6 Inch Stilettos Stories

150,158 results
Orientation
Length
Source
Infinite Scroll

William and I

by lilamisakh on Sep 14, 2017
Erotic Couplings

I knocked lightly on the door to the conference room and I waited for a reply from inside. There was no sound. I knocked the door yet again and waited anxiously for any sound or movement from inside the room. I began to feel nervous and I could feel my heart beating faster and faster with the passing minute. I licked my lips anxiously and looked at my wristw...

What's Your Price?

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

Growing up poor meant I always had to do without. I was orphaned as a baby and became a ward of the state. I could never seem to catch a break, my life was one loss after another. After becoming 18 I was discharged from foster care with nothing. Now three years later I still had nothing. My prospects weren't good and I couldn't get by on my looks. I was 5'7"...

Golden Shoes

by SouthendBoy on Oct 10, 2017
Erotic Couplings

As always I message you on the way home to let you know that I am I0 minutes away. Shortly after sending the text, I see that you are calling me on FaceTime. I'm intrigued as you don't normally call on FaceTime and I'm almost worried something is wrong or you have hit this accidentally. I answer and hear you say, "I want you when you get home." I look at...

Crossdressing Exhibition Fun

by iwant2suckabig1 on Oct 6, 2020
Exhibitionist & Voyeur

I have had a bunch of adventures that utilize both my fascination with dressing up in the sluttiest clothes I can find and doing nasty crazy things in public. I travel all around the world for work so have plenty of opportunities to pursue my fetishes in strange towns and cities where no one knows me. I will share some of these TRUE experiences with you. I...

First Day of Maid Training

by Silentghost100 on Sep 15, 2017
BDSM

There I was, at the front door of her house, thinking twice before knocking. In my short skirt and tight t-shirt, I was sweating. So excited I was, so close to reaching my fantasy. I knocked on her door. No answer. I knocked again. After a exhilarating wait, she opened the door. She led me into her house. "Take off your shoes here, Sophie, I don't want any...

My First Heels

by grgy56 on May 11, 2020
Transgender & Crossdressers

My First Heels It was a warm, morning when I awoke. The closed curtains failed to keep the bright sun shine from lighting up my bedroom. My cloudy mind cleared and I found my hand stroking my morning wood. I stretched under the silky sheet covering my Queen sized bed. The clock read 6:30. I flipped off the covers and sat up on the edge of my bed and stretc...

Adventure on CL

by Pantyhoseheels on Apr 14, 2020
Transgender & Crossdressers

This is a mostly true story of the first time I revealed my secret side to another person. My name is Colleen, secretly. I have crossdressed most of my life. It has always been my little secret. But as with most people, I have had the desire to try being with someone else, and to share my secret. I began to occasionally check Craigslist, looking for that...

Crystal the French Maid Ch. 01

by Hubee on Sep 16, 2017
BDSM

You had been working at 'The Big House', as it was known locally, for several weeks now. So far you are fairly happy with almost everything about it. The house is several miles from the nearest town but you are 'living in'. Your room, high on the top floor, may be small but it is comfortable. The work is hardly difficult, especially as your employer has been...

Lisas Ibiza Experience

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

As some of you who have read my exploits as the submissive girly Lisa will have read of my ongoing love for a door man from my hometown call Danny, well this is the story of our first holiday together. The time had come for me and Danny, time for me to tell him how I felt about him so I asked if we could go for a drink one evening when he wasn't working the...

One Crazy Adventure

by mightyesoj on Sep 16, 2017
Transsexuals & Crossdressers

I’ll start out by telling about myself. I am a good-looking guy, athletic body, and only an average penis at 5.5”. I am heterosexual. I like to shave my testicles region as well as keep my ass and ass crack shaved. When alone I like to watch porn and cross dress. I wear panties and a 34b bra. I use fake silicone breasts, the one women use to add a cup size a...