Chapter 09 - Clothes shopping

It turns out that only by having extensive time wearing a corset or faja, can it actually make any type of permanent change to one’s body. At least that was a relief.

Even with setting my alarm to get up earlier than yesterday, it still took me longer to shower, shave, lotion, and put on my makeup. And that’s without doing anything with my hair other than changing the ponytail to a tighter one up toward the top of my head.

Grace reminded me that while I’d get faster as time goes on, it simply takes women longer to get ready than it does men, and they normally weren’t squeezing into a faja like I was. I had to begrudgingly agree as half these things I was doing just as ‘maintenance’ for my skin were things I’d never consider doing in my normal life.

After slipping into the tennis shoes, promising that I’d practice the heels tonight, Grace and I make our way back down to the Loop and to the second-hand store we’d intended on hitting yesterday, Thrifty Office Styles. On our trip downtown, both on the train and walking down the street, I kept focusing on other people. Normally I don’t look at others around me except as objects to avoid walking into. But now all I can wonder is what they think of me. Am I a guy in drag to them? Am I a woman? Am I stylish? Pretty? Out of place?

As we stepped into Thrifty Office Styles, I think I had the best answer that I could have hoped for. No one took any special note of me. I didn’t stand out as a pretender or as a sex object. I was just another woman on the street.

While looking through the skirts and blouses and accessories, I tried to chat more with Grace. Both to keep my nerves on an even keel and to keep my vocal cords getting used to speaking in this register. I had to have this voice down so that if someone startled me or I spoke suddenly it would be with this voice and not my normal ‘Jamie’ voice. It turns out we didn’t have to make too many choices when it came to clothes. There just weren’t enough selections available in my size that weren’t either too conservative or too slutty. I ended up with six skirts and eight blouses, most of which could mix and match. A lot of the skirts had fairly high waists and all of them were skin tight around my hips and ass. Whenever I bent forward or crouched down, I was sure to be giving someone behind me quite a show. Grace assured me that it not only looked fine from behind me, but it was also quite attractive.

We added some jewelry, bracelets, a few rings, a couple ankle bracelets, and a necklace, but didn’t go overboard. Outside we walked several blocks before turning down a particular alley. There weren’t any markings, but it must have been a known, out of the way, marketplace as just behind the one building was five or six different booths set up with crooked looking guys selling all manner of fake luxury wear. Grace immediately took me over to a guy selling purses and picked out a couple for me. A fake Prada and a fake Louis Vuitton. After adding a pair of realistic looking, but still fake, Versace sunglasses that cost more than any eyewear I’ve had before, I asked Grace if it was going to be a problem carrying obviously fake designer items. Grace’s answer made sense though, “Not in the least. Most girls in your position dream big and having fake bags is no big deal. This will make you fit in more rather than a plain purse from Walmart! Just be careful with them as I’m sure they’ll fall apart fast.”

Next up were shoes. While I thought we might go find another fake luxury marketplace we instead ended up at a big box store with dozens of pairs to choose from. Again, Grace’s reasoning showed that I had a lot to learn about the female condition. “Look, you’re right. Someone like Paris would absolutely love great designer heels to wear to work. But knowing how much she’s going to be up and around on her feet, how much she’s going to be walking around and wearing down her shoes, she wouldn’t dare spend the money even fake designer heels would cost. Plus, it’s easy to find shoes that look similar enough to evoke those same feelings.”

And she was right. I ended up with four pairs of shoes, all that Grace promised looked like designer heels. Three were three-inch heels while one was what looked like a towering four-inch heel. Grace said if I could manage to walk in those before we were done, they’d catch any man’s eye. And not the heels themselves, what they’d do to my legs and ass.

Only after we walked out did I realize that my feet were going to be particularly cold. Not only did these heels not cover much of my feet, only one pair actually covered my toes.

Next up was a specialty hosiery and lingerie shop. I almost fainted when I saw how expensive some of the lingerie was but thankfully, we stayed on the low end of that spectrum. We ended up with six sets, three of which would include a garter for stockings, and three which would allow me to wear pantyhose over them. Then surprisingly we seemed to splurge on the hosiery itself. Every set we got was real silk and cost a minimum of sixty dollars. The reason, when Grace answered me, shut me right up. “We want them to feel good when Mr. Orpheus touches them. Which he will. Repeatedly.”

After we walked out, barely able to hold on to all our purchases, we thankfully decided to call it a day. We could spend the rest of the day playing dress up at the apartment and make a list of anything else I’d need. Halfway to the train station I had to stop and spend a couple moments fixing my contact lenses. Between the wind, the sunglasses, and these damned lashes, I kept brushing against them. Once I was ready to go again, I made a spur of the moment decision that Grace agreed with. Just down a couple blocks we ended up at the little optometry shop where we picked out two pair of stylish, very feminine, glasses.

I couldn’t really risk having contact problems as I got accustomed to the makeup and especially the new lashes, but the glasses would solve that problem. In addition to fixing that problem, they’d be another layer of feminizing disguise.

My prescription is complex but it’s still something that they could make in house in about an hour. Grace and I found a quick place for a late lunch then picked up my new glasses and returned home.

Once we were home, Grace helped me unpack everything. It was easy enough as I didn’t really use any of my closet space for clothes. The fact that I could put all of my feminine finery in there was beyond convenient. As soon as the clothes were put away, Grace made sure I slipped into my pair of practice heels. For the rest of the day, the only time those heels came off was when I was putting on or removing my stockings or pantyhose.

Between all the combinations of hose, skirts, blouses, and jewelry, I must have tried on everything we purchased at least a half dozen times. Everything looked like it was made custom for me and fit like a glove. This of course was the look we were going for, but it was still disturbing to see it in the mirror. I looked like a woman last night. I AM a woman now. Not including variations of heels, I had at least a dozen and a half outfits I could wear. Some were just variations on a theme but the width and breadth of what we bought made sure that there were some spectacular outfits.

As soon as Grace started teaching me how to put on the hose and stockings, I realized how right she was. These felt absolutely magical on my baby smooth legs. Individually as they slid up each leg, as my hand ran along each stocking, and of course when my legs touched each other, silk on silk. It was enough to spike my arousal and almost make me rip free of my panties and gaffe.

By the time dinner was done, both Grace and I were satisfied with the progress we’d made. I was no longer worried about anybody seeing underneath the new hair or the makeup and finding Jamie. In no way did I look like the woman in the mirror. She was an entirely new person. I’d wager a good amount of money that my own father couldn’t pick me out of a lineup.

We had a small list of needed items. An umbrella. There’s that heavy wet quickly accumulating snow that people in the know use umbrellas for. Even I knew that women with styled hair wouldn’t want them getting wet and having to fix it when they got to their destination. And in case snow or rain came on suddenly, we added some hair scarves as well. We needed one more skirt as it would set off at least four more outfits, meaning I wouldn’t have to shop for clothes again. I needed purse accessories like tissues, keychain, pen, notebook, breath mints, and a microfiber cloth. And finally, we needed an outfit to ‘go out’ in. Neither my ‘comfy’ clothes nor my ‘office chic’ clothes would do for the test Ms. Birdie wanted. So, while I came very close to getting through this entire endeavor without an actual dress, we were going to buy one tomorrow.

The last lesson was Grace showing me how to take care of all my clothes and shoes. Even that was going to be different than my own clothing. We specifically chose clothes that could be washed and maintained at home, but doing so wasn’t as easy as tossing it all into the washing machine like I do my clothes. It certainly couldn’t be left unattended as it needed to go immediately into the dryer using cold air. Wrinkles were the enemy, and I’d have to fight them from getting on my clothes with the same intensity that most women fought to keep them from getting on their faces.

My hose and lingerie were all hand wash only. I’d often wondered why Grace bothered with washing her knickers in the kitchen sink and hanging them up in the shower but now I knew and would be doing the same thing a couple times a week.

The last thing before heading to bed was my realization that my feet hurt. Encouragingly, I also recognized that I hadn’t wobbled or almost fell over for the last three hours. I was getting good at walking in three-inch heels!

The early morning routine wasn’t getting any easier, but at least it wasn’t getting worse. I found that my routine wasn’t exactly like Grace’s in that I could get going faster if I started with some coffee before jumping in the shower or getting anything else done. For the sake of practice both Grace and I were ready to go by six in the morning, meaning we had to wait around for a couple hours before any of the stores we had to hit were open.

As we were going to get ready for Rhea, I agreed with Grace and decided to wear the skirt and blouse combination we got on that first day. The skirt wasn’t exactly showy, but it was still a lesson on how it felt to have the wind blowing up. And as I feared, the pantyhose provided no warmth whatsoever. Before lunch rolled around, we were back at the apartment dropping off the umbrella, scarves, another hip hugging secretary skirt, and a bunch of little kitschy items to go into my purse, including a burner phone. With all that settled we decided to go to a nicer place to look for some bar or club wear. It’s not that we wanted to spend the extra money, we just wanted the selection. Considering that one of our primary requirements is that it couldn’t show off my cleavage would certainly narrow down the choices, meaning a lot of the secondhand stores might not offer anything.

It was at the fourth shop that we found the dress. It was perfect, especially for this time of year. A cashmere sleeveless belted turtleneck bodycon dress in a bright eye-catching blue. The hem of the dress came down right between my hips and my knees with the belt making it look like my legs just went up forever. We added a stylish short leather jacket to provide at least the semblance of warmth and some navy-colored cashmere over the knee boot heels. We were lucky as they were the only boots that looked great with the dress that came in a three-inch heel. The obvious style for this was four inches or more.

We took everything back home and once again played dress up. While both the play and the costume party gave me a lot of time to walk around as a woman, Grace gave me specific pointers on looking like a sexy woman. Taking longer strides than I thought I should in these heels as it let the dress stretch around my hips and ass. Swinging my hips enough that with my stride my ass will jiggle on each step. I practiced tossing my hair over one shoulder or the other. I practiced smiling. Small smiles, big smiles, toothy smiles, sly smiles, winking smiles, laughing smiles. Per Grace, I shouldn’t ever NOT be smiling. And that wasn’t advice just for Rhea’s test, it was how ‘Paris’ should present herself in the office.

While I thought I could use another day to practice, Grace thought I was close enough and that any more practice might just get under my skin. She called up Ms. Birdie and suggested we meet at a smaller club up on Rush street. That would give us time to go now and hit up some other bars. Or in other words, let me get used to being looked at like a piece of meat.

Grace quickly dressed up in similarly appropriate club wear while I re-applied my makeup and teased out my hair a bit. When we were both ready Grace had us pose in front of the mirror for a chance to check us both out. I only realized later why she did that. It was to show me that out of the two of us, with my longer more eye-catching hair, with my larger breasts, and with my longer legs on my shorter body, I was actually the sexier of us.