Cuck Sitter Stories

3,625 results
Orientation
Length
Source
Infinite Scroll

The Baby Sitter

by mischif2 on Sep 16, 2017
Group Sex

It was very late when they finally reached the front door. They had wined and dined and whiled the night away… almost forgetting they had promised to be home around midnight. It was now closer to two. They both entered the house softly, not wanting to disturb the babysitter. They were glad she had asked to stay over that night to make it easier for them....

How I won Back My Wife Ch. 03-04

by The_reader94 on Dec 9, 2019
Loving Wives

Bella began to explain to me the plan she had in mind. She introduced me to the concept of a cuck. I listened to her plan with pin-drop silence. She had my undivided attention. After she finished explaining me the plan, she asked me what I thought about it. "Are you sure this will work?" I asked Bella with concern in my voice. "If she loves you, then it w...

Step-Mother has a Secret

by call_me_dana on Feb 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** "Rachel ... Wait! I can explain." The curtain had already closed and she was gone. I looked in the changing room mirror and my untucked bulge was quite evident. I hurriedly re-tucked, stepped into my leather skirt and into my heels. Looking at the pretty young woman who had been...

Karenkay

by Chris Payne on Sep 15, 2017
Interracial Love

When I look back at how the whole business started I blame Karenkay. She is the prolific Literotica writer whose work is usually to be found on the Interracial pages. If not her, then it was the fault of my wife's little white poodle. Then again maybe no one was to blame. Maybe it all worked out as it was destined to do. I was sitting at my computer reading...

Devoted Cuck Ch. 03

by cuckyfucky on Dec 18, 2018
BDSM

Chapter 3 - My training begins This is a short summary of the changes that have happened in my life thanks to my wife's new lover and my master. 1 month has passed since Brad started living with me and beautiful wife Lina during the weekends. I thought I had it tough with Lina before, but it had gotten so much worse since Brad has moved in. My life was no...

The Babysitter Ch. 3

by Hrnyme on Sep 13, 2017
Loving Wives

It has been a couple of weeks since the last time I have seen that luscious body. I can hardly wait until our next outing so I can be with her again. I came up with an idea of taking my wife out for "a night on the town." The wife agreed to my idea and made all the arrangements for our sexy sitter to be here. When she arrived, our eyes met with desire, know...

The Two-Month Break Clause Pt. 02

by TheBiGuy on Mar 25, 2019
Fetish

After my first post, I received several comments. Some of the comments were positive and others negative. Any comments that were constructive, I will take the criticism and learn to incorporate those suggestions into the subsequent chapters and other stories I write. One of the comments was about numbering the story as Part 1 or some variation like that. Tha...

Taking Laurie for My Own

by n00bwriter on Nov 26, 2017
BDSM

I am extremely thankful for the simply wonderful job MamaK did in editing this story for me, going above and beyond any assistance I could have hoped for. Her instructions on creative writing have been nothing short of phenomenal and have certainly helped me to become a better writer. MamaK - Thank you! ***** I met Laurie working at my previous job. What...

The Start Of Me A True Cuckold

by milfwife on Sep 19, 2017
Loving Wives

It all started about a year ago when one night I brought up the idea of sharing her with another man. It was the beginning of me becoming a cuckold. I had mild fantasies of being one in the past, but as time went on my feelings for it only grew stronger. The thought of being another man's cuck, while he fucked my wife senseless in front of me and ordered me...

Webcam Cuck

by Fantasyman95 on Jul 27, 2020
Fetish

Two years ago I met a beautiful woman named Vanessa, we fell in love and shortly begun dating. Our relationship was very ideal, lots of cute romantic dates, nights staring at the stars, and so much more. The only thing we haven't done is going to third base or any further than that. You may ask me, Neil, why would you date a woman for two years but not have...