by Pops

Gender: Male
Age: 38
Race/ethnicity: White
Current location: NY
Highest education received: College degree (eg., BA, BS)
Occupation: Writer
Relationship status: Married
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? Seven vaginal, plus others
How many hookup stories have you here posted before? Two

Crossing the Line

How long ago did this hookup happen? Eighteen years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends with benefits

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 a friend, and my buddy’s girlfriend of several years. We were from the same small town, and my friend and I had recently gone away to college in other towns.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had come to visit me at my school and spent the night in my dorm room while my roommate, who happened to be the son of a Russian oil billionaire, was away for the weekend. It was not the first time she came to stay with me (she had a bad home life) nor was it the last. Nothing happened that night, but for some reason the next day things fell into place.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? When I woke up, she was in bed with me. We talked quietly, and eventually kissed. Things took off from there. There was some oral sex, and we moved on to vaginal in the usual positions. I was her second partner, she was my fifth. We didn’t do anything kinky but the experience was memorable for me because she had her first orgasm while we were in missionary position. It was pretty extraordinary to watch her be taken away by this powerful feeling she had never felt before. Apparently my friend wasn’t very good in bed.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. Neither of us had condoms and she wasn’t on birth control. She asked me not to come inside her, and I complied. I think the feeling of bare cock is what got her off. 

She later got a diaphragm because she didn’t want me to have to pull out of her any more. The first time we used it, which was the first time anyone came inside her without a condom, was a life-changing experience for her. She made me go twice more that night.

What were your REASONS for having this hookup? Young, horny and breaking a long dry spell. On both of our parts.

Were alcohol or drugs involved? If so, how much? None. We were drinking beer and probably smoked some pot the night before, but we were sober when we woke up.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We continued to hook up through the spring and summer. After the semester ended she would come to my apartment or we would find a place to do it outside or sneak away at a party for a quick fuck. Always bareback. She insisted.

To whom did you talk about the hookup? How did they react? No one. My sister walked in on us and caught me cumming in her mouth on my birthday, but quickly shut the door and didn’t say anything. For obvious reasons it had to be a secret. Until it wasn’t.

Was this a consensual and/or wanted experience for you? For your partner? Yes, on both of our parts.

Do you regret this hookup? If so, why? Yes. My friend, her boyfriend, became suspicious and confronted her. She admitted the truth. He was too passive-aggressive to confront me and kick my ass, which I deserved. We never spoke again. She and I are still friends. My wife knows what we did all those years ago and is not happy about it, even though she lives 2,500 miles from me and we are social with guys she slept with before our relationship.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Giving a young woman who didn’t know she could enjoy sex her first orgasm. Her reaction when I went in as deep as I could and came inside her for the first time in her life. Giving her that satisfaction made what we were doing almost worthwhile to me. 

The worst was losing a good friend. He didn’t deserve that. I was later cheated on, repeatedly, by a long-term girlfriend who had given me her virginity. I guess I got what I had coming to me.

All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup or anything else? Don’t fuck your friends’ significant others, unless they ask you to. True friends are few and far between in this world. Sex is easy and cheap.

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