Shemale Sissy Stories

7,624 results
Orientation
Length
Source
Infinite Scroll

Dawn's Shadow

by msnomer68 on Sep 12, 2017
Novels and Novellas

Chapter 1 "Here's to a new day," Chris said with a clank of the rim of her well-used diner coffee mug against her best friend, Anna's, equally battered cup. "A new day and a new me." She sighed heavily, as if saying it might actually make the words believable. She felt exactly the same on the inside as she had for the past month: empty, lonely, foolish for...

A Hunting We Shall Go: Wendel

by davebccanada on Apr 28, 2020
Novels and Novellas

CHAPTER ONE MIKE AND TRUDY "Michael, I've made up my mind! How long have we been sleeping together? It's over a year now and you've told me I'm your mistress since June. If Crystal is ever to have a brother or sister, if I'm ever to have more kids, and you know I want to, then we should start now. Don't you want to have a baby with me? I know we've been wa...

Pink Sugar Confidential

by onwardbob on Feb 3, 2020
Group Sex

Introduction This story got started when I lost this dumb Super Bowl bet to my friend, and occasional lover Murphy. So yippee, guess who got to be his sexual fantasy comes to life, for an entire weekend? Yeah, me Judi. And later, when I told another friend about a few of the more tasty parts of that sensational, practically unbelievable weekend, he suggeste...

Destinbury

by thornapple on Sep 19, 2017
Novels and Novellas

Philip Johnson Prologue An advisory to Literotica readers. This is a very long story involving photography for the first few chapters, and yes I do know that concept has been beat to death. I do hope that i've managed to give that idea a fresh treatment, and you'll stay with the story to see where things go. Good reading, Thornapple. Owen was forty one,...