Milf Sissy Stories

11,621 results
Orientation
Length
Source
Infinite Scroll

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Sissy for Mommy's Nipple Cream Ch. 04

by ppeaks42 on Feb 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jaime clasped a hand over her mouth in horror, but it was too late and she knew it. Chills ran down her spine as Julia sauntered over with a wicked smile, then opened the door to reveal her sissy daughter sitting there wearing nothing but her lacy panties and her steel clitty cage...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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Growth-XX

by FlatCap90210 on May 20, 2019
Science Fiction

James felt as if he was going insane. It was summer, the sun was shining and he was at the beach ogling girls. Tits of all shapes and sizes surrounded him, wrapped in bikini tops, one pieces and other pieces of fabric of varying coverage. James' heartbeat pounded in his ears and throbbed in his crotch, digging a furrow in the sand beneath him. He was lying o...

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Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Runt of the Litter

by grimbous on Oct 9, 2017
Transsexual

(This story involves a lot of humiliation of the main character, futa on male action, incest, and other fringe fetishes. If these aren't your thing turn back now. I also wanted to give credit and thanks to the artist Mafen for the above picture which helped inspire this story.) The hall is quiet. You were pretty sure nobody was at home. You creep carefully d...

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The New Girls

by phoenixcinders on Jan 7, 2020
Transgender & Crossdressers

Hey everyone! Here's another story. This story runs alongside with a few other stories, including Neighbors, and several stories I am currently working on. Of course, all characters involved in sex are over the age of consent which is 18 in the USA. I hope you enjoy, let me know what you think in the comment section. Feel free to reach out to me to discuss i...

Everybody Needs a Hobby Ch. 08

by GeorgeDaBuilder on Sep 25, 2017
Erotic Couplings

It's been a busy week for Britt and I and Red Brick Photography. RBP was born after I received a call from a graphics firm who was going to be doing a calendar for a local auto body shop. They were going to gather up 13 different hot rods and muscle cars and I was going to provide a comely model or two to pose with each car and take the pictures. I agreed t...

X-Change: The Frat House Blues

by MrYowman on Sep 16, 2017
Sci-Fi & Fantasy

The world had been changing rapidly. Maybe for the better, maybe for the worse, that was yet to be determined. But the progressive political movement of the early twenty-first century had definitely made grounds, if not economically, at least socially, especially where sexual and gender norms were concerned. Science too, had made this new world more bold and...