Sex with My Best Friend’s Close Friend

by Dan

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business development
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? No
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

Sex with my best friend’s close friend

How long ago did this hookup happen? 20 years ago

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 1 to 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? My best friend James had a friend called Ann. They met in university and knew each other for many years. James tried to set me up with her once. I was 27 at the time and still in graduate school. Ann was 29 and working. I was not interested, because she sounded socially awkward. However, over time, I was intrigued by Ann because of all the stories he told me about her. She slept with James once, but a relationship between them never happened. She liked to talk about sex. She seemed to have some penis fixation by mentioning how much she enjoyed giving blow jobs to an ex-boyfriend. She also sounded eager to find a new boyfriend. She also had a threesome with another couple out of curiosity.

One day, I saw James with an attractive woman biking across campus. She had an athletic 5′ 8″ build with sassy brown hair and sexy long legs. When I found out it was Ann, I was immediately interested in meeting her. However, by then, James was reluctant to introduce us because of all the personal details he had shared about Ann.

When I graduated three years later, I got a job in a city two hours away. When I was back in town visiting James, I heard that Ann had a long commute to work by bus. I spontaneously suggested we pick Ann up after work and give her a drive home. That was how I met her for the first time. I asked for her phone number after dropping her home, and I immediately followed up with a call to set up a date for the following weekend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We went out to see a movie and then went for dinner. Over dinner, it was not surprising given what my friend James told me about Ann, but it was still unexpected how quickly Ann started to talk about sex and her ex-boyfriend. She said they had a lot of sex because she was very “fuckable.” She mentioned that she was “fuckable” quite a few times. This didn’t come across like she was a sexually confident woman, but as someone who didn’t know how to talk about sex. Still, I was very turned on and went along with the conversation. Our conversation sounded like two awkward adolescents trying to get laid. The only difference was that we were in our early thirties and we both seemed interested in doing something about 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? When I drive her home, she invited me up to her apartment. After some small talk that seemed like we just had to do to get out of the way, we started making out on the sofa. She unzipped my pants and started sucking my cock. While I am not a big fan of oral sex, her enthusiasm and fixation on my cock certainly got me very aroused. I started to return the favor by giving her oral, but her immediate response was “I prefer to have your penis in my vagina.” Her sex talk was always anatomical. She was not into the “cock in my pussy” type of dirty talk. Her openness and style turned me on. We moved to her bedroom. She was quite descriptive about what she wanted. She said “my vagina is still a bit dry” and she wanted to suck me some more to turn her on. Now I could see what James meant when he said she had a penis fixation. I was quite hard over the next few minutes and then she said “I am ready to be fucked.” I penetrated her and started thrusting. She was quite verbal while we had sex: very little moaning but plenty of the F word. I told her she was “very fuckable.” She responded with “yes, fuck me harder.” It was almost comical as we were both swearing away like that, but it was very hot.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 had sex a second time. By then, she was more confident about expressing what she liked. She said she “liked the feel of my penis inside her vagina” and that she likes it aggressive. So the second time, I thrusted myself into her harder. I was able to last longer the second time, so it was even better. I didn’t sleep over. But I did invite her to visit me in my city the following weekend, and let her stayed over for two days. We had lots of sex again. The weekend after that, I stayed over at her place. It went on like that for a few weeks, but since we lived two hours apart, things just ended because of the long commutes.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), 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? 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? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I never told my friend James about this, and I’m glad I didn’t. Judging from my later conversations with James, she never told him either.

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? I don’t know / I’m not sure

Do you regret this hookup? Somewhat

Why do you regret this hookup? I think she wanted a relationship. I never had long term in mind. So I felt guilty about using her for sex, since she was not happy that her last boyfriend did this to her. Looking back and knowing what I know about dating and relationships now, I see that she was a pretty decent and good person. I should have made the effort to have a long term relationship with her.

What was the BEST thing about this hookup? We were both horny at the time and we both had not had sex in a while. We were both fulfilled by the sex.

What was the WORST thing about this hookup? I think she was disappointed that nothing more happened.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Sex with her was a very positive experience, because she was expressive about sex in a very verbal way. It added to my experience on how to be sexual.

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

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

Anything else you want to add about this hookup? None

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 wish I could have more casual sex.

What do you think about the Casual Sex Project? This is very cathertic.

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