Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

Tammy the Love Muffin

by ofloveandlust on Apr 10, 2018
Loving Wives

It had been more than a month. At first, he ignored the hair, the baggy pants, the granny panties, the immense bras that looked like they were designed in the 50's by a structural engineer. He still hit on her. She told him no. After a couple of weeks, he stopped trying. At the one-month mark, he suggested they needed to talk. "I guess you need to do what y...

New Jack Ch. 05

by deviantradoddness on May 15, 2018
Group Sex

I welcome your thoughts and feedback. Please send me a message and let me know what you think. ***** 5. Jack awoke early amidst a tangle of arms and legs, two sets of large breasts pressed against his upper arms. He slid out of bed, doing his best to let the nude sleeping women continue their rest as he padded into the bathroom to complete his morning...

Imprisoned by My Fantasy Ch. 01

by Jemina004 on Sep 14, 2017
Transsexuals & Crossdressers

"She likes what?" Xavier rumbled above me, his muscular legs on both sides of my head. "Being a prison bitch. It's her ultimate fantasy." My wife Lexi said, giggling as she nestled closer to her boyfriend on the bed. Our bed, in fact. My wife Lexi was in her early 30's, but had the same drop-dead gorgeous body she'd had through college. She was a blonde ha...

Ladyboy for my Thai Wife

by StarfireMayo on Sep 19, 2017
Transsexuals & Crossdressers

Dear Reader: Some people are not comfortable with their own sexuality and they object to cuckold stories and wife sharing. That is okay - To those people I would suggest not to read this story or to leave negative comments. To all the many others, and especially my thousands of readers and fans please read on- and enjoy. If you like this story, do not forget...

Strange Cocks Shoved Into My Life

by CAPT-CockAssPussyTit on Sep 12, 2017
Loving Wives

I had been married three times and been used by countless strange cocks, but it wasn’t all my fault. I was led astray from the start when I was still naive. Here's a brief summary of my eventful, sexual life but first, let me tell you a little bit about myself. I'm in my late thirties but still as sexy as ever. I could still make heads turn, but most men a...

Dating Our Neighbor Ch. 07

by Karenkay on Sep 19, 2017
Interracial Love

It was late Saturday morning. Matt was gone playing golf. Darla picked up the phone and called Rex. "I was just calling to see if you were up!" Rex chuckled. I've been up since early this morning. I saw your husband drive off with his golf clubs about an hour ago." "Matt has to play his golf every Saturday." "Why don't you come over and have a drink and...

Nope. I'll Take Option Three

by FinishTheDamnStory on Sep 14, 2017
Loving Wives

~ * ~ * ~ * ~ * ~ * ~ * ~ No honey, we don't have to talk. She chose the wrong man to betray. There's no need to talk about it, not with a man of action. An original quick little flash story for the BTB crowd. Partially inspired by a truly great song. Partially inspired by valeriahart's Karen and Mark (the bar meetup scene). I know that I usually write...

John's Domination Ch. 01

by wannabebitchboi on Sep 19, 2017
Fetish

This is a fantasy I've had for quite some time, and that has been growing in my mind more and more. This is my first attempt at a story, please give me criticism. I can handle anything you throw at me, but I would appreciate as much feedback as possible. John is a military man, with a type a personality. He was 5'9", 180lbs, athletic build, short milita...

Opening Sarah Ch. 03

by Bigdenverman on Sep 16, 2017
Loving Wives

Sarah was on the bed, sitting on her knees and clutching a blanket. She was holding it in front of her like a shield, as if needing to hide. Sarah was smiling at me, however, looking up from behind the blanket with those bright green eyes. She had just been pinned down and fucked by Brad for the second time in a month, which she obviously enjoyed. At that mo...

Post-It-Note Confession

by MattressThrasher on Sep 14, 2017
Loving Wives

This is based on a story someone told me about so there is a hint of truth to it. I did embellish it quite a bit, but the core of the story, as far as I know, is true. I don't know any of the people whom this happened too. The names I used I picked at random. ***** It was three days before my wedding to the woman that I was so completely in love with. The...