It was Friday, and that meant an entire weekend in front of me. I had already determined to spend it as Cayley. Not just for fun—I had a purpose in mind. If I was going to masquerade as a woman at Belmont House, I needed to know that I could do it. That meant practice, and if there was one thing I knew as an artist, it was the value of practice.

That night, I watched a series of tutorials on YouTube. Hair. Makeup. Fashion. If it had to do with the care and feeding of the female body, I watched it. Some of the videos were clearly intended for young girls, just getting their periods for the first time or learning about how not to overdo their makeup. Others were more advanced, subtle tips and tricks that I had not previously conceived of.

So much for theory, but what about practice? As it turned out, I had all of the supplies I needed already in the bathroom cabinet—so long as I was wearing the necklace. Saturday morning, I applied and removed makeup a dozen times, until I was confident that I could do it without looking foolish. In a sense, this was just another art project, my face just another canvas. Yes, the skills were specialized, but this was just color matching and blending and shading and staying between the lines. I could do this.

I also addressed my body hair. I had been shaving my face since I was thirteen, and I was accustomed to a fine crop of curly hair pretty much all over. The smoothness of my skin was almost as foreign as the curves it contained. My leg hair now was far more sparse than I was used to, short and spiky. I nicked myself twice, and missed so many patches that I had to do the whole thing again. The armpits were easier at first, until I realized that I had given myself a fair bit of razor burn. That gave me pause before I tackled the pubic area, but with time and gentleness, I set it right.

In the afternoon, I pulled every scrap of clothing out of my closets and drawers. It was the variety that stumped me at first. As a man, I could easily divide out work shirts and work pants and casual shirts and jeans, underwear and undershirts and socks. But as Cayley, I just had so many more categories to work with. Was that skirt casual or for work? Or both, depending on what I wore with it? I had easily four times as many shoes now, but way fewer T-shirts.

I tackled the chaos by starting with the dresses. They were the easiest, requiring only the right choice of bra, so as not to show through, and some shoes. Once I had put the dresses away, I turned to the skirts and slacks. There were fewer of these than there were tops. For the most part, I seemed to favor single-color garments on my lower half, although a pair of flower-print jeans were a clear exception, and one that I did not successfully match up with anything.

The other jeans were simple, since they were an article of clothing I had some familiarity with. As the sun fell to the west, I had gone through every bit of clothing I had, and found one orphaned sock, a slutty Halloween costume, and a matching nightie and panty set that couldn’t have been anything but sexy lingerie.

I blushed the whole time, but I tried it on. Only a rising flush that I began to recognize as sexual arousal snapped me out of my mirror-gazing trance, and back to my inventory.

On Sunday, I made up my mind to go out into the world. I hadn't interacted with anyone yet, except for Janice. If I was going to pretend to be a woman, I needed practice at being treated like a woman, and treating others as a woman would treat them. And so I picked out an outfit (jeans, a nice top, and sneakers), grabbed my purse and keys, and left.

The driver’s seat of my car was already pulled forward, but it still took a minute to get used to driving. I was lower down than I was used to, and the seat belt cut across my breasts in a very distracting way. Still, I had two legs and two arms, and they worked the pedals, gearshift, and steering wheel just like they always did. By the time I got to the mall, most of the feeling of strangeness had faded.

The mall was an entirely new place for me now. I had not noticed before just how many of the stores catered to women’s clothing. My eyes had always just sort of skittered over them without paying much attention, but now each one had potential.

Mostly I window shopped, responding politely to the saleswomen who approached me. In a few places I lingered, though. I had never walked by Victoria’s Secret without feeling like a pervert, much less spent any time inside. Now, I took a deep breath and steeled myself to penetrate that inner sanctum of womanhood. It was the ultimate test of my disguise, in a way. If I could act like I belonged here, I could manage it anywhere.

A saleswoman approached me. “Can I help you with anything today?”

“Yes, I was looking for a bra fitting?” The words came out before I had thought them through. I had just read a sign advertising the service, and it just bubbled out.

“Certainly! What size do you wear now?”

I hadn’t thought to look, but I could ad lib. “It varies, you know? It’s hard to find anything consistent.”

The saleswoman — Ellen, by her nametag — nodded sympathetically. “Guess that’s why you’re here. Let’s get you to a fitting room.”

The two of us entered one of the larger fitting rooms. I stood there stupidly for a moment, until Ellen spoke up. “I can get a better fit if you take your shirt off, but if you’re not comfortable....”

“Oh! No, that’s fine.” I did blush as I removed my shirt. It made me wonder what I thought I had to hide. It’s not as if I had spent my entire life covering up my chest. As a man, I could have taken my shirt off in front of this woman without any fear. So why did it bother me now?

I felt a tug at my neck, and realized that in my distraction, I had very nearly taken the necklace off. Now wouldn’t that have been a disaster. My hands shaking a little, I tucked the cord through the neck of my top. “I don’t like taking it off,” I replied to Ellen’s questioning look. “I’ll hold it out of the way.”

She took several measurements, around the base of my chest and across the widest part of my bust, but also up my collarbones and down my shoulder blades, and several other obscure measurements. At one point, she peeked at the tag on the bra I was wearing, and made a tutting sound. She left me there for a few moments, returning with a selection of bras, lacy and smooth, laying them over the top of the door and remaining outside.

“Looks like you made the classic error. Most women wear a larger band size and smaller cup size than they need. I don’t know how you’ve been cramming yourself into a B cup. Try these.”

I checked out the labels, which read 32D. Jesus, I must have been bigger than I thought. I removed my own bra and saw that it was a 36B.

I fumbled, but eventually managed to get the first new bra settled on. Not that I had a great deal of experience, but it did feel better, snug and supportive. Ellen asked if I was ready, and she came in and adjusted the shoulder straps for an even better fit.

I tried on several styles. One was smooth with very full coverage, very comfortable. Another was cut diagonally over the cups and showed a great deal of flesh. I felt pleasantly scandalized. The last was a push-up model — in Ellen’s words, “however much you’ve got, sometimes you want a little more.” It made me look huge, pushing my breasts up and together, and filling in underneath with padding. If I ever wanted to work in a German Biergarten, I knew which bra I’d wear.

Yes, I bought it. I bought all of them, some in several colors, as well as some yoga pants that looked nice. Ellen waved me out with my pink bags and told me to come back if I needed anything else.

My only other purchases were a sun dress, sunglasses, and a big floppy hat. It was a look I had always found attractive, but did not seem to have back at my apartment. I could see why women wore them in hot weather, too. Even though the dress had a long skirt that came down to the middle of my shins, the thin cotton fabric made it feel like I wasn’t wearing much of anything. The sleeveless top and low neckline only added to the sensation. How was it that I could feel so self-conscious, and yet so comfortable at the same time?

Probably, I reasoned, it was because all of this really was a disguise. It was like I had unlocked a new character in a video game, and was going through all of the new costumes that were suddenly available. I felt exposed in wearing something so revealing, but at the same time, no one who was looking at me would see me, Ben Davenport. It gave me an exhilarating sense of getting away with something clever.

And there was more. As an artist, I loved experimenting with new visuals. Suddenly, I had an entirely new canvas to play with, a completely new medium. I found that I rather enjoyed it.

I left the mall weighed down with my purchases. It had been a successful outing. I had been implicitly accepted as a woman everywhere I went. That felt strange and new and wonderful.

But I got home, and suddenly it was Sunday night. I had a whole week of work ahead of me, just my usual dull life. I supposed that I could spend one more night transformed, but to what purpose? Better to get accustomed to my usual body again before work. I tugged the necklace off, and Cayley’s body fell away.

The clothes I was wearing changed back. Interestingly enough, my new purchases did not change. I had wondered if they would become some analogous articles of men’s clothing, but no, they resolutely remained as hats and dresses and bras. I pushed them into a corner of my closet, still bearing their tags. They would be there for later, so long as I remembered not to change back while I was wearing them.

I got into bed. It felt small. My body felt clumsy and ungainly as I tried to find a comfortable position. My unshaven face scratched against the pillow in a way that annoyed me, even though it felt like that every night. In my dreams, I was looking for something, though I didn’t know what it was, and I never seemed to be able to find it.