Cuckold Sissy Stories

12,909 results
Orientation
Length
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Infinite Scroll

The Ultimate Cuck Experience

by Joggles44 on Mar 12, 2021
Cheating Spouses

(UPDATE: Custom names for all main characters have been successfully added! Enjoy!) (Note from the author: Hello! Hope you enjoy my story. Before you start reading let me clarify that this story is set to "private", meaning no one can edit it or add chapters but me. I'd like to keep the writing to myself while the project is developing. HOWEVER, I...

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Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Dave's Wife

by Springer on Aug 18, 2017
Fetish

When I first met Dave's wife, I was stunned. After working with Dave for about a year as cooks in an inner city restaurant, we had become pretty good friends - that is, we had a good working relationship. Dave was about ten years older than me, heavy set, and starting to go bald fast. Me, I was the kid in the place, only 21. Working nights in a restaurant i...

Introspection Ch. 02

by edibles123 on Sep 16, 2017
Fetish

Chapter 02: The Party We dock at the chalet and Maddy informs me a couple of her friends have already arrived. She attaches a lease to my collar and sternly looks on my eyes. "For the next three days, you are my slave, Jackie, and you will follow my instructions to the letter. I will absolutely not stand for disobedience or poor behavior." I was truly sc...

Cuckold Chronicles: Paul

by deltonaman2man on Sep 13, 2017
BDSM

Friday night is my night out with the guys. I go to a friends house and we have a small neighborly poker game. My wife likes the time alone, so she stays home and does whatever it is that she does. I don't get out much since my heart attack ( at the tender age of 48). I'm in my mid 50's now and we have been together for over 20 years. We are still very much...

Life of Alex Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Alex sighed setting foot inside the small rental apartment which he and his lovely wife, Angela, rented for the year. Alex is a clerk working for a small medical store downtown. His income alone barely meets both ends for the duo. He set the large knapsack on the floor beside the table and said a little loud "God! I know asking for a luxurious life is prepos...

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

Sissy Cuckold & The Old Bull Ch. 01

by DirtyDaddyHunter on Sep 19, 2017
Loving Wives

He waited on the bed as instructed. He had dressed exactly as he was asked: A pair of lavender lace trimmed panties stretched tightly over the young man's small cock; a matching bra covered his hard brown nipples too. He also had on a garter belt and some high heels. Too top in off he had on some coral lipstick and he had painted his nails perfectly. There...

I Make Believe I'm a Cuckold Ch. 02

by donaldelliott11 on Jan 28, 2020
Fetish

This is the sequel to I Make Believe I'm a Cuckold. You should read that first. This chapter is dedicated to David, whose female coworker treats him the way he deserves. Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help me improve my writing; ratings help other readers find...