Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Riding the Boss Another Day

by Brian70 on Mar 6, 2018
Transsexuals & Crossdressers

The second time that I met Nick was last Friday. The week at work following that weekend sucked. Seriously it was awful. True to himself he was the same incompetent manager as before. Same as the entire time I worked for him before the first time our paths crossed at the ABS. I couldn't stand him. There had been some euphoria that took over my consciousness...

Public Cross Dressing Experience Ch. 01

by sublocked on Sep 13, 2017
Transsexuals & Crossdressers

Don stirred in the hotel bed. He was uncomfortable, and he was unsure why. His head was pounding to the beat of his heart. He pulled his knees up toward his chest to try to squeeze into a sleepy fetal position. It was then that he realized something was very different here. He felt compressed and restricted. He was lying in a bed, but what bed? It wasn't his...

Tits Have Benefits

by hottchic on Sep 25, 2017
Transsexuals & Crossdressers

I thought that I would try to write an erotic story with a transgender theme as I have been a cross dresser for a long time. This is my first attempt at an erotic story with a transgender theme although it is not the first erotic literature I have written. I hope you like it, and let me know if you want to see more of the same. So here goes... * So there I...

Faith Debased Ch. 6

by JordonLynn on Sep 19, 2017
Interracial Love

Author's Comments I was recently called to task for a faux pas I made in chapter 4 concerning a woman's specific anatomy when I described Faith enviously watching Regina's Adam's Apple bob as she swallowed the majority of Cal's hot load. Now, being able to run my hand down my own throat, I am well aware of the fact that a woman does not possess this particul...

Crystal: A Sissy Set Free Pt. 02

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

Direct continuation from Part 1, if you haven't read that go read it, things will make a lot more sense. ***** He walked over to Amanda's large bed placed his hands on the soft sheets and bent forwards exposing his bum to Amanda who had donned a pair of rubber gloves and grabbed some lube. She walked closer until she was right behind him; she crouched and...

Joshua Learns His Lesson

by Amary on Sep 12, 2017
Fetish

Disclaimer: This story contains elements of CFNM (clothed female naked male), humiliation and femdom. It is not intended to portray real life or real people – the situations are too over the top for that. The setting is the fictional King Arthur Comprehensive School in 1920s England. King George V is on the throne and the British Empire is at its peak. The s...

Bayonetta's Abuse Ch. 02

by ChainedToAKeyboard on Sep 13, 2017
Transsexuals & Crossdressers

Bayonetta has a rather unusual fetish and her slave is going to learn all about it whether he wants to or not. Bayonetta's Abuse II - Cereza's Curious Kink The green foliage sped by as Bayonetta pressed down firmly on the accelerator of her Noble M12 GTO. It was a warm spring day and James, sitting in the passenger seat beside her, was basking in the sun...

Questions That I Don't Have Answers

by SusanJillParker on Sep 16, 2017
Humor & Satire

SusanJillParker has lots of questions but no answers. Help. I need help. Being that there are lots of wicked smart and/or educated people who read the sexy stories posted on Literotica, I need your help. I need answers. I have lots of questions that I don't have the answers. In search of answers, I need answers. With all of these unanswered questions hurti...

Darlene's Story Ch. 3

by Greg Lee Hunt on Sep 17, 2017
Fetish

Part III- Mistress Darlene ( In Chapter 3, Darlene completes her transformation from a grossly overweight undersexed wife into an alluring and svelte dominatrix who is served and serviced by a group of submissive males. She contrives a plan that will reveal her secrets to her friends Abby and Pamela and subsequently recruit them into the world of female dom...

Spanked by His Neighbor

by rickiee_2002 on Sep 13, 2017
BDSM

PREFACE I am a 53 year old man. I am six feet tall and in good shape. I watch my diet, and I try to work out when I have the time. I have a daughter who is 26 years old from a prior marriage. The mother of my daughter died when she was an infant. For the first 16 years of her life, I was both her mother and father. I did the laundry. I cooked the meals and...