Crossdress Chastity Stories

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Orientation
Length
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Infinite Scroll

Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

The Adventures of Sissy Madison Ch. 02

by sissymadison on Mar 6, 2018
Transsexuals & Crossdressers

They all got into Kim's car ready for the trip. Haley turned around as soon as Kim started the engine looking Madison up and down. "You are just sooo cute, I can't even get over it!" and with that Haley got out and hopped into the back seat with Madison. "So do you like being all dressed up like this?" Kent nodded but didn't say a word. "Oh don't be l...

The Theater Pt. 01

by Stephisissycd on Sep 15, 2017
Group Sex

About a mile from my apartment is a porno theater. It plays hardcore porn films and is as seedy as it gets. Most of the people there are black and Latin men. I'm a petite white guy who has recently started to crossdress. Something about wearing slutty girls clothes makes me really horny. I'd drive past that theater and imagine walking in dressed like a tot...

The Truth

by MoistVonLipwig on Feb 2, 2021
Fetish

Beth entered the room as quietly as she could, conscious that she was running late. These kind of things never start on time, she thought to herself as she slipped into the dimly lit meeting room. Apparently this one did as her eyes adapted to the dark. She saw a couple of free seats at the back and made her way to the round table to try and catch her breath...

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Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

Caught by my Daughter and Wife

by rickiee_2002 on Sep 12, 2017
BDSM

It was Saturday morning and I heard the door to the garage close. My wife and daughter had just departed for a weekend in New York City. I was excited for them because they need some girl time together. I call her my daughter, but she is actually my step daughter and had just turned 21 years old on Friday. The two of them got along like oil and water ... the...

Life and Time of Lady Vargos Ch. 08

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"Lies, Truth, and Innuendo" Martin was pressed into attending to his duties that week as Lady Vargos. With little or no manly pride left to swallow or cling to, he performed his daily routines dressed as a woman, both publicly and privately. Each day seemed to bring more heart felt shame and humiliation into his life as he stepped out and displayed his ema...

The Marriage of Martin Hastings Ch. 17

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin sat alone in a small interrogation room. The large wood table with the two empty chairs on the opposite side of the table were all the furnishings in the room. The humiliation Martin had suffered as he was brought through the police station, the giggles, sneers and staring were still fresh in his mind. Though he was told he was not under arrest, he fe...

Inaugural Crossdress Sexfight

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

Hi everyone and welcome to the Crossdressers Sexfight League (CSL). My name is Dani and I'm the primary author as well as a regular participant in the league. The league title says it all. It's an erotic sexfight wrestling league for crossdressers of all ages where the loser is forced to service the winner of each match. It takes place in living rooms, bedr...