by Jay

Gender: Male
Age: 24
Race/ethnicity: White
Current location: CO, USA
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Student
Relationship status: Single
Religious affiliation: N/A
How religious are you?: Not at all
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? 1

Casual Ex (Part II)


How long ago did this hookup happen? Today

How would you best classify this hookup? Sex with an ex

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 is short, with long brown hair, and a compact-yet-thick frame. Described in more detail in the original Casual Ex post. We were together for a little over three months last year. We hung out a few times after breaking up, one of those times resulting in sex. I went into today thinking of her as someone I definitely still cared about, but not someone I could ever trust or be in a relationship with again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She texted me early in the morning asking if I was busy today, and that she wanted to hang out and was willing to drive to me (she lives over an hour away). After thinking about it for a few minutes, I replied that I would be free in the afternoon and she agreed to come then. Once she got here, we sat on my bed and talked for a while. She asked what there was to do. I was sort of feeling the vibe, but not totally. She mentioned she was hungry so I suggested walking down to this new ice cream shop that just opened up a few blocks away. When we got back we came back to the living room and sat on the couch talking more.

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 chose a quiet moment to gently guide her face over to mine and kissed her. She complimented my maneuver and we began to make out. I asked her if she wanted to go to the bedroom, but she said she couldn’t because it was her “full moon.” I said I didn’t care and after less than a minute we were walking to my room with her saying, “I can’t believe I’m doing this.” We made out passionately on my bed and stripped off all of each other’s clothes. I tried to extend the foreplay but she was impatient so she grabbed me and pushed me inside of her. We had sex missionary style, with a good amount of dirty talking (which in the past she always hated) that made it all the more amazing.

Did you have an orgasm? Did your partner(s)? I did, but she did not. She never has in her life.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We had never used a condom before. We talked about using one today, but once our clothes came off she said forget it. I asked if she was sure and she said yes. (I recently heard this joke that having sex with a condom is like going to the theater with sunglasses. It’s the same movie, just not as vibrant. Lol.) Afterwards she told me that she had been recently tested and was clean. I hadn’t been with anybody since her.

What were your REASONS for having this hookup? At first I wanted to resist having sex with her today because there is another girl that I am very interested in, but the other girl has made it clear that she is not ready for a relationship and it will be a while before she is. On top of my ex being the most beautiful girl I’ve ever been with, we also have insane chemistry–infinitely better since we’ve broken up. I was sitting there on the couch with her and just had to go for it, since every time with her has always been special.

Were alcohol or drugs involved? If so, how much? Just ice cream! Blueberry lemon is the truth.

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 laid in the bed naked and had a more honest conversation than maybe we’ve ever had. We talked about why we broke up and how everything that happened made us feel. She talked about the dates she’s been on since and how lame guys are. I told her about the girl I was interested in and how uncertain it was. We talked about how we still loved each other and that maybe in a few years we would try the relationship again–after she has traveled and “lived life” and I have finished my Master’s and have a more stable foothold on life. It made me really happy that she still felt that way for me and held me in her heart as a future possibility.

To whom did you talk about the hookup? How did they react? No one, and this time I think I’m keeping this memory just for me.

Was this a consensual and/or wanted experience for you? For your partner? Yes, even though I had to do a bit of persuading, by the time we got to the bed she was more ravenous than I was.

Do you regret this hookup? If so, why? Not at all. She’s still got a ways to go with her personal growth before it would be a smart idea to try and be her boyfriend again, but the love we have is strong enough to wait a while for our brains and our situations to catch up to our hearts. I think my labeling of her as untrustworthy was a little strong, and I want her always to be in my life in some capacity.

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 part was how she showed how much she wanted me, both physically and verbally, saying and doing just what I liked. And then looking into her eyes afterwards and her smiling at me as we talked. The worst part was that it was over too soon, both the sex (my fault) and our time together. It had been three months since our last time and I don’t know how long it will be until our next time. I wish everything that is keeping us from getting back together could be resolved now, but I know that it will take time. My worst nightmare is her finding somebody else in the meantime though…

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

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

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