Sissy Wedding Stories

39,844 results
Orientation
Length
Source
Infinite Scroll

Mando & Lek

by Purple_Raihne on Sep 16, 2017
Romance

(I was writing this story when I was involved with two people. The three of us were the character basis. But they ended up committing to each other and forgetting I even exist, so I have no desire to bother trying to finish this story in the slightest. No names need to be changed as I already changed their names and Marie is my own middle name. To whomever d...

Anniversary Surprise

by patricia51 on Sep 14, 2017
Group Sex

(Note: If you haven't followed Sally from my other stories, well, don't worry. She's pretty self explanatory.) Sally was bored. The slender older ("40's something, if you please!") brunette glared around her hotel room as though it was the room disappointing her. She kicked off her flats and proceeded to scatter her gray business pants suit around the room....

Miss Khandie Ch. 03

by SweetNightingale on Sep 16, 2017
Transsexuals & Crossdressers

(Dear readers, sorry it's taken so long to post this next part, I'm busy with RL shit. Feed back welcome, please please please tell me what you think!) Xoxo Nightingale [1] Alright, so we all know that whatever happened between Frank and I...Will never happen again....right? I love Tanya, not Frank. I hope you all know that. We also know that we were ma...

Humiliation Slut Audition

by trenchantone on Aug 31, 2020
BDSM

It must have been a dozen years since I'd last seen Donna. Knowing that changes had come into my life in that time, I could only imagine how her life had changed. Looking around her waiting area, I had the sense that her architectural business was thriving; the room was nicely decorated. I was looking around because I was nervous. I was surprised when she a...

Where did My Damn Key Go Pt. 02

by PascalSage on Sep 24, 2019
BDSM

It didn't take me long to find something to wear. The lucky choice of attire was a sexy school girl's outfit I used to wear in a lot of my "private" encounters. It was complete with a blouse and plaid mini skirt. To make sure I was up to bitch's standards, I threw on some makeup here and there to give me a bit of an edge. A little bit of lipstick here, some...

Weekend in New Hampshire Pt. 03

by grant50 on Mar 2, 2020
Transgender & Crossdressers

Sam woke up and found that it was still dark. He needed a few minutes to figure out where he was and what he was doing. The first thing that he realized was that he wearing a nightie; then, that he was lying in bed next to his friend; and finally, that his friend had thoroughly fucked him a few hours ago. He actually thought for a minute that he had had some...

Reverse Evolution

by eviltwin52 on Mar 31, 2020
Loving Wives

Editor's Note: this submission contains raceplay and racial kink content. * I was programmed for it. From as far back as I can remember white men have been under attack. Schools, music, Hollywood, hell, even our own Government have proclaimed the evil white men are responsible for. They tell us how we're the root of the worlds problems. They decry our tox...

Meritocracy in Buttermilk Falls

by justincbenedict on Dec 25, 2019
BDSM

Learning to take his medicine seemed to be a bear for Ziebert. He tried so hard to hold back his gasps as Brahmin landed the saucepan again and again on his bare buttocks. She'd started Ziebert on hairbrushes and wooden paddles, and then the heel of her Capezios. A metal saucepan seemed to be what a "real man" needed, as she often sarcastically commented...

Cindy's Recourse Pt. 02

by TeroWright on Sep 14, 2020
Fetish

"Not a one thanks to you two," Gracelyn says. Ariel smiles down at Echo as she walks past her and towards the only conscious guy at the moment. "Well, well...Bravo is it?" Tapping her foot on his hip, "How they hangin'?" "I think you broke something," he wheezes on the brink of tears while laying sideways in the fetal position. "It wasn't my shot that hit...

Surrender Ch. 12

by Ada Stuart on Sep 19, 2017
Sci-Fi & Fantasy

A few days later the world seemed to have tipped upside down, Morgan thought. Jack Kelley and some of his most trusted men had been released and had now long meetings with Connor, Master Kane and some of the council members. Rumours had it that the rebels dictated several reforms that would be put into action soon, and more rebels were released on a daily ba...