Transsexuelle & Crossdresser Stories

809 results
Orientation
Length
Source
Infinite Scroll

The Sissy Mark

by Son_of_Battles on Nov 2, 2020
Transgender & Crossdressers

This is my story submission for the Literotica Halloween 2020 Story Contest. I ask that you forgive any errors you might find, I literally just finished 12 hours before the deadline, and have zero time to get it to my editor before submissions close. As soon as Skye can get a chance to edit for me, I will repost a freshly edited update. Thanks, and don't for...

Finding Himself in Her Ch. 03

by Mr_Owlow on Sep 25, 2017
Fetish

RING! RING!! RING!!! "Ummm ... Hello?" "Hi, I'm calling for Mr Jaime Baudelaire?" "Good morning, this is he." "This is Savannah from Dr. Simmons clinic, I'm just calling to confirm your appointment for three o'clock." "Oh, right, damn, I forgot about that. Thank you so much for calling!" "No problem, we'll see you at three pm, bye!" CLICK What a wa...

Important Business Comes Up Ch. 02

by Emmcee20 on Sep 13, 2017
Transsexuals & Crossdressers

In the opening chapter of this story Jason Meadows has arisen to the level of Vice President in an advertising agency and immediately become the target of office predator Dana Jones. She quickly discovers his interest in wearing lingerie under his business suit and, after an initial meeting, invites Jason to her house for further discussions about his new ac...

I am Number Four

by princessnocturne on Sep 18, 2017
Transsexuals & Crossdressers

I stood silently in the middle of my living room, surveying my very own new apartment with a weary satisfaction. I still had boxes of small stuff to unpack, dishes and books and the like, but the furniture and appliances were all in place, and the heavy lifting was more or less done. I felt a warm glow of pride as I saw it take place before my eyes, my first...

The Reunion

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

© 2015 by Thrillerauthor Twenty years! It's hard to believe that much time has gone by since I limped out of Grover Cleveland High, at the bottom of my class, prospects zero. My sole achievement was the dubious designation as Class Clown, in recognition of outrageous pranks which got me suspended twice and almost expelled. The last, which nearly ruined the...

Husband with Testing Device Ch. 02

by Floydman1 on Oct 24, 2018
Transgender & Crossdressers

Author's note: welcome back! To those who left constructive criticism or encouraging words: thank you! It truly does mean a lot and I appreciate it very much. This is the next installment of this series. Unlike the way that I usually write, I'm banging away at this story because I'm fascinated at what will happen. I always found it hard to believe when Step...

Girlfriend with Testing Device Ch. 03

by Razmagurk on Jul 10, 2018
Transsexuals & Crossdressers

Author's Note: This is part three of my smutty little romantic comedy series. This chapter starts off the Mall Arc, which runs until chapter 6. One of the longer chapters, it's a little lighter on the smut, but a little heavier on the swaps, and I hope you'll find it no less sexy. Please leave a comment! I really do love hearing from readers! Even when I'm...

Diary of a High Price Escort Ch. 21

by R_U_Romantic on Dec 25, 2018
Erotic Couplings

I arrived home from my auto shopping trip about five o'clock, making sure to check my front door for any new placards Barry might have hung, then pulled into the garage and pushed the button over my sun visor to close the garage door. I sat in the car for a minute thinking about my day. I'd given my attorney the okay to get my divorce finalized and let a tot...

Nancy Meets Monte

by sub_nancy_cd on Sep 16, 2017
Fetish

Looking in the mirror of the ladies washroom at the airport, I fix my hair and make-up, I was glad I decided to wear my hair up in a pony tail, it made me look cuter, I wore my black mini skirt a white blouse with smart lace surrounding my breasts, I wore white pantyhose and my 3 inch black heels, I turned back and forth in the mirror, thinking to myself, it...

Exotic Pussy Cum Extortion

by Alluring_Crimson_Shifter on Sep 14, 2017
Anal

Leon struggled in his science class and was almost giving up at the idea of graduating from high school. As an 18 year old he did not see good prospects as an adult. His teacher coached him and encouraged him. She was his science teacher and sometimes spent time after class helping him with his studies. He admired her intelligence and her looks, and grew fon...