Crossdressing Sex Stories Stories

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Return Of The Horny Femboy

by chlomo on Oct 6, 2020
Erotic Horror

This is the sequel to Night Of The Horny Femboy, it follows characters and events from that story, so feel free to read that first if you haven't :) This is an erotic horror story with mind control, reluctant sex and crossdressing. It's not meant to represent or anything seriously, it's just for fun. I'm Markie, well, I'm Markie now. 3 weeks ago I was targe...

Literotica

by komrad1156 on Sep 13, 2017
Mature

"Dear RomanticGuy05, I'm not sure why I feel the need to apologize for writing you, but if you knew me, you'd understand. That's just me. I suppose it's because sending you an email makes me feel like I'm intruding into your personal life, and since you don't know me, I'm sure you see me as some stranger butting in without an invitation. So I hope you'll fo...

Marion's reTurn Ch. 02

by jomar on Sep 13, 2017
Fetish

If crossdressing and male-male sex isn't to your taste, please back out and try one of my other stories. Also, the action here is not safe sex, but this is fiction, after all -- pretend. ********** I stopped at the door and ran my hands down my sexy little black dress, pressing the wrinkles out. I felt the tug of my ebony earrings as I looked down and saw...

Marion Turns Me Out Ch. 02

by jomar on Sep 13, 2017
Fetish

If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. And let's imagine this is set in a world where unprotected sex is safe. ********** It was looking to be a glorious day. Marion and I were on vacation in the tropics at a five star resort. We started the day with Marion touching u...

Tony and Alicia Celebrate Halloween

by Ice_Tease on Sep 16, 2017
Fetish

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!...

New Year's Extravaganza

by vyksin on Jan 2, 2025
Fetish

New Year's Extravaganza Getting even deeper into his feminine side Synopsis Our third installment of Costumed Chaos finds our intrepid couple in a stay-cation as the year turns over while they attend a kinkster ball!! Chapter 1: Introduction Author’s note Welcome to the third installment of the Costumed Chaos series of......

Marion Turns Me Out Ch. 01

by jomar on Sep 13, 2017
Fetish

Marion Turns Me Out Ch. 01 by jomar If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. ********** "There, baby, that does it. Your toes will be dry in no time. A nice shade of mocha. Do you like it? It'll go perfect with your new bathing suit." Marion put the lid on the finger...

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...

Controlling Sissy Janice Pt. 01

by sissy_janice on Jul 6, 2020
Fetish

I was uncertain which category I should post this story under. I love the crossdressing stories most, and this would certainly fit there. But the main action really is about cuckolding, so I've put it in the Fetish section. *** I had thought that my wife was unaware of my crossdressing. Not only was I wrong but, as it turns out, I was the one unaware - -o...

A Confession of Mine

by Number23 on Sep 16, 2017
Reviews & Essays

This isn't a story of fantasy or sex. Sorry. This is what the title implies. Never wrote anything before, let alone something of this nature. Here goes nothing. I'm a man of 38. A man who has hidden a part of himself from everyone for a great number of those 38 years. I'm not a writer. Not a man who knows how to put his thoughts to print. At least not in an...