by Penelope
Gender: Female

Age: 30
Race/ethnicity: White
Location: New Zealand
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Lecturer
Religious affiliation: Buddhist
How religious are you? A little
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

complicated headerSimple or Complicated

How long ago did this hookup happen? Currently happening

How would you best classify this hookup? 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 is a 25-year-old guy friend. We have been acquaintances and party buddies for a couple of years. We talk a lot and have a lot in common. We met at University, and prior to the hook-up, I always admired and thought he was attractive.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I kissed him, drunkenly, after a party. We hooked-up later that night. There wasn’t planning. It was messy, and we didn’t continue to hook up because other friends also fancied him, and he slept with someone else soon thereafter. It continued a couple months later, after it became obvious that we continued to be attracted to each other (despite messy friend stuff). We have been sleeping together now for a month.

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? The sex we have now is pretty full-on. We had talked before getting together, about how we both love sex. I like a lot of sex (compared to other female friends), and so we usually sleep together a couple times a week, and have many sessions on that night. I like going down on him, and he is keen to try lots of positions, and play around. He can cum very quickly (5-10 minutes), but then be keen for more sex 15-20 minutes later. I have cum a couple times during sex, and lots afterwards (playing with each other, etc.). We tried anal last night, but I wasn’t prepared for it, so it wasn’t that good.

The behaviour part is the most difficult for me. I have never had a casual sex relationship before. When it started, it was simple, and fun, and easy. But now it’s different. I think the truth is that I like him. I like having sex with him, and I don’t want him to sleep with other people. But I don’t see us together long term – so its complicated.  He told me last night that he slept with someone else.  I was gutted. Even though we hadn’t had a conversation that outlined whether we were or weren’t sleeping with other people, I am still very upset. We have had so much sex lately, that I can’t imagine having sex with someone else. Who has the time? So I think I am stuck in something complicated now. I am too into the sex and our chemistry to stop – but I know now that I want to be treated with more respect and create boundaries. I am worried that by setting those, or even having that conversation, that it will ruin it. So yes, it is ongoing.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We have always used condoms, aside from last night (twice). I am not on the pill. We discussed previous partners, and I have been tested recently. I will be asking him to get tested, as he slept with someone else.

What were your REASONS for having this hookup? Primarily, fun and pleasure, and attraction. I also think he is a good and respectful person (for the most part), so that I felt that I could trust him to treat me well, and have fun with sex.

Were alcohol or drugs involved? If so, how much? We drink socially a lot. We have had sex several times while drunk, and lots in the morning, when sober.

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? As above, I think things are more complicated for me now. I don’t know how to remain casual – in the sense that I don’t feel I can be in a casual sex thing, where he is sleeping with others. I want the no strings or emotional baggage, but I don’t want to be in a risky situation. I feel mixed about it now, and am wondering if I should stop, or regret that I may have started this up in the first place. He is really into the sex, and I am concerned that I am only sex to him – whereas I enjoy his company and our interactions (even if it’s not meant to be long-term or serious). I like him, but I know that it wouldn’t be a great serious partnership. So I am unsure how it will continue.

To whom did you talk about the hookup? How did they react? I talk to my best mates about it. They are supportive, and happy that I am enjoying it. They are concerned that I might get hurt, and are helpful in talking through how it all works. They give me advice on how to keep it casual and not complicated.

Was this a consensual and/or wanted experience for you? For your partner? Our sex is consensual. He is the dominant partner, and sometimes (like last night) he pushes the boundaries. We didn’t discuss anal sex, and he tried it on last night. I stopped it, but I am concerned this morning that I might be too submissive, and maybe too willing to accept his wants (and not willing to voice mine).

Do you regret this hookup? If so, why? I am worrying now that I may regret it, if it becomes complicated or disrespectful. I am unsure whether I can stop seeing him, because we have a lot of chemistry. He is leaving the country for several months, so it will end anyways, I just worry that I will be hurt when he leaves.

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 is that we are attracted to each other, have similar sex drive, have great sex, and are pretty open about our sexuality and talking about sex.

The worst is that I think I am developing feelings, or needs, that I am worried about talking that through with him.
The hookup has helped me regain some confidence in the bedroom (my previous partner had a low sex drive), but I am struggling with the self-esteem aspects and whether it will become a negative experience.

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

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

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

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