Sissy Maid Father Stories

79,895 results
Orientation
Length
Source
Infinite Scroll

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

The Session

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door open...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Steve's Maid

by Mixedwritings1993 on Sep 13, 2017
Fetish

Steve always had a thing for maids. He doesn't know what actually turns him on, their uniform or really the person inside the dress, but when there is a maid around; Steve can never keep his eyes away from her. Back at states when he was with his parents, he had an older lady as their house maid around her late thirties. Steve can't even count the number of...

Developing Emma Ch. 04

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

Emma took comfort in the shoes he'd bought her as the days passed, and as she slept she thought hard of the warm suitor's face and kissed her pillow; her anus tingling sweetly on the butt plug, imagining the beautiful sensation she'd experienced when he'd mastered her for the first time. She yearned for him and hoped he'd not just used her for a moment's ple...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Being a Sissy for Viv Ch. 04

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

With great care I slowly pulled the 10 denier black nylon stocking up my leg. I had other pairs, but these were my best and today it was important to have the best. Cautiously I rolled up the second one and with the same deliberation pulled it onto my other leg. The feeling, of soft nylon sliding over my naked skin exquisite and exciting as always, but today...

Proud To Be A Sissy Ch. 08

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how much my life had changed recently. After what seemed a lifet...

First Time Sissy Maid

by bart2077 on Sep 13, 2017
Transsexuals & Crossdressers

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, includ...

To the Manor Bound Ch. 04

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This probably won't make too much sense unless you've read the other chapters first. Like the other chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless, do comment and email me to let me know what you think, or just to say hello! ***** Chapter 4 - Five Weeks After Transformation Peter held the d...