Chastity Cuckold Stories

13,138 results
Orientation
Length
Source
Infinite Scroll

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

Brian Becomes Brittney Ch. 01

by BrittneyCummz528 on Sep 14, 2017
Transsexuals & Crossdressers

My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before college. The program was something my neighbor told me about. My n...

Me & My Wife Are Sisters Now Ch. 02

by gayindia1980 on Sep 16, 2017
Transsexuals & Crossdressers

This story is in continuation of my last story Me & My Wife Are Sisters Now Ch. 01 ***** Next morning, we both slept quite late then our usual time, I don't know about Shivika but I was still feeling cum inside my ass. Last night my wife, Shivika was fucked by 2 sexy men in a 3some and then one of them fucked me really hard. Shivika woke up around 9:30 an...

Bedroom Surprise

by wylite on Sep 14, 2017
Fetish

This story is a follow up to the 'Bedroom Research' stories. * I think my minds been messed with; a few months back I would not have dreamed of dressing up in girls clothes but now I was looking forward to a special delivery. Mandy had told me what to order and I had been busy on line picking out a nice pair of frilly pink panties and a pretty sissy dress....

The Scorned Wife

by Kandy5647 on Aug 18, 2017
Fetish

Hell hath no fury like a woman scorned.....unless it's a wife who is scorned And Alisha was a wife scorned. She stood in front of her bedroom mirror with her hands touching various parts of her naked body. She was trying to figure out what was wrong with what she saw. Every time she let her fingers go across her breasts or her clit she closed her eyes, bit...

The Party

by fetisha_44 on Sep 16, 2017
Fetish

To set the scene: I have been loaned to a dominant woman for the night, while her sub is serving my master. She is the owner of the Corset shop, where I was measured for my corset, and her sub is the girl Elise who assisted me. After licking each other to countless orgasms, and being fucked with her strap-on in my cunt and ass, I have fallen into a deep slee...

Enemas on the Beach

by suppleWriter on Sep 14, 2017
Fetish

Eve felt reasonably content with her life. She had a loving relationship with her husband Adam, her children had just left home to go to good colleges, and their 20th anniversary was coming up. But how to mark the special event? They were wealthy, but holidays abroad... well, they had done that. Finally, they booked a three-day break in a cabin by a remo...

The Vault Pt. 02

by undherfoot on Sep 18, 2017
BDSM

After Tiffany left, I found myself entertained for the rest of the evening. I had no plans for that Friday night, so I spent much of the night admiring the device that now kept me from my junk. It was a pretty ingenious device. It consisted of two clear plastic rings and a curved, clear plastic tube. My penis and testicles passed through the larger plastic r...

Frances Ch. 01

by paerotica on Sep 16, 2017
BDSM

The doorbell rang and since he wasn't expecting anyone, he tried to ignore it. It rang again and again. Finally he roused himself away from his computer and headed to the door, slightly irritated at being disturbed. Without checking who was there, he opened the door, figuring he would quickly rid himself of this unwanted visitor. He did not like people drop...

Anything for Lindsay Ch. 02

by allaboutcontrol on Sep 26, 2017
Fetish

It had been four days since Jason had promised Lindsay he wouldn't jack off anymore. Four of the most painful days of his life. He had no idea how hard it would be to not have an orgasm. He was on edge at all times, and constantly found himself sporting a raging hard on. Tonight, he thought, it would all pay off. Lindsay had the house to her self for the nig...