When I was a boy, I learned to think of everything to do with women to be forbidden. I feared it, as did all of my peers. It was improper for boys to ever see girls' underwear. There were very strict social norms against boys having anything at all to do with feminine things. This makes sense: as a child, you're still trying to form a sense of identity, and gender is one of the most immediately comprehensible aspects of it. It's like a lifebuoy that we cling to, to assure us of who we are.
So imagine what it must have been like to have to wear girls' tights for a school play, so our kindergarten teacher could have us all dressed like flowers. Now, suddenly, it was ok for boys to wear girl clothes. But deep down, I knew that it was subversive. It was even comical, but not so embarrassing since all the boys had to do it.
I, for one, had tasted the forbidden fruit, and I wanted more. It planted a seed in my head which in a few years' time, when puberty started to hit, would grow like a weed.
It is forbidden for men to wear women's clothes. Those who do are cast out of polite company. It's simply unacceptable, deviant, and perverse. But why?
First, it was pantyhose. They seemed innocent enough, since I had already effectively worn some in kindergarten. But this time, it was more serious. I wanted to. And when I did, it felt so good. I learned about how it feels to have sheer nylons on my legs. This knowledge is forbidden to boys and men.
From there, my thirst for knowledge only expanded. I knew full well that it was perverse, and at that young age, at the beginning of puberty, sexual matters are secret; so I did this entirely out of sight. Nobody would ever know. I felt guilty about it, too. But I always wanted more. Then I fantasized about wearing other forbidden things. There was far more forbidden knowledge to be learned, and I needed to gain some experience in order to fully appreciate it. I developed an elaborate fantasy about how I'd have to wear pantyhose hundreds of times before I would be permitted to wear leotards, and those thousands of times before I could wear a bathing suit, and so on. This was partly a way to rationalize that I did not have access to these things, and would have to leave it to some distant, unimaginable future.
Soon enough, I did try on a leotard. But before that even happened, I borrowed my mother's swimsuit. Now I was in trouble. There was no turning back, and I knew it. I was deeply ashamed, but that didn't stop my intense cravings. I would look at pictures of sexy girls, and imagine wearing their bikinis. Now I was actually stealing things from people, and keeping it hidden in my room. Just about every day, I would masturbate in something girlie. Meanwhile, I was slowly becoming a man.
By now, my desire for lingerie was overpowering, yet it remained always out of my reach. Eventually, I did steal some panties, and wore them often. I was gaining lots of knowledge and experience. I could put on a bikini in the dark under my bedsheets. But it was seldom good enough.
I was so confused. Sometimes, I would wonder if I were actually a girl, and whether my parents and doctors had made some terrible mistake and made me a boy. But I knew this wasn't so. At the same time, I was shyly obsessed with images of girls in lingerie and swimwear. I fantasized all the time that they would force me to become like them.
By early adulthood, I had been with girls, and secretly worn their underwear. I started buying myself things, like lingerie and swimwear. I had accumulated quite a collection. I had learned more and more, to the point where I had become a sort of expert in feminine undergarments. I fantasized about ordering lingerie online. I made laundry lists for myself.
One girlfriend actually bought herself some lingerie and left it in my room, since she was afraid of what her mother would think. I wore it at least 10 times more than she did. When she and her family went away on vacation, and I was given the responsibility to water their plants, I took the opportunity to try on just about everything she owned. No man should know so much about women's clothes. Especially not what it feels like to wear them.
Relationships with women lasted long, but not forever. I would start feeling guilty about wearing their underthings while their backs were turned. I found myself focusing on my fantasies instead of finding new girlfriends. Wearing lingerie and swimwear was so satisfying that I hardly needed any fulfillment from any woman. I moved into my own place, and played with my outfits in secret, alone, just about every night.
I developed fantasies of becoming a girl. I wrote all sorts of them down. I read other people's fantasies, too. I learned a lot about men who want to become women. I bought a bustier, and a patent leather halter mini-dress. I owned about 5 swimsuits.
I moved away to a different city, and began to spend lots of my extra cash on women's clothes. I became obsessed with shoes. I had decided that I knew enough about wearing girls' clothes that I could wear only them when I was home alone. I would sleep in nightgowns. I would wear skirts and corsets and stockings and pumps while cooking dinner, watching TV, or vacuuming. My little French Maid's outfit was particularly fun for doing chores. This is when I felt ultra-feminine. I still wanted more.
I started wearing only women's underwear, all the time. I wore them to work under my boy clothes. In winter, I would wear a bra, which nobody could see because of my thick outer layers. I threw away all my boy underwear in a moment of passion.
Soon I started keeping my legs shaven. Then my chest. It made the girl clothes feel so much sexier.
Then I found out about a certain questionable drinking establishment where men were encouraged to dress like women. They provided change rooms and lockers, so you could travel there as a man, and conceal your true colours from the outside world. Now I saw how much more I had to learn. Some of my fellow patrons were gorgeous. I was terribly manly looking. I had some competition.
As I improved my womanly looks, I learned to spurn the advances of men. For God's sake, I'm not gay! Sure, I fantasized often and guiltily about furthering my forbidden knowledge, but apparently I wasn't ready yet. I longed for the taste of cock, which only women know. Everything I learned about women made me want to know more. But after years of happily pushing the limits, I had finally found a new and significant barrier.
People knew now that I was a transvestite. I stopped caring. I would wear androgynous clothes to work. Sometimes I'd have a bit of makeup on. It was difficult for a while, but I got used to it. I hardly needed my male wardrobe anymore.
Determined to learn my lesson, I practiced with some dildoes. I had misgivings about putting them in my ass at first, because most women don't do that, but I figured I'd hardly be feminine if I couldn't have a penis inside me.
Around this time, as I whimsically looked into how I could get a sex change, I discovered that some doctors make a distinction among transsexuals: those who genuinely are women trapped in men's bodies, and men who love to make themselves feminine. The distinction is remarkably clear. The former have always been outwardly feminine, and have no trouble pretending to be girls. The latter are actually very masculine, typically engineers, policemen, soldiers, or other masculine professions, and struggle to come off as women. Furthermore, the former want to be women so they can have sex with straight men. They are thoroughly homosexual. The latter are interested in women only, although they fantasize about sex with men, there is never any emotional connection. These doctors further posit that the latter should never be allowed to have sex changes, because they really are men through and through.
Recognizing myself as being firmly in the latter camp, I began to doubt my fetishes for stockings and panties and corsets and swimsuits and fellatio. But I couldn't prevent them. I envied those who were allowed to become girls.
Unable to resist, I finally sucked my first cock at my favourite bar. It was a terrible fiasco, as these first attempts always were. After almost vomiting at the end of it, semen all over my face and skirt, I vowed never to do it again, and stayed away for weeks. But in retrospect, I became aroused at the thought that I had sucked dick, like a girl. I had gained another piece of forbidden knowledge. It comforted me to think that this practically made me a girl now.
They say that practice makes perfect, and I began to meet with a certain man to improve my technique. I think I became quite skilled. It was almost too easy to have him teach me how to take a cock in the ass. By now I wanted to be as gay as possible, because it made me feel so feminine. When he pounded my ass and came inside it, I could only think of how feminine I was.
Now I became serious. I had sexy piercings on my belly button, my nipple, and my tongue. I was ready to learn the final forbidden lesson: what it feels like to have a penis in my own vagina. The thought excited me to no end. I was nervous when I made the first appointment. Lucky for me, the doctor didn't believe in this hogwash about autogynophiles. I would begin to live as a girl full-time, without exceptions, and take hormones after a year. A year after that, I would have the surgery and have a small piece of my small intestine cut out and my sensitive parts attached to it, to make it look and feel like a pussy.
It was hard to come out to my family, but eventually, they accepted it. Work was sensitive, but at least they were prepared for it. It felt good to be dressed like a girl all the time. I had a few sexual adventures, too. I was overjoyed to start taking the hormones, until taking so many pills became a drag. I had waited so long to fill in my brassieres, and finally, it was happening.
My mind began to change. I was much more emotional. I thought about stopping, but I persevered. After all these years of gaining feminine knowledge forbidden to men, I was finally really beginning to feel like a girl.
I still knew, though, that I was an autogynophile. Deep down I knew that I am fundamentally attracted to women, not men. Yet the thought of my own vagina was far too tempting. I needed this last bit of forbidden knowledge.
At last, the surgery was done, and I became a woman. It was months of visits and bandages and stitches and ointments before I could use my new body. In spite of decades of preparation and longing, nothing could adequately prepare me for the reality of it. I was aroused by the knowledge that I now had a pussy, but at first I couldn't even touch it. My arousal felt so strangely displaced. It hurt at first, terribly, because of the surgery around such sensitive parts. But eventually, it healed, and I learned to find my clitoris. It felt like somone had exposed the head of my penis to a nuclear blast. Later, I discovered that deep inside my new vagina are the nerves that were once on the shaft of my penis. It took days of desperate experimentation, but I eventually discovered a truly feminine orgasm.
This drastic reconfiguration of my cock, which had foolishly led itself to its own demise, was incredibly disturbing. I cursed myself for mutilating my most precious body part. I wanted to fuck girls with my dick again. I realized that I could never do it again. I cried a lot those days.
Armed with my new girlhood, and desperate to truly experience it, I trolled my old haunts for some action. But none of my old boyfriends were interested anymore. They were gay men, and fucking girls -- even formerly male ones -- did not at all appeal to them. It took many depressing months of trying before I finally got one. He was ugly and disgusting, but I needed to feel a penis inside me. I hardly even took notice of him as he fucked me. All I could think of was how incredibly sexy and feminine I felt and looked. Now it was simply a matter of trying different positions. Somehow, it was still never enough. It dawned on me that I must be a lesbian.
At last I knew the price of my forbidden knowledge. In the end, I am a man, no matter what my crotch looks like. I am insatiably attracted to women. I betrayed my gender, my identity, for a sympathetic fantasy about the object of my desire. I was punished the moment I learned my first lesson when I was a young boy. I was cursed with an insatiable desire to know everything that was forbidden to me from the beginning. I should have been humiliated enough to stop long ago, at many different stages. But instead I took it to this irreversible end.
And just the very thought of it makes me unfathomably horny.