Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

Midnight Caller

by scarlet_letter87 on Sep 14, 2017
BDSM

After yet another unfulfilling night at Perry's, I came home to try to sleep. I wasn't horny and not generally in the mood for any shenanigans. So when Kenneth messaged me, I tried to dissuade him. I like Kenneth, but there's never any intercourse so our encounters always end with his cum going down my throat. Which is by no means a bad thing, I just wasn't...

The Wait

by Grayeyedsub2 on Sep 15, 2017
BDSM

Ginna cried out thrashing her wrist in the cuff wanting and needing it off. Kull left her attached to it in the middle of the room with a bucket to use to pee in also to drink to quench her thirst. Her wrist is throbbing with pain and bruises are forming all over from where she was hurting herself trying to get free. She sits back against the wall head hung...

Linda's Runaway Adventure with the Band

by Johnsexlife on Sep 1, 2017
Group Sex

Linda was the oldest of four siblings living in a small cottage just outside of Seattle. Life was not good as her mother and father were physically and mentally abusive. She can remember at 6 years old when she had to open a can of Crisco so she and her sister could eat it (yuk). Her mother was always having affairs and often forgot to feed her children. He...

A Dream?

by twistedz13 on Sep 17, 2017
BDSM

You stood there silently watching me, eyes blazing with desire. I could already feel my pussy twitching with want. Not having the patience to wait a moment longer, I grab a small whip from the wall and said "Please" in the most naughty sweet voice. "Get up!" you barked as my body jerked a small, red splotch formed on the curve of my butt cheek just beneath...

Temptation's Curse Ch. 02

by RiannaTyler on Sep 17, 2017
Mature

"Damn it!" Scott shouted out loud in his empty office. He cursed himself silently for going back to the admissions office yet again; Cursed himself for being a glutton for punishment. He knew Erika wasn't going to speak to him, knew he had crossed a line with her that she could never forgive. And yet for the last week he managed to find an excuse every day t...

I Couldn't Say No

by JimandGarysgirl on Sep 16, 2017
Interracial Love

I wanted Jim and I wanted him now. There were times that he teased me into thinking he wanted me and then he would send me on my way. At first I got upset and angry, but then I was so happy he got me to cum on fingers and go to bed having dreams and images of what it would be like to have him fuck me. Five years it will be in May and I will never be able to...

Somali Lesbians Of Ottawa Rule!

by Samuelx on Sep 15, 2017
Interracial Love

Is there anything sweeter than a submissive turning the tables on her own dominatrix? That's the question I asked myself as my lover/submissive Kimberly Kellerman dominated the shit out of me. You're my bitch now, the tall, sexy blonde chick from Toronto taunted me as she worked her fist into my pussy as her butt plug went deeper into my asshole. My name is...

Contracts - Get One!

by psychiclover on Sep 1, 2017
How To

If you are reading this you are interested in a pursuing a BDSM Relationship. This article is about one of the most basic things that should be considered before deciding to get into the lifestyle. Yes, you saw it right lifestyle, not just kinky once in awhile sex. So there are greater expectations here. Making a contract is something you most definitely sho...

A Beginner's Guide to Bondage

by Somegirl on Sep 18, 2017
How To

Introduction Many people fantasize about being controlling or about being controlled, and (in most cases) this is a healthy fantasy. While you can always do this in daily life the bedroom is a good place to live out those desires. People who wish to be in control are usually referred to as the dominant, or the Dom, for short. People who wish to be control...

Blood in the Big Easy Ch. 00

by EMJohansson on Sep 16, 2017
NonHuman

**Authors Note: Welcome to my first foray into the world of writing. This story will start off slow, as in limited sex scenes for a while, sorry :). The intent is to build the characters and storyline. To those of you who are history buffs, especially in the realm of Greek Mythology, I ask for your forgiveness. You might see a few tweaks to time, age, locati...