Odd Interlude With My Best Friend

by Benny van Dergast

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineer
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)? 8
How many hookup stories have you here posted before? 0

Odd Interlude With My Best Friend

How long ago did this hookup happen? 13 years ago

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

How would you best classify this hookup? No hookup

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 was my best friend, outside of my marriage. Odd, since people usually think of a man’s best friend to be either a dog or another man. She was recently divorced, three years older than me. We’d never ‘hooked up’ before. She was almost the same as family to us — even going so far as to being our son’s Godmother.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were all on a family vacation; she came along because she was as close to us as family; there was no planning. She and I were the last ones awake in the downstairs common room after everyone else had gone to bed. There wasn’t any instigation; we just were talking one moment, and then the next moment — we were kissing.

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 kissed; open-mouthed. Something that had never happened between us. Then I had my hand on her leg and moved it up until I was resting my hand between her legs, over her underwear, under her skirt. I moved her panties to the side, and then fingered her clit to orgasm; there was no deeper penetration than that. After she came, she offered to go down on me and had just taken my penis in her hand when we had to stop because we heard other people moving in the house. After the other people left, she asked to watch me masturbate; I got hard, and masturbated, even going so far as to rub the tip of my penis against her vulva at one point, but I was nervous about the other people coming back and did not have an orgasm, myself.

It felt natural to me. I’d never had a casual hookup or one-night-stand or an affair, ever before; and she was my best friend, although there’d never been any sexual activity between us before. The emotional aspect of it was very much Love, and I was feeling a thrill I thought I’d never feel again. Nor have I felt that way since.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, not even close

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? We still felt the thrill of having it happen, the next day. We went so far as to talk about having my wife join us (they were good friends, as well), and my wife and I had talked about bringing another couple or a lover into the bedroom with us (but have never acted on that before).

We hoped to have it happen again sometime. How do I feel about her, now? I still love her and long for her. But she passed away (at age 47) a few months later.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Attraction to partner(s), 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

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? Somewhat

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; I’ve never spoken or written about it, before.

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? 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? Not at all

What was the BEST thing about this hookup? I felt very close to this wonderful person, my best friend.

What was the WORST thing about this hookup? That it wasn’t repeated or can ever be repeated, as she has passed away.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I don’t think this has changed how I feel about any of this; I felt like I was desired, not just loved. I wish I could feel that again.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I miss her so much.

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’ve never had ‘casual’ sex, as is commonly said; it’s always been part of a relationship. This was the most amazing one-time-only experience I’ve ever had.

I grew up seeing the older kids having casual hookups in the 70s and early 80s, but AIDS scare blew up in everyone’s faces by the time I reached my late teens — heterosexual kids, as well as the LGBT community, were all shut-down at that time. No experimentation or casual hookups in college for the same reason. After college, I got married.

What do you think about the Casual Sex Project? I think it is depressing for those of us who never really got a chance to have it.

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