Cuckold Sissy Stories

12,909 results
Orientation
Length
Source
Infinite Scroll

How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

She Forces Me into Cuckoldry

by hismasterdivine on Sep 25, 2017
Loving Wives

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax! ***** Dominant girlfriend wants a black lover, deluded b...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

I Learned My Lesson Well Ch. 01

by Angelscuck on Sep 14, 2017
Erotic Couplings

My wife and I have a wonderful relationship, so much in love, and so much in common. It was a love that defied all loves before it. Our sex life was good with lots of playing, kinky fun and good old fashion oral sex. Having had radiation treatment for prostate cancer, I was left with erection problems. I could never get hard enough to enter her. I could us...

Becoming a Sissy Cuckold Ch. 02

by Pantieslave on Mar 26, 2019
Fetish

Beth was now fucking Jerry every 2 or 3 days and each time they had sex Dan was required to be dressed in girly clothes and made to watch them as well as to video them. Beth loved watching the video's with Dan on those days that she didn't have sex with Jerry. Dan was also required to suck on Jerry's cock getting it hard so that he could fuck Beth and Dan wa...

Cuckbitch Pt. 01: Confession

by Satin_Dani on Jun 19, 2019
Fetish

"Good morning bitch," the text message woke me up. "Have as much fun as I did last night?" It was almost a rhetorical question, although I did have fun. Lucy is a senior officer in the Army. We met years ago in our formative years when I was still in the military. We became good friends and maintained the relationship over the years. We were like best buds:...

Cuckolding Ricki

by mmms_ricki on Sep 17, 2017
Loving Wives

MMM's HotTub Party & Cuckolding ricki MMM had not been back to Oregon for over 8 months and was anxious to spend some time with her best girlfriend Jill and her significant other Roger. Mary was sure that Roger had a crush on her and was anxious to take things a little farther if Jill approved and Mary made the opportunity occur. MMM had been training her...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Discussion with a Wife of a Cuck Ch. 04

by wantyou on Sep 16, 2017
Loving Wives

1/26 E-mails This chapter starts out with me answering Alice's question. I wrote: First my answers to your questions! Alice wrote: The story is fine, but you have not included anything about what I have told you so far. I will as the story moves move and more into your meeting and the sex and then afterwards when you start to see Tyrome. I answered: I...