My Friend’s Ex



What’s your gender? Woman
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Eugene, OR
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Sales Team Member
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Christian
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? Played with Women a little
How many sexual partners have you had in your life (including oral sex)? 35ish

My Friend’s Ex

How long ago did this hookup happen? About Sixteen months 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 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? I had actually known Henry for quite a few years. He is a tall, handsome man with light brown skin and a goatee and a few tattoos. He is actually a bit exotic looking. Time was I had known him quite well, he had dated my former roommate for two years. I had always thought he was attractive and I was very attracted to him and Henry was the subject of a few sex dreams. However he was always a close friend’s boyfriend. It had actually been about five years since I had seen him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Henry came into my work as his company needed to purchase some products from mine. He and I talked business for a bit and he then asked me out for drinks so we could catch up. I was distracted the whole time we were talking and afterwards a coworker accused me of having a lady boner. Henry was quite the hit with the ladies at the office.
I met him for drinks that same evening and there wasn’t a lot of pretense. An extra button open and my skirt pulled up a bit was what he arrived to. We talked and chatted a bit and most of all flirted. Henry picked up pretty quickly that I was coming on to him. He finally asked me back to his place.

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? Now I have to admit I went after him and I was very horny. I hadn’t been with anyone since my breakup with my last boyfriend a few months before. Henry and I made out in the elevator and he grabbed my ass a bit. By the time we made it to his bedroom clothes were already half off and my boobs were out. He laid me down and sucked on my breasts a bit before sticking his cock in me. He was quite large and it hurt a little. He kept kissing me throughout and feeling my boobs. I moaned a bit and after he said I got really loud. We actually both finished about the same and I was very sweaty.
Henry wasn’t really too chatty between times but we went again about an hour later. Second time we went was missionary again with him inside me and I enjoyed every second of it. He pinned my arms up and fucked me until we both came again. We fell asleep after and I woke up early and left around 3.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

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? I felt great the next day and had slept with a guy I had wanted to be with for a long time. Over the next month Henry and I ended up hooking up a bunch more times. However a part of me felt guilty, to me a friend’s ex was off limits and I was breaking the rules even though they had not been a couple for years. Under different circumstances maybe he and I could have gone somewhere but i ended up breaking things off a few weeks later. Not sure how I feel about Henry now but i did get to sleep with a guy I had fantasized about.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Intoxication, To feel better about myself, To feel more desirable

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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

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? I would say getting to live out my fantasy.

What was the WORST thing about this hookup? The guilt felt for sleeping with him.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Didn’t really change how I feel about casual sex or sexuality other than that it let me know how much I missed having sex regularly and how much better I function in life when I am having sex regularly.

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

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

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