Chapter 2 - Catalog Shopping

When I started to get interested in bras and girdles I was pretty much out-of-luck, no sister and my mother was considerably larger, but back then the bras went for $1.49. I could actually buy that stuff and try it on!

You have no idea how radical that thought was back in the early sixties. In these days where crossdressers are a staple of afternoon TV, gay marriage is legal in all fifty states and Tumblr has a plethora of crossdressing photos for the world to view, it's hard to imagine how isolated a guy who wanted to wear girl's clothes felt back then.
Virginia Prince had just recently gone public, but I wouldn't learn of her and the world of crossdressing for many years to come. I wondered if I were the only boy who felt like this, but I just wasn't able to figure out how to learn if anyone else wanted to wear girl's clothes without letting anyone know that I wanted to wear girl's clothes. No one had to tell me explicitly that such feelings were wrong, that just soaked in through the culture.

I dithered for several days, constantly coming back to that colorful ad with the moons and stars, until another colorful ad caught my eye.

That did it! I transitioned from dithering to planning. Having tried and failed to wear my mother's clothes I was very aware of sizing. Fortunately all the catalogs had size charts in them. Naturally my body shape didn't conform to those charts. With the help of the cloth tape measure from my mother's sewing room I measured myself in the places shown in the catalog and figured out my sizes, choosing a B cup because that was the smallest they had and I certainly had nothing of my own to contribute.

I was so naive that I didn't even consider filling the cups, that would come much later. I also picked the open bottom girdle because it was obvious that the one with the legs would be uncomfortable with my male anatomy. Not that I was all that big, but I sure wasn't built for a girdle with legs.

I grew up in a small town an hour's drive from anything that could be called a big city. Remember, this was before the Interstate system was fully developed and the roads were less than stellar. These days it takes twenty minutes for that drive, but I don't live there any more so that's just another of my endless asides.

I carefully filled out the order form and was briefly stuck at the address line. Our mail was delivered to a box in the post office, so that's what I used. Since one of my jobs was to pick up the mail on my way home from school every day I would be able to intercept my precious package without my parents seeing it.

With the form filled out I got a ten dollar bill from my savings and headed for the post office. There I purchased a money order for the correct amount and added it to the form, sealed the envelope and put the stamp on it. I was excited to watch the envelope slide down the slot and start on its way to Sears, Roebuck and Company.

Then the waiting began. It wasn't like these days, when you can click your mouse on Amazon and get your stuff the next day. It took three whole weeks! for the package to arrive. Week one wasn't too bad, I knew it wouldn't be instant. Week two was hopeful, maybe it would be there today. OK, maybe tomorrow. The third week was almost desperate. Would it ever get here? Nothing again today! Come on!

Finally, there was something big in the PO box on Thursday. It's here! It's finally here! I put it reverently in my bicycle basket with the rest of the mail and pedaled as fast as I could to the house.

Noooooo!!!!! It's Thursday, mom's home. How could she do this to me? My new clothes are here and I can't put them on!!!!!

Alright, pardon the italics and the exclamation points, but I was thirteen years old. Everything is dramatic to a thirteen year old. Everything is unfair. The world hated me! Patience was no virtue to a thirteen year old crossdresser with his first bra waiting to be worn. So I stashed the package in the garage and went in the house.

I should have known my mother would instantly detect I was upset. Until the day she died I couldn't hide anything from her. Sherlock Holmes would have been overjoyed to have her as an assistant, unless she took over his practice and left him standing outside 221B Baker Street with a confused look on his face, wondering just what the hell happened.

I was still thirteen years old, so I tried the usual standby of "Nothing!" when she asked what was wrong. I damn well knew from experience that wasn't going to work, but I was stubborn and tried it anyway.

It didn't work.

"Come on, honey. With that long face I know that it's not nothing."

Just how did she manage to make her voice sound exactly like mine, anyway?

"Really, I'm fine, Mom."

"And I'm the Easter Bunny. What's so horrible that you don't want to talk about it? You don't have a girlfriend so you couldn't have had her dump you."

That's Mom, she had a way about her.

"Awww Mom!"

"Give, Conrad. There's something bugging you."

Some writer I am. I just realized that I've been writing this story for quite a while and never told you my name. Conrad M. Cobb, at your service. Corn Cob to my alleged friends. Is it any wonder that I'd rather be a 'Connie' than a 'Conrad' with that nickname?

So I tried an end run.

"Have you ever wished you could be someone else?" I asked.

"I suppose I have. When I was a little older than you are now I wanted to be Sonja Henie, the figure skater. I just loved the skating costumes she wore, with the daring short skirts. Figure skaters before her mostly wore long, black wool skirts and did pretty tame routines. The stinking male-chauvinist judges thought it wasn't proper for a woman to show her legs or - heaven forbid! - cross her legs in a routine.
"She blew all that away and I would have loved to be her out on the ice. Of course we didn't have an ice rink and I fell flat on my face in roller skates. When I finally had access to an ice rink I worked my little heart out to become the next Sonja Henie. Every once in a while I still remember that dream."

"I never knew that, Mom."

"There are depths to your old Mom you never plumbed, eh kid?"

"I guess."

"You sound so positive. So what's your dream, kiddo?"

Could I tell her? I was halfway there after hearing about her dream of being a figure skater. My feminine dreams were rather formless at that point, and I couldn't quite get over that 'you'll think I'm a freak' barrier.

"I don't know, Mom. Just sometimes I think I should be someone else. I don't know who and it doesn't make any sense. I can't really put it into words, just sometimes I think I should be someone else."

"You're not alone, Con. You're at an age where you're trying to find out just who you are. So try on some different yous and see how they fit. I wouldn't go for Humphry Bogart or John Wayne, though."

"Sonja Henie, maybe?"

"Now that would be different. You want I should start giving you ice skating lessons?"

"I don't know. How would I look in a short skirt?"

She took a step back and looked at me.

"Now that you mention it, I think you could pull it off. You might actually look cute in Sonja Henie's tutu. At least if you didn't fall flat on your tush-tush.

"Mom!"

So now you know. If you ever listened to Click and Clack, you know they used that line a whole lot. But my mother said it first - about me, her son! She was a generous soul, so I'm sure she wouldn't begrudge it to them.

But really, mom thought I wouldn't look bad in a skirt? Wow!