It all started very innocently. I was 5 years old. We had a kindergarten class pantomime, in which all the children were to dress up as flowers. Everyone had to get white tights as part of the costume. All the boys got to wear girls' tights. I don't know how anybody else felt about it, but I liked it. In my primitive sexual mind, at that young age, I liked the way it felt on my penis. That's when I learned that it's bad for boys to wear girls' clothes. But the seed was planted.
Years later, I got up the nerve to borrow some pantyhose. I had never forgotten my experience with the white tights. I liked the idea of being dominated by a woman. Before the pantyhose, I would fantasize that a woman was making me kiss her boots. Somehow, I was heavily attracted to women. But it was all very bad. I knew somehow that it would be wonderfully naughty to be turned into a girl. So I played with pantyhose. At first I wore it over my underwear, for fear of it really making me a girl. Pretty soon I was all naked inside it, unprotected from its sheer femininity.
Shocking fantasies of being utterly feminized
The fantasies became elaborate scenarios of metamorphosis. And it had a lot to do with my own free will. I would imagine resisting for as long as possible, but in the end succumbing to the extreme pleasure. I imagined what it must be like to wear bathing suits, or even lingerie. Just the thought of it made me incredibly horny. I made excuses, believing that if I dared to go that far, there would be no turning back.
Experiments become more daring
I couldn't resist. I moved on to whatever I had available. I dared to put on a one-piece bathing suit. It was heaven! I knew I was in trouble, but while I wore it, I didn't care. I wanted to go all the way, by wearing even panties and brassieres. But I could only do it gradually, given that I had virtually nothing to work with at my immediate disposal.
I started to steal things from friends' sisters, from Mom. I needed it. Pretty soon I had a little collection that I thoroughly adored. And I wanted more. I fantasized about stealing underwear from clotheslines. I had even acquired a bikini!
I had gotten too bold. Mom found out. She was shocked and didn't know what to make of it. She quickly gathered her things that I had stolen, and I begged her not to let anyone know. I swore to never do it again.
I was so ashamed of myself, that I even got rid of the things she didn't find. I cursed myself for what I had done.
The inevitable relapse binge
I denied myself for so long that the urge to wear something female became uncontrollable. I stole a bathing suit again, and fell off the wagon. I binged more than ever with girls' clothes, and loved every second of it.
Denial and abandon
Then I would become ashamed and throw everything away again, vowing to never do it again. But each time, I could only go so long. Realizing that I was giving in only made me hornier, because it made me understand that every time I wear an article of girls' clothing, I become more and more addicted to it; which leads to the inevitable conclusion that at some point, I will become a girl from doing it so much. This only fed the pleasure I got from it more, because the whole point was to make myself feel like a girl. Then, as soon as I was done, my shame would lead me to renounce my habit yet again, and the cycle would start over.
The next time I was caught, I was in the middle of masturbating with a bikini. I was mortified. Before, I had only had my stash of girlie clothes discovered. By now I was in my mid teens, and I was seen by my parents wearing a bikini. I was so embarrassed that I couldn't speak. I covered myself up in my shame, and my parents tried to console me, rationalizing it to themselves more than anything. I swore, once again, to quit forever, but I knew that I had a problem.
My problem wasn't that I was wearing girls' bathing suits and underwear; it was that I wouldn't admit to myself that I loved doing so. This I discovered when having a little chat with my father. I didn't tell him so, but he could certainly tell that I was not going to quit. I would, however, keep it secret.
On my seventeenth birthday, I was shocked to discover lingerie under my pillow. I had never been able to steal anything so sexy. I knew that it didn't belong to my Mom. Somebody knew of my habit, and was now actively condoning it. I wore it under my boy clothes all day the next day to celebrate. Only later did I find the note that was meant to be attached to it. It read, “I just want to know, for sure, whether you have quit your dirty habit or not. I know it must be very hard for you. If you leave this under your pillow tomorrow, I'll know that you want to quit. If not, then please take these. I'd rather have you own your own than borrowing all the time.”
The realization of the enormity
Things started appearing in my dresser at random intervals. There were many pleasant surprises for me. Within a year, I had a small collection of just about everything a girl could want. I was wearing it almost every night. Only when a girl became interested in me did I realize the enormity of what I was doing. I couldn't possibly let her know about my collection, which sat openly in the top drawer of my dresser. I could never tell her that I not only have worn fishnet stockings, a garter belt, a brassiere, many bikinis, and all sorts of satin and lace panties and nightgowns; but I also own some! I thought of how my initial fears of becoming feminized were becoming totally true. And I masturbated at the thought.
Busted – for good
By the time I went away to college, I had been with a few girlfriends, and always kept my secret to myself. But I also secretly borrowed their things whenever the urge struck me. I was incorrigible. Annie outsmarted me, though. She suspected that something was awry. We were living together, and she noticed that some of her undergarments would shift. She set up a hidden camera, and caught me red-handed putting on her bathing suit. She confronted me with the video, and I was contrite, ashamed, and extremely fearful. She threatened to tell everyone. I begged her not to. She relented, but things would change dramatically between us from that point on.
She majored in psychology. She manipulated me like a handful of putty. She immediately became dominant, with the threat of exposing my habit to the world hanging over my head. She was curious more than anything else. She wanted to understand what got into me. She wanted to explore the phenomenon. She had me dress up for her. At first, it was extremely awkward. She was only the third person to ever see me wearing women's underwear. She asked me to go about my routine, and tell her what I was thinking. I couldn't do it for days, but eventually, I succeeded. I was wearing a bikini, and she decided to play along, rather than spectate. We frolicked together, both of us wearing sexy women's swimwear. I purred to her how I wanted to be just like her, how I wanted to be as sexy as her when I wore her bikini. I told her that I longed to be worthy of the clothes I play with.
She tried different tricks, but it became part of the routine. I would cavort around in lingerie for her every night, under threat of being exposed to the world. She soon discovered how uncomfortable I became about the whole situation when I wasn't horny. She had me tell her that I wanted to shave my legs while I was hot with desire, and she talked me into doing it, in spite of the fact that it would be terribly easy for anyone to notice. I was so horny that I enjoyed doing it, in spite of the consequences. After I came, she asked me if I would wear makeup, and she couldn't get me to agree to it without threats.
This led to a phenomenal escalation of my habits, which, as long as I was still aroused, I gladly agreed to. Before I knew it, I had beautiful long hair, easily stylable into a feminine look; I had become an expert at applying makeup; I kept most of my body hair shaven at all times; and I could walk in high heels. She only let me come just before I went to sleep. I said all sorts of incriminating things. I signed documents attesting to my desire to become a girl. I professed my dissatisfaction with my lack of womanhood to her video camera. I was giving her more and more material to incriminate me with, to the point where it became almost moot. I swore to her, on tape and on signed documents, that I gladly give up my own penis in a heartbeat, and even suck someone else's and swallow all the semen.
The weight of her threats lay in my desire to keep my femininity secret. Unfortunately for me, not only had the changes to my appearance become noticeable during the day, but I became indifferent to my reputation as a man. I was wearing women's underwear under my clothes, to keep me horny all day long. I felt so good that I wanted people to know what I was wearing. Many people suspected it. Eventually, there was no doubt: Annie coerced me into dressing up as skankily as possible with her, and going for a walk in public. I agreed readily, but became extremely nervous when we actually went outside. Everyone recognized me. In a way, I felt extremely sexy and proud; in other ways, I felt deeply embarrassed. But I got used to it. Within weeks I was clubbing in my girl clothes. Luckily, I could still fight. I was still manly enough for men to want to kill me.
With the threat of exposure nothing more than a quaint memory, Annie found other ways to manipulate me. She made me realize just how deep my desire to be female really went. I had always kept it to a subtext that I wouldn't even admit to myself, but she hypothesized correctly that I wanted to fuck boys. She would get me so hot and horny that I would be practically female; then she introduced me to some gay man she knew from college, and encouraged me to explore my urges. She made me feel so thankful to her that her threats had changed: now she threatened to take away my girlishness. I became her sissy slave. I would stay home and be her maid, and she would bring home boys for her own pleasure, and show me off to them as her creation. I was permitted to suck cock from time to time, and even to get a dick rammed up my ass. I was a time of great and exciting discovery for me. But she wouldn't allow me to enjoy it as much as I could have.
Soon she realized that her hold on me was entirely based on preventing me from having orgasms. She kept me tied in a penis constraining device so that I would behave better. I was extremely horny at all times, and I became an insatiable cock whore. She kept me in her power by promising more cock. But I was not allowed to come! I physically could not ejaculate. I so desperately wanted to.
I broke my bonds from her at last and came wildly for days. She was appalled, and threatened to deny me from getting any more cock. But I discovered that I was fully able to get some by myself. I was now passable enough to get it, or else brave enough to go to a gay bar and bag myself some easy action. I laughed when she threatened to expose me. My transformation was now complete! I hadn't worn any article of men's clothes in many months, even in public; and I bought my own lingerie and club wear. I was a little tramp! I moved out in a huff and got my own place.
A taste for cock
I ditched all my men's clothes that I was no longer wearing. I became a fixture at gay bars. My parents found out, and disapproved. I laughed in their faces, too.
My fate was sealed from the very first moment
So now I'm scheduled for my pre-operation hormones. I'm growing my own breasts, and giving up my worthless penis for a glorious pussy.