Sissy Dare Stories

47,304 results
Orientation
Length
Source
Infinite Scroll

The Last Range War

by Egmont0409 on Aug 31, 2017
Humor & Satire

A SATIRE, perhaps historically incorrect in places. INTRODUCTION In 1912 a rancher's son Lee Stanton, aged twenty-two who was heading home after failing final exams to qualify as a pastor, unintentionally started an escalating feud between the Stanton and Murphy families that probably was the last of the range wars. You won't find it in history books beca...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Another Submissive Slut Ch. 06

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

As I stared transfixed as Ms Shawna rose off of Mr Lennie's drug rigid cock. His dick was shiny slick with a mixture of their cum, the goo thick about the folds of Her twat. "Oh god Lennie," She gasped breathlessly, "where do You get all Your beautiful cum from." I groaned involuntarily as a cum gushed from within Her to slip down Her inner thigh, while Mr...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

Meeting your Goddess

by theroomman on Mar 7, 2018
BDSM

I showed up to the bar late, I knew keeping you waiting would have you wondering if I'd show up at all. You get so excited when you see me. There's no question I'm the girl you were waiting for, my dominance is overt: dark lipstick, high heels, and a tight revealing black corset style dress. Before you can even say hello, I shush you with a finger on your li...

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

Outed and Married Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

When I entered the room with their drinks on the tray I was carrying I thought I would be pleasing to my husband. I made sure that my skirt was properly adjusted the way he likes me to wear skirts in the house. He insists that my rear not be covered below my tight little hole, insists that he have instant access to it if he wants to use it for his pleasure....

Sissy Shopping with Princess T

by Subboi23 on Apr 1, 2020
Fetish

I excitedly pull my tight red lacy panties up over my small, limp penis. They feel so nice. Tight, but soft, containing the perfect amount of room to hold my little package. My penis does not attempt to get hard despite the pleasure, if anything it seems to shrink a bit in order to fit more comfortably. This was my first time seeing Princess T without her in...