Sissy Stories

5,571 results
Orientation
Length
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Infinite Scroll

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

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The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

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Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

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Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

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My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

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Sissy's Special Night

by mdw_dark_angel on Sep 17, 2017
BDSM

This girl was so excited as Master had agreed to a special surprise for sissy from angel. Master took sissy to work and came right away to fetch angel to return Home and ready things for angel's surprise..."Sissy's Special Night". Y/you see, this slave has belonged to Master... though one has not always retained one's physical collar... since Master first c...

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From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

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Sissy Chantel, New Reality Ch. 05

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, My Surprise. "Ohh, Ahhh...Wha...what." I say as I wake up and am lost with where I am and what is going on. "What the... What the Hell? Where am I and what is this? Huh, what the Hell? Why am I chained and padlocked around my waist?" I'm groggy and very confused as I look at the room, dimly lit with a single hanging light bulb, I'm on...

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Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

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Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

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