Sex With my Best Friend


What’s your gender? Woman
How old are you? 18
Highest education received: Some college (currently in college)
What’s your occupation? N/A
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? I’ll try anything once
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? None

Sex With my Best Friend

How long ago did this hookup happen? Yesterday

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

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? She is a full blooded Mexican, and also eighteen years old. She has brown eyes, and has thick, long black hair. She is quite petite, and is very beautiful. I think what makes her even more attractive though it that she is very genuine, and very sweet.
I’ve known her for 10 years, and we are best friends. We have never hooked up before, however, we have made out drunkenly before. We are both heterosexual though. She is currently in a relationship, but I am not. I have never seen her as more than a friend though, much less any other girl. My sexuality is a bit complicated. I consider myself heterosexual because I can see myself both sexually and emotionally with a guy, but I can sometimes see myself with a girl but only sexually. Additionally info: previous times that we’ve gotten drunk she has tried to kiss me, but I couldn’t; and only drunkenly have we ever talked about hooking up with a girl just to see what it was like (because she said it looked so passionate and intense); the night before we had gotten high at the park, and we got on the topic of lesbian porn–she asked me if I had a favorite. I was reluctant so show her, because I didn’t want her to think I was weird. So we started watching it, and then she leaned in on my shoulder. It felt comfortable.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began at my place, and vodka led to it. I don’t think I could have hooked up with her without the alcohol. There was no planning, it just happened. We were in the bathroom doing something, I don’t remember what now. I was standing against the wall listening to her and watching her look at herself in the mirror. Then she looked to me and said no one has to know if anything happens between us, or you know nothing has to happen. Then I said I don’t care, but you are in a relationship. Then she pressed up against me and started kissing me.

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? She pressed me against the bathroom wall and started kissing me, then took my shirt off. Then started kissing me. She is sort of a rough kisser, but I think she was just being passionate. Then I took her shirt off, and we started to do stuff to each other above the waist. Then I took her pants off and started to eat her out, then I laid her down on the floor and did it. Then she did it to me, and then I did it to her again. I laid her on the floor, and said there was something I wanted to try. I remember I kept giggling, and I tried to scissor with her. It didn’t really feel like anything to me, but she seemed to like it. So then she said let’s move to the bedroom. And we did. I continued to eat her out, then finger her and rub her. Then she turned me over. She was on top most of the time, and really intense. She dirty talked to me, and I couldn’t help but giggle. She pulls it off though. She then started to scissor me. And then it got really intense, and she climaxed and stopped. I’ve only slept with 3 people (including her), and I was drunk each time. Though it wasn’t the best, I think I enjoyed it so much because it was so personal and passionate.

How sexually satisfying was this hookup? Somewhat

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? After the Hook up we showered (separately), and went to sleep. She woke up later, and we said goodbye and left. Today, I don’t feel weird, but it feels weird that I don’t feel weird. I don’t feel like a lesbian, but I am a little confused because we haven’t discussed it since. She texted me said she left her underwear here and lol’ed, but nothing really after that. I hope this doesn’t destroy her relationship with me as her best friend, because I love her so much but not in that way. I don’t know how to feel, because I don’t know how she feels…

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Intoxication, Just happened, I don’t know why, just went along with it

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

How wanted was this hookup for you at the time? Somewhat

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? No one, I’m never telling anyone.

Did you get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? She is my best friend.

What was the BEST thing about this hookup? It felt intimate, it was a good experience I felt I needed.

What was the WORST thing about this hookup? I feel I may have compromised our friendship

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m not sure, I think it definitely confirmed that I’m mostly heterosexual.

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? I sort of knew it would happen, she generally makes the first move whether I accept it or reject it.

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’ve only had casual sex, and I don’t know if it is right for me. I’ve also only had drunk sex, which I think has damaged my self esteem a bit. I don’t think it’s awful, but it’s not for me even though I continuously do it. I feel that for me anyway, causal sex has altered my previous friendships because I only hook up with friends. I could never hook up with a stranger. I do wish to have sex with someone I love though, because so far it hasn’t felt enjoyable with either sex. I can masterbate and be fine, but sex (I was drunk each time though) hasn’t really gotten me off yet. I feel like there is something wrong with me emotionally…

What do you think about the Casual Sex Project? It’s interesting, and it has allowed me to vent, which I needed.

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