Sissy Thong Stories

50,082 results
Orientation
Length
Source
Infinite Scroll

Mistress In Control

by polishjoe on Sep 17, 2017
BDSM

Last Friday evening when I got home Mistress informed me that tonight was going to be a very hot night but I did not realize until later just how hot things were going to get. Mistress had dinner ready and she told me she wanted us to eat quickly so we could get straight to the "activities" she had planned. I thought it curious because Mistress usually did...

Discovered At the Gym Ch. 01

by richysissy34 on Sep 13, 2017
Transsexuals & Crossdressers

A quick backstory, I am an 21 year old college kid, about 5 foot 6, who just recently joined a gym to try and overcome my smaller frame and slim feminine body. I have a secret love for wearing women's clothes, especially lingerie under my male clothes as much as possible. I have no issues with getting women, the occasional hook up and girlfriend from time to...

Sabbatical or Continuous Gang Bang?

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My parents were fine with fine me taking a short break but adam...

A Jamaican Vacation Ch. 04

by sissyashley4bbc on Dec 24, 2019
Transgender & Crossdressers

Rebecca studied me up and down. "What happened to you?" She asked. "I...uh...I..." Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you." "Make it a double," she said as Ty started to make her a screwdriver. He handed her the drink, grabbed a joint, and ushered us outside. Rebecca sat down...

The Dominatrix Order Pt. 02 Ch. 04

by Jwwsmith on Feb 11, 2019
Transgender & Crossdressers

Protestors swarmed the streets of Femininus on what was the anniversary of the initial passing of the 23rd Law. It had recently been considered for repeal and been upheld by the Council of Goddesses. The protestors demanded that the 23rd Law be repealed and that same sex courtship be legalized. The predominantly liberal crowd congregated before the steps of...

Back-alley Sissy Boy

by Travel_by_day on Sep 12, 2017
Fetish

I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong. I was so turned on, my cock started to get rigid right away. If I had been wearin...

Alex, The Closet Sissy

by Areallysissyboy on Feb 11, 2019
Transgender & Crossdressers

My name is Alex, a closet crossdresser. 18 years old, never had a date. Too skinny, too weird, too feminine. I wore my hair long but not a hair on my body tho, not very athletic. Just a 5'3" skinny 125lb pale white boy with long black hair. Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsuperv...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...