Mr. Hipster

by Monday

What’s your gender? Woman
How old are you? 30
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What country and/or city do you live in? Bangkok
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Writer
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Open-minded and adventurous
How many sexual partners have you had in your life (including oral sex)? 45
How many hookup stories have you here posted before? 0

Mr. Hipster

How long ago did this hookup happen? 5 months ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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? I met J when he and his friends walked past the bar I was hanging out with friends. He smiled and waved at me. I thought that was cute. He also wore nerdy reading glasses which make him even cuter so I decided to give him my number. He asked if I wanted to go have some drinks, but I said no as I didn’t feel like jumping on his bicycle and getting wasted. And to my surprise, the next day he texted me and we set the date for dinner. I also realized that he was 5 years my junior.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a restaurant he knows and talked a lot. I felt very comfortable with him. Maybe it was because he’s talkative and charming, like he knows what to talk about and how to talk to you. At that time I was also considering breaking up with my partner. So, having this ok-looking, charming, younger dude paying me attention really made me feel great. Afterwards, he asked if I wanted to go see a view on his apartment rooftop. I knew what it meant and said yes.

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 were enjoying the view from his rooftop, then looked at each other and like in a movie, we kissed. We went on kissing and grabbing each other until he paused and asked if I wanted to move to his room. Once we were inside his bedroom, we took each other’s clothes off. He pushed me down on the bed and started licking my pussy. I was about to give him a bj when I got a better look of how big his dick was. I was worried it would hurt me. And it did a little when he started to do it doggy style. I thought I practically screamed and asked him to go gently, which he did. But after a while it felt so great. We changed positions a lot and that made the sex even hotter. I don’t really squirt but I did this time.

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? At first it was sweet, we texted, talked, we met twice and had mind-blowing sex. I felt a little bad because maybe I liked him a bit, but didn’t tell him, or the fact that I was seeing someone serious. After 2 months, he bailed me out on a date. That was when I decided I should stop thinking about him. We talked occasionally but never really met. Last thing I heard from him was that he started seeing a new girl, and felt bad about flirting with me and thinking about me naked.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more

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? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

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

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

To whom did you talk about the hookup? How did they react? My friends. They were excited about it, but they knew I’ll forget about him like other guys.

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

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? The sex was really awesome and we got along very well.

What was the BEST thing about this hookup? The sex, the attention, the feeling of being desired and chased after

What was the WORST thing about this hookup? Being bailed out on a date I think

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

Anything else you want to add about this hookup? Sure, we were just fucking and “hanging out”, but I guess bailing out on a date without stating any reason was a little rude. I’m open-minded with sex, but very conservative when it comes to appointments.

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? Casual sex is fun, no strings attached, and satisfactory in some way. But probably that’s all about it. If you learn to deal with the fact that it’s just “casual”, then you don’t get hurt – just enjoy the ride I guess.

What do you think about the Casual Sex Project? Thank you for coming up with this project!

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