by

What’s your gender? Man
How old are you? 69
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retired
What’s your current relationship status? In a serious relationship (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)? 16
How many hookup stories have you here posted before? 0

Just Once

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For more than 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? She (D) is a year older than me. Very attractive, short wavy blonde hair, tall and a figure any woman would be proud to have – flat stomach, nice ass, and perky C-cup breasts. D modeled professionally when in her twenties. I first noticed her at a sit down dinner party attended by a about a dozen people – I could not take my eyes off her. Months went by before I managed to engage her in simple short conversations on the street.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Yes I suppose it was planned and I did the planning, though the process was took months; lots of little steps. We both lived in a coastal Mediterranean town and her place was a mile outside the town and somewhat isolated. I started by inviting myself to take morning walks with her from her place; we had both previously been on 10K weekly hikes attended by two dozen other people. After walks we’d share tea/coffee and conversation. After a week or so we would take sunset walks and finish with wine or G&T and romantic music. From behind, I started by rubbing her shoulders and neck, unbuttoning the top two buttons of her blouse and sliding my hands to the sides of her breasts, but did not touch the nipple. I kissed her cheeks and nibbled her earlobes, she asked me to stop; I stopped briefly then continued; she was getting very turned on. That is as far as we went that evening, though before leaving I asked if she would kiss me goodnight – I asked for a real kiss, a ten second kiss, not just a peck. We kissed several times, though she was holding back. D left the country for several weeks and upon her return, we met again for sunset walks, wine, and shoulder massages. This time the bra was removed and I caressed her breasts and she kissed me willingly.

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? D suggested we move to her bedroom. We each freshened up in separate bathrooms; I waited in her bed, she came in and dropped her robe and slid beneath the covers. We kissed and fondled each other. I kissed and caressed her body slowly giving her oral sex, which she seemed to enjoy very much, though she made no attempt to reciprocate. I had difficulty penetrating her even though she used lubricant. In fact she found it quite painful, so penetration was very shallow, slowly, gently going deeper in. D probably suffered from dyspareunia. The inability for us to have full on rock and roll sex frustrated her. Anyway, in the end, I did fully penetrate which caused a massive orgasm for me, but a shot of pain for her. She later rode me vigorously to climax herself, though no penetration.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 was in a rough spot with my girlfriend and so I was exploring an alternative situation. We slept together four or five more times, but never attempted penetration again. D has left the door wide open for a future relationship, but I have reconsidered and have chosen to stay with my girlfriend. D and I are still friends, though the situation is a bit awkward because D and I share the same circle of friends and “the hookup” is our secret.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

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? Small amount of alcohol or drugs, not enough to feel it

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? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? I don’t like to think I may have hurt her feelings – disappointed her by not continuing our relationship.

What was the BEST thing about this hookup? intimate touching

What was the WORST thing about this hookup? Little to complain about

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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 jealousy did not exist – I would like to do more.

What do you think about the Casual Sex Project? Interesting to read and learn what others think and do

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

Comments