Working (Girl) from Home Pt. 02

Story Info
Patience is a virtue, but Jennie is a sinner.
2.2k words
4.7
20.1k
37
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
meowjennie
meowjennie
293 Followers

A few hours ago, I couldn't have imagined that my penchant for girly clothing would put me in a situation where I would be fucked by my boss over a desk while dressed to the nines like a slutty secretary—replete with a skin-tight pencil skirt, towering Louboutins, and dramatic makeup—and then, with his cum still trickling out of my ass, coerced by my ex-linebacker concierge into what was certainly going to be another rough breeding session. To be fair, I hadn't put up much of a fight either time, but that was because I had no choice...right?

Concerned by this troubling thought, I kept my head down as I resignedly followed a leering Leo into the lobby elevator, my "So Kates" clicking delicately across the floor. The elevator car sagged a little and creaked audibly when Leo stepped into it. He towered over me even in my heels, with thick, rippling muscles visible even through his fitted blue dressed shirt. Some part of my mind idly wondered if his massive size would translate down there.

I was afraid to meet his eyes as I daintily tiptoed onto the cold steel, but he cupped my chin in his calloused hands, and tilted my head up. What I saw was pure, burning lust. He was certain of what he wanted, just as he was certain that I was going to give it to him. While I had dated women in the past, I had never once experienced anything close to this unadulterated desire. It felt like a switch in my brain flipped. I understood what he wanted from me, and even though I had no choice, I still wanted to please him. There was something I craved about having the power to fill such a terrible need.

At this realization, I blushed furiously. What the hell was wrong with me? Breaking free of his grasp, I turned away in silent, burning shame, but I could feel an even stronger heat stoking directly behind me. The elevator doors had hardly closed when I heard the sound of his rough hands rasping against the material of his slacks.

The confident growl in my ear sent shivers down my spine. "I can't wait to breed you."

To my alarm, my little clit, safely tucked away in its black lace prison, gave a twitch in response, but what caused my heart to almost stop was the feeling of the elevator decelerating before it had reached my floor. Someone must be going up to the gym!

I panicked. Should I turn away? It would be weird for someone to be facing away from the elevator door, right? Wouldn't that invite more questions? How convincing would my girl voice be under pressure? Before I could break out of my terrorized stasis, the doors opened, and my heart went from being stuck in my throat to dropping through the floor.

The gorgeous, fit blonde in a pink Lululemon bra and matching high-waisted yoga pants, distractedly swiping on her phone, was Ashley. She was probably going to the gym for her daily cardio and selfie routine. I would occasionally catch a glimpse of her in the building, and knew her name from idle gossip with the other tenants. It wasn't hard finding her profile on Instagram, and like what was certainly a sizeable portion of her 100,000 followers, I had masturbated to it countless times while fantasizing about her juicy, round ass. I was pretty sure she didn't even know my name.

She looked up from her phone as she stepped into the elevator, and noticing me, casually scanned me up and down. It took me a moment to realize that she was evaluating if I would jeopardize her standing as the hottest girl in the room, or elevator as it were. I couldn't believe that she actually thought I was a girl, much less a potential threat!

I self-consciously tucked a few stray strands of hair behind my ears. Surely, my makeup was a mess after the rough fucking I had received at the office, and my hair and outfit disheveled. But my confidence soared when instead of giving a dismissive smirk, Ashley furrowed her perfect brows almost imperceptibly. Ignoring me entirely, she batted her eyes at Leo and smiled coyly.

"Leo, you know the issue I was having with my pipes last week? I think you might need to come take another look later."

I couldn't believe this was actually happening. Was she really trying to let me know that she was fucking Leo, like a bitch marking her territory?

Before I could fully process what was happening, Leo shocked me with his response. "When I have time. I have to help the new 'girl' move in. Get settled."

Ashley's pretty face briefly contorted with rage, before she abruptly turned around without a word and began furiously typing on her phone with both hands, ignoring the both of us. I could faintly hear workout music begin playing through her AirPods. This girl was clearly not used to rejection.

Despite the awkward silence, I couldn't help but stare at the heart-shaped globes of her butt, and the almost imperceptible camel-toe that she no doubt intentionally flaunted with her thin yoga pants. This was the closest I had ever been to Ashley, and I was hyper aware of the pleasant floral fragrance that enveloped her like a cloud.

This stunning goddess had just been thoroughly one-upped by...me? Did Leo really want me so bad that he was willing to piss off this beautiful catch?

I immediately had my answer when I felt him lifting up the back of my skirt. The tightness of the pencil construction was a slight obstacle but in moments I felt the smooth cotton slide over my taut ass cheeks, exposing the slip of lace between them and the straps of my garter belt. What the fuck? Couldn't he wait like two minutes?

Trying not to cause a commotion that could cause Ashley to turn around, I tried to slap away his hand with my small, manicured one, but he easily caught my wrist and held my arm behind my back. I could feel him move the material of my thong to one side, exposing my puckered sphincter. It was then that I realized that I was completely at the mercy of the powerful, masculine man behind me. He would do whatever he wanted to me, and I wouldn't be able to stop him. But surely, with Ashley standing right there, there's no way he w-

It felt like someone was trying to shove an aluminum can up my ass. I barely had to presence of mind to stop myself from screaming in what could have been either pain or pleasure. My boss's cum, which I had been unconsciously holding inside me, gushed out as I went limp in shock at the sudden invasion of my body. The thick fluid seemed to provide the lubrication that Leo needed, as I both heard and felt the bulbous head of his cock pop into my sphincter. Had I not been thoroughly fucked by my boss not even an hour ago, there's no way Leo's massive dick would have gone inside me that easily. I had only ever taken one other cock, but even I could tell that this beast was on an entirely different level in terms of size.

I had always fantasized about a threesome with Ashley, but not like this!

Leo grunted as he began working his hips, and I could feel the bulging veins of his thick cock grind against the walls of what I was beginning to think of as my "pussy," already warmed up and stretched out for the first time by my boss. It no longer hurt. Instead, waves of pleasure undulated through my body as Leo pumped in and out of me, turning me into a girl, his girl. My eyes rolled back in my head as I lost myself in the pleasure of being completely dominated by this handsome, powerful man. I barely noticed and certainly didn't care as Ashley exited the elevator in a huff without looking back.

As the elevator resumed its upward journey, Leo grabbed my hips and eased me forward before slamming the emergency stop button. It was clear he couldn't wait until reaching my apartment, and neither could I.

Without the fear of discovery or interruption, I put both hands against the elevator doors and began meeting Leo's thrusts with my own, working his shaft further and further into me. It felt like there was a switch buried deep inside of me that I needed his cock to flip, one that would permanently turn me into a girl. The rhythmic slapping of his hips against my ass cheeks was punctuated with an occasional feral growl from him and a small, girlish moan from me.

"I dreamt about fucking you when I saw you this morning." He panted. "You're even tighter than I imagined."

Lost in feminine pleasure, I murmured, "Am I tighter than Ashley?"

"Oh for sure, forget that bitch. I'm gonna breed you every fucking day from now on."

I smiled through a haze of ecstasy, realizing that I had never truly wanted to fuck Ashley, I had just wanted to be her, a perfect, unattainable pinnacle of femininity. Little did I know, it had always been within reach. I could feel all the desire, validation, and power that came from being a beautiful woman, if I just submitted to real men like Luke and Leo. It was that easy.

Had my mind not been completely blank from being fucked silly, I would have thought it odd that I had no urge to touch my clit. When playing with toys at home, I always had to use my hands to get off. But now, I could feel each thrust of Leo's cock slowly building me towards an inevitable climax.

Abruptly, Leo pulled his thick meat entirely out of my ass, and I whimpered at the sense of utter emptiness.

But he quickly flipped me around, then shocked me by effortlessly picking me up and slamming me against the elevator doors. I hadn't been picked up by anyone since I was a child! But I shouldn't have been shocked at how easily Leo did it, with his incredible, Herculean physique. I felt so small and feminine in his embrace, and instinctively wrapped my legs tightly around his waist to provide him with better access to what he wanted.

He then shocked me a second time by pressing his warm lips against mine. I closed my eyes and melted into his kiss as our tongues danced. My senses were firing on all cylinders and I could smell the pleasant scent of his aftershave mingling with his natural, masculine musk. The cold steel of the elevator walls against my back did nothing to temper the ardor of our passionate lovemaking.

Leo was truly an athlete, because without looking or even using his hands, he perfectly lined up his cock with my pussy, and I screamed with pleasure as he buried his cock to the hilt with a single thrust. Fully impaled by his masculinity, it felt like the only thing that was keeping me up in the air was his giant, virile cock.

That was the last straw; my girl switch flipped. Cum gushed out of my limp clit as a roiling anal orgasm overwhelmed my senses. I felt my toes curl and my ruby fingernails carving deep furrows into Leo's back as wave upon wave of pure ecstasy crashed upon my body. The orgasm must have also caused me to involuntarily clench my sphincter, because before long I heard Leo groan loudly and my thoroughly used pussy was once again completely filled with another man's hot seed.

Leo broke from our kiss and nuzzled my neck, panting. Our sweaty bodies entwined, both of us having climaxed, and his resplendent masculinity buried deep inside me, I never wanted the moment to end. But gradually, I felt his monster cock soften and begin sliding out of my worn pussy. Inexplicably, tears began forming in the corners of my eyes and I choked back a sob.

Leo gently set me down, his concern apparent. "Hey...hey you, what's wrong? I thought you enjoyed it too...?"

Nervously, I pulled down my skirt and tried to fix myself up, and in a soft voice that was somehow more feminine than it had ever been, I haltingly asked if he wanted to cuddle.

At this, he chuckled. "Sorry, babe. You know I'm on the clock." He fished out a set of keys from his pockets, and after inserting one into the elevator panel, we resumed our journey towards my unit. I bit my lip and looked down.

"But I'll tell you what. Why don't I come by after my shift?"

I shyly threaded a slim arm through his, and clutching his bulging, rock-solid bicep, nodded silently. But his next words caused my still-pounding heart to skip a beat.

"Make sure you look nice, cuz I'll be bringing a friend."

THE END...?

Jennie's note: Hello, dear reader, and thank you for finishing my story. I hope you found it hot, as I certainly did when I wrote it! I look forward to your questions, suggestions, critiques, and comments, as they all encourage me to keep writing!


meowjennie
meowjennie
293 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymous10 months ago

very much enjoyed the story … and the prospect of adding his friend - well that will certainly take me over the top .. in your continuation (which I very much hope that there will be) make sure to continue with kissing her luscious lipstick lips - including tongue play, sucking his delicious oversized dick, and attention he gives to her sensitive sissy pussy .. please make the continuation happen

Mukul10Mukul10over 1 year ago

Awesome story hope you make more

Sissylisa221Sissylisa221about 3 years ago

You evil, evil woman!!! Can't wait for the next installment/ chapter, this is literotica just wish the stories were a little longer but you would be a good suspense author, you've left me hanging on the edge with all of your stories ((WANTING MORE, MORE, MORE))

biazmbiazmover 3 years ago

Wow -this story just keeps getting hotter and hotter! I can't wait to again read more. What an exceptional author!

AnonymousAnonymousover 3 years ago
More please!

So hot, I came well before getting to the end but had to finish reading.

Show More
Share this Story

Similar Stories

Working (Girl) from Home Pt. 01 Working from home means dolling up! What could go wrong...?in Transgender & Crossdressers
Halloween: A Pussycat's Tail A shy crossdresser discovers herself on Halloween.in Transgender & Crossdressers
A Prom(ise) Fulfilled A closet crossdresser's stepbrother needs a prom date...in Transgender & Crossdressers
Working the Holidays Classic Christmas tale of blackmail and forced feminization.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
More Stories