Not So Casual Fling


This post is sponsored by Trust Massage Oil.


What’s your gender? Man
How old are you? 26
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? England
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Student
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 22(+)
How many hookup stories have you here posted before? 3 or 4

Not so casual fling

How long ago did this hookup happen? A couple of months ago

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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? We started talking on Tinder then went out for drinks/dinner later that day. Her profile said she was just looking for friends. I took that to mean something casual. Turned out that she and her ex and finally parted ways the day before after being on and off again for a while. She didn’t seem up for anything (too) sexual and seemed to be put off the idea of casual sex, seeing it as too hard for her and people generally to divorce from love & intimacy for biological reasons. However, we ended up having a great chat then going back to mine. She was slightly hesitant about coming back to mine, but I assured her i was a safe guy. We talked quite intimately and I tried to see if she would be happy for me to put my arm around her. She wasn’t because she said she didn’t want to get feelings for someone new so soon. Later that evening, we hugged a couple of times. Once when she was upset and again before she left.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Next day we decided to hang out again. We went for lunch then spent time out in the sun. It was a great day. We went back to mine where i cooked dinner. It was clear that I wanted something physical, and she was kind of in two minds. She went to kiss me on the cheek, but I thought she was going for a proper kiss, so I went in for that and that’s what we ended up doing and it progressed. Only later did I find out she was only going for a kiss on the cheek, but thought “okay, I’ll just go along with it.”

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? It was a great make out session, which led to clothes being taken off. She suggested going to my bedroom. When we got there, we didn’t go straight for the bed. Her ex had clearly not cared much about her sexual pleasure, and she had only ever had two sexual partners. Because of that, I wanted to give her an amazing time. I pushed her up against the wall and ended up lifting her up between it and my body. I was passionately making out with her and paying attention to all parts of her body. She was very reactive to my moves, moaning and moving around with pleasure. Eventually, we got to the bed where she said she wasn’t ready to have sex. I asked if she was okay with other things, and she was. I performed finger and oral on her. She gave me a handjob.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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 felt great. What was particularly nice was how reactive she was to what I was doing. It gave me confidence because sometimes i have partners that aren’t so reactive, vocally and physically – though they tend to want to have sex again. Different people have different tastes. Some women find it easy to orgasm. Others find it more difficult. It’s all about communication. However, in this case, we didn’t need to talk too much to get it right. She was amazed at how much foreplay there was and how much time I devoted to her pleasure. It’s amazing to do that to someone. When people think casual sex is just about people selfishly pursuing their own pleasure, I want to punch them in the face!

We spent more time together after that. It wasn’t just a casual thing. We were both open and honest about the fact that there was some intimacy there. However, I think this was largely due to the fact that, at this point in her life, she wasn’t a sexually casual person. She couldn’t just have casual sex: it needed to be a bit more for her. We were semi-dating. I suggested that this was probably a helpful rebound thing for her to get her past her ex, and I was very happy to do that. We both knew it couldn’t last. We weren’t going to be living in the same area for very long, and she didn’t think about sex in the same way I did.

The sex eventually progressed to her also performing oral on me, though I never came in her mouth. I generally finished with her giving me a handjob between her breasts with the help of durex lubricant. It was always amazing!

One weekend, I was away but we messeged each other a bit. It seemed that she was keen to keep talking and meet up again. However, when i got back from being away, I suggested meeting up on the monday, but she said she was busy. I asked about later in the week, but she said her parents were staying and then she was away on holiday, so didn’t think she could. Fair enough she probably couldn’t but I felt like she was brushing me off. I let it go for a bit, but then a few weeks later, I found myself thinking about her and wanting sex and company (in general). But i also wanted to spend time with her. I messaged her, she was in the area, she came over one evening, but then said she wasn’t up for anything physical. She had been on other dates. i was fine with that and expected her to. I had had other dates and hook-ups myself. I didn’t want anything serious. My suspicions were right: she had been trying to brush me off a few weeks ago. I was then hurt. It was unclear why she changed her mind. I guess she realised that there wasn’t going to be anything long-term, so didn’t want to continue engaging in sexual activity, which she found hard to divorce from intimacy/love. On her other dates, none had progressed beyond kissing. She just liked going out for the dates. Personally, I felt like she was wasting guys time. These guys, like me, may just want something casual and/or a relationship. But they don’t just want to go out on dates that are never going to lead anywhere. I think what hurt though was that, after we had spent a fair amount of time together, she didn’t have the decency to at least talk to me about ending things. We had talk about these matters before, so why couldn’t she do it again. I think I deserved more than just a ‘brush off’. I think it’s fine to do that when it’s just been a one-night thing or a date on which you felt no connection, but when you have spent at least the equivalent of a week with someone, talking loads, having lots of sex, being intimate, etc. I think you owe them more than a brush off.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, Making new friends

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? 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? Somewhat

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? How I could pleasure her so much.

What was the WORST thing about this hookup? How she just tried to ‘brush me off’ after spending the best part of two weeks together

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I haven’t changed how I think about casual sex, but it has reminded me about the important of sharing it with people that also have a casual attitude towards sex

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

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

Anything else you want to add about this hookup? Sadly I ended up not liking this person so much as I think she is not treating guys with proper respect

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 would like to see society recognizing the importance of casual sex

What do you think about the Casual Sex Project? Great. It’s been cathartic to off-load this experience

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