Thursday, June 16, 2011

Caught in the feminization trap, blogging going out.....

It wasn't long after that first phone session in May of 2008 that Mistress Cassie put me on the femming path and kept me there. The original maid diane was born in July 2008. It was a n assignment from Mistress. i didn't know what a blog was, but i soon embraced it, to please Her. It was a forum to show pictures of a sissy following the instructions doled out by Mistress. Eager to please Her, i ate it first post was an assignment  took from Her sissysalon website. Salad dressing. my own cum on lettuce.

Never out in public dressed as a sissy gurl, it was Labor day weekend when that changed. i got a hotel room, shaved dressed and went out - more than once. It was exciting in many ways. But wearing a skirt in public was another turning point. The feeling of freedom was amazing. Freshly shaved legs covered by silky nylons. The late summer breeze blowing up my skirt, the swish of my gurly walk in high heels. It was overwhelming. Awful in a way. i was totally self conscious, afraid, excited confused all at once. But i still remember that feeling of being outdoors, in the daylight, dressed. The freedom was more than not having slacks on. i was free of hiding indoors. i went out a few more times after that weekend. But nothing will ever compare to that first awakening of my inner female self.

Skirts are made for outdoor wear i think. The risks involved are still there and i got a hotel room for a reason. Fear of discovery still keeps me from going out. There's too much at stake. But, sometimes i just couldn't resist. Almost three years later that first day out still burns brightly inside of me.

Then there were the two visits to Macy's, the Macy's make up counter. First time, an eye treatment and a valuable lesson in how to apply eye make up. i was dressed as a guy. The 2nd time i was dressed properly, all gurl, and got a total make over with another young Woman standing by as an interested observer. i believe that was in

More tto come.

sissy maid diane


  1. Maid Diane- Ooh, such a pretty pic of you, and a great story heading down your path... :)

  2. I remember you telling Me about the man who saw you, dressed, in the hallway of that hotel... and how excited you were that he looked back, over his shoulder.. you turned his head.... ... a sissy turning point. No Going BACK.

  3. Hello Weave,

    Thank you - i'm glad you enjoyed my pics and the story. It's fun recapping the last few years.


  4. Hello Mistress cacssie,

    You have an amazing memory, among other qualities. Yes, i was wearing 6" pumps and a pencil skirt. Yes, i was excited, i had just come upstairs from the park bench out in front of the Hotel, which i included as a pic in this post. That trip was a sissy turning point. :o)

    And, thanks to You, there were many more to come.


    sissy maid diane