Each of us who crossdress has a wonderful, beautiful memory; the memory of the first dress we ever wore. It may have been as a child, or as a teen. Some of my friends on the internet never even tried until they were middle aged or older! But the memory of that first dress is a precious one.

For myself, it was at the tender age of 9. And at the urging of my mother.

First, let me give you some background about myself, about my family, and about the time.

It was 1960. I lived in Northeast Philadelphia and attended the local Catholic school. Our neighborhood was a typical densly-populated row-house development of honest, decent, working-class folks. Although predominantly Catholic and exclusively white, we had a certain ethnic diversity of Italians, Irish, Poles, Germans, and others. It was an exciting time for my parents, since an Irish Catholic was running for president and had an even chance of actually getting elected.

Halloween was approaching. For a kid in Philly this meant one thing: CANDY! And thanks to row houses, a kid could cover a lot of territory in a really short time. I was a veteran trick-or-treater by this time. I had gone out to beg candy since I was 3. Mom and Dad would take me to trick-or-treat until I entered second grade. The neighborhood was pretty close, and very safe. Of course, I always had to have a cool costume. One year I was a little devil. Just last year I had gone out as Zorro, complete with black cape and a sword my father had made for me. (Truth to tell, my greaspaint moustache looked more like Groucho Marx than the suave Don Diego, but I didn't care). But for some reason, Mom started talking to me about wearing a dress for this Halloween.

"Oh, go ahead, Billy! Nobody will laugh at you. It's all in fun!"

To be honest, I had conflicting emotions about it. I was keenly aware of the rough-and-tumble world a boy lived in. I was constantly being challenged, and constantly challenging, the other boys in my circle, in an attempt to establish dominance. The last thing I wanted was to be labeled "sissy". That was the kiss of death for a boy. On the other hand, I had a secret curiosity. I kept it to myself for reasons we all know too well. This was a curiosity to experience life as a girl. To wear pretty dresses, to play with dolls, to put ribbons in my hair or fix it in a pony tail or braids, these were stirrings which I held deep within my soul. I was somewhat afraid of letting these feelings out.

So I resisted Mom's suggestions for a little while. But then, my curiosity got the better of me. I agreed to trick-or-treat dressed up like a girl. Mom was pleased.

My dress was a 1920's flapper gown which Mom had worn to a costume party last year. It was too big for me, so Mom took it in. I had to put it on while she marked it for alterations. All the while, my younger sister laughed and teased me. "Look at Billy! He's in a dress! Wanna play with my dollies, little girl?"

Mom would shout back at her, "Stop teasing! This is just a Halloween costume!" This, of course, led to even more taunting. If I hadn't been pinned into that dress, I really would have let her have it! Ah, the joys of family life!

Finally, it was Halloween. The talk in school that day was all about trick-or-treating and what we would wear as a costume. I kept changing the subject whenever anybody asked me what my costume was. I didn't want anybody to call me a sissy. But also, I could hardly wait! The thought of going outside dressed like a girl was starting to really excite me.

Perhaps a word of explanation is needed here. My excitement was not sexual in nature. As far as I knew, the anatomical differences between males and females were solely a matter of waste elimination. Why the Lord gave us different arangements for using the potty was one of those great mysteries of life. Human reproduction was not a matter of great concern for me at that age. Really! I STILL thought the stork brought babies. My excitement was at the thought of being a girl, even if just for this night.

At last, the bell rang. We all filed out in those neat lines Catholic school was famous for. (I would often think, when practicing close-order drill in basic training, that this was something like being in Catholic school. Except the nuns never used the kind of language a sergeant would.) I ran home, eager to get my costume on. It was almost becoming more important than the candy!

"So, Billy," Mom asked, "are you ready to get into your costume?"

"Yes I am, Mom!" I answered. "I want to get out there and get as much candy as I can!"

"Okay," she said, "let's get you dressed." She smiled as I ran upstairs.

First thing, I took off my school uniform (white shirt, blue pants, and a striped tie) and hung it neatly, putting my shirt in the hamper. I didn't realize it, but Mom had more planned for me than just a dress. She brought all the things I would need to wear into my room. This included a slip, nylons, and something I had never seen before. "What's that, Mom?"

"That's a garter belt. You need it to hold up your stockings."

"You never wear one, do you?"

"No, I have garters on my girdles. I borrowed this from Mrs. DellaPia. It's from her daughter Joanie. Now put it on." It felt strange and wonderful. So did the seamed nylons which mom then had me put on. I was starting to enjoy this! Next, she had me hold my arms up and put a slip over my head. This was also borrowed from Joanie. Finally, I put on my flapper gown. It was really cute, a purple dress with fringes all over it.

"Okay, now let's do your hair and make up your face." I could hardly believe it! I was going to wear makeup! I sat down at the kitchen table as Mom patiently brushed my hair into one or those short styles popular in the Roaring 20's, complete with the cute little spit-curls. Then she got out her compact and put some powder on my face, followed by a little rouge on my cheeks. Then, she told me to purse my lips and she applied some lipstick. I was really digging this!

To complete my costume, I wore one of those cute flapper hats and a long strand of pearls. For shoes, I had a pair of ballerina slippers with a hard sole for walking. I guess high heels was too much to hope for. Then she had me look at myself in the mirror. Wow, it was unbelievable! I really looked like a girl! I was so thrilled!

"Billy, you look so cute!" she said, "I'm glad you decided to be a girl this Halloween!" I started to blush. I was not only making Mom happy, I was also fulfilling a secret desire of mine.

Mom handed me a shopping bag for the candy I would collect that night. It was from Lit Brothers, a Philly department store quite popular at that time. Clutching my loot bag, I stepped out into the cool October night.

It felt funny. I had never felt the sensation of cold air swirling around stockinged legs, or the swish of a skirt and slip while walking. It was especially neat to feel the fringe sway back and forth, and the pearls dangle from my neck. I was a little nervous as I went up to the first door. I held my bag open and said "Trick or treat!". The lady at the door said "My, what a cute costume! You sure look pretty!" I said, "Thank you! Happy Halloween!" and moved on to the next door.

That was so cool! As I went from door to door, the folks handing out candy all thought I was really a girl. I was being complimented for my dress, my makeup, everything. Even the kids I was trick-or-treating with thought I was a girl. And I was also cleaning up in the candy department. Some of the people liked my costume so much, they threw in an extra candy bar. I would be in sugar nirvana tonight!

I wanted to see just how much I could fool people, so I walked up to the Martins' house. Mrs. Martin was a friend of my mother, and I often played with her sons. I said "Trick or Treat!" as she answered the door. She also thought my costume was pretty. Then I asked her, "Don't you recognize me, Mrs. Martin?" She looked at me with a puzzled expression. "I don't think so, honey. Do I know..." Then it struck her. "Billy! Billy Smith! My God, is that you?"

I was grinning like the cat who got the canary. "It's me, all right!"

Mrs. Martin started to laugh. "Oh, my gosh, I never would have known! You look so much like a real girl! You sure fooled me!"

"Mark!", she called, beckoning her husband, "come take a look at this!" Mr. Martin came to the door. "Would you believe this is Billy Smith?"

Mr. Martin also started laughing. "That's really great! It's got to be the best costume of the night! Gloria, get him in here! We have to take a picture of this! Billy, that is one great costume!"

Mrs. Martin had me pose by her fireplace, directing me into some cute, girlish poses. She even found a long cigarette holder and had me hold it like a prop. She showed them to mom a few weeks later after getting them developed. I don't know what ever happened to them, but as far as I know they are the only femme pics of me ever taken.

I made the round trip of my block and stopped back home to unload my loot. The night was young, and there was more candy to be begged. Mom stopped me before I left to touch up my lipstick. Then it was back on the streets to work the block across the street.

In all, I worked three blocks that night. Whenever I would meet one of Mom's friends, I would let them in on the joke. For everybody else, I let them think I was really a girl. I even fooled some of my classmates I met trick-or-treating. One of them, Joe McCormick, even told me to get lost because he wasn't going to hang around with a "yukky old girl". Joe, if you are reading this, you finally know who you were talking to that night.

The dream finally came to an end. After my third trip, I was too tired to walk another step. It was getting late, and most people were out of candy anyway. I reluctantly took off all of my feminine things, washed off the makeup, and dived into my candy.

The day after Halloween is All Saints' Day, a holiday for Catholics. We had to go to church, but school was closed. As I listened to the priest drone on in that incomprehensible Latin, my thoughts were on the previous night, my night as a girl.

It would be nice if I could report that this was just the beginning of many such adventures, but this was not the case. The garter belt and slip had to be returned, and my slippers were given to Joanie. After all, I wouldn't be needing them. I think the stockings were just thrown out. As for my dress, it hung in Mom's closet for a few years before disappearing. I never wore it again. But the memories I have of that wonderful night will remain with me forever.

© 1998 Valentina Michelle Smith