Sissy Trap Stories

19,529 results
Orientation
Length
Source
Infinite Scroll

Types of Cuckolds

by cuckwhofucks on Sep 14, 2017
Reviews & Essays

What does it mean to be a cuckold? It actually means many different things to different cuckolds. But let's start at the beginning: The truth vs. the Truth. The Truth, or an absolute Truth, is actually unnamable, or rather it exists, but when you try to interpret it and put words to it, it becomes one of very many truths, as many truths as there are peopl...

Appointment by Card Only Ch. 03

by Sputnik57 on Sep 17, 2017
BDSM

Bruce panted in a mixture of fear, disbelief, and anticipation, his balls and anus tingling as he was gently tugged by the leash up the stairs; the beautiful mature form of the woman before him keeping his cock rock hard. Wicked smiles from passing madams and clients alike fell on the couple, but Bruce was oblivious to everything else but his superbly domina...

Solo Submission Pt. 02

by Subkoksukr4u on Sep 23, 2019
Fetish

Debbie watched the security camera display in amazement. She never suspected her husband would cheat on her but what he was doing right now was beyond her wildest dreams. She was at work in the teachers' lounge. Like most mornings she got to work early to prepare for the day and have a relaxing cup of tea. Dandelion root with Carmel and vanilla was her l...

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Busted Wearing Panties Ch. 02

by tonyl65 on Sep 18, 2017
Transsexuals & Crossdressers

I can't believe I am walking down the hall, wearing a black leather corset with matching panties, after my step daughter just fucked me in the ass with a dildo. I entered my bathroom, turned on the hot water in the shower, and slowly stripped out of my sexy clothes. I stepped into the shower and soaped my body down. I poured liquid soap in my hand and rubbe...

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

The Chastity Trap Ch. 02

by slavemalcom on Mar 13, 2018
BDSM

Malcom rushed back through town to his house, all he wanted to do was get to his room and see what could be done about the chastity device trapping his cock. As soon as he opened the door however, Emma came rushing out of her room and looked down from the top of the stairs. "Lott...Oh it's you." She said. She didn't even try to hide the disappointment and d...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Beauty and the Bully

by xaitonnar22 on Sep 13, 2017
Transsexuals & Crossdressers

The sun was high in the sky, yet a cool breeze blew over the busy metropolitan city of Kingston, California. The students at the local high school, Kingston High, were outside enjoying their half hour of lunch under the warmth of the sun high overhead. Jason Lane darted nervously between the buildings on his way to his next class. Most of the other student...