Cross Dressing Stories

72,522 results
Orientation
Length
Source
Infinite Scroll

Jack the Lad

by Cleardaynow on Aug 31, 2017
Humor & Satire

A few months back I stumbled onto the Literotica site. Like everyone else, I found that a lot of the stories did not appeal to me. But I did find a number of stories that had good plot, good characterisation, good story flow and were well written. They made me think. They were erotic too. I looked out a few stories I had written for myself a few years back...

Dressing My Husband Up in Panties

by jennycnnn on Sep 25, 2017
Fetish

I don't know how to start this story other than to say that my husband loves panties and lingerie. I know that there are thousands of men out there with this same fetish and this story is for the women that love them to help with some new ideas. First a little background information on myself. I have almost been married to Steve for 10 years now and we have...

Bitch Maker Ch. 03

by YANKEE DAN on Sep 12, 2017
Transsexuals & Crossdressers

Author's Note: A lot of people have requested that I continue this series, and finally I have gotten around to it. Enjoy! * "Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay t...

Gigolo Ch. 01

by grantvigor on Sep 16, 2017
Novels and Novellas

This is a long-term story with potentially an infinite life in it, and it revolves around a man (written from a first-person perspective) finding himself in deep financial trouble and finding money and enjoyment in becoming a high-class male hooker. This chapter, as well as the ones to follow, will hit on more than one particular genre, which is why it's bee...

Isabelle and mr. Bête ch. 03

by SciFurz on Sep 26, 2017
Romance

A sting on Isabelle's bottom woke her up with a yelp. She turned around to see Jean-Marie standing next to her bed, his arms folded across his chest. 'Good morning ms. Anderson.' he said. 'You wouldn't wake up when I called you.' The haze of sleep ebbed away and the sensation on her bottom told her what he had done to wake her up. No one had dared to spank...

Brought Down to Serve Pt. 04

by MissKateKees on Sep 14, 2017
Exhibitionist & Voyeur

Throughout the morning train ride, he squirmed in discomfort. His thick pubic hair kept getting caught in this damned cage. And none of his underwear fit over it, forcing him to go commando. A moment of blind fear overcame him as he walked into the office. He and Tessa were usually the first in and sure enough there she was, sitting in his chair, at his desk...

She Wears The Trousers

by Quietoldie on Sep 19, 2017
Transsexuals & Crossdressers

I knew that Wendy was a strong willed, ambitious woman when we met. She had been active in a left wing feminist group at University and had landed a good job with prospects after leaving. In contrast I am not a high achiever and dropped out of Uni after a couple of years. Since then I have had a number of low paid jobs and am presently unemployed. To be hone...

Naughty at School Ch. 05

by ECHoney on Sep 13, 2017
First Time

Hello to all my readers. Here is another story of when I was first attending college. I hope you enjoy it. ***** Math Tutor Lessons My Math teacher called me into her office because my grades were bad and I was going to fail the class. She suggested that I get a Math Tutor to help me. Usually in this type situation I would just seduce the teacher for a be...

High Society Pt. 02

by shoguy on Oct 15, 2018
Mature

In this chapter, seventy eight year old Virginia Wechsler starts a week-long encounter with an eighteen year old stud with incredible talents to please a woman, who is blessed with a tireless, twelve inch cock. After the call disconnected I sat in a daze. My body was on fire. I just hung up from a call with an eighteen year old boy I had met less than twent...

Happy Birthday to Me

by maninconn on May 6, 2019
Loving Wives

I haven't submitted anything for a while. I've written a lot, but haven't been satisfied with my endings, so nothing has made it quite this far. I've struggled, and tried various ideas, but just haven't been able to close the door. Then this story just kind of popped out of my head fully formed. So thank you to whatever muse got into my head last night! No B...