Toilet Sissy Stories

36,221 results
Orientation
Length
Source
Infinite Scroll

The Computerized Bed

by submissive~pet~ on Sep 14, 2017
Fetish

The year is 2020 all sorts of new inventions have been created. The time machine in which John Paul traveled was from the year 2002. He had no idea what was in store upon his arrival to the future. His machine carried him into a large bedroom. It was a very lovely room done in pinks and light blues. The bed was enormous in size, 4 times the size of any he...

Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...

Zoey's Basement Transformation Pt. 02

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

"Stand up," the whip crack of Mia's voice caused Zoey to flinch, but she didn't move from where she kneeled. With a sigh, Mia grabbed the leash attached to her chastity cage and started to give it a firm pull. Zoey quickly found her motivation, legs scrambling beneath her to find purchase. In her haste she slipped, almost falling back down. "Slower," Mia sa...

Sissy Slave Fantasy

by tinkerslut on Sep 13, 2017
Transsexuals & Crossdressers

A fantasy written to my mistress.. Sissy kneels before you, her eyes down, waiting on your pleasure. Sissy is wearing frilly panties with a matching bra, thigh high black lace stockings encase my legs. The red dress barely covers her smooth bottom. The high heel shoes, locked on my ankles, crossed behind me. I can't speak because of the ball gag in my mouth...

Like a Dream

by Scotsdude on Oct 15, 2017
Fetish

As I arrived at work that Monday, I knew that it would not be a normal day. My throbbing head was a distinct reminder of how my weekend had been. Saturday night was a blinder. It was my friend Kevin's 30th birthday, and as such, we decided to make it a bit of a blinder. It started out with paintball, went on to karting, dinner, and a strip club. Prague's st...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...