Beginnings

The usual preface: All characters are 18 or older. Comment are always welcome. Thanks for reading!

I never minded that much, when I was young. Yeah, I was shorter than most, thin, but it seemed pretty normal. It wasn't until high school that classmates turned out to be pricks. I had reached my topout height of 5', 6", and still thin. So, the bigger, jock types took it upon themselves to label me a "sissy".

Honestly? Why? I liked girls, a lot. The fact that they didn't like me, except as a friend, shouldn't change that.

I had ALWAYS liked girls. I got my first kiss on the first day of school. Unfortunately, it was the last one for many years. But, I scanned clothing advertisements, and later on, the internet, for pretty, sexy girls. I was most intrigued with girls in dresses and skirts, and high heels. Their legs looked SO good. (And this was before I realized where those legs met, paradise)

Anyway, suffice it to say, High school was no fun. I did ok in my classes, and had a few friends, but, they were in the same boat as me: friend zone material. At least once a day, generally more, some jock would make crude comments about "bet you'd like to suck this dick", or "shut your cum catcher, sissy", or something similar. Eventually, I'd gotten pretty much immune to it. EXCEPT gym class. God, did I hate that. Especially having to undress, and get into our T shirts and shorts,for whatever torment activity the coach could dream up for us. THEN, there was the showers, and dressing after. I was constantly reminded of my small penis, or my "cute ass." No guy wants to hear that. I can't count the times assholes would spin their towels, and 'pop' my legs or ass with them, leaving a welt. I have teared up, but never let them see me cry, though. I wouldn't give them the satisfaction.

If ONLY my folks had enough money to send me to a private school, I imagined, I wouldn't have to endure this stuff. But, they didn't. We just scraped by.

One day, walking home from school, there was a huge pile of furniture, household items, and clothes strewn in front of a house, very close to mine. Apparently, the people living there got thrown out, and never came back for their things. I started rummaging through things, hoping to find something valuable. I did find an MP3 player, and a couple of video games, and more clothes. Most seemed to be for a large guy, but there was a suitcase, and fairly large box, of women's clothes . Hmm, wonder if Mom would like them, if they fit? They obviously were in good shape, clean, folded, as if packed to take, but forgotten. I ran home with the suitcase, and came back for the box, and rifled through other boxes, hoping for more valuables.

When Mom got home, I told her what I found, and she picked up a few things and thanked me for the thought, but these things were too small, and said we should donate them. I took them to the half basement, and didn't think much about it. That night, I dreamed that I was getting dressed for school, but was picking out things from the box. It seemed completely normal, in my dream, and it wasn't until I woke that I blushed, and wondered WHY I had such a dream.

Curiosity got the better of me, and that afternoon, I went to the basement, and started looking more carefully at the box and suitcase. Mom was right, she'd never fit in these clothes, and probably wouldn't wear them anyway, as the dresses were shorter than anything she would wear. There were a couple of pair of sexy high heels, lacy bras and panties, blouses, sweaters. I tried to imagine the girl, but could not remember seeing anyone in the neighborhood like that. In the pocket of the suitcase was a bag of makeup, and 3 pair of stockings. You know, the kind that stay up. I found myself getting hard, thinking about the mystery girl.

I went back to the discarded pile, because the garbage trucks weren't due to run until tomorrow. As I explored the random boxes, I found some envelopes, addressed to Valerie Evans. That must have been the mystery girl. I went home, and looked through my school yearbook, hoping to find a picture of her, to no avail. I'm not sure why I spent so much time on this, but found myself going down to the basement every day, reexamining the clothing. Fondling the lace and satin panties got me excited, and I jerked off to them, while imagining a beautiful girl in them, doing it to me. Rubbing the soft fabric on my face would get me so hot, I'd shoot cum several feet, and I'd have to clean it up, because I didn't want to be discovered. It got so bad, I snuck a pair of panties to my room, so I could press them to my face as I lay in bed. One night, a crazy thought struck me.

What would it feel like, to try them on? I made sure my door was locked, and slipped my boxers off, and very slowly pulled them up my legs. Holy Smokes! The feel against my butt, and crotch was unbelievable! It was all I could do NOT to rub one out in the panties, but I didn't want to ruin them.

Well, I felt myself going down a rabbit hole,because it was only a couple of days later that I reasoned, if the panties felt so good, maybe the other things would, too. I got up the next morning, dressed like I was going to school, walked down my street, but went to the house where the girl had been evicted, and waited until I saw my mom and dad leave for work. I then went back home,and directly to the basement. My heart was pounding as I stripped off my clothes, and pulled up a pair of rose colored panties, and with shaking hands, fumbled with the matching bra. Even though it seemed to fit, I had a devil of a time clasping it from behind. How do girls do this?

Finally, though, I got it, and I fondled the padded cups of the bra. While my initial thought was my hands on the girl's breasts, the soft fabric wrapped around me, cupping my boyish boobs, made me feel as if someone was cupping MY boobs. What a rush! Pleased with myself, I started pulling dresses from the box, holding them against me to see what might fit. This girl HAD to be about my size. I chose a burgundy dress and put it over my head, and eased it down. It was snug on top, and flared out at my hips. I smooth it out, and was thrilled at my success. I almost ran up the stairs, to look in the full length bathroom mirror, but thought, shouldn't I have shoes, too? And, wait...the STOCKINGS in the suitcase. Could I? Why not? No one will know, except me. I hurriedly tore open a package and felt how soft , smooth, and delicate they felt. I sat down, slowly working the stockings up each leg. OMG! I thought the panties were exciting, this was bliss of another dimension.

I sat there, wiggling my toes in the stockings, admiring my legs, as if they belonged to someone else. I was smiling so big, my face hurt. I reached over, pulled out the 2 pair of heels, and picked the ones that looked best with the dress. They were pink, with about a 3 inch heel (I didn't measure, just guessing, but definitely taller than any mom wore.) I slipped them on, strapped up my ankles, and slowly stood.

Whoa! This was different! I was on my tiptoes, balancing myself. I could feel the difference in my posture, my butt seemed to jut out more. I started with baby steps, and almost turned my ankle, a couple of times. This looks so easy, in the movies, girls walking, even running, in heels? Wow, new respect.

But I DID love the view. I wasn't seeing me, I was seeing a girl , from a birds eye view. My curiosity finally got the better of me, and I made my way up the stairs, holding the rail tightly, so as not to go crashing down. I made it to the top, and even though I walked awkwardly, I LOVED the sound of the heels clicking on the floor. This new game was the best thing ever. I stood before the mirror, and could not believe the sight. From the neck down? I was hot. I started flicking my hair around, making it fuller, to get more of a girlish look. Hmm...It was long enough, could I style it? I leaned closer. Guys were always teasing me about being girlish, a sissy, COULD I look like a girl?

There was a bag of makeup in the suitcase, hmmm.