Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Walk a Crooked Milf Ch. 03

by MicheleNylons on Nov 16, 2020
Transgender & Crossdressers

Chapter Three - Relax and Take What I Am Offering You Three weeks of agony... that's what Mrs Cashmore put me through. She didn't invite me over and she refused to see me or to answer my calls. Worse, she seemed to spend more time outside than usual, deliberately teasing me; dressed provocatively and ensuring that I saw her. She knew I was watching her and...

The Secret of the Island Pt. 01

by neoview on Sep 25, 2017
Transsexuals & Crossdressers

Hello, this is my first story I upload (not the first story I made). I am sure I didn't do a good job expressing my thoughts so please excuse me. You will notice the walls of dialogue and not so much "explaining". That's just my style but I hope to improve for the future. Anyway I expect some constructive criticism but please use simple words, I'm not stupid...

Opening Pandora's Box Ch. 07

by MiandEv2007 on Sep 16, 2017
Loving Wives

Note to the reader: I wanted to thank everyone for reading my story. I have received many comments and I appreciate both good and the constructive comments. I would like to address some of the comments directly. 1. During the course of this story and my previous one I have received comments concerning my grammar. I am the first to admit I did poorly in Eng...

Boston to Birmingham Ch. 02

by qhml1 on Sep 18, 2017
Loving Wives

Here it is, part two. No sex, a little action, and a lot of fleshing out of the main characters. You'll need this knowledge in the next chapters. ................................................ She stepped of the train, tired, miserable after a two day ride. The heat and humidity hit her like a physical slap. "Who the hell would voluntarily live here?"...

Lucian Ch. 07

by angiquesophie on Sep 14, 2017
Transsexuals & Crossdressers

A tremor crawled up his leg. It made his knees tremble before it disappeared under the flaring hem of his dress where it touched his bare cheek and danced up his spine - to choke his throat. "It's okay," a girl's voice whispered. *** October found its way to Norton's Academy of Excellence. It colored the leaves of the ancient trees before autumn wind...

The Last Boy Scout Ch. 03

by Tx Tall Tales on Sep 25, 2017
Group Sex

====================== Girlfriend decisions and campfire fun ====================== With my latest good deed out of the way, I decided to deal with some of my personal camp issues. I put my poncho back on, grabbed my blanket and headed for the drying shelter. Nobody seemed to mind when I moved a few things around, so I could hang up my blanket under cove...

Cynthia's Joy

by sinisterout on Sep 13, 2017
Transsexuals & Crossdressers

Many thanks to CKQuail for editorial input and proofreading. ***** In the beginning I knew her by her screen name, Goddess4u2serve. Later I learned her name was Cynthia, but I usually called her 'My Goddess'. She knew I was a cuckold before we'd even met. She'd read the stories I'd posted here on Literotica where I explored my dark fantasies. I can't e...

Cuckold in Training

by BBCXXX on Sep 24, 2018
Interracial Love

I was a stunned by my discovery! My husband Tony was out of town for a few days on business and I needed a tool from his workroom. While digging through one of the tool drawers I found a small, portable hard drive. "Why would this be in here?" I thought, but then the little voice inside my head started to scream, "Put it back you fool! Don't look inside; you...

Mike & Karen Ch. 05

by BiscuitHammer on Jun 19, 2018
Romance

Disclaimer: All characters are 18 years of age or older while actively engaging in sexual activity. This story is a prequel/sequel (sprequel?) to my other work, Alex & Alexa. Reviews are welcome; flames will be snickered at and deleted with extreme prejudice. Enjoy! Please Note: There are some incest themes with a secondary couple in this story. Just a...

Sadist, Masochist, Human

by NRMathis on Jun 26, 2018
Erotic Horror

Author's Note: This story contains content and themes that may be disturbing to some people, such as nonconsensual sex, violence, and mental illness. Reader discretion is advised. ***** In all honesty, the feeling of being captured was not nearly as bad as the feeling when I realized I had lost track of how long I'd been in their clutches. It marked the p...