Crossdresser Proper Lady Stories

104,639 results
Orientation
Length
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Infinite Scroll

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

The Ride of a Lifetime

by CuriousJ95 on Nov 6, 2018
Transgender & Crossdressers

Hi everyone, this is my first attempt at writing. I hope you enjoy and I can't wait to get some feedback from everyone. Please be honest in what you think...I can take it. This is a true fantasy of mine. *** I'm a curious man that is married to a wonderful woman but as time has passed our sex life has diminished quite a bit. We still occasionally enjoy...

From a Husband to a Dutiful Sissy Ch. 17

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Seventeen: Wedding Day and Wedding Night. [November 16.] Life is all a hectic fluster, now one day prior to the wedding of Mikel and myself along with Helen and Alan. Crazy, crazy, crazy, but so exciting... I finally find some time to be with myself. I am in the bathroom, naked only my pink fluffy bathrobe on. I'm going to take time to just sit an...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Crossdresser Evolution Ch. 05

by pantyhigh on Aug 7, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. Though there was still a feeling of shame surrounding it, I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

In from the Rain Pt. 02

by dreadknots on May 21, 2018
Transsexuals & Crossdressers

Well shucks! I got some positive feedback from the first entry, and a couple people were even nice enough to comment asking for another one! Let it be said that I'm not above placating the masses. By which I mean cute crossdressing smut. A little bit shorter than the first one, but I don't really have to introduce the characters too much this time. Don't wor...

Agnes Dourville Ch. 12

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

When the massive shovel at the bottom of the open-pit mine drops its load into my oversized dump truck, I shudder along with the entire vehicle. In fact, the earth itself shudders. I'm being loaded with taconite by one of the largest hydraulic earth-shovels in the world. Wearing panties while doing so gives me such a perverse pleasure.... I gun the diesel e...

Hotwives Ch. 02

by Donna Williams on Sep 16, 2017
Transsexuals & Crossdressers

HOTWIVES II by Donna Williams ((Read the first part of the story in "Hotwives" first)) I was now a hotwife, Vicky was a pseudo hotwife, and John was a sissy, cock sucking cuckold. Everyone got what they wanted, if not more! * * * Once John had fallen asleep, Dave and Rick left as we had planned. When John woke that morning, he found me in the shower. "You...

From a Husband to a Dutiful Sissy Ch. 08

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Readers, I so hope you are enjoying my story here. It sort of allows me to live vicariously through my words as Chantel. This story has been outlined to allow me to write it in an encompassing and linear way. I try not to wing it but to paint a story that is life-like without being boring, well at least I hope it's not. I hope my characters are believable an...

Outed By Ebay

by Marcia_Fredricks on Sep 16, 2017
Transsexuals & Crossdressers

I've been an opportunity crossdresser since I was a child. By the term opportunity crossdresser, I mean whenever there was an opportunity to dress in women's clothes, I did. As a child, and later as a teen living in my parent's home, it was difficult. In college, living in a dorm, it was near impossible. The only time of my life when I had free reign was aft...