Crossdressing Brother Stories

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The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

What Craigslist Got Me!

by SissySlutPrincess on Oct 13, 2017
Transsexuals & Crossdressers

I had been crossdressing and playing by myself for years. A simple fun way to pleasure myself and satisfy my love for all things girly. I just needed more being from a small Ohio town made it tough to actually find someone to share this leisure with. Everyone knew everyone so no one wanted to get caught, but me! I decided to check out Craigslist. I posted a...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

Kendra Is Born Ch. 02

by komrad1156 on Sep 15, 2017
Transsexuals & Crossdressers

As the limousine pulled into the Southcenter Shopping Mall parking lot, Kenny's heartbeat quickened. As the driver came to a stop in front of the large "Nordstrom" logo, he felt like his heart might beat out of his chest. On the way there, Kelli informed him she'd done a little bit of reading on the subject of crossdressing and learned there were specially m...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

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...

Everyone has a Freak Flag

by Etaindarcy on May 28, 2019
Transgender & Crossdressers

So for the most part, having sex while crossdressing is a bit of a fetish and once people know you are into it they are now free to share their own fetishes with you. That's where my next life lesson comes in and I have a couple of stories about people doing some surprising shit near me or to me. Around 26 years old, I was now going by the name Amanda and I...