Diary: Bikini Plan; and Bonus Fantasy: Basic Training

I think I have perhaps reached another stage in my development.  Well, not quite yet.  Almost.  I'm on the verge.  Sort of.  I don't know.

I've done it before, though.  It seems like a long time ago, though.  It seems like an eternity ago.  Maybe I've regressed a bit since then.  I just feel like I'm on the threshold of something huge again.

I'm going to buy my bikini within the next week.

Or so I say now.  I've been saying it for years already, but I've never dared to buy a bikini.  That would be crazy.  I've bought lingerie, but, it seems to me, that that's easier to find an alibi for, easier to explain away.  "I'm buying it for my girlfriend for Christmas," I explained.  One of many, I'm sure.  Nothing unusual about it.  But I bought it at a dead hour of night, when there were no other customers, probably in a place tacky enough that not many women actually shop there.  But I did buy it, didn't I?

I didn't have a girlfriend at the time, and that sort of precipitated my decision.  It also gave me the crazy idea to shave my legs.  I can't do that now.  But I plan to buy my bikini tomorrow or early next week.  I need it, I think.  I've needed it for a long time, and I'm not going to get one any other way.  Just like the lingerie.


I love talking about this.  It makes me feel so. . .I dunno. . . honest?  Kinky?  Horny?  Can I really reduce this whole enormous waste of disk space to a mindless stimulation of my fetish?  I suppose I can.  But no, I know that there is a larger psychological significance to this.  I know that writing about wearing women's clothing allowed me to feel more comfortable about it.  That moment when I first dared to admit to myself and my computer that I am a total flaming panty-wearing transvestite fetishist was one of the crucial stages of accepting myself.  Now I spend far too much time writing about it.  Revelling in my secret femininity.


I am wearing my green one-piece swimsuit right now, beneath my clothes.  Why not?  I want to buy swimwear, so I might as well wear what I have, right?  It gives me a taste of what I will have by the end of next week.  

There's not all that much more that I need.  I need the bikini, and I need some better panties and a bra.  That's about it, though.  I don't think I can buy the panties anytime soon, though.

I'm beginning to think of what to do with my stash.  I would just love to have an alternate panty drawer, where I keep nothing but dainty female underthings.  That would be ultimate acceptance.  So I figure that I might as well keep my stuff in my closet drawer, hidden in a bag, still, but in a drawer nonetheless.  The box where I keep it now is far too clumsy and inconvenient.  Besides, I have to think about where I will put my stash of girls' clothes when I move in with A__ [my girlfriend].  I can't get rid of it.  The biggest mistake of my life was getting rid of that wonderful blue and green bikini that I had stolen.  It was the greatest source of feminine pleasure that I ever owned, and I threw it away with the garbage, out of shame.  How stupid of me.  No, I must keep my girlie stuff, even though I might never have another opportunity to wear it.  I must take the chance.

I want to talk about my plan.  I have to figure it out before I actually do it.  Today, I walked to the [shopping mall] from work, half planning to scope out one of the department stores for the object of my fetish.  I didn't have the guts, and I didn't feel that I had the time.  So I didn't do it.  But I have to do it tomorrow.  I'm going to look around nonchalantly, not looking too closely.  I will closely monitor the crowd around me, to make sure that there are not too many people.  And I will make sure that there is a cashier nearby, so that I don't have to make too much of a spectacle.  Then I will buy it, just like that.  The cashier might ask me something, or look at me funny.  But I will play it down.  I'll tell her that my girlfriend wanted me to buy it for her for her birthday which is this weekend, and that the whole idea makes me uncomfortable, but hey, I'm doing it.  I just have to make sure that nobody sees me, and that I don't take too long doing it, and that it doesn't cost me too much money.  I don't really care what the cashier thinks.  As long as that person doesn't know anyone that I know.  The thing is that I will have gotten back my jacket from [the suit store] before this, and my framed print as well.  I'll have plenty of stuff to hide it with when I take it off the rack and bring it to the cashier.  Few people will notice, I hope.  Then it will be done, and I will have my own bikini.  I'll have to hide the bag (or only its contents) somewhere on me before I get back to work.  I don't want anyone to even guess that I've bought anything.  They might ask me about my jacket or about my print, and I'll gladly show them that, but I don't want them to know about my bikini.  That's my secret.  I will go the washroom in the mall and stuff it in my pants.  Or I will go to the washroom and hide in in my coat pockets.  Unfortunately, that is where my plan tends to fall apart.  I think the best option is to stuff it in my pants while I hide in a cubicle and pretend to shit.  Just thinking about it makes me nervous and trembly.  But it has to be done.  It'll be easy.  If I can't do it tomorrow, or during one of my future lunch breaks, then I'll have to do it in the evening.  There might be too many people about during my lunch break.  There are notoriously few shoppers in the late evening.  Nobody will notice me.  Plus, I can bring it back to the car, most likely in a box, and hide it on myself there, and discard the box.  Like when I bought my lingerie.  Simple.  It was too late tonight when I thought about doing it during the evening.

So that's the plan.  But what about the bikini itself?  And what about possible problems?

First, what do I do if someone sees me?  Ignore them?  Feed them the cockamammie story about buying it for A__ [my girlfriend]?  The latter would probably be best.  I don't think that there are great chances of meeting anyone from work.  Anyone else would be an enormous fluke.  If I meet a friend, then I will have no explanation.  Especially if I meet one of A__'s friends.  Still, I have my story, and I will stick by it.  I just won't be seen, that's all.  And even if I am, then I don't really care.  To Hell with it.  I need a bikini, and that's final.  Second, what if I can't find the right bikini?  Then I keep looking until I do find one.  If it's expensive, then I'll have to decide quickly whether or not to shell out for it.  I figure not much more than $60.  I'll probably think of more problems later.

The bikini.  What should it look like?

I know what I want to wear.  There are two different types that I would be willing to go for.  One is the type that I've already owned, similar to the blue and green one.  The bra I don't really care about.  It can look like anything, as long as it's not too big, or unflattering.  The panties are the important part, although I do need them both.  The panties should be either that inch-wide solid piece, dipping down towards the crotch, and small, or a thin string with little knots on the side.  Either one will do.  The material must be smooth like lycra.  If it's the first kind, the normal panty, then I want a bright colour, I think.  I want something exciting and bright.  Tropical, even.  I'd prefer a multicolour to a solid colour.  But I'll settle for a solid couloured one if that's my best bet.  It's the shape and price more than anything else that counts.

So when I go through with it, will it be another stage?  In a way, it must be: even though I've done it before, it must count.  Maybe it means that now I will do it with increasing frequency.  Maybe it means that I don't care how many people see me, and I don't care that I will most likely return to the store where I buy it.  Most of all it means that I am buying women's clothes even though I have a close relationship with a woman; my fetish still rules me.  

I can't help but remember my fantasies of effemination.  One little taste, I feared, would eventually turn me into a bona fide girl.  I would try on something innocent like pantyhose and forget about it for a while, then think about it, and try it on again, and again, then start thinking about other things, and start wearing that, too, and so on.  It's so much like my gradations fantasy: pantyhose 10 times, leotards 100 times, bathing suits 1000 times, bikinis 10000 times, underwear 100000 times, lingerie 1000000 times, and finally womanhood.  I also imagined skipping levels before my proper time, and that it's so dangerous that I can't possibly survive if I do it that way.  Like this:

I got started with pantyhose.  The leaders introduced it to me and told me that I would have to wear it ten times before I could go on to anything more.  We had to train, to prepare against effeminization by the enemy.  There had been reports that the enemy captured our men and brainwashed them into renouncing masculinity by making them wear women's underwear and masturbate in it.  At first I was reluctant.  I didn't think that I wanted to be a girl.  But after a couple of times, I looked at my lucky collegues who had graduated to bathing suits, and even bikinis, and, dare I imagine, actual underwear, and I envied them.  I wanted to be one of them.  I wanted to have some silk on my body.  I wanted to look like a girl, and feel as sexy as those garments can make me.  I desperately wanted to experience women's underthings directly on my naked body.  I wanted to experience it just like real women do.  I toiled away in my pantihose, at first content to enjoy them for what they were.  And they were good.  Very good.  Very intense.  But I looked forward to being allowed to wear a bikini.  It was still so discouragingly far off.  

I could just imagine how the lycra would feel against my genitals, soft and tight.  I could imagine how the elastic would snuggle high on my hips, and leave my thighs totally naked and exposed; I could imagine how the elastic would dip to almost my pubic hair in the front.  I could almost feel the tight, smooth lycra around my breast, under my arms.  And nothing masculine blocking its influence: just women's clothing directly on my male body, with nothing to protect me.  I sweated with anticipation.  

"What happens," I asked my trainer, "if I wear something before my time?  Like if I wear underwear after wearing a bathing suit only 500 times?"

She laughed.  "You'd go insane.  You couldn't possibly be ready for the shock.  You couldn't handle the sheer femininity of it.  You'd probably never be able to go back.  Your training will have been useless.  You'll renounce your masculinity for sure.  You have to do it as prescribed, or else risk being totally effeminated."
I understood the problem.  The idea of preparing us for the enemy's brainwashing would have the opposite effect.  I certainly wouldn't want that.  I removed my pantihose and dressed back up in my regular male clothes and went home.  But I couldn't stop thinking about bikinis and panties and bathing suits, and how sexy they are.  I worried that the desensitization program was failing me, but I comforted myself with the thought that I just had to stick with it, and I would be OK.

I graduated from pantihose and went on to leotards.  They were very tight, very form-fitting.  They were pink and purple, made of lycra, and very shocking at first.  I didn't enjoy them at all, because they made me feel uncomfortable.  I had to wear them 100 times.  I couldn't stand the thought that someone might notice that I feel so good in them.  I felt so vibrant and excited.  I almost wanted to swing my hips femininely.  They were high cut up the thighs, like a bathing suit, but there was a pair of stockings under it.  Plus, for every new item of clothing, we had to wear our own male underwear the first few times before the actual counting could begin, just to be sure that we wouldn't be shocked.  My own underwear at first, in my pantihose, seemed very useful.  I didn't want to know what it would feel like to touch it naked.  But then it began to feel intrusive in the leotards.  I wanted to know if the leotards felt as nice against my naked dick as the pantihose did.  It sure did.  It might even have felt better, with the tightness the bodysuit part exerted on my genitals.  I dreamed of wearing nothing but a bathing suit.  I could hardly even bring myself to think of what underwear would feel like.

Shocked at my thoughts, I asked my colleagues how they felt when they wore their ration of women's clothing.  None of them betrayed any hint of the enthusiasm that I felt.  I began to worry even more.  Why wasn't the desensitization working on me?  The very idea that I was actually being feminized, rather than frightening me or alarming me, gave me a startlingly huge boner.  It made me think about wearing higher level clothing in the near future, as I gradually move up the ranks.  I looked forward to it, not because I wanted to be desensitized, but because I had entertained the idea that I wouldn't be desensitized, and that I would actually enjoy it.  Enjoy it enormously.  I wanted to be wearing my leotard, so that I could fantasize.  But I felt guilty about the thought.  I wasn't supposed to do this.  I would be fine.  I would have to be desensitized.  Sticking with the program would help me.  I had to control myself.

It must have been the thirtieth time that I wore a leotard that I began to cheat.  Only halfway through the level were we allowed to wear our feminine attire to bed, because that would help desensitize us.  I smuggled my leotard out of the locker room and brought it to bed with me.  I wanted to sleep with my leotard.  I slipped into it in the dark, and I masturbated myself to sleep.  I was careful not to come on it, so that no one would notice when I exchanged it for a different one in the morning.  I felt disgusting and ashamed when I was finished.  I had cheated.  I was risking my masculinity, ironically to please my sexual desires.  I put them away and got my regular clothes back on.

The next night, I couldn't resist but to do it again.  And the night after that, too.  And every night thereafter.  Every night I felt guilty, but I became better at concealing my secret.  Nobody even suspected.  Despite my shame, I had to admit that I thoroughly enjoyed myself.

Around the sixtieth day of leotards, I asked my colleagues whether they looked forward to wearing the one piece bathing suits for 1000 days.  They all seemed either apathetic or unenthusiastic.  "What, do you think you guys would be ready if they made us wear them now?  I mean, if you guys are so desensitized to these leotards, then what difference does it make if you were to wear a bathing suit tomorrow?"

They chided me.  "Ha!  So you think you're better than us, huh?  You think you're ready for the bathing suits?  I'm not.  I don't want to risk my manhood.  Even though I don't see much danger in me wearing one, I don't want to take the risk."

"So," I retorted, "you're a pansy about it, are you?  What are you, afraid?"

"All right, then, smartass, let's see about you!  Are you willing to do it?  Are you willing to skip a few grades?  I dare you to, if you're such a man."

I must have almost blushed at the thought of what I had gotten myself into.  A challenge to skip ahead and wear a bathing suit.  "Ok, if that's what you think, I'll do it.  I'm not afraid.  I dare you to do it, too." 
He agreed, and we struck up a plan to steal some bathing suits that day, and to meet at night wearing them over our underwear.  

So we managed to get our bathing suits.  I brought mine with me covertly, and when I was alone, I slipped into it, putting it over my underwear, as we had agreed.  It was exquisite.  I wanted to feel the inside of it.  I felt so sexy, so feminine.  I must have stood there amazed, rubbing myself, for ten minutes.  
At the appointed time, I showed up at our meeting place.  He was already waiting for me.  

"So," I asked.  Let's see what you're wearing under that."

"You first." 

"Simultaneously."

"OK."

"At the count of three."

One.  Two.  

Three.  He was in his bathing suit, but he seemed hesitant.  I burst out of my clothes.  

"So there.  You dared.  I'm shocked."

"Well. . . I guess you're right.  I'm not afraid of this shit."  He almost spat as he said it.

"What's your problem?  Does it bother you to be breaking the rules?"

"Fuck you.  You sure seem to be enjoying yourself there, buddy."

"Yeah, so?  I'm just not afraid of this."

"I think you like wearing this stuff.  You'd better be careful.  Before you know it, you'll be out of control, and you'll want to wear it all the time."

"Yeah, right.  I don't think so."

"Well, just consider yourself lucky that I don't rat on you.  And think about what I'm telling you.  It's dangerous.  I don't want to risk myself any longer."

"Suit yourself," I answered, and walked away.  I probably sachayed away, actually, now that I think about it.  When I got to my room, I didn't want to give up my prize.  I kept it on all night, but made sure to keep my own underwear on the whole time.  After all, I didn't want to enjoy it too much.  


Of course, that didn't last long.  I bragged to my colleagues that I wore the bathing suit.  It made them uneasy.  I figured that they were just impressed.  they wished that they could be as brave and manly as me.  I proudly snuck into the supply room and stole another bathing suit every now and then, letting the guys know that I was braving it more and more often.  Already the second time I dared to try it on without my underwear.  Totally unprotected.  I almost died of pleasure.  I started strutting it around when I thought I was safe.  I was way ahead of them in my development, even if my advancement wasn't being officially recognized.  But in the back of my mind, I was already planning my next coup d'etat: I would try on a bikini.

Just like before, I snuck into the supply room and took the sexiest, tightest, most colourful, skimpiest, most feminine bikini that I could find.  I spent a long time, heart palpitating, trying to choose.  I didn't even keep my underwear on when I put it on.  It was even better than I had anticipated.  I loved it.  I wanted to keep it on forever.

As my forays into the storeroom increased in frequency, I feared the danger to my manhood.  But I didn't care when I thought about the pleasures of wearing such incredibly sexy clothing.  Only when I finished myself did I chew my nails worrying that I had gone too far.  Even as I longed for my next level of advancement, I feared that I was becoming a girl.  Desensitization was failing miserably.  It turned me on somehow to think so.  But I realized that what was done was done.  I had started the process of effeminization myself, and I knew, as much as I feared admitting it, that I was slowly turning myself into a woman.  There was no stopping it.  I would resist it as much as possible, but I would fail.

That was when I decided to not cheat anymore.  I truly felt ashamed.  I would maintain the program.  No more enjoying myself.  But the program tempted me, too.  It offered me pleasure that I could not indulge in.  I tortured myself as I forbade myself from satisfying myself with what they supplied me.  Sometimes it was impossible, but moslty I succeeded.  For a while at least.

One of the crucial moments occurred when, masturbating in a bathing suit when I wasn't even allowed to wear it to bed, I was caught by my mistress.  She scolded me, and I never felt such shame.  She was truly shocked, and totally unable to understand.  I had cheated.  She didn't know what to think.  She exposed my secret to the leaders, who decided to shame me in front of all my colleagues.  I was bucked down to pantihose.  I had to work my way all the way back up.  I had to be desensitized again, from scratch.

Of course, I didn't mind at all.  In a way, I rejoiced because it meant more time for me wearing women's clothes.  But I wanted to wear more enticing stuff.  

So I did.  I wore underwear now.  I stole panties and bras.  I kept them, too.  I needed them.  I was much more successful at cheating now, because I had a recourse to better things at night when no one was looking.  having to sleep in leotards, I slipped into my panties and bra and worked myself over better than anyone had ever done.  I was safe, because I had struck up a friendship with my mistress.  She felt remorseful about denouncing me.  She wanted to understand, and we had long talks about my ambitions.  

"Why do you want to jump levels?  I don't understand.  Isn't the desensitization working?  Don't you want to be a man?  Don't you like being a man?"

"Of course I do.  I don't know why.  I just enjoy it, wearing your stuff."

"What do you mean, you enjoy it?"

"Well, it, uh, excites me.  It makes me feel so much more confident, so much more comfortable.  And I love the way it feels on my body.  I love the way it looks.  It's very pretty.  I could ask you why you like wearing your stuff."

"I'm supposed to!  I'm a woman!  You're not, and you're not supposed to wear it!"

"But you must admit that it's very pretty, and soft, and sexy."

"Yes."

"That's all it is.  It's just fun."

"Oh.  I just don't know what to do about it."

"You don't have to do anything about it."

When she realized that I was stealing her things once in a while, she became angry.  But she couldn't denounce me again.  So she came to an agreement with me.  She wouldn't denounce me, but I would have to stop wearing her things.  She would give me her hand me downs.  I thanked her with all my heart.

For a long time, I only wore it secretly.  I didn't want her to see me in her stuff.  I knew she didn't want to see it.  She already saw me desensitizing, and knew how pointless it was.  We once surprised each other as I was wearing her stuff, and she since became more comfortable.  Soon I would start wearing her old underwear in her presence without any problems.  We talked about lingerie fashions.  She showed me a few beauty tricks.  I was her girlfriend now.  The big step was in becoming comfortable with her while wearing her underwear.  
This went on for a long time.  I graduated to my own underwear after a while, and I didn't need hers.  I had my own panties and bras.  Soon I wore lingerie, and had the greatest time of my life.  Unbeknownst to the authorities.  I graduated with flying colours.

Then I was captured by the enemy.  I am proud to say that the desensitization program worked perfectly.  When they tied me down and forced me to wear their lingerie, I laughed and obliged them most happily.  They were amazed.  They threatened me not to play games, and I didn't care.  They stripped me down and shaved me naked, and forced me into a gorgeous lingerie outfit, which I thoroughly enjoyed.  I pranced around like one of the girls.  I became a girl at last.