Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

The Making of a Mistress Pt. 04

by EiryCGar on Jul 13, 2020
BDSM

Author's note: The saga of Mistress-in-Training Marie and her sissy Charles has reached the point of their marriage. After the ceremony, Marie achieves her ambition and becomes a hotwife, making Charles a cuckold in the process As in all my fictional stories, all characters are over the age of eighteen, and all sexual practices described are performed conse...

The Awakening of a Sissy Pt. 07

by sissyjolie4u on Mar 9, 2020
Transgender & Crossdressers

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me. All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying us...

Hiking Cuckold

by hunfy on Sep 1, 2017
Group Sex

A car pulled up on the highway as I was seated on the bench by the bus stop. Out of the car came a stunning curvaceous 20 year-old brunette, Megan. I had met Megan when I went to school, and quickly fell in love with her, but she didn't love me back. Instead she had other plans for me, turning me into her and her stud boyfriend Joe's chastity slave. Megan ha...

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...

Courtesan Ch. 28

by Goodhusband on Sep 19, 2017
Loving Wives

This is the twenty-eighth episode in a series entitled "Courtesan". If you have not read the previous twenty-seven episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alt...

A Morning's Service Ch. 02

by Philippasubmaid on Dec 10, 2017
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive crossdresser. If you are offended by tales of BDSM and sex between consenting adults then read no further... other wise enjoy. Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue... ***** As I laid on the floor I strained to hear what m...

The Sexy Cuckold Couple Pt. 14

by cuckcpl4play on Sep 26, 2017
Fetish

Part 14 Pool I As we departed the room, I was utterly shocked that Master was in fact going to make us walk through the hotel as we were. He walked with his slut in front and I brought up the rear, but following closely in tow. I kept my head down but could feel the stares and after walking by a large group I heard the individuals bellowing at our predicame...

My Teasing Hotwife Ch. 04

by footslave85 on Mar 25, 2019
Fetish

Part four -- the evening out I look down and see a small dainty gold chain with a little item hanging off it. I wince as I see that it's not the key to my chastity cage but a symbol, the ace of spades, which signifies her status as a hot wife who enjoys the company of black men while her husband is caged in chastity. She can barely hide the giggle from her...

March Madness Ch. 08

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

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...