This a very simple theme and plot and I have a story in mind around it, but I'm also open to hearing your thoughts and your wants towards such a pairing. Read onwards.
The married MILF, her son's best friend, he takes advantage of a rift in her marriage, then blackmails her into keeping the relationship going. She's drunk one night, she and her husband have been arguing, the son's best friend in staying over (he's 16-18) he stumbles on her drunk in the kitchen. She's wearing some sexy lingerie, a sheer little lacy teddy, garter belt, stockings, high heels, she was supposed to be celebrating with her husband, having sex but he got called back to work and off he went, they argued, she's left feeling neglected, unattractive, vulnerable.
And standing infront of her is this handsome young stud staring at her with big, blue eyes that are hungry with lust when he stumbles upon her drinking alone in the kitchen. Things get heated, they flirt, it's playful at first, she's tipsy, she's drunk, he makes her feel good, sexy, like a woman again. And then things get out of hand, he's kissing, groping, licking and she is whimpering lustfully, it feels good but it's so wrong and she can't seem to stop him.
Adding a couple more ideas here just to show possible ways this sort of paring could play out and hopefully garner some interest.
The Film Project
I want to start out by saying that I left this plot under the incest setting because I see it as a mother/son or an aunt/nephew pairing but it could just as easily be played in the same vain as To Tame a Housewife further down between a younger male 18-20 and the mother of his best friend, can we say MILF? Fun stuff.
This is another incest based plot, however, it could be done in the same vein as To Tame a Housewife between a younger male and one of his friends mother's. Also the age difference here does not have to be extreme either, as long as it realistic. The general idea here is between a mother/son or an aunt/nephew. The young male in this story, lets call him Jack is recently returned home from his first year away at Film School where he is studying to be a director. Now, he's always had an attraction to the female lead character in this story (whether it is his mother/aunt/best friend's mother or what have you) that he has always had to keep hidden and secret. During his stay away from home at school, he's experimented and has found that nothing is able to quell the secret attraction he has for the female leading character. So while he is away he comes up with a plot that he decides to enact when he returns home for his first break.
He goes to his mother/aunt/best friend's mother or what have you and then confides that he is close to failing his first semester of film school and flunking out of the course. He pleads with her, knowing that when she was younger she wanted to be an actress, and knowing that she would do nearly anything to help him out. He pleads with her for help, telling her that he has to complete a film project in the one week he has at home. The film project will have to be a love scene and that he doesn't know anyone else who can help him out. She agrees, reluctantly, but willing to do this to help keep him from failing provided that everything remains professional. The story would progress from there, I imagine, with the scene ending up going much further than she had planned and then the two have to deal with this new wrinkle in their relationship.
It could proceed from here as a blackmail story, or a romance, or really whatever we want and involve anything from impregnation to whatever other sort of drama and kinks we can come up with together to toss at the story.
Non/con, Blackmail, Coercion, Manipulation, Forced Seduction, Kidnapping, Possible risk of Pregnancy in one Plot are elements you'll find here
This plot is a bit different that most of mine but it still contains a popular theme and pairing for me. It is a mother and one of her son's friends, I imagine it anywhere from 16 to 20ish for the age of the son's best friend. The general idea here is that she is recently divorced and feeling down about herself, wondering if she is still attractive and very vulnerable. She's always been the cool of sort of parent, buying alcohol for her son and his friends and letting them party at her large house provided they all stay and no-one leaves to go driving drunk. So one weekend after the divorce, she is feeling lonely, vulnerable and unsure of her looks so at one of her son's parties she gets very drunk. Drunk flirting with her son's best friend leaves her feeling attractive, alive, desirable again and one thing leads to another and the two end up sleeping together. Afterwards she is remorseful, she regrets it, she wants to end it right there. I imagine this proceeding with the son's best friend being the aggressive sort, he's always liked her and this night between them was amazing. He knows that she likes it, that she likes him, but the age difference, the taboo of the relationship is holding her back.
I imagine her as very conflicted about all of this, it feels so good, but it is so wrong in her mind. It could proceed as a romance, or something darker. It's all up to you. Let me know what you think. Let me know what you think, this could go a thousand different ways, so bring on the Cougars and the MILFS!