Dress Up Stories

354,756 results
Orientation
Length
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Infinite Scroll

New Family Dynamic

by grayshade on Sep 17, 2017
Loving Wives

This story is an accompaniment to my earlier story "The Visitor Next Door" that was published on Literotica in March 2013. In that longer story, husband Jack begins by voyeuring Jennie Carson, the neighbors' college-age daughter, and Zoran (an androgynous male model visiting Jennie for the summer) who both seduce him and wife Paula in turn. Meanwhile, Jack's...

MaidSally Episode 02

by cd2the9s on Sep 16, 2017
Transsexuals & Crossdressers

As I explained in my first episode, I am a kept Cross dressing Maid-servant for my Master who I also refer to Mr. G. (or G). My Master provides for me and makes my life comfortable. For this, I provide him with a willing and compliant servant. Master keeps me quite busy with daily chores and things and he uses me as he wishes. Sometimes he lets others use me...

Christmas Parties Ch. 03

by Woody Woodwood on Sep 11, 2017
Loving Wives

Recap Hi, I'm Jack, and I want to share with you the sorry tale of how my wife ended up being used as a sexual plaything by a group of men who work for the same company as her, and how much I enjoyed watching. The events that happened are all true, and I admit I'm not proud of my inability to stop what was happening, or the fact that I found it very erotic...

Magic Dress - Isis

by SlightlyRude on May 4, 2020
Transgender & Crossdressers

I had never noticed the shop before, and I don't know why I went in. It was called 'Heart's Desire'. As I entered, the woman behind the counter said "The dresses are over there." I was a man in ordinary clothes. Why would she say that? "Just browsing," I said, and looked everywhere but at the rack of dresses. There was really nothing I wanted. There were...

Little Girl Games Ch. 04

by TheSparkZone on Sep 19, 2017
Exhibitionist & Voyeur

This is the story of how Amy, Kelli and I spent our summer vacation. We'd just graduated from high school and we wanted to have one last crazy summer together before officially joining the adult world. We were three sweet and innocent girls from the mid-west until we discovered the thrill of exhibitionism. Flashing at work can be fun, as long as you're not a...

Prom? Ch. 02

by New_Girl_ on Sep 25, 2017
Transsexuals & Crossdressers

I hope you guys enjoyed Chapter 2! I know it wasn't as sexual as the first part, but trust me, we'll get there. Chapters 3 is already in the works, and I hope to have it completed soon! If you liked the story, feel free to leave me a comment or a rating. Thank you! ~~~~~~~~~~~ The red Mercedes E class sedan raced down the 580, going a cool 70 miles per ho...

Graduation Party for Tommy

by Tender86 on Sep 13, 2017
Loving Wives

Debbie and I have been married for just over one year. We married right out of college. Debbie is a real doll at 5'5", shoulder length blond hair and a sexy 34-22-34. Her firm, pear shaped 34B breasts are accentuated by perky, mouth watering nipples. A flat smooth stomach flows down to a prominent mound in front and perfectly rounded cheeks out back. Her leg...

When Val First Went Without Panties

by applevalyan on Sep 25, 2017
Exhibitionist & Voyeur

When I first met Valerie back in 1972, she was a senior in high school. She had turn 18 in January and had only a few months of school left. She loved wearing short dresses and skirts anywhere and everywhere. Many of her dresses just barely covered her ass, but she said she didn't care. It never seemed to bother her when somebody got a flash of her panty cov...

Freyja Inc. Ch. 01

by Texas_law_man on Sep 15, 2017
Exhibitionist & Voyeur

There has been little doubt in Shea's mind that she always wanted to be an investigative reporter; the problem was getting a break. It has been three years now since she graduated with honors from Ohio State University School of Journalism. The dream job of working for the New York Times was still a dream and the rag she did write for wasn't even in the same...

Another Pantyhose Tale

by weluvhose on Sep 16, 2017
Transsexuals & Crossdressers

I come home from work to find two pretty dresses complete with hosiery and shoes lying on our bed. You are in the bathroom applying makeup and tell me to jump in the shower. You explain that we have the house to ourselves tonight and you want to seduce your "girlfriend". I quickly undress, join you at the mirror and shave my 5 o clock shadow from my face....