Coworker One Night Stand

by JimmyJ

What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Sales
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
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)? 5
How many hookup stories have you here posted before? 0

Coworker One Night Stand

How long ago did this hookup happen? 11 years

What was your relationship status at the time? Single

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’ve known Heather for well over 5 years. We were always coworkers and I’ve had a crush on her since we started working together. She was dating her boyfriend at the time and I was just casually dating here and there. We had this great connection and she is a heavy flirter, but nothing ever came out of it and it seemed like I was friend zoned. On the one hand, I was sort of upset about this, but on the other, knowing her, she’s not someone I would date long term. Either way it was going nowhere fast. She eventually got married and had a kid. One day we were sent on a business trip for 4 days with few people. We spent first 2 days in training, teaching others sales so it was a bit boring, but after work we all would just go out to have dinner and drinks. Basically fun stuff.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On the third day, we all went out to a bar to celebrate the end of training. We were all pretty much there the rest of the night and we all got pretty tipsy. We didn’t even flirt since we were with coworkers. We got back to the hotel and only we got off on the 2nd floor as our other coworkers had rooms on 3rd floor. I was about to go into my room when she said she wasn’t tired yet and wanted to see if I want to hangout in her room for a bit. I said sure. I actually didn’t even think or try to hook up as we had known each other so long and since she is married and had a kid about 5 months ago I was cool with just moving on. As soon as I got into the room, she started kissing me everywhere and she pushed me down on the little couch in the room. She was all over me and as she was on top she started to unzip my pants.

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? She took my pants off and my boxers. I was already hard and she just looked and said “hmm you’re much bigger than my husband” which was strange as I’m probably 6.5-7inch on a good day, but it still felt good to be told that. She started sucking me and although it was not the best blowjob I’ve had, seeing your coworker that you had a crush on for a while just blowing you made up for her skills. She did this for about 2 minutes until she stopped. She stood up and took off her dress, bra, and panties and stood there naked. She cupped her tits and asked, “what do you think?” She had a stud in her right nipple which wasn’t a surprise as I knew about it, but at that moment it looked hot as hell. I stood up and started sucking on her tits while pushing our way onto the bed. We got into missionary position and I took my cock and just put it inside her. She was already wet and I didn’t even think at that moment to go down on her. Just that I wanted to be inside of her. As I started fucking her she started to become very verbal. Kept telling me how she is a slut and a cheating whore and how her husband doesn’t satisfy her and has a small dick. She said she wanted to be my whore for the night. I mean she was really going on and on being loud and moaning my name while saying her husband is not the half the man I am. It was very weird as I’m not into humiliation at all, even if it’s someone else’s, but shockingly I liked the dirty talk as none of my prior girlfriends did that. It wasn’t anything mind blowing and as I was close to cumming I told her and wanted to pull out as we didn’t talk about condoms at all. The subject didn’t even come up. She told me not to pull out and started saying “nut in this pussy daddy” over and over. That sent me over the edge and I came more than I think I ever came before. I got off her and laid down. We talked about bullshit for few minutes, mostly her telling me again how her husband has a small dick and never satisfies her.

After few minutes, she started to suck my dick again and I got hard in no time. This time she said I got mine and she wanted hers so she got on top of me and started riding me. Watching her tits bounce up and down was marvelous and again she got into her husband ain’t doing anything for her and how she is a slut and a whore and wanted me to call her that throughout the rest of sex. She came pretty quickly after I started calling her that and finished riding me. I needed to get one more so as she got off I took her doggy and came probably within a minute or so. She wasn’t verbal anymore just quiet and moaning. While I did not come as hard as the first time it was still good amount and I pulled out and came on her back. We both fell asleep after that.

We woke up and she said she enjoyed our hookup and that it was the best sex she’d had in years. We fucked again in the shower, but it was no way as exciting as the night before, and in fact, there was no dirty talk, husband talk, or anything like that. When we finished, she wanted me to cum in her mouth instead and as I did she just spit it in the shower drain.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? Although that was the first and last time we had sex, partly because I left to a different department and she quit few years later, she did contact me through messenger few years later on Facebook. She wanted to see if I was interested in being a fuck buddy and she mentioned that she had her husband’s permission. In fact, she said she was a hot wife now and we could openly fuck in her house while her kids were at school and that her husband would like to watch sometimes. We chatted, but as I was married already and wasn’t into something like that, I told her I was not interested. She said she thought of me because I never talked about our encounter with anyone and that’s the last we talked.

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

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, To feel better about myself, Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Very

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? My best friend at the time after it happened.

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

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? I got to have sex with someone that I had a crush on for a while and it felt like a completed a task that had been a long time due.

What was the WORST thing about this hookup? Nothing bad, but I wasn’t into all the husband talk during sex. I feel like it caught me off guard and we could have skipped that.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It hasn’t. I got married few years later and been faithful to my wife.

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

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

Anything else you want to add about this hookup? No

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? No

What do you think about the Casual Sex Project? Great site to let out a secret you don’t want anyone to know.

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