Chapter 4 – Preparing for a shopping trip with Mom

The rest of the week turned out to be pretty normal. School, homework, video games, and family dinners. Well, that and the decision I was wrestling with. On Saturday, after breakfast when my brothers went out to play in the back yard, and my Dad went to have some specialty engine modifications done on his antique car (a 1968 Plymouth Fury), I decided to help my Mom clean up the dishes.

“Hey Mom, I can’t stop thinking about what it would be like to dress up as a girl completely, and I think I’d like to give it a try.”

“Really, Mikey? So you want to present your book report in character, as Annie Oakley?”

“Yeah!”

Mom’s face lit up with a big smile, and she leaned over and kissed me.

“After your baby brother Ben was born, your father and I knew we weren’t going to have any more children, and I always wanted to have a little girl to share some things with that typically pass from mother to daughter. We’ll have some special time together, just for me and my oldest.”
I naturally had mixed feelings about this. On the one hand, I was really starting to notice girls in a different way from ever before, and was all kinds of curious about them. On the other hand, I had no desire whatsoever to give up being a boy and spending time with my buddies on the hockey team. Mom seemed really excited about this though, and her energy was quite infectious. That got me just as amped up.

“OK Mom, I’ll do it!”

“Wonderful! I think you’re really going to enjoy this. This will be an experience that will give you a perspective on all kinds of things that very few boys ever get to benefit from. When you start dating girls, I think you’ll have a new appreciation for them too, that will be well beyond most other boys your age.”

What in the world was I getting myself into?

“Why don’t you go take a shower and get dressed. But before you get fully dressed, I need to take some measurements, so just put on a t-shirt and your undies. Then we’ll take a shopping trip and get you a nice biography of Annie Oakley and some of those Star Wars books that you like, along with a few other things we’ll need to make your costume!”

“Right Mom! I’ll let you know when I’m done.”

At that time, I stood about five feet tall and weighed around a hundred pounds. I took a shower and got dressed in my underwear and t-shirt so she could measure me, then called Mom in to let her know I was ready.

She came in with her measuring tape and rolled it across my arms, legs, chest, waist and hips, double checking each.

“Let’s see…26 inch waist, 30 inch chest…we’ll need you to try on a few different things to get the sizing just right but I think you’ll be a perfect size 2!”

I really had no clue what that meant and why she seemed so excited by that idea, and stared at her somewhat dumbfounded.

“Ok Honey, I’m gonna write these down and then we’ll head to the mall!”

I threw on a pair of jeans and a hoodie, and caution to the wind. Off we went!