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What’s your gender? Man
How old are you? 58
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: College degree (eg., BA, BS)
What’s your occupation? Finance
What’s your current relationship status? Engaged/Married (monogamous)
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)? 250
How many hookup stories have you here posted before? None

Daughter’s Friend

How long ago did this hookup happen? 5 years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

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 (M) was 21. A pretty girl, who smiled a lot, but rather overweight. She was my daughter’s friend, a year above her at school. I actually probably first knew her as a baby/toddler, although I don’t really remember, as her family were then neighbours, and her mother was friendly with my wife. I got to know her a bit over 2 – 3 years before we hooked up. Daughter and most of her friends were at various unis, but M was a home. I used to see her sometimes, and always flirted with her a bit.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Our work circumstances meant that we started to see each other rather more often, and I sensed her interest, which surprised me as I was 53 and she 21. We became gradually became closer and closer, and one day kissed briefly. From there I took every opportunity to touch her, which she seemed to enjoy. We met secretly, but she always resisted having sex. Then we were together, alone, standing kissing in a secluded place, I unclasped her jeans and slipped my hand into her panties, fingering her. I pulled her panties down, and took out my cock. I rubbed it against her pussy lips, and we were close to fucking, but she stopped and said, “No, I can’t”. She later texted to explain that she didn’t want her “first time to be like that” – until that message I hadn’t realised that she was a virgin.

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? We arranged to meet at her house one morning after her mother had gone to work. She didn’t want to use her bed in case it was messy, so had put down towels on the lounge floor.
When I arrived she stripped naked, so I did the same. She lay on the floor, and I put on a condom. She opened her legs, and I climbed on top. It was difficult to enter her, as she was so tight, so I moved down and licked her unshaven pussy to warm her up. I did this 2 or 3 times.
Eventually I penetrated her. After easing my cock into her, we began to fuck gently. After a while I lifted her legs to make it easier to get further in, and I was then able to increase the pace, but she soon found this uncomfortable, so I stopped, and pulled out.
Not surprisingly, the condom was covered in blood, and this made me a little uncomfortable too, so we decided to stop, and dressed.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

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? She later texted me to say that although she had enjoyed the experience, she didn’t feel ready to do it again. We haven’t hooked up since,
We kept in touch, and some months later she found a boyfriend much closer to her in age.

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), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, It was easy / convenient

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? 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? I told one male work colleague, who seemed impressed and quite jealous in view of her age.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

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? Being wanted sexually by such a young girl. The thrill of fucking a friend of my daughter’s. Taking a girl’s virginity for the first time since I was 15 years old.

What was the WORST thing about this hookup? I wish I had given her more consideration emotionally – it was very much a physical event, and I wish we had taken time to kiss and cuddle rather than get straight down to it. I also wish we could have both cum.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I would do the same again in similar circumstances.

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

All things considered, how NEGATIVE was this experience? A little negative

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 enjoy it, but as a married man I wish I was able to be more open about it.

What do you think about the Casual Sex Project? Fantastic. I enjoy reading the stories, and have been rather aroused by some!

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