Milf Sissy Stories

11,621 results
Orientation
Length
Source
Infinite Scroll

Theo's BDSM Slave Service

by MasterBlogman on Jul 9, 2019
BDSM

Author's Note: I have added this preamble to make sure that readers know what they're getting when they read this story. The first version drew a few nasty comments from readers who were grossed out by the graphic and occasionally brutal non-consensual content. (Why anyone who is easily grossed out would read past the first couple of paragraphs is a mystery...

Cougar House Ch. 03: Wet Dream

by SZENSEI on Jun 12, 2019
Exhibitionist & Voyeur

"My first ever real party." Elliot Needy was stoked. It wasn't so much a surprise party yet many surprises were in store for Margo Needy's future world traveler. His close friends Brian, Cabot, Eric, and Heath had gone to great lengths to make it memorable. Mostly for them. They had been somewhat playing the young Prodigy over the last year in order to inf...

Fun with Photos Ch. 13

by yarnspinnerr on Nov 12, 2019
Group Sex

I recommend reading the previous chapters first. All characters are fictional . Hope you enjoy ;-> *** Todd sprawled in the rocking chair in his bedroom, looking in disbelief at his wife and her best friend Beth. They had just worked together to get his pants off his ankles after he was seated. Once his pants and socks were cast aside they sat back and...

Past Her Prime Ch. 02

by SamTaylor on May 22, 2019
Mature

Any and all persons engaging in sexual activities are over the age of 18. ***** 'Hi. My name is Sam and I am an addict' 'Louder,' said a voice from somewhere. He cleared his throat and enunciated more. 'Hi. My name is Sam and I am an addict.' 'Harder baby harder!' On hearing these words, Sam was rudely shaken out of his day-dream and it finally dawned...

Motherly Grudge

by ScumDumpster69 on May 21, 2019
Transgender & Crossdressers

"... Do I have to be here?" Cole asked anxiously. His mother was turned away from him, busy with taking out several trays of lasagna out of the oven. "I can stay at a friend's house or something..." Christina, as his mother was named, sighed heavily. "It's only for one night, Cole. I know what she's like, but you can't just avoid her." After setting the las...

How Much Do Manila Prostitutes Earn

by JimGrinsted on Jun 19, 2019
Reviews & Essays

The good news is my wife is from the Philippines. The bad news is my wife is from the Philippines. Because, in addition to my wife, I LOVE prostitutes. Just read my other stories on this site--they're all about hookers one way or another. Despite (in my opinion) that the best place for prostitution in the whole wide world is the Philippines, because of my w...

Watching Cyn (or was it Sin)

by CiaoSteve on Jul 14, 2020
Exhibitionist & Voyeur

Copyright © June 2020 by CiaoSteve CiaoSteve reserves the right to be identified as the author of this work. This story cannot be published, as a whole or in part, without the express agreement of the author, other than the use of brief extracts as part of a story review. This is a work of fiction. The events described here are imaginary; the settings and...

The Group Ch. 02: Steve Impresses the Members

by DarkDeliciousDebauchery on Nov 4, 2019
Group Sex

This is the second part of the series titled "The Group." After being persuaded by Eileen, Eve, and Susan to let their Group use his Loft, Steve gets to meet the rest of the Group's Members. Feedback from readers will help me decide which direction to go with the story in the future, as well as which characters to develop. Thanks for your input. ***** "...

Queen of Me

by Defluer on Jun 1, 2020
Interracial Love

From the author: This story was spawned in my head as I went to Story Search and saw the Recent Searches list. My eyes scanned through them and by number 3 I had a story idea, then I decided it would be fun to include them all. I actually had to Google what number 10 was. The list was as follows: 1: best friend mom 2: big breast 3: black mommy 4: creampie...

Neighbor Girl, Tracy Ch. 03

by nochoiceleft on Apr 1, 2020
Anal

"'Show me?' Did she just say 'Show me?' while bent over a desk taking a whipping?" What is it about this woman? Is it that she Tracy's mom? Is it the trepidation of getting found out? Or is it that she wants to end up just like her eighteen-year-old daughter with red stripes crisscrossing her ass and the shit fucked out of her? Well, that's what I did. I s...