Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

Unexpected Perquisites Ch. 02

by Lady_S on Oct 12, 2017
BDSM

The joy and ecstasy of that incredulous tongue fucking by Mr. Williams had brought about a chain of orgasms that I lost count of. Fortunately, he had gagged me when, earlier, he had put on the cuffs and tied my thighs. Or else, my endless screams would have reverberated through the entire mansion that housed my boss's residence and office. And yet, I hadn't...

The Weekend at the Lake

by erotiquill on Sep 13, 2017
Erotic Couplings

It was two weeks ago that Ray and Emma first told us about Jon. He was someone they had known for a little over two years and felt that our relationship had reached the point where they could tell us about him. My wife, Gwen, and I have had a sexual relationship with Ray and Emma for almost a year and have become very good friends during that time. "We have...

Celebrate Freedom!

by sophia jane on Sep 16, 2017
Reviews & Essays

Thanks to Softouch911, again, for being a fantastic editor and friend! * My grandmother had a bookmark when I was growing up that said: "Celebrate freedom. Read a banned book." The irony never escaped me; while we have free press, we also have people who exercise their freedoms by protesting, and banning, the words of others. My grandmother celebrated he...

The Red Moon's Power: Hawks Tale 01

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

The Red Moon's Power: Hawks Tale OK, so like I said before, It's been way too long. I finally decided on a much needed conclusion on Hawkens story. He needed a happy ending or so I've been told. So here it is. Enjoy! ----------- ~5 years before Shinai and Aiden were reunited and just before the Katsari attack on the Senatri, At Illoris Academy in the Sitr...

Code Name Tequila Ch. 13

by Travel_by_day on Sep 15, 2017
Transsexuals & Crossdressers

"Right here, right now... Right here, right now..." The music boomed out of the Bang and Olufsen stereo system as Carlos followed the Hyundai driven by Fernandez into the outskirts of Colon. Carlos turned the music up. The drive, though scenic, had been boring, and the music made the time pass. Carlos could feel the power of the Audi R8 through the wheel an...

Spanking 101

by Sir_Nathan on Sep 13, 2017
BDSM

"All right, all right. Settle down and take your seats. Yes, that includes you with the green mini in the back row... "Thank you. "Now, welcome to Spanking 101. My name is Mr. Nathan and before we get started, I'd like to get a few things straight... "I will be speaking from my own perspective. In other words, I'll say 'he spanks her' rather than vice v...

The Masquerade of 1900

by daniwilliams on Sep 14, 2017
Erotic Horror

"Who are you, then?" "I can't remember," she said, smiling. Her lips curled up impishly at the corners and her eyes glittered. "You go first." He nodded and spun her delicately around with one upraised hand. She was flamboyantly dressed in a crimson gown topped with black lace over her shoulders that draped over the rather suggestive bodice underneath. Her...

Schoolgirl's Punishment Ch. 02

by mybaby on Sep 16, 2017
Novels and Novellas

The Awakening. Sandy ran to the toilets just hoping her best friend Trudy was waiting there for her. "Sandy!" Trudy looked shocked when she saw the state of Sandy "My God what has he done to you"? "Six of the best," "What! Where?" Sandy moved to Trudy who was by the sinks, she turned her back on Trudy, and slowly raised her skirt. There was a silence...

Lines

by water_side on Sep 17, 2017
BDSM

'LINES' is entirely self contained, although the three main characters first appeared in the 'Please!' story Heartfelt gratitude goes to PrincessKiwi, who not only inspired this role-playing fantasy (with the short and sweet 'Sir' stories) but also gave me invaluable help and advice during the writing of it. If you like it, then that's due to Princess' inf...

High School Spanking

by DonBrown on Mar 20, 2018
BDSM

When our youngest daughter, Teri, left school, it was the end of an era. No more delivering and collecting kids from this school activity or the after class detentions. After class detentions, we would have welcomed those when I was at school, instead of the beatings, which were handed out wily nilly. Don't get me wrong, I am not saying we did not deserve...