Sissy Wedding Stories

39,844 results
Orientation
Length
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Infinite Scroll

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

The Dragon Ring Ch. 06

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

"I thought I might find you here," he said, popping his head around the door. "We have pegged them with irony. They are to pay for a mercenary expeditionary force to go in and take control of the country. Then to stay and train a new army for you, there's sweet justice in that." His glee was overflowing, giving him an unnatural presence. "Come, this calls...

Getting Married

by hotdaddy9 on Mar 17, 2020
Transgender & Crossdressers

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home...

I Get Married

by hotdaddy9 on Mar 7, 2020
Transsexual

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home and...

Open in Reader

The Clothes Shop... Pt. 01

by Manndee on Apr 10, 2018
Transsexuals & Crossdressers

I looked at my watch, "Fuck it...nearly six, ...I bet they will be closed!" I parked the car and walked towards the shop. It was raining, it was cold, a typical January Saturday. "Bradley will fucking kill me if I forget my suit!" I smiled to myself. "The man's a dick for getting married anyway!" I walked towards the door, 'Fuck, is it open?' The lights we...

The Whore Wife, Sissy CD Husband

by MILF4black on Jul 27, 2020
Transgender & Crossdressers

This story is completely fictional. All characters in the story are over eighteen. Prologue: The Whore wife, Sissy CD Husband "That's it, you little sissy whore, suck that cock." Jennifer told her husband as his head bobbed up and down on the strap on dildo Jennifer was wearing. Her husband, Patrick, lifted his head and the seven inch fake penis slid out...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

The Wedding Ch. 09

by betamale08 on Apr 1, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 9 – Coerced, Consumed and Consummated... After wrestling my Uncle John out of his suit and laying him out on his back, I knew his passed-out routine was all a farce as he looked to me winking with a smile before going back into his pretend-coma... Faking it in front of Patti and no doubt doing so in the want of stay...

Payson's Wedding Ch. 02

by fantaseeboy on Jul 16, 2019
Transgender & Crossdressers

The next morning, Becky and I walked into the jewelry store a few minutes after it had opened. The older man who owned the store looked at us with a funny expression on his face. We approached him hand-in-hand. Becky, with her Hispanic heritage, was wearing jeans, a white blouse that draped over her giant breasts in the most alluring manner, and white cross...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...