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What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New York
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Administration
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
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)? Twenty
How many hookup stories have you here posted before? 0

Hottest Girl At Work

How long ago did this hookup happen? 23 years ago

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 less than 6 months

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? This was the early 90s, we all worked in a local bar/club hotspot. I was a barback and she was a waitress. Every guy wanted her and she was known as the hottest girl on staff. Her personality made her ten times hotter because she was so sweet and down to Earth. She had an amazing body, a perfect ass and tits, and this amazing inner thigh gap you couldn’t help but stare at. All the waitresses wore these spandex type shorts so her body was always so tempting, especially when she would bump into you and you’d feel the firmness of her ass. She had shoulder length light brown hair, a naturally pretty face like a model, and these piercing blue eyes that made you melt. She was always chewing peppermint gum and wearing this perfume called New West, not too much but just enough that you wanted to get closer to smell her more. You always knew where she just was because you would get a whiff of peppermint and her perfume which is an aphrodisiac to me now if I ever smell that combination again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Everyone myself included always assumed she was off limits because she always talked about her boyfriend and they seemed so happy together. As hot as she was, you always got the impression she wouldn’t have a slutty side to her so no one really tried, but every guy drooled when they saw her. There was this basement at the bar where all the alcohol was kept and where more than quite a few hookups also happened with people that worked there. One day I was down there and turned the corner and literally walked into her and her perfume intoxicated me because she always smelled so good. It was awkward but she said: “I thought you were gonna kiss me for a second!” Without thinking I blurted out that I would love to if I had the chance and mid-sentence she pulled me close and we started making out. I almost came in my pants and I had my hands all over her firm ass and I ground against her pussy through her spandex shorts. We stopped the kiss and she giggled and went on her way, but I stood there dumbfounded.

The next day at work she smiled at me and asked for help with carrying up glasses from the basement and I knew what was up. She grabbed me and we started kissing and she pushed my hands down her shorts and I felt her perfectly shaved pussy which was dripping. Girls only just started going smooth back then, so this was like a trophy. I pulled down her shorts and sat her on some boxes and pulled down my shorts and entered her as she muffled her moans in my shoulder. We fucked like that for four or five minutes until I was ready to explode. I told her I was gonna cum and she said: “go for it I’m on the pill” (hottest words I ever heard)! I exploded inside of her and she orgasmed, digging her French manicured nails in my back and burying her head in my shoulder to muffle her screams. I could smell her perfume in her hair and it sent me over the edge while still in shock I was fucking the hottest girl at work. We got dressed quickly since we were at work and for the rest of the summer that I worked there, we would do that almost daily.

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? If you work in the night club or bar industry hooking up is common, but we still kept our fling hidden since she had a boyfriend. Sex was always at work and it always had to be quick so it was always straight penetration. Occasionally she would give me a blowjob, and other times I would bend her over for doggy style. She is still my best sexual memory and the best pussy I have ever fucked. We never really talked about it much, as this was the 90s so there was no texting or social media and she did have a boyfriend. She did acknowledge the boyfriend part and the way she explained it to me was she was young and wanted to have fun. I’m pretty sure she wasn’t promiscuous and that I was her only hook up at the time. It was always such a turn on to me after we fucked that she would stand in the parking lot smoking a cigarette waiting for her boyfriend to pick her up, get in the car, and kiss him hello all with my cum still inside her. And he had no idea.

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? It was a summer fling; we were all in our early 20s and it’s good memories. After the summer I went back to school and we ran into each other a few times, but never spoke about it. I definitely would have pursued it further if she didn’t have a boyfriend, but I was happy I was fucking her anyway.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Just happened, I don’t know why, just went along with 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? 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? Mostly my friends and years later some people I use to work with that also worked with her. They respected me because no one had any idea and we kept it so quiet.

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

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? Not at all

What was the WORST thing about this hookup? That it didn’t last longer

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really, I was in my early 20s and so was she and it were the best of times. Plus, there were plenty of years ahead of me to have more fun.

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

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

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