Sissy Chastity Cuck Stories

13,492 results
Orientation
Length
Source
Infinite Scroll

Carol's Gifts

by Belongs2Beth on Sep 16, 2017
BDSM

Authors note: This is the third story featuring characters introduced in "Carol's Christmas." In this installment Carol give's Jack his Christmas gift one night late with the help of Irena, "Marcia" and several well hung younger men. The sex action in this story is unrestrained, and since the tags are at the bottom of the page, I will issue the following mil...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

Carol, Candy & the Ex Pt. 02

by corduroysissy on Mar 26, 2019
Transgender & Crossdressers

(Will Candy make a good cuck?) Davie was standing at Carol's front door dressed in a pair of copper brown wide-wale corduroy dress trousers, and a beige polo shirt. Oddly enough, he felt more nervous than he did the night before when he was in full drag, and he attributed it to the ex-factor. Last night Davie as "Debbie" was there to meet Robbie as "Candy"...

Beta Male Slave Academy Ch. 01

by Tazokm on Jul 13, 2020
Fetish

My head was still spinning. I kind of heard what was going on, but not really. "Right, Patrick?" my girlfriend asked me. I had completely zoned out. After an hour long car ride to a large compound in the middle of nowhere, I had time to contemplate what was going on. Still, my girlfriend telling me she wanted to have me trained to become a slave was very pu...

Dear, We Have to Talk Ch. 06

by dr13bone on Sep 25, 2017
Interracial Love

I was in the house by myself for a month while my wife and Karen went abroad to get her augmentation done where the price was a lot lower, they made a vacation of it. When I picked her up from the airport it was a cold November day, but even through her coat I could tell her figure had changed radically. She had done a makeover, her hair short and blond now...

Small's Story

by Cuck_Maker on Sep 16, 2017
Loving Wives

Mark...Alex...Trevor--these are some of the names I've caught her saying over the hum of her vibrator. Behind the door cracked open, she kept everything under the sheets so you couldn't see below her shoulders. Which is fine; If you saw her strutting downtown you too would first notice her lean face--starting with those cold blue eyes always looking straigh...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

My Path Pt. 04

by Miguel59 on Sep 17, 2017
Loving Wives

Moira gave me the security code to her garage which allowed me to enter her house. on the kitchen counter were my instructions. Pretty straight forward. Vacuum, dust, mop, clean the bathrooms, strip the bed, put new sheets on, wash the dirty ones. She emphasized the need to pretreat the stained area. After shedding my clothes I went to work. Being nude was r...

Cuckolding: The Lifestyle Ch. 01

by Karenkay on Sep 16, 2017
Interracial Love

Madison sat reading the book that her husband ordered for her online a few weeks ago for the second time. She sat on the living room sofa dressed in black lingerie that Ted bought her along with her favorite fluffy slippers. The book was about the subject of cuckoldry. A subject that Madison just learned about during a discussion recently with her husband Te...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...