End of a Friendship

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What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation?
What’s your current relationship status? Engaged/Married (monogamous)
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)? 28
How many hookup stories have you here posted before? 0

End of a friendship

How long ago did this hookup happen? 4 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 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? My partner was Helene, who had been my friend for 2-3 years at that point. She was my age, 28 at the time. She’s a tall blonde, thin with small breasts but a nice derriere for a girl that skinny. Easy smile and a friendly demeanor. A pixie type, if not for her height.
I met her through college buddies, and we ended up belonging to the same tight-knit group of friends. With time, we found that we shared many interests and started hanging out more and more, to the point where she was clearly my best female friend.
At first I had pretty much accepted that we were way inside the ‘friend zone’. I initially thought she was cute but ended up treating her pretty much like a friend. Then… long story short I somehow got it inside my head that she may have other ideas. I won’t get in the post mortem of whether I was right or not here… But she acted/talked more and more often in a way that went beyond mere friendship – writing how she missed me, and did not enjoy herself when I wasn’t around, being quite tactile, etc. This could seem quite mundane, but I’m not an extrovert guy, in speech or in actions. So doing all that I felt she took that thing up a notch compared to the way we acted before towards each other.
So…when she offered for us to go on vacation in Asia together, I started really feeling something was going on. When came time to book hotels, sure enough we booked one room… and one bed.
The first few days of the trip were normal, no awkwardness in the evenings. Just a kiss goodnight on the cheek. I was sleeping in my boxers but taking the clothes off as discreetly as possible before. She slept in a long t-shirt and short shorts. We basically collapsed every night after a big touristic day.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One evening we went out later than usual. Had some wine but nothing extreme either. Then we came back to the hotel room with some take out food and watched a TV show.
After that we went to bed as usual. Foolishly – as time would tell – I kept thinking that night about Helene’s attitude towards me in the past weeks/months, her idea for the trip, etc… and the fact I genuinely liked her…and desired her. I “accidentally” rolled on her side of the bed, getting closer. I startled when I realized – from her breathing – that this had woken her up…
But she didn’t move at first. After what seemed like ages to me but was probably 20 seconds, she started shuffling a bit, probably still maintaining “plausible deniability” that she was asleep the whole time… until her ass went bumping on my crotch… Now the key point is that by then, I was rocking a massive, bulging erection. So all of a sudden, through our respective underwear, my penis was firmly held in between my friend’s butt cheeks… I couldn’t believe 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? There was no sense to keep pretending… Now that I was basically spooning her I started caressing her arm and kissing her in the neck, and from there started touching her breast.
After a minute of that, I admit I felt awkward, not sure where to take it next. That’s when she took the initiative, suddenly rolling to end up on top of me, kissing me, then taking off her t-shirt. I couldn’t see her breasts (this is one of the rare times I’ve had sex fully in the dark), but touching these small, firm boobies was a delight. Her nipples were perky and delicious tasting.
She then gave more attention to my parts, taking off my boxer, and immediately starting to give me oral sex. I wasn’t surprised, because she often had joked about her love for sucking, even admitting to some dreams about it. Seeing my friend’s eyes looking at me while my dick was deep in her mouth, her tongue lustfully and skillfully running around it, was something I didn’t expect from that trip…
I was really afraid to come by then, and switched my attention to her butt, caressing and massaging it. She stood up to remove her thong. I love oral too so I immediately lay her down on the bed again and started licking away. She was more than receptive and responded enthusiastically. I stimulated her G-point for a while after that, which made her come. When I finally put my penis inside her it almost slipped out like a soap, it was so wet… I was so excited that I didn’t last despite my best efforts.
We re-grouped for a few minutes but it wasn’t hard getting ready again. This time I rolled her around to take her doggy style, and she came again, copiously.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? We collapsed in bed after that first night, and really only talked in the morning. We only talked about the sex though, and sort of shied away from the whole conversation about what it meant… I thought the implicit feeling was “what happens in Vegas”… Myself I liked her a lot, and was definitely thinking about a relationship, but didn’t want her to feel pressured, as I knew she’d had a string of difficult ones recently.
We had sex every night for a week after that, and the vibe was definitely “crazy young people on vacation” rather than “start of a relationship”, including a threesome (more on that in another entry).
After the end of the trip however she suddenly became very distant. After a few weeks it was clear she did not want to see me anymore. What was frustrating was the lack of communication. I never quite knew if she was angry that I had initiated the hookup, ruining our friendship in her view, or if she did have a crush on me but concluded I wasn’t ‘boyfriend material’ in the end.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Friends.

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

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Very much

Why do you regret this hookup? It led to the end of a friendship. Even if it took time to appear clearly, this is the only reason I can think of.

What was the BEST thing about this hookup? Lots of sexual pleasure. My partner was a great match for me in my view, physically and otherwise.

What was the WORST thing about this hookup? It caused a snowball effect of emotions that led to the end of a long friendship.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes – never do it with friends, unless things are crystal clear from the very start.

I already had in the past and it hadn’t ended the friendship at all. But after this one I realised that it’s not worth it. A friend might be for life, but you can hook up with anyone. If you think you might want a relationship with a friend, just talk to her about it. You can’t start with sex and then “see what happens”.

I realise all that seems obvious when seen from a distance, but in situation it’s very different so my advice would for everyone to keep that in mind like a mantra…

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

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

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