Diary: How I Became Such a Sissy, and How I Hope To Become Even More of One

It started innocently enough.  But I fear that the fears of men are well justified.  Somehow, masculinity knows what threatens it; it knows its enemy, but is powerless against it.

It's a very distant memory: the annual school pantomime, with every class performing its own number.  My entire kindergarten class, for reasons that I cannot recall, dressed up as flowers.  We all had to wear white stockings.  Or maybe we didn't dress up as flowers.  We did definitely have to wear the white stockings.  I have no recollection of what it was that we performed.  I was, after all, only five years old.  But that was the first time.  Or at least it was the first time that I remember.

Some fathers object to any suggestion that their young boys wear anything even remotely feminine, be it stockings or dresses or kilts or whatever.  They fear that somehow, their boy's mind might be warped, and he might grow up to be effeminate.  Perhaps the young boy might become used to wearing feminine clothes and might grow to prefer it.  Perhaps the boy might become homosexual.  It was like a subversive idea that would cause the downfall of civilization if anyone ever learned of it.

I learned that idea in kindergarten.  Those macho, over-protective fathers are quite close to the mark.  Perhaps they know something more than they should, too. . .

How long before I actually dared to venture into the dirty laundry for more, I cannot say.  But the idea must have lingered long in my head before I did it again.  And I knew that it was wrong.  I knew that I was seriously jeopardizing my masculinity by "borrowing" a pair of pantihose.  That first innocent experience, when I was forced to wear girls' stockings in front of hundreds of people when I was five years old corrupted me forever.  It was the first time, the first of countless thousands of times over the years, that I have worn women's clothing.  

I must have hardly noticed it at first.  But I remember asking my parents if I could sleep with those stockings on that night.  I wanted to masturbate in them.  But they denied me.  I fell asleep that night longing for what they put away in my dresser, where I was afraid to reach for it, for fear of being discovered.  I knew that they didn't want me to wear it.  And I fear now that they were somewhat alarmed about my request.

I must have longed for pantihose for years before I summoned up the courage to wear some again.  I have no idea how long I fantasized about it.  I do remember rolling up my underwear to make it more skimpy and feminine.  I probably worried about that, too.  But it couldn't have been that troublesome: after all, I wasn't actually wearing women's underwear, I was just fantasizing about it.  

Worse, I eventually did try on some pantihose.  I think I dug for some in the dirty laundry a few tense times, without daring to take any.  But eventually I did.  I certainly didn't want to become too effeminate: I protected myself against it by keeping on my own underwear.  But eventually, I succumbed to the temptation to go into it naked.  And I worried afterwards that I had taken my experiments too far.  I was afraid that one day, I might actually wear all sorts of effeminate things, like bathing suits and lingerie, because as I pleasured myself, I imagined myself wearing those effeminate underthings, and I hoped that I would one day wear only women's clothing.  

I imagined myself being forced to wear things by beautiful women, and I would discover the pleasures they afforded, and aspire to be female.  I would go through a hierarchy of femininity, wearing pantihose first, then leotards, then bathing suits, then bikinis, then lingerie.  I made this up because I had to come up with some excuse for not having lingerie at hand.  I would have jumped right into it if I had had the opportunity.  I imagined myself in the middle of a less interesting stage of my feminine development, and cheating by trying on something super-sexy that I was officially not ready for yet.  There would have been others like me around me, but they wouldn't be as enthusiastic about their clothing as me.  I was crazy for doing it that way, risking my sanity somehow, perhaps risking my sexuality.  

So, as the years went on, I tried on all sorts of things, always ashamed after I was done; but I couldn't make myself stop.  I always returned to it.  And that made it worse and worse: I thought that I could destroy my stolen pantihose and bathing suits and swear to never wear women's clothes again, and I would be cured.  I thought that I could restore that part of my masculinity that I had lost by fantasizing about becoming female by renouncing my secret practice.  But that only made me want it more.  I would go for weeks or months without women's clothing, and curse myself for having gotten rid of it.  I still fantasized about it, and it became unbearable.  I absolutely needed to wear something feminine.  Every time I quit and started again, it reinforced my femininity, and weakened my masculinity.  Every time I started again, it proved that I did become effeminate by wearing women's underwear; and being effeminate, I needed to wear some girls' clothing to feel comfortable.  I repressed myself so much in that time that it is not hard to imagine why I had such a difficult adolescence.  So every time I went back to it, I felt that much more like a girl happy in her comfy, sexy underwear.

Men are correct in thinking that doing something effeminate, in my case wearing women's clothes, makes one irrevocably effeminate.  That one little incident with the white stockings in kindergarten, even though I was far too young to have much of a sexual awareness, infected me with the tiniest little bit of girlishness.  That tiny little bit has blossomed into a massive, barely controllable desire to be a girl, and to dress like a girl.

Just imagine the scandal!  My precious masculinity, defiled by a scanty elasticated swatch of lace and silk!  Unprotected against the high-cut crotch-cuddling spandex of a bathing suit!  In direct contact with something which should only come into contact with femininity.  Just picture it: a macho man wearing little silky panties, a bra, a garter belt, and stockings, acting as much as he can like a girl in heat.  A horrible thought!  But think of it as yourself, and think of yourself as that sexy slinky supermodel who skips around in her lingerie.  It's not just the thought of wearing women's clothing, it's the thought of renouncing masculinity that arouses me.  The idea that I could wear women's clothing often enough to actually become a woman drives me into a fit of passion.

I have this picture in my mind of a sexy woman in lingerie dangling some panties in front of me teasingly, enticing me into wearing them.  I look at myself, and I'm wearing my own clothes.  But the legs sticking out of my shorts are shaven smooth and effeminately sexy.  I feel a pang of shame as I look at her, understand her suggestion, and understand that it means that I, a man, have willingly submitted to this process of feminization too many times to count, and that she expects me to do it again; it shames me that she knows that I, a man, wear women's underwear for sexual pleasure; but I get up, coyly, and follow her into the bedroom as she cajoles me by swinging her little panties under my nose; and it shames me that I remove all vestiges of masculinity from my body, and slip into the sexy lingerie she has selected for me to wear.  But ultimately, I succumb to the lingerie, forgetting my shame, and abandon myself to wild sexual pleasure, just by being, at least cosmetically, female.  Here's more of the fantasy told dramatically:



I sat at my comfy lay-z-boy, watching hockey on TV and drinking beer, when Amy appeared around the corner of the doorway, only her head visible.  Her blond hair was up, with a few stray locks dangling around her neck.  She purred as she called my name.

I looked right at her, and half expected what was coming.  She grinned and slowly raised her arm, revealing it from its concealment behind the wall.  She dangled some scanty little silky panties in her hand.  "It's time to play," she meowed.  She stepped out into the doorway wearing her favourite lingerie outfit: a white bra and panties with a matching garter belt and white stockings.  

I could feel my head turn livid with shame as I understood her suggestion.  I glanced away from her because I couldn't bear to look at her; but that was no better, as my glance fell to my own legs, silky smooth shaven, sticking out of my shorts.  I turned towards her again, and she had come into the room just enough to hold out the panties centimetres from my face.  I followed her as she backed away towards the bedroom, cajoling me all the way with the panties in my face.  I could smell the delicate perfume in them, they were so close.  

I felt self-conscious as I trailed shyly after her.  I felt like hiding under the couch.  I felt like I was walking up on stage at a massive theatre for the first time, wearing nothing at all, with everyone in the building gawking at me.  

We finally reached the bedroom.  "Here," she said playfully, handing me the panties.  "I thought you'd like to try these on for me."  I took them sheepishly in one hand as I pulled off my baggy shorts and underwear in one swipe with the other.  I looked at her rummaging in her dresser, her lovely playful tits snug inside her frilly bra, and her legs dainty and lithe in her stockings.  She was the sexiest, most beautiful woman I have ever seen.  

I inspected the panties more closely.  They were silky, with a lace trim, and white.  The crotch elastic looked so pretty and delicate, as did the skimpy waistband.  I slipped into them quickly, snapping the tight waistband as I reached the top.  I rubbed my silky legs together and whipped off my shirt.  I stared at my hairless body, wondering at how awkward and male it looked in my sexy little panties.  Amy handed me another white bra and a garter belt, which I snapped on happily but nervously.  I eagerly anticipated wearing stockings on my bare, shaven legs.  I rolled them on luxuriously as Amy watched, approving of my feminine mannerisms.

I preened in the mirror for a few moments, my hair down, my super-hard dick tucked painfully out of view, and admired how gorgeous these clothes made me.  Still, my butt looked too hard, and I had no tits, and my frame was too square and heavyset; but I looked pretty, well, pretty nonetheless.  Amy opened the closet, and handed me the high-heeled sandals we had bought just for me because I could never fit my gargantuan feet into hers.  I was now walking and talking like a girl, loving the feel of the stockings on my legs, and rubbing them effeminately together as I pranced around.  

Amy grabbed me suddenly by the waist and threw me onto the bed.  We snuggled up together, touching each other's feminine bodies, and talking about girlish things, like how pretty we looked in this or that, and how wonderful it would be to wear such and such a thing.  We were girlfriends.  We were so close in these moments.  She would tease me about how I am enjoying wearing her lingerie, and I would blush demurely.  Then we made out, and petted.  I wanted to never remove my clothes.

She knew what she was getting herself into when she dangled those panties in front of me.  I became wild with passion, feeling every bit the girl I wanted to be.  I wrapped my legs around her and rubbed myself all over her belly.  I screamed for a penis.  I desperately yearned for a dick inside me, and I pretended that she was a man mounting me and fucking me.  I totally lost control.  And she loved it, because I became so passionate.

When I came at last, all over our pretty undies, I nearly fainted.  I rolled Amy off of me, and remembered where I was, and who I was: a man, still a man, strapped in slinky feminine clothing, feeling utterly unable to extract myself.  Again, I turned livid with shame, so completely aware that I was wearing a bra, panties, and a garter belt, and how the fabric of each of these items clung to my sweaty body.  My body suddenly felt out of place in lingerie; I wanted desperately to get out of my feminine clothing, to run and hide from Amy.  But she prevented me from leaving.  She hugged me from behind, and would not let me leave.  She fell asleep like this, fingering my bra strap and my garters, drawing my attention even more to what I wore; and I myself fell asleep as I was, unwilling to disturb Amy by getting up and taking it all off.  That night I slept like a woman.