Mum’s Friend



What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? United Kingdom
Highest education received: High school diploma
What’s your occupation? Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
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)? 50
How many hookup stories have you here posted before? 0

Mum’s Friend

How long ago did this hookup happen? 22 years

How would you best classify this hookup? One-night stand

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 was mid forties, I knew her well as she was one of my Mum’s best friends and lived in my street.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Her husband had a lot of problems, looking back he must have been depressed and her and her kids would very often hang out at ours in the evening. One night, I remember being woken up by hysterical crying. The husband had attempted suicide and was rushed into hospital. Her kids stayed at ours for a couple of nights. On the third night, she stayed over because she didn’t want to go home. I gave up my bed for her.

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? I gave up my bed and slept on the couch. During the night, I woke up with a fright and Jackie was sat on the chair next to the couch. She had a drink of water and had been sat there a bit apparently. We started talking, I had never really chatted to her before. During the course of the chat she ended up say on the floor in front of the couch. I told her I was sorry that Jack (her husband) was a mess and she started crying. I didn’t know what to do but I stroked her hair and she cried into my hand and kissed it. She looked at me and all of a sudden, I was massively turned on. She moved the duvet back and looked at my PJ bottoms. She asked if her kissing me had turned me on and I didn’t answer. She asked if I’d been kissed before and I told her no, I’d never done anything before. At that point she took my PJ bottoms down and wanked me off. I lasted about 8 seconds and nearly passed out when I came, it was my first orgasm. She was stroking my hair as I recovered. She then climbed on top of me, I was still covered in my own cum, and put me inside of her. This time I lasted about 22 seconds and then came again and again nearly passed out. She got off me, got some tissues and cleaned me up. She tucked me in and went back upstairs. I was so turned on I wanked myself off. I learned how to masturbate that night.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

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? I didn’t know what to do the next day. We were all having breakfast, Jackie didn’t seemed dazed by it and there was no hidden looks, knowing winks etc. Things just carried on. Jack died a few years later from a heart attack and she moved somewhere with the kids. I saw her a few years later in a shop I was working in and She asked if I’d enjoyed ‘our special night’ I told her yes and she smiled. Nothing more was said.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Learning new things, experimenting

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My mates – they thought I was a legend.

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

Did you get emotionally hurt as a result of this hookup? Not at all

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? I lost my virginity to a great looking MILF and the feeling of that first orgasm has never been replicated.

What was the WORST thing about this hookup? I didn’t last longer.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? For years I only pursued older women.

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? Years later, her daughter served me in Supermarket and I took her out for a drink. We kissed a little at the end of the night but nothing progressed beyond that.

What do you think about the Casual Sex Project? Love it.

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