Older woman, younger man story ideas

[CuMex1]

Story is based on my own personal experience with a really hot older woman, but I was looking to add a twist to it and need some story ideas. Feel free to PM me anytime for details or any questions.

 

[RoperTrace]

Story is based on my own personal experience with a really hot older woman, but I was looking to add a twist to it and need some story ideas. Feel free to PM me anytime for details or any questions.

You leave this so open-ended, it's difficult to know where to start. Do you want the older woman to assume a 'mommy' role? Are you talking about a ten-year gap, twenty, more? Did you know this woman before-hand? Was she a friend of the family? What about a neighbor that you fantasized about after reaching the legal age of course, and then circumstances put you together? A twist might be that she was your best-friend's mom, or what about your boss? I like the premise, but haven't attempted one in this category as of yet. I had that experience of an older neighbor, who dressed provocatively and visited my mother to chat when I was home from college during the summers. It seemed like the buttons on her blouse were often coming undone and her skimpy bras were always on display.

 

[sirhugs]

always mice to reverse the usual trope

 

[LupusDei]

Story is based on my own personal experience with a really hot older woman, but I was looking to add a twist to it and need some story ideas. Feel free to PM me anytime for details or any questions.

The thing I love for a twist is a triangle Older woman, younger man, young woman, where the older woman has a plan for each of the youngsters -- not necessarily to get them together, at least at first.

 

[FantasySharer1]

Hot mother-in-law is my favorite version of this. Ideally a mother in law who still wants to have just one more baby.

 

[gunhilltrain]

always mice to reverse the usual trope

They are fun to write. Usually the older woman has given up on her earlier pretensions. However, such relationships usually have an expiration date, usually when the guy finds someone his own age.

My favorite is about a young part-time limo driver who gets involved with one of his passengers (New York, 1970's). It started as a one-off, but eventually she (quite openly) gets two of her friends involved. It falls apart when he goes back to college and gets a new girlfriend. I left it open because one of the three (the last one he meets) decides to remain with him for a while anyway.

Anyway, a lot of kinky sex, first in the car (they pay to rent it and then ask for him to be the driver) and also in a ferry terminal in Lower Manhattan.

There is another one (one story only) about a divorced office worker (New Jersey, 1980's I think) who, in his frustration about his marriage and his long working hours, takes to masturbating in the office at odd hours when no one is there. He gets caught in the office of his older supervisor one night. Instead of firing him, she makes a play for him and he accepts, rights there in the room. Then he figures, "what the hell, might as well take her to dinner," which she accepts too. The story ends when they walk out together.

An on-the-job story event with the latter one.

 

[RoperTrace]

They are fun to write. Usually the older woman has given up on her earlier pretensions. However, such relationships usually have an expiration date, usually when the guy finds someone his own age.

My favorite is about a young part-time limo driver who gets involved with one of his passengers (New York, 1970's). It started as a one-off, but eventually she (quite openly) gets two of her friends involved. It falls apart when he goes back to college and gets a new girlfriend. I left it open because one of the three (the last one he meets) decides to remain with him for a while anyway.

Anyway, a lot of kinky sex, first in the car (they pay to rent it and then ask for him to be the driver) and also in a ferry terminal in Lower Manhattan.

There is another one (one story only) about a divorced office worker (New Jersey, 1980's I think) who, in his frustration about his marriage and his long working hours, takes to masturbating in the office at odd hours when no one is there. He gets caught in the office of his older supervisor one night. Instead of firing him, she makes a play for him and he accepts, rights there in the room. Then he figures, "what the hell, might as well take her to dinner," which she accepts too. The story ends when they walk out together.

An on-the-job story event with the latter one.

Sex on-the-job is the great American tradition. I've been in the position of working for several companies of various sizes, and there are stories at every single one about multiple liaisons occurring there.

 

[gunhilltrain]

Sex on-the-job is the great American tradition. I've been in the position of working for several companies of various sizes, and there are stories at every single one about multiple liaisons occurring there.

I've had a couple like those myself, although maybe they don't count because they were with my wife of the time. Well, she is my ex-wife now.

 

[Rob_Royale]

The thing I love for a twist is a triangle Older woman, younger man, young woman, where the older woman has a plan for each of the youngsters -- not necessarily to get them together, at least at first.

You might enjoy this one then. It features just such a triangle. Hope you like it.
https://literotica.com/s/milf-cruise-the-cougar

 

[Carnevil9]

The thing I love for a twist is a triangle Older woman, younger man, young woman, where the older woman has a plan for each of the youngsters -- not necessarily to get them together, at least at first.

That makes me think of The Graduate.

 

[LiverpoolMaster]

Teacher-pupil is an old favourite. Plenty of room for seduction either way... and the age difference thing can be ramped up to toe-curling extents.

 

[RoperTrace]

Teacher-pupil is an old favourite. Plenty of room for seduction either way... and the age difference thing can be ramped up to toe-curling extents.

I was still waiting for the OP to tell us what his def. of twist to the story might be.

 

[LiverpoolMaster]

I was still waiting for the OP to tell us what his def. of twist to the story might be.

The twist would anyway depend on the 'story so far', about which the OP gives zero details, so it beats me as to what he can expect from us. I was only offering up one venerable old version of young-old. Shrugs.