Young and Incredibly Stupid



What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Student
What’s your current relationship status? Single
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 1

Young and Incredibly Stupid

How long ago did this hookup happen? 3 years ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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 a short and very cute brunette. She was exactly the type of girl I’d been dating at the time and had the best curves I had seen at the time. She had just recently been hired at the restaurant we worked at and it was her first day, and we were working a large party together upstairs. I was the main one who worked those parties so I was training her. She had been flirting with me, at first I wasn’t very receptive but as I played into it a little bit she got more and more direct and aggressive. She definitely knew exactly what she was doing.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Towards the end of the shift she had flirted with me enough to get me pretty turned on. We walked out to the parking lot afterwards and she made a move. She grabbed my dick through my pants, looked at me and said I want this. Having been young and still living with my parents at the time, I told her to follow me back to my place. She followed me over, parked down the street a little bit and quietly made our way to my bedroom, careful to not disturb my parents so they wouldn’t come and say hi to me before going to bed.

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? Once we were in my bedroom we started fooling around, but lightly as to not make any noise. We laid in my bed and made out quite a bit, with a lot of exterior rubbing. I slipped my fingers in her pants and started fingering her furiously, she was already super wet and apparently very ready after a few minutes. At that point she whispered that she was desperate to fuck, so I slipped out of my room really quick to make sure my parents were asleep. Luckily they were.

I rushed back to the bed and without saying anything pulled her pants and underwear off, revealing her unshaved and extremely wet vagina. I had never been with an unshaven chick before, and something about this turned me on more than I’d ever been before. We both finished undressing and she laid on her back, legs spread and pulled back. I had never had sex without a condom before, but something about how erotic this whole situation was made me not care anymore. I got between her legs, slid myself in and started pounding into her as hard as I could.

We fucked like crazy, changing up the positions a few times, and after not so long I felt myself about to cum.  asked her where she wanted me to cum, to which she replied anywhere I wanted to. I was about to pull out but right then she pulled me into her with her legs, and just like that I was blowing my load into a girl for the first time ever. For another couple hours we mixed between making out, foreplay and unprotected sex before we were drained and she left.

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? The next time we worked together it was kind of awkward. She really liked me but I only saw her as a hookup, and she got a bit clingy. It was actually kind of weird for me, because I would have never thought she’d see me as relationship material after our first encounter. I had planned to hook up with her regularly, but then I had a scare.

At the time I thought she was on birth control, but turns out she wasn’t. I found out a week later when she took a pregnancy test and it came back positive. I heard through coworkers, and I was freaking out until I asked her directly. She said it definitely wasn’t mine, but wasn’t even sure if she was pregnant or if it was a fluke. Turns out we sort of bonded over being worried about pregnancy, and from that point until I moved we became friends. Turns out she did get pregnant by someone else, so we ended up using that as an excuse to have unprotected sex a couple more times.

Given that this was my first experience having unprotected sex I dodged a huge bullet, but it gave me a lot of insight to safeguard myself in future encounters.

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), Learning new things, experimenting, To feel more confident, Making new friends

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? I talked to some coworkers about it, but not about the details. Turns out she had a reputation for fucking, and she knew how to get guys in the sack. This was the first time I had experienced someone like this, and not feeling guilty about it I was more comfortable having sex with her the couple of times after.

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

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? Having sex without a condom and without pulling out for the first time. Also the extended period from when the flirting started to when we had sex made us more than ready for it, and it was the first time I ever threw caution to the wind when I had sex. Luckily I was able to take this experience, learn from it in more than one way, and make sure my partner is on BC before I cum inside.

Also, after all the worrying I learned to relax more when I had sex from then on. Which lead to two really satisfying hookups with her later on.

What was the WORST thing about this hookup? Finding out she was pregnant shortly after we had sex. At the time it also sucked knowing that I was just another guy she fucked recently. Ever since this experience, I am hyper-sensitive about these things beforehand since I dodged such a big bullet.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, make sure they don’t have so many partners and that they are on birth control. Luckily this stupid experience when I was young lead to safer experiences later, so I can’t say I regret it at all.

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

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

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