Working (Girl) from Home Pt. 01

"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 rod 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 manhood deeper and deeper into my ass.

"Oh fuck, sir, I love how your big cock fucks me." I gasped 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 a prostate orgasm. But every thrust of Luke's thick cock hit my girl switch in the exact right place, and I could feel a wave of heat building up in what was really my "pussy." The searing sensation 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 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 hope you found it as hot as I did when I wrote it! I look forward to your questions, suggestions, critiques, and comments, as they all encourage me to keep writing!