Cruel Boots Stories

52,836 results
Orientation
Length
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Infinite Scroll

The Boss Retires

by marriedpervs on Sep 13, 2017
Group Sex

The Boss retires – my parting gift! My good friend, and my boss for the last three years, Al, arrived at my desk and told me. "Babe, it's time for the old boy to give it all away. I'm packing up the tools and heading north for good!" So Al had decided to retire. We spent a good deal of that morning figuring out what would happen after he was gone. In the...

Sex, Love and Sabotage

by ALandRF on Sep 17, 2017
Mature

With the Mission: Impossible theme playing in my head, I skitter across the street, just a passing shadow flitting beneath the hazy glow of street lights. Slithering through the shadowy drainage ditch, I work my way slowly to the along the row until I come to first shiny behemoth and slip under it. The misty, foggy night obscures the sound of the ratchet as...

Dark Eyes

by easyridr101 on Sep 13, 2017
Erotic Couplings

I'd noticed her looking at me several times-often as we passed in the hallways and as we rode the elevators to and from classes where we were conservatory students. She was small--the top of her head barely came up to my chin, and I was only 5'11". But much more striking than her small stature were her eyes-- of a strange, mellow brown, suffused with a pecul...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Rogar and Rainath, Going Home

by nothingisalways on Sep 24, 2019
Celebrities & Fan Fiction

Though she'd vowed to flee the heat on the next caravan headed north, Rainath stayed on in the desert. For one, the inns were cheap- though the price of ale was more than enough to make the difference, she didn't drink so much for it to matter to her. The gold was plentiful, too, and once one got accustomed to avoiding the searing daytime heat, it could be n...

Miss Annabelle Ch. 01

by Timewarp10 on Oct 16, 2018
BDSM

It began as a misunderstanding. I realised there had been a mistake as soon as I answered the front door on the first evening she came. "Have I come to the correct address?" She asked, looking at the piece of paper on which the officer at the student residence office had written my details. I could smell the sweet scent of the fruity gum she was chewing....

Break Me: A Love Letter

by TemptressoftheFaithful on Dec 3, 2018
BDSM

For such a rebel and heathen, perhaps it's ironic that she doesn't believe in choice. No, in her mind, our life paths were determined well before we were born. Now, she did believe that it was us that did the writing. In our fullness, our most integrated before becoming confined to these bodies, we knew us better than most of us are inclined to know ourselve...

Miranda's Awakening

by Painfullypatient on Jan 28, 2020
Exhibitionist & Voyeur

Ever since she and Rick decided to separate, Miranda's libido seemed to be on an uncontrollable growth rate. She never realized just how pent up her desires were till her mind came to grips with the freedom that lay in front of her. Rick's lack of attention and her focus on climbing the corporate ladder created a mindset that put any sexual needs or desires...

Dark Division - Dani Ch. 04

by bdbeauty on Sep 11, 2018
Romance

Dani and Vince were inside the cabin, temporarily out of the cold air outside that was only going to get worse. The large trunk they hauled from the lake had a huge padlock on it, and they knew it would take more tools than either had on them to open it. Vince had made the call to Nick as Dani sat huddled in one of the cabin's chairs rubbing her arms furious...

Just Look at Me Now Ch. 03

by GFfan on Apr 13, 2020
Transgender & Crossdressers

Eager as I am to tell you about my first crossdressed Halloween with Jude and Becky, I must save that for a later chapter and fill you in on some major developments that occurred as my first summer of feminization ripened into autumn. Surrounding these landmark events were patterns of submission we had established early on. I wore panties 24/7, and I shoppe...