Training Sissy Stories

41,670 results
Orientation
Length
Source
Infinite Scroll

The Island: Caroline Pt. 02

by maddiebarry on Sep 13, 2017
BDSM

Author's Note: This is one of several short stories in a series called "The Island." All stories take place in the same secret island resort, where women come to serve as sex slaves for a year, under the control of a man known only as "Sir." All characters are over 18. All places, characters, and stories are completely fictional. Sexual slavery and human t...

Porno Theater Bang Bang Ch. 01

by Grandflasher C. on Sep 25, 2017
Erotic Couplings

"What's your name?" whispered a shy voice in the dark. The voice was young and feminine, which was very surprising. Doug responded back in a low voice, "What? My name's ... Doug..." But when Doug turned his head he froze. He had heard the voice but hadn't seen who was speaking. There was a stunning blonde next to him! She grinned back at him and left him...

Spritely Fellow Ch. 01

by DanteofSparda on Sep 14, 2017
Sci-Fi & Fantasy

Hello all, this is my first posting on this site after a long time reading. This is a story that will take some time to unfold and no sex happens until later in his life fyi. This current version is a test of some of this site's features that I will rerelease most likely when I go back over it. You are welcome to read it and post any major issues you see as...

After the Ball

by TinyBeth on Sep 12, 2017
BDSM

Author's note: This is a sequel to my Halloween contest entry story "Laine Goes to the Ball." While it is not necessary to read that story to read this one, it may increase your enjoyment of this story to read the earlier introduction to Laine and Xanna. Thank you to everyone that enjoyed the original and encouraged me to write the follow-up. I hope everyone...

Hostess with the Mostest Ch. 07

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Chapter Seven -- Pool Party Panic "You are more likely to die crossing the street than in an airline accident," Marjorie Deakin said. As usual she was dressed in her navy blue stewardesses uniform, legs clad in sheer black stockings and her feet shod in four-inch black patent leather high heels; her blonde hair and heavy makeup. "But we take safety seriou...

Opening Z Ch. 03

by polaris_flight on Sep 14, 2017
Group Sex

I heard a lot of the guys in the grand room watching pre-game. I saw no one on my way to my room. When I sat down on my bed and exhaled....that flush of awareness bounced thru me, got my balls roiling again. "Fuck yeah," I said to my reflection. I stripped and with one thought went to the showers: I wanted to show off...I stood in the shower toying, for a...

Mick Britton: Training missy Ch. 01

by Xantu on Sep 17, 2017
BDSM

Missy gives herself to Mick. Her training begins. Enjoy xantu Missy knelt on the thin exercise pad and put the clothes pin on her lips. It was ten minutes until 8:00 but she could not wait any longer. Just the knowledge that he was going to walk into the house soon had her trembling with excitement. It seemed like five weeks instead of just five days...

21st Century Subterranean Slavery Pt. 08

by Reavantwo on Sep 13, 2017
BDSM

Back in the lineup One-eight-six felt wild and untamed on her first day back in the lineup. She deliberately stumbled within the chain gang next to the board walk. She stopped now and then defiantly yanking the chain in front of her, forcing the slave behind her to crash into her back. When the guard lashed her she spat in her face leading to more lashes. B...

On the Shooting Range

by luvjuice43 on Sep 13, 2017
Erotic Couplings

Writer's Note: All characters in this story, or mentioned in this story, were over eighteen years of age. Events were based on actual experienced even though they may have been compressed for times sake and names may have been changed. Events occurred prior to the need to practice safe sex there fore no safe sex techniques were used. * After ten years of t...

Pearl Harbor

by theoldone on Sep 14, 2017
Erotic Couplings

The year was 1941 and there was a war going on in Europe and rumors that the Japanese might wage war on America. My name is John and I was raised on a cattle ranch out side of Valley Spring, Oklahoma. There was another ranch next to ours that was owned by Mr. Roberts next to ours. There were both big spreads but our houses were just about a quarter of a mile...