Chapter 4 - The First Time

It's really hard to pay attention in class when you're distracted. School was pretty easy for me, I enjoyed learning and liked to unravel puzzles. Math was OK, history was fascinating and I loved science. About that time I started to figure I could do without gym class. Not that I didn't like exercise, but I got plenty of that on my bike. It's the posturing and jock idiots that got my goat.

Not that anyone reading this would be surprised that I was less than enthusiastic about macho stuff. I held my own and a couple of the assholes found out I wasn't quite as wimpy as I looked. Short doesn't mean easily pummeled. Actually, being able to read body language was a real advantage in a fight. If you could predict what the idiot trying to pound you was going to try next I would not be where he expected me to be. I was a quick little bugger, and more than one bully found himself tripping over my feet.

Not that that was the problem on that particular day. No, it was 'The Talk' and ice skating and tutus and bras that had my head in the clouds. Mom & Dad wouldn't be home until after five, so I could try on my new pretties. On one hand I really wanted to see what a bra and girdle felt like; on the other hand I was almost afraid that I would like them too much. What was I going to do if they felt as good as I thought they would?

When that wasn't occupying my mind, visions of spinning around on ice skates in a tutu took their place. I really don't remember how I made it through that day.

Somehow I made it home without running into anybody and parked my bike in the garage. I dug out the package from its hiding place and took it to my room. Off came the clothes and I opened the package. The bra came out first, so I tried to figure out how to put it on. All those pictures showed the bras already on someone's body, but how did you actually get them on your body?
Well, your arms obviously went through the straps, so that's where I started. The darn thing didn't fit over my shoulders, so eventually I noticed there were adjustments on the straps. Being the early sixties, the adjusters were still on the front of the bra, so I extended the straps and slid the bra over my arms. None of the pictures in the ads showed the back of the bra, but it didn't take a genius to figure out how it should work.

Then came the frustrating dance as I tried to match the hooks together behind my back. It took some time, but I finally succeeded and looked in my mirror. Cool! I was actually wearing a bra! And it felt just as good as I had imagined. Looking in the mirror the front was kind of floppy, so I played with the adjusters until I felt the straps tighten on my shoulders.

The girdle wasn't anywhere near as hard to figure out, just step into it and zip up the side zipper. The only problem was that it was tight on my tummy and far too loose farther down. Studying the pictures in the catalog I finally realized that real girls had hips and I didn't, so the girdle just didn't fit right on me.

I hated to do it, but I took the girdle off and tried the garter belt. That fit OK, but since I didn't have any stockings the clips just hung there and tickled me when I walked around. I guess there's more to dressing like a girl than just wearing a bra.

Eventually the first rush of pleasure at wearing a bra faded and I noticed that wearing a bra was kind of pointless unless you had breasts to put into the bra cups. Well, not quite pointless because the thing felt so good, but there had to be some way to do something about those empty cups. So, like all novice crossdressers, I set about finding something to fill the cups. I won't bore you with all my experimentation, but some cotton batting (this was way before fiberfill was available) from Mom's sewing room did the job.

I can't tell you just how looking in the mirror and seeing a girl looking back made me feel. I was riding on the wind, flying above the clouds, mistress of all I surveyed. This was exactly who I was supposed to be, how I was supposed to be dressed, I had found whatever was missing in myself. Pardon the hyperbole, but it was necessary. That day changed the course of my life. Looking back from 57 years in the future, the feelings and the joy still shine in my mind.

I sat at my desk and did my homework dressed only in my bra and garter belt. The feelings were distracting, but I felt far more creative and alive as I did my homework. I was so enthralled about the whole thing I almost blew it - Mom and Dad would be home soon. Taking one last look in the mirror, I finally noticed the girl there had a brush cut and a small but noticeable penis. I resolved to let my hair grow, after all there were a lot of guys starting to wear long hair, the hippies were all around us.

What to do about that penis was a bit more difficult. It finally occurred to me that all the models in the ads were wearing panties, pink ones and blue ones and white ones. At least wearing panties would hide the fact that I had something girls didn't.

I could picture the ladies wear section in the Woolworth store, with the rack of panties right next to the rack of stockings, and you had better believe I had noticed them and tried to be cool while looking at them without anyone seeing I was looking. I saw them every time I went into the store to see Mom, and that was just the problem. Mom worked there; no way I could buy such things even if I could work up the nerve to do it.

I guess you can see why I'm so good at maundering as an old fart, I was perfectly capable of getting distracted starting in my teenage years. It was time to put away my new clothes, but just where could I put them? I didn't want Mom to find them when she did the laundry, so my closet and drawers were out. So was under the mattress, Mom found some stuff I thought I had hidden there a while back, so what now? Then I remembered a loose board in the hall closet that you could take up to get at some plumbing. I found that when I was about eight and thought it was so cool to have a hidey-hole like that. Nobody goes in there - perfect!

I was dressed in my normal clothes and my heart was almost beating normally by the time my parents got home. I even had time to read some of the ice skating books.