Casual Ex

by Jay

Gender: Male
Age: 24
Race/ethnicity: White
Location: CO, USA
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Student
Religious affiliation: N/A
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? None

Casual Ex

How long ago did this hookup happen? Today

How would you best classify this hookup: Sex with an Ex/ FWB

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 very short, and very beautiful–part Italian, Spanish, and Native American–petite, but thick in the right places. We were together from August to December of last year, during which time we moved in together (way too soon), and after a lot of stress and drama, broke up and I moved out. It took a while for us to get back on good terms, but we eventually did and have been friendly for the last couple months while she continued to stay in the apartment we had gotten together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She messaged me early this morning with, “Hey guess what?! I got a new job! But have nothing to do today, so if you are free do you want to hang out?” I replied that I would see if I could break my plans, to which she replied that I shouldn’t break them and she would feel bad if I did. I said, “Are you sure? It’s been a while since we’ve seen each other…” testing the waters to see how persistent she would be. She said, “Well can you reschedule?” So I did, satisfied that she really wanted to see me, and I ended up going to see her. (In my experience, the term “hang out” is becoming more and more of a euphemism for my generation when we want the intentions of a male-female meeting to remain opaque.)

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? She greeted me with a big hug when I got there, and immediately headed for what was once our bedroom, where she plopped down on the bed. She was wearing a small black sleeveless top, exposing both her black bra and some cleavage, tight jeans, and black boots. I laid down on the bed next to her and we just talked about random stuff for like half an hour until it started. (Note to guys who struggle, as I have in the past, with making the first move in for the kiss when you aren’t 100pct sure if the girl will go for it or not: What I did today I believe to be an excellent and replicable strategy which I plan to test going forward.)

She has very small hands, so somehow we came to comparing hand sizes, which led to hand caressing, which led to arm caressing. I positioned myself so that our hands blocked each other’s faces from each other, then leaned forward, peeled back the curtain we had created and went in for the kiss in one fluid, but deliberate motion. She accepted and leaned back as we engaged in simple, yet passionate kissing (very little tongue, eyes closed) for a few minutes, after which we alternated removing clothes, ending with her wearing only her bra and me only wearing my socks. We assumed the missionary position and stayed in it for the duration. It was over sooner than I would have liked, since I had not been with anyone else since we broke up and was uncontrollably excited. She has never been a very expressive love-maker, but not an impeding one either.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We have never used condoms, but she has always been on the daily birth control pill. We have never discussed STIs or anything related, and have never had any scares with either infection or pregnancy, even with a couple past internal finales. When I finished this time, I deposited my (rather voluminous) inventory on her stomach and chest– which I always feel a little bad about…but not enough to aim somewhere else.

What were your REASONS for having this hookup? She is the most attractive girl I have ever been with, and our considerable relationship issues notwithstanding, I still care deeply for her and we have had two different delightful days together in the last couple months (the previous one only ending in a prolonged kiss).

In addition, guys–especially those who follow sports–keep track of streaks, particularly dry spells, and we want to break those before they get so long that it starts to mess with our self-confidence. I was more than 50pct sure she wanted to have sex, and then when she went straight for the bed it was a done deal. I assume that on her end she still shares many of the same feelings for me that I have for her, but in a much more fleeting, impulsive, and inconsistent way. Part of the reason we broke up was her unwillingness to be intimate, which I did not understand before, and now have given up ever understanding. Just going with the current flow…

Were alcohol or drugs involved? If so, how much? None that I know of on either side, but I sure had a beer later when I got to my friend’s house!

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? This was the best part. We cuddled together under the covers (which she rarely wanted to do while we were together!) and we watched a bunch of YouTube videos on her phone. Then we went out to lunch, I dropped her off at the apartment after since she started her new job at 4pm. We did not kiss at parting as before, but hugged deeply. She asked me to message her when I got home, since it’s a journey of a drive (different cities). I did, told her I had a wonderful time with her, wished her luck on her first shift, and told her to let me know how it went.

To whom did you talk about the hookup? How did they react? I told my friend when we were hanging out later. He had met her and knew most of the details of our relationship. I emphasized the profoundly drama-free and positive vibe of this casual FWB relationship she and I seem to have cultivated, to which he replied that someone always catches feelings, hence it can not sustain, or end well. I replied that it won’t be me, since I know I can never trust her, and if she does, the list of conditions I will mount for her to meet to be my girlfriend again are most likely not possible for her to achieve (and if she can, great! We can try again.).

Was this a consensual and/or wanted experience for you? For your partner? Absolutely on both ends. Reasons be damned.

Do you regret this hookup? If so, why? I resisted the urge to try to have sex with her the last time we hung out because I feared the complications and drama that would most likely ensue (and also wasn’t as sure she wanted to), but so far there has been none, and even though the intercourse was short, it was very sweet, and she still turns me on as much as ever, so no regrets at all.

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 smoothly we transitioned from polite conversation, to sublime love-making, back to talking, laughing, and watching videos. No awkward conversations assessing “where we stood” with each other, or “what this means” or adjusting expectations going forward. I avoided prying questions and anything that would have broken the unrelenting positive nature of our entire time together today.

The worst would be that I couldn’t hold off the grand finale, and I was pretty sure she wouldn’t be down for a round two (which she wasn’t), so the physical experience was brief and fleeting, but its basic occurrence was more important to me than its overall quality.

I have very rarely tried to engage in casual sex in the past. Almost every time, I was trying/thinking/hoping that the encounter would result in or keep a relationship going. This was a profound and delightful introduction into the world of casual sex, oddly coinciding with my reading of the other stories on this blog and reading about the subject in general. Given my cynicism (largely due to this last relationship) on fidelity, caring, and long-lasting relationships, casual sex is something that I will have to take more seriously moving forward, so as to keep from being pulled back into the crying, screaming, arguing, cheating muck that is the unrealistic expectations I believe we have for each other in relationships.

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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