Enterprising mom story

Carriedaway22

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May 27, 2025
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Some of my stories are partially based on real life, but only for the underlying themes. This time, my idea revolves around a mother in her 50s in South Orange County. She has two daughters, one younger, one in her early 20s. There’s this boy who went to school with her older daughter. Back then, he wasn’t that good looking, not that cool… asked her daughter out, and she rejected him. Fast forward, and the mother is seeing this boy, now in his early 20s, picking up his younger brother who is her daughter’s age from school. This happens over and over, and they start talking and she realizes how cool this guy is now.. etc etc… he’s super successful… but he’s with someone (let’s say a model or someone just… seemingly 10/10). He breaks up with the model and mom hears about it… and slowly but surely she both tries to subtly get him with her daughter… and try to get her daughter to be hot to him… knowing that her daughter had fumbled him previously.

Good? Or nah?
 
I think there’s a lot of promise, especially depending on the mood or genre you’re going for. Personally I’m seeing a more comedic one where mom gets more and more desperate and tries to orchestrate more and more lustful encounters between them so daughter can get that bag…

Or all her efforts wind up with guy falling for mom instead
 
It certainly has something. The mom desiring her daughter to be with him is a stand in for her own desire of him, and she can live it through her daughter.

It can be incredibly versatile. I feel that a guy being successful is a cop-out, but he can be a stand in of her (ex) husband without the flaws. Friendly, enthusiastic, wants to travel, or whatever the mom wanted and couldn't with her husband. Maybe she chose a rich husband, and now realises she can make the right choice for her daughter.

Maybe she knows some of his other skills as well. One of his sexual encounters had been taped, and the contents leaked throughout the school to shame him. Mom obviously didn't seek out this contraband, but she did recognise it was futile to shame him. She saw his counterpart had as much fun as she rarely had before she got married.

Now she can live that through her daughter again. Even if she doesn't want to hear it, or know that her treasured daughter is in bed with a guy at all, she knows it'll happen. If it does happen, she wants to imagine her daughter getting the right treatment, both in the bed and outside it.

So she starts a secret crusade to make her daughter see him. Dreaming of the life she never had. The life she wishes for her younger self, while imagining herself in her daughter's stead.
 
I like it.
I'd have mom have an affair with him first. After a couple of meetings with him. She realizes this can't be a permanent thing and let's him down gently. But suggests he give her daughter another chance.
He meets the daughter and surprisingly they hit it off.
Daughter is happy and mom is happy until he walks up behind her in the kitchen one day and slides his hand into her pants.
"I can't be around you and not have you. I'm addicted to this mature body."
"What will you do if I say no?" She asks.
"I'm afraid I'll have to break up with her and find someone else," he replies.
Her shorts and panties are pulled down and she sighs as she feels his hardness slide into her from behind. "The things I do for my family," she thinks with a crazy smile.
 
I like the escalating hijinks with the mother trying to get him hooked up with her daughter. I would have it culminate in the daughter getting exasperated enough to come out of the closet and tell her mom that it's okay to date a younger man though.
 
Some of my stories are partially based on real life, but only for the underlying themes. This time, my idea revolves around a mother in her 50s in South Orange County. She has two daughters, one younger, one in her early 20s. There’s this boy who went to school with her older daughter. Back then, he wasn’t that good looking, not that cool… asked her daughter out, and she rejected him. Fast forward, and the mother is seeing this boy, now in his early 20s, picking up his younger brother who is her daughter’s age from school. This happens over and over, and they start talking and she realizes how cool this guy is now.. etc etc… he’s super successful… but he’s with someone (let’s say a model or someone just… seemingly 10/10). He breaks up with the model and mom hears about it… and slowly but surely she both tries to subtly get him with her daughter… and try to get her daughter to be hot to him… knowing that her daughter had fumbled him previously.

Good? Or nah?
I got a little lost in the multiple daughters.

You confused me right from the start. What's the significance of south Orange County? It's ambiguous and not very meaningful to much of your audience....
 
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