Sex with High School Crush After 15 Years



What’s your gender? Man
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? England
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Publishing
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? None

Sex with High School Crush After 15 Years

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

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? Short, cute, curvy – very long jet black hair. We were really good friends in high school – and I always had the biggest crush on her. She was the type to always be in relationships so never had the chance, or courage, to ask her out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We happened to both be out of long-term relationships. She had come back to our hometown after working abroad – weve always been in touch, so meeting up was a super-normal thing to do as friends.

We had a few drinks and heard a boat party down the road so decided we’d go. Spent a good hour dancing.

I put my hands on her hips in a kind of joking way and she backed up her ass into me. I took her hand and brought her up to the top deck for a drink and a smoke.

She said ‘you know we’re both single right?’ And without thinking I just grabbed her and kissed her. She started getting crazy into it, and the people on the deck started shouting ‘GET A ROOM’ – so we did. I got a cab back to her place.

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 got to her place, went up to her bedroom and started ripping each other’s clothes off.

I swear I thought I was going to cum right then and there, so pushed her onto the bed so I could eat her pussy and calm myself down.

After a while, she pulled me up to kiss her and I just slid myself into her. She was so warm and wet it was amazing.

She said ‘I just want you to fuck me, just fuck me’ so I pounded on her while she dug her fingernails into my ass and wrapped her legs around me.

I was a little drunk, so was harder to cum than I thought, all the time I was sliding myself in and out of her she was biting my ear a little and whispering my name and saying ‘you like that baby, I always knew you wanted this, I always knew you wanted it, just fuck me how you want to, come on baby, come on’

It was so intense my head was spinning like I was high.

We didn’t have condoms, so I pulled out and she grabbed my cock and milked me over her tits.

She was smiling at me as she watched me cum, and all I could think of was ‘Finally, I’ve wanted to know what that felt like SO bad’

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? It was weird. We felt good, but bad about not using protection, so I went with her to get the morning after pill, then got the bus home. We never had sex again, or talked about it – but we’re still very close friends, and see each other often.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Plan B / Emergency contraception

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? I’m married now, and my wife asked if I’d slept with my friend. I didn’t want to lie, so told her what happened. She was okay with it. Makes me very conscious of it when my friend visits though. Told most of my close friends, they were happy as they knew I liked her since high school.

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

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? She’s such a good friend I didn’t want t it to be weird. We’re still very close, so I think it’s okay. I regret risking pregnancy though.

What was the BEST thing about this hookup? Just the release of wanting her since high school and finally feeling what it was like to be inside her. I really liked the feeling of fucking her and cumming all over her tits while she smiled at me and milked my cock over her. Also saw a different side to her. She’s generally cute and girly, but that night she just wanted me to fuck her hard – and was quite forceful. It was cool. I’ll never forget it – gets me hard just thinking about it.

What was the WORST thing about this hookup? Risking pregnancy. Risking our friendship.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. It was just a nice night with a good friend. We’re very different romantically, so would never have worked in a relationship. Im married now anyway.

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

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

Anything else you want to add about this hookup? If you’re in high school and have a crush, do something about it – why wait or be scared of asking anyone out.

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? Reading the site has encouraged me to try to be more sexually adventurous with my wife.

What do you think about the Casual Sex Project? I’m glad I discovered it. Fascinating to read the stories.

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