Hooking up with My High School Crush Six at Age 24

by Lily

What’s your gender? Woman
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Los Angeles, CA
Highest education received: Some college (not currently in college)
What’s your occupation? Web Designer
What’s your current relationship status? Single
Religious affiliation: Agnostic
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)? 25-35
How many hookup stories have you here posted before? This is my first one.

Hooking up with my high school crush six at age 24

How long ago did this hookup happen? Last week

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For more than 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 a friend I’d known since high school. He had dated a friend of mine, and our group of friends hung out quite a bit. I thought him a total babe, as did everyone else I knew. He was very surfer-boy ‘dreamy’ – icy-blue eyes, tan skin, all abs. *sigh*

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I hadn’t seen him in seven years, but I moved back home recently and ended up running into a mutual friend of ours at a bar and then later hanging out with him with our mutual friend. We ended up going to the beach, and later he messaged me on Facebook asking to hang out, saying he needed someone to talk to. We met up and ended up in my car in a parking lot ‘talking about life.’ He leaned over and kissed me. I was very surprised, as we had always had this playfully-making-fun-of-each-other relationship, and I didn’t think he was attracted to me, nor would I have ever let on that I was attracted to him.

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? During the hookup, we made out in the back of my car. He has a really strong physique, and he kept pulling me towards him, which I found very attractive. He put his hands up my dress and I went down on him. It was all very passionate, as I was deeply attracted to him as well as pleasantly confused about the sudden change in the status of our relationship as ‘friends.’ It was a really nice blur, his hands on my legs, our bodies cramped in the back of my car, sweating in the summer heat…

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? No

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? The next day I felt happily confused, and I thought about him. I wasn’t quite sure what it had all meant. I knew we were very incompatible relationship-wise, so I knew it wasn’t going to lead anywhere, but it was nice for what it was. It changed my perception on all the times we had spent ‘making fun of each other’ realizing that we had been flirting, even though I hadn’t seen it that way. He did say, “I always thought you were adorable,” which came as a complete surprise to me. Although it was just a hook-up, I do believe it led to a deeper level of friendship between us.

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), Learning new things, experimenting, I was feeling lonely

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? I talked to my best friend. She was very surprised but was ‘proud’ of me, because of my partner’s reputation as an ultra-babe. She said something along the lines of, “I’ve been trying to get at him for years!! You’re so lucky…” This made me feel very desirable.

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

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

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The rush of excitement that occurs when someone you think is strictly ‘a friend’ but secretly find very attractive pulls the moves on you, changing the relationship. Also, his body, his hands on my hips, his mouth… just being close to him in all his attractiveness. Him wanting me. Him wanting me badly. Me wanting him badly.

What was the WORST thing about this hookup? Nothing!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s made me feel more attractive and desirable. It’s made me feel more affectionate and sexual. Yeah, I think it has changed me. It made me feel like more.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? It was fun, and I’m glad it happened. It’s interesting to have a friend for so long, and then after so many years to learn that all the attraction and sexual tension I felt for the person was returned. It was just purely fun. Intense. Passionate. A summer fling.

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? I think casual sex with the right motivation is a wonderful thing. In this particular hook up, my motivation was to be close to this person physically and to have fun with them. I knew it wasn’t more than that, and so did they. But we cared about each other and had a great time and were intimate and respectful without being ‘in love’ or ‘in a relationship.’ The hookup strengthened our relationship as friends and was also very physically satisfying.

What do you think about the Casual Sex Project? I love it!

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