Sissy Maids Stories

10,558 results
Orientation
Length
Source
Infinite Scroll

Granddad - Party Time and Beyond

by WirdSmiff on Jun 4, 2019
Mature

It's Party Time! Girl's Nite To those of you that have not read the previous parts this will make much more sense if you start back at the beginning. Comments always welcum. ***** We were late, predictably. Despite being assured that she was probably less than half the age of any of the other attendees, Anja seemed to be obsessed with 'will I do?' and 'w...

Better as Riley Ch. 04

by cactusaur on Jul 16, 2019
Transgender & Crossdressers

Riley finally gets her sister Themes: Feminization, trap, anal, incest, promiscuity, free use, exhibitionism, creampie, lesbian, cheating ***** Riley woke hours later, curled under a thin blanket on bare mattress next to Kate and Becky, all three naked with cum oozing out of them. They were in a dimly lit room and she could hear the thump of the party...

Jaimie's Birthday Party

by jon.hayworth on Jul 13, 2020
Transgender & Crossdressers

JAIMIE'S BIRTHDAY PARTY (or Farewell James - Welcome Jaimie A She-Male cum slut is born) Jon Hayworth ©June 2020 With many thanks to my very patient editor NaughtyGeminiGirl96 the improvements to the original story are due to her, and any errors are where I have ignored her advice. * Birthdays when I was little were a problem, I was born on Christmas Ev...

A Most Unusual Girl Pt. 02

by R410a on Dec 24, 2019
Romance

The holiday cookies are baked and frosted, the candies are made and the Christmas decorations are up. It's time to submit part two. I wish you all a pleasant and joyous holiday season. All parties portrayed as having sex are 18 or older. ***** It was time to pick up Joann for our first date. I went to the garage where I kept my pride and joy housed, a 19...

The Business Trip

by OOAA on May 11, 2020
Fetish

My wife and I had been married for about 3 years when I first developed an interest in enforced male chastity. I had always had a very kinky and active fantasy life to fuel my almost daily masturbation habit. I was a 22-year-old virgin when I met Irene and I was looking to resolve that problem. Irene seemed like an exciting 20-year-old girl and I thought tha...

Power Over Men Ch. 04

by Aristotle_Writes on May 11, 2020
Sci-Fi & Fantasy

The man with the limbs that were too big for comfort climbed the tree with a speed too fast for comfort, and shouted words at me that did nothing to comfort. "Woman!" he shouted with those giant lips and, by the Goddess, with a huge, revolting, swollen tongue. "Need you! Will have you! Use you!" He shrieked, he laughed, he climbed that tree like some great...

Seven day Turn Around

by Red10Dog on Jul 6, 2020
Transgender & Crossdressers

Little about me, I just turn 30. I have had a few relationships in the past and dated a few beautiful women. Just broke up with my last girlfriend few weeks ago and that relationship was year and a half. I am 5'6 and weigh 140, so I am not a big guy and most women love taller guys. I found a classified that read "Male housekeeper needed at lake side cabin."...

Darcy's Doubts - Day 02

by Fenix89 on Oct 5, 2020
Transgender & Crossdressers

First off I'd like to thank everyone for their feedback! It's really encouraging to see so many people enjoying the story so far. The next "chapter" will take a little longer to write as it won't just take place over one day. We'll also get to spend some more time with Athena and Bibianna in the future. So stick with me till then, Thanks! Enjoy ----------...

The Nest is Empty!

by peyskip on Nov 16, 2020
Group Sex

Disclaimer-this is a work of fiction. Any resemblance of the characters to actual people is purely coincidental. Yes, group sex can lead to STD's and we should always practice safe sex, but this is fiction, not reality. This story includes group sex with male on male bisexual activity and wife sharing. If any of those things offend you, please keep looking f...

H is for Heuristic

by Robotman1974 on Sep 13, 2017
Sci-Fi & Fantasy

(Continuation of "The Mission") Chapter 01 - H is for Heather Byron Clarke looked at his watch. This new girl's punctuality and dedication were beyond impressive, they were amazing. For a moment, it flashed across his mind that she was overqualified, but he chose not to ponder on that notion. For the first time in over a year he had someone who could be fu...