by D. L. Savage
As I closed the door behind me, I caught a glimpse of myself in the mirror: my slim body shown off by my cute summer dress, my black hair a little tousled, my plump lips still glossy with cum and my eyes sparkling with naughty glee.
Alex was right. I was hot.
The following morning, I woke super early and took a long time getting ready – choosing my outfit and working super hard on my makeup – making sure I looked just perfect. After my naughty, slutty weekend, I could feel myself growing in confidence as Penny – and what’s more, I even felt excited to see Mistress Cartwright again. To show off all the smart, sexy clothes I’d bought on the company credit card, not to mention how much I’d changed and grown as a woman already.
As I headed out of the door, a part of me hoped to bump into Alex again. I still couldn’t quite believe what had happened between us – or just how easy and natural it had all been. I could still remember the delicious feel of his cock in my mouth, and the way my own body had responded.
But it seemed like he was still in his room and I had no time to waste. A quick glance at the clock told me that if I didn’t hurry, I’d be late – and the last thing I wanted to do was annoy my strict and cruel Mistress ...
* * *
“Hey! Looking good!” Becky exclaimed, as I entered reception a short while later.
“Thanks,” I grinned back warmly. “I couldn’t have done it without you.”
“Oh, Miss Cartwright said she wants to see you in her office the moment you arrive,” Becky replied with a strange expression. “And Penny?” she added, her voice dropping to barely a whisper now. “I’d better warn you, she sounded pretty pissed.”
I felt my heart sink. What the hell had I done this time?
“Thanks for the heads up,” I said, pushing my shoulders back and trying to remain calm and collected as I turned and made my way towards that imposing wooden door, the one that led into Mistress Cartwright’s office.
I reached out and knocked, immediately hearing the imposingly stern English accent: “Come in.”
With a final deep breath, I opened the door and stepped into the room.
There she was – sitting at her desk, her jet black hair tied back in a tight, high pony tail, her slim body encased in a figure-hugging pale grey pantsuit and white silk blouse, her eyes and glossy lips narrowed in a venomous expression.
Without thinking, I strode forward to take the empty seat opposite her, but before I could park my ass, she hissed, “Who said you could sit?”
“Sorry, Mistress,” I replied quickly, heart pounding and face flushing with shame.
“Care to explain this?” she continued, holding up a sheaf of papers on her desk.
I stared at her puzzled, wondering what the hell she was talking about.
“I ... I don’t understand, Mistress,” I stammered honestly.
She took the papers and began to read from them, and as she did so, my heart sank even further. “Bra – A Cup, sixty dollars, panties – seven pairs – one hundred and twenty dollars, yoga pants – two pairs, sixty six dollars ...”
“But Mistress,” I began to say, then stopped myself.
“But what, sissy?” she snapped back.
“You told me to buy some suitable clothes,” I offered timidly.
“I told you to buy suitable work attire,” she replied, her voice brimming with anger and disgust. “I said nothing whatsoever about yoga pants, not to mention wigs and makeup.”
“I’m sorry, Mistress,” I said, my eyes starting to brim with tears at the thought that she would make me return it all, all my gorgeous new girly possessions.
“Sorry isn’t good enough, Penny,” Mistress Cartwright snarled back. “Do you have any idea how much you have cost this company with your little spending spree? Well, do you?”
I shook my head, my face burning with shame, too scared to even look at her now, my eyes fixed on the floor in front of my feet.
“Twenty four hundred dollars,” she shot back coldly.
I had to admit, I was shocked. I mean, I knew I’d gone a little overboard, but even so, I had no idea I’d run up such a ginormous bill.
“But don’t worry,” she added, a strange playful tone entering her voice now. “I’ve got a way for you to work off your debt.”
“Really?” I said, my heart flooding with hope.
“But it’s not going to be easy,” she replied with a cruel smile. “In fact it’s going to be very hard work indeed ...”
“This way,” Mistress Cartwright commanded, striding out of her office.
I followed quickly behind, as she led us down the corridor, stopping for a moment at the reception desk.
“Becky,” she said sternly, “I’d like the keys to the basement, please.”
“Sure, sure,” Becky said, shooting me a quick glance, as if to say Is everything okay? And I’m pretty sure that by the look on my face, she could sense I was in deep trouble.
“Here you go, Miss Cartwright,” she added sweetly, handing over a set of large silver keys.
“Now follow me, Penny,” Mistress said, once more striding off – this time towards a grey service door beside the elevators. She took the keys and unlocked it, revealing what looked like a gloomy pitch-black room. I gulped, feeling my nervousness increase. But then she reached in and flicked a switch, and after a moment a fluorescent light flickered on, revealing a dusty, dingy stairwell.
“Well? What are you waiting for?” she growled.
So I took a deep breath and then heading into the stairwell, my heels clicking and echoing on the cold metal steps as I followed the stairs down, down, down ...
* * *
“What is this place, Mistress?” I asked a little while later, my voice echoing around the large dusty room.
“To be honest,” she replied dismissively, “that’s none of your bloody business. But I suppose I’ll tell you anyway. It used to be a storage room, but I’ve had part of it converted for ... other purposes. Mainly as a way of punishing wayward employees, such as yourself.”
At the word punishment I felt a powerful flash of fear – mingled with strange anticipation, too. What devious punishment had she got in store for me this time?
“You see that door in the far corner?” she continued, nodding to a partitioned off grey area in the very corner of the gloomy store room.
I nodded.
“That place is going to be your new home for the rest of today,” she snapped. “Well? Go on then. Get in there at once.”
I did just as she said, walking towards the plain grey door and opening it, stepping into a small cubicle-like room beyond, with crude grey plasterboard walls, the whole chamber not much bigger than a toilet stall. Except unlike a toilet stall, this room was completely and utterly empty. Just walls and a door, with cold cement floor beneath, lit by a single bare light bulb.
“So I suppose you’d like to know your punishment?” Mistress Cartwright announced from the doorway.
“Y-yes, Mistress,” I stammered nervously.
“I’ve decided to make you work off that debt,” she explained in a cold cruel voice. “You see that hole on the wall?”
I looked around me, and sure enough on the right hand wall was an oval shaped hole –about halfway up, at around waist height, just about big enough to put a hand through.
“Well that, you little sissy slut, is a gloryhole,” she announced, like it was the most normal thing in the world. “Today, Penny, you are going to suck twenty four cocks. One for each hundred dollars you wasted. I think that’s a fair enough price for a cheap little slut like you, wouldn’t you agree?”
I nodded, my face burning with shame, but a secret part of me flashing with excitement too. Twenty four cocks?
“So get on your knees and wait,” she hissed.
Again I did just as I was told, submitting to my cruel mistress: lowering myself onto my knees, my heart hammering, as Mistress Cartwright slammed the door, leaving me alone in the bare grey cubicle to wait ...
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I don’t know how long I waited, there on my knees in the bare cubicle. It might have only been a few minutes, but in my state of nervousness and anticipation it felt like an hour. My heart was pounding hard in my chest as I waited on my knees, dressed in my white silk blouse and sensible black skirt, my legs encased in black woolen stockings, and my little sissy cock held snug and tight in a black cotton thong.
Just then, I heard something – the unmistakable sound of the door to the basement opening and closing, and then the heavy tread of shoes on the cement floor, coming this way.
As I waited for this total stranger to reach the cubicle, I wondered who it was. Had Mistress perhaps sent a memo around the office – letting all the guys know that there was a slut in the basement, ready to suck their cocks? Or had she maybe posted the information online somewhere? This could be absolutely anyone, I realized with a shiver ...
I heard the sound of a zip, just at that moment, right by the hole, and then a moment later I watched transfixed as the mystery man pushed his long, semi-hard dick right through the glory hole and into my cubicle.
It flopped meatily before me, pale but with a bulbous purple head – already almost six inches in length and not even fully hard yet. I could just about make out a crop of black fuzz above it, and below a set of big shaved balls. That was as much of this total stranger as I could discern through that oval hole in the cubicle wall.
And now, was I really about to suck his dick?
I reached out nervously, wrapping my slim fingers around the shaft, stroking it a few times, and in return the stranger moved his hips even closer to the hole, enough for those big round balls to come popping through, too.
I took them in my other hand, feeling a small shiver of pleasure run through me as I assessed their impressive weight and warmness in my palm, while I continued to stroke his dick – which was growing harder and thicker by the second, already pulsing in my fingers with each fresh stroke I gave it.
I kept my eyes fixed on that big, purple head – the only word I could use to describe it was juicy. And before long, I found myself giving in to a new temptation, rising a little on my knees and parting my glossy lips as I guided the cock towards my mouth.
I felt another powerful flash of pleasure rocket through my skinny frame as I finally wrapped my lips around that velvety head, sliding it deep into my mouth, bobbing my head and working my lips up and down the thick pulsing shaft while I continued to cup those big smooth balls in one hand while stroking with the other.
And I could feel my own little prick starting to tingle and ache in my panties as I sucked, faster and faster.
But I’d only been working on my mystery for less than a minute when I suddenly felt him grow rock hard in my mouth, a muffled grunt coming through the thin partition wall, and then all of a sudden, with a shudder he began to unload – squirting a series of thick, powerful jets of cum right into the back of my throat.
It happened so quickly, it caught me by surprise, and for a moment I pulled away, coughing, the cum spilling from my lips and spattering onto my pretty blouse, while that big meaty cock continued to squirt out its load, a little going in my hair and on my face, while the rest sprayed onto my neck, not to mention the floor before me.
I gulped back what was left in my mouth, letting go of the dick and watching as it slowly withdrew, sliding away into the darkness of the hole, leaving me there, spattered and sticky, disgusted and ashamed, yet at the same time shivering and turned on, the salty taste of that strangers load still strong in my mouth.
As he zipped up and left, I did my best to wipe up all the cum from my blouse and neck, looking around for some kind of towel to brush it off my fingers. But of course, there was nothing in that bare cubicle to clean up the mess.
So instead, I lifted my hand to my mouth and licked it, gulping it back, again feeling my little sissy prick straining and aching in my panties – mainly at the thought of what a total slut I was becoming.
But I had little time to think, for even as I was licking up the last drops of cum, I heard the door opening again, and then the tread of a second heavy pair of feet.
This person walked slower than the first, from the sound of their ambling confidently up to the booth, it seemed like they’d done this many times before. I waited, poised before the gloryhole, wondering what kind of cock was going to slide through this time ...
I heard the slow, tantalizing zzzziiiippppp of their fly, and then, sure enough, it emerged: a thick hard dick, darker pink in color than the first and this time already rock hard.
I wasted no time in getting this cock in my mouth, quickly leaning forward and wrapping my lips around its meaty girth with a muffled sigh, glad once again to have the feel of a big juicy dick in my mouth. And this time, as I bobbed my head and jacked the shaft, slicking it with my saliva as I swirled my tongue all around that big bulbous head, I could feel the pleasure increasing in my own skinny body, as I rocked back and forth, shivering with delight as I threw everything I had into servicing this big anonymous cock.
In fact, it seemed the faster and harder I went at the task, the more my own enjoyment increased too, so I really gave in, getting good and sloppy, slobbering and licking and lapping at his dick, slapping it against my tongue, licking all up and down the shaft, even pausing for a moment to nuzzle those meaty shaven balls, sucking first one then the other eagerly into my mouth. I softly groaned and moaned, too, my own pleasure getting dangerously intense now – my little sissy cock aching and straining against the tight snugness of my panties as I continued to pleasure this anonymous cock, wrapping my lips once more around it and trying to slide my mouth down as far as it would go, until the pulsing head was nudging right against my throat and my eyes were pricking with tears.
And before I could even gasp for air, I heard a low growl, then once again felt my throat flooding with hot fresh cum.
This time, I kept my lips wrapped tight around the pulsing shaft, gulping it all back, feeling the waves of pleasure shuddering around my own body too, almost like I was about to cum, but not quite yet ...
As the cock started to soften in my mouth, I continued to lick and lap at it, cleaning it and bathing it with my tongue, not wanting to waste a single drop of delicious cum this time. In fact, it was only the anonymous stranger on the other side of the partition wall starting to pull himself away that stopped me, and I felt doubly eager for another cock now.
Luckily I didn’t have long to wait, as before I knew it there was another dick being pushed through the hole – this one thick and fat and black. In fact, it looked an awful lot like Tyler’s dick, the guy Mistress Cartwright had been exchanging messages with, just a few weeks ago – that image from her cellphone felt burned into my brain.
With an excited gasp, I leant forward, taking it in both hands and jacking it, marvelling at its girth, not to mention the silky smooth heat of its skin. I parted my lips once more, opening my mouth as wide as it would go to fit this big beautiful beast inside, groaning a muffled groan as I felt his hot thickness fill my mouth completely, sending a fresh shudder of pleasure through me, my tiny little sissy dick once more on the brink of cumming, without me even touching it once.
Like a cock hungry slut, I jacked his cock faster and faster, bobbing my head in time as I worked my lips up and down, up and down his pulsing shaft, feeling fresh shudders of pleasure as I heard my mystery man begin to sigh and moan too, from behind the thin partition wall.
God, I felt so dirty, so utterly slutty and kinky, there on my knees, my mouth stuffed full of big black cock, the slobber falling from my chin as I continued to suck on it as fast and hard as I could, all the time feeling my own body responding too, my nipples tingling the waves of pleasure shooting around my skinny frame, my little sissy cock on the bring of squirting.
And it seemed like my stranger was about to blow his load too, because I felt him growing harder in my mouth. Wow, I was actually getting pretty good at this! I sucked harder and faster, desperate
for more fresh cum, and at the exact moment he finally blew, filling my mouth once again with a hot sticky load, two things happened:
The first was that I came, too, my lips clamping tight around his meaty shaft stifling a muffled whimper as my body quaked and shuddered with pleasure, and I felt my cock finally flooding my panties with cum.
And the second was that just at that very moment, the door to the cubicle flew open, and there stood Mistress Cartwright, staring down at me dismissively, as I groaned and slurped on that big black dick, my body still shivering from the intensity of my orgasm.
“Good lord, Penny,” she snapped, “are you still only on cock number three?”
I pulled the sloppy wet dick from my lips and looked up at her, wiping my mouth with my chin and nodding, as I swallowed back the cum, the last waves of my pleasure flashing around my body.
“Yes, Mistress,” I offered back timidly.
“Well, get a bloody move on,” she hissed. “It’s nearly eleven o’ clock already. You’re going to need to go twice as fast as that if you want to be finished by the end of the day. In fact ...”
She paused for a moment, a naughty smile playing cruelly across her lips, then nodded to herself.
“Yes, I think I’m going to stay here and watch you for a while,” she said, stepping into the cubicle and shutting the door behind her, sealing us both into the room.
“Mistress, please,” I moaned, god knows how many hours later. “I don’t know how much more I can take ...”
I’d spent the whole damn day on my knees in that room, sucking cock after cock – some small, some huge, some dirty and smelly, some freshly washed and shaven – each one squirting its load into my mouth, which I dutifully swallowed, until my stomach felt full and my knees were red raw.
I’d cum four times myself, too, and my panties were totally soaked through. My whole body was utterly exhausted, but Mistress Cartwright didn’t seem to show any mercy whatsoever.
