Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Pretty in Pink Ch. 02

by LeandraNyx on Sep 25, 2017
Transsexuals & Crossdressers

"Well, that's unusual," Susan purred, and the hairs on the back of my neck stood on end. "Our own powerhouse paralegal, all quiet and demure during the sound-off meeting? Now that just doesn't make sense." Grabbing both sides of my chair, Susan eased her obnoxious face into view. Personal space had never been her strong suit. Why god? Why? I asked the heav...

Nothing But Knit

by komrad1156 on Jun 26, 2019
Transgender & Crossdressers

Nothing But Knit *Author's note: Those of you who've read my personal crossdressing stories (those written in the first person) know I have a huge fetish for knit tops—particularly the ribbed-knit variety. I often use the word 'sweaters' for the things I like in a generic sense, but pretty much any form-fitting top that are not sweaters fit the bill quite n...

Becoming a Sissy Maid & Slut Vol. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eighteen: Some New Friends for Chantel. A blissful night's sleep has led me to a wonderful Sunday day off. Master has told me I must accept that special Sunday plans are on the go after 3:00pm but today, this morning awaking at 9:00am I run my routine, enema, shower, put on fragrant body lotion. I then begin a day of dressing just for myself, but al...

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

Changeling Ch. 05

by Michael142 on Sep 19, 2017
Fetish

Continued from Chapter 04, and concluded in this Chapter. Scene is in the townhouse, after David plays maid to Donna and Brenda. Donna and David are alone in the bedroom. ***** David dresses as my maid for a party. David and I made love long and ardently last night with lots of kisses and touches, giggles and intimate talk, and of course ... fucking! W...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

The Role Players Pt. 03

by hollygurl29 on Jul 30, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

Born to Be Ch. 05

by DamienDeath20 on Feb 10, 2020
Transgender & Crossdressers

A.N. Back for some black on white! :D If you want more stories by me look at my profile! All you need to know is there :) JUST A FUN FACT also, this is not the final chapter, not at aaaaaaaaaaaaall, there's maaaaaany more to come. You'll see why I say that at the end lol, just again letting you know ahead of time, no reason to worry. The Following Co...

And it has Addled her Brain

by kate7891 on Jul 27, 2020
Transgender & Crossdressers

And it has Addled her Brain © kate7891 Giaan Gallagher's leggy stride spoke of purpose and no nonsense. Tourists and businessmen alike saw her coming a mile away, what with her bright red hair, height and 'get out of my way' attitude. She moved at the pace of a bustling city; she dodged her way around those moseying along Melbourne's busy CBD; she crossed...

Just a Girl

by katie_risita on Sep 18, 2017
Loving Wives

My name is Frank. OK, it WAS Frank, until recently, when things...changed. Now, more often than not, I answer to Katie. I know, I know. Yes, I am a guy, technically, but, well...to explain, it's gonna take a story, a loooong story...but not a boring one, I promise! I am a 33-year-old guy from Long Island. I have always been overweight, not great-looking, s...