The Most Painful Years

Junior high school was a miserable time for me. My father, with whom I lived, got remarried to a woman with two kid, one older and one younger than me. We moved, so I ended up at a different school from all my friends.

There was a girl named Natalie. She was skinny, a little taller than average, had long brown hair that needed more attention that she gave it, and wore glasses that I could only describe as awkward. She was in my math class and my English class.

I would probably not have noticed her at all. There were prettier girls on campus and even in my classes. But she sat one row over and two seats ahead of me in math and two rows over and one row ahead of me in English, so she was always within my range of view. Of course, other people were in my range of view as often or more, including a girl named Leslie who will come up later.

But then one day Natalie came to school wearing tight, dark brown Ditto jeans and a pair of brand new knee high boots. This was a look I loved. The boots were an orange-ish brown. They had a medium height wedge heel and fit her leg snug. She would stand in those jeans and boots, as tight and trim as a military uniform, and I would get an erection.

I lusted after her so much that it ached. Even when she wasn't wearing those boots, I now wanted to be around her.

But, of course, I had my own issues. I was painfully shy, tall and scrawny, with an acne problem and long, scraggly hair that I neither combed nor washed nearly often enough. While I have been told that I am reasonably handsome now, in a Bill Pullman sort of way, back then the ugly duckling had a good chance of scoring just by being compared to me. So I pined away in my awkward loneliness, jerking off to fantasies of her in those boots.

And it wasn't just Natalie. She was the focus of my lust, but at this time boots were very popular with kids my age. A lot of the girls, certainly all of the pretty, popular girls, wore them. I sat there, my unrequited lust simmering, my pants bulging with a hard on, my penis chafing with the wetness of my underware, unable to bring myself to do anything.

And, if Natalie had known my weakness, hand known what drove me, she could have totally owned me. If she had told me to clean up, wash my hair daily, dress better, style my hair, or wear any given cologne, I would have done it in a flash. I was raw material. And if she knew how I would turn out looking in 10 years, she might have considered it. But Natalie was raw material as well. There was little hope that she would have known or cared about controlling or manipulating me, and my boot fetish would have been gross to her.

Two lessons come from this. Both took me a long time to learn.

One: If you are a submissive, eager to be controlled, you have to give away freely some of the keys to controlling you. You have to make yourself vulnerable to a certain degree. It is difficult of course. How do you gauge who should have access to some, if not all, of the buttons that can make you dance like a marionette? You have to know how far you will go to prove yourself initially.

Two: Older women rule. Every woman over 40 who desires it should be given a boy in his 20s to mold, a complete and absolute dictatorship over the man-to-be for 2 or 3 years, to teach him the superiority of women and to make him a fit marriage prospect for a woman his age. I wish I had had a mature, confident woman to guide me into manhood. To this day I adore older women. To submit to a woman in her 40s through into her 60s is sublime. A woman confident in her needs and desires. A woman who is independent and world wise. A woman who no longer feels the need to be clingy, who can let go enough to make her boy toy anxious instead. A woman who has a life, who will never make you the center of her existence, but will treat you as an amusing hobby, an indulgence, as something to wring full enjoyment out of, as a cherished but passing scene in life.

So in a private setting, if a mature woman in attractive boots requested that I get down on the floor and kiss her boots, I would do it. I am mentally prepared for it. I wait for the day when it might happen. Welcome to my little fantasy world.