Sissy Bra Stories

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Infinite Scroll

Veronica in Japan

by v3r0n1ca on Sep 16, 2017
Interracial Love

The elevator grumbled to a stop on the 5th floor and the doors slid open and Veronica stepped out into a poorly lit waiting area. She was wearing a shiny sequined cocktail gown favoured by the working girls in these establishments that was struggling to contain her figure. Her legs were bare as were her shoulders and her hair was done up in an elegant French...

My Best Friends Ch. 03

by Dark_Rose90 on Sep 16, 2017
Transsexuals & Crossdressers

~ Author's Note: Ch. 01 and 02 were based entirely on true events from my own life with names of the people involved, including my own, changed for privacy reasons. Every chapter from this one forward will be a mixture of true events and fantasy experiences. Enjoy!! ~ * I woke up the next morning from a dream different than any other I had ever had. I was...

Interview Time

by wildsweetone on Sep 13, 2017
BDSM

The advert read: Maid wanted. Normal household chores, including cooking. Must be able to work under pressure, to follow orders exactly and without question. To apply, phone Jake 444... Well, I'd phoned, answered a few curt questions and was told to come to this address. I was standing, looking at the imposing entranceway now. Am I doing the right thing? I...

A Couple's Voyage Into Sexuality Ch. 04

by fntsymn on Sep 12, 2017
Exhibitionist & Voyeur

Robert and Vanessa arrived at Edward's and Pamela's house around 10am so they would have ample time to shoot the video. Edward and Pamela greeted them at the door and they exchanged their usual kisses on the cheek. Pamela and Vanessa went to the kitchen to get some coffee while Edward and Robert talked about where to set up the camera on the tripod. They re...

Two's Company, Three's a Party

by KeikoAlvarez on Sep 14, 2017
First Time

It was the last leg of my business trip, a trip in which my company pinched every penny they could. So, instead of booking me on a nonstop from San Diego to New York, they booked me on a flight that stopped in Chicago to save fifty dollars. Fifty crummy dollars! To make matters worse, I was wearing a navy blue silk dress with a nice slit up the side, a slit...

Nice Guys Finish Last

by nameuser on Aug 18, 2017
First Time

Science class at the end of the day was always a time of near-anarchy for me. The students were loud and annoying, but I and one other girl were quiet- I because I was shy, her because she didn't give a thing for the class (not to mention the teacher was a flat chest and hated to be reminded so). As such, I sat in the far corner of the classroom, and she nex...

Just the Begining

by outrabutterfly on Aug 31, 2017
Erotic Couplings

Caytlyn had known Nick for years. Five years to be exact. They had met through the Internet and realized that they both attended the same college. She was in her first year, he had graduated the previous spring, yet still came to campus to visit friends. They talked for weeks before meeting and when they did, both felt an instant connection. To make a long s...

That New Guy Ch. 06

by Irish Moss on Sep 13, 2017
Erotic Couplings

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venom...

Roadside Work

by NightWriter91 on Sep 16, 2017
Toys & Masturbation

I always get horny when I drive long distances. With over 100 miles of straight highway, I can't help but think about my orgasm. It's bad enough when I'm just sitting in class, daydreaming, but I'm especially bored driving back home for breaks. Something about the car bumping along, my hips spread slightly as I sit up, rocking into the movements. I've mastur...

Almost Heaven Ch. 02

by 99_percent_oral on Sep 13, 2017
Loving Wives

Jeanne met her second husband after a Board of Education meeting. Normally, she wouldn't attend them but she sometimes went just to see how much bullshit members could cover without once talking about what happened inside a classroom. As usual, they didn't disappoint. Joe was a newly elected member and Jeanne taught history in the high school. At the time s...