Chapter 12 – The Preparation
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Makeup is hard work! Seriously, how the hell do people do this all the time? I had to hand it to my sister, she made this look easy. After two days of practice, I more or less had a satisfactory look down. True to my word, I refunded the money Jeff had sent me. As a result, paying for my own makeup was costing me a pretty penny. Why was this shit so expensive? And society pays women less than men on average? I had spent around $120 just to achieve a “natural” look with defined brows and lashes and a little bit of lip color. I honestly didn’t have any noticeable facial hair growth, but I still had a little bit of shadow to cover. Maggie insisted I didn’t need false eyelashes as mascara was sufficient for me. I took her word for it.

As for the outfits, since Emily had already shown me how to coordinate them, I already had a fair idea to make things work for me. Apparently, I had “enviously narrow” shoulders according to her. I really wasn’t sure how to take that. I had always understood broad shoulders to be an attractive masculine trait.

The biggest hassle was wig maintenance. The long wig looked nice on me, but it was showing a bit of wear and tear after wearing it several times. Maggie had sent me some links on basic wig care. I had only worn it a couple times, so far, so I didn’t need to wash it yet, but I did need to handle it better and brush it. Honestly, this was probably the one thing that annoyed me most. It was like taking care of a long-haired pet without the affectionate cuddle time.

Okay, I petted it. I know it’s weird, but come on!

At any rate, I more or less had a “look” down so that I could keep this up without being such a huge imposition on my sister (or anyone else for that matter.) And I looked pretty good, too. It wasn’t bad for two day’s worth of practice. Granted, I also had work and classes mixed in there, but without the usual weekly basketball games, I had a fair amount of time to practice. Plus, Maggie spent some time with me to critique my results and improve my technique. 

With what I had learned and with what Maggie coached me, I even managed to offer some useful advice to my store manager, Rebecca who was now rocking some more defined eyes and contoured cheekbones much to everyone’s surprise and approval. She genuinely seemed more confident at work, her smile shining through some of the tougher situations she encountered. I advised her on a different cut of slacks that was a bit more flattering, but still professional. Where before she was wearing a pair of men’s-cut Dickies, I’d given her the address for the Duluth Trading Company retail store and suggested she try on some of their offerings. She found a comfortable pair of bootcut pants that were surprisingly stylish for work pants and the waist sat more naturally on her body.

In an attempt to prepare for my outing the next night, I was sitting around the house dressed fully en femme minus the wig. The high-waisted denim skirt I wore created the appearance of a more hourglass-like shape while the cropped, off-shoulder knit top gave a peek of baby-blue bra strap for what my sister called a “flirty” look. I needed to be as comfortable and natural as possible while wearing this, so my family kept me company in the living room. Mom sat in the recliner at the end of the coffee table while I was on the couch with my legs tucked under myself and Maggie was next to me, leaning her head on my shoulder as she played on her phone.

We were watching some ridiculous show about novice bakers making terrible desserts and the on-screen results ranged from hilarious to stomach-churning. As a result, I found myself playing on my phone and just listening to the show as Mom periodically punctuated the show with her infectious laughter.

I was in the middle of scanning an article about some political issue in Texas when a text notification popped up.

Chris: Hey dude, haven’t heard from you in a few days, you doing okay?

I felt my face flush a bit, embarrassed that one of my “guy friends” was talking to me while I was dressed up as a woman at home. Despite that, I casually replied:

Me: Yeah, taking a break from social stuff, just focusing on work and school

A minute or two went by when another message popped up.

Chris: That’s cool. Hey, you still cross-dressing or whatever? Jeff won’t shut up about it.

I stared at my phone, trying to decide how to respond. I must have been making a weird face because my mom suddenly said, “Sweetie, if you keep frowning like that, you’re going to give yourself wrinkles.”

Startled, I looked up from my phone toward my mother, who was giving me a sly smile. Oh. It was a joke. So why had I panicked? Whatever. I sighed and replied, “Just got a text from Chris wanting to know if I was still cross-dressing. Apparently Jeff is still obsessed. I have no idea how to reply. Like, is he just gonna report it back to Jeff?”

“So what if he does?” asked Maggie nonchalantly as she executed some ridiculous combo attack in the game she was playing. “You’d think Jeff would try to distance himself from you as much as possible if he genuinely thought it was gross.”

“The lad doth protest too much, methinks,” my mother quipped. Even I recognized the paraphrased Hamlet quotation. “It’s up to you how to respond. How well do you trust your friends?”

I mulled it over for another minute or two before finally replying.

Me: Actually, yeah. I’m surprisingly hot in a kinda androgynous K-Pop idol way

Chris: No shit? That’s kinda cool. Got a pic?

Me: Nah, man. Don’t want anything spread online. 

Chris: Ah. Makes sense. Well I’m still your friend if you wanna hang. Kinda miss playing bball even if you suck

Me: Oh fuck you! I’m still better than Tim

Chris: Yeah and 1 is more than 0 but still less than 100!!!

Me: Pfft. Asshole.

Chris: Don’t be a stranger

Me: I won’t

I leaned my head back against the couch and looked up at the ceiling. Was I really doing this? I mean, this was stupid, right? Dressing up like a girl to hang out with a girl because I’m too chicken to tell her that I’m really a guy? She didn’t seem judgemental at all. Quite the opposite, really. So what was the big deal? Why was I so scared to tell the truth?

The episode that Mom was watching on Netflix had ended and rather than just playing the next one, she asked, “Wanna go out for dinner?” There was a playful tone in her voice.

“Sure!” exclaimed Maggie, suddenly sitting upright on the couch. “What sounds good?”

“Woah, woah, woah, wait!” I cried. “I need to go get changed and wash my face.”

Mom tilted her head innocently and smiled. “Now, Lauren, I think you look just fine as you are.”

I closed my eyes and let out yet another long sigh. “I’m not getting out of this, am I?” I asked in resignation. “Fine. I don’t think I’m super recognizable as I am, anyway. Can I grab my wig, at least?”

Mom shook her head. “Nope! Now get up and grab your shoes, we’re going out for some Chinese!” Maggie darted off toward the garage entryway and let out a girlish giggle that sounded suspiciously like my own. I just shook my head and began walking in the same direction with Mom following behind me. She leaned up close and said in a low voice, “You seem comfortable enough at home, so I thought you could use a bit more practice outside.”

I frowned and looked at her as if she had suddenly sprouted another head. “You do realize that tomorrow is just friends hanging out at home and playing video games? And that I fully intend to break the news to Emily that I’m actually a guy?”

With a devil-may-care shrug, Mom grabbed her purse off the kitchen island and slipped her phone inside, motioning for me to grab my purse as well. I complied, unable to decipher my mother’s intent. As we stepped into the garage, Mom finally said, “I’m all for telling the truth, but before you say anything to her, I feel like you could use more of a chance to figure out what your truth is.”

“Mom, what are you even talking about? I’m a guy who happens to be cross-dressing for a comically-stupid reason,” I countered.

“Michael… Lauren… I love you. And normally you are a very intelligent and self-aware person. But I don’t think you’ve noticed that you changed your inflection and movement once you got into that outfit. I can’t decide if you’re just that thick-headed, or if you have the worst case of denial since that river ran through Egypt.”

My jaw dropped. “Mom. Did you seriously just dad-joke me, right now?”

She lifted her chin haughtily and put her nose in the air. “I’ll have you know, young lady, that there is no gender requirement for the enjoyment of corny jokes and bad puns! Besides, I was always funnier than your father.”

I thought back on that. My memories of Dad were bittersweet, but I remembered him being very soft-spoken, very caring and empathetic, right up until things went downhill. I laughed a bit, realizing that Mom was right. She was always the jokester, the punster, the tickler, and the snarky comments. I hugged her from the side in appreciation. “So which Chinese place are we going to? The one with the panda or the one with the Great Wall?”

It was Mom’s turn to feign shock and stare at me with mouth agape. “You wound me, child! Would I really do such a disservice to my daughter on our first outing together?”

One of my eyebrows shot up in curiosity. “Wait, are we going to the sit-down place downtown? I thought we were just grabbing takeaway!”

“Oh, please. It wouldn’t be an outing if we didn’t get a chance to sit down and talk to each other without our phones in our faces.”

Maggie’s voice echoed from the garage, “BUT I’M NOT FINISHED WITH MY DAILIES!”

Mom’s tone shifted to full-on Mom authority. “Exactly!”

I slipped the ballet flats I’d purchased for my first outing with Emily onto my giant man-feet and we were out the door.

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