Fantasy Come True with my High School Crush

by Steven

What’s your gender? Man
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Fantasy Come True with my High School Crush

How long ago did this hookup happen? 5 months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Friends-with-benefits

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? Knew her about 18 years ago up until college, the lost track of her… had a killer crush on her back then, but was always scared to pursue her because I had her in such a pedestal. She always dated really high-quality guys,  so I figured I’d never had a chance. She has big brown eyes, a dark complexion, long kick-ass black hair, and a killer body…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I ran into her late last summer, she looked amazing… more amazing than when we were kids. I played it cool, she’s also married, so it just nice to see her. We caught up for a beer a few times just catching up about old friends. We went to a ball game once with an office group and I totally caught her looking at me… I was in heaven. I couldn’t resist pursuing it; I wasn’t even looking to mess around but I was so sure I wanted this… she was a little embarrassed I caught her, but I told her I’m always checking her out. We held out and stayed cool. About two months later, by chance, we ended up on a work trip together for a conference in Minneapolis and just about everyone who’d planned to go had bailed from the trip. We didn’t stand a chance of getting through this. We talked about it ahead of time, decided we were going to be good and just stay close friends, but we started hooking up within an hour of arriving that Sunday. We started making out, and we both hoped that the other would be a bad kisser, but we couldn’t stop making out. We made it to like three of the 30 or so sessions of the conference the whole week, and the rest we spent together. We went out all over the place together and had tons of fun. It was six nights of non-stop amazing sex which got better every time.

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? Making out that first time was amazing we tried to keep it there, it was so good. We were escalating, impulsively she pulled down her right shoulder strap on the tank she was wearing, and I dove on her nipple, it was sooo sweet. Her gasps were incredible. I pulled off her other shoulder strap, her tank fell to the floor, and I began kissing her tummy. I eased her pants down from the back as I was caressing down, firmly holding her with my hands. I kept kissing her tummy, licking as I went down. I walked her back to the bed and had her lay back. I propped one of her legs over my shoulder and went down on her. I loved it, and she was loving it too. There was a pounding thunderstorm outside, pouring rain, flashes of lightning every few minutes, and the power was flickering, it was perfect. I was gaging what she liked, licking her clit, easing in and out, fluttering my tongue, working so hard to be good for her. She was escalating and warming up so well. I eased my pants down while I was down on her without her knowing.

After a while, I eased back up to her tummy, took a swig of water and kept kissing her everywhere. Coming back up to her nipples, massaging them between my tongue and teeth, gaging her every feeling, she was loving it. I was so loving feeling her escalate like that. I eased back up to her neck, and she escalated really well when she felt my bare legs between her thighs, knowing I stripped my pants off. As my tip touched her, we looked at each other for a second. This first touch was sooo sexy. I could feel she was so wet and it felt so incredible against me. I started easing in, and we began making out again. I was pushing gently until I was all the way in and we were in an amazing, perfect rhythm, pushing so hard, escalating together.

She would take me right to the edge, then relax, then work me up to the edge again, and relax, each time making it more and more erotic. When she finally worked me up about the 5th or 6th time, we came so hard together. We had sex three more times that night, and at least five or six times each of the following days and nights during the ‘conference’.

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? We are still great friends, there is zero drama about it, only the two of us know. We get together about once a month and have incredible sex.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), It was easy/convenient, I didn’t want it but was unable to stop it

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? A little bit

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

How wanted was this hookup for your partner at the time? Not at all

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? Nobody except for her. She loves that we hook up and we’re constantly thinking of ways to make it better. She loves that I ask her what I can do. We tell each other it’s the best sex we’ve ever had.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? My wildest fantasies about this girl from when I was a kid, through the years I lost contact with her… didn’t come close to how good it has been. Now my fantasies are about the last time we had sex and what I’m going to try with her next time we’re together.

What was the WORST thing about this hookup? Nothing… I feel no guilt, I’m so sexually fulfilled, it’s beyond amazing…

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I would not have casual sex with just anyone, in fact, I don’t think I could be enticed by anyone else at all. I’ve had plenty of other opportunities and never once done this or come close.

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

All things considered, how NEGATIVE was this experience? Not at all 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? It’s made my life better. I’ve not been judged by others since I keep it private, but others’ judgment is beyond insane – people ought to reserve judgment far more than they do.

What do you think about the Casual Sex Project? Very cool!!

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