Headmaster Punishment Bdsm Stories

61,534 results
Orientation
Length
Source
Infinite Scroll

Box Lunch Ch. 01

by arbenitre on Sep 17, 2017
BDSM

When she got the box at work, by messenger, she couldn't help the smile that played at her lips. It appeared to be just a normal delivery by courier, much like any other that she would get three or four times a week. Normally these boxes would contain checks or some essential paper to the business that she managed the office for, and to the other office pers...

Bound To Be...

by PleaseMayICumSir on Sep 15, 2017
BDSM

It started two years ago with some rather odd conversations. I'd drift out of the constant chatter between my wife, Kate, and her divorced friend Patricia, only to find myself returned to a flirty conversation with the odd kinky gesture - the two of them giggling like school girls. Curious but improbable. Months later there was another three-way conversat...

Helen's New Role

by grinder on Sep 14, 2017
BDSM

Helen is my wife, she is a very womanly woman, she was a brunette with thick dark brown hair and dark brown eyes. Her skin was sallow and tanned easily. Her figure was not slim but satisfyingly ample as a woman should be with shapely generous breasts and wide hips. The day I found out about her infidelity I really was hopping mad. Afterwards we rowed for a...

Eradicating Knotweed Ch. 05

by Sputnik57 on Sep 26, 2017
BDSM

He opened his eyes to see Elaine walking from the bed to the en-suite, and lifted himself to admire her naked, superb shape as she went. Soft giggling behind him made him turn; all three girls were back to their usual selves after the strange events of the day before. Abigail moved over in the bed and cuddled up to him; she giggled again as she rubbed his no...

Mistress Penny's First Day

by ThoughtStorm on Sep 17, 2017
BDSM

AUTHOR'S NOTE: This Untold Story takes place prior to the events of Mistress Kathy's Slave Catalog. You may have heard rumors of a faraway place where your dreams of bondage and domination can be made into reality. Those rumors are true. Just be careful what you wish for. At Mistress Kathy's Academy of Domination and Submission, professional mistresses an...

Maid and Laid

by Framboise on Sep 16, 2017
BDSM

It was a Sunday afternoon, and You were hosting a small party, for a few friends. You had not told me who those friends were - only that dinner would be served for six people - of course, as You did tell me, I would not be included... ...for You told me that my role was to serve You, Him, and Your guests...but I had not expected for You to insist on certain...

LV

by mehiali on Sep 17, 2017
BDSM

The piece of paper on the counter was not unusual in itself; my house mate often left notes. Usually they were about things like "I bought laundry soap" or "dinner is in the fridge – heat on high for 3 minutes." In the 5 years we had shared this 3-bedroom house, she had never, ever had a request. That is exactly what made the note really catch my attention....

Early One Morning

by Got2Burself on Sep 17, 2017
BDSM

Awaking on a bright Saturday morning I stretch and lay on my right side. The sun shines in through the panels of the half closed blinds, and a bird chirps outside the window. Stretching my arms and legs, and while doing so my legs press against your chest. Looking up I see you at the end of my bed, your body slightly curled around my feet. Your hair is matte...

Shrink

by Ariel797 on Sep 17, 2017
BDSM

When I was in college, my dad sent me to see a shrink because he said I kept fooling around with guys so much. I'm of age, I don't have to go, but he's my dad, you know? I told him and the doctor that I was careful. I was on the Pill and I don't take chances with a bunch of strangers. I have some friends, some fuck buddies, and we stay in our group so we don...

Smolder

by Vei1edthreat on Sep 16, 2017
BDSM

I am not a writer per se, I am reader, and I generally prefer character driven lengthy stories on Literotica. That said, sometimes a story get in your head and you need to figure out a way to express it. This was one of those stories and its dedicated to all of you who came into your kink later on in life, and who pursue it indirectly rather than hurt the f...