Halloween Crossdressing Stories

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Things That Turn Me On

by Raquels_Panties on Apr 22, 2020
Fetish

I'm a 28-year old male. I live a normal life in public. I like women and men. I'm 5'8" tall and weigh 135 pounds. One might consider my features, my face, my body shape, more on the feminine side of the spectrum, than on the masculine. I'm okay with with that. I use this to my advantage and have allowed my hair to grow out. It falls just below my shoulders....

The Perils of Young Guys

by Etaindarcy on Aug 7, 2019
Transgender & Crossdressers

Young guys are pretty; but not always so fun. I've only been with one guy younger than me, so maybe I don't know what I'm taking about - but here it is. If you've read my previous stories then you know about my first time with Jack and Kyle and about my special friend Missy and her teenage brother Caleb. If not, let me catch you up. I met Jack and Kyle in...

The Book of Dreams

by cddannie18 on Sep 15, 2017
Transsexuals & Crossdressers

So there I was, once again sitting at home on a Friday night! I was convinced I must be the only high school senior without anything to do tonight. And just to top it all off... its Halloween! The biggest party and socializing night of the year. I am such a loser. I have no girlfriend... no social life for that matter, and the one thing I really love to do I...

Creating Ginger Ch. 01

by Ms_Allison on May 12, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consisten...

Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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Lisa at Last

by PeggyBuxton on Feb 7, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Lisa had dressed casually for the drive to visit her mother. Regardless, she was as stunning as ever. There had been some plastic surgery, but not much, mostly modest implants. Yes, her left leg had been amputated, too. She had considered that cosmetic, but she would tell people a...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Backwards in High Heels

by thrillerauthor on Sep 15, 2017
Transsexuals & Crossdressers

I'm told that when I was two or three, my mother dressed me as a girl and took me trick-or-treating with my older sister on Halloween, but I have no recollection of the event. * * * Fast forward ten years, when I was on the brink of puberty. For some reason which I will never understand, I developed a fixation on trying on my mother's high heels. One nigh...

Quarantine Glory Hole

by secondsamuel on Jul 14, 2020
Transgender & Crossdressers

Author's Note: If you like my stories, please consider volunteering to edit. I will be having surgery on my hands again soon. This is my submission for the Covid contest so please vote. * I'm not getting my security deposit back. Still, it would be easy enough to fix, assuming I'm not evicted immediately for taking off my door and turning it into a transp...