Like Jill
Keywords: Like, Jill,
I wanted to be just like Jill. I don't know why exactly.
When I say I wanted to be like Jill, I mean I wanted to be her intimate friend so badly in third grade that I wanted to become a girl. I dreamt about having pigtails, a pleated skirt, a white blouse and white stockings. I liked those leather shoes she wore too, the plain, dark Buster Brown ones with a leather strap that buckled across the instep.
Jill came to our school in the fall of third grade. Before she arrived, I'd always liked the girls, be I'd never wanted to be one. Geez, I spent most of my time fighting with the guys to see who was toughest during hockey and football!
I guess I was considered cute by the girls, because the older girls would take me behind their houses and want to play "I'll show you mine if you show me yours....". At first, this game scared me somewhat, because I was afraid of getting in trouble. After a while though, I began initiating the game myself once in a while. Once, in first grade, a girl named Susan invited me over to her house while her mother was at work. Susan's parents were divorced, an unusual occurrence for those days, but her mom must have been sexually active, because Susan brought me into her mom's bedroom to play a game that "mommy played". Her mother came home early and found us in bed together. Her mom called my mom, and all I remember is the long walk home, my mother scolding me the whole way. I didn't understand what I had done wrong, but by virtue of being the boy in the situation, it was all my fault. The next day I went to see my new true love at school, only to find that Susan's mom had transferred her to the Catholic school at St. Thomas.
Word got around the neighborhood about my little escapade with Susan. Strangely enough, my new reputation only seemed to affect mothers adversely. Almost every girl in the neighborhood was now curious about what was in my pants that had the world in an uproar. When I went to play at my friend Roxie's house, we traded peeks of each others privates under her doll's tea table. Her big sister caught us, and my mom was called again to come get her perverted son. Hell, the whole show and touch thing had been Roxie's idea!
By third grade I no longer felt comfortable talking to girls. Don't get me wrong, I still adored the hell out of them, but it seemed like everyone's parents regarded me as some kind of sex freak, and it embarrassed me so badly to see adults looking at me that way that I just kept to myself.
Then Jill came along. Jill was a quiet girl who my mother thought was very plain looking, which kind of pissed me off because I thought that Jill was beautiful. I went home every day after school with nothing on my mind but Jill. When I went to school in the morning, butterflies would hover in my stomach if I saw my shy new friend approach. Finally, one Wednesday afternoon (Yes, I still remember what day it was after nearly forty five years), I walked Jill home across the junior high football field, holding hands. We never did anything sexual. It was just, well, love I guess. Anyways, I wanted to make her officially my girlfriend that day. I wrote her a note: "Do you love me? I love you. Check "yes" if you love me and check "no" if you don't. Jill really was shy. I found out later that her father had a drinking problem, which made her very quiet. Jill smiled at me, putting pencil to paper. My heart was somewhere in my throat, about to leap out and dance around for joy, when suddenly, my buddy Doug, who had come along to see me "get the girl" dropped a long two by four that he was playing with on Jill's head.
Jill began crying loudly and ran for her house, dropping the unsigned note on the ground. My heart broken, I watched Jill's mother come out of the back door, eyeing me suspiciously as her wounded daughter ran into her arms.
My heart sank. Now the most important mother in the world, my girlfriend's mother, thought I was some kind of freak too! It couldn't get any worse. Enraged and frustrated at my luck, I chased Doug in a screaming, cursing eight hundred yard dash, Doug escaping unharmed only due to my mom showing up in her car, wondering why I hadn't come straight home after school.
After that incident, I no longer talked to girls. I still thought of Jill every day, but more in a mourning type of way. I made a soft washrag puppet of Jill, complete with a plaid skirt. Every night, when I went to bed, my pretend Jill would be waiting for me under my pillow. I'd kiss her, then we'd talk for hours. When winter came "cloth Jill" and I would cuddle under the chilly Michigan blankets watching frost grow into patterns on my bedroom window.
As I became more lonesome and isolated, I began to sneak some of my mother's clothes that were similar to Jill's...white blouse, plaid skirt, white nylons, stuffed bra.....into the bathroom, one at a time so that my mom wouldn't miss them. I began to play "dress up", locking myself into the bathroom when no one was around. I used make-up too. I could make myself into a very beautiful girl, except for the hair and my big feet. I began getting huge erections when I dressed up, so while undressing, I would flip up my skirt and masturbate. I was too young the first few times that I rubbed myself to cum, so I was surprised one day when I had an orgasm and cum exploded out everywhere. I freaked, worrying that the mess I had made would expose my secret.
The strange thing was that the dressing up came to feel very normal to me, so much so that after a few weeks of doing it I actually asked my mom if I could get my own set of clothes like Jill, grow my hair long and go to school as a girl! That was in 1962, so don't even consider what things are like now if you compare it to back then. Mom freaked, of course. She said that "Only homosexuals dressed in women's clothes, and that there must be something really wrong with me if I wanted to dress up that way". Needless to say, I never discussed the subject with her again. In fact, I avoided girls entirely until high school, when I was "rescued" by my thirty-something art teacher, whose husband was willing to "share" her because he had an old lady on the side. It was the '60's, and anything went.....
Years later, when I moved to L.A., I picked up trannys a couple of times. They were Phillipino guys, and they were very cute. I'd pay them to blow me. One licked my ass once, which got me off, but I never wanted to fuck a guy. I would, at times, imagine myself attracting a beautiful girl home while dressed as a woman, making love to her while we licked each other's pussies and played with each other's long hair. I tried cross-dressing once or twice with an open-minded girlfriend, but I only felt embarrassed afterwards. Still, the thought of looking sexy in something lacy and slinky was often a guilty turn-on in the back of my mind.
These days, I fuck the women that want me, the pretty ones anyways, but usually only a couple of times, and then I don't call them anymore. I like it when they don't really get to know me, because I never, never want to see that look of disgust on their faces the way mothers used to look at me when the rumors of sex came up. Somehow, it usually feels to me like that part of me that desires to be a "little more feminine" will be written across my face if I opened up with someone.
Sometimes I think life would have been better if I would have been just like Jill.
Keywords: Like, Jill,