Sissy School — Len Is Caught Wearing Panties And Sent To Sissy School Stories

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One Step Too Far

by SatinDreamGirl on Sep 16, 2017
Fetish

The clock on the bedside table clicked loudly in the otherwise quiet room. A soft buzz of cicadas outside drifted in through the small gap in the raised window. The room seemed to glow with pink from the afternoon sun. The room hadn't changed much since Rachel had begun her fashion phase in high school. Her closet (and the closet of the guest room) were stu...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

A Wild Widow and Widower Ch. 07

by ljprockhard on Apr 22, 2019
BDSM

Editor's note: this story contains scenes of incest or incest content. ***** Participants (all based on people known to the author. Names have been changed and ages have been altered to fit the scenarios.) Len – 64 – widowed 3 years ago (traffic accident) Tammi – Len calls her "T" – 56 - Len's next door neighbor – widowed 18 months ago (pancreatic cancer...

We Worked Together

by bedolson on Jul 11, 2018
Erotic Couplings

We worked together at a publishing company but not in the same departments. Len did maintenance at my job; I was a graphic artist. He was a long hair heavy metal guy, me, a short haired punk rocker. We were both married and had children that were the same age. He was also my weed connection. After my marriage ended, my relationship with Len continued. One...

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...

Jesse's Journey Down a Rabbit Hole Ch. 04

by sadkins116 on Sep 19, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to th...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...

A Tale of Two Bitches

by Lordheed on Sep 12, 2017
BDSM

"Game Over", a deep voice pronounced from the television. Johnny threw down the controller in frustration. 'Can't even win at video games, let alone anything else', he thought to himself in disgust, 'What a way to start winter break'. He'd been home now for 3 days; already missed campus, his dorm room, and the constant business of schoolwork that could keep...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...