Random Waitress Coworker Sex

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What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Student
What’s your current relationship status? Single
Religious affiliation:
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)? 32
How many hookup stories have you here posted before? 0

Random Waitress Coworker Sex

How long ago did this hookup happen? 2 Years

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a month

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 super cute brunette that was as short as she was skinny with hazel eyes. Her chest and ass weren’t large by any means, but her figure was very sexy. I always caught glimpses of her bending over in the kitchen before that. She was dating a manager where I worked, which was also a friend I had known for a while but wasn’t too close to. I didn’t know her well, but I always helped others when I didn’t have anything to do so her and I had talked off and on randomly about random things. I had never considered hooking up with her before then, given that she was in a relationship.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was at work one night doing something on a counter and she walked up behind me and grabbed my ass. I turned around expecting it to be someone just joking with me but instead it was her, just smiling at me. Later that night I saw her in a secluded area and came up behind her to squeeze her butt. She turned around and gave me a huge smile. I had gotten a little worked up since she had touched me before, so I was forward with her and asked what she was doing after work. She said nothing so I said we should hang out. Just then someone else walked into the area we were in so we just continued going about our business as if nothing had happened.

We hadn’t made any plans and I didn’t have her number, so after work I looked around for her but it looked as if she had left already. Figuring I’d just try to catch her next time I walked to my car and as I was unlocking the door I heard her say hey from another car in the vicinity. She got out of her car and looked around to make sure no one was watching and said ‘let’s go’, promptly getting into my passenger’s seat.

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? I got in the car and started driving and she suggested we go park somewhere. Not being many private areas to park I drove around the back of a nearby K-Mart and stopped in a secluded area. On the way there she kept glancing at me and put her hand on my leg near my dick. She seemed to be trying to figure out how to start something on the way there, but since I had a manual shift it was not so easy.

When I parked she immediately got her knees on the passenger’s seat and started undoing my pants. Given that she was taking control I figured I’d let her lead the way from here. She pulled my dick out and wrapped her mouth around it, sucking it pretty aggressively. At some points she would take her mouth off and look at me as she jerked my cock off, but the thing I remember distinctly is she was super messy. Her saliva was all over the place, drenching my dick and the entire surrounding area. After she tried deep-throating me a couple times I was more than ready to fuck. After probably 10 minutes she sat back in her seat and started taking her pants off, to which I did the same thing. I hadn’t fucked in a car before so I just slid the seat back and laid it down. She started straddling me after she had stripped all her clothes off while I was trying to get the condom out of my wallet, but then she told me I didn’t need one if I didn’t want because she was on birth control and didn’t like condoms. I couldn’t resist, I pulled her to me and started making out with her, grinding my cock against her clit to tease her a little bit. After a couple minutes of some of the most intense mouth action I’ve ever had, she moved up a bit and slowly slid my cock into her pussy.

At first we fucked slowly as I licked her nipples, but most of the time we just stared at each other as we fucked with slow long strokes. As I got more into it I grabbed her waist and started grinding into her deeper. At some point I got the right angle and she moaned so loud I thought she was going to blow out my ear drums. She started cumming, but instead of slowing down she made these huge thrusts burying my cock deep inside her. I didn’t expect both the hard thrusts and her pussy squeezing my cock as hard as it did, and given our position I couldn’t pull out so I just unloaded my cum inside of her. I could tell she was surprised when I came, but kept her pussy on my cock until I finished.

She finally adjusted adjusted and pulled her pussy off of my cock, which unleashed a waterfall of cum back onto my cock. I opened the door and we both got out, but she was obviously not happy with me. She told me that she didn’t tell me I could cum in her while she stooped down on the ground and tried to get it all to drain out of her, but I told her that I thought it didn’t matter since she was on birth control and that I was trying not to cum when it happened and I couldn’t pull out. She thought about it for a second and understood, but told me I owed her another fuck since the first round was only about 10 minutes. After she got most of the cum out of her we got into my back seat and I pounded her for a good 20 minutes mostly doggy style until she gave me the go ahead to cum inside her. I blew my load in her again and we both got out of the car again to get the cum out of her pussy.

After that I took her back to her car, on the way back saying almost nothing to each other.

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 literally never talked about it again or had sex, but we would always smile at each other when we’d see each other. Something about that drove me nuts. I planned to have sex with her again but I didn’t work in that restaurant long, and I never got her number.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, 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, It was easy / convenient

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? 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? 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? Literally no one.

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

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? Not at all

What was the BEST thing about this hookup? Hot spontaneous sex in a car, all new for me at the time made it really exciting.

What was the WORST thing about this hookup? Fucking in a really confined area was pretty challenging.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not 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? Hasn’t happened too much, but this time it was pretty positive and satisfying.

What do you think about the Casual Sex Project? Pretty amazing.

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