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Friday, March 1, 2024


A girl I really liked wouldn’t give me the time of day back in school because I wasn’t fun enough, recently I hooked up with an older woman and turns out its the girls mom.


So I (35M) recently found out that the older woman I am freely having sex with (52F) is the mom of a girl i used to want to date in college.

Back in school (2009-2014) I was a decent looking guy but was always busy because of work and going to school. my part time job just hired a new cashier that I was head -over-heels for.

After awhile of just going through her counter like and being cordial/friendly with each other I managed to find my balls and ask for her number and she at first was shy about it but then she said yes!

And damn i was ecstatic because she was drop-dead gorgeous and even though I was always busy though i still managed to find time here and there to text her and see what she’s doing etc and she would always reply but when i finally asked if she wanted to hang out she started becoming distant to the point where she stopped responding to my texts.


I would run into her at parties and i would say hi and stuff but i never had the guts to see where i went wrong until one day I messaged her through facebook (back in the day) and asked her point blank if id ever had a shot.

She said “No, you will never have a chance with me, you aren’t my type, you seem like a nice guy but honestly you seem pretty boring”.

I left it at that and even though id still see her at the store i deleted her number because well, whats the point?

Flash forward to February of this year. Graduated awhile ago, have my degree, have a house, older car but pretty independent. More confident, bolder. Got a relatively stable job whose CEO wanted to start bringing everyone back in the office at least twice a week so that we know the faces of the coworkers we email and also for meetings. Fine. Whatever.

HR had just hired a fresh batch of people for the company, ranging from landscape/maintainance personnel to managers/adminstrators.


I grew up poor and so I always learned to say hi to the gardeners and janitors and introduced myself to this older woman, who i admit caught my eye because she had an AMAZING body ,and i mean like slim waist, massive jugs.

She had a mommy makeover and it looked GOOD. She was older than me, but because of my personality we got along really well to where we would joke with each other and ask why we weren’t married.

Turns out she was divorced and didn’t want anything serious to which i responded by asking for her number. She actually texts me one night after i get off work and without hesitating i ask her to meet up for some coffee (because im old af now) and before she gets a change to get out of her car i jump in the passenger seat just to see what my limits are.

After having an intimate conversation she receives a text message and says thats her daughter is asking her to open the door to her house so she has to go, i don’t want her to go and rush to kiss her.

Idk how it happened but somehow we ended up in the back seat of her car and one of her pant legs is off and im pulling down her underwear while unzipping my pants.

Honestly don’t know what got into me but we did it right there without a condom, i finished inside her and it was amazing.

I text her the next morning asking if she was alright and if she regretted what we did to which she replied with no.

After that we would meet up in hotels or cars to bang pretty regularly, she said she couldn’t form a relationship with me because i was almost as young as her daughter and tbh I didn’t think anything of it until last week, when i was in her bedroom for the first time, she did amazing things to me that ill never forget.

When we were done she turned on the lights to her living room in order to walk me out when i spot a family portrait of her, her two sons and the girl who rejected me back in the day.

I asked her who that girl was and she said it was her daughter. I tried to play it off and began ask her what she does and etc, and she told me that wished she would marry a decent guy like me.


I was in awe at the luck I had struck and am not sure if i should continue this arrangement or if i should cut my losses because eventually i will run into the daughter at the moms house and it will be a shit show.

Anyway i finally got this off my chest! No one knows because she asked me not to tell anyone that she lets me satisfy her but i just felt the need to tell strangers. thanks!

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