Surprised By A Crossdresser Sex Stories Stories

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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...

Isabella's Reversion Pt. 03

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

My Metaphor

by hyperpress on Dec 24, 2018
Fetish

The audience drops into a continuing story written in first person POV (mostly). The following based on a true story. Given enough time, any question that occurs to the reader shall be answered, eventually. * I woke the next day, showered, put on a comfortable chemise, a microfiber and nylon blend thong and open toed sandals, made some coffee and sat down...

When Angels Cum Ch. 11

by CapDragon121 on Dec 25, 2018
Sci-Fi & Fantasy

Author's Notes: Finally have an editor/proofreader. DankMemez. If you find the quality of writing/sex scenes in the chapter to be greatly improved from the last, it's mostly due to his efforts and suggestions. He has been stupendously helpful. Special Thanks to VibrantDragon, FlyPenguin & W00tdiew00p for supporting my work Schedule: A couple of you ask...

Neglected

by komrad1156 on Sep 13, 2017
Mature

*Author's Note: Two quick points. As I've said, I know from personal experience, older (even married) women will sleep with a younger man. Falling in love and actually marrying one is an entirely different thing. Without a job to support them, it's even more unlikely, and there are only a few jobs someone between 18-22 can have that earn enough (not a lot—en...

Open Your Mind to Something New

by Dazman on Nov 4, 2019
Fetish

Open minds create amazing experiences This experience had its genesis in my early twenties when I unexpectedly began exploring my bi-side with my childhood buddy, Lyndon while both of us were studying at university (refer to my story Friends Satisfying Each Other for background context). This story takes place over a weekend, Friday evening to Sunday after...

Yes, Dear Ch. 01

by qhml1 on Sep 14, 2017
Romance

This really isn't my story, it belongs to my only crossdresser friend, who I consulted while doing research for another story. It's her dream situation, and I agreed to write is as a thank you. I wouldn't let her see the finished story. She has to read it here. Hope you enjoy, Anne, this one's for you. I was going to put it in the transsexual and cross dre...

You Can't Do That! Ch. 01

by qhml1 on Sep 26, 2017
Loving Wives

There's usually a kernel of truth in everything I write. In our thirty one years together "You can't do that" is one of my wife's favorite sayings. She knows that it irritates me and I have to prove I can. It took me about five years[I'm a man, we're dumb as rocks, ask any woman]to figure out she sometimes told me that just to get me do something she wanted....

Dexter the Photographer

by Moonraker_Bond007 on Sep 14, 2017
Erotic Couplings

TO THE READER: this story includes several characters from the series of Jason Garrett stories; however, this story is not part of that series. Hi there. My name is Dexter Malcolm. I take pictures for a living. I used to ruin - or sometimes improve - people's careers for a living. I would take photographs of them in particularly compromising positions, and...