Cuckold Sissy Stories

12,909 results
Orientation
Length
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Infinite Scroll

Ms. Tanaka Fixes Me Ch. 02

by chenwanli on May 4, 2020
BDSM

Chapter 2- Ms. Tanaka Takes Charge Ms. Tanaka stood up, straightened her sheath dress and bowed to her daughter Hiroki to say goodbye. They exchanged a few final words in Japanese that I didn't understand, gesturing at me and smiling then Ms. Tanaka laughed throatily and demanded the rest of my clothes. I took my pants off from around my ankles and gave her...

Financial Difficulties

by tazsis1 on Sep 12, 2017
Loving Wives

We got into some financial difficulty a few years ago. I'd borrowed a lot and Elaine and I spent too much over one Christmas on the kids and family. And then I lost my job. It was all very difficult and, as these things do, it affected our marriage profoundly. While we kept our troubles from the kids, Ellen and I talked about little else -- driving out all p...

The Sexy Cuckold Couple Pt. 15

by cuckcpl4play on Sep 26, 2017
Fetish

PART 15 POOL 2 As we walked outside, I noticed that our private area was more populated than expected. There were a few more additional males but more than a handful of additional and very attractive females. Sir Jeremy approached my wife quickly and I watched as the other women gawked at her and then began laughing at her as several of them even engaged in...

Total Drama Island

by Yelawolf on Oct 12, 2019
Fan Fiction

(Every character in this story is 18+) You step off the boat last. You see all of your competition. Most of the chicks looked pretty damn hot. Especially the cool goth chick. The guys mostly seem like idiots besides a tough-looking dude with green hair and piercings. You walk on the dock seeing the poor condition of the island for the first time. You didn't...

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Cuckold CEO Ch. 07

by drdick69 on Oct 16, 2018
Fetish

I awoke Saturday to the sounds of running water. My wife was already up and in the shower. My head was still swimming from that activities of the night before. Our playful cuckold game had taken us to a different level, with me being submissively used for the pleasure of my wife and her lover. More worryingly, the comment my wife made, before I went to bed,...

The Awakening of a Sissy Pt. 08

by sissyjolie4u on Mar 30, 2020
Transgender & Crossdressers

It was only a matter of minutes before Mistress pulled the car into a long driveway. My mind was still processing the idea that I was now on hormones. Once we were parked, Mistress had me grab my bag and follower her on the path to the house. She clearly knew this pace well, as she walked right into the house, with me following closely behind. As soon as we...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

The Sexy Cuckold Couple Pt. 06

by cuckcpl4play on Sep 19, 2017
Loving Wives

My New Life at Work...First Week Continues Part 6 I arrived home that evening (Monday) and felt exhausted by the roller coaster ride we had experienced over such a brief period of time. It brought me great comfort that Master must have some good intuition as allowing me to get home and be in my wife's arms, his slut's arms, tonight was truly needed. Also, o...

A Cuckold Earns His Horns Pt. 02

by lapraline70 on Sep 16, 2017
BDSM

This is part 2 in a series of letters about my cuckolding. For context, read part 1. We open with O/our Bull knocking at the door on the fateful evening. ==== Already on my feet, i walked to the door and, fumbling with the handle a bit, opened it to see Him. Our eyes met. i saw His immediately slide down my nightgown as His grin widened. "Ah, good evening...