Sissy Wedding Stories

39,844 results
Orientation
Length
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Infinite Scroll

My Cuckold Wedding

by CuckinChastity on Sep 16, 2017
Fetish

Note - this is a piece of fiction. The characters are not real. The scenario is purely a fantasy and does not describe any actual relationship. Laurel is not my actual wife. Enjoy! ***** I stood at the altar alone with Rev. Carl, the minister, looking out at the wedding guests. It wasn't a large wedding, still to me it seemed there were a lot of people l...

The Dragon Ring Ch. 05

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

Councillor Cadwill was there already, having arrived minutes in front of us. "The talk is all of Prince Hallit being wrong footed. There are some that want to press forward, take him down a peg, but there are some that worry about reprisals; sabotage of their place men. It's turning into a kerfuffle large enough to attract the vultures of the café commentat...

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...

Outed and Married Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

The head of his cock pushes hard against the back of my throat. I struggle not to gag. I struggle to control my gag reflex. I feel my throat spread open as he pushes his erection all the way into me, pushes deep into my mouth. It never gets easier no matter how many times he's done this to me. I feel that brief flash of slight pain as he deep-throats me. Fro...

The Sexy Cuckold Couple Pt. 08

by cuckcpl4play on Sep 19, 2017
Fetish

As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoralized submissive. My wife, who was the love of...

Reality TV

by JJ Neal on Sep 25, 2017
Transsexuals & Crossdressers

I didn't recognize the number, but I certainly recognized the voice and understood the message, 5:30, Jackson, Bride. My Master isn't given to long conversations with me, or any explanations. My role is to make it happen. I met Master Fred in a sissy chat room and he swept me off my high-heels. By way of background my sissy name is Jamie Jo. I'm 44-years...

New Year Cuckold Ch. 02

by 0131aj on Sep 16, 2017
Transsexuals & Crossdressers

After the party at New Year Julian realised his marriage was over. He had have been working overseas for about five years and the strain eventually had proved to be too much for his wife. Ever since their wedding day he was aware that she was having a series of affairs with other men. She was a beautiful brunette, with superb legs and shapely figure, confide...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Payson's Wedding

by fantaseeboy on Jun 5, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Very early on in our relationship, Becky learned how much I enjoyed anal play. While lying naked across her lap, she was giving me one of her mind-blowing handjobs when she suddenly slipped a finger between my cheeks and touched my wrinkled hole! I obviously wasn't expecting it an...

Mistake

by magmaman on Sep 13, 2017
Loving Wives

{This story has sex outside of marriage in it, so if you will be outraged, then be forewarned.} +++ Sissy lay there in the soft bed, her mind in a whirl. She could hear the soft snores of the man who lay beside her. The room kept blinking to a reddish hue, right outside were the motel's large neon lights. She remembered seeing those, the red portion was...