by Jess


Gender: Female
Age: 18
Race/ethnicity: Caucasian
Current location: Ontario, Canada
Highest education received: High school diploma
Relationship status: Dating
Religious affiliation: New Methodist
How religious are you? A little
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bisexual but prefers men
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? None

Boyfriend’s Best Friend

How long ago did this hookup happen? A few years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling

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 tall with long curly brown hair and he had the best smile. From the first day we met we had a very strong chemistry. We were friends for a long time and I was dating his best friend. I didn’t learn until later that he had fallen for me hard until months later, when we stayed up late talking on Skype one night. After that night I realised I had feelings growing for him as well. We were both finishing high school, and slowly I felt like maybe we could take it to the next level.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The first time we did it was at his apartment. He had invited me over for a hang out and as we watched t.v. and talked he kissed me. He pulled away and apologised and I said not to and kissed him back. We became very touchy-feely after that and then had sex.

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 moved from making out on his couch to undressing in his bedroom. He undressed me and kissed me all over and then I undressed him and saw how well endowed he was for the first time. I got extremely excited after that. He laid me down on my back on the bed and we started making out. He asked me if it was ok if he penetrated me and as an answer I thrust him into me myself. It had a snowball effect after that and we had sex for at least two hours in multiple positions before he blew a very large load very deep into my vagina. I found that extremely kinky and wanted to do it again another time. He realised what he did afterwards and asked if I was ok with it. I said yes, he gave me the best thing he ever could, and we made out again. After half a dozen more times, and never any condoms, I found out two months after the last time that I was pregnant.

Did you have an orgasm? Did your partner(s)? I had many orgasms. He did too.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We took no precautions to prevent pregnancy, and we both had not had many sexual partners before hand so I trusted he did not have any STI’s. I don’t have any so I’m glad he was clean.

What were your REASONS for having this hookup? I was bored in my relationship but I didn’t want to break it up. My boyfriend wasn’t much into sex but his friend was. And after he had told me he had very deep feelings for me, I thought I’d give him a try. It was worth it.

Were alcohol or drugs involved? If so, how much? We were both sober for all of the times we had sex.

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? I became pregnant but ended up losing the baby in my first trimester. While I was pregnant I told my boyfriend what happened and he was sad I had done it but was glad I at least told him. After I lost the baby we were all devastated but it was probably for the better since I was so young. He and I don’t talk any more and I am now engaged to be married with the same boyfriend I had back then. I have no hope to be able to contact him as he has told me off and doesn’t want to see me any more.

To whom did you talk about the hookup? How did they react? I told only my boyfriend. He was upset at the beginning but forgave and supported me in the end.

Was this a consensual and/or wanted experience for you? For your partner? All of it was consensual for me except for the last time. He consented to all of them.

Do you regret this hookup? If so, why? I do not regret this hookup although I do regret some of the consequences that came afterwards.

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 hookup was that it was the best sex I have ever had. The worst was that the last time, he had raped me and left me depressed. I still like casual sex, although I’m extremely careful how I do it now.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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