Charlie in a Red Dress

by Zoe X Rider

  “You could tuck,” Jeff had offered.

  “Tuck what?”

  He’d stared at me till I got it. Walking around in heels sounded challenging enough without trying to keep my dick pinched between my asscheeks at the same time. “Should I be worried that you know about things like ‘tucking’?” I’d asked.

  Lydia spilled one of the breast forms from the packaging. She’d picked them up from Walmart for us. If I’d known those things existed, I’d never have guessed you could get them at Walmart. It looked like a jellyfish wobbling in her palm. She slid her other hand into my bra cup and held my moob toward the center of my chest so she could push the form in alongside it, her fingertips a little cool in my armpit.

  I tilted my chin toward the ceiling while she adjusted both me and the two breast forms.

  When she stood back, I looked down. At cleavage. “Shit. How’d you do that?”

  “The magic of push-up bras and silicone.”

  “That is pretty amazing,” Jeff said.

  I was dying to take a look in the mirror—I had cleavage!—but when I took a step toward it, he caught my shoulders and turned me back the other way.

  “I’ll leave you two to sort out the rest of the undergarments,” Lydia said. “Remember: it’s panties then hose. Never the other way around.”

  “Yes, ma’am.”

  As she pulled the bedroom door shut, the clothes hanging on the back of it swayed.

  “Promise not to laugh,” I said as I unfastened my jeans. I meant when I put on the panties, not what I had in my trousers. I was going to look ridiculous.

  But as my jeans came down, they revealed smooth, pale legs that didn’t look quite like mine. And I was looking at them over the swell of breasts. Maybe I was wrong; maybe I could pull it off.

  The feet, though, were all mine—size 11 in women’s, apparently. I stepped out of my jeans and looked at the tiny slip of red satin on the bed.

  Jeff was fiddling with something he’d picked up from Lydia’s dresser.

  I pulled in a breath and picked up the panties—cool against my fingers—and stepped into them. The waistband was little more than an elastic string, the panties entirely cut out on the sides. I pulled them all the way up, and had to tuck and arrange myself so I wasn’t bulging out the leg holes.

  Talk about self-conscious. I turned my back, even though Jeff was still politely not looking at me, and ripped open the package of hose. Control top, hopefully to control the bulge, but also because Lydia said it would shape me better. I sat on the edge of the bed, held a leg open, and stuffed my toes in like I would a dress sock. With a little tugging, I got the one foot in, then switched to the other.

  A moment later, I was standing on the carpet, certain we’d bought pantyhose meant for toddlers. The waistband hugged my knees, the crotch stretched between my calves. The fabric seemed dense and thick, not at all sleek and shimmery like the pantyhose I saw on actual women.

  “This is not going to work,” I said, and Jeff, who’d opened a book, looked over. And laughed.

  My face flushed.

  This just proved how ridiculous the whole thing was. For a minute there, I was starting to think we could pull it off—I could fool everyone into thinking I wasn’t Charlie Dixon.

  But I wasn’t even Eddie fucking Izzard. He, at least, was intentionally funny.

  “Hold on.” Jeff closed the book around his thumb and headed for the door.

  “Wait.” I didn’t want Lydia seeing me in the panties. That was a little too fucking revealing for my best friend’s big sister. “Let me get the slip on.”

  It was as silky as the panties, but black. I struggled to get it over my head. My elbows got caught up in it. It bunched up around my chest. Jeff helped me drag it down, until its skirt fell lightly around my thighs. Well, that was a little better. But I still felt like a tool with the hose around my knees.

  “Lyd,” Jeff called. “We need a little help.”

  The slip pushed against the breast cups, making me aware of every breath I took. I held my new bosom from the sides and looked down again, still kind of awed by the cleavage. I wished everything could go as well as the cleavage had.

  In a moment, the clothes swayed across the back of the door. Lydia came through saying, “What’s the—” but stopped when her eyes reached my knees.

  She burst out laughing.

  Jesus, this did not help.

  “Okay,” she said. “There’s a trick to that. Sit.”

  I sat. Kneeling by my leg, she slipped both hands inside one leg of the hose. “Lift your foot.” When I did, she started tugging and slipping, tugging and slipping. The fabric stretched thinner. The hose around my calf grew slack. When she got it stretched up to the bottom of my calf, she switched to the other side. Then back. Then over again. Once the hose had rounded my knees, making my lower legs sleek and shimmery, she got up. “You can take it from here, right? Don’t use your fingernails, and don’t pull too hard. Otherwise you’ll get runs, and we’ll have to move to the emergency back-up pair.”

  I waited for the door to close before getting up. The carpet felt strange through the flimsy film of nylons. I wiggled my toes as I bent forward, and started working the hose up my thighs, one side then the other, then back.

  “You’re getting a good laugh out of this, aren’t you?” I said without looking at Jeff. I heard a page turn, and Jeff said, “Not even paying attention.”

  The sense that my swaying ass was being watched must have been my imagination.

  I had to hike the slip around my waist to get the hose up. The bottom of the crotch still stretched across about three inches below my balls. I tugged and pulled until it managed to seat more or less where it was supposed to.

  An ugly seam went right up the middle of my front. “Is this right?” I asked. “Maybe I have them on backward.” I sure as fuck hoped not. I didn’t want to struggle into them all over again.

  I sucked in my belly, but a little flab still lapped over the waistband. This was what it felt like to be a sausage.

  Jeff hooked his fingers into the elastic, stretched it, then resettled it higher, trapping the belly fat underneath, where the pressure of the control top held it flat. The seam still looked like ass, though.

  “I don’t think I’ve ever been with a girl while she was wearing pantyhose,” I said.

  “No?”

  “I’d remember having to wrestle the fucking things off her.” Flesh springing free like sponge cake. “Kris wore leggings mostly under her skirts. Or just went bare-legged. Now I see why.”

  Jeff was pulling my slip back down, smoothing it free where it clung to the hose. “I kinda think they’re sexy.”

  “Do I look like a woman yet?” I said.

  “Eighty percent more than you did when we headed over here.”

  “What’s next?”

  He lifted the dress from the bed by its sleeves. Its skirt swayed. The tucks and pleats in the bodice gave it a shape I didn’t have. It also looked a whole lot more delicate than I was. I knew it more or less fit—I’d pulled it on over my jeans in a men’s fitting room. And Jeff had walked right into that scared space, rapping on the door, saying, “Let’s see.” The bulk of my belt under the dress had made it sit funny, and chest hair spilled through the vee. I’d looked like a circus act. But I’d run my hands over the fabric, feeling the way the skirt moved under my fingers, and I kind of liked it. Not, you know, in a perv way. And when I’d opened the door to show Jeff, self-conscious as hell, he’d adjusted a sleeve, had me turn around, and said, “Yeah, that’s the one.”

  Now I was going to be trying it on without the chest hair, with a slip to smooth its curves, and jellyfish tits to give it even more.

  “Arms up,” Jeff said with the dress gathered in his hands. Since elbows had been my undoing in the fitting room—Jeff had had to get me out of it—I was more than okay with letting him slide it down my arms, tug the bodice into place, pull the skirt loose until it fell just the way it shoul
d around my legs. He went behind me to zip me in. I felt like I should hold up my hair in the back, like they do in the movies, but I didn’t have any hair to do that with yet.

  As he drew the zipper up, the dress snugged around my stomach. His knuckle brushed my back. The tag tickled my skin as he flipped it inside the back of the dress.

  Putting my hands flat against my stomach—I don’t think I’ve ever seen my stomach this flat—I looked down at my cleavage, the flowing skirt, my shimmery legs. I felt a little like Cinderella must have felt, transformed by the wave of a wand.

  “Bippety-boppety boo,” I said, smiling.

  A knock came, and the door swung open as we both looked toward it.

  “Well look at you,” Lydia said.

  “I’d like to look at me.”

  “Soon,” Jeff said. “Hair next.” He was saying this to Lydia.

  I looked down at my toes, the fabric of the skirt swishing above them. A plastic bag rustled. Jeff came to stand in front of me, the wig in his hands like some kind of wavy Davy Crockett cap. Lydia’s elbow bumped me from behind, and she said, “Look up.”

  Rolling my eyes upward, I caught a glimpse of what looked like more pantyhose.

  “What’s that?” I asked as she stretched it over my head.

  “A wig cap.” Her fingernails sent shivers over my scalp as she tucked stray bits of hair under it.

  “So that’s what you’re gonna look like in ten years,” Jeff said.

  “I’m hoping I got my hair follicles from my mom’s side of the family. My grandpa still has a full head.”

  “They say that’s how it works.” Lydia tucked in hairs at the nape of my neck. The cap itched a little. I scratched my jaw to quell the urge to scratch my scalp. My face felt like a ten-year-old’s. I rubbed it a bit, marveling.

  Lydia slapped my wrist. “Stop rubbing off your makeup.”

  Jeff held up the wig, perched on tented fingers. It was a mess of curls. Lydia bumped him out of the way and took it from him. She put the front of the wig against my forehead and levered it on. With one hand holding it down, she tugged the back around the base of my skull. Then she adjusted the front until she was happy with where it sat before moving around me, fidgeting with the band.

  By the time she was in my face again, she had moved to futzing with the hair itself. “It looks like this thing’s been sealed in a bag since mod was in fashion. The first time.” She lifted and resettled curls, used her fingernails to fluff them up, smoothed the bangs to one side with the edge of her finger. “This was definitely the right style to go with. It softens your brow.” She stepped back, evaluating, and finally said, “I’m jealous that your ears don’t poke through your hair.” She hooked a lock of her own hair back, tucking it behind one of her sticky-outy ears.

  “Can I look now?” I asked.

  Jeff was definitely looking, checking me out from wig to toe.

  I grasped my skirt on each side and did a circle for him, showing off.

  He took a step or two back, without taking his eyes off me, and dragged the pea coat off the mirror. I didn’t have a line of sight to it yet. I drew in my breath, the layers of clothes pressing against me. He lifted his eyebrows, tilting his head toward the mirror.

  With my first step, the skirt swayed. The dress slid against the smooth slip, the slip slid against the smooth hose. The sound of my motion was a whisper. The skirt was the first thing to come into view, and then there I was.

  Or there she was.

  “What do you think, Charli?” Lydia asked.

  I smoothed my hands over my hips, looked up to my face. Her face.

  Thick black eyelashes blinked when I blinked. The pink tip of a tongue touched a glossy red lip. I smiled.

  The curls itched where they touched my jaw, but I shook my head a little, and they bounced, and I smiled at that too.

  Lydia started playing with the wig, fluffing it up, shaping it around my face with the sides of her fingers. The curls tickled my shoulders.

  “One last thing,” Jeff said, pushing away from the dresser he was leaning on, digging a hand in his pocket.

  “Shoes?” I said, wiggling my toes.

  “Well, those too.”

  I caught a glint just before he stepped behind me, and then the glint winked at me in the mirror as he lowered a thin silver chain with a tiny diamond pendant in front of my face. It tickled my skin, and I reached up and took it between my thumb and finger.

  “Can you get your hair?” he asked.

  “Oh yeah.” I dropped it. Cubic zirconia more likely than diamond, but a nice touch anyway. It felt awkward gathering fake hair behind my neck. I was worried I’d displace the wig in the process.

  In the mirror, my armpits were smooth. The front panel of the dress moved with my breaths. Jeff’s fingers brushed lightly against my nape as he fastened the chain. He ran his fingers around it, toward my throat, settling it just so before putting his hands on my shoulders to look at me in the mirror.

  I let my hair tumble down.

  The necklace glittered just above my cleavage.

  I caught Lydia watching from just past my shoulder, her expression odd.

  “Okay, shoes,” Jeff said, with a squeeze.

  “Shoes,” Lydia said, snapping to. “Try not to break your ankle in these.” She held out the open box, red pumps with ankle straps nestled within. They were a deeper red than the dress, deep enough to not look like stripper shoes. The heels were tall but thick—not chunky, but far from stilettos.

  At least I wouldn’t be leaving divots everywhere I went.

  “Sit down,” Jeff said, drawing one of the shoes out.

  The end of the bed was the only place available. I smoothed the skirt over my thighs as he lifted my foot by the heel and slipped the shoe over my toes. Just like Cinderella again.

  He propped the bottom of the shoe on his thigh so he could use both hands to fasten the thin strap. The strap was a nice touch, and not only because I’d be afraid of walking right out of the shoes if they weren’t attached. My ankle looked daintier with the strap around it. It was surprising, too, how sensitive my ankle was. With every move of my foot, tendons I hadn’t known I had shifted against the strap.

  And with each new addition to my wardrobe, I was feeling more and more...feminine. I looked over Jeff’s head, watching myself in the mirror.

  I really could be a girl. Maybe not Claudia Charriez, but I wouldn’t kick me out of bed.

  I hadn’t had anyone put my shoes on for me since I learned how to do it myself. It was strange how a kind of comforting feeling came back with it. The feeling of being taken care of.

  Jeff’s hand was warm against my heel. The second shoe glided across the silky hose on the sole of my foot. Even propping my foot against his thigh, it was like someone caringly tying my shoe for me as he put the strap through the tiny buckle and pushed it into place.

  “Feel okay?” he asked with his hand around my ankle, his thumb rubbing the hose lightly.

  I kind of didn’t want this part to end.

  He offered his hand—not the guy way of grabbing wrists and yanking. He clasped my fingers and helped me to my feet, putting a hand on my waist to make sure I had my balance.

  “How do I look?” I turned unsteadily on the heels. Gravity and the hundred and fifty pounds pressing down crammed my toes to the front of the shoes. The straps dug into the backs of my ankles. My skirt swished against my legs. The wig tickled my shoulders.

  “I’d do you,” Jeff said.

  “Hell, I’d do you,” Lydia said, “if I hadn’t witnessed your awkward and gross journey through puberty.”

  I’d had a crush on Lydia once. She was in high school when we were in junior high, a senior when we were freshman, and swooping through the periphery of our lives after she headed for college. I don’t remember when I outgrew the crush—probably after seeing too much of her: too many sleepovers where I stood outside their one bathroom pounding on the door, needing to take a shit and she’d bee
n in there an hour, futzing with her hair. Too many boyfriends hanging out with her on the couch. Too many loud dinners at their table. The Martinez household didn’t eat in peace. Simple meals erupted into arguments or laughter, or both. When I first started going over there, I found it hard to relax. I’d had a decade of “Would you pass the rolls, please, Charlie?” and “How did your history test go today, Charlie?” Jeff, on the other hand, had trouble relaxing at our house: “Are they being so quiet because you have a guest?” Jeff’s dad is Argentinian, his mom Scottish. My parents are plain whitebread, my dad with his beige thinning hair and button-up shirts, my mom with her pageboy and practical blouses. For two years, my mother referred to my best friend as “The Martinez Boy.” My parents are okay though. They half-adopted Jeff in their subdued, non-touchy-feely way. They bought towels just for him for when he slept over. I mean, I know from visiting other people’s houses that it’s weird, but we each have our “own” towels, and then the guest towels. No one just grabbed a random towel out of the closet when they needed on. So Jeff getting his own towels was as close to being an honorary family member as you could get. When we graduated high school, they took both of us out to dinner to celebrate. They gave him a Keurig when he moved into his first place, his coffee habit being well known. When I flunked out of college a year later, got a job, and moved into a two-bedroom apartment with him, all my parents gave me were new towels. I guess they’d figured after a year of living on his own, Jeff already had anything we’d actually need, except an extra set of towels.

  “How are the shoes?” Lydia asked. “Too tight?”

  “They’re not Vans, that’s for sure,” I said. I wanted to see them in the mirror, which required taking a few steps. I felt as graceful as a newborn foal and a hundred times more ridiculous. “Is there a trick to walking in these?”

  “Small steps,” she said.