Chastity Feminized Stories

7,367 results
Orientation
Length
Source
Infinite Scroll

The Roommate Ch. 01

by rebeldoll on Sep 25, 2017
Transsexuals & Crossdressers

Chapter One: Change comes when you least expect it. When it comes, it comes full force, and then your life is altered before you realize what has happened. About a year ago, I was being evicted from my apartment and was in fear of losing my job. I could no longer afford where I was living and needed to move fast. I did what most people do; I began searching...

My Father, The Maid Ch. 03

by SissyOona on Dec 12, 2018
Transgender & Crossdressers

A Case Of The Mondays By Sissy Oona. Sleep came easy that night, I was frankly a bit worn out from the amazing sex we'd had. I was awoken by the door to the room opening and the click of heels on the wood floor. I cleared my weary eyes to see my father entering the room carrying the breakfast tray I had become accustomed to seeing in the morning. Noticing...

Chaste (A One Week Chronicles Story) Pt. 02

by Louise69 on Oct 14, 2017
Transsexuals & Crossdressers

Dear Reader, thank you for clicking on this story and reading it. I hope that you enjoy it, but know that it will be my most divisive story! Hopefully, by the end, you will see why the story was told...each story I tell has a part of me in it and helps prepare me for my other writing, but some of my stories have more of me in them that others. The One Week...

Birth of a Rose

by maturesubmale_for_F on Apr 13, 2020
Transgender & Crossdressers

The birth of a Rose The following story is a fantasy. But a fantasy rooted in experience and reality. This is what I am and these are my desires and longings. Mistress Amanda embodies what I wish for, and though the woman portrayed in the story is not real, the portrayal of her does contain many elements of women I have known and loved. I live my life...

Miss Jennifer Fucks Little Tiffie

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

The Saturday after Miss Jennifer had her boyfriend fuck my pussy/bottom, she called to me while I was doing her laundry and told me to come to her room. As I entered, she told me to come and stand in front of her, where she was lying on her bed. I was, of course, dressed like a proper little housewife, with my pink lace bra stuffed with my big 54DD falsies...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

The Real Estate Broker’s Boyfriend

by VodouBlue on Sep 14, 2017
Fetish

Paula seduced him, the cougar, but Bob was young and vulnerable to her vastly greater experience. One of the first things she did was bed him. She sucked his dick into her warm mouth, drooling all over the shaft as she bobbed up and down, swirling her tongue expertly. Her strong index finger worked its way into his ass, wriggling and pressing. It gave him a...

Tales from the Oedipal Zone

by crazydorian on Mar 24, 2019
Fetish

The Oedipal Zone idea is a creation of Squelchapron, from his old “freeusecaptions” Tumblr. The original captioned stories (Field Observations and Paragon Magazine) have been used here with his permission. An Oedipal Zone is an area within a more general free use world. The normal free use tropes apply in most parts of the world: society functions more or le...

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My New Life

by cuckytoher on Aug 18, 2017
Fetish

Snow was falling heavily as I rushed to get home from work and start my weekend. This weekend however, would be like none I had ever spent before. It was my last day at my job and I had been recently laid off due to cutbacks and restructuring. That morning when I arrived at work I had been a handsomely paid executive bringing in a six figure salary, and that...

It Really Does Happen

by lipsticked on Sep 26, 2017
Fetish

This story is copyright 2009 by (lipsticked11). All rights reserved. No reposting without permission. * I am owned by a dominant couple and their niece and used as a live-in maid, cook, and sexual slave. My name was Michael, now I am Michelle. This is my story: When I was 35, my wife Connie and I lived next door to another married couple, Denise and Steve...