What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 2
Coworker Wears No Underwear
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? Short fling
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? We were coworkers at a menial job. She was a cute mid-20s girl with brown hair, of mixed race, so a slightly dusky pallor. Very scrawny (as in, Kate Moss might have encouraged her to eat a sandwich). Had some tattoos.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We went to bars together with groups and I kept on realizing that she kept gravitating to me over some of the other guys working there. Then one day I decided to ask her to a movie and dinner after work. I thought I knew where it was going because over dinner she was acting very forward and flirty (kind of a new experience for me) and it was obvious that she wasn’t wearing a bra and chose skimpy clothing (cutoffs and a sleeveless shirt) that showed off her tattoos. In fact over dinner, I said something about what to do next and she said, “We’ll figure something out.” I’m not sure if we even had a conversation about going back to my place or if that’s just what we did.
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? We snuggled on my couch in my bachelor apartment. Eventually she scurried into my lap and we started kissing as she grinded on me (very exciting!). I took her shirt off (least appealing breasts I’ve ever seen, if I’m being honest — I don’t want to sound judgmental but they were strange droopy things). Otherwise, I had never encountered such a thin body, with bulging ribs and thigh bones, but I can’t say I was revolted by it — I found it appealing, at least as a novelty, compared to the fleshier women I had generally encountered. When we stood, she did a thing where she wrapped her legs around me and scurried up my body like a squirrel, ended up with her legs linked around my waist. I found it so exciting that I had her do it again.
From there it was to my bed, where I peeled off her cut-off shorts. Now for a big surprise: no underwear, just a drooling pussy staring at me. She had a nice little thatch of brown pubic hair with a little tuft at the top; I ran my fingers through it and complimented her. And then I fingered her, which liked and complimented me on.
I insisted on a condom before we fucked. Because she was so thin (and I was in relatively good shape at the time), this was probably the most energetic, acrobatic sex I’ve ever had, including a lot of changing positions mid-thrust. She was particularly fun in cowgirl position since she could basically fly up and down my cock, since she was light as a feather. It wore on, though — she seemed enthusiastic but not orgasmic and told me later (rightly or wrongly) that orgasms were rare for her. But I had not yet overcome an issue of having trouble coming inside women, so at the end I jacked off on her tummy, a nice big white sticky load on her flat belly.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, more than one
Did your partner have an orgasm? I don’t know
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 slept that night in a single bed (not too much of a problem considering how small she was) and in the morning, to my excitement, I realized that she had never removed my cum from her — it was dried to her, a fact she treated casually. She had a shower and then we had sex again.
Some time later we went to her apartment together. I was rather appalled at her living state (this was a crummy apartment poorly maintained in a bad neighbourhood) but was so horny I would have fucked her in the city dump. We made out on her floor and then on a foam mattress on the upper bunk of a bunk bed. Getting covered with uncomfortable foam was a small price to pay for an end to her horniness. I remember thinking during that night that I never knew sex could be this good, that her pussy was transporting me to another world of pleasure where the every curve of her insides and the contours of my cockhead were in perfect sync. But I didn’t come on that occasion either
Not sure if that weighed into the fact that, though we still worked together, she suddenly started ignoring me. One time she blew off a date we made without telling me. I quickly became aware that she had mental health issues, so perhaps I should take heart in the fact that dropped me so suddenly. But it does add a bitter taste to these memories.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
What substances did you consume? Alcohol
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
What substances did your partner(s) consume? Alcohol
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? I don’t know / I’m not sure
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 with a few friends, especially about how strange it was that she started ignoring me. But they intuited correctly that she was mentally ill and that I should count myself lucky that it didn’t go differently.
How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)
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? Somewhat
Do you regret this hookup? Somewhat
Why do you regret this hookup? I guess I don’t hate it because the memories of the physical act of sex are nice, but it’s clouded by the weird aftermath. Perhaps we should have communicated better about the fact that this was just a hookup.
What was the BEST thing about this hookup? Climbing me like a squirrel — the lack of underwear and her tuft of pubic hair — my dried cum on her tummy. Any of the three will do.
What was the WORST thing about this hookup? Her ignoring me, at best, afterwards.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It did make me more cautious for a while, because of how the postgame played out.
All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? A little negative
Anything else you want to add about this hookup? I often wonder
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? I do wish I did more of it when I could have. This was not my best experience but I still don’t outright regret it, it was a learning experience.
What do you think about the Casual Sex Project? It’s a fascinating repository of tales. Sometimes I come her for masturatory material — and certainly hope my stories might have supplied some for others — but sometimes just to read and be fascinated.
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