Best Friend’s Boyfriend’s Best Friend

by Meg

Age: 22
Race/ethnicity: White
Location: Orlando
Highest education received: Some college (not currently in college)
Occupation: Hospitality
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

Best Friend’s Boyfriend’s Best Friend

How long ago did this hookup happen? About a year ago

How would you best classify this hookup? Fuck-buddy that turned into friends-with-benefits

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? He was my best friend’s boyfriend’s best friend. He was cute. A bit on the short side. I didn’t know him before that night. He was invited over to the apartment I shared with my best friend. My friend, her boyfriend, and I were just hanging out when my friend had joked about how I hadn’t “gotten any in a while.” My friend’s boyfriend said his friend hadn’t either.

So a little while later the friend shows up. Before the hookup I was definitely interested.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We all just hung out downstairs for a while. Drinking and having a good time. About an hour in my friend and her boyfriend announced they were going to bed. We were left downstairs alone. We continued drinking and talking. As the night progressed we went to my room, I don’t remember why. We both knew what would eventually happen, thanks to the openness of my friend. We started looking for a movie to watch. When he saw I had his favorite movie he said “I’m going to kiss you now”  and he did.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? From there we forgot about the movie and started making out on my bed. It accelerated pretty quickly. He  started fingering me then wanted me to give him a blow job and I happily did so. He seemed to be really into that, complimenting me the whole time. From there he went down on me and I orgasmed. Them we had sex and he orgasmed. After he finished we cuddled naked and talked for hours. We were really comfortable at that point.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom. Yes, very briefly.

What were your REASONS for having this hookup? Like my friend had said we hadn’t had sex in a while haha. We were both attracted to each other. I guess that’s all the reasons we needed.

Were alcohol or drugs involved? If so, how much? Alcohol was involved. Enough that we were a little less inhibited, but not enough to be drunk.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We hooked up throughout the next few months. We became pretty good friends. We could talk to each other about anything. He got a girlfriend so we stopped hooking up. Now that they are over, who know what will happen? I wouldn’t mind seeing him again, but also won’t be disappointed if we don’t. I have thought about him occasionally and wish him well.

To whom did you talk about the hookup? How did they react? Obviously we talked about it with both his best friend and mine. His friend didn’t seem to care what we were doing. My friend was totally on board at first. However, after a few months started asking why we weren’t together. She dropped it after a while.

Was this a consensual and/or wanted experience for you? For your partner? It was definitely consensual and wanted by both.

Do you regret this hookup? If so, why? I don’t regret it at all. We had fun and became friends.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this was having someone I could go to whether I was to talk or have sex. he was there. It didn’t change the way I think about casual sex. I have always been pretty open to new things. It wasn’t my first casual sex experience and I probably won’t be my last. It did give me a pretty great confidence boost haha.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? Casual sex isn’t something everyone sees as good. I think you should do what makes you happy. However doing it safely, is a must!

What did you think about this story? Tell us in the comments!

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