Crossdresser Proper Lady Stories

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Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

Six Hours of Heaven

by diablofire on Sep 15, 2017
Transsexuals & Crossdressers

Authors Notes: This is the story of my first visit to an anything goes swingers club in Las Vegas. The night of the story I was one of the first arrive and one of the last to leave. ***** I finally sat down with my wife yesterday afternoon and had a talk with her about my desires to take my sexual desires to the next level and I was surprised what her resp...

Crossdresser Evolution Ch. 06

by pantyhigh on Aug 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. 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 panties. Recap - Crossdresser Evolution - Ch 02 - Getting my wi...

Secret Journey Ch. 02

by DrGonzo124 on Feb 11, 2019
Transgender & Crossdressers

AN: with profound thanks to Personal Deviant. 8 9 8 Suki dreamed of another time and place. A place filled with warriors drinking... feasting...fucking. Another body? His, yet not his own, to judge by the nipple clamps pinching him with a painfully arousing agony and the odd sensation along the length of his erect shaft that had to be a lattice of pie...

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...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Aphora's Mission Ch. 06

by ValoryG on Sep 15, 2017
Transsexuals & Crossdressers

By all accounts, we were saying a final goodbye to Earth. Even though I wasn't close to my parents (my father a doctor and my mother a marketing professional) I figured my mother would miss me. And I would miss them somewhat, especially at Thanksgiving- and Christmas-time. We six didn't see ourselves as the homesick type, and I personally hoped that Aphor...

Becoming Jessica

by Lovely_Jessica on Sep 25, 2017
Transsexuals & Crossdressers

It all started after I told Emma I no longer wanted to have children one day after work on a Friday evening. Over the past few months we were actively trying to procreate after 5 years of marriage. We originally never wanted children, but that apparently changed after her proverbial "baby clock" starting ticking. Don't get me wrong the sex was great and we w...

The Society Ch. 05

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

"I don't think that I'm the right person for this. You need someone more experienced. What if I fuck this up? I'll get my balls snatched right out from under my cock!" I was more than a little nervous watching Serena and Corinna rifle through my closet. "Your balls were snipped off quite a while ago my dear and the woman who owns them has given you her orde...