Submissive Milf Stories

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"Stocking Tales": Office Submission

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Sexy submissive MILF does WHATEVER it takes to get the job. Note 1: A great thank you goes to Vanessa for modeling for the photos (I pray I am as beautiful as you in ten years). Note 2: Another great thanks to the photographer Richard who took the pictures and created the ambience. Note 3: Thanks to Mab7991 for his editing this story and LaRa...

Naughty MILF Caroline Pt. 01

by scooter111 on Dec 9, 2019
Humor & Satire

These stories are about Caroline, a stuck up, nasty, uppity MILF businesswoman who acts all prim and proper on the outside, but is a nasty cheating bitch underneath. She has a thing for young studs and gets a damp tingling pussy thinking of the lads working in the company next door to her Business where she works as a Company Director. She is not well liked,...

MILF Lives Her Fantasy

by MilfMaid on Sep 14, 2017
Exhibitionist & Voyeur

As a teenage exhibitionist I had a diary where I could write all the dirty little things I did that I could not even tell my best friend. That was never very satisfying because I wasn't really sharing anything with anybody. But it was all I had. Since my teen years, however, I haven't needed a diary because I haven't had any dirty secrets to worry about. In...

The Futa Milfs of Total Drama

by Floresfire on Apr 22, 2025

Currently, we have seen how and what the Total Drama competitors are like throughout each season, even during the Ridonculous race. But we never wonder how they became who they are... and the easiest question is... their mothers. Yes, the mothers of the Total Drama competitors and Ridonculous racers who in this reality are actually hot and sexy chubby MILFS,...

Summer of Slut: MILF Challenge

by silkstockingslover on Sep 26, 2017
Illustrated

"Summer of Slut": MILF Challenge SUMMARY: 4 MILF's decide to see who is the biggest slut over July long weekend. CREDIT & THANKS: A super special thanks to legendary artist Rebecca (of the Housewives at Play series and many more) for giving me permission to use a few of her plethora of illustrations for this story. We collaborated in 2014 on Straight H...

Cheerleader's Mom: Mom's Lap-a-Thon

by silkstockingslover on Nov 25, 2019
Illustrated

Summary: Submissive Mom has five visits in marathon fuckfest. Note 1: Thanks to hfernandez1983 for doing the visuals for this story. Note 2: Thanks to Tenzin, Robert and Wayne for editing. Recap: In Part One, A POWER SHIFT: 39-year-old mother Michelle decides to try on her daughter Allie's slutty cheerleading outfit. Once she has it on, she begins fuckin...

A Summer of Tight Fits Pt. 05

by Ralle99 on Sep 24, 2019
Group Sex

"The Final Chapter (sort of)" By Ralle (All persons engaged in sexual activity in this story are over 18 years old. Any similarities between this story and real people are purely coincidental) Please read Pt. 1-4 first to get caught up. ***** Karen awoke to the sound of lawnmowers next door, a jarring start to the day. She stumbled out of bed and made h...

SlaveX: Utter Submission

by Comoros7 on Sep 25, 2017
BDSM

1) This is fantasy. These things don't happen in real life... often. 2) This is in the 'BDSM' story category but it could certainly be classified as 'Love/Romance', especially the latter half. 3) The story contains strong elements of: BDSM; humiliation; reluctance; straight and lesbian sex; pain; and pet-play. 4) Rather long with no chapters, sorry. 5) I...

For the Weekend Ch. 05

by missuscooper on Sep 13, 2017
BDSM

We sleep well into the next morning. Tim keeps me close to him throughout the night, his body wrapped around mine. I wake and go to use the bathroom. Tim comes in as I am finishing, then rejoins me in bed when he is done. He cuddles me for a moment, then rolls on his back. "Time to start our day," he says. "In the truck last night you said you'd swallow my...

My Friend's 43y/O Kinky Mother

by ArthurG77 on Sep 11, 2017
Mature

This is my first ever story. Thus, I am no professional at this. However I intend to write a hot story as good as the best. Unlike the majority of stories on here however, this one is actually true and happened to me when I was 19 years old in the 1990's - enjoy My name is Arthur and my best mate back then was Mike. We met in the early years of high schoo...