Cuckold Sissy Maid Stories

25,992 results
Orientation
Length
Source
Infinite Scroll

First Time Cuckold Ch. 04

by Angelscuck on Sep 14, 2017
BDSM

Oscar could smell her vaginal juices from his proximity kneeling between her legs. Her delicious cunt beckoned his waiting mouth. "I do need to warn you dear that I'm a squirter!" Bea cautioned. "Once my floodgates are opened its head for the high ground!" "Let it pour!" Oscar replied as he buried his face deep between her thighs and tasted he sweet guim....

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...

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...

Intervention

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

My fiancée's girlfriends were becoming a little apprehensive about the changes Angel was exhibiting since we had started dating. They had noticed her attire had become much more suggestive, and her make up more severe. There were other changes too. She was now sporting a tattoo on her right shoulder, an angel/mermaid holding a heart with my name on it. Sh...

Devoted Cuck Ch. 02

by cuckyfucky on Dec 18, 2018
Fetish

This is Chapter 2 of my ongoing series. Chapter 1 can be found in my profile. ***** I was cleaning the kitchen in my sissy maid outfit when the phone rang. Seeing it was Lina, my wife, I immediately picked it up. "Hi cucky, are you finished with your chores?" she asked. I could hear music in the background and so I knew she was still at the club. "Yes L...

He Looks Like His Father

by RainStevens on Sep 13, 2017
Interracial Love

WARNING! This fictional story isn't for everyone. It involves cuckolds, male feminization, submission, interracial sex and breeding. If you're not interested, go find another story. * I am a white fifty something year old married cuckold and a proud member of the W.B.A. My wife is twenty years younger than I and we have four children (with one on the way),...

I Learned My Lesson Well Ch. 02

by Angelscuck on Sep 14, 2017
Transsexuals & Crossdressers

As I told you in part 1, Angel really taught me a lesson regarding cumming without her permission. I was so grateful that I hadn't lost her to a superior black stud, I was even afraid to masturbate to porn on the internet. We have two computers, hers and mine, next to each other in our office. She told me she had forwarded an email to me from one of her gi...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...

Confessions of a Cuckold Ch. 03

by UpstaterNY on Sep 12, 2017
Loving Wives

It must've been the soundest sleep I've ever had. I woke up and saw that it was already 9:34am, my wife Brooke was fast asleep in the bed next to me. I laid there for a while trying to re-live in my mind the previous nights events. After a long time of role-playing, Brooke actually cuckolded me. She had sex with Derek, who is her hairdresser, in front of me...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...