My Mother’s Friend

by Chuck

What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Africa
What country and/or city do you live in? Pretoria, South Africa
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Scientist
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)? 2
How many hookup stories have you here posted before? 0

My Mother’s Friend

How long ago did this hookup happen? 12 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For more than 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 was my mother’s friend. I knew her when I was still a student and her children were still young. Now she was older, divorced, and building a new life. She was blonde with blue eyes, and a nice figure: a few years before she’d gotten buff in the gym, and it still showed, but she was softer now. She liked me: I could quote poetry and philosophize. I liked her: she was quite intelligent, and she has a different view on life, which I find interesting. To be honest, I found her quite sexy, and from her interest in my love life, I gathered that she was sexually interested in me too.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The ‘hookup’ unfolded over the course of weeks. We moved to the same city at approximately the same time. One evening I went to visit her, under the pretext of lending her a book. When she showed me her place she said “this is my bedroom. Sadly, I only use it for sleeping,” so I knew I was not on a fool’s errand. It was the first time we’d been alone together.

I visited regularly after that. Things progressed slowly – let’s just say I was innocent. While nothing ‘happened’, there was sexual tension. During one visit, I got a violent migraine. I took my usual medication for that, but I had to lie down and sleep. After some I time I woke up and felt better, but now it was past midnight. She suggested that I stay the night, and I agreed. I undressed to my underpants, and she wore her usual nightgown. We crawled into bed, spooning.

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? When we were comfortable, she took my hand it put it on her soft breast. I held her like that, feeling her nipple getting hard. Later, while she was lying on her stomach, I saw her beautiful bottom covered only by her long nightshirt, softly lit by an outside light, and I stroked it gently. Nothing else happened that night.

On subsequent visits I brought my pyjamas. I was still protecting my innocence, so I slept in my pyjamas with underpants, but by now we were french kissing and grinding. One morning before breakfast, while kissing and grinding, I had an orgasm, coming in my underpants.

The next time we were together, she took off her nightshirt and got on top of me while we kissed. I was still in my pyjamas and underpants, and I didn’t take them off, but a little bit later she touched my bottom, and I just couldn’t stand it any more and ripped off my pyjamas, showing her my raging, wet erection. She grabbed it and stroked it. She asked what I wanted to do. I said she should just keep doing what she’s doing. Within a minute or two I came, pumping a big load onto her hands and my stomach. She took my semen and rubbed it on her breasts. She cleand me up, we cuddled and fell asleep, naked.

By now she was starting to voice her frustration. I still wanted to maintain my innocence, but in a moment of honesty I had to admit that, first, my innocence was wearing rather thin, and secondly, that getting involved with her was all about sex, and not just about nice conversations. So the next time I went to visit, I took her to a nice dinner with a glass of wine, and took her home after. We went to bed, wearing pyjamas, but this time hers was satin. We kissed until we were both excited, then we got naked. She asked me what I wanted to do, and I said I wanted to learn what was happening here, and I put my hand on her pubis. She opened her legs, and took my hand and showed me where her clit was and where the opening to the vagina was. She was quite wet, and I got my finger wet and she showed me how to rub her clit. I rubbed it until she had an orgasm, and held her while she came down from it. Then she handed me a condom. It was a government issue one, so I declined it and got out my own, a Durex. She spread her legs and I got between them, I found her vagina and put my whole penis into it. I pumped away until I had an orgasm. Afterwards she cleaned me up, and we slept.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? After we had our first P-in-V sex, we hooked up one more time. I was looking forward to more, imagining a friends-with-benefits situation, but soon after that, she started dating a biker type guy, and I stopped seeing her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Sterilization, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection

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

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? I didn’t talk to anybody.

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? A little bit

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? It was a fun adventure, learning a lot about myself.

What was the WORST thing about this hookup? I wanted more, so I was disappointed when it stopped.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me feel more relaxed about it. If it’s safe, sex can be just fun. I learned the fun of flirting too.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? While were were busy shagging, all her focus was on giving me pleasure. I would have liked to feel more that she was deriving pleasure too.

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’d have casual sex more often if I could figure out how to get it. I don’t know how other people do it.

What do you think about the Casual Sex Project? I think it’s a useful store of stories, and a handy resource. It’s opened my eyes to how sexual people can be, while it’s almost invisible from the outside.

I’m worried that the Casual Sex Project has only positive stories, because people who have had negative experiences might not want to tell their stories.

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