Working (Girl) From Home free porn video

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 45 minutes summarizing what had happened the previous week. 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 just 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 and away from prying eyes and the inconveniences of social obligations, I had been living full-time as a girl. Though I had felt the urge to dress like a girl for as long as I could remember, 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 my 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 pi?ce de r?sistance: 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 no 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 my god, 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 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 powerful and in control was just so much easier. 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. "Good girl, you know what to do." Luke said, as he grabbed my ponytail with one hand. I instinctively began stroking his shaft with one dainty hand while playing with his smooth balls with the other, like I had often seen in porn. Except instead of being on the receiving end like I had always fantasized, I was now the one giving pleasure. Luke grunted and pressed my head firmly towards himself, forcing me to take more of him into my mouth. I wrapped my blood red lips tightly around his cock and inhaled deeply, the musky, sweaty scent of his masculinity causing me to moan like a bitch in heat. I could feel my now full erection straining against the constricting material of my thong and tight skirt. I began slowly bobbing my head on my boss's shaft, earrings tinkling softly. He groaned in pleasure, and the hand on my ponytail held my head in place as he began pumping his hips. The sensation of a thick cock sliding in and out of my mouth was completely foreign to me, but I fucking loved it, and focused on maintaining a nice seal with my lips while keeping my teeth out of the way. I could tell that my efforts were paying off as his moans increased in volume and frequency. I finally mustered up the courage to look up and make eye contact with him--because I knew he'd like it. Sure enough, our eyes met, and he smiled down at me, almost with affection. "Jennie, you're such a good girl. As you won't be attending our weekly conferences anymore, I can't wait to have you under the desk sucking my cock instead." He chuckled. "Well, you're technically still attending, I suppose." Instead of humiliation, I felt a flush of pride at this. This attractive, desirable man wanted me with such intensity, that it made me feel attractive and desirable by proxy. It completely validated the thousands of hours I had invested in makeup tutorials and practicing my feminine mannerisms and voice. Even though he was married, Luke could have any girl in the office that he wanted, but he wanted me. I lost myself in the pleasure of noisy, sloppy, cocksucking as Luke enthusiastically fucked my face, and I absently noticed that my lipstick had left a neat ruby ring about halfway down his fully engorged cock, now a magnificent ten inches. His cockhead popped out of my mouth audibly as I paused, panting, to catch my breath. I caught my reflection in the polished sides of a nearby desk--to the casual observer, a slim doe-eyed girl with flawless makeup dressed like every red-blooded man's wet dream. A well-put-together and classy girl...if you overlooked the slightly smudged lipstick...and the thick cock she was holding in one hand...and the unsightly tent in her skirt. Luke then bent down, put his hands under my arms, and effortlessly lifted me up onto the desk, sending pens and papers scattering. I giggled at how girlish it felt to be manhandled like that, right as Luke shocked me by pressing his warm lips against mine. I felt myself responding involuntarily, clasping my arms together behind his neck and closing my eyes, allowing his probing tongue to invade my mouth. He tasted faintly of coffee. As we made out passionately, his hands roamed down to my legs and began massaging my thighs while hiking up my tight pencil skirt. I knew what he wanted, and I wanted nothing more than to give it to him. Pulling away from him, I looked directly at him with wide, doe-like eyes and said coyly in my best girl voice, "Please, sir, I'll do anything to keep my job. Anything." He chuckled and lightly pushed me onto my back, before putting his arms under my knees and pulling my hips toward his. I could feel his firm erection pressing against the thin material of my lace thong. "Cute panties," Luke said, before pulling them to one side and spitting onto his cock. As he rubbed saliva all over his shaft and moved it into position, I craned my neck up so I could see the moment that he entered me and made me his girl. I bit my lip as he slowly pressed the wet, spongy tip of his cock against my anus. I instinctively pulled my perky ass cheeks apart to allow him better access, even as I "pushed" with my sphincter. The pressure increased, uncomfortably, and I grew worried that he was too big for me. But then all of a sudden, his cockhead slipped past my sphincter with a pop, and I felt him inside me for the first time. I gave an involuntary girly shriek of pleasure. It was nothing like my toys at home! The pulsating heat, the fullness, the simultaneous firmness and softness. What I had been missing out on! This was pure ecstasy, and I knew there was no turning back for me from here. I was well and truly a girl now, Luke's girl. "You're so tight, baby." Luke moaned. I watched, enraptured, as more of his veiny cock disappeared inside my tight hole. Luke leaned forward to kiss me again, and I clung onto his muscular neck as I eagerly responded in kind. His stubble felt rough against my soft skin as I breathed in the pleasant earthy tones of his cologne. We moaned into each other's mouths as he began pumping his hips faster and faster, each thrust forcing his cock deeper and deeper into my ass. "Oh my god, I love how your big cock fucks me." I said without thinking. It was apparent that I had fully embraced my new identity as Luke's secretary and fuck toy. Experimenting at home, I had occasionally come close but never actually achieved an orgasm from my butt. But every thrust of Luke's thick cock hit my prostate in the exact right place, and I could feel a wave of heat building up in what was really my "pussy." The heat spread rapidly, radiating all the way to the extremities of my toes and scalp. I wrapped my stockinged legs against Luke's muscular hips and began thrusting back, desperately wanting some kind of release, and our sweaty bodies moved in sync in a choreography as old as time. "Fuck, fuck, fuck, oh my god, fuck, I'm gonna cum!" Someone screamed. It took a moment to realize that someone was me. The unbearable heat in my groin exploded in a dizzying release of sheer pleasure, and trapped beneath the black lace thong, my limp "clit" was uncontrollably dribbling cum all over myself. At that exact moment, Luke grunted loudly right and I felt his cock spasm violently. A molten stream of his semen shot deep into my hole, sealing my fate as his little office whore. He collapsed on top of me, panting loudly. The girly orgasm that wracked my body was like nothing I had ever experienced before, and my eyes rolled back in my head as I twitched in pleasure for what felt like an eternity. Finally, Luke pulled his thick cock out of my well-fucked ass, leaving me with an indescribably empty feeling. I whimpered, not-so-subtly indicating that I wanted him back inside me, but he was spent and already putting his monster back into his pants. "I expect you back here tomorrow at 8:00 a.m., dressed appropriately." Luke said. "You'll be bringing me my morning triple shot espresso." I nodded eagerly--I was addicted to his cock and could think of nothing else. He pulled out a fat money clip from his pocket and peeled off ten bills, handing them to me. I was somewhat shocked to realize that they were hundreds. "For the coffee. Buy yourself something nice with the rest of it." Was he...paying me? Like some kind of an escort? I briefly thought about turning it down, because it cheapened what had just transpired between us, but ultimately decided that beggars couldn't be choosers, especially when he could have me fired on whim. Besides, it felt nice to be appreciated. Taking the bills, I smiled as I stuffed them into the empty cups of my push-up bra. "That's so generous of you, sir. Thank you so much." "Your orientation is now over. You're dismissed for the day." Luke said, already turning away from me and heading toward his office. "I have work to do." I was admittedly a little heartbroken at how quickly he had become all business again. I thought that I had felt something between us when he first kissed me. Maybe I had just imagined it...? I tucked my sticky, limp, clit away and pulled up my thong, hoping to keep Luke's semen inside me as long as possible. It was the least I could do after he bred me. The idea was so naughty and perverted that I just had to do it, even though his cum would trickle out of my ass whenever I forgot to focus on clenching my sphincter. Pulling a compact mirror out of my clutch, I dabbed at my smudged lipstick until it looked presentable, before hiking down my skirt and carefully standing up. I wobbled, weak in the knees after Luke's thorough breeding, but managed to steady myself. Luke was already back in his office, door closed, and I could hear the sounds of typing. I made my way back to the street, my usual confident catwalk now slightly bowlegged, and was surprisingly able to hail a cab and make it back to the lobby of my building without any incident. The cabbie barely reacted when his beautiful passenger handed him a $100 dollar bill for a $15 dollar fare. Maybe he was used to gorgeous women having this kind of cash to throw around. As I stumbled through the lobby doors of my building, two things happened. First, I saw Leo's eyes light up at the return of the gorgeous "visitor." Second, I remembered that after the life-changing events at the office, I had forgotten to put my facemask back on. "Well, well, well." Leo's eyes flashed first with recognition, then calculation. "It seems like you're visiting a bit longer than you expected. Apartment 803, right?" Upon mentioning my apartment number, there could be no doubt that he knew my identity, and that I wasn't really the attractive office "girl" I was pretending to be. "You just received a 'large package.' I'll bring it up for you," Leo leered. I gulped, knowing I had no choice but to agree unless I wanted everyone in the building to know about my little hobby. Head down in resignation, I wordlessly headed for the elevator as Leo hopped out of his chair. Whistling a jaunty tune, he slapped my perky butt fondly, making it crystal clear what the 'large package' he was bringing up was. Just a few hours ago, I had been certain I was straight, but now even as my boss's cum was trickling down my thighs, another man was getting ready to fuck my brains out. And glancing out of the corner of my eye at Leo's impressive physique, I knew I was looking forward to it. THE END...? Jennie's Note: Hello, dear reader, and thank you for finishing my story. I look forward to your comments, critiques, and suggestions, as they all encourage me to keep writing! You can find more of my silly musings at http://jenniemeow.wordpress.com