by Shy Guy
What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Media/Entertainment
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
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? 0
Sex with High School Crush – 15 years later
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? She was short, curvaceous – very pretty face, deep brown eyes and really long jet black hair. Very pretty in an unconventional kind of way, not classically attractive as such, but sexy as hell in an exotic sort of way.
I always had a big crush on her ever since high school. I would class her as one of my best friends – we’ve known each other since we were 14, meet up for a drink regularly. We’ve always been nothing but very good friends and confidants – and though I lusted after her all through school, our relationship has been nothing but platonic. She’s one of my most treasured friends.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had been traveling for a while and had come back to our hometown for a while. We arranged to meet up as we always had done so many times before. We met in a pub in the old quarter of the town, had quite a few beers and caught up on news. I’d recently broken up with my girlfriend, she’s broken up with her boyfriend. For the first time ever we were both single at the same time.
After a few drinks, we heard there was a boat party down at the dockyard and decided to go check it out together. When we got there we hit the bar – and switched up to drinking dark rum and then hit the dance floor. We’d NEVER been dancing together before.
We had both had a fair bit to drink – the music was awesome and I jokingly put my hands on her hips and pulled her close to me, and she pushed her sweet ass up against me, which made me instantly hard.
She took my hand to lead me off the dancefloor and we hit the top deck to grab another rum and a smoke.
When we got up into the fresh air, she held my hand, took a drag off her cigarette and said – “you know, we’re both single…”
And with that, I just leaned in and kissed her, held her close at the small of her back and then she eagerly reciprocated. At that point, we couldn’t keep our hands off each other and we really started going for it.
People up on the top deck started saying ‘get a room’ and stuff, so we did. Called a cab and went back to her house.
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 back to hers went straight upstairs and just started pulling each other’s clothes off. We were kind of intoxicated – not just from rum (though we had drunk a lot) but just off the excitement of what was happening. I guess you could say there was a lot of pent-up attraction there, after 15 years of never getting it together.
After I got her naked – which was such a weird thing to see, glorious, but kinda strange, we fell back onto the bed together and I worked down her body and thighs in little kisses and then took a good long taste of her pussy, which was already slick and wet.
I went down on her for a while before she pulled me back up to her and she just whispered, please, “just fuck me, I want to see your face when you get inside me – this is for you okay, just fuck me how you want okay baby”. So I kissed her long and deep and, and she pushed my chest away and said “I want to see your face when you fuck me” and so I stared into her eyes and slid my dick inside her effortlessly and as deep as I could.
Oh man, I can’t describe just how awesome it felt, she was a so wet and so hot inside – the walls of her pussy so tight around my dick, it was amazing. I hoped that the rum was going to numb me enough that I could fuck her for a while, but the fact was, I’d dreamed about this since I was a teenager, and the feeling was overwhelming. I fucked her missionary for a little while and sucked on her sweet little tits, and asked if she was on the pill. She just smiled and said “it’s okay baby just pull out when you’re ready… I know you’ve wanted this, just enjoy it, okay babe. I want you to enjoy it.”
It was too much for me at that point so I pulled out and she reached down and milked every last drop of cum out of my dick, staring into my eyes and smiling while she did it, like she was loving every splash of cum on her body. With every spasm of my cock, she just looked into my eyes saying gently “there you go baby, there you go…”
My orgasm was so intense it was unreal – like 15 years of build-up had been released.
We collapsed back onto the bed together, and I just lay there quietly in awe and she said “I’m so glad I could watch you cum – I’m so glad I got to see how happy you were when you went inside me” and then she just rested her head on my chest and we fell asleep.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, one
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 morning we were kinda sheepish together. As we were so drunk the night before and didn’t use any birth control, we decided she should go get the morning after pill – so had to travel to the surgery and wait together. It was a bit odd, but kind of okay – we were just smiling at each other and shaking our heads at how irresponsible we were. I felt a bit guilty about it as she was the one who was going to have to take it and I knew that birth control meds sometimes had a bad effect on her. She was cool though.
I also felt a bit bad that I hadn’t given a good account of myself, as it were and came so quickly. I would have liked to have made sure she had an orgasm, though I guess at the time she was just really eager to please me, which she absolutely did. I made a joke about it, and she assured me it was fine and she’d had a nice night.
I still feel very close to her, we never hooked up again, but I see her very regularly – pretty much once a month if she’s not traveling. Every time we meet it’s just as fine as it ever was. We bring up that night sometimes and smile. It will never happen again though as I am now married with kids – but I do sometimes think about that night and just the overwhelming intensity of how amazing it was to finally be inside her.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, 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
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 told my close guy-friends. They were totally made up for me – some of them also knew her from school, and knew how much I liked her back then, so they were all like – “mate, finally – only 15 years late!”
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? I don’t regret it as such – I LOVED it, but it could so easily have affected our relationship. Thankfully it didn’t at all – if anything it made our relationship stronger. I also regret not making her cum and looking after her pleasure, as I wanted her to enjoy it with the same intensity as I did.
What was the BEST thing about this hookup? Staring into the eyes of a girl I’d fantasized about fucking for like 15 years and the sheer release of emptying my balls on her sweet body in an earth-shuddering climax.
What was the WORST thing about this hookup? Going to get the morning after pill. That I came and she didn’t.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It hasn’t changed how I feel about casual sex really.
All things considered, how POSITIVE was this experience? Fairly 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? Generally, I’ve found casual sex has been great for my confidence at times when I may have been lacking in it.
What do you think about the Casual Sex Project? Great site – I love reading the mix of stories.
You have a hookup story to share? Submit it here!