First Time With Longtime Friend

by Bert

What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? Texas
Highest education received: Some college (not currently in college)
What’s your occupation? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Spiritual not religious
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)? 70+
How many hookup stories have you here posted before? 0

First Time With Longtime Friend

How long ago did this hookup happen? ~20

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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 had been a longtime friend for a number of years. We had kissed before and been flirty with each other, but never more to that point in time. She has average height, with a slim build, and nice tits.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was in college, in a smaller town about 25 miles from city I lived in. She had invited me to a college party. We were both buzzed so she invited me to stay over at her apartment. She instigated it.

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? She had changed into shorts and crop top. Once she sat next to me, she immediately started kissing me. I was aroused and began to feel up her tits, which got her very aroused. We were both really buzzed and I must have dozed as we took a break from the kissing. Next thing I know, I wake up and she’s sucking on my cock. I didn’t come but after she stopped we decided to get into bed. She pulled my pants and underwear off, but kept her top and undies on. We fell asleep. When I woke up in the morning, I was horny. She was facing away from me on the bed, I started massaging her between the legs. She spread her legs fully for me. I started fingering her pussy, which became really wet. Pretty soon we were both naked and fucking. After I came, we fell into each others arms for a bit. She got up and showered and drove me home.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? We didn’t see each other for a while. We did fuck again a few times later, but it was a few years. I only saw her as a friend, I didn’t think we were compatible for a long term relationship.

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), Intoxication

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

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? Didn’t tell anyone about it.

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? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Somewhat

Why do you regret this hookup? Years later, after we had a number of other hookups, my friend told me she was in love with me. I brushed it off. I think I hurt her in the end.

What was the BEST thing about this hookup? Because we had been so flirty with each other and had kissed, there was a lot of sexual tension between us so it was inevitable. The energy was high.

What was the WORST thing about this hookup? Because we had been wasted, we were both a little hung over in the morning when we had sex so it was not as good as our later hook ups.

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? Somewhat positive

All things considered, how NEGATIVE was this experience? A little 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 had a number of casual sex encounters before and after but because this was a friend, it did make me try to be mindful of other’s feelings. I think casual sex is great if both see it as casual and not as something more.

What do you think about the Casual Sex Project? I think it is great. I will contribute about other encounters.

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