by Mcsteamy

Gender: Male
Age: 40
Race/ethnicity: Caucasian
Current location: Australia
Highest education received: Some college (not currently in college)
Relationship status: Defacto
Religious affiliation: None
How religious are you? A little
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Not active enough
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 0

Friend’s Mum

How long ago did this hookup happen? About 14 years 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? Attractive late 40’s lady. She was my mates mum. Knew her for about 4 years before it happened – I knew she had a thing for me I just never wanted anything from her. She had even previously invited me to her bed one night when no one was home but i declined being a bit in denial to what had just been asked.
Used to hang out with her and her 16 year old daughter really wanted a piece of the daughter even though I knew it would never happen.
Eventually stayed over one night had a few beers with the mum and it happened – I sorta knew it would earlier in the night just thought ‘why not’ as we both got more drunk.
Always had got on very well with her as friends the years before it happened.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Happened at her place no one was home as her daughter was slutting around. I was over for the night as I usually did – no real planning. Had some beers she instigated it she hinted we could stay in same room I thought ‘why not’. Should have declined like I had previously.

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? Started with awkward kissing then she proceeded to give me most boring blowjob I’ve experienced. She nearly vomited (she told me later she’d never done oral b4). I went to go down on her she declined said she was old fashioned. (Did go down on her another time weeks later & she loved it) Did missionary for a while maybe went onto doggy. Being young, inexperienced and eager I finished pretty early. By the time she had finished a smoke I was ready and went again. I think we went a third time.
I was happy to get some but also felt bad doing my friends mum and felt it was all wrong also. This didn’t stop us from a few more encounters later on (always going at least twice a night) but only for a couple more months b4 I stopped it.
She apologized once about it and we agreed to stop, only to go all over again b4 it finally stopped.

Did you have an orgasm? Did your partner(s)? I did but don’t think she ever did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? First time I insisted on a condom but didn’t end up using one. Never did after that. She was too old for pregnancy but I was young and stupid and thought she maybe could get preggas. She later told me her tubes were tied years b4.
No discussion on STI. I knew I was clean and assumed she didn’t get around much.

What were your REASONS for having this hookup? Horniness on my part. I think she was in love with me.

Were alcohol or drugs involved? If so, how much? Too much alcohol

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? I always felt bad and deceitful. She loved being the cougar even though she knew it would ruin the friendship.
After it stopped i still met up for a little bit but friendship wasn’t the same so eventually didn’t hang out anymore. Have no bad feeling towards her – haven’t seen her for around 14 years now.

To whom did you talk about the hookup? How did they react? Only told one random stranger one drunk night to get things off my chest a bit. His angry response: “why the hell are you telling me this for!!”
I think she may have told her sister who would have kept it secret.

Was this a consensual and/or wanted experience for you? For your partner? Consensual but not really wanted mentally for me.

Do you regret this hookup? If so, why? Yep. Felt wrong but couldn’t help myself. Friendship ruined not only with her but with daughter too. Fuck i really wanted a crack at the daughter she still makes me hard thinking about her.
I should say at this point that my mate (her son my age) wasn’t really a mate anymore before it happened he was a complete loser and still is.

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 sex was the best but also the worst. Best as I was young horny and inexperienced. Worst cause it also was amateur-ish.

All things considered, how POSITIVE was this experience? A little positive

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

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