Stiletto Boots Stories

41,602 results
Orientation
Length
Source
Infinite Scroll

At Mistress's Feet

by domn8meplease on Sep 14, 2017
BDSM

I am summoned to my new Mistress' home and escorted into the living room. The curtains are drawn, the temperature is warm and the room is glowing in bright candlelight. My Mistress is seated in a tall leather wingback chair wearing a red and black silk robe, the impression of her hard nipples visible through the supple silk fabric. She gazes seductively at m...

Ballo in Maschera, a Prelude

by Cavalliere on Sep 16, 2017
BDSM

I walked back into the living room with two espressos. Tatiana was sitting opposite our visitor; her legs pressed together demurely, her hands clasped in her lap and her head slightly bowed. I placed the coffees on the low table at the side of the leather armchair. 'Thank you.' Our visitor picked up her coffee in a leather-gloved hand and sipped it. I sat...

Where Am I Ch. 01

by MaryPettle on Sep 14, 2017
BDSM

Chapter 1 - Andrew's POV The room is dark and I can't see. My head is foggy and I can't think straight. It's cold, very cold. I try to recall how I got here but I can't remember. I recall having drinks, laughing, being an ass and then, nothing. I'm lying on the cold hard floor; I think that I'm naked. Where the fuck are my clothes? Where the hell am I? I tr...

Sex Academy Ch. 01

by adia_23 on Sep 12, 2017
BDSM

I am shaken awake by the headmistress around noon. My eyes slowly adjust to the light as she says, "Hurry, get up. Your master wants you to be ready to go out tonight at 9:00." Yawning, I slip out of bed and walk fully naked down the hall to the showers, my nipples tautening in the brisk air of the hallway. Ginny, a petite blonde first-year student, is strid...

Returning The Favor Ch. 02

by JonB1969 on Sep 14, 2017
Interracial Love

I was, as usual, sitting at my desk and wishing I had something else to do besides look through all these damned emails, when I heard Tangi answer her phone with her customary smooth husky voice. "Jack O'Neil's office, Tangi speaking. Yes he is, may I ask who's calling? Oh, hi, Amy. How are you? I'm fine, thank you for asking. Please hold." Seconds later t...

B is for Boots and My Butt

by chanstevens on Aug 18, 2017
Fetish

If you have read my other stories, you will know that my recent sexual activities have been ordered by, shared with and made so much more pleasurable by, my master – Mr Butt. You will also know that I like him to be in control but that I enjoy some control over men too and that was how it began with us. So it seemed only reasonable that I explain the story...

Nikki Comes to Life Ch. 02

by NikkiRubberTV on Sep 12, 2017
Transsexuals & Crossdressers

"Ann, do we REALLY have to go in there?" "Yes we do. You aren't wearing my clothes anymore!" Slowly I got out of the car. Before me stood a huge shoe outlet. Ann, seeing my hesitation, grabbed me by the hand and pulled toward the door. "Don't worry I won't embarrass you. Much..." Inside the place was a mad house. Women were shoulder to shoulder, grabbin...

Filming Porno for my Birthday

by 1mbibry on Sep 12, 2017
Group Sex

My birthday was fast approaching and my husband Dick had not mentioned a word about it. Granted, we are both very busy with our work but in the past we've always taken a weekend to celebrate our birthdays. Dick has been so immersed in his work this last week that he hasn't even taken time out for sex...and that is very unusual for us. Generally we are very...

The Games

by Fliccy_sub on Sep 16, 2017
BDSM

Author's note. This might not have very much sex in it, it is mostly a set up for the next part, so if you are wanting a quick read about sexual activities, this isn't going to be it. The main characters are part of a mini-universe that I have created, Felicity and Tiffany will almost always be present in my stories. ***** It was a beautiful summers da...

Monica 50: CONTROL FREAK

by SZENSEI on Nov 18, 2019
Exhibitionist & Voyeur

Here we go ready or not. "Alright Good people. Student number 69 is up for bid." Monica Gift...hell every person out there had a good laugh at her assigned Sale Number, "Who offers their hard...," Another good chuckle, every guy there was rock hard, ",...earned money for this lovely Lass?" More chuckles as all the guys heard ass over lass. "Who wants to hel...