What’s your gender? Woman
How old are you? 28
What’s your race/ethnicity? Middle Eastern
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Assistant/sales
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? nope
How many sexual partners have you had in your life (including oral sex)? Over 20
How many hookup stories have you here posted before? None

Casual Sex on a Work Trip

How long ago did this hookup happen? 5 months

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

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? Two partners:

Milana, cute Central Asian colleague, same age and sense of humour as me, pretty lovely with big eyes and a nice curvy figure. I’d known her for a few months but only got to know her for real when were partners on a multi-city work trip.

Josh, cute videographer we met at a hotel bar in Michigan. In his thirties, bearded, long hair, fit body, easy going, very sexy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Milana and I had been getting closer as we’d been flying from city to city to give a presentation to the various branches of our company. We started sharing a lot, getting drunk together every night and one-upping each other with stories from our pasts. At some point along the way I started feeling attracted to her and some tension crept into our relationship.

At a hotel in Michigan we found a drinking buddy in Josh, who we hung out with at the hotel bar over the course of the three or four nights we spent there. When he wasn’t around Milana and I would joke about how much we both wanted to fuck him, because he was cute with a really chill vibe and we were snowed in with nothing else to think about. Before meeting him on our last night there, we asked how we would decide which of us would actually sleep with him, since we couldn’t tell who he liked more. In a moment of courage I suggested we share him, and Milana laughed and said she had the idea but was too afraid to mention it. When Josh arrived, after some drinks we invited him up to Milana’s room.

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? A little nervous at first at the idea of a “threeway,” I asked Milana and Josh to start while I watched from the couch. This turned us all on quite a bit. Josh was unleashed on Milana and it was so sexy watching him rip her clothes off, and finally seeing that voluptuous body of hers I had thought of for so long now. Milana obviously got off on being watched, she kept looking over at me as Josh fucked her. Every time she would look over at me my heart would leap and I’d get a little wetter. When she was about to come Milana asked me to kiss her and I laid next to her and made out with her until she came, making these little high pitched moans that made me so wet.

Josh gave me an awkward smile and asked if I wanted to go next and I asked him to lie down. I slipped off my underwear off from under my dress and started going down on him as Milana gently massaged my clit. Feeling Milana’s hand on my clit made me so close to coming I had to change position so I could enjoy Josh, who I knew I’d never see again. I started riding him until I came, and then I collapsed next to Milana, both of us laughing at what had just happened. Josh asked if he could come on me and I agreed in the spirit of the moment. I pulled my dress down to my waist and he came on my face and tits, and then Milana licked me clean. It felt so nice to have her lips on my tits.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? I showered in Milana’s room and we said goodbye to Josh after another drink and all went back to our rooms.

The next morning Milana and I flew to Des Moines and spent the next day giving our presentation. The tension was pretty thick after what just happened, but during a lunch meeting she put her hand on my thigh for a moment at that point I knew she wasn’t freaked out, but the opposite. A couple hours later she was going down on me in my hotel room. We slept together almost every night for the rest of the trip, and we’ve been hooking up on a steady basis since then. Even when I was seeing another woman for a short time, Milana would join us.

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? 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? A few trusted friends. Nobody cared much.

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? Finding a sexual partner in someone I had only known professionally until then, and sharing a sexy guy with a girl I liked and trusted.

What was the WORST thing about this hookup? I don’t love when a guy comes on me but I didn’t mind, and Milana might not have sucked on my tits if he hadn’t.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. I hadn’t been with many women before, now I pursue them confidently.

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

All things considered, how NEGATIVE was this experience? Very negative

Anything else you want to add about this hookup? Nope.

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 like it, but I have had bad experiences.

What do you think about the Casual Sex Project? I love it. The stories turn me on and I’m glad other people are sharing.

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