Spanking Sissy Stories

28,144 results
Orientation
Length
Source
Infinite Scroll

Coach Daddy Ch. 07

by whatcouldofbeen on Sep 25, 2017
Transsexuals & Crossdressers

It has been several glorious weeks since my gender and in essence , my life, changed. Who was once an awkward bean pole of a young man, was now a confident budding woman. It all started when my boss, Coach Zek, noticed my preoccupation with all the huge men I was now constantly surrounded by. He also noticed that I wore a bra. I'm sure at first he thought I...

Casey Blossoms

by jackie_em on Feb 7, 2018
Transsexuals & Crossdressers

As I grew up, I knew I wasn't a guy – not a normal guy anyhow. The normal boys liked doing rough things, fighting, playing war, playing sports, watching sports, hunting, fishing, all those male things. I didn't like any of that. On the other hand, I never wanted to be thought of as a sissy. I went through some of that, so I hung out with the boys and did jus...

Rosie Finally Meets Jessica

by DoesAnyNameWorkOnHere on Aug 6, 2019
Transgender & Crossdressers

It was cold. Bitter cold. January always brought negative temperatures and more snow than I care to see. It's the kind of cold that gets into your bones and you can feel it for hours after being in a warm place. Not even a hot shower can soothe the chill you have inside. Short days and long nights made the month long and depressing. My only respite from the...

Moment of Truth

by sharkinlace on Sep 25, 2017
Transsexuals & Crossdressers

So...my life has pretty much come down to this. I came home from work to see that my wife had bought a new skirt. She had tried it on and was modeling it for herself in the mirror. She looked great. The skirt nicely accentuated her sexy curves. And judging by her reaction to her image in the mirror she really liked it. But the first thought that popped into...

Mistress Barbara Calls Ch. 03

by goamz86 on Sep 19, 2017
BDSM

Letter to the reader: This is a story of female domination of a submissive couple. It includes the man sucking dildos and taking thinks up the ass. If this is not your cup-o-tea, please find another story. Don't waste your time and mine reading it and making comments about me being a fagot or other asinine remarks, I will just delete them. Constructive comm...

Also

by PTBzzzz on Sep 16, 2017
Loving Wives

There are places in this story where the same person is referred to as Missy, Mrs. Smith or Also. Please understand the names are to give the perspective of the person viewing her. There is no overt sex. If you are looking for a cheap thrill you will not find it in my stories. Hank Williams Jr stated once that he writes songs about subjects he knows. I wri...

Jesse's Journey Down a Rabbit Hole Ch. 19

by sadkins116 on Sep 15, 2017
Illustrated

Jesse and Marcus tried to sleep, it was difficult with the ball and chain still attached to their butt plugs. They would drift off to sleep but then wake with a shock whenever they moved. The balls were heavy and slippery, weighing almost twenty pounds. The stainless steel finish was polished with a thin coating of something very slippery, like Vaseline. Whe...

The Massage Away Ch. 03 Pt. 07-08

by formyqueenspleasure on Sep 5, 2018
Fetish

As always, the preceding chapters set the stage. This story could have been in so many categories. If Femdom, Interracial, Cross Dressing and now Group sex involving one's wife offends you, sorry. To everyone else, I hope you enjoy, comment and vote * Chapter 4 Part 7 After my Queen and Master had left the room to clean up and prepare themselves for the...

You're Like a Little Boy at Times Ch. 01

by Myneed on Sep 13, 2017
Fetish

This is a femdom love story that will only make sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18 Chapter 1 One early Summer weekend, I was hanging out with Mel an Tim in their loft. I have lived in a loft myself, an old warehouse space by th...

Remaking a Boyfriend Pt. 06: The Big Decision

by her_every_command on Dec 3, 2019
Transgender & Crossdressers

The next day, Sunday, was much more relaxed. Ray again got dressed up in an outfit of Allison's choosing, this time a pencil skirt and blouse. Allison had him do some of his own makeup as he continued to learn how to apply everything. They went to brunch, where the waiter flirted shamelessly with them and gave them a free round of drinks. Ray tried out his g...