Guilty Pleasure

by Helena

What’s your gender? Woman
How old are you? 19
What’s your race/ethnicity? Chinese
What continent do you live on? Asia
What country and/or city do you live in? Singapore
Highest education received: Some college (currently in college)
What’s your occupation? Student
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Bratty switch
How many sexual partners have you had in your life (including oral sex)? 22 oops
How many hookup stories have you here posted before? 0

Guilty Pleasure

How long ago did this hookup happen? late last year

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? He was kinda tall, clear face and a lovely sharp jawline. I would say his main style inspiration would be Brendon Urie and he had a music taste to match. I met him through a church thing on our college and we became friends naturally, being the noisy ones in our group. I’ve always thought he was attractive and charming though I’ve always had my doubts about his morals due to the company he keeps in school. Either way, I did like him at first but figured we would never work out as a couple.

We became close when he found out that I wasn’t exactly as obedient as the other kids in the church group we were in, and started going clubbing together once I became legal. That’s when the sexual tension kicked up a notch after a particularly close encounter in the club but we brushed it off as a one-time thing. pshht. so much for that.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a combination of instances that culminated to the actual thing. Furtive glances in our drinking circle. Physical support on drunken nights. Grinding on the dance floor. Hell, even sleeping in the same bed (with a pillow in-between because there was someone doing work literally beside the bed)! All these things led up to us cuddling in my bed after coming back from the club. We had been feeling each other up right beneath the noses of our dear mutual friend, who was absolutely oblivious to the tension we had.

He looked at me as I lay on his chest, not once, but three times before he went for 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? He climbed on top of me and we started making out heavily from all the tension and sneaking around we’ve been doing. It felt wrong but so right at the time, I was honestly a little giddy looking up at him when we took a breath, his face flustered and lips red, just barely outlined with the soft table light I had. He was hot and heavy and damn was I turned by the little man-grunts he made as he traveled from my lips to my neck. He was obviously more skilled than I was at the time.

The next series of events was rather blurry but I remember our clothes coming off and I was squirming as his fingers worked on me roughly. I remember being in different positions as I teased him, especially the one where I rode him with my disheveled hair illuminated by the soft light, watching the streetlights go up and down with my movements. Pretty sure along the way, I came on his fingers and then sucked him off in return. I’d say it was a pretty good bj. and that his fingers were one of the best among the 22.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 actually had a feedback session thing on text a few days after. I kinda always did that with the partners I liked to break the ice, but with him, it was different. We both knew it was wrong, and though we had some pretty whack feedback thing, we agreed it was a one-time thing and we didn’t talk for more than a month after it happened.

Until it did happen again. Different scenario but yes again and with anal. Lots of anal.

And then we didn’t talk at all until a month or so later. Not the classiest but not the worst, but at the same time it feels the worst of all the 22 guys I’ve had. Honestly, I don’t regret it because I enjoyed it immensely, but our friendship hasn’t been the same since. We used to be close and talk about girls and shitty exes when we meet but now, it’s different. He was different from all the FWBs and hookups and whatnot I’ve had because of our close friendship and the feelings involved. Sure, it was a good fuckin time but tbh, it was never going to pan out well. I just hope he’s doing well and that he finds the girl for him (though I do think he does have some double standards with that but hey, things happen). I’d invite him to my wedding and hopefully we’ll laugh about it in the future but ya know, things will never be the same.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Intoxication, I was feeling lonely, I didn’t want it but was unable to stop it

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? I don’t know

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? I eventually told our mutual friend after they stopped being close. He was disappointed but not surprised.

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

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

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? A little bit

Why do you regret this hookup? Because we met at a church thing. The irony of it has always been our inside joke but there always was a twinge of guilty pleasure in there.

What was the BEST thing about this hookup? He was fucking good. Definitely was more experienced than I was at that time. He was my 8th but by far one of the best.

What was the WORST thing about this hookup? Went from close friends to “confidant but not a friend” real quick

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Made me feel pretty shitty, but also a bit of guilty pleasure because I managed to satiate the tension and curiosity I had towards him. But I’ve learned that sex is not a way to someone’s heart and is a surefire way of changing a friendship, mostly in a bad way.

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

All things considered, how NEGATIVE was this experience? A little negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Tbh I think it should be treated with more respect. The difference between FWBs and a beloved partner is phenomenal and consensual, exclusive relationships should be glorified more, or at least not be put down. Sex is a beautiful and wonderful thing and should only be shared with people who treat it as such.

What do you think about the Casual Sex Project? kool

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