Kerry was a flashy woman. She was past her prime, perhaps in her early fifties, I’d guess. But she definitely still had it. She had a cute, slightly plump face framed by long, jet-black hair, big juicy lips, and dark brown eyes, with a tan I’d imagine came from a bottle. Her figure was starting to round, but she wore it well. Her voluptuous behind was always accentuated by a nice dress or tight-fitting trousers. Kerry exuded an air of superiority, as if she wanted everyone to know she had money. She paraded around the hotel where we worked like she had won the lottery, flaunting designer handbags, sports cars, and more. It didn’t help that she was married to the manager.

But I knew her secret very well, she was in a lot of debt, £12,750 to be exact. And I was the one she owed it to.

So when she returned to work after a week or two with a brand-new, expensive-looking set of breasts, I was shocked. She hadn’t paid off any of the money she owed me in the last four months. It was time to start threatening to reveal her financial struggles to our colleagues.

The next morning, Kerry walked into the canteen and saw me sitting alone at a table in the back. She strutted over like the queen she thought she was. Kerry didn’t talk to many people at work, but since I was management, she considered me an equal. As she sat down, she made sure I got a good look at her latest purchase, leaning over until her nipples almost brushed the table between us. She loved to flirt with me, but with her husband, Gary, being the hotel manager, I never thought it could be more than just flirting. Still, I often fantasized about being with her. Her voluptuous behind, perfect breasts, and luscious lips were enough to make any man desire her.

She sat next to me, looking all smug with herself, until I dropped the bombshell. “Pay me back by the end of the month, or hubby finds out you get your money from me,” I threatened.

I don’t imagine Gary would be too upset with me lending her money; I’ve lent to him in the past. He might be more upset by the fact that she didn’t actually have a second job anymore, as she’d led him to believe. In fact, she had been fired and was using my money to maintain her appearances rather than earning a second income.

When she heard my threat, her face dropped. She explained that she wouldn’t be able to pay me back before the month ended. She looked terrified until a little spark appeared in her eyes.

“You can fuck me! I know you’ve wanted to for years,” she whispered.

I was stunned. How long had she known I’d wanted to sleep with her, or did she just assume everyone would jump at the chance?

But I quickly responded, “Do you really think your pussy is worth over twelve thousand pounds, Kerry?”

Kerry now looked determined, realizing my answer wasn’t a straight no.

“How much is my pussy worth to you? Could we make this work?” she replied.

I laughed as a cunning idea came to mind.

“I’ll tell you what, Kerry. If you’re willing to use yourself as payment, I have a plan, a repayment plan, we could call it. I’ll finalize my ideas tonight. So if you’re still up for it in the morning, I’ll share my plan with you,” I offered back.

Kerry’s face had gone from smug to shocked to completely terrified, and I loved that. The canteen had started to fill, and I could tell Kerry wanted to end this conversation quickly before anyone overheard.

The next morning, I entered the canteen to find Kerry sitting there in the sluttiest outfit I’d ever seen someone wear to work. A short burgundy leather skirt clung to her big arse, and a low-cut top showed off her new tits. She also wore dark red lipstick that would definitely leave a mess on a cock. There were two other workers sitting in the back of the canteen behind Kerry, so I sat at the table in front of her, looking directly at her with a view of the people behind. I soon realized that the slutty outfit was even sluttier than I first thought. Kerry sat with her legs wide enough apart for me to see she had no knickers on, and her nipples were trying to poke out of the thin top she wore. She was definitely up for this repayment plan of mine, I thought.

The two workers stood up and left, and I overheard one whisper, “I’d make a mess of that stuck-up bitch.”

Kerry didn’t hesitate to move to my table. She leaned in and whispered, “You can fuck me once a week for three months, and I’ll suck your dick whenever we find ourselves alone on shift. That’s my offer.”

I laughed.

“As I said, Kerry, I have a plan to help you clear your debt. Now that I know you’re willing to sell yourself like a whore, it’s either my plan or the original threat of exposing you as all show. Did Gary ever find out why you were fired?”

The panic returned to her face.

“Well, what’s this plan, then?” Kerry snapped, eager for an answer.

I pulled out my phone and opened the Notes app.

“I have a list of ten scenarios here, Kerry. Each one has a number next to it. You’ll pick a random number each time until we’ve gone through the list. Each scenario is worth a different amount of money, with some offering bonus amounts,” I explained.

She looked more at ease now, though she was still visibly anxious and excited.

“Okay, this sounds manageable. And once we finish this list, the debt is cleared, right?” she asked.

“That’s right. I’ll even let you choose when to pick your next number. But there’s one rule: for every scenario you don’t complete, I’ll tell a random colleague about our secret,” I warned.

This visibly horrified her, and I could see it.

A few days had now passed, and Kerry was avoiding me. I saw her occasionally, striding around with an air of superiority, acting posh and looking down on other members of staff. Little did she know what was in store and the depths to which she would stoop. I resolved to remind her of our deal the next morning. However, before I had the chance, as I was walking down a quiet corridor, she snuck up behind me and whispered over my shoulder, “Number seven.”

I turned around, surprised to see her smiling. I ushered her into an empty bedroom. She sat on the corner of the bed with an inquisitive look on her face.

“Number seven it is, then,” I said, flicking through my notes.

“A nice, easy one to start with. Very high risk, but simple,” I teased.

Before I could finish, she interrupted, “How much will this knock off the debt?”

“£500 if you succeed. If you give up before the end, £100. But let me also warn you, if you don’t succeed, you stand to lose a lot more!” I cautioned her.

She stood up and got so close to me I could smell her expensive perfume. She was excited; I could sense it.

“C’mon then, tell me what I’ve got to do,” Kerry commanded.

I let out a little giggle; she seemed to enjoy this.

“So, the simple part of the task is, all you have to do is make me cum,” I said with a hint of sarcasm.

She picked up on that and blurted out, “I could do that with my eyes closed. If that’s what I’ve got to do for £500, you must underestimate me. Just because I’m posh doesn’t mean I don’t know how to please a man.”

I told her to sit back down and take a breath. This made her panic. She looked up at me to ask, “So if that’s the simple part, what is the risk?”

I walked over to the side cabinet and handed her the room service phone.

“I want you to call reception and request that Gary come to this room to check for quality control from housekeeping. That should give you about five minutes, I reckon,” I laughed.

She looked gobsmacked.

“What if he walks in on us?” Kerry asked nervously.

“Now that would be an issue. You’d best find a way to make me cum quickly, hadn’t you,” I teased.

Kerry, with no hesitation, reached out to pull my trousers down and get started.

“Easy, Kerry. Hands off until you’ve made the call.”

She sighed and made the call. As soon as she hung up, she had my trousers around my ankles. I was already hard by this point. She shoved my cock to the back of her throat and sucked hard. She wasn’t playing; she gagged for a few seconds, then pulled back, repeating this several times. I was rock hard now. Her lipstick stained my cock, and her makeup was starting to smudge. She took my cock out of her mouth and began stroking it with both hands. Fortunately, this wasn’t going to take long, she knew how to handle a cock.

She placed the tip of my cock back in her mouth and swirled her tongue around the head. One hand played with my balls while the other stroked the shaft into her mouth. I looked down, and she gazed up at me. I chuckled.

“I never imagined I’d have the stuck-up queen of the hotel sucking my dick for some money. Nothing better than a hooker, are you?” I teased.

“Ouch, you bitch!” I yelped.

She’d squeezed my balls and bit my cock gently at the same time.

“I deserved that, I suppose.”

I was nearing the edge when her mobile phone rang. It was Gary, the husband, the boss!

“Answer it, ” I ordered.

She pulled my cock out of her mouth to refuse.

“Answer it, and I’ll add £50.”

She answered, continuing to stroke my cock at a good pace while he asked if she was in room 308 or 309. When it was Gary’s turn to speak, I took hold of Kerry’s ponytail and filled her mouth with my cock, to her dismay. Her eyes screamed anger. She moved the phone away from her mouth, an attempt to hide the sounds of her gagging on a cock that wasn’t her husband's.

Then she hung up.

“He’s coming up the stairs now. We have about a minute, so hurry up and cum, you prick!”

That pushed me even closer to the edge. As I neared climax, she realized the next issue.

“Where are you gonna cum?” Kerry asked.

“In your mouth or on your face. Your choice. Surprise me.”

Her tone turned angry, and her expression was panicked. She stroked me faster and faster. I groaned as I neared release.

“You can’t cum in my mouth; Gary will want a kiss. We don’t have time to clean my face, so you can’t cum there. How about my tits? I’ll just pull my shirt over it,” she pleaded.

“No, mouth or face. I’m about to cum. Are you ready to decide?” I groaned.

She stroked me furiously, my cock now hovering over her face. I was eager to see what she’d do with the load she was about to receive.

“Choose quickly, slut. I’m about to blow!” I grunted.

Before I finished my sentence, my cock was back in her mouth, erupting down her throat. She had made her choice. Despite the rush, she ensured she swallowed every drop.

I’d just sat down on the corner of the bed after smartening up, I was spent.

Kerry looked relived, she’d rearranged her face so her makeup looked half decent again.

The door opened, in walked Gary, he nodded at me, and greeted his wife with a kiss!

Later that evening, as I was walking through the car park to my car, I encountered an angry Kerry.

“What’s up with you? You’ve reduced your debt and didn’t get caught,” I asked.

“Garry kissed me right after you’d finished in my mouth. I felt terrible,” Kerry replied.

“You knew what you were getting into. I’m sure you’ll make it up to him,” I teased.

“Well, erm, I already have. I was still a little wet and excited after our risky encounter, so when you left, I let him finish in my mouth as well,” she admitted with an embarrassed tone.

I laughed at her. A small amount of anger spread across her face.

“Nothing but a slut,” I mocked.

“Are you complaining? Next, I want number one, please.” She walked off before I could reply.

The next morning, I had a meeting with some of the leadership team. The meeting was in my office, which was next to Garry’s. It was a basic office with a desk and a sofa. After the meeting, Garry, Zoe, and John left, but Kerry remained on the sofa, pretending to have additional notes to share with me.

“Number one. Explain this one!” Kerry demanded.

“It’s another risky one but, once again, very simple,” I started.

“Fuck, do you want us to get caught?” she muttered.

“Not at all, but I want you to know you’re not the queen bee here. You’re just a slut who’s being used to pay off a debt,” I snapped.

Her facial expressions showed a bit of anger, but beneath that, I could see a hint of excitement.

“Hmm, carry on then,” she pleaded.

“Well, like I said, it’s simple. I’m going to fuck you, but I’m not going to tell you when or where. You won’t know it’s happening until the last second. The risky part is that until this happens, you need to wear a skirt or dress with no underwear. Got it?” I instructed her.

“Erm, yeah, okay. I’m just going to have to trust you not to let us get caught, I suppose,” she said with a worried look on her face.

I don’t think she quite knew how she was feeling about this, but she kept playing along.

Two days after giving Kerry the instructions for her next task, I found her on a night shift behind the bar. She was on her tiptoes, reaching for a glass on the top shelf. I slipped in behind her and put my lips to her ear. “Just checking,” I whispered.

I then slid my hand up her dress and found her bare pussy. I rubbed it with my middle finger for a couple of seconds, then withdrew my hand and walked off. I heard a deep intake of breath as I left.

Several days had passed since the bar encounter. I hadn’t had release in over a week now, and I was full to the brim and ready to explode. Today was the day. Kerry had been trying her hardest to make it happen over the last few days. She was purposely putting herself in positions around me where she would be bent over or on her tiptoes. I wanted her to know I was choosing the when, not her.

Today was a normal day at the hotel, slightly busier than usual. The hustle and bustle in the reception area were loud. Out of the corner of my eye, I spotted my chance. Kerry was heading towards the elevator, wearing a summer dress that showed off her big, juicy ass and wide hips. It tucked in nicely around her waist, and she was wearing boots with a large heel. I liked this outfit. It stirred something inside me, and my cock suddenly woke.

Kerry entered the elevator, and I slipped in behind her. When she turned to press her floor, her eyes met mine, and they widened with terror.

“Not here, no way. It’s too risky!” she pleaded.

“Press floor twenty two, turn around, and hold onto the rail tight. Don’t say a word,” I demanded.

She did as she was told. As soon as the door closed, I hiked her dress up, spread her legs with my feet, and yanked out my semi-hard cock.

I leaned over and whispered in her ear, “Don’t worry, slut. My balls are full and need emptying, this won’t take long.”

I had a hand on my cock, and a hand rubbing her pussy. It was hard enough to put inside her now. In fact, it was a solid eight inches already. I was more than ready. I rubbed the tip along her pussy just once before I squeezed the whole length straight into her guts. She let out a noise, a kind of squeal mixed with a groan.

“Fuck, it’s big. Be quick, but Jesus, be gentle with me,” she begged.

I didn’t respond. I slowly started fucking her from behind with long, hard, deep thrusts. I felt it bottom out every time my balls slapped against her pussy. Kerry’s breathing grew louder with each thrust.

“Floor twenty-two,” the lift announced.

We were at the top. How long would it be before someone called the lift? I knew the lift stayed here until called again, so we had some time at least.

A couple of minutes had flown by. My strokes were faster and harder now, but I still used every inch to pound her tight hole. I gave her ass a firm, hard slap, and Kerry squealed.

“Oh shit, I’m gonna cum on your dick. Please don’t stop,” Kerry moaned.

I did as she asked; I didn’t stop. I got faster and harder.

“Going down,” the lift announced.

“No, fuck, aghhhh I’m gonna cum!” Kerry squealed.

Her orgasm had started, I noticed her pussy tighten around me. I quickly looked around to see floor two on the screen. We had a minute at most. I fucked Kerry with all I had. Ten seconds later, I was filling her with my spunk. I felt pulsation after pulsation shoot deep inside her. I looked down to see Kerry’s legs shaking violently. I then came to my senses and heard her moans. Kerry was mid-orgasm as I pulled out and slipped my cock away.

“Floor two, doors opening.” The lift announced.

I quickly stood in front of Kerry to shield her from the view of the elevator’s newest passenger. It was Zoe, the receptionist. An old flame of mine, she smiled directly at me as she entered, she knew, and she knew I knew she knew. As the doors closed, I could see Kerry in the reflection. She was holding onto the rails for dear life, having managed to turn herself around. I could see her rock-hard nipples through her dress. Her face was red and her breathing was heavy. I think she was still on the latter stages of her orgasm.

I spent the duration of Zoe’s stay in the elevator flirting with her.

“Floor five, doors opening.”

Zoe left without saying a word to Kerry. I watched her perfectly round ass leave the lift.

“That was the best orgasm of my life,” Kerry panted with a look of lust towards me.

“Plenty more to come, don’t worry,” I reassured her.

“Good, I want number two next.”

I walked out of the lift without saying a word. I turned to face her and saw her trying to wipe her inner thigh, my cum had started to dribble down her leg.

“Slut,” I called to her as I left.

She responded by putting her cum soaked finger into her mouth. She definitely was not as high and mighty as she made out.