Trampling Heels Stories

81,118 results
Orientation
Length
Source
Infinite Scroll

My Private Secretary

by MahlerSymphony on Sep 13, 2017
Anal

You are my secretary. You come in with the morning mail wearing smart business attire - - a black skirt ending just above the knee, white blouse, navy jacket, black thigh high stockings, and heels. Your red hair is pulled up. You give me a prim smile as you hand me the day's post, turn on your high heels, and walk briskly out my door. My eyes linger on the s...

Family Values

by thrillerauthor on Sep 12, 2017
Transsexuals & Crossdressers

Dear Kit, This is the most difficult letter I’ve ever written. I only wish I had the strength to tell you what I am about to say in person, but I don’t have that kind of courage. That’s why this letter is wrapped around a video cassette. A picture is worth a thousand words. Before you put the cassette in your VCR, let me try to prepare you for what you ar...

Realising Her Potential Ch. 01

by Innocent_kink on Sep 11, 2017
BDSM

A deep breath rushes through her body as she tries to steady her nerves. All day she has been stumbling around her thoughts aimed on tonight. Even though he hasn't given enough away to truly enlighten her, she has been trying to fill some of the mental gaps using his snippets of information to set the scene. To her this night has been a long time coming yet...

Generous Masseuse Shares

by mgirl0022 on Sep 17, 2017
Loving Wives

Hello. This is a true story. So little about me (even though story mainly isn't about me) I am 22 years old. I consider myself attractive and get a lot of attention from guys. I dress down often as to not draw attention to myself. I am 5 10 and have long legs, long brunette hair and green eyes a big chest and of course a big smile. I am a massage therapis...

Henry and Janice Ch. 01

by Just Plain Bob on Sep 16, 2017
Loving Wives

Henry spent most of the day at work wanting to go to the bathroom and beat his meat. Just the thought of Janice waiting for him at the motel kept him hard. She was the best piece of pussy he'd ever had and he had gotten her because of an off-handed remark. Janice and Doug were his next door neighbors and Janice had invited him over to a party she was throwin...

NiteLifeWife Ch. 01

by HotKittySpank on Sep 17, 2017
Loving Wives

(I hope you like this! Give me feedback and ideas for new stories! Thanks! --HKS) * He had been on to me for a while. He knew I sometimes fantasized about other women and encouraged me. "Let's go to one of those places," he said. "We can get a girl, anyone you like. I want her to go down on you. I want to watch." Whenever he brought this up, usually high...

Ashley's Misconception

by sftswg4us on Sep 17, 2017
Loving Wives

It all started on a lazy, hot afternoon by the pool. My wife, of 20 years, Ashley and I were having a few drinks, as we floated naked around the pool. The fullness of her breast has always driven me nuts with desire, as well as her 5'11'' very fit, and voluptuous body. This woman is a knock out from the word go, and has never looked her age. And as long as y...

Rendezvous with the Night Ch. 01

by surraville on Sep 16, 2017
Loving Wives

Rhonda was desperately trying on different items of her clothes for tonight's event. The time was almost up for her to leave. And different blouses and skirts were scattered about her adorned feet. She already had the basics done. Her brunette hair is done up fashionably with a few strands of hair naturally falling on her side and back. Black lingerie set sh...

Open For Business

by Babee_girl on Sep 14, 2017
Anal

After reading my posted story I spotted some errors. I did not know I could edit it and post the edited version. So here is my edited version, I do hope it meets with everyone's approval and you enjoy reading it. Thank-you! babee_girl I look at my watch and grumble, "Damn, it's only 10am." I have been sitting by the front window of the store were I am worki...

Reinvigorating a Marriage Ch. 01

by BrettJ on Sep 16, 2017
Novels and Novellas

by JoelC as told to BrettJ © 2008 * I hope this story can inspire some of you to believe that if you work on a marriage in trouble, you can put new life back into it. I know I did and I am happier now than I have ever been. It wasn't always that way. Let me tell you my story and perhaps you'll see what I'm talking about. It had never made much sense to...