Sex With My Best Friend



What’s your gender? Woman
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: High school diploma
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)? 6
How many hookup stories have you here posted before? 0

Sex With My Best Friend

How long ago did this hookup happen? A week ago

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? Most of my partners have been ex-boyfriends, all different ethnicities, knew them as friends before and met at our school, and felt comfortable with them before anything sexual happened. Only this one partner was a hookup and it was with a friend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We planned it the night before it happened. We both admitted to being sexually attracted to each other and that we had been thinking about hooking up for a while. He had just gotten out of a relationship and I was single so we thought “Why not go through with 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? We hooked up at his house. At first it was awkward but eventually, we became very comfortable with each other. We got undressed and went down on each other and that eventually led to penetration. Nothing very kinky happened but it lasted for a long time. It was very comfortable and we were able to laugh and feel normal together free of judgment. It was overall a good experience and helped him to accept what had happened between him and his ex, and I was able to feel a connection with a friend who I love as well as accept something that had happened in my life. We talked about it before and after, talking about what we were comfortable with. After we agreed that it should be a one time thing and that it was an extremely spiritual and healing experience for the both of us.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? He admitted to realizing how much he missed his ex (they had a very long-term relationship 3ish years) and that he is scared to move on. He also said that this was a necessary step to him accepting that it was over and made it much easier for him to handle the situation. Today I asked him if he would ever want to do it again, I had a very good experience sexually speaking and I was hoping he’d be interested… even though I knew that right now is not the time and that he needs time to move on from the breakup and be okay with being alone, and that was exactly what he told me. Although he did say that after some time has passed he would maybe want to again. We both don’t want this to be a regular thing because that’s not what we want from each other. It’s kind of funny because initially this happened to remove sexual tension but I will admit it has not gone away. For the future, I hope that we remain best friends and whatever happens will happen. I just hope that it won’t poorly affect our relationship. I feel just as close to him but I almost wish that it had been a sexually unsatisfactory experience so that this questionable “friends with benefits” door wasn’t opened.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Boredom, It was easy / convenient

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? Somewhat

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? One of my friends and he was happy for me and glad that I had a good experience.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? A little bit

Do you regret this hookup? A little bit

Why do you regret this hookup? I regret it because now I would like to do it again and I wish I didn’t. I appreciate our relationship deeply and I don’t want to risk ruining it.

What was the BEST thing about this hookup? Being able to help each other emotionally.

What was the WORST thing about this hookup? Knowing that this breakup will be very hard on him and that this was a strange step to his healing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

All things considered, how NEGATIVE was this experience? Not at all 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? I think we have come a long way in how we view casual sex and it is more widely excepted, which is amazing.

What do you think about the Casual Sex Project? Can be a very helpful platform for people to not feel guilty about their sexual experiences.

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