First Fling

by Jason

What’s your gender? Man
How old are you? 56
What’s your race/ethnicity? White / Caucasian
What continent do you live on? South America
What country and/or city do you live in? Rio de Janeiro
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? International Trainer
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I am currently widowed, after a 21 year completely monogamous relationship with my wife.
How many sexual partners have you had in your life (including oral sex)? 15-20
How many hookup stories have you here posted before? none

First Fling

How long ago did this hookup happen? 30 years ago

What was your relationship status at the time? Engaged/Married (open)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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? Lil (not her real name) was a special needs teacher at a school where I was also teaching. She was a wild free spirit, and invited me to visit her in London while my wife was temporarily out of the country. I rode across other house where she was living with her brother and other friends. We sat outside talking and then walked across the park, to a local British pub where we found a quiet corner and started kissing. I was very attracted, and found her wild free nature appealing. She knew I was married, but that she wasn’t there with me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? No planning. Walking across the park back to her rooms, there was a real sexual tension and frisson in the air. When we arrived we went strait to her room and immediately started kissing. I removed her top and bra and immediately began kissing her breasts. She flung her head back moaning and unzipped my shorts taking my penis in her hands.

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 then both immediately stripped. Fingering her brought her fast to orgasm. She then lay on her bed, wide open and I came into her arms. After rubbing back and forth she positioned herself so I immediately entered her deeply. We made love and then fell asleep in each others arms. Awaking about one hour later we then made love again, doggy style and her riding me. She had not had sex for a while and was very active. After we cuddled and talked. I had to prepare a class for the next day, and so regretfully took my leave at 3.00am.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? The next day, I was hoping to meet, but she did not come to school for three days. I would have liked to develop a deeper sexual relationship, but it did not happen. We never spoke of it again. Years later I met her family in New Zealand and discovered she was living in Tampa, Florida. She said that we had a very sweet time together.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have

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 till now

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? it was the second sexual experience of my life. I was very attracted to her wild free spirit and would have liked it to continue.

What was the WORST thing about this hookup? That I didn’t have contact for 3 days after, and could not talk about what happened.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, valued the physical closeness and intimacy more.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? The negativity was only because of the lack of possibility to talk later

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? Wholly positive.

What do you think about the Casual Sex Project? Totally approve

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

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