Fiction: Affirmation

OK, that didn't work.  Took all the fun right out of it.

For the millionth time, let's get wrapped up in a fantasy:

What's more exciting?  A fantasy about a first-timer, or the uncovering of a regular?  Or the obliteration of shame by affirming femininity?  Really, it all comes down to the affirmation, doesn't it?  No matter what the story, the fun only really starts when the man discovers that he likes being a woman better.  It doesn't even matter how it happens.

It started innocently enough (as it always does in these stories).  It was just a lark, a joke, when I dressed up like a girl the first time.  It was sorta funny, you know.  It was, I suppose a mistake.  I had been wearing bikini underwear for years before I actually noticed the label.  I thought it was sexy and masculine, in the way that it was tight and skimpy.  But the label clearly says, "Women's" on it.  I don't know how I missed it.  I don't know how I could have bought it without knowing what it was.  But there it was, clear as day.  All this time I had been wearing women's underwear.

You can understand how crestfallen I was.  

I had never even imagined wearing women's clothes before.  The thought never crossed my mind.  If it did, I immediately dismissed it as frivolous.  Imagine: a ladies' man like me wearing ladies' underwear.  Absurd!  Yet there I was, for years, doing just that.

What difference does it make, I thought to myself.  It's the intentions that count, isn't it?  I thought they were men's.  I had no intention of wearing women's underwear.  They don't look feminine at all, but I'll admit that they were certainly tight enough to look awfully good on a girl.  So what's the big deal?  Nobody knows but me, anyway.

That's what I thought on the surface.  Underneath, subconsciously, it was a different story.  A little seed had planted itself in my mind, and I didn't even know it.  I suppose it's a mental association thing: the first little thought brought on a whole chain- no, a tree- of others, all derived from that little seed.  Me, wearing women's underwear.  Imagine me wearing sexy lace panties, a bra, and even a garter belt.  I banished those thoughts as soon as they entered my mind.  I was worried.  I vowed to never wear those briefs again.
Of course, it didn't work out that way.  I had to admit that I couldn't stay away from them.  They were comfortable, damnit.  And they made me horny.  They made me think of women wearing lingerie.  How could I resist that thought?  A pure, wholesome, heterosexual male thought.  Except it was different, somehow.  I was fixated on the lingerie.  Now THAT's women's underwear, I thought, as I salivated thinking about it, not this unisex crap I'm wearing.  

I used to drive myself to climax in that underwear.  I'd fantasize about girls and their sexy underthings.  Somehow, the thought that I was wearing girlie underthings too made me hornier.  I felt so subversive.  I knew what I was doing, I thought at the time.  When I was done, I'd feel just awful, like I would have to change out of them.  I felt ashamed, and I didn't understand why.

It became pretty clear soon enough.  I would think about those panties, and think of them in those terms, and get horny.  I got a strange kick out of reading the label before putting them on.  Nobody knows the difference, I thought, except me.  And it struck me: I'm wearing women's underwear, on purpose, and it makes me horny.  

The realization floored me.  This could only damage my masculinity, I thought, and became even more aroused.  This is so wrong, I thought, but it feels so good.  Before I knew it, I was masturbating, imagining myself becoming more and more feminine every time I wore these panties.  While I stroked myself, I didn't care what it did to my manhood.  Girlhood felt so incredibly good that I wanted more and more of it.  I felt so sexy.  Then I came, and came right back to earth.  I was so ashamed, and I threw the panties back into my dresser in self-disgust.

I worried about what was happening to me.  I tried to resist, but I couldn't.  When I got horny, it was because I was thinking of wearing something feminine again.  I didn't limit my imagination to my own panties, though.  I fantasized about wearing silky and lacy lingerie, two-piece bikini bathing suits and tight sexy women's swimsuits.  I was possessed.  Soon I couldn't stop myself from trying.  I had to have more than my panties.  They weren't even real women's underwear.  I decided to get my hands on a one-piece swimsuit, because it wasn't so extreme as a lingerie outfit or a bikini.  I couldn't just dive into something like that.  I wanted to, but I was afraid.  I didn't want to lose control.

I already had, of course.  Still, I took it slowly.  Painfully slowly.  I stole the swimsuit from my sister one day when I visited.  She never suspected.  I snuck into her room and rifled her dresser, stuffing it down my pants when I found it.  When I got home, I couldn't wait to put it on.  But I didn't trust it.  I kept my own manly underwear on to protect me.  I feared that the naked suit on me would be too much of a shock.

Even with my underwear to protect me, it was a phenomenal experience.  It was so snug on my body, and so smooth.  I loved fondling girls in their bathing suits.  I loved how tightly they caressed female bodies.  And now, here I was, wearing one myself.  I didn't dare finish myself at first.  It was just too much.  So I took it off, and hid it in my dresser.  The thought of it tortured me for minutes, until I decided to pull it out again, and finish what I had started.  Only I desperately wanted to feel it against my naked crotch.  I moaned in amazement when I finally had it on.  I couldn't believe what I was doing.  I felt so feminine, and I felt so incredibly good.  Until after I came, that is.

Amazing, isn't it, the way desires can so cloud the mind?  I was so disgusted with myself.  I slinked out of my sister's bathing suit, and wondered how I could ever get it back into her dresser.  There were stains all over it now.  I couldn't dare wash it: it would look awfully conspicuous in then laundromat.  I felt stupid and lecherous and perverted.  This fantasy was wearing away my masculinity.

These misgivings only lasted a short while until I got horny again.  I never did give that swimsuit back.  I wore it as often as I wanted to.  Which was pretty well daily.  I frolicked girlishly in it, imagining that I was trapped in its tight, elastic femininity, and that I couldn't get out of it.  The intense pleasure that I experienced from it was simply the magical process of my body becoming effeminate.  Yes, I wanted desperately to escape from it, because I didn't want to become a girl; yet it felt so wonderful that I wanted even more desperately to wear it forever, or better yet, take it off and wear something even sexier, like a matching lace bra panty and garter belt set, or a bikini swimsuit.  I simultaneously hoped and feared that I would become a girl if I continued.

I became so disgusted with myself that I threw the swimsuit in the garbage, vowing to never wear women's clothes again.  But it didn't work.  My cravings became much worse, because I had no more outlet for them.  So I stole panties from my sister.  Only this time, rather than just stuff them into my pants, I went to the bathroom to put them on under my own underwear.  That way, I would get to try them on at the same time as I concealed them more effectively.

The panties were white and frilly.  They were gorgeous.  The trouble was that I missed a bra.  I needed one to feel the full femininity.  I eventually stole that, too.  I pleasured myself relentlessly in my sister's underwear.  I began to fantasize about buying myself some lingerie.

It had gotten too easy to steal from my sister.  I knew that she had a bikini, so I planned to steal that, too.  I longed for one day and night, because I had never worn one before.  She caught me red-handed, rummaging through her dresser.  I must have been white as a ghost.  She knew exactly what I was doing, knew exactly where her other clothes had vanished.  

"So, you like my underwear, do you?"

I had to deny it.  "What are you talking about?"

"I've caught you red-handed.  Admit it: you want to wear my underwear, you sissy faggot pantywaist!"

She made me take off all my clothes in front of her, and put on her bikini.  Somehow, she read my mind.  I felt ridiculous.

So she took me to the store, and made me buy lingerie for myself, as well as all sorts of women's clothes.  She turned me into a girl.