Unexpected Hookup With A Friend

by Red and Gray

What’s your gender? Man
How old are you? 40s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Manager
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Insatiable
How many sexual partners have you had in your life (including oral sex)? ~40
How many hookup stories have you here posted before? 1

Unexpected Hookup With A Friend

How long ago did this hookup happen? 20 years

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 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? April has a strong Italian heritage, very slim, with long straight brown hair. We had known each other for 8 years at the time of our first hookup. She had been one of my best friends since we first started high school and would hang out together by ourselves or with other friends nearly every day.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? April and I talked about everything. We had a very long history of confiding in each other. I had always been attracted to her but knew her well enough to know that I absolutely wasn’t her type. I was an offensive lineman and powerlifter and she was into skinny and lanky guys with long hair. She married one of my best friends a few years earlier and we started talking during a party about our sex lives. I had nothing going on at the time and she was angry that her husband refused to have sex without a condom. Neither wanted kids but he wasn’t taking any chances. I never wanted kids either and had suffered a traumatic brain injury a few years earlier that managed my pituitary gland and shut down my sex hormone production (along with some other issues) making it impossible for me to have kids.

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? April and I were both pretty drunk and had taken some mushrooms earlier as well so our inhibitions were nonexistent at this point. I joked that I’d help her out by bashing her husband over the head to give him the same injury I had suffered to help their sex life. April’s body language changed immediately and I didn’t know if I had offended her or if something came out wrong in my inebriated state. A slight smile appeared, her eyebrow raised, and she nodded towards the door. I was sure I was misinterpreting the signal but I got up and locked the door.

When I turned around April was sliding her panties off from under her skirt. I got my pants off faster than I thought possible and pulled her to the edge of the bed and slid my cock inside of her. I started fucking her hard and fast knowing that I needed to finish quickly. Under her breath, April was pleading me to cum inside of her and to fill her up which I did. I came hard and pushed myself into her as deep as I could. She pulled me closer and squeezed to get every drop out of me.

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? We composed ourselves and straightened up the room a little before I unlocked the door. I sat down in a chair across from the bed where she was sitting and her husband came in a moment later. I quickly told him to come in and close the door and asked his opinion about some sensitive drama that was going on with another couple at the party to give a plausible reason for why I was alone with his wife in the bedroom.

April and I hooked up quite frequently for a while until a job moved me across the country. We lost touch after that and I’ve heard that they split up a few years later.

I wish we had stayed in contact with each other. Her husband and I had a falling out shortly after I moved over another issue and things got strained. Would love to reconnect with her just to rekindle the friendship we once had.

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), Emotional intimacy, closeness, connection, Intoxication

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Hallucinogens (LSD, mushrooms, DMT…)

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Hallucinogens (LSD, mushrooms, DMT…)

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? Never talked about it with anyone. April and I never discussed it or the future hookups, they just happened when we had the opportunity.

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? Not at all

What was the BEST thing about this hookup? Being able to share physical intimacy with a longtime and trusted friend.

What was the WORST thing about this hookup? Eventually losing contact

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I learned that I get incredibly aroused by being with another man’s wife.

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

All things considered, how NEGATIVE was this experience? Not at all 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 hope casual sex can be destigmatized. I believe this is a natural part of bonding with other people and not solely reserved for pair bonding.

What do you think about the Casual Sex Project? Love reading about the experiences of others.

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