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!