Sissy Wedding Stories

39,844 results
Orientation
Length
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Infinite Scroll

My Wife, My Boss, & I

by James Quiller on Sep 19, 2017
Loving Wives

Frank Ballwell, my boss and the managing partner in the law firm, and I had been working on the month-end reports for most of the day. It was now past 6:00 PM, neither of us had eaten dinner and it was obvious that there were at least a few hours work left. "Well, Jimmy, we're not going to finish the reports any time soon,'" he said "and I have an additiona...

Kelly's Thursday Night Frustartion

by Sashamy on Sep 25, 2017
Exhibitionist & Voyeur

It was Thursdays evening, Kelly had just returned from the gym. She had stripped off her shorts and sports bra pouring a glass of wine waiting for Gary to get home, he had already texted her saying he would be working late. It had been well over a week since Kelly had heard from Alex and was beginning to think he was done with her. She wanted to get out an...

How To Break the Literotica Toplist

by Tink4Fairy on Sep 11, 2017
How To

Have you ever wondered why some authors seem more popular than others? Why do some stories get so many views and votes, while others languish without the hope of a little red "H"? Why does it seem easier to get into the toplists in some categories but impossible in others? Is there some secret formula for writing a popular story? Yes, actually, there is—at...

A Captured Heart Ch. 03

by Queen_Vicki on Sep 12, 2017
Sci-Fi & Fantasy

As the glass shattered all around her Carmen was plummeting toward the ground, towards her death. She couldn't stop the smile that spread across her face as she felt sudden freedom at what she was about to experience. It seemed like an eternity as she fell towards her death, but right before she hit the ground her wings spread prideful and wide as she took...

Valerie

by WishFull on Sep 15, 2017
Erotic Couplings

She was little. She wore sandals and a natural linen sundress, short, with shoulder straps that were no more than strings. Around her neck was a narrow choker of lavender-colored velvet. Her name was Valerie. What had I done to deserve Valerie? Not a damn thing. At that cafe on a muggy afternoon in Amsterdam we just stared at each other, sipping wine. Momen...

Slut for All Pt. 01

by Knightofround on Sep 11, 2017
BDSM

"That's it baby! You are such an amazing cock sucker!" I moan around the cock in my mouth as I bob up and down quickly. I feel hands on the back of head grab my hair to stop me from moving up and down the amazing 10 inch cock. I've been kneeling for almost twenty minutes slowly working this monster. I've only been able to take just over half of the cock so f...

Damsel In Distress (3 & 4)

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Imagine your sister asking you to chaperone her on a date. Would you? Debatable - Now suppose you had to dress as her girlfriend? Duncan did but it was his sister who came to his rescue when subjected to a humiliating ordeal. This story can be misleading. It starts as an endearing sister, brother crossdressing scenario that develops into a humiliating and b...

Fantasy Fulfilled

by DevisPixi on Sep 13, 2017
Loving Wives

When Sue and I were first married we reveled in the fact that I was her only lover and she was a virgin when we first hooked up. After a couple of years and a couple of kids, she confessed to having a secret fantasy. "Two lovers," she pronounced. "I want to be the queen bee and mate with one of my males and then the other." I thought she meant role-play...

Barrack Room Betty Ch. 09

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Nine - Pink Pussycats All good things come to an end and the six-week Reduced Operations Period at HMS Chelmsford ended on 15th January 1974. The Wrens and Leading Recruits were very busy as that day approached. The Depot needed to be de-winterised and preparations made for the return of the Ship's Company, the recruits, and the Wrens from their l...

C'mon Blue

by redpilldad on Sep 13, 2017
Mature

This story had elements of two of my favorite things- softball and jiu-jitsu. If you've ever spent much time at the ballpark for travel ball or rec ball, some of this will be familiar to you. Be warned that some of the characters in this fictional story use racial epithets. If you don't like violence or interracial sex, do us both a favor and quit while you'...