Working (Girl) from Home Pt. 01

I woke up to the whimsical chiming of my phone alarm. It was Monday morning, and under normal circumstances, Monday mornings were the absolute worst. But the times were far from normal, and in response to the spread of COVID-19, my boss had implemented a mandatory work-from-home policy. While my coworkers bemoaned the lack of office socialization, I was secretly elated because it gave me the unique opportunity to indulge in my deepest secret on a daily basis.

I unplugged my phone from the charging cord and quickly scanned my notifications. Dismissing a few news items, I saw the reminder for the weekly "team update" conference call at 10:00 a.m., where my boss, Luke, spent an hour summarizing what had happened the previous week. During these rather pointless calls, I suspected that I wasn't the only one who dialed in, muted myself, and proceeded to do other stuff on my computer.

That was two hours away, which gave me barely enough time to get ready. Though two hours might seem like an excessive amount of time for a guy, I wasn't really getting ready as a guy. Instead, since I started working from home half a year ago, away from prying eyes and the inconveniences of social obligations, I had been living full-time as a girl.

I had always felt the urge to dress like a girl for as long as I could remember, but it wasn't until recently that I had the opportunity to fully immerse myself in that desire. My hair had grown, but not nearly as much as my collection of clothes, makeup, accessories, and of course, shoes.

As a low level analyst, my sole responsibility was to pore over the spreadsheets assigned to me, and I had no obligations to video conference or even really communicate with my coworkers aside from sending in results to my boss. I reasoned that if I was going to be spending eight silent hours a day in my apartment working, I might as well be dressed the way I had always secretly wanted to.

Stretching languorously, I curled my toes—painted a bold ruby red—threw off my sheets, and skipped lightly to the bathroom to begin the ritual that was the highlight of my day. Passing by the bathroom mirror, I caught a glimpse of a slim figure with shoulder length auburn hair and a perky butt emphasized by gray Calvin Klein bikini panties. There were no breasts under the matching sports bra, yet the person was decidedly feminine, moving with a practiced sway of the hips.

I tugged my panties down, sat on the toilet, and relieved myself while idly browsing my Instagram feed for inspiration for my "look of the day." One of my favorite idols had posted a teaser for her next single, and the concept seemed to be "sexy secretary" with a skintight pencil skirt, dramatic smoky eyes, blood red lips, and of course, dangerously high stilettos. It had already garnered over a million "likes."

I felt a rush of conflicting emotions, equal parts lust and jealousy. I wanted to ravish her perfect femininity almost as much as I wanted to be her, to command the sexuality, adoration, and power she had over her fans. With a wipe and a flush, I decided that I'd been properly inspired, and that I'd try to pull off a similar "secretary" look. Even though I was working from home, I didn't always dress in office-appropriate attire. The day before I had just been in a Lululemon yoga outfit, with my hair in a messy bun.

Throwing open the doors to my closet, I felt the familiar anticipatory tingling in my tummy that was always there before I transformed into "Jennie." I had moved all of my boy clothes to the top shelves as I hadn't been wearing them at all, but the closet was still packed end-to-end with hangers of girly clothes. With clothing retailers not doing so hot during the pandemic, there was a never-ending stream of sales online, and their newsletters always managed to entice me into spending more money than I should.

I always planned my outfits from the inside out, and though I loved how comfortable and cute my CK undies were, they just didn't fit into an outfit like the one I had in mind, so I changed into a Victoria's Secret black lace pushup bra. Already, I was getting kind of excited down there, so I quickly tucked my boy parts in between my legs and pulled up the matching lace thong to keep everything in place. I fished around in my lingerie cubby until I found the third piece to the set: a garter belt with four straps that somehow stayed up on my boyish hips. Taking my time to avoid any runs, I rolled a pair of sheer black stockings up my shaved legs and clipped them into place.

Next was the outfit itself, Brushing aside several hangers of skimpy club dresses, plaid skirts, and denim short-shorts, I found what I was looking for: a delicate, sheer white blouse with a black self-tie around the neck that I had purchased online recently, but hadn't worn yet. I slipped into it, reveling in the softness of the sheer material and how it rustled against my bra. I fumbled with the buttons a bit, unaccustomed to them being on the left side, then slid into a high-waisted calf-length leather pencil skirt, almost decent if not for a back slit that went almost to my butt. Zipping it up, I wiggled a little and loved how the material moved with my body and emphasized my legs. Finally came the pièce de résistance: a pair of Louboutin "So Kates" that I had found for a steal on eBay and that I could just barely squeeze into. The moment I slipped into the stilettos, I felt like Cinderella with her glass slipper: utterly transformed.

"Jennie" took over, and I strutted back to the bathroom, heels clicking loudly against the floorboards. I naturally had very little facial and body hair to begin with, but I kept myself completely smooth at all times through both razors and creams, except for a cute little patch above my cock. After washing my face and applying a few skincare products, I began the long process of creating a feminine illusion through the power of makeup. Fortunately, over the months I had gotten down a look that I was satisfied with, and daily application meant that I had gotten in plenty of practice.

First, a sheer layer of foundation, quickly followed by concealer over a few problem spots. Then, contouring and highlighting to deemphasize my brow ridge and soften the jawline, and to make my nose seem thinner and more pointed. Blush in a deep red, then a combination of brow gel and pencil for a delicate, natural arch. I opted for a dark red eyeshadow, a bold cat-eye eyeliner, luscious false lashes, and a generous application of mascara. Next, an application of YSL lipstick in a bold red, and a lip plumping gel for a cute pout. Finally, I popped in a pair of gray circle lenses to make my pupils large and doll-like.

With my face complete, I put my hair back in a loose ponytail, spritzed a little Chanel No. 5 onto my neck, put in a pair of dangly silver earrings, quickly slid on a thin silver chain bracelet and a few rings, and made my way to the floor length mirror to check out my handiwork, buzzing with anticipation.

A lithe porcelain doll stared back at me, her youthful, innocent features in stark contrast to her provocative makeup, towering heels, and lingerie tastefully hinted at through her blouse. Though she barely had any hips or breasts, her narrow shoulders, above-average height, and thin limbs cried "model" and not "male."

Some of my best work yet, I thought to myself, as I struck a few runway poses. I felt an uncomfortable tightness under my tight skirt as the gorgeous woman in the mirror pouted and winked back at me. I fantasized about fucking the woman in the mirror, and started taking selfies like I always did. But I must have lost myself in the pleasure of indulging in my femininity, because before I knew it, it was already 15 minutes past ten. Shit!

I teetered my way to my computer and opened the Zoom meeting invitation link, hurriedly clicking through all the confirmation prompts. A cheerful chime confirmed that I had joined the meeting's audio, even though my browser was still loading the video component, which was either going to be the solemn face of my boss or one of the PowerPoint presentations he occasionally put together for these meetings. Employees like me were always audio-only as we didn't present or talk, even though attendance was mandatory, which is why everyone except Luke resented these meetings.

The audio channel was silent, however, and I breathed a sigh of relief. My boss, Luke, must have also been running late if the meeting hadn't started yet. Usually he'd be well into one of his monologues by this point, and I'd probably be browsing forever21.com, or perhaps, working on a story on Literotica.

As the meeting's video finished loading, I saw Luke's face, as expected, but his expression was one of utter shock. Then, to my abject horror, I saw my own feminine visage in a window on the bottom right. My appearance must have caused him to be at an uncharacteristic loss for words, as his classically handsome, all-American features were frozen in surprise.

Time seemed to stop entirely. I could hear my heart pounding in my ears, and I resisted the urge to vomit. Some small part of my brain reasoned that in my rush to join the meeting, I must have accidentally turned on my webcam. This was it. I was ruined. Everyone knew I secretly dressed like a girl. Was I going to be fired? Was I going to jail?

In a daze, I turned off my webcam even though Luke's expression told me it was way too late.

"Um, excuse me." Luke cleared his throat. "As I was saying, the investors expect a more aggressive strategy this quarter..."

I scanned the chat box: it was empty, and nobody was typing. No accusations of me being a pervert. Per usual, it seemed like nobody even had the meeting window maximized. Was it actually possible that nobody actually saw me in that brief moment, besides for Luke?

I could barely swallow the dry lump in my throat as I sat there contemplating my options. Should I quit? It would be difficult if not impossible to secure a new job during record-level unemployment... Pretend that it wasn't me in front of the camera? No, even though I looked decidedly feminine with the long hair and makeup, I also looked decidedly like me. Luke wasn't stupid.

I lost myself in a cycle of desperate thoughts, and the meeting must have concluded at some point unbeknownst to me because the meeting window closed.

"Please rate your conference call experience!" suggested the prompt. I clicked "one star."

Immediately, my phone started ringing, and felt my stomach sink to a place I didn't think it was possible. It was, of course, Luke. Something compelled me to pick up, even as my rouged cheeks burned an even deeper crimson with shame.

"H-hello?" I squeaked.

"Hello, who's speaking?" Luke demanded.

"Huh?"

"You're the new girl on my team, right? What's your name again?"

I was baffled. From his shocked expression earlier he clearly knew that it had been me on the call. Was he asking for my girl name?

"I'm Jennie," I said softly, unconsciously using the feminine voice I had been practicing every day.

"Right, Jennie. Well, as you know, new employees need to go through orientation on-site. As you're aware, the office is closed, but I'll make a personal exception for you. I expect to see you there in thirty minutes."

"Orientation? B-but I've already gone through orientation already?"

A long, uncomfortable pause. "I don't believe you've gone through secretary orientation, have you, 'Jennie?'"

"N-no...sir." I said meekly.

"Good. Then I expect that you'll be dressed...appropriately." He hung up.

I fell back in my chair with a sob. Luke was playing some twisted little game, and I had no doubt that he was ready to humiliate or fire me. But what choice did I really have? I had no desire for Luke to tell my coworker about my little hobby, and even less desire to move out of town. I could do nothing but play along.

For me, who had never even left the house dressed as a girl, just the thought of heading over to the office en femme was terrifying, much less what would happen once I got there. But I slowly realized that as masks were becoming normalized, my biggest fear—being recognized by someone I knew—was alleviated.

My brain on autopilot, I grabbed my quilted crossbody Chanel clutch, my keys, and put on a black cotton mask that covered most of my face except for my large, inviting eyes.

I stepped into the apartment hallway in my Louboutins for the first time, and my heart leapt into my throat in a mixture of elation and pure terror as the door automatically locked behind me with a loud click. I could hear faint voices coming from one neighbor's unit, and TV sounds from another, but the hallway was empty.

I made sure my mask was secure before quickly tiptoed my way to the elevator, praying that I wouldn't run into any nosy neighbors wondering what a provocatively dressed girl they had never seen before was doing on their floor. My prayers were answered, because I didn't, and even luckier, the elevator didn't stop all the way down to the lobby.

As the elevator opened, and I took a deep breath to gather myself and began powerwalking to the lobby doors. Months of practice in my apartment had me accustomed to walking in my sky-high stilettos, and they clicked in a distinctly feminine rhythm as I made my way across the marbled floor. Just as I pressed a dainty hand against the handle, a voice rang out from behind me.

"Excuse me, miss. Are you new here?"

Like a deer in headlights, I froze, before slowly turning around in dread. It was Leo, our building's concierge. Leo was 6'6", a former second-string college football player. Unlike a lot of ex-athletes, he still kept himself in great shape. Our building wasn't that large, had low turnover, and he knew all the tenants on a first name basis. It seemed obvious in hindsight that he would find me out of place, especially given how I was dressed.

"I-I'm just visiting." I stammered, this time consciously using my feminine voice.

"Oh, I see. Lucky guy." Leo grinned slyly.

I suddenly had an inkling of what attractive girls had to put up with: the constant pretexts of conversation to get your attention, the not-so-subtle propositions in every interaction.

I rolled my eyes and turned away without saying anything, but could feel the heat of his gaze on my perky, skirt-clad ass as I exited the building. I shivered from the intensity, but couldn't say for sure why

.

The streets were mostly empty, and I managed to hail a cab to the office without incident, the disinterested cabbie too focused on his radio talk show to even glance at the vision of femininity in his back seat.

When we arrived, I daintily swung my long, stockinged legs out the cab door, and Luke appeared out of nowhere dressed in his trademark gray suit, crisp white shirt, and skinny, navy blue tie. Without a word, he gallantly extended his hand to help me up.

I had never felt so humiliated before in my life, dressed like the office slut in front of my boss of five years. But I also knew that given the state of my nerves, I had a huge chance of falling on my ass if I tried to get up without assistance. Reluctantly, I allowed his large, rugged hand to engulf my delicate, French-manicured one as he helped me out of the cab. Even with him steadying me, I still stumbled. Note to self: walking in heels on smooth floorboards was not the same as walking in heels on uneven pavement.

Luke caught me, and for a moment, I felt so tiny and feminine in his strong arms. It felt kind of...nice. I quickly dismissed the thought from my head. I liked women. I liked women which is why I wanted to be like them...right?

My boss slowly let go of me, and casually adjusted his tie as I stared up at him fearfully. "Shall we begin?" he gestured at the office building.

I couldn't scrutinize his expression underneath the mask. I had no idea what he was playing at but what choice did I really have? Wordlessly, I followed him as he made his way through the almost-empty building to our company's floor. As expected, it was entirely empty and dark, other than the light in Luke's office. He was a chronic workaholic and it was well known that he chose to continue to work in the office to avoid the distractions of his wife and kids at home.

I shuffled my feet awkwardly, and the click of my heels boomed in the hollow silence of the office.

"A secretary must always be presentable. Take off your mask." Luke ordered abruptly.

I didn't know what else to do but to comply, making sure not to smear my makeup. I was too terrified to look at him, and instead stared down at my dainty heels while absently tucking a few stray strands of hair behind my ear.

"Look at me."

I slowly looked up with wide, terrified eyes. His steely blue gaze now drilled straight through me.

"You've put me in a difficult position, Jennie. As you're well aware, your employment contract authorizes us to track your browsing history on company devices, and I've taken the liberty of reviewing yours. Shopping at Forever 21 on company time? Reading smut on Literotica? I could have you fired right now."

I thought it wiser not to tell him that I had been reading AND writing smut on Literotica.

"Please, I can explain-" He held up a finger, cutting me off.

"But given your five years of loyal, if somewhat mediocre, service to the company, I've decided to be lenient and only demote you..."

A demotion? But I was still at the same entry-level position that I was hired at. The ladder didn't go lower. Unless he meant...

"...to my personal secretary, effective immediately."

The position had been vacant since before we started working from home, when Christina, a blonde almost as gorgeous as she was airheaded, had been caught trying to expense her bikini wax as "office maintenance."

"You are relieved of all of your former responsibilities, and instead will be in charge of making sure that all of my needs are met."

Deep down, I must have suspected what Luke truly wanted from me even before coming to the office, but it was confirmed when he gently cupped my chin with one hand and began stroking the front of his tailored suit pants with the other.

"All...of my needs, do you understand, Jennie?"

At this, my body betrayed me. I felt a familiar fullness growing under my lace thong. Oh fuck, was I getting an erection under my skirt? I couldn't actually want this...could I?

Luke leered at the small tent forming under my pencil skirt. "It seems like you do."

This was beyond humiliating—I was actually getting aroused at being sexually blackmailed by my boss! More out of a desire to hide my growing, unfeminine, bulge than anything, I clamped my legs together and sat down on my calves, bringing Luke's groin to eye level.

But he interpreted it as enthusiasm and I didn't blame him: as a large, powerful, and confident man, he was often the topic of my female coworkers' watercooler talk. But to actually...do sexual stuff with him? I never had any desire for men, but there was something about the situation that compelled me to keep playing along. Submitting to the will of someone masculine, powerful, and in control was just so much easier than the uncertainty of trying to decide for myself.

Like many crossdressers, I had ended up getting a dildo to experiment with. What started out as a few tentative licks eventually developed into a habit of sloppy deepthroating before stuffing my tight little asshole until I inevitably squirted all over myself. I had never seriously considered swapping silicone for the real thing, but now it seemed like either I gave Luke what he wanted, or I'd be socially and professionally ruined forever. I didn't even have a choice, really.

It was like a portion of my brain just shut off, and it was someone else who eagerly unzipped Luke's fly to pull out a massive, veiny penis, only half-erect but already about six inches long. It was someone else who literally started salivating at the sight, and someone else who was sensually licking the tip of Luke's cock with quick, cat-like motions of her tongue.