Sissy Panties Stories

160,213 results
Orientation
Length
Source
Infinite Scroll

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Another Submissive Slut Ch. 02

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I spent a tension filled week on edge. I was easily distracted from even the simplest of tasks as the memories of my adventures in the parking lot with Those People continued to haunt me. I fluctuated between arousal and disgust as visions of my performance played over in my dreams both waking and while a sleep. I had become nerve rattled, jumping at every s...

Caught in Her Panties Ch. 01

by Knightofround on Sep 12, 2017
Transsexuals & Crossdressers

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and p...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

The Training of Sissy Paula Ch. 2

by submissive~pet~ on Sep 14, 2017
Fetish

Mistress carolyn patted me on the head and said i did good. Then she sent me home. The chastity belt still on me, and the cucumber still in my bottom. I logged on line yet no e-mails from Mistress carolyn. It was 4 days before she sent me another e-mail. Hello my pet i bet you thought i had forgot about you. i replied with a yes Mistress i was be...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...

The Ex That Kept Me Pt. 01

by sissythongluv on Sep 14, 2017
Transsexuals & Crossdressers

She knew I loved to wear panties. She didn't know who long I had been wearing them, but she knew I did, and she had no problem with it. My ex-girlfriend, Kate, who had cheated on my numerous times, always with bigger cocks (which wasn't very difficult considering my tiny size), wanted to meet me at the mall. We had broken up, and she was dating some guy sh...

Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...