Chapter 1

All my life I wished I were a girl, thought of myself more as a girl than as a boy. Ramona was the Beverly Cleary character I identified with. When Star Wars came out other boys my age formed two camps, one wanted to be Luke and the other wanted to be Han. I wanted to be Princess Leia. From Uhura to Laura Ingalls, no matter the story, I was one of the main girls.

My two best friends were girls, Carrie and Stacy. While the boys got together to play with Hot Wheels or action figures, or do something sports-related, I would be with the girls and their Barbies or My Little Pony. I did have some Barbies of my own along with some of the old-style Star Trek action figures that were as big as a Barbie and I mixed them. Captain Kirk was married to Barbie, and I was Barbie.

I dressed as femininely as my parents would allow and tried to grow my hair long. That they would not allow. I could act like a girl to a large degree but I had to look like a boy. I found one little loophole to that, thanks to my brother Steve.

He wasn’t even trying to help me. If anything he wanted to dick with me, as older brothers often do. When I was six he said he really wanted to be Peter Pan for Halloween, and I should be Tinkerbell. Before I could even say anything he was selling our parents on the idea of how cute that would be, my little Tinkerbell next to his Peter Pan. I quickly agreed wholeheartedly. It was just a cheap costume of a cartoon fairy. But it felt true, it felt right. I could take or leave the wings, but I just couldn’t wait to don that little green dress and bouffant wig.

I checked myself out in my sister’s full-length mirror wearing the dress and wig. I was such a pretty girl. Even back then I had a girlish figure and very nice legs. My legs were my best feature. I found myself just staring at my own legs for a little while. My parents’ seeing how much better I looked as a girl than as a boy and deciding to let me wear dresses all the time was entirely too much to hope for. I simply pointed out how good I looked in the dress.

Dad was a little aggravated and said, “It’s just a costume. It’s only for Halloween.”

His being unhappy about it didn’t take much away from my reveling in it. It was the first time I got to actually dress like a girl. This memory is indelibly etched in my mind, along with the memory of every Halloween costume right up until I was twenty.

The next year my sister Jenny got in on the act. She was Caroline Ingalls and somehow got Steve to agree to be Charles. So I was Laura. This was starting to be a “thing.” So the next year I asked Carrie and Stacy to be Charley’s Angels with me. I even was Princess Leia the year after that. Steve was Chewbacca, and I was Leia. I was nine at the time. It came to be that I could be a girl for Halloween every year.

In the two Halloweens that followed I was real people. Morgan Fairchild, a famous actress who had the same first name as I, was followed by Lady Di, a real-life princess. Without question, the costumes were my favorite part of the holiday. It was the only time I got to dress like a girl. It was even better in the next couple of years because I wore clothes real girls wear instead of specific character costumes. I was a Catholic schoolgirl and then a cheerleader.

I wasn’t the only boy to dress as a girl for Halloween. But I was the only one for whom it wasn’t just a costume. Those dresses felt more genuine to me than my regular boy clothes did. I was also the only one to really look like an actual girl, and not just like a boy in a dress. I didn’t need makeup, I naturally have a girlish face and no visible Adam’s apple. All the clothes did is accentuate the femininity of my body.

I’ll interject some retrospect here before the next part. I was so smart about some things, quickly figuring out on my own what other people learn from others over time. But I was so clueless about other things. I thought I was so unique, the only boy ever to think of himself as a girl and try to look like one. I would have no idea there was an entire community of transgender people for years to come. I thought I was uniquely deranged, but I had made my peace with that. Once a year I would get to be a girl and I intended to do it up right. I thought I was the sexiest girl around when I probably wasn’t even close. The reactions I got wearing dresses and skirts probably weren’t all that I perceived them to be at the time. I look at pictures of my teenage self and I see a beautiful girl, but that is what I want to see. Except in the cases where somebody made it clear with his words and/or actions I don’t really know that other guys were attracted to me. I assumed at the time they all were. I’m sure some were and some weren’t. I’m writing this story from the perspective of how I interpreted things at the time. In short, I make it out that I was overpoweringly alluring and you should take that aspect of the story with a grain of salt.

For a few years I had increasingly caught boys staring at me in a longing way. More often than not they knew who I was but still couldn’t keep their eyes off me. I smiled and pretended not to notice. I was aroused by it. I had learned something about myself, that I could become very aroused and my dick would stir very little or not at all.

The next year I was fourteen. I saw a French maid’s uniform that was a bikini top, a short skirt, fishnets, and stilettos. I just had to wear it. I worked a little magic on my parents and got them to let me. I had to promise to bring my grades up a little and take on some extra chores. The costume was just for a few days and yet the chores were permanent. These conditions were completely acceptable. I started to ask if I could wear the uniform while I did the housework but cut myself short. It just sounded like I was once again asking to wear it for Halloween.

Mom said, “If you agree to our terms you can.”

It came with a two pocket waist apron that was just as short as the skirt and a feather-duster, but no wig. I picked out a wig to go with it. This was Saturday. Costume day at school was on Halloween, the coming Thursday. There was plenty of time, but I just couldn’t wait to check myself out in the mirror wearing it. I put it on as soon as we got home.

When I was in my room with my door closed I would play music just loud enough that I could do things that made noise one would expect to be heard throughout the house but the noise would just blend in with the music and no one was the wiser. At some point I had got my own full-length mirror to check myself out in.

I was amazed by this beautiful, sexy young woman looking back at me from inside the mirror. I already knew I had the face of a pretty girl a year or two older than what I was, and I was sure the maid’s uniform would look great on me. But I wasn’t expecting anything near this great. I was blown away at the way the uniform accentuated my girlish features. I stuffed socks into the top to give myself the appearance of breasts. Other than that I had an elegant, glamorous body. It started curving in just under the ribs to form a skinny waist and curve back out to my hips.

The skirt really showed off the perfect shape of my ample backside. It was giving my legs stiff competition for my best feature. I twisted my body in such a way that I was looking at the reflection of my bottom. I gave each ass cheek a few hard smacks and watched them jiggle. Then I lifted my skirt and spanked myself some more. There was one flaw. Tighty-whities just didn’t look right with this outfit. I decided to do something about that. Panties were the way to go, but my parents would never go for that. I would make sure doing the laundry every week was one of my new chores so I could hide my wearing panties. Once again the uniform was just for a few days but the panties would be permanent.

And then, of course, there were my sexy long legs. I spent a few minutes just moving my legs around and watching them in the mirror. I love the look of them. I even have pretty feet. But those legs. Sensuous, seductive legs for days.

I considered wearing the uniform without the stockings to show off my titillating legs. Then I checked myself out wearing them. Stockings were new to me and I hadn’t realized how good I would look with them on. They hugged the contours of my legs just right. Did I look better with them or without? Tough call. I think a little better with. Then I put on the heels and started practicing walking. It took a while to get the hang of walking in heels. I did have the better part of a week. It was a real challenge and I loved it. And my butt looked even better when I wore the heels. I stared at myself in the mirror some more. Fabulous!

I changed back into my boy clothes and went back to the store by myself. I had some money of my own, having worked as a waiter for the last few months. I never knew there would be such a selection of panties that might fit me. They were just cheap discount store underpants but they seemed exotic to me. I liked the way the fabric felt in my hands and was eager to wear them. I did my best to judge my size by holding them up to me. I bought three pairs of slightly different sizes that day so I could be sure I would get one that would fit. I hurried home with them and tried them on in the mirror.

The panties felt fantastic when I wore them, and they looked amazing on me. But there was still a flaw. I could see the outline of my dick in them. The way to fix that quickly became clear. We kept gauze and medical tape in the house so I decided to do what I now know is called tuck and tape. I experimented with it a little and came up with a way that worked. Then I just stared at myself for a while, taking in how tantalizing I looked wearing nothing but a lacy pair of panties. I was ready to work it. Then I checked myself out in the entire outfit again. So beautiful and tantalizing. I lifted my skirt again and gave myself as hard of a hand-spanking as I could. My ample derriere looked just right bouncing and jiggling in those panties as I spanked it. I was so turned on I was moaning but I still didn’t get hard. I could get myself hard, but it required several minutes of playing with my cock while thinking about cocks. I knew I was going to be very aroused wearing this out in public, and I also knew my dick would stay safely tucked away. I couldn’t wait until Thursday.

It finally came. As it happened I lived close enough to the high-school to walk there. It was unseasonably warm that fall, I didn’t even need a jacket. I caught a few grown men staring at me with lust in their eyes as I walked to school in that maid’s uniform. It turned me on. I had always been attracted to both men and women but especially men. When I saw a good-looking man I would fantasize about sucking his dick and/or being fucked by him. For the last couple of years it seemed like some of them were thinking the same thing. This day I knew these guys were. I would have liked to flirt with my eyes some and blow them kisses, but anytime I looked back at a guy he would get embarrassed and look away. Oh well, I enjoyed the attention nonetheless.

I had reached school grounds and was heading toward the door when I was approached by Todd. Todd was a senior, captain of the wrestling team, and fine as hell. He wasn’t wearing an actual costume, just his wrestling uniform, a tight-fitting singlet. I loved the way it showed off his muscles and tight butt. You could even see the outline of his dick in it. I found myself gazing at his dick, and I knew he was aware. Oh well, it’s not like it’s the first time he’s caught me looking.

We were in that gray area where we were not mere acquaintances but not friends either. One might even think we were adversaries with the way he talked to me sometimes. Just the day before he had caught me looking at his cock in gym class. He had these sexy little gym shorts that were as tight as his singlet. Why would he wear those if he didn’t want people looking? His voice didn’t sound very angry, but he called me a “damn fairy” and said the next time he saw me he was kicking my ass. The only physical contact we had had was an occasional high-five. He never kicked my ass, only threatened to. This day he came right up to me and started talking to me.