Current location: UK
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Relationship status: Long-term relationship
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? 1 year ago
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling
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? He was several years younger than me. A big guy and not conventionally attractive, but very sweet with a great sense of humour. I met him through a friend. We spoke online and then the three of us went on a couple of nights out. He was a nice guy and if I’m honest I felt sorry for him. The only two sexual experiences he had had previously were drunken disasters.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been messaging a lot and decided to go out for a drink just the two of us. We had spoken about his previous experiences and I told him that I wanted to show him that better was possible. At the end of the night I dropped him off outside his house and we kissed.
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? After the first night we met maybe half a dozen times. He made me laugh and made me feel really good about myself. The first time he made me orgasm just from playing with my nipples. Other times he would make me cum with his fingers over and over again. He was completely focused on my pleasure. A couple of times we attempted to have sex, but it was awkward as the only space we had was the back seat of the car, and it didn’t work so we quickly gave up. We had talked about booking a hotel room but it didn’t happen.
Did you have an orgasm? Did your partner(s)? He made me orgasm multiple times. He is the first person that did that, and only one person has since. I couldn’t make him cum with my hand or my mouth, which knocked my confidence a lot so he would play with himself until he got close and then cum in my mouth.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? The twice we attempted sex we used a condom.
What were your REASONS for having this hookup? I liked him and I wanted him to have a good sexual experience. He made me feel sexy.
Were alcohol or drugs involved? If so, how much? No
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? After about six weeks he gradually stopped talking to me. There was never an expectation on my side that it would be anything more than a fling. I was sad about the way it ended, but I should never have got involved with some one so much younger and immature.
To whom did you talk about the hookup? How did they react? I didn’t tell anyone in ‘real life’, but a few people I have met online since then.
Was this a consensual and/or wanted experience for you? For your partner? It was consensual, and wanted.
Do you regret this hookup? If so, why? Yes and no. Sometimes I worry that I took advantage of him, and I regret the way it ended.
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 worst thing is the way it ended. The hook-up changed me in a big way. I would never have dreamt of cheating before – I thought I was happy with my sex life. My experience with him showed me how much more exciting and sexy sex (in all forms), can be. I always had a very sheltered view of sex before. He opened my eyes to the possibilities when you start looking beyond what society views as acceptable and normal. More than anything he made me feel good about myself; he made me feel like I was worth all of the attention he was giving me.
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 don’t feel the guilt from cheating that I always thought I would – and I think that tells me more about the state of my relationship than I would like to admit.
I have since hooked-up with other people, although it’s never got as far as penetrative sex. I don’t know whether it’s because my morals only stretch so far, or because I worry how it will affect me emotionally.
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