Cuckold Sissy Stories

12,909 results
Orientation
Length
Source
Infinite Scroll

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

The Making of a Mistress Pt. 06

by EiryCGar on Sep 14, 2020
BDSM

Author's note: 'All things must pass' and I feel that this series has reached a natural conclusion. As always, I must point out that all players in this fictional saga are aged 18 or older, and all sexual acts are consensual. The Making of a Mistress Chapter 6: Cwm Pechod's Cuckold Community The invitations to the party for the combined wedding anniversary...

Mistress Morgan's Sissy Husband Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Robin arrived home from work about 5:30 on Thursday, he still felt a little apprehensive about what happened Tuesday night with his sissy friend Patty, and he hoped he might get to talk about it with his wife Morgan. He really enjoyed wearing the corduroy skirt outfit she bought for him, and he loved being a sissy whore for his wife and Patrick, her "boyfrie...

Mistress Kia Versus Samuel X!

by Samuelx on Sep 17, 2017
BDSM

For over two years now, the bisexual Haitian-American male known as Samuel Xavier had been pleading with his tall, curvy and sexy African-American dominatrix, Kia Holbrook, also known as Mistress Kia or simply Lady K, to turn him into a submissive Sissy slut like he was born to. For the dominant Black woman, doing something this drastic to a Black man wasn't...

Letting My Wife Cut Loose Ch. 04

by weaponx on Sep 17, 2017
Loving Wives

As the video continued, I watched in amazement as Beth's pussy welcomed Jeff's throbbing cock in one gentle push. Within seconds Jeff had completely submerged his cock into her pussy. As soon as he had rested his loins against her back side completely entering her, the camera panned back to show Beth's body. Beth's head pulled back and her arms pulling again...

Dreams do Cum True

by eviltwin52 on Mar 30, 2020
Loving Wives

"Wait, what?" I said raising my face out of my wife's cum filled pussy. "He wants you to suck his cock johnnie," Cin hissed. "Thomas said that if you like eating his cum from my pussy, you might like getting it from the source. Now finish what you started my dear sweet cuckie and get the rest of the gift Thomas sent you." With that my beautiful wife of 8 y...

Cuckold Striptease Game

by Iftheshoefits on Sep 12, 2017
Fetish

I'd forgotten my damn key again. And my wife was taking forever to answer the door. What was she doing in there? I was mildly irritated by the time she finally opened up, but before my lips could even form the words to some smart-assed remark about how long I'd been standing there, my senses were overloaded with the sight before me. I gave her a once ove...

The Cuckold is Black This Time

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

After months of hesitation and much soul-searching, a momentous decision finally got made. The big Black dude burst into Mistress Chocolate's den in downtown Ottawa, Ontario, and told her of his rather unusual request. The six-foot-tall, gorgeous Black Canadian female dominant listened to him, and then agreed to make his most forbidden fantasy come true. It...

The Sexy Cuckold Couple Pt. 03

by cuckcpl4play on Sep 19, 2017
Fetish

Initial Fucking of My Wife part 3 It was 2:00 when we arrived home and suddenly Jen received a text from Master. Excited we are moving forward my owned little slut. I would like you both to arrive just after the sun goes down. The reason for the change is that I want you both to walk to my place and will do so in the same under garments you wore to my offic...

Dominating Sugar Daddy

by LittleDickSissy on Jul 3, 2018
Erotic Couplings

The sissy cuckold was at the ATM withdrawing cash for his Mistress. He needed cash for her nails, her new dinner attire, and makeup. As he made his withdrawal his little dick dripped precum in his purple lace panties. He always got turned on every time his Mistress provided strict instructions to him, and of course whenever she played without him. "Now tell...