Sissy Maid Father Stories

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Orientation
Length
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Infinite Scroll

Melody the Maid

by nohbdy88 on Sep 14, 2017
Transsexuals & Crossdressers

Melvin had been out of work for six months now. After being let go from his previous job, he had promised his wife Susan he'd find new work soon, but soon fell into lazily living off of Susan's income. At her request, Melvin had started helping out with the housework even more. One day, a package arrived in the mail for Susan. "Honey, I have a gift for you...

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

First Time Cuckold Ch. 05

by Angelscuck on Sep 14, 2017
Fetish

Oscar started sucking my well fucked pussy with great zeal, licking up all the cum that Jordi had deposited. Jordi's cock was so big and thick that it had left me quite sore and Oscar's attentions were both soothing and stimulating. After about an hour and four orgasms, I reached the conclusion that I really enjoyed being sucked to being fucked. Oscar looke...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Becoming a Sissy Cuckold Ch. 02

by Pantieslave on Mar 26, 2019
Fetish

Beth was now fucking Jerry every 2 or 3 days and each time they had sex Dan was required to be dressed in girly clothes and made to watch them as well as to video them. Beth loved watching the video's with Dan on those days that she didn't have sex with Jerry. Dan was also required to suck on Jerry's cock getting it hard so that he could fuck Beth and Dan wa...

Lock And Key

by ksu328 on Sep 1, 2017
Fetish

As the first snow of the season started to fall on my small hometown, my sex life started to make a turn just like the seasons. Well, I guess since I've never really had a sex life besides jacking off my little pee-pee, you could say that my sexual freedom was changing. The little box (ironic that it came in such a small box) arrived on a Wednesday and as m...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

A Sissy's Uniform Pt. 01

by Deeznuts4pm on Sep 14, 2020
Transgender & Crossdressers

I suppose the best place to start here is what my life currently looks like. I'm a 25 year old chastity sissy maid that lives with my dom. I would tell you my name before I was a sissy, but there's little point, so the name we are going by here is Jessica. I've always had a skinny build, and this is well complemented by my dark brown hair, which after servin...