Teen Sissy Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

Discovering Amber Ch. 05

by Ms_Allison on Dec 24, 2018
Transgender & Crossdressers

Mistress notes: To say both amber and Jenn were surprised when Jenn entered my condo would be an understatement. I had given Jenn "some" warning as to what she might find, but she was expecting me to be dressed up for her not amber. Poor amber had the biggest crush and attraction toward Jenn as well, it was hard not to though, Jenn is gorgeous! It was time...

An Aussie Teen Romance

by cbrguy on Jul 14, 2020
Romance

Declan O'Reilly's teen years had always been miserable, with bullies seeming to line up to taunt him. Sure he never liked sports or "blokey" stuff like most other boys did but no-one else seemed to cop as much shit as Declan did. Even one of his former high-school teachers had called him a sissy, not once but twice. Declan was a grimly shy 15-year-old boy w...

Caught in Her Panties Ch. 03

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

As we walk down the street I wink at some of the men walking past us. Alex and Mary giggle as they see the men checking me out. I even smile at the women too. "You are such a tease Krystal!" Alex says noticing some of the women blush as I check them out. We find a nice sidewalk coffee shop and take out seats. As I sit, I feel someone smack my ass. I jump a...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Xander’s Nocturnal Adventure

by neverless on Sep 13, 2017
Celebrities & Fan Fiction

I do not own BtVS or, its characters, they belong to others. I am not making any money from this story. All the characters are over eighteen. * Eighteen year old Xander Harris looked in the mirror. He looked beautiful, with his make-up and his hair curled he looked, if not like a young lady, at least close enough to be mistaken in low light and at a dista...

Outed and Married Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

The head of his cock pushes hard against the back of my throat. I struggle not to gag. I struggle to control my gag reflex. I feel my throat spread open as he pushes his erection all the way into me, pushes deep into my mouth. It never gets easier no matter how many times he's done this to me. I feel that brief flash of slight pain as he deep-throats me. Fro...

Wan Wan Wan!

by Frocto on Sep 16, 2017
Interracial Love

-The following story contains heavy race play. I do not personally bear any ill will towards the Korean race, or any race for that matter. Please enjoy this as a work of fiction!- "Good little Hyuna," said her producer, smiling down at the Korean idol. His penis was stiff as a board in his pants. "Hyuna good girl." "Very good. Very dumb and obedient, like...

Ballet Erection

by pixiemuledonkey on Sep 14, 2020
Fetish

Author's Note: Long ago, I roleplayed a play-by-post erotic fantasy with a girl named Christine, who amazed me with her deviously humiliating responses. What follows is a reconstruction of the scenario we roleplayed, which has ever since remained a favorite erotic fantasy. Wherever you are now, Christine, i hope you're enjoying powerful orgasms! You gave thi...

Falling into Being a Sissy

by Sissyhalo on Dec 12, 2018
Transgender & Crossdressers

My name's Sonny and well life's been pretty damned golden for me. I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me. Middle classed family, decent money for all of that, lots of high school pussy and even more in college. Being a jock in college doesn't prepare you for...