Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

A Twisted Wedding Night

by FrostShard on Sep 18, 2017
BDSM

"Did you really think that you were going to consummate this marriage, my dear?" giggled my newlywed wife. "I know we're married now, honey, but that doesn't mean I'm a different person now. I still have the same needs." Alicia was absolutely gorgeous in her bridal wear. The very picture of innocence. If people only knew. "But, Alicia, it's our wedding nig...

Meet the Danvers Ch. 02

by eeric on Nov 26, 2019
Interracial Love

Jim Danvers sat behind his desk on the third floor. He had been the office manager for the last five years, and the last couple of years had been quite profitable for the company. "Have to congratulate you again Jim, another year, and we've seen nothing but increased revenue streams and productivity from your floor." Charles Vanderholm stood up. The man wa...

Correspondence Ch 1.01

by jimmysub on Sep 17, 2017
Loving Wives

July 15,2001 Dear Jimmy: Lauren mentioned to me that you were feeling cranky and unappreciated by us. I am writing this note to express my respect and appreciation for you. She pointed out that your tolerance for being teased seems to vary. When I tease you it is in good clean fun. We might like to see you blush, but there is humor in your brining us coff...

Black Cuckold Revolution

by Samuelx on Sep 16, 2017
Interracial Love

Who says the cuckold lifestyle isn't for black folks? Don't believe these fools. Just ask me, Shante Philemon. Five-foot-nine, curvy and sexy, with dark brown skin, a thick Afro and a nice, big brown butt, that's me in a nutshell. A proud Creole beauty who is one hundred percent comfortable in the skin she's in. I'm a young black woman of Haitian descent liv...

Easy and Hardy

by Tiberius_Daniel on Aug 6, 2019
Loving Wives

Don't miss this modern fable. It's a fictional story, has nothing in common with reality. Please don't suppose anything; I give you only original stories. For local flavor, I used English and London words and phrases. (Example bare means a lot, fag= cigarette.) ***** First chapter For today we have two couples who lived in Chiswick, where rents are high...

Tony's Ascent Into Cuckolding Ch. 02

by Cuckyboy3 on Sep 15, 2017
Loving Wives

Later on, Linda told me the additional things she had decided. "I'm going to get my hair cut short." "Did Brad ask you to do that?" "Yes. I know you like my hair long, and it will grow back. But right now, I'm cutting it to just to please him." "We'll also have to go to the mall tomorrow to expand your wardrobe of fem attire so that you can be dressed app...

Adult Trip Pt. 02

by cuckcpl4play on Jul 3, 2018
Interracial Love

The trip back to the room was embarrassing given I was coated with the cum of my new Master. I rushed back and within seconds of arriving, my phone went off. The text read, Dearest white slut, please provide an inventory of the sex toys that were brought with you. It is now 4:00 and I expect you and your small dicked cuckold husband to join us on the beach...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

Cuckold Sissy Husband Goes Further

by keptsissy on Sep 18, 2017
Loving Wives

PART EIGHT: "Baby, I've been thinking about you. Been thinking you need something more to look forward to. I think that you would enjoy cumming more, enjoy your little thing played with more if it was more a special occasion." She's seated at the kitchen table. She has a small package on the table. "Come here." She watches as I walk to her. "Mistress, I n...

The Awakening of a Sissy Pt. 08

by sissyjolie4u on Mar 30, 2020
Transgender & Crossdressers

It was only a matter of minutes before Mistress pulled the car into a long driveway. My mind was still processing the idea that I was now on hormones. Once we were parked, Mistress had me grab my bag and follower her on the path to the house. She clearly knew this pace well, as she walked right into the house, with me following closely behind. As soon as we...