by Jess


Gender: Cis-gendered female
Age: 24
Race/ethnicity: White/Mixed
Location: Thailand
Highest education received: College degree (eg., BA, BS)
Occupation: Ed
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Gay/Lesbian
Any other term(s) that describe your sexual orientation/sexuality better/best? Queer
How many hookup stories have you here posted before? Zero


The Poly Professor


How long ago did this hookup happen? 5 months ago and again a couple of weeks ago

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 was on my way to bed when a friend of mine invited me out for a drink right around the corner from me. I decided to go for one glass of wine since I hadn’t seen my friend in a while and when I showed up she was with someone I had never met before. The new woman before me was an attractive, petite 36 year old with reddish-blonde hair and the most confident smirk I had ever seen on a woman. She was incredibly hard to read, but there was something about her I couldn’t shake. I felt like she was looking right through me and when she asked me for a drag of my cigarette, I had decided then and there I was going to try and sleep with her. The catch was she had/has a girlfriend, and even though they were technically in an open-relationship, her girlfriend didn’t want her to sleep with women (as she was bisexual) or with anyone who was in their “sphere” of friends.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few days after we first met, we had dinner with two mutual friends (who were also good friends with her girlfriend) and ended up going out for drinks after. I had been drinking steadily all day so as the night progressed, I became more obvious in my flirtation with her and eventually she came back to my apartment under the guise of having another drink since the bars had closed. Once it was just the two of us, it was pretty obvious she was waiting for me to make some sort of move, so I asked her if I could kiss her and she said “yes.”

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The first night was a bit of a blur, but mostly I fucked her vaginally and also went down on her a number of times. We tried multiple positions all over my apartment. I don’t think we went to sleep until 4 or 5 in the morning. It was exciting, super sexy, and, most of all, fun. She knew exactly what she wanted and wasn’t afraid to ask for it which I loved. For a week, we continued having sex, every time it got better and we became more comfortable expressing what we wanted. We added in a little spanking, scratching, hair pulling, and anal. She always slept over and there was a little cuddling, but we never held hands. For some reason, for the both of us, we just knew that was the thing that would cross the line from casual sex between people who were just fucking to something that would probably (definitely) displease her girlfriend. Easily it was the best sex of my life, but like all good things, it came to an end when she had to go back to the US.

Then the other week, while I was on a trip back to the US, I went to go visit her for a weekend. Once again, for two days straight, we fucked. A lot. We would eat and try to sleep, but mostly we just had sex. This time I wore a strap on so that added a new element to our sex that I think we both thoroughly enjoyed and we both had multiple orgasms (although she had more than I did but that’s because I prefer to do most of the “pleasing” in bed). Since then we have texted once or twice, but I don’t think we really plan on keeping in touch and at this point I don’t know if I’ll ever see her again.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not take any precautions or discuss STI history.

What were your REASONS for having this hookup? In college, I had all of these crushes and sexual fantasies about older women, especially my professors. When I met this woman, my friend had introduced her as her old professor who was queer and I just knew I wanted to go for it. I also hadn’t had sex in 6 months at that point as I had gotten out of a long term relationship right before I had moved to Thailand. Everything just seemed so right, and dare I say wrong, that I knew I wanted it. I wanted her.

Were alcohol or drugs involved? If so, how much? We both like to drink and I like to smoke weed. But I would say half of the time we had sex we were completely sober. Especially when we had morning/day sex.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We keep in touch every now and then though I have a feeling it will be less frequently now. When she first left Thailand we sexted on a daily basis (something I had never really done before). When her girlfriend found out about our affair by reading her Facebook messages, we didn’t talk much more than a hello here and there. I try to not have any hopes or expectations with this woman in the future. Part of me would love to keep having our sex rendezvous, but I have a feeling if I get into a relationship it will be much less likely. It also takes me a few days to readjust to life after I see the professor. It’s weird to go from constantly having the best sex to nothing or sex with other people that fails to compare. I also feel shitty that I’m the “other woman” in a lot of ways. Being with the professor is great in the moment, but it never seems like a good idea after the fact.

To whom did you talk about the hookup? How did they react? I’ve talked to a number of my friends about it. They mostly think it’s a funny situation, but that it’s awesome at the same time. Some of them have cautioned me on what I’m doing, but also know that I’m an adult and will make my own decisions (though it feels as though my vagina is making most of the decisions in this case). Our mutual friends were surprised (we hid it from them at first), but ultimately know we’re two consenting adults. Overall, the responses were positive.

Was this a consensual and/or wanted experience for you? For your partner? Consensual and very much wanted on both sides.

Do you regret this hookup? If so, why? No, not really… I mean, I will probably see her on and off until something comes up and changes the circumstances. I usually don’t feel great right after I see her, but I don’t think it’s about regret. I think that I have a lot of guilt issues about our situation, but clearly it doesn’t stop me.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing is that we just have amazing fucking chemistry (literally). The sex is incredible. It’s always interesting, exciting, and fun. We also get along well which definitely helps. The worst thing is that she has a girlfriend. That’s bad, not because I want to date her myself, but mostly because I’m knowingly taking part in an affair. Even though they technically have an “open” relationship, it’s also clear that when the professor is with me, we’re breaking a lot of rules. I think this situation has made me think a lot differently about casual sex. Since we first had sex together, I’ve had a lot more casual sex in the last six months than I have in my entire life. I’ve learned a lot about separating feelings from sex and how to have good, communicative sex with someone you’re not dating.

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

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

Anything else you want to add about this hookup or anything else? I hope I get to have sex with her at least one more time.

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