Crossdressing Cuckold Stories

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Orientation
Length
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Infinite Scroll

The Game of Trust

by TexasFarmBoy on Mar 9, 2020
Loving Wives

Round 1 As your basic naïve male, I made the mistake of opening the door to a game which I'm not sure I wanted to open. What game? You ask. Good question. For the lack of a better title, let's call it The Game of Trust. Confusing? Damn right it is and just as frustrating too. But I opened the door and have to live with the results and consequences. I'm G...

February Sucks

by GeorgeAnderson on Oct 5, 2020
Loving Wives

February Sucks. by GeorgeAnderson. This tale has its origin in a conversation remembered from some decades ago. The conversation shocked me, and made such an impression that I'm quite sure I remember its essentials correctly. A recent event reminded me of that conversation, and motivated this story. Thanks to BlackRandl1958 and stev2244 for their kindness,...

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...

The School Tramp

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

(From "Boy" to " Boy oh Boy!!") Chapter 1 - The School Tramp I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made. I was nineteen years old at the time and entering my junior year of high school. Yes, my ju...

Murder Misstery

by thrillerauthor on Sep 16, 2017
Novels and Novellas

(c) 2009 by Thrillerauthor When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the youngest traders at the Chicago exchan...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

Unwelcome

by thornapple on Sep 14, 2017
Novels and Novellas

Unwelcome Philip Johnson Prologue Good and bad things often come into our lives without warning, and that's how it was with Ben Whitehead. A simple impulsive notion to alter his homeward travels just so he could spend a short time dwelling on a place and time from his childhood. All so innocent and understandable. Something that many might consider doing,...

The Domme Diet Plan Pt. 01

by subm_atty on Sep 11, 2017
Fetish

Day 1—The Plan I have been fat as long as I can remember. I have tried various diets with no lasting success. Being uncomfortable with my body was probably one of the many factors that drew me into being a submissive. Two years ago, I met the Domme of my dreams. My Mistress was about 5'10" but towered well over 6' tall in the heels she usually wore. Her hai...

The Flag Girls Get Fucked

by Stormbringer on Sep 25, 2017
Interracial Love

The black jeep wrangler bounced as it cruised over the causeway. There was a loud HONK and the two women in the jeep jumped. Some college boys in a convertible Mustang moved over into the wrong traffic lane and pulled up beside the jeep. The guy in front made kissing faces at the driver of the jeep. A guy in the back seat, held his thumbs out pointing at him...

Summer Sunshine

by StangStar06 on Sep 17, 2017
Loving Wives

Hi Folks, First off a warning. This is a very long story so those of you with short attention spans might want to pass this one by. I haven't done a long one in a while and this one felt good. Those of you who don't really like long stories should realize that you read them all the time. Any time you read one of those three part stories that have five pages...