This is Becoming a Habit

 I'm on another business trip, and as is becoming usual, I bought myself some nail polish and makeup.

I bought a cheap makeup box on Amazon, which includes foundation, bronzer, blush, a bunch of eyeshadow, and lip gloss. It's a very small case, and it comes with little brushes. It's low quality stuff, but I want to practice putting on eyeshadow especially. I had it delivered to the hotel so I wouldn't have to pack it.

When I got here, I also had to get myself some nail polish. I get really excited about painting my nails, and I jump at the chance to do it when I'm travelling alone. I'm getting better at putting it on, but I still need a lot of practice. I still want to wear it in public someday, but I'm not ready for that now.

I also bought some eyeliner and mascara. I couldn't just do eyeshadow, right?

I read and watched tutorials on how to do it. I need a lot of practice. I must say though that it's really, objectively fun! Never mind that I'm a raging sissy, it's really enjoyable putting colors on my face. Brushing it on, blending it, and watching it come together is altogether pleasant. I look hideous, and I did a pretty bad job, but I thoroughly enjoyed it.

Now I've got my eyes and lips made up, and my nails painted, and I'm wearing panties and a nightie. I'm totally girlied out, and I love every bit of it! I really wish right now that I was a pretty woman, so I could do justice to what I'm wearing. For a while I lay back in bed and simply luxuriated in this femininity.

I'll be here for three more nights. I'll be removing the nail polish from my fingers every morning, and putting it on again at night. I plan to practice putting on the makeup every night as well, but whether I'll have the energy to remains to be seen. On Thursday, I'm expecting a delivery of two dresses, a bodysuit, and two bras. I had wanted it to arrive much sooner, but that's the way it goes sometimes.

Right now I'm especially excited that I'm becoming the type of person who knows how to put on makeup.

Escalation and Elevation

When I was young and I had my stash hidden under my bed so I could indulge in my fantasies at night, I had a fear of taking them too far. I was very careful to slip into something feminine in my bed, under my covers, bedroom door closed, certain that everyone else in the house was asleep. I was terrified of getting caught. I had convinced myself that one of the greatest and most thrilling dangers would be to fall asleep in whatever I had worn, and wake up in it. Sleeping in something feminine became a cute fantasy of its own: where I normally only wore girlie stuff for brief moments, this would be over a much longer span of time; and the damage to my manhood would surely be much more severe. If only I could dare!

I finally went through with it once a few years ago. I had finally reached a milestone: sleeping all night in women's clothes. Such opportunities are rare indeed, so I've never done it again.

After I got caught, my thinking around this no-longer-secret fantasy changed. It's so much fun to wear women's clothes, but the real thrill is in feeling feminine. I often found that I didn't need to wear anything feminine to scratch my itch. It certainly helps, but my guilt led me to do it much less. I started to get off much more on the fantasy of becoming female, and not only wearing women's clothes, but doing all the things women do to accentuate their beauty. I especially started to appreciate painted nails, particularly in cold colors like blue, and most of all sparkles of all kinds. I found myself getting very turned on by women's nails! I had never paid them much attention before. Of course, that means I want to wear nail polish now.

I was watching a "girl for a day" type of video, and a boy became outrageously pretty as a woman. What really put me over the edge was the manicure. It's great to have put on some lingerie and a revealing outfit, and done up your hair and makeup. But if you've done your nails, too, you've really gone all the way!

All this to set up my current adventure: I'm travelling for work, so I get some time to sleep alone for a few nights. When I re-built my stash, I bought myself a nightie specifically so I could fantasize about having something feminine to sleep in if ever the opportunity came up. I snuck it into my suitcase, along with panties and my black teddy, with the intention of sleeping en femme for the duration of the trip. I had initially packed my usual boy pajamas, but feeling bold, I took them back out. I have no choice: my only sleepware for this trip is feminine!

And the icing on the cake: I found a drugstore near my hotel, so I got myself some nail polish. I already put it on my toes, where it will remain until the last day of my trip. I'm also experimenting with it on my fingers, but I still want to avoid detection, so I'm being careful.

I feel so liberated, and so excited!

Fantasy: Girlfriends

[This was found in a separate file, entitled simply "Document."]


Some people love to lounge around the house in their underwear.  To them, it's the ultimate in comfort.  Personally, I like to lounge around in someone else's underwear.  

It began innocently enough.  I ran out of clean underwear of my own one day, and as a joke I tried on some of my girlfriend's panties.  We both laughed about it.  Me, of all people, with frilly silky panties on.  It was just so funny: the dainty little panty elastics, the extremely high cut, the little bow in the middle, the silk, the lace embroidery. . . it all looked so funny on my masculine body.  My big dig stuck out at the top like some offensive obelisk.  "You know, there's a matching bra for that," said A__, and she picked it out of her dresser daintily by one skinny strap, and dangled it in front of me.  She had to help me put it on, and that made us laugh even more.  It's one thing to wear ladies panties.  You can get away with it because they almost look like some pretty fruity men's bikini briefs.  But it's quite a different story when you're wearing a bra with them, much less a matching bra.  Then there's no mistaking the fact that you're wearing the most sexy, most intimate, most unmistakably effeminate part of a woman's wardrobe.  It was hillarious.  
Pretty soon, we were spent.  I moved to take A__'s underwear off me, but she stopped me.  "You can't do that!  You have to wear that all day!"

"Why?"

"Well, you don't have any of your own undies, do you?"

"So?  Who says I was going to put on some of my own undies?"

She stared at me, shocked, and we both burst into laughter again.

We both got such a laugh out of it.  She humoured me, as I had just humoured her, and she started digging through her dresser for the sexiest lingerie and swimsuits for me to wear, just for the laughs.  I couldn't back down now.  Besides, it was actually pretty fun.  We were doing something silly, just for laughs, and neither of us felt uncomfortable or ashamed.  I don't even think either of us thought twice about it.  It was a spur of the moment event.  Not too many people would do this kind of thing.  I think most men would be afraid of looking like pansies, and most women would be eternally turned off by the pansy men wearing their clothes.  But not us.  We enjoyed it for what it was.

A__ started piling all sorts of sexy stuff in my arms, all enthusiastic about how funny it would be to see me in a bikini, or a garter belt, or a nightgown.  Pretty soon, I started pointing out some of the lingerie I had bought her.  I don't know, in retrospect, how we kept this going.  Neither of us was entirely serious, yet neither of us would stop taking the joke further.  If either of us expected it to go so far at that moment, we didn't let it show.

After a while, I had all sorts of myterious girlie stuff in my arms.  I didn't even really know how to get into some of it.  Nevertheless, I remembered A__ wearing each and every one of the outfits, and how I drooled all over her when she did.  Each piece she handed me made me imagine her in it, how it would accentuate her most feminine features.  

I was beginning to get nervous, I think.  I had always been curious about her underwear.  Why do I find her so sexy in her underwear--even more so than naked?  There is something so inherently female about women's underwear.  I was even more curious now, considering that I would soon be wearing all of these dainty garments.  I wanted to know how it must feel to wear these things, just as all women do every day.  Imagine being sexy enough to have such beautiful clothes on all the time.  

"You know, I don't think I'm ready to do this," I said.

"What do you mean?  You don't want to wear this stuff anymore?"

Again, I couldn't back down.  "No, I mean, what's the point in dressing like a girl if I don't really look like one?"

"Yeah, let's get some of that hair off of you.  It would just look awful under stockings."

She pulled me into the shower, where she naired my body bald.  "If we're going to make you a girl today," she said, "we might as well go all the way."  Quite quickly, I could see my bald body.  It was as sleek and smooth as hers.  I could picture a garter on one of my thighs.  I could look pretty sexy, too, if I put my mind to it.  And I had so many options waiting for me. . .

As soon as I was dry, I slipped into A__'s bikini.  The sensation of the little skimpy tight and smooth material against my bald skin overwhelmed me.  Something came over me.  Neither A__ nor I found it funny anymore.  I stood there, tall and proud, snapping my bra straps in front of her.  I stared deep into her eyes, and she understood me completely.  This was no longer a game.  This was no longer for cheap laughs.  This had become serious.  It had become a matter of necessity for both of us to turn me into a girl.  I never felt such freedom as when I put that bikini on my hairless body--the same bikini that, when A__ wore it, made me salivate and lust for her as it clung to her delicious curves.  Here I was, putting on something too feminine for many women to feel comfortable wearing, putting it on right in front of the woman to whom it belongs.  I wore it because I was curious.  I wore it because I thought it was pretty, and I wanted it to make me pretty, too.  I felt no hesitation.  At that moment, I needed to know how it feels to be feminine.  I felt no shame.  Only pride.  I knew that I was far from pretty; there was still lots of work to do.  I was proud because I felt so comfortable.  I can imagine how I could have felt ridiculous, or ashamed; but I only felt the excitement of discovery.  

For so many years, I had admired women and their bodies and their sexy underwear.  I had often marvelled at the complexity of their outfits, and at how incredibly beautiful they look.  Panties lying on the floor, a bra dangling from a chair--these had all intrigued me.  I couldn't ever imagine wearing them myself.  They belonged to a world that I could never access without undermining my manhood.  Almost by accident, I dared to explore.  It was just a silly joke!  And now I stood here before A__, snapping my panty waist girlishly, dreaming of wearing all the most girlish things imaginable.

From then on, A__ worked feverishly to make me more girlish.  She did my hair and my nails and my makeup.  I tried on all of the outfits she set aside for me.  I settled on the lingerie outfit I bought her for Christmas: a matching black outfit consisting of a silky bra, panties, garter belt, and stockings.  I remember sweating with nervousness when I bought it.  It turned me on so much, because it was so feminine. And now I couldn't resist wearing it myself.  Then I picked out a tight little mini-dress.  We stuffed my bra a bit, to give me a bit more shape.  I felt so amazing.  I gushed with joy.  I felt so comfortable with A__.  I owed her so much for helping me discover my feminine side.  The word 'girlfriend' took on a whole different meaning.  We were ready to show the world.

We had to buy me some girly shoes.  A__ had nothing that could possibly fit me.  It was amazing that I even fit into her dress.  "You can't come with me, though," she declared.  "You need shoes, and you can't go out wearing anything but girlie shoes dressed like that.  What's your size?"

This was fine with me.  I was a bit apprehensive about going out.  I mean, someone might see me.  I only wanted A__ to see me like this.

She was only gone for half an hour.  She didn't come back with shoes, either.

"Bobbie, this is Ken.  I met him outside the coffee shop."

"Nice to meet you, Ken," I said in my most effeminate voice.  I felt so girlish.  I had worked myself up so much to this, that I blushed at the thoughts crossing my head.  I didn't want to abandon my girlishness.  I was glad that A__ had brought some stranger to see me first.  He seemed oblivious.  "Can I get you a drink?" I offered.

"Sure."

A__ followed me into the kitchen.  "So," she whispered in my ear, "moving in on my territory already, are you?"

"What do you mean?  I have no idea what you're talking about!"

"I'll bet.  You've been a girl for less than a day, and already you want a dick."

I must have blushed.  I felt a wave of horniness as I imagined the consequences of her statement.  The thought had, in fact, crossed my girlish frame of mind.  I was still quite afraid to admit it, even to myself.
"Look, I brought him here because I wanted you to experience every aspect of girlhood.  I thought I might show you a few tricks. . ."

Sure enough, when I brought him his drink, A__ snuggled up to him, and motioned for me to do the same.  She grabbed his crotch and purred, "so, you wanna have a threesome?"  I had never seen her so unabashed before.  She unzipped his fly and pulled out his cock.  She invited me to stroke it.
I had never even dreamed of touching another man's dick.  But this time, I wanted it.  I wanted to squeeze it like it were my own.