Unpaid Debts Ch. 01

"Suck it bitch!"

I cringed at the sight of it, it was thick, large, veiny and most of all powerful.

"Bitch, I said suck it or else. I don't need to explain to you what the consequences are."

They surrounded me, in this dingy street with their floodlights on. There was no escape, no running away from it. I had to give it up, my pride, my decency and please them, or they'd take away the one thing in those world that mattered to me. My daughter.

I opened my mouth and tentatively sucked the cock presented to me, they watched quietly. This area of town was quiet, so my slurping was all that could be heard. His cock was warm, salty but super hard. Was it the fact I was desperate, doing this to save my, and my daughter's life. Did I turn him on, me some woman in her 30s turn him on. A man who probably had the means to have any young slut he wanted.

I was pathetic compared to some of the woman I saw draped around his arm, draped around the arms of his men. Yet he was hard, so hard, and his pre-cum kept dripping into my desperate mouth. It tastes so tangy, so salty, and I had to keep swallowing it. I had to play the whore, but why was I doing such a good job. Why did it excite me so much to be used like this, why am I wet.

I'm a single mom, maybe the time I spent not being touched has made me this way. To the point, just having a cock in my mouth is enough.

"You like that whore?"

He finally said, I'd been sucking his meaty cock for a few minutes now. Getting a good taste of him, I did like it, but what mother admits that. What self-respecting woman admits they like sucking an almost stranger's big cock. I was not some young harlot any more. That's what got me pregnant with Madeleine, or Maddy as I call her. I was a grown woman with responsibilities, and yet...

"I do like it," I replied, with my words and my eyes staring up at him.

He smiled, and caressed my black hair.

"You better, you'll be doing this often. Not just for me, but for any one of my mine."

I nodded, I didn't want to upset him. I put his cock in my mouth, and slowly sucked it like the whore that I was becoming. I relished the taste a bit more whilst on my knees. Perhaps my outfit didn't help much, I had worn some boots, a leather short and a tube top. The aim was to fuck my way out of this, but things didn't go to plan. Suffice to say I made a lot of mistakes to get in this situation, to have a cock now hitting the back of my mouth.

"What a whore you are, but you need to learn to suck dick better." He said, a demoralising statement. Why did I care what he thought about how well I sucked his cock. It's not like I liked him, or had even met him before tonight.

He pushed me off my knees and I feel back on my ass. I could see his eyes preying on me, I had rarely ever seen someone like him look at me this way. There was a deep lust in his eyes, one I knew had sick intentions.

"Men, this whore needs to learn how to suck cock. It's your job to teach her, understood."

They all started pouring on to me from the shadows where they stood. Until this point the brightest thing in this alley way was me sucking a man's cock. Now they came, dozens of them, with their cocks out. I didn't have time to readjust, they grabbed my head and shoved their cocks down my throat. None were as big as their bosses cock, so they simply slid right in.

The rest who weren't getting their dicks sucked by me were rubbing them against my body, they eventually ripped off my top. They were about to tear apart my black leather short.

"No one fucks her before me." He said with authority, and no one touched my shorts for the rest of the night. My breasts, they'd grown so big after Maddy was born. My mouth, my hands, and even my armpits were treated like substitute entries for their hard cocks to use. I was their whore, all of them. From the lowest of the low tier members who joined yesterday to the highest executives of the gang.

Men who would never have a chance of touching me were using me like a cum rag, some were hot and if I was horny would definitely have gotten a good fuck. The vast majority were men I probably wouldn't look at twice, but they fucked my mouth for hours. I swallowed so many loads of cum. They jeered at me and called me everything under the sun that meant whore or slut or cum dump, I even heard some italian and spanish in there.

I think by the 2nd hour I had simply just accepted my fate, what was worse was the ever increasing ocean in my panties. It was a mess in there and I didn't understand why. Why was I enjoying this, why did it turn me on that these men were doing this to me. I'm not a whore am I?

Surely not, surely I can't be enjoying this. I thought to myself, but I was, my nipples were hard. It wasn't the cold air because I loved it when they flicked them, pinched them, sucked them. I desperately wanted to be fucked now, I wanted it so bad that I even shook my ass a bit whilst I sucked their cocks.

"Boss, she looks like she wants us to."

"It's not about her, she'll get a good fucking when she learns to suck cock. She's ours now and she knows it."

He was right, I was theirs. I couldn't run any more, I had to please them before anything else. I finally milked the last man of the group, his cum squirting all over my cum covered body. You'd think someone had poured lotion all over me, with the way I looked.

"Good work, let's go men."

I heard their footsteps dispersing, their engines turning on and their cars leaving. They were leaving me like this, semi naked with cum all over me. One car remained, his car, and he stood in front of it watching me as I lay almost lifeless.

"Don't run from us ever again."

His last words before he turned around and left me.

One month earlier

"Fired!"

"I'm sorry Kelsey, I don't think we can use you any more."

"Pete, I have a daughter, rent, bills to pay. You were suppose to give me a one month notice."

"Well actually in the contract you signed, you're a freelance hire. We're under no obligation..."

'Bang,' I slammed the desk in anger, I had done so much for this piece of shit company. After my graduation they hired me, and for the last 15 years I'd been their top performer and suddenly with all this covid nonsense they fire me.

"Me, of all people, not the 50 of so useless dirtbags in the office behind me."

"Listen, this is the list, upper management determines who gets sacked."

"So when you saw my name on the list, you didn't vouch for me. Not a word, nothing?"

"I didn't have a choice in the matter, Kelsey, if I speak up they threaten to fire me too."

"You only have this job because I recommended you, you got promoted ahead of me because when they wanted me I told them to go to you instead. Why, because you're my friend, you think I'm gonna sit here and let you treat me like this."

"Kelsey, don't make this harder than it needs to be, if it were up to me you'd be getting promoted."

"You're damn right, I would. I may not have a fancy degree from Yale like you, but I have 15 years behind me. I put everything into every damn day of my job all while dealing with a teenager at home who regularly wakes up hating me. Do I complain, no! I'm not going anywhere Pete, tell management they are going to have to come fire me themselves."

"Listen, I know this is tough. I have to get this done by today or my ass is on the line. You need to clean out your desk like now and leave the premises before I call security."

I didn't budge, not that it mattered. Security simply came and carried me out, tossing my stuff at me at the bottom door. They even damaged my daughters junior graduation picture. I scrounged up my belongings and saw the judgemental individuals coming in and out.

"Don't work with Parkers Investment, they'll fuck you right in the ass." I shout out as I carry my stuff and toss them in the car. I sound like a crazy person, someone who has no idea what they're saying. Once I get everything inside, I suppose my real emotions overflow and a breakdown.

This job was my safety net, I was covering everything with the salary from my job. I did consider getting a more concrete contract after becoming a full-time worker. I had no experience and thought I was so extremely lucky. Every time I looked at that contract I told myself, 'no way they randomly fire me right,' and here I was jobless without a single protection.

It was a good job, even without the healthcare or insurance. I was good at it too. I drove home, my tears ruining my makeup. I looked like a witch, and didn't bother unloading some of my things from the car. I just entered the house and fell asleep on the couch.

I felt sorry for myself, my whole life was a mess. Firstly I got pregnant really young, senior year of high school, and the man that did it ran off to Europe. He was an Italian man, really handsome. At least I thought so, and back then I was somewhat of a cock gobbler. He wasn't the first man I'd been with, he wasn't the only one. I did graduate high school, the same year I got my Madeleine. After having her, I had to work a job to cover her expenses and save up for night college lessons.

You could say I have been working since Maddy was born, my grandma took care of me, but on her retirement fund she couldn't cover all our needs and my getting pregnant did help the issue. Gammy passed away after I got my job, I like to think the change I made in my life made her proud. Little did I know Gammy was in-debt and I inherited it. Gammy had paid for my tuition by borrowing money in my name, so the banks assumed I had taken out these student loans.

It wasn't unusual, everyone has student loans in their adult years. It was however, a bit of a problem, since a chunk of my salary was cut. This meant I had to do my job well, do overtime as well as find bargain deals for cars and gas. Not just that, my daughter hated me because whenever she asked for money I had to tell her no. I remember what it was like being a girl, not having the coolest clothes or going to the coolest concerts or events because you can't afford a bus ticket.

I dreamt of a better life for me and my daughter, one with a big house and a fancy stuff. I guess I'd need to find a new way of getting that.

When I woke up, I checked the time.

"Shit!" I forgot, Maddy asked me to pick her up. It was 6pm, Maddy finished at 3.

I got in the car and rushed to the school, it was still slightly visible out. Once I got there, I found Maddy sitting alone on the bench. I didn't have to see her face to tell she was not happy, not in the slightest. Maddy saw my car, but kept sitting, pretending I wasn't really here. I honked my horn and she still kept still, I did it a few more times. Not in the mood for her bratty behaviour.

This time louder, this time longer. Finally I stuck my head out.

"Maddy, get in the car. Now! Young lady."

Maddy stood up, her arms crossed, and she got inside.

"You know, Johnny offered to give me a ride home."

"I don't like that guy, and you know that."

"That guy can take me home on time."

Johnny was Maddy's boyfriend, I didn't like him. He reminded me way too much of Maddy's runaway father. Way too player-ish for my tastes. Yet another reason why Maddy hates me.

"Well he isn't your mother, and I don't want you seeing him or getting in his car."

"Ugh you're such a witch, you even look like one."

My mascara... I forgot to remove it. I checked and I really did look like something from a horror movie.

"Well if you must know I got fired."

"Well being on time is important." My jaw dropped at her insensitive comment, I didn't know why she had decided everything was my fault. In my opinion, she was just ungrateful to all the things I'd given her. A house, clothing, education and all she did was complain how things aren't as they could be.

We got home and Maddy ran up to her room, not paying any mind.

"You better be studying in there, Ms Walters told me you're failing Science last week." I yelled up to her, but I knew probably she won't listen to anything I say.

Throughout the next few days I started throwing out my resume to any company I could, it wasn't something that yielded any returns. It felt like a waste of time. No one wanted me because I'd only had one job, I only had a community college diploma, I was in my late 30s now, even though I was probably better than most of their junior executives at marketing products.

I then realised that If I was so good at marketing, then it was time I market myself. I tried to find other ways a woman my age could make money. I knew a job would come my way eventually, but before that happened, I'd need to do something that could keep me afloat. There were several options, many of which I didn't like. Call-girl sounded so tedious, constantly telling random guys what I was wearing. The others were all of a similarly sexual nature, cam girl, stripper, pornstar.

I couldn't do any of these options, but the unsexual ones paid pennies. I had way too much to pay for, finally the last option. Escort?

It was interesting, these were wealthy clientele. Offering $1000 per session, hmm, but a woman my age surely wasn't someone they were interested in. I went to gym often, to manage my stress, really. It meant I had kept my weight gain to a minimum. Most of my body didn't get the memo, my ass was still round and flabby. You could hear it smack if I bounced around, my thighs were also toned and thick. I had a slight tan, so it would be somewhat interesting to see if I got some bookings.

On a whim, I opened a profile and put some of my sexiest photos, ones I took on my rare visits to the beach. Ones I took when I was alone at home and had finally got a cute nightie to sleep in. I put just the two pictures and went on with my job hunt. Within hours, I had men offering to see me, some going well above the $800 price I set, reaching the low $2000s.

Was I really going to do this? Was I actually going to consider being an escort?

Later

We met up at a hotel, the man who matched with me called himself SinofLust12. He gave me details and said so long as I approach the lobby and say Richard sent me. They give me the right room, this guy was a high roller. The hotel clearly knew what he was doing and probably didn't care.

I knew this was a most certain pay day, so I put my eggs in the escort basket, I went and bought myself some new lingerie. Something that would be more appreciated because perhaps he was younger, a young kid spending daddies cash. I wouldn't be too bothered by that, it was not something I was too keen on encountering, but the money would be enough to cover this month's expenses.

I bought some hold up stockings, didn't want to disappoint him with some cheap either, they cost me $200. That and some heels, alongside a lace push-up bra. I even got someone to touch up my hair in case it didn't look too good, for the grand total of $350. Almost everything left in my account after I lost my job.

Once I got home and got dressed, making sure to wear a black coat that covered the alluring clothing. I paid for a cab, left dinner and note for my daughter. I also called her to ask Johnny to take her home, she was surprised and even happy. Guess a few freedoms go a long way.

Once I got there, and said Richard's name. The Hotel manager escorted him to the room himself, he opened the door to the penthouse suite and said if I need anything to call him directly. He didn't ask my name, why I was here, or even how long I'd stay. Who was this guy?

Who has this much power, I'd never heard of him and I thought by now I'd know who he is. Even more so was why he wanted me, some normal looking middle-aged woman. I mean, I wasn't old yet, but surely there were better ladies out there.

Perhaps he was a criminal, that would be the only way I don't know. I didn't have much time to think about, as I stared into the night sky. The door opened, I turned around and saw the person I assumed to be Richard for the first time. I approached him, clacking my newly bought 9' inch heels towards him. The man put down a bottle of wine and something I assumed leash. He looked at me, as I smiled at him.

"So, shall we start here or the bedroom." I had practised this line the whole way over here.

"Oh... I'm not the boss. He just asked me to make sure to get these things here before he arrives."

"The boss?"

"Yeah, oh, don't worry. Richard, right, yeah he'll be here. He didn't have time to pick these things up so he asked me to bring'em. I'm Bobby."

Bobby quickly got out of the room, I could tell he was flustered. I guess I hadn't lost my touch with men. Some seconds later the door opened again, this man was just slightly taller than bobby. I'd actually started to calm down, the anxiety was gone. When I saw him it was back again, I was turned on. He looked like a movie star, or a professional athlete.

"Oh, Welcome dear. I'm Richard... your tag was Sexymilf36. I assume the 36 is your age, but your real name is a mystery."

Richard had somewhat of that Britishness in the way he spoke. It wasn't well-defined, but it was there, he had black hair. He was tall, chiselled, but not stocky. I felt ugly, I really didn't even know how to react, I felt like a teen looking at her first crush.

"Hello, I'd ask again, but I think you heard me and are focusing on something else."

"Um yes, I mean no, I mean please say what you said again."

"I'm Richard, and you are?" He said as he took off his suit jacket.

"I'm, I'm umm Kelsey..." Richard undid his tie and raised his eyebrow.

"You don't sound sure that you're Kelsey."

"I mean I am Kelsey, I mean yes I'm Kelsey."

"Don't be nervous, Kelsey, you are in safe hands."

Richard turned me on, it was crazy. I was dripping, all he did was look at me, and I was soaking like a bitch in heat. What the hell was going on, never did any man make me feel like this. Physically he was hot sure, a nice height. A lovely body shape, I knew under his shirt were abs as firm as a stone wall. I'd seen this before, but there was something strangely mystical about all this.

Richard finally took off his shirt and revealed his well sculpted body. Something came over me, I was possessed. I dropped my coat and showed him the outfit I bought. Richard didn't seem to flinch, but that wasn't where I stopped. I got on my knees and fished out his cock. It was thick, large, veiny, I put it in my mouth and it was glorious. The type of unique tangy taste you fall in love with, the type of thing you could suck for hours.

"Oh well you're not the first one to be so forward."

I licked the bottom, the top, the shaft. I went wild, I went crazy... and Richard just kept his hands to himself and watched. I reached underneath my legs and touched my wantonly wet snatch.

"I...I don't know what's come over me, but please fuck me hard, Richard."

"I wouldn't have it any other way." Richard smirked, most likely in appreciation of himself.

I rubbed myself through my panties, there was a tiny puddle underneath me. Haunched on the ground, it was somewhat impressive how much had already seemed through the fabric of my panties. I pulled his cock up and got a mouth full of his balls. They were full, and swollen.

"Richard, please touch me a bit, I'm burning up right now."

"Stand up you whore!" I don't know where his gentlemanly persona went, but I stood. It didn't matter now, I was in his control. As soon as I was on my feet, he stuffed his tongue down my mouth, accompanied by the taste of brandy. His hands went to my warm mound, I managed to shave for this. I didn't have time to remove all of it, but it was trimmed enough to look neat.

He rubbed it slowly, feeling the damp material and tugging on my panties, which now stuck to my wet pussy. I raised my leg to give him better access to my pussy.