Wednesday, February 2, 2011

A Sissy Girlie-Boy -- part 1

Ever since Daddy left, I knew that things have been difficult for Mommy financially.  She was working two jobs, but still there never seemed to be enough money in the house.  Mommy was becoming desparate and depressed.

But that was before Halloween.  You see, for Halloween, I girl I knew from school and I dressed up as Bonnie and Clyde -- only I was dressed as Bonnie and she was Clyde!  I wore a white flapper dress, complete with a long blonde wig, lots of make-up and big fake boobs.  Well, our costumes were a big hit.  We even won first prize in the "couples costume" category at the High School Halloween party.

When Mommy saw me in my Bonnie costume, she seemed really shocked.  "Oh my!" she gasped when she saw me.  "You really look like a girl!  Your legs are gorgeous."  And then after a minute, she said, "Hmmmm, this isn't the first time you've dressed up like a girl, is it?"

Well, she was right, but I denied it.  For years I had been dressing up in Mommy's clothes whenever I was alone in the house.

The next weekend, Mommy asked me again about dressing up as a girl, but this time she wasn't so gentle about it.  "I know you've been getting into my things and playing dress up everytime I leave the house.  It's true isn't it?  You are really a little cross dressing Sissy, aren't you?  Well since you like wearing dresses so much, I've come up with an idea for you to prance around in dresses AND make a little extra money for the family."

I tried to protest, but Mommy wouldn't have any of it.  She had me dress up as a girl again, wearing the same white flapper dress and high heels I had worn on Halloween.  Only this time, she didn't let me wear a wig or falsies and she put only a little make-up on me.  "Mmmmm, yes, that's the look we want," Mommy said.  I looked sort of girlish -- but it was pretty obvious that I was really a boy.  "Why am I dressed up like this Mommy?" I asked. 

"You'll find out soon, sweetie,"  Mommy replied.  "Just practice your girlie walk again for me."

After a couple of hours of practicing how to sit and walk and talk girlishly, Mommy ordered me to get in the car.

We drove all the way downtown and went into the area with all the warehouses.  I had never been in this part of town before.  We parked in front of a bar called "Frank's Hideaway."  It looked like a sort of dangerous place.  It was still early and the bar didn't look open yet.  Mommy told me to get out of the car and go into the bar.  

"What?!?" I screamed.  "I can't go into a bar dressed like this!!!  I want to go home!"  That's when Mommy slapped me.  "Get out of the car right now, you little Sissy," she snarled.

Mommy literally dragged me into the bar.  "Hello Frank," Mommy said to the man behind the bar.  "This is my son Jack...or should I say Jackie, the one I told you about on the phone yesterday."

"Of course," replied Frank as he looked me over.  "Yes, he looks great; just the way I hoped he would.  I always wanted to have a girly-boy like him for the bar.  He'll do well here.   But he'll need some new clothes."

"I know," Mommy replied.  "Don't worry, I'll take care of that."

"Now Jackie," Frank said.  "Let me tell you how things work around here..."

To be continued...


  1. Nice story. Can't wait for Part 2.

    I love the picture. The dress and heels are exquisite. Very pretty young lady too! '-)

    I remember when I would dress in my mothers clothes when ever she was out. I guess she knew but never was overt or confrontational about it. Oh, she did give me 'tips' on makeup and color coordinating though.

  2. oh! I love it! What a haircut so sissy! And the dress is wonderful. Beautiful legs and marvellous shoes. The girl is going have a prize. Probably in flesh...

  3. Miss Linda, The photo is perfect. You are the best when it comes to captions that feature sissy humiliation. I love the focus on retro fashions.The best part about your work is your attention to detail. Showing how a small mistake can change the lives of our little sissy's forever is a real talent. Thank You

  4. Nicely written. I see you've been busy. I think I'll add you to my blogroll

  5. Sissy is going to now be contributing to the household income, that way mommy won't have towork so hard. Sissy like to dress in mommies clothes anyway so at least this way it makes some contribution.

  6. What is with this " sissy-bitch" Love the dress, Still hate the shoes?" White Heels, Sweetie!" Holly B. Or I will dress you up myself!

  7. Isn't he gorgeous. Dress a girlie-boy at the right time and he never stops.