Saturday, August 15, 1998

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.

Diary: Breakup

A__ and I are no more.  She never wanted the panties part of the lingerie I gave her, so it's still in my dresser, along with the stockings.  I have moved my other stuff into the same drawer now.  What the Hell's the difference?  It's all my underwear, isn't it?  I like the idea of having girls' clothes in my underwear drawer.
I have to fantasize about this again.  For weeks, the most intensely gratifyingly sexy deed I could think of involved fucking her, no kinks involved.  But I have to forget that if I want to move on.  So back to lingerie for me!

I've re-read much of this file.  There's a lot in there to turn me on.  I want to fantasize about it again, and get totally girlified once more.  I want to explore the possibilities of my fantasies again, in a systematic way.

Saturday, August 01, 1998

Fiction: Put Yourself In Her Place

"You know, honey," she said petulantly, "I'm sick of you treating me like a sex object. All you ever want me to wear is lingerie. How come you don't have to wear anything like this to turn me on??"

"Because you're a woman."


"Women look great in lingerie."

"Would you wear lingerie if it made you look good? Cause God knows you don't as you are. . ."

"Lingerie's for women. Why would I want to wear women's underwear?"

"What if I thought you looked good in it?"

"I wouldn't feel comfortable in it."

"You think I feel comfortable like this?"

"Why shouldn't you? You look incredible!"

"I feel like a slut. This stuff isn't made for comfort, you know. It's just too revealing. I feel silly."

"Oh, don't feel that way! Won't you wear it just for me?"

"It's just not fair, that's all. I'd like to see how you'd feel if I just sat there in my gitch and watched you parade around in tight silky frilly panties and a garter belt and a bra. . ."

"That's a bit different I think."

"How so?"

"Well, those things are made for women."

"I disagree. They're made for men who want to make women feel silly."

"Gimme a break."

"No, I insist. You wear the lingerie this time. I'm sick of it."

"You must be joking."

"No. I'm dead serious." She took off her bra, and tossed it onto his lap. Then she began unhooking her stockings.

"What, you actually expect me to wear this?"

"Why not? I had to wear it for you!"

"Yeah, but. . ."

"But what?"

"It's a bra."

"No shit."

"Bras are for women."

"No woman would ever actually want to wear a bra. Do you realize how constricting and uncomfortable those things are? Bras are for men. Men like looking at bras. Well, now it's my turn. I want to see you wear it. And I want to see you wear these ridiculous little panties and these stockings and this garter belt, too."

"I can't do that."

"Why not? I thought you liked my lingerie."

"I love it- on you."

"Well, you picked it out, not me. If I have to wear what you want, then you should have to wear what I want you to. And I want you to wear this lingerie outfit."

"All right. Fine." His face was almost purple. It wasn't rage. He looked nervous. I think he was sweating.

"What, are you afraid?"


"Are you scared of what people will think? Nobody has to know. Just me."

"All right, I said. I'll put it on."

And he did.

"Well, then. You look gorgeous!"

"Oh, shut up."

"How do you like it? Do you feel sexy? Or is it uncomfortable?"

"Shut up."

"You have an awfully big boner."

He almost burst with embarrassment. He was speechless.

"Don't try to hide it. I think you look adorable in a bra. If only you shaved your legs, you'd look beautiful."

"I don't see what you'd complain about, you know."

"I'm not complaining."

"I mean when you wear the lingerie."

"Why? Do you like it?"

"It's pretty comfortable."

She snorted. "You like it!"

"It's really not so bad."

"I'm really happy for you."

"It's all smooth and form-fitting."

"I can't believe this. Are you serious?"

"Yes. It's comfy. I like it."

"You actually enjoy wearing my lingerie."

"I suppose."

"You're such a bullshitter. Take it off. You're making fun of me."

"No, I'm serious."

"Enough, already. You've made your point."

"What point?"

"That I shouldn't complain about wearing lingerie."

"I just can't understand why you'd feel uncomfortable. I even feel a little sexy."

"Just take it off and let's get on with it."

"Could it wait a bit?"


"I don't want to take this off. It feels really nice."

"Please stop fucking around. It's not funny anymore."

"No, I'm serious. I'm seriously horny. This is amazing!"

"Alright. Whatever."

"Hey, you wanted me to wear it. But you were right. Lingerie is for men. I always thought women looked so good in their underwear. There's something. . . intimate about women's underwear. It's incredibly sexy. And I feel sexy wearing it."

"You're starting to scare me."

"Can I try on some of your other stuff? Like your bathing suits? Your bikini? A mini-skirt?"

Diary: Missing A__'s Wardrobe

I miss living with A__, and having the opportunity to dress up whenever she slept at her mother's. I desperately want to dress up right now. I want to put on some sweet little white undies and a bra, slip into some stockings, and wear a tight little black minidress on top. And I'd wear cute sexy sandals on my feet, too.

Fiction: Queen of the Brothels, Redux

Now, let's get back to our detective story:

So the kid got conned into wearing women's clothes.  I'm not sure how it happened.  It doesn't even matter I suppose.  They could have forced him.  They could have coerced him.  They could have convinced him.  He could have resisted them.  He could have reluctantly agreed.  He could have been in no position to resist.  He could have even suggested it himself.  But I think they probably took away his clothes when he took up with them, and told him to wear women's clothes or else they turf him.  They limited his choices to either running away naked, unprotected from his creditors, or staying there and dressing like a girl.  He probably values his life, and he chose the latter.  

From there, they slowly trained him to get used to it.  He couldn't run away then, especially then.  He looked ridiculous dressed that way.  Who would help him?  Then they started demanding his money.  They promised him that he could live with them forever, and not have to ever worry about food or money again.  He only had to do as he was told.  Evidently, he did it voluntarily.  Wrote them a big fat cheque with all the money his parents gave him.

From there, it was slow effeminization.  They taught him how to act effeminately.  He learned.  They gave him hormones.  He eagerly measured his bust every morning, waiting for his breasts to grow.  And they had him acting in their pornos, as a she-male.  A chick with a dick.  I've seen him in one or two of them, sucking dicks.  He's not quite girlish, but his tits are pretty damned real.

OK, that's going nowhere.  I can't forget in one of the dragscape stories, how the submissive husband was forced by his wife to become a girl.  He had a fetish for sweaters (of all things), and she had him dress up in one.  Then she had him put on her panties and bra, put a sweater on top, and go shopping for lingerie.  From then on, he wore nothing but women's clothes.  He became a girl for her then.  But she had a master plan.  She wanted to show him off later in public as a girl, with real tits.  She asked him to sign up for hormone replacement.  He was reluctant to go in for such a permanent change, but he did.  And he became a she-male, sucking his wife's boyfriends' dicks.  Voluntarily.  Now that's interesting.

Diary: New Silver Bikini!

Impulsively, I bought another bikini today. I think I struck gold.

I had actually been thinking of it for some time. I looked up a wholesale swimwear shop, hoping to find a good deal. The place was pretty small, near [a bakery we used to frequent], and pretty empty. I pretended to be interested in some flippers, but instead I took the silver bikini. It's a size 9-10, but the cut is very sexy. It's silver and shimmery, with a black plastic trim on the bra. I paid exactly $46 for it. I've been wearing the panties since I got home.

It fits quite nicely. I needed it badly. It's much better than that last one I had, although I wish I hadn't lost it. I wish I had been more careful about all of that stuff. There were some really good things in that bag, but it's gone now. Easy come, easy go. I'll especially miss that satin teddy with my first garter belt and my white fishnet stockings.

I've always been turned on by the idea of wearing women's underwear under my clothes. It's symbolic of how I feel girlish inside. Just as there's girl's undies under my clothes, there's a girl under my skin.

My only regret is having looked at myself. I look just awful in it.

I feel pretty good though.