Caught Sissy Stories

167,051 results
Orientation
Length
Source
Infinite Scroll

The Magdalene Academy

by TwistedPlayr on Sep 16, 2017
NonHuman

The Magdalene Academy was set far out in the countryside. It was free of distractions and had few neighbors and was the perfect place for a school of reform. The girls sent to this school were out of control and their parents had turned to the church for help. The girls were all daughters of rich socialites and nobles who had let their children get out of ha...

French Adventure Ch. 01

by Group-lover on Sep 17, 2017
Group Sex

He loved travelling and without doubt he also adored the whole feeling of freedom that enveloped him when he stepped out of his door and onto the start of a new adventure. The feeling was tempered by the sense of longing he started to experience, almost immediately, for his darling Suzie, but he knew that she was always behind him in his travels and that wha...

They Met at a Wedding

by 4uaw1 on Sep 17, 2017
Mature

They met at her father's wedding. Ann was dressed in white silk. White silk camisole, panties, socks even. The soft silk caressed her as she walked into the registry office. Her erect nipples felt every step and protruded out of the dress so while many in the congregation had their eyes on the bride, over half were centred on her chest. The tiara shone ine...

How I Became an Exhibitionist Ch. 01

by Midnight Hour on Sep 12, 2017
Exhibitionist & Voyeur

I first discovered exhibitionism in the basement of a bookstore. My brother, John, was browsing through the Film/TV section when I came up behind him and touched his arm. 'I'm done,' I told him. 'Are we going?' He looked up and smiled. 'Did you get what you wanted?' I held up the bag. In it was an Italian cookbook, with my promise to make John and his wi...

Study break

by watersex on Sep 12, 2017
Group Sex

Summer sessions were a grind. Three hours of classes each morning for six weeks were followed by more hours of studying before I waited tables at night. It was shaping up to be a summer with no fun. No fun for me, anyway. My kid sister Erica and her friends were having plenty of it, usually right outside my window. Of course, they were hardly kids, and tha...

House Rules

by Rodwarrior on Aug 30, 2017
Exhibitionist & Voyeur

This is a sequel to the story House Sitting Tuesday Mercy went over to lunch at Kelly's house, something that had been arranged for a couple of weeks. I got home from work around 4, and Mercy came back shortly after that. I asked Mercy about her day and she said she had been over at Kelly's all afternoon, but she kept changing the subject when I asked her a...

A View from Above

by romantic_soul on Sep 17, 2017
BDSM

As an author, I have always been interested in fantasies. These fantasies can crop up anywhere, anyplace, anytime. One of my stories emerged from a one-night stand with a man I barely knew, another from an erotic chat session with a man with a deep, dark dominating streak. But the idea for this story emerged from the recesses of my mind during an extremely u...

The Vacation

by Jeanttesome on Sep 17, 2017
Loving Wives

My wife and I finally decided to take the vacation we desperately needed. April and I had been working long hours and had seen very little of each other in the previous month, so we decided to spend a weekend away. It was February, close to Valentine's Day. We had once spent a few days in Henniker, New Hampshire, years earlier when we first met. We decided...

Amy's Spring Break Ch. 02

by IckyVicky on Sep 16, 2017
Sci-Fi & Fantasy

Author's Note: This is part II of my very first story on here. I hope you enjoy reading this as much as I enjoyed writing this. Any characters committing sexual acts are over 18. There will be more story available soon. Enjoy! This is a futanari story, by the way. ***** "Knock knock," I heard a familiar voice from my front door. "Shit!" I said, "Just a...

Stevie's Coming Out

by michaellajones on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 1 – Early Days I couldn't believe my luck, alone at last with weeks of fun time ahead of me now, my cock stirred at the thought as pictures filled my head , visions of silk and lace washed over my overactive young mind causing an eruption in my hand. The warm spurts of my cum soaked my eager fingers and seeped into the panties I had always been so c...