It felt a bit weird putting the wig back on after not wearing it since the day date. It still had a bit of curl to it. For a cheap wig, this thing was holding up surprisingly well. The lace front actually made the hairline look really natural. Still, I knew the synthetic hair would not hold up to much more treatment or abuse. Apparently you’re not supposed to use heat products on cheap synthetic wigs according to what I read online. Oops. Maybe it was time to come clean about the hair. But it did look a lot better than my normal short hair. More like Madison.

Still, it was strange that there was a girl who looked so much like me. I wonder if she had a lot of issues with being confused for a guy? Probably not with that hair. Or those legs. I glanced down at my own legs and noted that they were starting to show some stubble. With a frown, I slid the wig back off my capped head and pulled off the wig cap, as well. Might as well shave them again.

“Mom! I’m gonna hop in the shower to shave my legs!” I called down the stairs. “Apparently Emily wants me to wear something cute, whatever that means.”

“All right. Remember to use the razor I gave you!”

I grimaced. Did the razor really matter that much? As I turned on the bathroom light, the ceiling fan roared to life, drowning out any other sound. My eyes settled on the razor Mom had bought for me last night on the way home, now resting on my side of the bathroom sink. It was packaged in gratuitous pastels and the design on the box emphasized feminine iconography such as flower petals and elegant cursive typography. 

For the night of the bet, I had just picked up some cheapie disposables from the store but found out that even with shaving gel, there was a high propensity for nicks and cuts. I might have gotten away with the longer denim skirt at the restaurant last night to cover my leg hair but today I was wearing an outfit that Emily had picked out for me and it showed a LOT of leg. It was best to just suck it up and use the one Mom got for me if I didn’t want to spend an hour staunching blood flow. Oh well. It’s not like using a ladies’ razor was gonna make my dick fall off.

And I’ll be damned if the over-priced pastel purple razor didn’t do a better job at hair removal than those yellow BiC single-blade razors I’d picked up before. I doubted the purple had anything to do with it, though. It was more likely the moisturizing strips and the additional blades on the head. Still, I stepped out with only a couple small nicks versus looking like I was mauled by a feral raccoon.

I went through the rest of the chore of exfoliating, washing, rinsing and drying before I finally stepped back into my bedroom to lotion up and get dressed. Seriously, the amount of effort women put into keeping their skin looking soft and smooth was commendable, if daunting. Was Maggie doing this? Nah, she was pretty young, yet. It probably wasn’t this much work for her. How about Mom? She still looked pretty youthful for early forties. She was probably doing all this every day. But why? Dad wasn’t around anymore, and it’s not like Mom has been looking for someone to date. Maybe to keep up appearances? For personal gratification? I shrugged and shook my head to clear my thoughts. Fact was, women were pressured to put a lot more effort into their appearances than most men. If nothing else, this experience has taught me to appreciate that much.

I dressed, taking care to tuck as I had done on my first “date” with Emily. It wasn’t really a date, though. It was just two chicks hanging out. Just like tonight. Two chicks hanging out. I let out a long sigh as I stared at myself in the full-length mirror hanging from my closet door. I hadn’t put on any makeup, yet, or done much of anything with my hair. So here I was, a twenty-one year-old man, wearing a pleated green plaid skirt and a long black v-neck tee. Granted, I was still wearing the padded bra, but the incongruity between the appearance of my body and my naked face was making me feel uncomfortable. Confused.

Dysphoric?

Nah, that wasn’t it. It was probably just me being uncomfortable with my head attached to this weird feminine-looking body. It was the outfit that was making me feel strange, not my face and hair. Speaking of my hair, I brushed it out and then put on a headband so I could start working on my makeup. I didn’t do a whole lot, really. Just a bit of concealer for the facial hair shadow (such as it was) and a bit of contouring to soften my jaw a bit. Because I had a lace-front wig, I needed to put that on before I did the rest of my makeup. Finish up with a touch of neutral eyeshadow and black mascara to put a little emphasis on my eyes, and then smooth out the complexion with some foundation and finishing powder. Bam. Done. 

I looked… rather cute, admittedly. If I didn’t know better, I’d swear this is roughly what Madison would look like in this outfit. I felt a weird pang at that thought, but since I couldn’t pinpoint the reason, I put it out of my mind. The heels I’d worn for “bet night” rounded out the outfit and propped me up a few inches. She said she wanted me to look cute, right? There was one last thing I needed to complete the look, then. I headed for the stairs, remarkably sure-footed despite the footwear.

“Mom? Can I get a hand with my hair?” I called down the stairs.

“Sure, sweetie. Give me a minute and I’ll be right there!” 

I went back to my desk and sat down in my chair, taking care to cross my legs at the knee to avoid giving mom an eyeful of my crotch when she came into my room. I fiddled with my phone for a minute, not really paying attention to anything in particular.

“Oh my god, you look adorable,” Mom said abruptly as she walked into my room. “Although your foot’s going to go numb if you keep your legs crossed like that.”

“Huh? Oh. Yeah, I guess so. I just didn’t want to like… show anything,” I admitted.

“I appreciate that! But there’s a more comfortable way to go about this. Here, let me show you,” Mom said as she walked toward me. She tapped the side of the knee going over the lower leg, motioning for me to uncross it. I did as I was instructed. “Okay, now cross your ankles but keep your knees together.”

I gave a curious frown but did as I was told. I could already tell that this was more comfortable, without the weight of my leg cutting off circulation from the knee down. “Huh,” I muttered.

“Oh, we’re not done, yet, young lady. Straighten your back. I want you to sit upright. Chest out.” Mom stepped to my side and pushed the middle of my back forward and pushed my shoulders back. “Good girl. Now put your hands in your lap, one over the other.”

“Mom, are we forgetting that I’m actually a guy?” I reminded her in a dry tone. 

“Nonsense. While you’re dressed like that, you’re my daughter and that’s how I’m going to treat you.”

I rolled my eyes. This was honestly why I didn’t want to dress like this in front of Mom in the first place. “All right, all right. But I didn’t call you in here for etiquette and posture, I just wanted some help with my hair,” I reminded her. “And you don’t make Maggie do all this! Most of the time, she’s hunched over her laptop like some kind of goblin!”

Mom leaned over to look me in the eyes. “When Maggie is gaming, she can do whatever she feels is comfortable. When she’s dressed up, she knows how to comport herself. I expect no less from you, Lauren.”

Chagrined, I forced a smile. “Okay, Mom.” Suppressing a sigh, I asked again, “Hair?” while pointing at my head.

Mom studied me for a moment before her face lit up with a grin. “I’ll be right back, I have just the thing!” She darted out the door, leaving me in stunned silence before returning with a wide-tooth comb and a small plastic box which she placed on my desk and opened to reveal an assortment of scrunchies, hair bands, and other miscellany.

“What’s all that for?” I asked.

“Your outfit has a certain vibe, a certain look, a certain je ne sais quoi. I’m just going to accentuate that with the right hairstyle and accessories!” Mom said excitedly.

She quickly set to work. She began by combing the wig into a dramatic side part, pulling and pinning the bangs above my ear while she focused elsewhere. As her fingers danced in my fake hair, she began humming a lullaby I hadn’t heard since Maggie was in Kindergarten. Nostalgia swept over me and I closed my eyes to listen to the melody. It wasn’t anything I’d ever heard elsewhere, probably a song Mom had made up when I was little. I concentrated on the notes for a moment and the words bubbled up to the surface of my memory.

“Sleep well, my little darling

Sleep well, my lovely child

Dream well of sunny mornings

And days with weather mild

And all the happy laughter

To chase away your tears

Sleep well, my little darling

We’ll protect you from your fears.

“Grow strong, my little darling

Grow strong, my shining light

Be strong in times of darkness

And let your soul glow bright

And share your light with others

They’ll share theirs with you, too

Grow strong, but never rigid

We will always love you”

A wistful, longing feeling welled up in my heart and I felt as though I was remembering something else, something important. But just as quickly as I caught a glimpse of that hidden memory, it slipped from my grasp.

“Done!” Mom announced, startling me from my reverie. “Here, don’t get up. I want to push you over to the mirror exactly as you look right now.” She stepped around behind me and pushed on my computer chair, guiding me over to the mirror in front of my closet.

My breath caught in my throat. Staring back at me from the mirror was what looked like high school aged Madison. Her bangs had been pulled to the side and braided back into a longer, thicker fishtail braid that flowed over the opposite shoulder, an emerald green scrunchie holding the braid together at the end. The fishtail braid had been teased a bit to make it look fluffier. She had finished the look off with a silver crescent moon hairpin where the bangs flowed into the smaller side braid. Eyes wide with surprise, I looked back at Mom.

“What is all this? I was just expecting, like, a ponytail or something…” My voice trailed off a bit and I realized with a bit of shock that I had unintentionally pitched my voice up slightly. “This is way too fancy. It doesn’t look right on me.” My heart had started hammering in my chest and my breath was coming out shallow and quick.

Mom laid a reassuring hand on my shoulder. “It’s not too fancy. And it looks just right on you. And I would say the same of short hair or jaw-length hair or even a mohawk. Okay, maybe not the mohawk, if I’m being honest. But if that made you happy, I would support it.” She smiled warmly at me in the mirror. “Just look at this as a fun chance to experience things you never would have and try not to overthink it too much, okay?”

I nodded numbly, still taken-aback by how much just a hairstyle had changed my appearance from chic to cute. My legs were still crossed at the ankles and my hands still rested in my lap. Even I had to admit that in this moment I looked like a girl. And for some reason, I didn’t feel as much resistance to this idea as I had before. Was I becoming some kind of weird gender-bending narcissist? 

“Now go on, you don’t want to keep that poor girl waiting for your indecisive butt,” Mom said as she gently pushed on my shoulders to urge me from my seat. 

I stood up, now looking down at my mother and smiled. “Might as well enjoy this while I can, huh? After I tell Emily the truth about me, it’s not like I’ll have any reason to dress up like this anymore.”

An odd expression flitted across my mother’s face before she returned my smile. “You don’t want to miss lunch. Send me a text when you get there so I know you made it safe.” With that, she stood on her toes to kiss me on the cheek.

Twenty minutes later, my little red Chevy Sonic steered into the driveway of an imposing three-story Victorian home. If I’m being honest, it wasn’t quite what I’d expected from the way Emily had described her family’s money. Then again, it was situated on a large corner property with a horseshoe driveway cutting through an immaculately-manicured lawn and fenced in by imposing wrought-iron spikes. The house had clearly been renovated - the dormer windows had been replaced with modern black-framed multi-pane panels. The gabled roof was bereft of the ornamentation representative of the architectural style and the whole building had been painted in cool grays, black, and white trim. It was a striking visual, but it also felt a bit lonely. And if you’re wondering why I know so much about Victorian home design, I’d just like to remind you that I work for a home-improvement and hardware store.

Emily’s text had instructed me to pull past the house to the clearly-aftermarket attached garage. There was a paved space to the left of the garage that was intended for guest parking. I pulled into that space and killed the engine, glancing once more at my phone to make sure that I was at the right place. Yep. 17221 Edison Street. Deep breath. Sent Mom a quick text just saying “Here. Made it safe.”

I stepped out of my car and straightened my skirt. Now that I was actually here, I was starting to get cold feet. I didn’t have too long to worry, though, because Emily came running out the front door of her house with a very loud, “OH MY GOD YOU’RE SO CUTE I COULD EAT YOU!”