to get me inside her but I came all over her pussy lips and my stomach as soon as she made contact with my penis. We decided it wasn’t going to work, and I needed to get groceries before I went back to take care of my parents.

How sexually satisfying was this hookup? A little

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? I feel bad because I still don’t know what I’m doing. And I’m still a virgin. I hope Cheryl and I can get together sometime for real, and not just for “Pity the virgin” sex attempts.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method, No penetrative sex happened

What were your motives for this hookup? Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely, Didn’t want to disappoint my partner

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? 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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? I told my therapist. And the counselor who looks in on my parents.

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? I don’t know / I’m not sure

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? It was pity sex. An attempt and it Didn’t change a thing.

What was the BEST thing about this hookup? I touched a real live woman.

What was the WORST thing about this hookup? I’m stupid. And it just confirms it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m stupid. I hate the way I live.

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

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

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? I wish I had the opportunity to get out and meet others. Not just for sex.

What do you think about the Casual Sex Project? Others can brag. I can wallow in self-pity.

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