Cuckold Sissy Maid Stories

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My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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Foot Cuckold for Isha Ch. 02

by cuck_for_isha on Sep 16, 2017
Fetish

Hey guys, Rahul is back with yet another cuckolding experience with Isha (goddess) and my master (Atul). This is Part-2 of the series. So I am back with the tale of another day of my life. I was cleaning the house as instructed by my goddess, who was out with her boyfriend, Atul, for shopping, with of course my credit card to handle the expenses. They had...

Cuckold Hypno Assignment

by DivinaTellsAll on Jan 1, 2019
BDSM

My name is Divina. I serve Goddess K. and Madam Vega. I am on a journey to become their perfect sissy girl, and a cuckold slave to Goddess K (who is my wife). The following is a true story of an assignment given to me by Madame Vega, and carried out with Goddess K. Assignment: Watch cuckold hypnosis video pornography, with my chastity cage locked and and...

Dear, We Have to Talk Ch. 04

by dr13bone on Sep 25, 2017
Interracial Love

My wife, Mindy, had discovered my secret stash on interracial cuckold porn on the computer. Rather than getting mad we decided to explore the fantasy. With each new adventure my wife came closer and closer to being fucked by another man's cock. I knew I could stop it at any time and that was the danger of the game, the ability to stop and not doing so. Now s...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

My Teasing Hotwife Ch. 03

by footslave85 on Mar 25, 2019
Fetish

Part three - the dreaded choice My wife and Mistress is now dressed beautifully and ready for a fancy meal and a few cocktails at a rather expensive restaurant and bar. I met my wife in our spare bedroom where I immediately see what has been laid out on the bed. There are two outfits, one is my nicest blue suit with a new shirt and tie that my wife has obv...

Sissy Cuckold Husband

by bisissystephenie on Sep 16, 2017
Fetish

If you don't like sissy, cuckold, bisexual men stories, then please don't read it only to complain. You look stupid! ***** Like many husbands, I've wanted to see my wife fuck other men. I like the idea of being a cuckold. I had thought my wife Pam had been fucking a man but I had never seen it. One afternoon a friend of ours came over while my wife was at...

Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017
Fetish

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...

First Time Cuckold Ch. 02

by Angelscuck on Sep 14, 2017
BDSM

I thought about the wonderful night I had just experienced with Jordi, my handsome, strong lover. How he made me feel things I had never felt before, his beautiful body, his magnificent cock! I started getting hot and wet, just thinking about him. Then I looked at my husband Oscar. How pathetic he looked. Drinking my lover's cum just for a chance to hear ab...

Unexpected Encounter Pt. 01

by cddream on Mar 6, 2018
Fetish

It was a week night and I received a text from an ex girlfriend I haven't talked to in 2 years. I stared at my phone in surprise when I see her name pop up. My heart kinda skipped a beat and I opened the text anxiously. It was from Molly, she was the first girl I exposed myself to. She knew all my secrets and kinks from our past together. The text simply re...