Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

College Cheerleaders in Pantyhose

by fanofpantyhose on Sep 25, 2017
Fetish

When my stepsister Kelly was a junior in college, she was involved in their cheerleading squad for a while. I sometimes went to the games and saw her and her classmates in these nice uniforms, short skirts, sexy legs and hot tennis shoes. But my fantasies went wild and crazy when I saw them wearing pantyhose or tights as well. One evening, Kelly brought 2 o...

She Had Sassed Him - Bad Idea

by diamondcat on Sep 19, 2017
BDSM

She knew she was in trouble before her hand reached from the door to the house. Her stomach quivered thinking of the tone in His voice when He had reprimanded her for her insolence. What had she been thinking to have been so lippy to Him? She felt dread roll in her belly at the thought of what would come. Thank God, He hadn't told her to cook. She would have...

Hailey's Journey Ch. 06

by nanmar on Sep 12, 2017
BDSM

Nick was back at the cage early next morning. Hailey was sleeping peacefully, at least as peacefully as she could within the restrictive bonds. Nick ruthlessly shook her awake. Looking into her dazed, groggy eyes, he said, "Do you really want another day like yesterday, Blondie? Because I can keep this up for a long time, you know." Hailey dumbly shook her...

Bad Day

by c24go4win on Sep 19, 2017
BDSM

He was waiting for her when she came through the door. She stood in the foyer dripping wet from the downpour she had just ran through to get into the house. "Where have you been," he barked. "You know very well I had to..." "I didn't ask for a long drawn out story," he interrupted. "You are late...Where were you?" She glanced in the dimly lit room and...

The Dark Room

by jimmy69 on Sep 16, 2017
BDSM

July received a note and it told her to go to an address across town. She started to get excited as she read it because she knew something interesting was going to happen to her there. She drove up to the house with the address from the note still in her hand. It was damp from anticipation. The house looked very quiet. July licked her lips with nervous anti...

She Wolf Ch. 02

by Kar626 on Sep 18, 2017
NonHuman

Thanks to Ladylana for being an awesome editor, and great friend. Here's the edited version of She Wolf 2. Comments and ratings welcome. *** I woke up in a dark room. Not a good sign. I noticed I was sleeping in a single bed, with white sheets. The room was a dark navy blue, and the only thing in there was a bed, doors to a closet, and a night table beside...

Date Night Ch. 03

by disgruntledmo on Sep 15, 2017
BDSM

We ate in companionable silence, his eyes feasting on my bare skin as I quickly shoveled chicken fried rice into my mouth. He finished his food much faster than I did, refilled his water, and proceeded to sit back in his chair, watching me. "What?" I asked, chopsticks halfway to my mouth. Rice fell off the sticks onto my plate as I looked at him nervously....

All Women are Bitches Ch. 07

by Samuelx on Sep 14, 2017
BDSM

Five o'clock. The magic hour. I can finally shed my disguise and resume my true form. By day, I work in an office building. I'm a lawyer and a damned good one at that. On top of being good at my job, I'm actually even pretty. I stand five feet ten inches tall, thick-bodied, wide-hipped and big-bottomed. But my face is gorgeously pretty. I'm a big, beautiful...

Breaking In Ch. 2

by Bhansai on Sep 17, 2017
BDSM

Eric took my arm and helped me out of the tub. "Now you are prepared to be broken in." I was led back to our bedroom and lain upon the mattress face down. My hands were placed over my head, my wrists bound together with velvet strips and then tied to what I assumed was the headboard. I couldn't be sure as I was still wearing the scarf over my eyes. "Tonigh...

The Step Daughter Ch. 04

by Charlie17 on Sep 19, 2017
BDSM

I drove out towards the suburbs with Jan curled up on the seat beside me, she looked almost childlike except for her incredible tits! "Pull your tits out of your dress, slut I want you to play with them," I commanded as I pulled her soft warm body closer to me. My little toy did as she was told without hesitation slipping her giant melons out of their confin...