Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

Duplex Ch. 11

by naughtyboyincali on Sep 25, 2017
Exhibitionist & Voyeur

When Mary pulled into her garage and closed the door behind us, I could finally relax. Except for a brief stop at a rest stop, I'd been laying back in her passenger seat, completely naked, and hairless with an erection. She kept me excited the entire time. When she would pull into the left lane to pass cars, I would press myself as a far down into the seat a...

The Second Time Around Ch. 04

by cassandraharper on Sep 14, 2017
Interracial Love

Previously in "The Second Time Around:" Finally awakened in the form of Adriano Comito, Caid Harrison, vows to find Brigitte Hils in order to once more have her back in his life. Now after completing physical therapy and officially claiming his newly rightful place in the Comito family, Caid (forever in the guise of Adriano) obtains the ability to see Brigi...

Pleasures of Masturbation Ch. 05

by shybadgirl on Sep 25, 2017
Toys & Masturbation

This story is a little bit different than the first 4 I wrote but I hope that you enjoy it. * I met a man on the net that has really got into my mind. His way with words is incredible. His voice is so fucking erotic!!!! When I talk with him it's almost like he is right next to me whispering into my ear. His name is Ryan. We have played online and on the p...

Further Adventures of Susan Adams Ch. 02

by SteveLee1146 on Sep 14, 2017
BDSM

Other experiences were of a completely different nature and showed a very changed Susan, more changed than she had realized. For example, after the spanking (which, at least, did Don a world of good), the rest of the week went on in its normal fashion with the exception of one event which probably showed these alterations in Susan's behavior as well as anyth...

Wife's First Sybian Ride

by intotrouble on Sep 16, 2017
Fetish

I was online one day at home, bored out of my mind and had an urge that started growing in my pants. My cock needed a little attention so I decided to try and look for some interesting porn online. I type in porn in the search engine to see what came up and I tell you there are some interesting sites out there in cyber world. I clicked on a couple and then I...

Bound by Ecstasy

by MethodicMortality on Sep 17, 2017
BDSM

You come home from a long day at work and take off your shoes, put your purse down and toss your keys in the plate next to the door. You tiredly stroll through the house, passing each room looking for some soft physical comfort but aren't able to find me. Walking into the kitchen you see the light is on and realize I must be home, so you start making your wa...

How To F*** Your Daddy

by sarahhh on Sep 26, 2017
How To

Let me preface this tutorial by saying that fucking your daddy is illegal in the United States. In the state of New York it is a felony with a maximum penalty of four years in prison. So go to France where fucking your daddy is not illegal if you are an adult. The rules of this How-To Contest say, "We will not accept How-To submissions that teach people how...

The Visit Ch. 02

by hoglust on Sep 12, 2017
Erotic Couplings

I stepped up to her and gently kissed her on the lips, drew away and said softly, "I have loved you for a very long time." Jane looked into my eyes and said, "Where do we go from here?" I had secretly loved this woman and never knew what to do. I knew her husband was a shit and never gave her the attention she wanted/needed. Jane was a beautiful statuesque...

Punishment

by sweetlittlesub on Sep 12, 2017
BDSM

I snuggled against you, my tiny body curled into yours, as the sun glimmered through the gauzy hotel curtains. I always woke up early, my body used to waking up early from high school. I still had not gotten used to that in college, and scheduled my classes early in the day, so the rest of the day I was free to write, or text you, or fingerfuck my little cun...

Ponytail

by Nikita_writer on Sep 13, 2017
BDSM

Sweetlips' body, gingered by the sun, was lithe and her lips were chapped from thirst. Her brown hair, with streaks of red and blonde throughout, had grown to reach the middle of her back. The soles of her feet were toughened from running without shoes. She had developed that faraway look in her eyes that comes from detachment. Dreams of traipsing into a cof...