Friend’s Ex-Girlfriend



What’s your gender? Man
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Omaha
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Marketing consultant
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Friend’s Ex-Girlfriend

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than 6 months

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 friend’s ‘ex.’ She was about 25 at the time, maybe 5’6″, and fairly lean, with small tits, but a great, fleshy round ass. She has brown hair, with reddish highlights, embraced a bohemian aesthetic, and, at the time, had about a week’s worth of pubic hair growth. I’d first met her through my friend about 4 months earlier, and she became a frequent staple among our group hangouts. We did not get along, and it was our mutual recognition of sexual tension that resulted in the hookup.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My roommate and I, along with a few friends, had gone to the movies. We had invited this friend and his ex-gf/roommate, but they instead opted to meet us at our place afterward. They showed up, and as a group, we all proceeded to get drunk. At one point, I was out on the balcony with the girl, and she called me out on my attitude toward her. I just responded that I got the same hostile attitude from her. She smiled and said it must be sexual tension. I brushed it off with a laugh, but she pushed me against the wall and kissed me. This took me by surprise, and I didn’t want anyone to see but also wanted to continue the interaction, so I moved us into a closet off the balcony. We continued to kiss and make out in there for a few minutes until it gradually ended and we both went back inside. As the night wore on, one by one, people began to leave, including my roommate, who took off for a booty call. It was only me, the girl, and my friend left, and he was passed out on the couch. I went into the kitchen to make a sandwich, and she followed me and sat up on the countertop. I made my sandwich and we made idle flirtatious conversation. I started to eat, and she said it looked good. I started to feed her my sandwich, then leaned in and we started to kiss again (with mouthfuls of sandwich). I started getting really hard and asked if she wanted to go back to my room, at which point she leaped off the counter, throwing her legs around my waist, arms around my neck, and told me to lead the way. After I carried her into my room, I laid her down on my bed. She took off her skirt and top, while I stripped and laid down next to her.

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 started to grope and fool around a bit, and she jerked me off while I fingered her pussy. Then, on a whim, I asked her to get on all fours and asked her if she’d ever had a rimming. She hadn’t but told me to go ahead. I ate out her asshole for a few minutes while she rubbed her clit. Then she asked me to fuck her ass. I had never had anal sex before and didn’t have any lube, or even condoms. Against my better judgment, I lubed myself and her ass up with spit and started to fuck her ass bareback. After maybe 30 seconds she asked me to stop, as it hurt too much. I pulled out, thinking we were through but she pushed me down and started jerking me off again. I asked her to suck my dick, and she obliged, almost immediately deepthroating me. She continued to lick and suck me while squeezing my balls, and I asked her to finger my asshole as well, which she readily obliged. Afterward, I returned the favor, laying her down and licking and fingering her pussy, while she bit down on the fleshy part of my right hand to muffle her moans so she wouldn’t wake my friend in the next room. After a while, she asked me to fuck her, which I did, with her ass propped on my thighs as I slid my cock inside her. She asked me to cum inside her, but by this time my judgment kicked in, and I spurred on her instead.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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? When we woke up, I fingered her again, while she stroked my penis, but neither of us came, and we want back to sleep. After we got up, we found my friend still asleep in the living room, and simply acted as though nothing had happened.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

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

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

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

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? I told my roommate the next day. He laughed, jokingly called me a piece of shit, and ultimately confessed he had fucked her too. Months later, I drunkenly let it slip to the girl’s ex (my friend) what we had done, and he got really angry, essentially ending our friendship.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? A little bit

Why do you regret this hookup? I felt a little like I had betrayed a friend.

What was the BEST thing about this hookup? She gave a great, enthusiastic blowjob, and didn’t hesitate when I asked her to finger my asshole.

What was the WORST thing about this hookup? I was a little nervous for a while because we didn’t use any protection.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really.

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

All things considered, how NEGATIVE was this experience? A little 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? Casual sex can be healthy and fun, so long as everyone involved is on the same page and has the same kind of expectations.

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