Stories Of Sissy Cross Dressers And Black Masters Stories

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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...

My Accidental Orgy

by usmclass on Sep 16, 2017
Transsexuals & Crossdressers

If you don't enjoy stories about oral sex, transwomen, sissy sex, or orgy situations, then you need to check out the Reader's Digest website, because that's all here, and a bit more. ***** Hi! I'm Cassandra. Growing up in the 60s and 70s (in an Alaskan logging camp no less) I became very familiar with men's magazines and Penthouse Letters. Before I move...

A New Adventure...

by johnjinglez1 on May 16, 2018
Transsexuals & Crossdressers

I saw someone begin a "diary" of their experiences as a sissy on here recently and it inspired me to give it a shot myself. The following will be true stories from my past starting from the first time I ever hooked up with a Tranny / Cross dresser / Sissy. First things first, I consider myself to be a straight male; despite having had sex with all of the a...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

A Cross Dressers First Time

by webbyhose on Sep 13, 2017
Transsexuals & Crossdressers

I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour. Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Cross Dressing: A Hypothesis

by Da_Vida on Sep 16, 2017
Reviews & Essays

First as a young adult and then as a psychologist, I read extensively in an attempt to find an explanation for my cross dressing behavior. Several psychological hypotheses have been proposed in the literature but I did not find any of them to be compelling. While I don't think it is an explanation for cross-dressing, one hypothesis that resonated somewhat...

Being a Sissy for Viv Ch. 03

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

I awoke slowly, enjoying the warmth and comfort of the bed and thick quilt. My mind was slowly trying to separate half remembered dreams from reality. Pink panties. A lacy bra. Viv's breasts. Excitement. Embarrassment. Suddenly my eyes were open as the catalogue of disjointed dream images slotted into the reality of the previous evening. Even as the memori...

Pinky's First Shopping Assignment

by Pinkytoes66 on Sep 14, 2017
Transsexuals & Crossdressers

Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental. ***** I just got home late at night from a rough day of work. I tossed my jacket on the kitchen chair, kicked off my shoes, got a beer from the fridge, and decided to sit down at my computer to check my messages before tur...

Black Cross Dresser Chronicles

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

What's up people? My government name is Omar Woodson but you may call Madame Orillia. The Black Canadian cross-dressing diva extraordinaire of metropolitan Toronto, Ontario. One of a few outspoken Black cross-dressers in town, and definitely one of the most wickedly fun and entertaining. Lots of Black men like to wear wigs, skirts, nylon panty hoses, bras an...