Sissy Maids Stories

10,558 results
Orientation
Length
Source
Infinite Scroll

Rob and Cheri

by Just Plain Bob on Sep 17, 2017
Loving Wives

This story is like many others I have read on this site. It is unique only in that it happened to me. Looking back on it now I suppose I should have seen it coming, but I didn't. I can only blame it on being blinded by my love for Cheri. Well, the blinders are off now and I can't believe that I have been so stupid. I had been married to Cheri a little over...

Recovering

by RubenR on Sep 17, 2017
Mature

This is my contribution to the SUMMER LOVIN' STORY CONTEST 2016. It's the first time I've written under time pressure -- I hope it doesn't show too much... ************* It was kind of a relief. The feeling you get when your parents finally leave you at the beginning of the youth-camp. The moment you had been waiting for, nervous, but also excited -- free...

Somewhere In Between

by MistyMorgan on Sep 17, 2017
Loving Wives

My name is James and I have been married to my wife, Cali for twelve years. All of those years we were very happy and we enjoyed being with one another. We liked the same types of movies and had lots of friends with whom we socialized. We didn't enjoy the same sports, but that was all right too. She loved baseball; I was into football. We had parties with o...

A New Life

by JKBigDaddy on Sep 13, 2017
Transsexuals & Crossdressers

Bennie, age 21, lived on his own for the first time in his life. It was his first night in his new apartment. He had lived with his parents, Joanna and Chris Smart until just today. This was the start of a new life in many ways for him. Bennie, or Ben as most people called him, worked as a telecommunications tech for a local phone service. It was his first...

Matching Colors

by panther1282 on Sep 15, 2017
Transsexuals & Crossdressers

"So when did the girls say they were coming?" Raquel Martin asked taking a sip of her beer. "They said they would be here at six." Raven Smith answered also drinking from her beer. "And you told them where to meet us?" Amanda Dale asked. "Positive." Raven assured them both. "So what in the hell is taking them so long?" Raquel asked impatiently. "Dud...

Crossdressing at the Girls' Academy

by TiefBlau on Sep 19, 2017
Transsexuals & Crossdressers

How do I start the story of my transformation, from a young punk to a cock-hungry whore? I guess it begins with the summer of senior year of high school, a night I still look back to with shame. Those were dark times, when I was mostly a bundle of hormones and vanity. Still, I guess I need to start from the beginning. Looking back on the night, I never shou...

Dirty Dan Pt. 01

by R410a on Dec 17, 2018
Erotic Couplings

How does one come to possess the moniker Dirty Dan? Glad you asked. I grew up poor, not simply without, but dirt poor. My two sisters and I had little to nothing outside the very basics, all of our clothes were hand me downs, we had no indoor plumbing, we did have electricity and heated our small three room shack with wood. We would take a bath every Satur...

The Welcome Home Spanking

by RoseWilder on Dec 17, 2018
BDSM

Author's note: The protagonists of this story, Rebecca Eriksson-Garner and Sarah Garner-Eriksson, already featured in my stories "The 14th anniversary", "My beautiful sub(missive)" "Sarah acts out" and "Choosing Corner time", This is just another vignette about their life together and their love. A warning: The setting of my world may seem real enough and th...

Brittany's Travels Ch. 05

by YDB95 on Aug 26, 2019
Novels and Novellas

Brittany had long since accepted that her new life meant a lot more people would be seeing her naked than before she'd lost everything. She'd grown used to it in prison, and the perks of her new life were well worth it, but there were still times when it could be a shock to the system. Watching Angie stroll into the hot tub room in her bathrobe while Britt...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...