Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

28 Days

by tinywhiteboi on Dec 2, 2019
Interracial Love

28 days. That's 4 weeks since my last orgasm. And I was so horny, to the point of constant distraction. It was all I could think about. My locked little penis was dripping into my panties, and my little balls were swollen. Six weeks ago my wife, Angie, caught me jerking off to interracial cuckold porn, a video with the cuck locked in chastity. She'd come ho...

Tony's Ascent Into Cuckolding Ch. 03

by Cuckyboy3 on Sep 12, 2017
Loving Wives

She called Brad that evening to let him know that I had come around after some convincing. They chatted for a while, during which she told him about my misbehavior. She moved away from me and talked softly for a while from the other room. Finally, she came back to me. I heard her saying, "Do you promise? You'll do that for me?" Then she listened for a while...

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Francie and Graeme's Defloration

by skriblur on Sep 12, 2018
Erotic Couplings

The odd-numbered parts have the sex. The even-numbered parts have the love story. ~1~ Francie likes what she's seeing -- her feminized husband. All slutted-up in strappy heels and frilly socks, a cute cornflower blue skirt and white cotton blouse, kneeling in front of the living room couch, sucking off one of Francie's boyfriends. Francie (wearing nothin...

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...

3 AM: She Finally Comes Home

by siscuc on Sep 16, 2017
Fetish

I had nervously been awaiting my wife's return for the last two hours after finishing all my chores. The house was spotless and i had done all the washing and ironing she had left for me to do. I was ready to greet her at the doorway with a curtsey just as she had told me to. I was still wearing my new maids outfit, with fishnet stockings, lacy black pantie...

March Madness Ch. 09a

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...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

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...

The Bradfords Ch. 01

by Erotictales4u on Oct 13, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and transsexual/cross-dressers niche, it is focused on humiliation. This is the first of a new series. I would love your feedback. ***** "What the fuck is the meaning of this Tim!" screamed Tim's wife Jane as she ran her hand through her lo...