Hairbrush Stories

2,670 results
Orientation
Length
Source
Infinite Scroll

Corporate Training - Day 02

by Redandmore on Oct 31, 2017
BDSM

Allison meets with Miss Carla, her Disciplinarian, for a second "training " session. The young Engineer finds out more about herself and her desires. Allison unknowingly meets her Accountability Partner. DISCLAIMER: This is a Fantasy work that in no way reflects real workplace situations or practices. All Characters over 18 years. Please view the Tags to d...

Mother-in-Law is Disciplined Ch. 03

by tom6432 on Sep 18, 2017
Fetish

(This story is fantasy written by me for fun. It contains spanking and humiliation. Please do not read if this bothers you. All characters are 18 or older) Both of my young ladies sat in the back of the car with raised skirts, with both sets of panties down to their knees as they sat on the cool leather seats. They were wearing their punishment outfit, w...

Long & Hard

by Joseki Ko on Sep 12, 2017
BDSM

Authors note. This is a readers request. I hopeyou enjoy it. Long and Hard It was early afternoon and a very warm day, yet I was shivering. A slight chill went up and down my spine every time I glanced at Mike sitting as his computer. Bits and pieces of the previous night’s events and the conversation we had that morning crept into my mind over and over...

A Girl Named Zoe Ch. 02

by YourLittleGirl9 on Sep 1, 2017
Group Sex

The suddenness of these little birds flying over to me was a real surprise. I was mesmerized watching the two of you together, drinking in your naked bodies in the dark, just shadows, your white skin illuminated now and again by the lights shining in through the windows and an occasional headlight passing us. But fly over you both did, and your first activ...

Janet Owns Me Now Ch. 04

by trissy1 on Sep 16, 2017
Transsexuals & Crossdressers

Reluctantly, i started down the stairs holding the oval wooden hairbrush that i already had a love/hate relationship with. The pink charmeuse slip was tight and short and rode up as i slowly descended the stairs. At the bottom, i tugged it down and took several deep, shaky breaths trying to calm myself. i felt so foolish dressed like this, but also oddly cal...

53 Minutes

by Sunshinesnaughty on Mar 9, 2020
BDSM

"Well, this is new," thought Sunshine. He didn't sound like His usual cheerful, playful self at all. He seemed very focused and all about the business. Looking back, Sunshine couldn't think of anything she had done wrong. She took pride in being an obedient, well trained submissive. He had been clear with His instructions. She was not to say a word during t...

Secrets at the School Gate

by EddieEnglish on Apr 28, 2020
BDSM

Laura parked her car and made her way to the school gate for pick-up time. For once she had found a parking space easily and wasn't late. She was also glad to see her friend Chrissie already there, which meant there was time for a chat before the doors opened and a horde of youngsters surged out. The school mums could be a cliquey lot but Laura was glad to h...

The Estimate Ch. 02

by daddyspanks61 on Sep 17, 2017
BDSM

Her soft ass cheeks, first one, and then the other. "Tell me why you're getting a spanking" I said. "Cause I was doin' a naughty thing, " she lisped. "What kind of naughty thing were you doing? Show Daddy what you were doing." She whimpered, " But Daaaaa-deeee, do I haaave to?" Without answering, I slapped her ass cheeks suddenly and forcefully, twice o...

Minnie and the Newlyweds Ch. 06

by Alfamann on Sep 16, 2017
Fetish

For Peter and Angie each evening was now full of anticipation. As the evening progressed they could feel themselves becoming excited by what was going to happen. The unpredictability of what they would encounter was an intoxicating mix of dread, humiliation and anticipation. Each night after showering they would fetch the hairbrush then present themselves t...

Hand Job Slut Ch. 03

by Carnevil9 on Sep 19, 2017
Fetish

Chapter 3: The Hunger Nancy was "riding the hairbrush." That's what she called it. She was lying on her bed, naked, on her back. Her feet were flat on the sheets, with her knees up and spread wide. Her right hand was holding on to the bristles of her plastic hair brush, with the round, ridged handled jammed deep into her pussy. She needed the stimulation t...