Dressed Like A Slut Stories

361,443 results
Orientation
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Infinite Scroll

Cockwhore's Special Evening

by Freeyourmind on Sep 19, 2017
Transsexuals & Crossdressers

It was Friday night and my wife had just left on a weekend business trip. I helped her pack all of her bags, she always packs too many suitcases, and waved goodbye from our front door as she drove away. I love when she takes these frequent trips because it provides me plenty of time to indulge my darkest passions and desires, desires that can only be fulfill...

Pool Boy Gets Dressed Up Ch. 02

by tonyl65 on Sep 26, 2017
Transsexuals & Crossdressers

I would like to thank the readers for the great feedback. I hope to continue this storyline to your liking. Feel free to offer suggestions. The feedback helps. * Yesterday I was a shy, young, teenage pool boy minding his own business. Today I am dressed as a sissy slut and just finished eating my Mistress' pussy. My arms are handcuffed over my head and at...

The Transvestite Stalker

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up...

Bead Slut Ch. 05

by evals22 on Sep 13, 2017
BDSM

The rest of the day at the conference passed in a foggy blur. All I could think of was Lori and Frank, or rather what Frank was having Lori do. When I arrived at the hotel I went to the front desk where I was given a note and a room key. The note was from Frank saying I was to get ready for dinner and knock on the connecting room door at seven o'clock. He su...

Fun With Friends Ch. 02

by HighHeeledHoney on Sep 14, 2017
Transsexuals & Crossdressers

This is a continuation of the story 'Fun with Friends'. I hope you enjoy this as much as the first part... Thanks again to kjplotts for the editing work. * After Becca said that, my eyes moved across to Greg's face, unsure of what to expect. I didn't know if he was going to be angry that his girlfriend had tricked him into thinking that it was her stri...

Rachel's Mother Ch. 3

by painmaster on Sep 12, 2017
BDSM

On Monday evening I went around to Rachel's place as always for dinner. Sandra was not home as yet. I told Rachel that I was really horny from not having seen her all weekend. The truth is that I was still thinking about her mother and was desperate to let a load go. Rachel was sure that her mother would not be home for at least half an hour so we slipped in...

A Slut is Born

by Littlemissblair on Sep 12, 2017
Transsexuals & Crossdressers

I can't believe it. I've been Sarah's roommate for 6 months and never, for one moment, suspected anything different about her. She is the prettiest, sexiest, well-built girl in our dorm. Some things were a little strange with her now that I think about it. Like she always wears skirts, never jeans or slacks. I just thought she liked to show off her long, ta...

My Wife and I Became Sluts Pt. 01

by mandiejune on May 22, 2018
Transsexuals & Crossdressers

My wife Carol was away for a week due to business conference. She was blonde 25 years old 5' 5" with very sexy body and 36C breasts and very sexy bum. We had been married for 3 years and had no children. I was called Tom and 28 years old and 5' 6" and thin. I was IT systems designer and worked from home. I was also a crossdresser that my wife and Mistress al...

Dressing for my Master

by Chriszinner5 on Sep 16, 2017
Transsexuals & Crossdressers

Master is coming round tonight and I have the flat to myself. He wants me dressed and ready for him. Good! I am aching for his meaty manhood and looking forward to tasting his cum. He has given me instructions as to what I must wear and I know exactly what will turn him on most. I have the requisite clothes and hope he will like what I have done. The only...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...