Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

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...

A Dickens of a Life

by CBruch on Jul 17, 2019
Interracial Love

'Best of times; worst of times', it was Charles Dickens who started off his epic tale of 'A Tale of Two Cities' with that phrase and I have often thought that should my life be written about then those few words would neatly sum up my biography. However, given my life is not yet done, such thoughts maybe a little premature and there might well be a happy e...

How I Became a Chastized Cuckold Ch. 08

by gizzard on Sep 26, 2017
Loving Wives

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * Thin rays of golden sunlight glimmered through the bedroom window bl...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

Black Bulls in Chastity!

by Samuelx on Oct 3, 2018
Interracial Love

Meet Bartholomew "Bart" Jones, a big and tall young Black man living in the City of Ottawa, Ontario. Born in the City of New Orleans, Louisiana, Bart moved to the Canadian Capital to expand his horizons and explore new things. He had a Business Management degree from Louisiana Tech University, and felt like giving life in Canada try. Life in Canada had alway...

Poker Night

by grizzley123 on Sep 14, 2017
Fetish

We have the house ready. My chip set has been unpacked and stacks worth $50 are ready for the buy in. The men play dealer's choice from 7pm till 9:30 and then a Hold'em tournament or two often till late at night. Dinner is at 6pm. My wife has that ready. Since it is a cooler day in November she has made her delicious Massaman Curry with rice. There are other...

The Wedding Ch. 03

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 3 -- Dildos, Deeds and Dates... Riding back to the Gate-House in the golf cart, we had an extra passenger, my Uncle John... They were staying with us that night and with my slowly getting used to his comments and barbs, saying he was going to make me Patti's cuckold -- but knowing that he would be sleeping with Mom...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

The Sexy Cuckold Couple Pt. 17

by cuckcpl4play on Sep 26, 2017
Fetish

PART 17: THE NIGHTMARE OF VEGAS WAS NOT OVER It had not been even 15 minutes when I heard the door to the suite open. I was expecting to hear lots of voices, but that was not the case. Seconds later, the light flipped on and Karen stood there with a devious smile. "The night is nowhere near finished slut," she said and immediately she ordered both of us t...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...