Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Cockland Island Pt. 02

by Sissyhalo1 on Dec 3, 2019
Transgender & Crossdressers

I knew I was messed up in the head and didn't care. I knew I was getting brainwashed but didn't care the videos, the drugs, the sex. These nice, big, muscular, handsome guys were there eating with us as we shared a table and were being really nice to Jill and I. In my normal life people are just sorta nice, not nice in this way. It was kind of cool and y...

A Natural Sissy Ch. 07

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a young woman turning an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will...

Miles's Conundrums Ch. 05

by justincbenedict on Sep 16, 2017
BDSM

It seemed like forever, standing in the corner. My dick still stung and my butt felt like ground beef. Gretchen seemed to have forgotten my existence. Staring into a corner is terribly boring, and I couldn't seem to entertain myself because I was in so much pain from the whipping. I assumed that Gretchen would eventually forgive me and invite me over for...

Steph's Descent Ch. 06

by 62_goo on Aug 31, 2017
Fetish

Steph decided that she wanted more tattoos. She talked to Fitz about it and he said he'd love to do them for her. She was undecided about what she wanted but Fitz said he had some ideas he'd like to try. Steph decided to trust him and become his canvas. Her next visit to his tattoo parlour resulted in two new tattoos, around the huge areolae on each breast....

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

The Perfect Choice

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to turn Andrew on, and it was working perfectly. She hadn't slep...

A Natural Sissy Ch. 04

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

It

by theonewhowas on Oct 14, 2017
Transsexuals & Crossdressers

"Hello? Yes hello, I've got an enquiry to make about tickets for the festival?" my master's voice rang out, as he shot me a smirk. I was on my knees in a latex French maid dress and stockings. My caged dicklette hung naked beneath me and I waited, patiently. The material clung to my body and I felt it tight on my chest as I breathed in heavy anticipation. "...

Thoughts on Cuckolding

by Youami on Apr 3, 2018
Reviews & Essays

Until a few years ago, I had only a vague understanding of the term "cuckold" as it related to sexual relations between couples. As ignorant as I was I thought it had something to do with cheating. However, thanks to the overwhelming number of cuckold stories contributed to Literotica, I have been able to build a better appreciation of this term and the many...

A Dickens of a Life

by CBruch on Jul 17, 2019
Interracial Love

'Best of times; worst of times', it was Charles Dickens who started off his epic tale of 'A Tale of Two Cities' with that phrase and I have often thought that should my life be written about then those few words would neatly sum up my biography. However, given my life is not yet done, such thoughts maybe a little premature and there might well be a happy e...