Teen Sissy Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

Giuliana's Desires Pt. 01

by ValoryG on Nov 4, 2019
Transgender & Crossdressers

(All names and individuals are fictional) First of all, let me lay out the landscape. Giuliana Castelluccio is the heiress to an Italian maritime shipping fortune. Her grandfather and father built the Aegis Line from a few rusty transport vessels after World War II to the mammoth oil-carrying and container ships of today, and later launched the very succes...

Dress Modestly Ch. 02: Chance Meeting

by Maisy_P on Dec 2, 2019
Romance

It began slowly. The modest clothing concealed the very earliest changes. But all the wives could hear her sickness every morning. She grew pale, and the color left her lips. Her long dresses could not disguise a certain thickening around her hips, and a tightening in her bust line - the telltale signs of a newly bred wife. In spite of Anna's condition, th...

Frolicking on the Fifth Ch. 01

by Entrammeleur on Jan 22, 2020
Transgender & Crossdressers

This story follows the events of "Unleashed By Nair" and "Boned on the Fourth of July." *** The girl-on-girl action happening in my tub was a sudsy affair. A slender, leggy blonde traced soapy circles with her hands over the tight ass of a slim, fair-skinned, even longer-legged brunette. "Dammit, hon," said my wife, breaking my reverie, "you already had...

I'm Not Gay Pt. 01

by eroticwriter00 on Jan 20, 2020
First Time

My mother was born in Spain and my dad Canadian with a British heritage. They met at university and my mom introduced him to her and her family's naturist lifestyle. My mom was firm that her husband-to-be had to embrace naturism and that they would raise their children in that lifestyle. Initially, Dad was not thrilled, but mom had won his heart and he woul...

Agatha Allbut & The Bimbo Squad Ch. 11: Everyone Cums Together

by Salacious_Scribe on May 11, 2020
Erotic Couplings

© 2012 Sal De Klerk, All Rights Reserved Authors Note: This is a long story, containing 10 chapters a prologue and epilogue. All chapters have been submitted and should be posted within a few days of each other. The idea for this story came from a story idea forum. Thank you janetsexy77! Warning: This story contains interracial sex, group sex, lesbian s...

Last Week of School Pt. 03

by andrewmoocow on May 18, 2020
Exhibitionist & Voyeur

My name is Amber Martinez, a freshman student at J. Oscar University and a member of the nudist sorority Alpha Zeta Zeta. In my last account, me and two of my new friends Whitney & Dawn Quinn hung out with some cheerleaders that frequented a nearby nude beach. The morning after turned out to be my birthday on June 26th. To say I'm super-hyped wouldn't be s...

Volume 1, Nita Stories; Story #12

by PaleHubby43 on Jun 1, 2020
Exhibitionist & Voyeur

HOT PURSUIT It was another routine day, another routine patrol for Nita. This was a 'foot' assignment at Evergreen Mall, an upscale two-level complex in fashionable Woodbridge, Virginia. There wasn't much to do besides 'people watch'; and the shy, pretty young black officer would be surprised to know that almost just as much attention was being focused on H...

Molding Clay Ch. 04

by KalePond13 on Jun 9, 2020
BDSM

Clay could only struggle to remain upright after his release, his shaky hands now clenched at the front of both of the coach's thighs to support himself, his forehead resting slightly below the right side of Coach Dunc's hip. The kids breathing was labored and heavy, his face flushed a bright red beneath the layer of sweat that had formed during his unexpect...

Master Beckons

by LFFemdom on Jul 13, 2020
BDSM

You wake up in the morning with only one thought on your 19 year old mind, will he, will your master text you today? He's insanely sadistic, but exactly the way you like. Everything has been so crazy since you met him. But you yearn for his abuse and his touch. its then that you hear your phone ding. You grab your phone and open up the text, "I want to hurt...

Happy Neighbours

by romantictales on Sep 14, 2020
Fetish

Daniel dried the sweat off his face with the towel as he got down from the treadmill. He had completed the workout routine, which he had done regularly for the last couple of months, ever since the pandemic broke in and he was stuck in her apartment. He was pursuing his doctorate at the local university, and thankfully the university had gone online. They st...