I woke up to the chime of a text message:

“I picked number 2 a week ago. What are you playing at, stop being a prick?”

I laughed. She was desperate now. I couldn’t tell if she was desperate to pay me back quickly or just desperate for cock. Either way, I had her hook, line, and sinker. I texted back after an hour or two:

“Ha, don’t worry, slut. You’ll be paying me back soon enough. See you at work tonight!”

The hotel was dead that night. We had two rooms booked, and both were no-shows. This fit perfectly into my plan. I could use the room without anyone being the wiser.

There were me, Kerry, and four other staff members on shift. As the most senior member, I assigned everyone their tasks. Kerry’s job for the night was not exactly hotel-related!

I walked down the quiet corridors to one of the unused rooms, room 508. It was the perfect room, top floor, far end and isolated from the other staff members. Once inside, I called reception, and Zoe answered. I knew Zoe hated Kerry; most people did. Who likes a stuck-up show-off who looks down on everyone? And to top it off, she was fucking the boss, so she got away with murder.

I asked Zoe if she and Kerry were still at the reception desk. Then I politely lied, asking if one of them could come to room 508 to clean up some mess on the floor.

I knew Zoe would pass that job on to Kerry, ensuring no interruptions.

Ten minutes later, Kerry walked in. She looked surprised at first—no mess to clean up and me sitting in the chair by the window. She quickly figured out what was happening.

She stood in front of the now closed door, her black shiny hair lazily sat on her shoulders. Her large arse and tits hidden under a tight black office dress, accompanied by a paid of red high heels.

“Take off that slutty dress and get on the bed. I’m going to my car to get a bag we need for tonight’s activity. And don’t just lie there, get those fingers working. I want you close to cumming by the time I get back.”

She was gobsmacked, and so she should be. Last time was risky; this time was all about humiliating her.

“Erm, are you going to tell me what it’s worth?”

“Ha, spoken like a real hooker. This one’s a good one for money. You’ll start at £250, but there’s plenty more to earn along the way.”

As I walked towards the door, I looked back to see her dress on the floor and her fingers slowly rubbing her clit.

“Good girl.”

I got to my car, opened the boot, and found the rucksack full of sex toys. Oh, she was in for a night of it! I walked back past reception and stopped to chat with Zoe. She was a lot younger than Kerry, in her mid-twenties, with a very different body type: a slim frame, amazing perky tits, and a small but shapely ass. She did have something in common with Kerry, they’d both had my dick in their mouths! Zoe was a great fuck, as I’d learnt on many night shifts, but she ended it when she found a boyfriend. They split up recently, and ever since, she’s been trying desperately to get me back as a fuck buddy. Without a doubt, she will be laid on her back with her legs in the air for me again, but I needed to let her beg for a while first. As I walked away, I had a naughty thought: Zoe sat on Kerry’s face. Hmm.

I got to the room, put my ear against the door, and heard very faint moans and the splashing sound of fingers violently going in and out a soaking wet pussy.

As soon as I stepped in, Kerry’s eyes darted to me. She was red-faced and panting, and her hair was a mess.

“I need to cum! You was ages…I’ve been holding back for the last ten minutes! Fuck, this feels so intense. Can I cum, or do you have any demands?”

She barely got her words out. I could tell she was ready to explode. I walked over to her, leaned in, and put my face as close to hers as I could without them touching and whispered, “Cum, you little slut.”

Her eyes rolled back, her back arched, her breathing was out of control, and her fingers were a blur, in and out, in and out.

I kept my face where it was, but to her surprise, I pinched and twisted both her nipples, which sent her over the edge.

“Fuck, fuck, fuck… ahhhhhhhhhhhhh!”

She lay back on the bed, looked at me with a confused expression, and said,

“I’ve not made myself cum like that for years, since my early twenties.”

She lay there smiling, not knowing what her body was about to be put through.

I stood up with the rucksack in hand and winked at her sarcastically.

“Now that you’re warmed up, time for the main event. In this bag are several sex toys, Kerry. I’m going to take one out at a time, show it to you, and tell you an amount. You simply give me a yes or no if you’re willing to use the toy for that price. Got it?”

“Sounds fun. What’s first?” she said through her struggled breaths.

First to be removed from the bag was a blindfold.

“No, definitely not. I need to be able to see what’s happening.”

“Do you not want a price, Kerry?”

“No, it’s not happening.”

Next were handcuffs, met with the same response.

The third item was a short cane intended for spanking. Once again, this was met with a no before a price was heard.

“Do I need to remind you of what happens if you don’t go through with a task?”

“No, I remember. You’ll tell someone our secret. I want to go through with the task, but those three things are my worst nightmare.”

Next to come out was a giant 12-inch purple rubber dildo. It was long and thick with five-speed settings. Her eyes looked terrified of it.

“That’s fucking huge. There’s no way that will fit inside me!”

“£100 says it will.”

“Fuck, erm, yeah, okay.” She finally agreed.

Next was a pair of tiny nipple clamps. They were small but quite heavy.

“£50”, I stated.

“You’ve just seen how sensitive my nipples are! But fine, it might make me forget about that purple thing.”

The final item out of the bag was a clitoral stimulating toy with a strap that went around the waist to hold it firmly in place.

“£50?”

“Oh yes, please.”

So we had our toys. I noticed Kerry was still slowly rubbing her pussy. I laughed, and she smiled in return.

“I hope you know what you’re in for tonight.”

The panic on her face was obvious.

“So, the rules of tonight’s game are simple.

Rule one: all three of your holes are going to be used until I’m satisfied.”

She was speechless; her fingers stopped moving.

“All three? Aghhh, please be gentle with me. Gary hasn’t been near my ass since before we were married.”

I laughed. “Don’t worry, you’ve got eight more scenarios to get through. I’m not going to break you on the second.”

She gave me a small smile and resumed circling her clit.

“Rule two: at all times, my dick must be in one of your holes and the dildo in another. This means one hole gets a rest each time. The clit toy stays on until you tell me to stop. If you tell me to turn it off before I’ve had a chance to cum, you owe me £500 back on your debt.” I explained.

Her face was now horrified, but her fingers had picked up the pace again, so something must have excited her!

“Rule three: I’ll set up a timer and move to the next hole every three minutes. Every time I change holes, you get £100 off the debt!”

Her fingers found their way back inside, and her breathing became heavy again.

I was now standing there naked. She was still gently fingering herself but now had my cock in her spare hand, getting me erect. We strapped the clit sucker on. When it turned on, she jolted with pleasure, but I quickly turned it off until we were ready. Next, we put the nipple clamps on. She didn’t look impressed with them. Wait until you get on all fours and they’re dangling, I thought.

“So, the choice is yours. Where do you want my dick and the vibrator first, and which way do you want to rotate?”

“First? Hang on, there’s no chance that purple thing can go up my ass.”

“Ha, I knew you looked a bit too calm when I said that rule.”

I laughed at her. She didn’t like that. She grabbed hold of it and examined it closely.

“It will rip me open. No chance. You’re lucky I’m letting you stick your cock in there.”

“Zoe”, I said.

“What the fuck has Zoe got to do with this?” Kerry snapped.

“Zoe is who I’ll tell our secrets to first.”

“Aghhhh, you prick!” she said in a loud, angry tone.

She took the huge purple dildo, threw it on the bed, looked at me, then rolled over and got on all fours in the middle of the bed. Her face was close enough to the side for me to stand, and her ass was close enough to the middle for me to get on the bed with her. Perfect.

I saw in her eyes she felt her nipples stretch when she rolled over, but she didn’t complain.

“That’s a good girl. So, what do you want where first?”

“Put your dick in my mouth so I can bite it,” she said sarcastically.

“That purple thing can go in my pussy to start.”

“Lovely choice, Kerry. And how would you like me to rotate?”

“Agh, fuck, this is hard. You’re going to have to go straight into my ass so I can suck the purple one first. Please be gentle. No one’s been near my bum in years.”

Her voice trembled slightly, but she steadied herself, ready for what was to come. The anticipation and fear were evident in her eyes, but so was a glimmer of excitement. As I positioned myself, I couldn’t help but feel a thrill of power and control over her. Tonight was going to be unforgettable—for both of us.

I grabbed a tub of lube and generously applied it to the purple dildo to ease its entry. Without warning, I squirted the lube onto her arsehole, and she jumped.

“That’s cold, you prick!” she exclaimed.

I gently massaged the lube in with my finger, letting it slip inside her. She drew a sharp intake of breath as I slowly circled my finger, letting her adjust.

I turned the clit sucker back on, and Kerry instantly let out a little moan, clearly enjoying the toy.

“Are you ready? Here it comes.”

She arched her back, lifting her pussy into the air. It took nearly five minutes to get the entire dildo inside her, and she was panting heavily. I turned it on to speed one.

“Wow, I can feel the end swirling inside me. ‘That fucker’s gonna have me cumming in no time,” she said, her words quiet and breathy.

I turned it up to four.

“Agghhhhh, that’s crazy! I’m going to cum already; oh shit, I’m cumming!”

Her orgasm was intense, lasting about thirty seconds before she begged me to turn it down. I obliged, dropping it to speed two.

I set my stopwatch for three-minute intervals, then walked around the bed to her face. I leaned down, gave her a kiss on the forehead, and wished her good luck. Then I stood up and pressed my cock to her lips, which slipped straight in as her mouth was already open from constant moaning and panting.

She took my cock all the way to her throat, her moans vibrating against the head.

“Get it nice and wet; you know where it’s going next!”

She looked up angrily but never stopped sucking!

She sucked it slowly and sensually, and before I knew it, the three minutes were up. I withdrew my cock from her mouth, sensing panic in her pleasured eyes.

“I’ve just had another orgasm with your cock in my mouth. Could you tell?” she asked.

I laughed and nodded.

“I’ve changed my mind, slut. We’re gonna keep that in your pussy. I want you to keep cumming.”

She seemed relieved until I got behind her and positioned my dick against her ass hole.

“Please remember to be gentle. Please.” She begged.

“Just relax.”

I slowly pushed the head of my dick in.

“Leave it there for a second; I can cope with that,” she said.

I left it in as she requested, noticing her breathing pick up and her moans get louder. Here came orgasm number four of the night. As she arched her back and moaned out another orgasm, I took the chance to push my dick all the way in. She didn’t even seem to notice, or at least she didn’t let on. I had to steady myself; I was buried in a very tight arsehole and wanted this to last as long as possible. Her orgasm ended, but she kept moaning loudly and consistently.

“tell me where my cock is?” I laughed.

“Fuck you!” she whimpered.

“Tell me right now where my cock is, or it will be going in and out very fucking fast.” I demanded.

I let it slide out all the way until just the head was in.

Kerry whimpered, I was holding my cock at the entrance to her arsehole ready to plough it deep inside if she didn’t obey.

“It’s in my arsehole, please, be gentle," she whispered.

I slowly sent my cock deep into her hole, I fucked her gentle until the timer went off.

“Ahh, that was okay, wasn’t it?” I asked.

As I walked around to the front of the bed again, her eyes were rolled back, and she had the bed sheet in her mouth, cumming again.

When this orgasm ended, she had a realisation.

“Is your dick going straight from my ass to my mouth?”

I looked down at her, our eyes met, and I waited for her next moan before slipping it in. Her eyes widened; there was no tongue action; she just held it in her mouth. This made me laugh. Then, once again, it was orgasm time. I felt her moaning on my cock, dribbling from the corners of her mouth. This time, she had her eyes scrunched shut in pleasure.

When this orgasm finished, she either forgot where my dick had been or didn’t care. She blew it like it was her last time.

After five rounds of this, she was in a constant state of orgasm. They lasted nearly a minute each before she’d come back down, only to start again ten seconds later.

I was still going slow in her ass, in and out at a delicate pace, but my thrusts were stronger, my body slapped against hers every time I planted my cock slowly into her ass.

“I can’t take this anymore. I’m weak. Please just cum soon, I beg you,” she muttered between moans and screams.

“Hold on tight, then. I’m going to have to up the pace if you want me to cum.”

“Do it. Fill my arsehole up,” she responded.

I’d been going at her ass for about four minutes, forgetting the timer. I was pounding away, not too hard or fast but enough to get me close. I could feel it building.

Then a monster orgasm came over her. She was wriggling and moaning so loudly I thought someone at reception might hear.

“Oh my god, I can feel your cock hitting the dildo. This is crazy. I’m crying. It’s so good but so sensitive.”

I grabbed her waist tightly and pounded against her; then, with a grunt, I slammed home and filled her arsehole with my cum. My cock twitched inside her as I emptied my load, I could feel her pussy tensing as I withdrew my cock from her arsehole.

I reached down and turned the dildo off, then the clit sucker. I gave her big round ass a good slap and grab.

“Good girl,” I said with a satisfied smile, knowing this was a night neither of us would forget.

She was done, emotionally, mentally and physically exhausted! I pulled my dick out of her arse; still hard, I walked round to her face and poked it into her mouth. She gave it a little swirl with her tongue, and I removed it. I leaned over her again, put my mouth to her ear,

“Imagine if the four people downstairs knew you’d just had your arsehole fucked and orgasmed to an inch of your life. Slut”

She smiled and blew me a kiss. I helped her up; after a short rest, we showered together. I got out of the shower first and saw her phone on the side. I unlocked it and sent a text to Gary, <I want you to fuck me hard when I get home, if you make me cum, I might treat you to a new hole!!!!>

“£3500 tonight, so you still owe me £8700. Was it worth it, slut?”

Before she could respond, she got a text. She looked shocked as she read it; she looked up at me.

“You prick,” she sighed.