My Best Friend’s Girl

by Mokinado

Gender: Male
Age: 28
Race/ethnicity: Caucasian
Current location: Europe
Highest education received: Not graduated from high-school
Occupation: Self-employed
Relationship status: Single
Religious affiliation: Spaghetti monster
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

My Best Friend’s Girl

How long ago did this hookup happen? About 2 months

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? She was the fiancé of my former best friend. We had grown apart for a while now, but remained still in close contact. She entered his life about two years ago, coming from a nasty divorce. They were a very comfortable couple in their daily lives, yet had a lot of unresolved issues, which usually surfaced whenever alcohol was involved.

I always thought of her as a friend and actually somewhat enjoyed the underlying sexual tension we had, without acting on it. We started speaking more and more often, at times leaving my mate completely out of the conversation. I occasionally hung out with her for a brief coffee and a nice substantial chat, nothing more.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One night my friend was somewhere out partying, so jokingly I asked (it might have been her also) if I should drop by. I bought a bottle of wine and she had some as well. We even had to get a refill, so alcohol was definitely a factor. We spoke for hours and somehow ended up on the couch together. With my judgement impaired I made a move on her and she reciprocated.

After making out for a while we realised what a pandoras box we had opened. We made a quick decision to head out (before her boyfriend got back) and get some fresh air to cool down. We went to a bar, but it was hard to keep hands off each other. We decided to get a cab home and I apparently asked her to come to my place. Thankfully she was conscious enough to think it was a bad plan. I was so glad to wake up alone the next morning.

I did, however, not have such good luck about a week later, when she had a party at their place. My mate was at work, so she was with two of her former colleagues (a dude and a girl, whom I did not know). I could see why she wanted some company.

As the night progressed and the table games weren’t cutting it, we decided to move out. We had a few drinks at a bar and it was already pretty apparent some coupling was happening, especially with her arm neatly tucked around mine. As we exuberantly consumed even more liquor, the party slowly started to unwind. When it was time to head home, we got a cab, but this time we were heading to my place.

I remember briefly asking her, if she is absolutely sure about that, and she consented.

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? As soon as we got to my place, I pushed her on my bed and started making out with her. Without a lot of thought process I then moved her to the side of the bed and practically ripped her stockings off. She was very well maintained. I wasn’t using any protection and didn’t engage in any discussion about it either. My mind is quite foggy on the details, but there was definitely some cowgirl action involved.

I had to wake up early the next morning, so after a brief nap we gave it another go, before getting a cab downtown. I dropped her off and went to get some business done, hungover as hell, trying not to overthink what just had happened.

Did you have an orgasm? Did your partner(s)? I had, but I strongly doubt she did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Foolishly, none.

What were your REASONS for having this hookup? Poor judgment. Gallons of hard liquor. She was in an unhappy relationship, I was single and impulsive. Curiosity?

Were alcohol or drugs involved? If so, how much? About two bottles of wine, a bottle of rum, at least two or three glasses of kriek lambic and… another bottle of wine, to finish off the night. We were pretty serious about the whole drinking thing.

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’ve been talking less and less since we wanted to keep some distance.

We met up maybe about a week later, briefly discussing what had happened and decided to keep it a secret. Her boyfriend has quite a temper when he’s jealous and a lot more than just my reputation and social circle was at stake here.

I also had a bit of a falling-out with my friend for unrelated reasons, so contact has been very infrequent and brief.

To whom did you talk about the hookup? How did they react? None. No-one. Not until now.

Was this a consensual and/or wanted experience for you? For your partner? Apparently, yes.

Do you regret this hookup? If so, why? You should never fuck your best friend’s girlfriend, whatever the justification is. So, yes. Keeping him in the dark about it is the worst part, but I know him well enough to know fessing up is not an option.

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? I suppose it revealed a whole new level in my promiscuity. I will try to be somewhat more careful around OPP (Other Peoples Pussy) from now on. But it didn’t exactly curb my sexual behavior.

All things considered, how POSITIVE was this experience? A little positive

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

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