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What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
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)? 50+
How many hookup stories have you here posted before? Many

Middle School Crush at University

How long ago did this hookup happen? 12 or 13 years ago

What was your relationship status at the time? Dating casually

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? I hadn’t seen K since I was in the 8th grade because, that year, I moved one county over to live with my dad (parents were divorced). When we were in middle school, Kwas the “popular” girl with all of the friends and I was a bit of an introverted nerd. I was absolutely certain she had no idea who I was.

Now, at the time of this story, I was at a house party during my sophomore year away at University when I randomly saw K across someone’s back yard. She was about 5’7″ and what I’d like to call “a little stocky.” She probably weighed around 140 lbs, which in my ultra-critical mind was too overweight. You may have thought she was of average weight. She had shoulder-length brown hair, still had a cute face, but had definitely lost a few points in my mind because of the freshman fifteen. Her breasts were average and her butt was nothing to write home about.

I happened to be at this party with a girl I was dating (and three of our friends – one of whom I was also fucking on the side). But more importantly, I didn’t think K would recognize me, let alone remember me, so I just pretended that I didn’t know her and went about the party as if we were strangers. It turned out that the very moment K saw me, she came over to me and began talking about how she remembered me, how we went to school together, etc. etc. We strolled down memory lane a little bit, but we never exchanged phone numbers or anything. We just thought it was funny how after all these years we ran into each other so many miles away from home.

The girl I was dating wasn’t the jealous type, but she let me know that she thought K was definitely into me. It was her comment that made me think how maybe I should have gotten her number. Even though I didn’t find her to be much more than a 6 out of 10, I thought it’d be nice to be able to say I fucked my middle-school crush nearly a decade later.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The following year, my junior year, I lived in an apartment which was down the road from a bar which served free beer every Thursday night. Every week I’d meet a few friends and we would drink until we were obliterated. I’d always do my best to convince a girl to walk home with me, but often enough went walked home alone.

On one particular night, K was at the same bar. Our eyes met, we said hello to each other, but I sort of avoided her. I wanted to bring home something better than a 6, so I just kept her in the back of my mind in case I came up empty toward closing time.

Sure enough, closing time came, and I was still stag. I looked for K, couldn’t find her, assumed she left, and told my friends goodbye before starting to walk home. After crossing the street, there’s suddenly a girl to my left, giggling and laughing and stumbling around. It’s K. She’s hammered. She starts following me, asking me where I’m going, and I play coy telling her that I’m going home. “You wanna walk with me for a while?” She laughs and follows along.

The entire duration of the walk back to my apartment, Karen was obnoxious. She kept accusing me of being gay because one of the four people she had seen me at the party with “way back when” was a gay guy. In reality, he was the roommate of the girl I was dating (and happened to be the most amazing wing-man ever in regard to introducing me to girls). Anyway, Karen was annoying me with her gay accusations, so rather than treat her like a decent human being who I’d have sex with and move on from, I decided I was going to treat her like a fuck toy.

Also during the walk home, the girl I was dating gave me a call to make sure I was getting home alright. It would have been impossible to convince Karen to be quiet (she was way too drunk), so I instead just kept telling my significant other how she was “following me” and wouldn’t leave me alone. I even told Karen to “go away” numerous times while holding her hand so that the girl I was dating felt I was making a strong effort to get away from her. When I got off the phone, Karen kept up with the gay accusations, so I very plainly told her that I’d be happy to prove to her how straight I am by fucking her brains out when we got to my apartment. She sort of sobered up for a moment at my bluntness, but soon went right back to being a drunken wreck.

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? Just before we got to my apartment, Karen fell and skid her knees across some rough concrete. She was bleeding, but too drunk to really notice. I lead her into my bedroom, stripped her of her clothes, and guided her face toward my cock. She continued giggling, sucked on me for a while, and I propped her up on my bed in a doggy-style position. I started fucking her from behind and decided to stick with my decision of treating her like a fuck toy. So I grabbed a large chunk of her hair, yanked back on it so that her face was looking straight up, and fucked her from behind about as hard as I could. She moaned and grunted in pleasure, presumably having no problem with how rough I was being.

I have to admit, I was a little disappointed that she wasn’t the least bit resistant to how rough I was being. I’m not into rape, but I definitely like pushing the limit to see how much I can get away with. The next best thing I could think of was fucking her in the ass. So I pulled out, got out of bed, and grabbed a condom. She said something like, “What happened to the one you were already wearing?” assuming I had one on to begin with. I lied, told her it ripped, and got back on the bed. I started to fuck her pussy again, giving her a chance to get back into the rhythm of things before I surprised her.

After a few minutes, I pulled out, spread her ass apart with my left hand, lined my cock up with her asshole, and thrust really, really fucking hard. I didn’t get much more than the head of my cock in, but Karen let out a cry which was mostly pain. “That’s my ass!” My response wasn’t planned, but it came to me quickly and naturally. “You said I was gay, didn’t you? You should have known I’d want to fuck your ass.” Her body tensed up quite a bit, making it difficult for me to get any deeper into her asshole. After a few minutes of attempted thrusts, which she never once protested against, I pulled out and got off the bed. My intentions were to make her kneel down so I could jerk off onto her face, but unfortunately for me, Karen finally noticed her leg was bleeding.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even 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? She went straight to the bathroom, sat on the toilet, and began to wipe the blood off of her leg. I put a band-aid on for her, decided I was tired, and told her that she had to go. She looked extremely offended and shocked. “You’re kicking me out?” I lied to her about how I had already told her that I had to work in the morning (not true) and that I made it perfectly clear earlier that she couldn’t spend the night (also not true). She got dressed in what I can only describe as an incredibly embarrassing manner. She was pretty much pleading with me to let her stay because she had no way to get home and was still drunk. I was being an asshole and didn’t care at all. It was around 3am and I just wanted to sleep. I didn’t want to have to deal with her for the rest of the night or the next morning, so I practically had to push her out of my apartment. Once she was outside, I closed the door and locked it.

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

What were your motives for this hookup? Fun, pleasure, horniness, Thought it was an important experience to have, To feel better about myself, Power / Dominance, Revenge / Getting even, Boredom, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

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

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

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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? I told the girl I was dating this long elaborate story about how Karen followed me home, scraped her knee, and I allowed her inside to help her clean up the blood. I told her that Karen then just started stripping her clothes off in my room, so I made her get dressed and kicked her out. It’s easier to remember a lie when it runs parallel with the truth, so the only thing I really left out was how I fucked this girl like a piece of meat.

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

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? Very

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I was able to fuck and humiliate a girl who I frequently fantasized about in middle school.

What was the WORST thing about this hookup? She had added too much weight, had a brash personality, and I wasn’t overly attracted to her.

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup? I only saw Karen once more in my life. It was about a month or so later at the same bar we mutually frequented, only, this time, when our eyes met, she gave me an extremely shy and uncomfortable look. We both looked away from each other and avoided each other for the rest of the night. I never saw her again.

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