Milf Sissy Stories

11,621 results
Orientation
Length
Source
Infinite Scroll

I Make Believe I'm a Cuckold

by donaldelliott11 on Jan 20, 2020
Fetish

[Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either one. The story carries the label "BCS". In other words, if I put it in the Loving Wives section, it would be lambasted as Bi Cuck Shit. Tough crowd over there.] +++++++++++++++++ Every few weeks I travel with a female coworker to three-da...

Housewife Becomes Sex Slave

by RottenPines on Mar 9, 2020
Mature

In this collaborative script, a young man seduces a married woman, convincing her to run away with him and become his sex slave. —— Start —— Man: Geez, I wish my parents would get off my back about getting a job. I just got out of college. Can't a guy have a little fun? Hell, if I really need money, I can do what I did back at school, find some horny old...

Hotwife Iris Goes to Party w/Jack

by Aynsley on Sep 26, 2017
Loving Wives

"Are you sure you're okay with this?," queried my beautiful 45yo wife. "Heck, yes," I said. "I am a little nervous…but in a good way. I think this is kind of exciting. I'm surprised YOU are not more nervous." "Oh, I am. But Jack is such a darling. And I think it's so cute that he wants to show me off to his friends," said Iris, as she continued to...

HotWife Iris has Date with Young Jack

by Aynsley on Sep 26, 2017
Loving Wives

"You seem nervous," I said, as I watched my voluptuous wife, Iris, fidget in the passenger seat of our car. She kept adjusting her low-cut, black silk blouse, to maximize the cleavage she'd be showing to our young, soon-to-be friend. "Well, of course I'm nervous," Iris shot back with a grin. "I haven't gone on a date, since I started dating you, and now I'm...

My MILF Story

by IllinoisMILF on Sep 17, 2017
Loving Wives

I'm one lucky man that has a short story to relate for all too understand that there are MILFs out there that not only take care of their man, but also there own libidos in addition to taking other men and select women for there wildest sexual rides. One story at a time, so this one is when we were in San Diego. My wild MILF and my SIL wanted to go out, but...

My MILF

by IllinoisMILF on Sep 17, 2017
Exhibitionist & Voyeur

I'm one lucky man that has a short story to relate for all too understand that there are MILFs out there that not only take care of their man, but also there own libidos in addition to taking other men and select women for there wildest sexual rides. One story at a time, so this one is when we were in San Diego. My wild MILF and my SIL wanted to go out, but...

Milf Waifu

by Ashton210 on Dec 28, 2020
Fan Fiction

All characters are at less 18 years old unless the story says so. The Male has aMilf fetish fucking milfs and getting females pregnant too. The milf as a child that you are friends with, and if the milf has a man in the show, movie, book, or comic/manga she will not have him here, the man would ether be dead or they split sometime in the past. My name is (F...

Open in Reader

On the Beach Ch. 03

by Turbidus on Sep 25, 2017
Exhibitionist & Voyeur

The fallout from the previous night's festivities continues... Thanks to LarryInSeattle for his editing. Any errors that remain are my own. ***** I gave up on the idea of jerking off. Something was going on with Bill. I realized that this was the first time in my life I was worried about my brother. He'd never gotten in trouble. He had been about the l...

Easy Women on Easyjet

by johnthepostman on Sep 2, 2017
Erotic Couplings

I'm not a big fan of air travel but last week I experienced something a bit different and thought I would share it with you. Flying Easyjet is sort of OK. You get what you pay for. Delays are the norm and the scramble to get on the plane brings out the worst in everyone. I arrived at my departure gate with a little time to spare and noticed the Easyjet staf...

Another Evening with Mr. Logan Ch. 02

by TheSparkZone on Sep 18, 2017
Exhibitionist & Voyeur

I went into my room, but before I got dressed I heard Mr. Logan and my mom heading for her bedroom. I peeked around the corner and noticed that they didn't close the door all the way. Figuring that this could be a golden opportunity to get the goods on Mr. Logan, I grabbed my super high definition video camera and tip-toed down the hallway. There was a six-i...