Headmaster Punishment Stories

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Cheap Sissy Whore To Call Girl Ch. 02

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

The day I woke up after being knocked out was a strange one. I didn't know how long I had been missing but I felt my body had been completely transformed. My skin felt softer, I had breasts, my lips were filled with collagen. I remember waking up in a what seemed like a hospital room and walking up to a mirror and looking at a gorgeous bald woman with a peni...

Further Adventures of Susan Adams Ch. 07

by SteveLee1146 on Sep 14, 2017
BDSM

THE FURTHER ADVENTURES OF SUSAN ADAMS 7 As the picture ended, all three were silent for a few moments, but the air was electric, as if in anticipation of a storm. Suddenly, Jean blurted out, "Please, Don, I can explain!" Don's reply, while mild in volume, carried such menace that both women froze for a moment, and, as Jean cowered back against the pillow...

Sara's School Punishment

by MissChristine on Sep 13, 2017
BDSM

It was a crisp early fall day, as Sara walked across campus on the first day of class. Sara, a second year economics major, had been looking forward to the start of the fall term all summer. Unlike many of her classmates who spent their weekends drinking or partying, Sara was a very dedicated student, and spent most of her time studying or researching. Sara'...

My Cock is Yours...and Yours! Ch. 02

by MyCockIsYours on Aug 30, 2017
Group Sex

The first thing I noticed when I awoke was the darkness. It's pitch black in the room. The second thing I noticed was that my wrists and ankles were bound to the bedposts. Now I remember the last thing you told me before I drifted off to sleep after an exhausting three-way with your secretary. You said that you and Lauren were going shopping and that I woul...

Fuck Cow

by DanceOfDeath on Sep 19, 2017
BDSM

"He asked me to marry him today," she mumbled as my cock hit the back of her throat. "Did you accept?" "Yes," she replied as I unleashed my cum into the back of her throat with a satisfied moan. Immediately she fell back to her knees, placed her hands behind her back and tentatively licked the remnants of cum from my wilting member. "How may your worthl...

Submissive Training Pt. 01

by youarehisvessel on Sep 11, 2017
Exhibitionist & Voyeur

She walked into the kitchen. She had listened well. She wore a loose top and no bra as I had instructed. Her tits were generous and jiggled slightly as she moved. Her nipples were sticking out slightly through the cotton. I had explained to her that nipples must always be erect when in the presence of Luke. Roll them, pull them, suck them, I don't care wha...

Love in Chains Ch. 01

by BeastUnchained22 on Sep 13, 2017
Erotic Couplings

I remember the day he entered the plantation. He was a tall, dark-skinned man with a muscular physique. As he entered the gate chained with the other slaves, he looked at me. I observed his thick, athletic legs as they almost seemed to burst from the overalls he wore. His hair a deep black, it was long and knotted with curls, but complemented his Bistre brow...

Secret in the Secret Ch. 22

by roftlheory on Sep 15, 2017
Sci-Fi & Fantasy

It felt like she was walking on death row, Emily's hands were sweating so badly she swore she was leaving a trail behind her. Maybe they could use it to find her body after the Warden was done with her. Stevens led her down a hallway she had never been before to an elevator which she opened with a swipe of her key card. The muscular guard was so quiet, it w...

Daddy's Lil Girl; The Car Ride Ch. 01

by serenite on Sep 12, 2017
BDSM

It’s been such a long time since we have seen each other. It seems though that our planning has finally paid off. We agree to meet in our usual pick up and drop off place. We both are so excited, you can feel the excitement in the air. You arrive before me, like you always do, and you are waiting on me. I pull my car next to yours, and start to gather my th...

Tabitha's First Spanking

by daddyslittlegirl99 on Sep 16, 2017
BDSM

"Miss Grey, can you please come into my office? I need to speak with you." Tabitha glanced up from where she was sliding her Calculus book into her bag, a bit startled. "Um, sure Professor Holloway..." "What about the party, Tabby?" Callie muttered. It was a gorgeous August Friday; their first week of their first year in college. All the kids were gather...