Unpaid Debts Ch. 03

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Kelsey is learning her new role as an office slut.
9.7k words
4.6
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Part 3 of the 4 part series

Updated 04/29/2024
Created 03/31/2024
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"Ahh... ahh... ahh Clement... " I moaned, my hands spreading my ass open for my boss.

"Shut up and take it slut -- quickly, before lunch break ends."

"Ahh... ahh... ahh... ahhh!" The intense feeling of being rammed up my butt was euphoric.

"You're the fucking best hire I've ever made -- good at your job, and you take dick like a streetwalker. I really need to check who recommended you."

"Ahh... ahh... fuck me, keeping fucking me," I begged him, urging him on with my words and body.

"I don't think I'll ever stop, Helms. Fuck! Here's your load!"

Just like you probably are, I was wondering how I'd wound up in the men's room, getting rammed up the ass by my boss.

About a month prior, I'd decided to do a little whoring as a side hustle -- just to tide me over until I could find a real job. I'd met a man online named Richard, and he'd seemed safe enough, so then I'd met up with him in person. My session with him had done something to me; it had destroyed whatever that thing is inside of a woman that stops her from being a complete and utter slut. Call it decency, self respect or whatever. Whatever it was, mine was gone.

From that point on, it had felt like I was an open book, an unlocked door, a free fuck. Richard had fucked me once more and has not contacted me since. and in his stead Clement had resumed from where he left off. After my hiring, Clement had taken to fucking me silly at every opportunity. Clement was the boss. Joel, his brother, who was also my superior, took his own turns.

Clement had me fuck a few other men;, they were all rich and wealthy, just like he was. They all had families, wives and reputations, but they were all happy to pay Clement -- and, by extension, me -- quite handsomely to commit infidelity. Clement had final authority over me, though, and he fucked me hard and often. Even though he was well over fifty, the man had some energy to burn.

Kate, my new assistant, would often find herself needing to do some of my work whilst I was getting cocks stuffed into me. It helped that Kate wasn't above the same treatment; neither was the snotty assistant, Zahra, who would occasionally be forced to join in pleasuring the executives.

I'd been close to quitting. Clement and Joel had insisted I suck their dicks before an important presentation. After I'd done so, I'd freshened up, then gone to the presentation, where Clement had scolded me for being late. I'd felt utterly humiliated professionally, which had been where I'd felt I could actually draw a line. I'd wanted to give them a piece of my mind the next day, no matter how horny I'd been to suck their cocks again.

When I'd gotten home, though, my phone had rung, alerting me to the fact that my first paycheck had arrived. Not even a month in and twenty thousand dollars had been deposited straight into my bank account, which had been at ten dollars and a few cents just a moment before that. In an instant, I'd gone from thinking I'd have to scrounge up some change for a slice of pizza to planning out a shopping spree -- and not just for me, but for my daughter

My greed had gotten the better of me. I'd told myself I could handle it -- if, perhaps, only long enough to secure our future. I'd told myself all sorts of things, actually -- like that Clement wasn't so bad, especially when he wasn't randomly yelling at me to assert his authority; that Joel was a bit of a sweetheart when he wasn't being a pervert; that Kate was kind of nice to talk to when she wasn't trying to put me down to the other girls in the organisation. I'd had twenty thousand new reasons to believe it.

My resolve had been tested the very next day; the two brothers had brought in Kate and insisted we fuck each other with strapons in front of them.

They'd barely touched us as I'd clumsily put on the stupid thing and fucked my assistant silly. I hadn't really known how it had worked, or how to properly fuck a girl. Kate's steamed glasses and flushed face had told me I was doing something right. As if that hadn't been enough, once we'd been done with each other, the men had joined in, fucking us both to orgasm after orgasm. Kate was a screamer. She moaned like a wild dog and cooed like a pig. It was always shocking how no one ever just came to check if she was dying. I'd assumed then that the behaviour was an open secret -- that most everyone knew what happened in Clement's office and didn't care.

The fucking itself hadn't been all that intense -- child's play compared to Richard's machine-like butt fucking. It had been that very day when Clement had taken a liking to stuffing his cock in my butt. He'd just shoved it in there, and when I hadn't gone crazy or complained, he'd kept going till he'd filled me with cum. He'd then started prioritising fucking me there as well.

In terms of my actual job, I was good at it; their company had started getting more recognition, and Clement had taken all the credit. My reward had been his cum whenever there'd been a weekly progress meeting and the improvement of the company's marketability had been discussed. Clement would just smile and say it was all due to his ideas. Later, he'd drag me to some closet somewhere and tell me I was a good whore for keeping my mouth shut and letting him hog the glory. He'd then shove his dick into my mouth -- not that my mouth would resist. I'd deep throat the executive and get a serving full of spunk for my troubles, my gracious reward.It established me as Clement's favourite.

Kate often found herself pleasing Joel, but she preferred Clement. There were daddy issues there, because I could see that Kate always wanted to impress him. Clement hired her when she was very young so it's no surprise that Kate spent so much time trying so desperately to get his attention. First, it was her trying to steal my ideas just like her boss. Clement wasn't buying it, often telling her to shut up before resuming his focus on what I was saying. Next, Kate started being just a little skimpier, her skirt just the little bit higher. Once she realised all that did was get Joel to keep dragging her away for a closet pounding. Kate resorted to almost throwing all shame and decency aside and just throwing her body into Clement.

This approach kinda worked, the first time at least. Clement was impressed she was so brazen and that turned him on. He then pulled up the woman's short skirt and gave her a fucking. All while I gave my briefing to him, it was difficult to do that over a screaming dog getting filled up.

Here's the thing: I may sound annoyed, infuriated and frustrated, but in truth, I had my dream job. I didn't like some of the people there, but I was doing what I'd been trained to do, I was improving the company, and I was being well rewarded for it -- with money, even, and not just sex. That being said, I was also getting the good fucking I needed day in and day out.

What was wrong with me? I'd asked the question so many times it had become meaningless. When fat people ask themselves why they can't stop eating, they feel shame. When smokers try to quit yet again and fail, likewise. Whenever I'd ask myself why I was such a greedy little slut, I wouldn't know the answer. In the meantime, I'd take my fuckings and like them. I'd like them when Clement used me like a sex toy, with zero regard for my well-being. I'd like them when Maddy had been acting real bitchy to me, when I'd had an awful headache and period pains, and even after I'd received bad news about distant relatives passing away.Why was I such a whore then, why did I like it when Clement fucked me without much care for my well-being. Even when Maddy acted real bitchy to me, even after I had some awful headaches, and period pains. Even after I received bad news about distant relatives passing away.

When I'd come into the office that morning, I'd gotten started on my work right away. It hadn't been long, however, before long I'd heard my boss come in and demand I go into his office -- which had meant there'd been about a one in five chance we would discuss work, and in all likelihood he'd just want to deposit his cum somewhere in or on my body.

That pretty much gets us back into men's public bathroom, where my ass was getting fucked by my boss. My tits were out and I'd already sucked his dick that morning. I'd asked him to fuck me several times.. I'd begged him to use me and treat me like a slut. I'd told him that I wanted to be his whore and that he could fuck me wherever he wanted.

I'd said all of those things. Me! No one else.

I was falling deeper into the grave I'd dug. I couldn't see the light, and I couldn't hold back anymore. My mind was just done pretending to be a decent human being. I was a whore. I was his whore, and if Richard had been there, I'd have been his whore, too. I liked it, and I felt like I would for a very long time.

I wished there were more men in the stall, watching me getting railed -- watching my boss spreading my ass cheeks and slowly easing his cock back inside my asshole; my boss, who was holding my hair and pulling me up so that he could whisper to me just how much of a worthless slut I was -- how he planned on using me, fucking me, then letting his friends fuck me, too; how much he enjoyed fucking me over his ugly wife; and how he would fucking divorce her for me if it wouldn't have cost him half his shit.

"Fuck this whore!" I exclaimed. "I want to be your mistress, Clement... ahh, I want to be filled with cum. I want your wife to taste my ass and pussy when she sucks you off!"

Clement gasped audibly, then jerked around. His cum oozed into my tight and well-fucked asshole. I was tired; Clement was spent. He fell on top of me, and I felt his cum fall from my ass crack onto my panties, which were still wrapped around my feet.

"You're the very best hire I've ever made, Helms... take the day off."

"You mean it sir?" I asked, a bit surprised.

"Yes. Get out before I change my mind."

I tried to shift out from under him. I pulled my panties up, leaving the cum inside my asshole. Then I picked up my heels, as they'd fallen off as we'd fucked. I was so close to getting out of there.

"Helms, meet me tonight at the Four Seasons hotel. Wear something sexy because I want you to meet someone."

I figured it was another executive set up -- one which most likely would lead to sex. I supposed I'd need the energy, which meant that my impromptu vacation day hadn't necessarily been a kindness, or unplanned. He wanted me to be a good fuck for his buddies, and it wouldn't be the first time I would do so.

The last guy had me suck him off under the restaurant table. I'd liked that it had been a public place. It had excited me to know that anyone who'd have looked under the table cloth would have seen me. I'd touched myself as I'd licked his cock -- fingered my wet pussy as he'd come all over my tongue. Once I'd finished, I'd come back to the surface where I'd licked my lips, much to Clement and his friend's delight.

That had actually gotten me a bonus of three thousand, in cash. Clement had told me it was forty percent of the actual money he'd been paid, taking a majority share like he was my pimp. I'd started to get the sense that I was a hot MILF for these men, and that my general insecurities about my looks were not at all reasonable. I was a hot mom; my ego was shot up.

As I drove home, I wondered what exactly Clement had in store for me -- two executives at the same time, or perhaps toys, whips, chains, and handcuffs. I didn't really want to think too long on the subject, though, because I had to prepare: rinse the cum out of my ass, get some sexy lingerie, and take a few painkillers. I'd learned a few hard lessons in the beginning.

I passed by the mall; it wasn't one of those luxurious ones you see in the central hub of the city. It was just a quaint little spot. I wanted to surprise Clement and whoever he was going to introduce me to. The Four Seasons Hotel was no joke, unlike some of the other places Clement had organised our previous meetups. It was where celebrities and the wealthiest people met.

I imagined Clement thought our special guest to be of great importance; it definitely made sense to believe so. I needed a dress, and since I had more cash than I knew what to do with, I decided to "invest" some in the business. I went immediately into Victoria's Secret. Once inside, a few young ladies came to greet me and offer advice on what was hot. I pushed them aside; I knew what I wanted. I'd already seen it in the catalogue: a black mini dress with a v neck dropping all the way down to my belly. It had been love at first sight.

I had big breasts; I wanted people to see them -- at least from the side. My skin was in great condition, too, so I wanted to show it off. I tried the dress on and realised the size I'd gotten was a bit too big. On top of all the other perks, the sexual part of my new job was apparently helping me to lose weight. I peered outside the changing room to ask the woman for a smaller size, but she'd disappeared. The dress I was wearing was rather skimpy, but I didn't want to remove it and then wear my clothes just to ask for another. I walked out wearing a dress that came down to just below my ass and showed my whole chest.

I found the lady who'd helped me before. She was talking to some young teen. I got her attention by tapping her shoulder; only then did I see who the teen was.

"Mom?"

"Maddy?"

"What are you doing here?" We said in unison. My daughter was supposed to be in school. As far as she knew, I was supposed to be at work.

"I'm the adult here, young lady."

"You look like a whore, Mom," she countered.

"That's no way to talk to me!" I exclaimed. "Why aren't you in school? You are ditching classes even though you're so behind they might not let you graduate." I was furious; my daughter was throwing away her future. I didn't want her to struggle the way I had when I'd had her.

"Mom it's no big deal, okay?"

"No big deal... No big deal?" I'll admit it: I was shouting.

From the corner of my eye, I noticed a long-haired man come up to me. He had torn jeans, and I could smell a mixture of oil and tobacco emanating from him. It could only have been that hooligan she called a boyfriend, Johnny.

"Relax Miss H," he said. "Maddy asked me to bring her here. I'll take her right back to school after she checks for whatever it is she wants."

I didn't trust Johnny -- not in the slightest. He was a chop shop worker with no college degree and, god knows if he'd ever graduated high school.

I stared Maddy down and pointed in Johnny's direction. "Is this what you're aiming to be? A bum like him?"

"Well this bum has been picking me up from school and taking me home -- unlike you, my mom," Maddy crossed her arms in true defiance.

I wasn't going to stand for that.

Smack!

I didn't even think before I did it, hitting Maddy. That was the very first time I'd ever hit her. IHer loud mouth had finally gotten the better of me -- or maybe it was more to do with the fact that Johnny reminded me so much of her father -- the same personality and the same behaviors. With a bit of a time-shift, they could've passed for brothers. I remember when I was her age and how falling for those looks led me astray. I had tried to persuade her to stay away from him. Clearly that hadn't worked, and so I'd resorted to violence.

I regretted it the moment I did it. Maddy's shocked expression, followed by her watery eyes, calmed my rage.

"Maddy... I'm soooo--"

"I hate you!" Maddy yelled before running off.

Johnny tried to grab her. "Maddy, she didn't mean it... Maddy."

Maddy left before he could stop her.

"Sorry Miss H," Johnny said. "She doesn't mean that; I swear." He then made to follow her, but after just a few steps, he turned around. "Let me just say: you look sexy as fuck, Miss M."

I may have not liked Johnny that much, but hearing him say that about me triggered something inside of me. All of a sudden, I found myself wondering if I'd read him wrong -- misunderstood him.

The saleswoman asked if perhaps I wished to dress up and leave. I didn't blame her; she probably thought I was going to cancel all my plans and chase after my daughter. Clement didn't seem like the type to take cancellations, though.

"I need this in a medium," I told her, "and what was she asking about?"

The lady guided me to the set of lingerie Maddy had planned on buying. I couldn't imagine she had the money to pay for it, so that left Johnny -- the person it was undoubtedly for, even though she'd be the one wearing it. With her boyfriend's parting words rattling around in my slutty brain, I had the bright idea to buy them for Maddy -- a peace offering, you might say.

I loved my daughter, and having her say she hated me was the worst thing that had happened to me since her father had left. The dress I wanted fit perfectly, and once I got that and her lingerie set, I headed home.

When I arrived, I realised that Maddy had beaten me there. The breadcrumbs on the counter and her jacket on the sofa told me she'd sat around for a bit then gone to her room.

My meeting at the Four Seasons wasn't for another three hours, so I decided to go talk to Maddy. With the bag containing her lingerie set in hand, I went upstairs.

Knock knock knock'

I waited, and heard voices. At first I thought she was watching something but then I realised there was someone else in there.

BANG BANG BANG I hit the door hard. "Madeleine, who is in there with you?"

"No one," Maddy said. I heard more movement.

"Madeleine, open this door now!" I'd finally had enough and ran down to get the spare keys. Before I could reach the top step, Maddy opened the door.

"Mom... come in."

I turned back around and slowly entered. Maddy was warmer than usual and was visibly sweating, like she was hiding something.

I looked around and so no signs of anyone else being there. "Are you sure you were alone?"

"God, Mom, do you have any trust in me?"

Her sad look was enough for me to drop my suspicions. Maybe someone had been there, but it if they had, it looked like they were long gone. Instead of snooping, I gave my daughter a hug.

"I do trust you honey; you're my baby. I know you wouldn't do anything to jeopardise your future -- the one I've worked so hard to give you. Here." I handed her the bag.

Maddy took it and looked inside. "Oh my god... Oh my god... Oh my god... Mom thank you!" She jumped up and down, excited.

"I got a bonus at work, so that's why I was at the store."

Maddy stopped jumping. She gave me a knowing look -- a raised eyebrow and a naughty smirk.

"Mom, are you dating someone?"

"No, dear. Why would you say that?"

"It's just, you've been leaving home late and coming back even later. It's okay if you're seeing someone. You deserve someone to distract you from whatever I'm doing."

I smiled. She clearly liked the freedom that came with me spending extended hours away.

"I know you just want me out of the house so that hoodlum can come see you. Perhaps he was the one I heard at the door."

"Mom, a boy in this room? No way, Johnny is just a friend. He fixes cars, and competes in those race thingies."

"You mean street racing."

"No, Mom. Look, Johnny is a nice guy. Maybe you should invite him for dinner and talk to him yourself."

Maddy actively trying to make me and Johnny get along suggested to me that they were more than just friends.. My girl may have been in love -- not that it was enough to change my opinion of Johnny. I had thought I'd known what love was at eighteen, too.

"Well, let's organise it then. How about this weekend?"

"Sounds good, Mom."

"Okay. So, I am gonna be out tonight."

Maddy gave another knowing smile. I could only hope she never would -- know, that is.

"Enough of that, young lady," I said. "It's for work. I left money on the table for pizza. No boys allowed after I'm gone. If you bring a friend, then make sure you text me her parents' number."