Headmistress Spanking Stories

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Home Cumming

by wakefield on Jul 31, 2019
Erotic Couplings

I have to say it's not that often that I'm nervous just driving my truck somewhere but seeing as this was the first time we were meeting at your place I was a bit more on edge than normal. As the GPS blurted out directions and I traveled down the winding roads I let my mind drift a bit to how tonight would go and what we would do. We didn't have much time to...

Trivial Objects Pt. 02

by Jane_the_Slut on Jul 31, 2019
BDSM

CW: Polyamory, jealousy, D/s, bondage, humiliation, toys, spanking. ***** I poured three gin and tonics and set them on the black lacquer tray on the kitchen island of the airbnb we rented in Banff. My figure, clad in a little black apron, towering heels, and a pair of nipple clamps attached to a thin chain, reflected back to me in the darkened floor to ce...

Sex 101 Ch. 01

by kitten190069 on Aug 20, 2019
Erotic Couplings

Professor Emma Reed adjusted her tortoiseshell glasses and sighed. She shuffled papers around on her desk, hoping the letters of reference would write themselves tonight. She kicked her feet up on the leather ottoman, took a deep swill of her red wine, and leaned her head back into the cushions. Two months ago, Ted stood in her driveway with a cardboard bo...

100 Centimetres - Experience 08

by icefantasygirl on Feb 11, 2019
BDSM

Authors Note: For the man who has helped me in my journey to melt my walls and to whom I have surrendered my heart, my mind and soul. My owner, my protector and my lover. Ice ~ I remember calming down for that powerful orgasm that I had just experienced from being fucked by you outside the three story window. My breasts, face and cries for all to see and...

After Church Ch. 04

by alien_freak_nugget on Feb 11, 2019
Transgender & Crossdressers

Saturday morning... The cool air on my ass and balls was beginning to drive me into a frenzy as I squatted on my high heels. I was wearing a black pair with 5 inch heels and a matching black bra but my thigh high stockings were white with little black bows at the top. In my right hand was Rick's massive cock and in my mouth was Mike's 8 incher. It was Satu...

Brian's Sleepwalking Adventure Pt. 05

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story is based on what may be an urban myth from my college days. A fraternity brother told me about the incident after my own adventure, described in my story "Pledge Class Payback" so I believe it to be true. When I asked about it, no one could remember the actual names or years or the fraternity. However, it fed my imagination and inspired me to writ...

Brian's Sleepwalking Adventure Pt. 01

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story is based on what may be an urban myth from my college days. A fraternity brother told me about the incident after my own adventure, described in my story "Pledge Class Payback" so I believe it to be true. When I asked about it, no one could remember the actual names or years or the fraternity. However, it fed my imagination and inspired me to writ...

Her Anniversary Surprise Ch. 02

by imakeisabellasquirt on Sep 13, 2017
Loving Wives

Following feedback from the last story, the second chapter has been changed to the 3rd person. I invite constructive feedback as this is only the second chapter of my first story. Thank you and please enjoy! * After a wonderful night out celebrating their anniversary, Izzy was enjoying the latest of Dave's surprises up in their hotel room. Now that Dave ha...

Jacob the Bull

by kamalw1 on Sep 12, 2017
Interracial Love

Jacob walked up the block towards the hotel, a smile on his face. He had been talking with Jessica online for a long time, and he was looking forward to finally meeting her. She was visiting the city just to see him, and to hopefully get a special gift to remember him by. Jacob had been in the bull lifestyle for a few years now, and had successfully bred wi...

My Girlfriend's Slutty Roommate Ch. 02

by writemarksmith on Sep 25, 2017
Group Sex

I lay in bed while I watched Abby get dressed for work. God, she is beautiful, I thought. It had only been twenty minutes since I finished fucking her. I had been on top, as always, and she lay there rather still, as always. Despite myself, my thoughts turned again to Kate. Kate is Abby's rather unattractive roommate that I had been secretly fucking for the...