A Deal You Cant Refuse

The Boss's Proposal: A Deal You Can't Refuse

Fuck! Kayla hissed as she received yet another letter with her least favourite word on it - "Dunning". She had been behind on her payments for almost five months now. Working a second job next to her main one was close to impossible due to the crazy working hours she had to endure.

She needed a raise or a miracle if she didn't want to get evicted soon. Thankfully her landlord was a very understanding and patient old man. Two characteristics her supervisor was unfortunately missing. Lilah Lawson was extremely demanding, adamant and always in control.

When she arrived at the office that day, she knew that she would have to have a very uncomfortable talk. As if employee reviews weren't stressful enough already.

"Ready when you are, Morgan," Lilah barked, when she walked past Kayla's booth, not even bothering to stop or look up from the papers in her hand.

Kayla quickly gathered the paperwork she had prepared and rushed after her boss.

The first few minutes were quite tense, as Lilah went over her successes in recent projects. The numbers could speak for themselves - all in all, she had done a very good job this year, which gave her the necessary confidence to voice her demands.

"A raise?" was the first response she got, combined with an unconvince raise of Lilah's eyebrows. "Well, considering it was a very tough year for our business, I'm afraid my hands are tied. We can, however, revisit the topic in the second half of the year."

"I am a hard worker and my results clearly show that. With all due respect, I deserve my salary to reflect my successes."

"You deserve?" Lilah's mouth turned into a lopsided grin. "Well, you don't always get what you deserve and sometimes, that might actually be a good thing."

"You don't understand," Kalya grew frustrated. "I need that raise."

Lilah tilted her head and watched her intently.

With a low sigh, she admitted: "I can hardly pay my bills as it is. If I don't get a raise, I might not be able to afford my flat in the future."

"I see," Lilah said and leaned back. "Well, I can't officially offer you a raise. But I might be able to work something else out. What would you be willing to do as extra tasks?"

"Anything," Kayla blurted out. "I will even wash the dishes in the coffee corner, if it will help me earn some extra money."

Lilah smiled a devilish smile. "Well, in that case, I will come up with something. But it will require some overtime and you mustn't mention this to anyone else."

"Of course," Kayla answered immediately.

"Perfect, come to my office tomorrow at 7pm."

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Kayla's stomach tightened with nervousness. It was half past six and the office was almost entirely empty. She hadn't stayed this long in a while, but realised that she quite liked the calm atmosphere of this late hour. She was surprisingly productive and hardly noticed how time flew by.

When the last colleague left and bid her a good evening, the clock on her desk showed that it was five to seven. The light at her desk was the last one that cast a soft gleam into the otherwise dark office, besides the one in Lilah's room.

With slightly shaking legs, she wandered over to the glass door with the golden letters "Lilah Lawson". She knocked three times and entered when she heard Lilah's muffled voice.

"Kayla, come in and sit down. I'll be with you in just a second."

Lilah's office seemed almost cozy, the old vintage lamp on her desk emanated a soft glow while the dark wooden floor gave it an earthy feel. Lilah finished her work and set a heavy folder aside, before standing up and closing the blinds as well as locking the door.

That made Kayla a bit nervous, but then again, she said that this raise would not be official, so she probably just didn't want anyone snooping around.

"As promised, I found a way for you to earn some extra money. And it has nothing to do with dirty dishes," she winked at her and a shiver of curiosity ran down Kayla's spine.

Lilah reached into one of her drawers and to Kayla's surprise pulled out a small butt plug with a post-it that read "50$". Her eyes grew wide and she looked at her supervisor in shock. She could not be serious.

After a few seconds of Kayla's stunned silence, Lilah grabbed a second butt plug from the drawer. It was slightly bigger and its post-it read "100$".

"Shall I continue?" she asked calmly and studied Kayla's reaction.

Kayla could hardly believe her eyes. Was this the offer she thought it was? A third plug appeared and her eyes dashed to the post-it: "150$".

"You can leave anytime, you know that?" Lilah asked when Kayla still didn't say anything. "I will not force you to do anything you don't want to do."

Kayla swallowed hard but nodded in understanding and Lilah pulled two more plugs out of her drawer - "200$" and "300$". Her eyes widened at the sight of the last one. It was huge.

But Lilah added one more on top: a strap-on. Even though it was smaller in diameter than the last plug, it made up for it in length. The post-it read "400$".

"I told you I couldn't officially offer you a raise" Lilah began, "but I can offer to pay for my personal pleasure."

Kayla starred at the plugs. Nothing could have prepared her for this. But she really did need the money or she could wave her apartment good-bye. If she wanted to pay-off her debt, she would need at least 300$.

She definitely could handle the first two plugs, as she was no anal virgin, and maybe even the third one, if she managed to relax enough. For the others, she had her doubts -- but there was only one way to find out.

"I will do it," she said huskily.

"Perfect," Lilah said in a low voice. "Lose the blouse," she ordered without missing a beat and it took Kayla a few seconds to stop her fingers from shaking.

She was nervous, that much was obvious, but she still managed to undo her buttons.

"Now the bra." She heard Lilah say and reached behind to open the clasp.

Her nipples stood on edge in the cool air of the room.

"Come here," Lilah commanded and stood up from her wooden desk.

Kayla stepped in front of her and Lilah's wandering eyes examined her naked upper body. When she came closer and Kayla intuitively retreated, the wooden edge of the desk pushed against her upper thighs. Lilah grabbed Kayla's breasts in her hands and kneaded them, pinching her nipples between her fingers. A soft moan escaped Kayla's throat and she blushed.

"Turn around," Lilah told her and when Kayla did, she felt how she was being pushed down onto the desk. "Reach for the corners with your hands and keep them there, unless I say otherwise."

She did as she was told. Lilah pushed up her skirt und with quick fingers, grasped the thin fabric of her string and pulled it down. Kayla stepped out of it, careful not to move her hands. She had to admit, this was rather exciting.

"Spread your legs," she heard the next order and obeyed instantly. "What a view," Lilah murmured and playfully slapped one of Kayla's cheeks, making her jump in surprise. "I want you to address me as 'Mistress', when you talk to me, Kayla."

"Yes," Kayla said and quickly added "Mistress" when a harder blow hit her behind. Her heartbeat quickened. Did that slap just arouse her?

"We will start slow," Lilah explained as she caressed Kayla's ass. "Have you ever had anal before?"

"Yes," she answered, forgetting the "Mistress" again. But the next blow quickly reminded her. "Mistress," she breathed.

"Good, then we can skip the first one, don't you think?"

"Yes, Mistress."

Kayla heard the small clicking sound of a bottle and felt cool, wet lube gliding down between her cheeks. Then she felt warm and soft fingers trailing up and down her crack, distributing the lube all over her soft tissue. A probing finger started to push against her entrance and she took a calming breath, trying to relax.

The pressure increased and her anus widened to allow the slim finger to slip inside her. She moaned at the sensation and tried to relax even more. The plugs surely wouldn't be as easy going.

It made her shiver slightly when Lilah finally reached over her to grab the second plug, touching her bare ass with her hips. She slowly moved the plug up and down, spreading the lube on the toy. Then she positioned it right at her entry and slowly increased the pressure.

Kayla could feel how tight her anus was, her nervousness making it almost impossible to relax. But Lilah's constant prodding with the plug slowly opened her reluctant asshole. Finally, her soft tissue widened enough to allow the plug in and she moaned in surprise when she felt it slip deep inside her.

"Now look at that. Someone's ass is hungry for more," Lilah mused and slapped her ass again, before slowly pulling the plug back out.

She grabbed the third one, pushing Kayla against the cool wood of the table in the process. With her hand she distributed the lube on her butt before rubbing the plug over her sensitive anus. Kayla took a deep breath and she could feel how some of the tension left her.

The wetness between her legs built up as her arousal increased. The cold metal against her behind send a shiver through her body and she tried to relax even more, when she felt it slide up between her cheeks. Slowly and steadily the pressure increased and her ass stretched to take in the plug.

Her heart was pounding in her chest and the excitement had her spiralling. At the widest part of the plug, Lilah hesitated for a few seconds, fully exploiting the moment when Kayla's anus was stretched before slowly letting it sink in. She groaned in pleasure and pushed her hips up slightly.

"You are such a good anal slut, aren't you?" Lilah asked and caressed her buttock before slapping it again and slowly removing the plug. Kayla mourned the absence of the plug and the feeling of emptiness it left behind. Feeling full and stretched had been a real turn on for her. Her nervousness was completely forgotten.

"If think we can go even bigger," she heard Lilah say.

"I don't know if I can, Mistress," she admitted.

"Let's find out."

Even more lube ran down her buttock und she could feel Lilah's fingers circling around her butthole and pushing into her. She bit down on her lip and groaned quietly as her fingers stretched her tight butt hole. Then she felt the plug again. It pushed her cheeks apart before it was even close to her anus.

"I might need your help with this one," Lilah said, "Spread those cheeks for me."

Kayla moved her hands to her buttocks and slightly pulled them apart.

"More" Lilah instructed and grabbed Kayla's hands with her own, pushing her cheeks apart. It almost hurt when she stretched them as far as she could and Kayla grunted at the slight discomfort.

The tip of the plug pushed against the now completely unprotected rosebud and caused another moan to slip out of her lips again. She felt the pressure and how her anus widened as the plug was pushed in deeper and deeper. The pain and pleasure drove her mad.

"Almost there," she heard Lilah's voice. "Relax."

She tried to but the constant pressure of the huge plug made it hard. She didn't know if she would be able to take it. It felt as if her ring would rip any second now.

"Aahh," a small cry came over her lips when her anus was stretched almost painfully wide.

"Good girl."

Lilah increased the pressure even further and a painful, yet arousing rush of overwhelming sensations overcame her, when she felt how the plug sank into her. Her sore anus needed a small break and she was thankful that Lilah allowed it.

"Now, are you satisfied with your raise? Or do you want more?"

"I can't go any bigger, Mistress," she almost sobbed.

"What about the strap-on?"

"Yes, Mistress. I think I can do that."

"Good girl," she mused again, as she started to fasten the straps around herself. "Get up on the table and lie down on your back."

With weak knees and a sore ass, Kayla shifted and straightened up, before turning around and sitting down at the edge of the table. The contact pushed the plug even deeper into her tight walls and she whimpered.

Slowly, she leaned back until she felt the hard surface of the table against her back. Lilah's firm hands gripped the soft flesh of her thighs and pushed her legs up, making her wince.

"Hold your legs," she ordered and Kayla hooked her underarms under her knees. "Spread them wider," she heard another command and tried to pull her legs even further apart.

Then it was time to remove the huge plug again. Kayla took a deep and steadying breath, expecting another wave of pain. It only hurt a little but the relief afterwards was worth it. However, before she even had time to calm herself a little, she already felt the strap-on push against her sensitive spot.

"Someone seems to really enjoy this," Lilah mused and let one of her fingers trail in-between Kayla's wet labia, making her shiver and moan.

Then she slowly inserted the strap-on into Kayla, filling her tight tunnel and pushing her legs apart with her own hands. It glided in easily, as Kayla was already stretched and more than ready to take it in. Once she had buried the strap-on deep inside her, she slowly pulled it out again, eliciting a groan from Kayla.

Then Lilah began fucking her tight ass in a slow rhythm. As Kayla relaxed, Lilah picked up the pace. The slight burn at her entry mingled with pleasure. It felt amazing. Kayla started to moan and she could feel how her pussy started pulsating with arousal.

Lilah retreated with the strap-on and pulled Kayla up from the desk. She turned her around by her shoulders and pushed her back down on the table, before she could even say anything.

She pushed the strap-on back in and Kayla moaned at the sudden reinsertion. Lilah fucked her hard and relentlessly into the table. When she pulled her up the next time, her fingers found Kayla's wet slit and started fingering her.

The overload of sensation made Kayla cry out in pleasure and her legs started shaking. Her arousal was dripping out of her soaking cunt and it didn't take long until she felt how an intensive orgasm was approaching.

"Fuck, this feels too good," she groaned. "I'm about to come."

"Not yet," Lilah hissed into her ear. "Only when I allow it."

"But," Kayla started whimpering. "I don't know if I can hold it any longer," she sputtered.

"Hold it or you will regret it," Lilah threatened and the menacing tone of her voice made Kayla flinch.

With all her might she concentrated on not coming, but the relentless torment between her legs made it almost impossible.

"It's too good," she whimpered. "I won't be able to hold it in much longer."

"Don't you dare come, Kayla," Lilah warned. "Don't you dare."

"Please, please," Kayla writhed under her touch. "Allow me to come. I'm begging you. Please."

Her words were almost incomprehensible.

"Kayla," Lilah murmured into her ear. "Now you can come."

As if she had flipped a switch inside Kayla, an earth-shattering orgasm crashed over her like a wave and she cried out in pleasure and relief. Her moans echoed in the office and as her legs gave out. She sank forward and onto the table again. Lilah slowly stepped back and pulled the strap-on out.

"Congratulations on your raise, Kayla."