Castrated Sissy Maid Stories

20,513 results
Orientation
Length
Source
Infinite Scroll

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Appointment by Card Only Ch. 02

by Sputnik57 on Sep 17, 2017
BDSM

Madam Ruth was more than pleased with her days work as she descended to the bed and stroked the soft white body of the helpless sissy, Poppy mustering a whimper as the dominant Madam. Cupped the soft pink scrotum and gently worked the dainty cock to an erection; she was scared but the surreal situation along with the gentle warmth of the two females, combine...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

A Sissy Maid's Tale Ch. 01

by Erotictales4u on Sep 19, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy in the femdom niche, it is focused on male submissive humiliation and has a Sissy theme running through it. Is set in an imaginary future. ***** The cool air licking at my almost bare ass cheeks enhanced the feeling of nakedness, but I wasn't naked. In fact, it would have been...

Being a Sissy for Viv Ch. 06

by Caron on Oct 31, 2017
Transsexuals & Crossdressers

Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...

My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

Fantasy Weekend

by DWornock on Sep 24, 2019
BDSM

MF, MM, MMF, FMF, Fetishes: sexual role-playing, cross-dressing, domination and submission, and pain. The youngest person in this story is a 19 year old receptionist. 4Play has given me permission to make modifications and additions to his story "Date Night." I changed the title to "Fantasy Weekend." I also added the first paragraph to chapter 1, deleted...

No Choice

by AZgirlMichelle on Sep 16, 2017
Transsexuals & Crossdressers

You act as if this is news to you. I'm surprised that you would even question the fact. This isn't a bedroom game. It never was. I have a plan and you WILL follow it. Choice? What choice? Whatever gave you the idea you had a choice? I told you that things would change if you wanted to live with me. I told you it was my way or the highway. And what did you s...