Unexpected Hookup with Ex

by Jay

What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Academic
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Catholic
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? none

Unexpected Hookup with Ex

How long ago did this hookup happen? Two years ago

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

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

How long did you know the person before this hookup? For 1 to 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? She (I’ll call her Pauline) and I had had a relationship a couple of years before this occurred. Shortly after we started to go out, she had to move to another city for work for what she said would be a couple of months (later turned out to be six, but anyhow). She was a couple of hours away from me so we didn’t see much of each other. We mutually decided to keep the relationship going, however, since the arrangement would only take a couple of months, after which she would return to the city where we both lived at the time. She was tall, Hispanic like me, white skin, very dark hair, she had amazing breasts, large and round, slightly curvy in a nice way, voluptuous and also good looking. She dressed nicely, was smart as a whip, and fun to be around. I loved to fuck her and that was another reason I didn’t want to break it up when she had to go work to another city. However, the distance started to take a toll in our relationship, and although we started seeing each other every weekend after she left, within a couple of months I started seeing and hearing less and less of her. She would make up excuses not to see me, and I started suspecting she was two-timing me. Eventually I found out about it. It turned out she was fucking some colleague of hers. I told her we could have arranged to see other people while she was away, there had been no need of lying and deceiving, but before she left to work at that other city, she had insisted we maintain our relationship. Sly little one she was. We broke up and did not hear much from her thereafter.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? About two years went by and I got married and moved away from our hometown where I had met Pauline, she didn’t marry nor was she in a steady relationship at the time, she kept on working the same job, moving eventually to a bigger town, a couple of hours away, but she visited our hometown every once in a while.
We had texted each other every once in a while and at least on my behalf, I had always felt the desire to fuck her at least once more after our breakup given that she was great in bed. If anything, she might have been a liar but she knew how to fuck well and had a very healthy libido. One day we were texting and told her I was in town on holidays, and so was her. She then asked if I wanted to meet for coffee and talk. It was kind of unexpected and we had not seen each other since the breakup. We met at a coffee shop near her parent’s place where she was staying and caught up with our lives. The whole time I just had one thing in mind, and so I started to place my hand on her leg under the table, flirt with her, and make advances. She was receptive, did not bulge when I started to touch her leg, and things started to heat up. We got out of there and got a room at a motel.

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 was so aroused the whole time, when we were alone we just went at each other like dogs in heat. We kissed passionately and I loved tasting her again, her smell and her body smelled fantastic. We got naked and she lied on the bed and I gave her head as she used to love. I ate her pussy and she was literally dripping wet. I then told her to get on all fours, I grabbed her hips and I started ramming her from behind almost violently. I felt great, there was a mix of resentment at her having cheated on me mixed with raw sexual desire that just exploded. I just held her hips and fucked her mindless like we used to when we were a couple. She moaned just like when we fucked when we were together and I loved every moment of it. As I was about to cum I asked her to suck me off. She grabbed my cock, gently sucked and in no time I came in her mouth and she swallowed every drop. We then took a break but did not stop. I then started touching her clit and rubbing it while I gathered strength. We fucked again until we were both exhausted. The whole time she played out her part as expected, she had a way of making me so horny, like whispering in my ear how she missed me, how she loved my cock, and swaying her hips, controlling the rhythm and then asking me to fuck her harder, pulling me with both hands toward her. We must have been at it for two hours straight. After we were completely drained, we then lied on the bed, eventually took a shower together (while making out and having a final, more mellow fuck under the water), and went our own ways.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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 did not text her next day or for a while after that, and we didn’t discuss it at all. When we were dating, I remember her telling me how she liked casual sex and that was how she handled hookups before meeting me (and while we were together, probably). She said when she would hook up, she would go to a hotel, fuck, and go home, no feelings attached. So I assumed that was how she felt about it this time with me. When we briefly texted over the course of the next weeks, the subject was never addressed. I felt slightly bad about it because of my marriage, but I could not pass the opportunity, it was an amazing fuck.

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), To feel more confident

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? No one.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Sex with an ex, under certain circumstances, can be amazing. After learning this woman had cheated on me, I cannot deny I felt resentment towards her and I think this hookup was a way of feeling better about myself. The best thing though was the amazing sex. I was so driven and fucked her like I had not fucked in years. She was great too.

What was the WORST thing about this hookup? Feeling guilty.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope. I would do it all over again.

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

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

Anything else you want to add about this hookup? Nope, it was electrifying.

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 have always been somewhat conservative about casual sex, preferring relationships instead. I think I should have had more of it when I was single and younger, I think casual sex can be liberating, an emotionally and physically exhilarating experience, at least for people like me, who possess a high libido. People should have more of it, as far as I am concerned.

What do you think about the Casual Sex Project? Great, love it.

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