chapter-six-pleasing-the-boss
ADULT BDSM

Chapter Six Pleasing The Boss

Chapter Six Pleasing The Boss

by cassioirl
19 min read
4.5 (5900 views)
adultfiction
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Riley was woken up by Addie who was wearing her therapist's uniform again. She looked around Basma's quarters groggily, but Basma was nowhere to be seen.

Her bedroom was in the corner of the tower and had windows on two walls. One gave a good view of the nearby sea. In the other direction, she could see the low buildings of the town they'd been visiting.

Addie pointed to a note on the bedside table, "I have a nice day planned for you here at the villa. Tomorrow, Farah will bring you to visit me and some of my slaves. B xxx"

Riley looked around the room, "I don't have anything here to wear."

"It ok. No one is around but me." Addie grinned. Riley thought she was enjoying her discomfort.

She followed Addie to the elevator and they descended to the ground floor. Riley tried to peek out of the elevator to check out the hallway before she stepped out.

Addie giggled. She walked out of the elevator and theatrically looked both ways down the hall.

"There no one here. It safe."

Riley stepped out and walked as fast as she could to her room. Addie followed her most of the way, then told her she'd see her later and left.

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Back in her suite, Riley checked her schedule. It was already nearly 10am and she was supposed to see the doctor at 10:30 and she was meeting Farah at 11 for brunch.

She quickly got dressed and ready for what she guessed would be another...intersection day at the villa. She had her quick doctor's visit then met Farah in the dining room.

Chef had a lavish spread of fruits and pastries laid out as well as cereals, juice and other choices.

The two women chatted over the meal and moved out to the veranda to finish their coffees.

"Sayyidah Basma needs you to do something today. She has a friend staying about an hour from here that she wants you to satisfy."

Farah sipped her coffee, avoiding eye contact with Riley.

"Oh. A...uh...a man?"

"Yes. I will ride with you to his hotel and give you some more instructions on the way."

Riley noticed there was no mention of additional money or veiled hints of rewards. Basma seemed to just expect her to do this.

"Ok. When do we go?"

"We need to leave in about 45 minutes. Finish your coffee. There's a gift bag in your room with an outfit for you to wear. I'll have the car ready out front when it's time to go."

Riley drank the rest of her coffee and headed quickly back to her room. It was probably better that she didn't have too much time to think about this.

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Riley was surprised with the outfit they'd left for her. It was a low cut and incredibly short black cocktail dress. The bag had matching black high heels, thigh high stockings and lacy underwear. There was no bra, but the diamond butt plug was left on top of everything else.

She put everything on and got her sunglasses out of her carryon bag, then met Farah at the front door and they headed off in the car. It was quite a contrast--Riley dressed in the sexy outfit while Farah wore one of usual business skirt suits.

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They rode mostly in silence until they got near the hotel.

"We arrive in just a few minutes. The driver will drop us at the main entrance.

You'll go upstairs to room 621 and knock on the door. You can stay for up to an hour--he'll be rating you, so be sure to leave only after 60 minutes or when you're confident he's satisfied. Meet me in the hotel bar afterwards and we'll head back.

You have your phone and I'll be in the hotel bar if you need me. Any questions?"

"Who's the...uh...guy?"

"A friend of Sayyidah Basma is all I know. I don't have any other details."

Riley nodded. It was the most casual sexual encounter she could imagine.

A few minutes later they arrived. They walked into the lobby together, but parted ways inside. Farah went to the bar while Riley walked to the elevators.

Riley felt conspicuous. Everyone else in the lobby was conservatively dressed. It seemed to be mostly a business hotel. Fortunately, it was early afternoon and there weren't many people about.

As instructed, she went up to the 6th floor and found room 621 and knocked on the door.

She heard a male voice call out, "it's open," and realised the door was slightly ajar. She took a deep breath and pushed the door open, trying to smile.

Riley was instantly shocked to her core. Sitting in a chair at the far end of the room was her boss, Stewart. He looked startled, but quickly looked at her from head to toe.

"Well, well. That's quite a transformation...and in less than a week."

Riley was mortified. It was one thing to experiment with people she'd never see again. But, this was her life, her job. She'd never been attracted to Stewart and had actually thought of him almost like an uncle the way he'd seemed to look after her at work. She also knew for a fact that he was married--she'd met his wife at the Christmas party.

She tried hard to compose herself but could barely speak. Her heart pounded in her chest and her stomach was in knots.

"Hi, Stewart. I didn't expect to...um...see you here."

"I had business in the area and asked Zahir how you were doing. He gave me an update and suggested that we meet." He had a lascivious grin that made her skin crawl. He'd never looked at her like this before.

"Oh, right." Riley stood unsteadily, she could feel herself blushing with embarrassment as he openly eyed her up, "I'm ok. Farah is looking after me."

His grin grew wider, "so I was told. When Zahir told me what you'd been doing here, I didn't believe him. So, he said I should come see for myself."

"Ok." Riley wanted to be anywhere else than here.

"So, are you going to show me?" Stewart said as he stood up. Riley could see the bulge in his trousers.

"Um...uh...what did..." Riley's voice trailed off. She didn't want to say anything. Anything she did would just make this more...real.

"Well. You just walked into the hotel room of a person you didn't think you knew. Dressed like that--" he waved his hand at her for emphasis as he walked towards her. "I'm guessing you had some idea what was going to happen here."

"Yeah...well..." her voice was barely a whisper.

"Let's have a look at you. Turn around so I can see that dress."

Riley mechanically complied. She awkwardly turned around for him in a small circle as he openly ogled her, exaggeratedly looking at her from head to toe. She'd never felt more like a piece of meat than she did now. Even the presentation the other night was somehow not as bad as this.

"Now, come over here and bend over the bed."

"Stewart, you don't have to--"

He cut her off, his voice firm. "Now, Riley. My understanding is that whatever I tell them about this meeting has...certain ramifications for you. So, you can leave here with me being happy or disappointed. What's it going to be?"

Riley started to say something, then stopped herself. This was worse than anything they asked her to do. She thought about leaving--just going home. But, she figured she'd be giving up a lot of the money. She could do this. She'd have enough money in a few weeks that she wouldn't have to go back to work for Stewart ever again.

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"Ok," she said, resignedly.

Stewart grinned ear to ear as she walked over to the bed near him.

She bent over the bed and was startled when he spanked her ass. She cried out slightly in surprise. It only stung a bit, but it was so unexpected.

He chuckled behind her then spanked her several more times through her dress.

"Hold still." He flipped up her dress onto her back, then roughly pulled her panties down and helped her step out of them.

He patted her butt with his open palm, "such a nice little ass you have, Riley. Just right there for me to enjoy."

She heard a funny sound behind her. Then he hit her with his belt. The leather stung hard and made a loud "whack" noise as it landed.

"Oomf. Fuck."

He gave her another 10 stinging spanks. It hurt, but wasn't unbearable. When he stopped, he threw his belt to the floor and gently rubbed her ass, feeling the welts the belt had made, laughing softly.

Then he reached between her legs, roughly spreading her thighs then sliding a finger easily inside her.

"I never would have guessed this kind of thing would get you off, Riley. Mack and Sarah and the gang wouldn't believe me if I told them. Oh...and what's this? You're wearing anal jewels now."

She bit her lip. She didn't want to say anything to give him anything else to use against her.

"Now, take that dress off."

He sat down in the chair to watch.

She stood up and turned around. She tried pleading with her eyes, but his expression remained cruel and he wasn't looking her in the eye.

She unzipped the dress and slipped out of it, then slipped the heels off. She was left naked apart from the stockings.

When she'd finished, he removed his shoes and trousers and tossed them on the floor. Then stood up, his cock obviously hard in his boxers.

"Now, get over here on your knees and show me what you can do with that mouth of yours."

Her skin crawled. He seemed to enjoy making this as uncomfortable as possible for her.

She stepped near him, then kneeled down. His hard on was hovering near her face. She reached out and pulled down his boxers, releasing his cock.

She reached out and took hold of it in her right hand, cupping his balls in her left hand and began gently licking him.

"It's always the quiet ones. You really know how to suck a dick, Riley."

She tried to ignore him and just focus on his cock. She took the tip in her mouth and gently bobbed on it, using her hands to stroke his shaft.

"You're probably wondering what my wife Gwen would think. Well, if she were here right now, she'd either be on the floor next to you or waiting her turn."

His words just made her feel worse. Like she was just a thing to be used. Why was she doing this? She should have left before this happened. Focus on the money. Focus on the money.

"I'll have to ask Zahir if Mack could have a turn. Or maybe Sarah? I'm about 90% sure she's a lesbian. Maybe you're her type?"

Riley felt her face burning red. She began going faster, wanting him to cum so this would be over.

Suddenly he grabbed her head and held it in place, fucking her mouth with a few deep strokes. Then he pulled his cock out and blasted his cum all over her face. Riley closed her eyes as the cum landed on her.

When he was done, she started to reach for a tissue from a box on the desk.

"No. Leave it there. I like seeing you like this." He laughed again, making it even worse.

Stewart got into the bed and had Riley join him. He needed a few minutes to recover and spent his time exploring her body. He seemed fascinated by the piercings and the fading henna tattoo on her back.

Riley kept checking the clock, wanting the hour to pass.

"So what's this then?" Stewart tapped the diamond encrusted head of her butt plug.

"Is it what I think it is? Is cute wholesome Riley wearing a butt plug?"

"Yuh...yeah."

"Wow. I would never have expected that."

He had her roll onto her stomach and gently separated her ass cheeks for a better look. She felt totally exposed, laying like that in front of him.

He gently but firmly pulled the plug out. She felt her ass expand then relax as it was removed leaving her with that sudden feeling of emptiness. He slid a fingertip inside her ass then removed it, wiping the lube off in the back of her thigh.

"Have you ever been fucked in the ass before?"

"N...no," apart from this plug, she'd never had anything...back there. It repulsed her to think Stewart wanted that.

"Lucky me. I'll get to pop your ass cherry and be your first."

"Please don't, Stewart. I've never done that before."

He laughed again, relishing her discomfort.

"Did you bring lube?"

"Yes. They gave me some...it's in my handbag."

"Get it."

She crawled out of the bed. She wanted to cry but somehow held it together. She didn't want to give him the satisfaction of seeing her sob.

She got out the small tube of lubricant Farah had given her on the ride over. Farah had implied she might not be wet enough for sex...but hadn't mentioned anything about her ass.

Stewart got out of the bed and had her bend over it like before when he spanked her. He took the lube and slathered it on his cock and around her ass, slipping his lubed finger inside her.

He got behind her and placed the head at her asshole and pushed. She groaned at the initial discomfort, but bit her lip and struggled not to cry out.

After he was inside her, he began slowly thrusting in and out of her ass with long, deep, steady strokes. Fortunately for Riley, he didn't last long. He pulled out his cock and came on her ass. She could feel his cum dripping down the cleft of her ass.

He wiped his cock on her ass cheek and sat down on the bed, breathing heavily. She turned around and sat on the bed next to him pulling the covers over her as best she could. Her ass felt a bit sore from his cock.

"Well, it looks like my time is almost up." He put on a hotel robe from the closet and handed Riley a bottle of water.

She took a sip and started to get dressed.

When she had her clothes on, Stewart picked up his phone and read a message. Then he opened an envelope with his name on it that had Omani money and counted the contents.

"So, our friend Zahir wants me to rate your performance with cash. So, this is for you."

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Stewart handed most of the money to Riley--450 Omani rial--and kept a 50 rial note that he put into his wallet.

"Hopefully, I'll get to see you again real soon."

"Goodbye, Stewart," Riley tried to be as neutral and calm as possible. Inside she wanted to cry or vomit after what just happened.

She left his room and got quickly to the elevator. She had put on her clothes as quickly as she could and hadn't looked in a mirror. She now saw herself in the reflection of the elevator walls and she was a mess. Her hair was disheveled and her makeup was smeared and streaked. She didn't think it was noticeable, but she could make out where his cum had dried on her face.

Riley stepped out into the thankfully still mostly empty lobby. Farah had been waiting nearby and joined her, escorting her quickly outside to the waiting car.

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In the car, Farah handed Riley a blanket and she curled up into it. Neither woman said a word for a long time. Riley was still processing what just happened.

On the one hand, she thought it was horrible what Farah and Zahir had made her do. But, Stewart had taken full advantage of the situation. He wasn't a reluctant partner--he'd actively participated and actually made things worse than they could have been. If he hadn't wanted to use her like that, he could have simply not agreed to be there at all. They'd dangled her as bait in front of Stewart and he'd pounced.

After a while, Farah handed Riley a refreshing fruit juice and a warm washcloth. Riley wordlessly wiped her face. The warm cloth felt refreshing. That little thing helped her feel more human. She sipped the drink. She could taste a faint hint of alcohol in it and was happy it was there, hoping it would help steady her nerves.

"Why did you make me do that?"

"It was Sayyid Aziz who arranged this. I don't know why."

Riley realised what a plaything she'd become. She felt like a marionette with a lot of strings and several puppeteers.

"I have to ask you. How much money did he give you?"

Riley reached into her handbag and handed the cash to her. Farah quickly counted the nine bills then handed the money back to Riley. She sent a message to someone, then put her phone away.

Riley had thought the money was just to make her feel like a whore. But, there seemed to be more to it.

"What does the money mean?"

"He was asked to rate you using money. Sayyid Aziz gave Stewart 500 Omani rial and told him to give you the money based on how pleased he was with you. He gave you 450."

She nodded. Riley wasn't sure how to take that. It was like 4.5 stars out of 5. It made things even more humiliating somehow to know her "performance" was rated by...him.

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They arrived back at the villa late in the afternoon. Riley practically ran to her room to change out of her clothes and take a long, hot shower. She scrubbed herself clean using lots of extra soap, then made herself a strong sea breeze cocktail from the bar in her room.

Farah messaged her. She'd arranged for Addie to give her a massage in the spa whenever she was ready and invited her to join Farah for dinner. She wasn't mad at Farah and agreed, wanting some company.

Riley went down to the spa. Addie was alone and greeted her with a long hug.

"You ok?"

"Yeah. It was such a betrayal. I thought he was a decent guy. He was...horrid."

Addie just nodded. She helped Riley onto the treatment table and gave her a slow, deep tissue massage. Afterwards, she had Riley relax in the chill zone and brought her another strong drink.

After a while, Riley felt a bit better. Addie kissed her tenderly on the lips.

"You come stay with me tonight? Nothing sexy. Just relax."

That actually sounded nice, "ok."

"I come get you at 8. Ok?"

Riley smiled and nodded.

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Chef had another amazing meal for them. It seemed to be a mix of North African dishes which were light and tasty.

The two women chatted amiably, both seemingly avoiding talking about what happened earlier.

"Sayyidah Basma wishes to see you tomorrow."

Riley's heart skipped at the sound of her name. "She's coming here?"

"No. She has another residence nearby. She wants you to meet some more of her...special friends. Like Addie."

"Oh." Riley hadn't really thought about Basma having a harem of...what was Addie? A slave? Girlfriend? Something else?

"Sayyidah Basma does very...extreme things with her special friends. I think what you will see tomorrow may...surprise you."

"Does she...force them to do things?"

"No. She's very skilled at learning what people...crave. Then she helps them to do those things."

Riley blushed. Was Farah implying that she "craved" what they were making her do?

"For me, it's just about the money. A few weeks of...of this...and I'll be able to have a much nicer life. A nice house..."

Farah nodded.

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Riley was only in her room a short while when there was a knock at the door. Addie was standing there, wearing long pink pyjamas.

"You ready?"

Riley smiled. It was cute and kind of funny to see Addie dressed this way.

"I'll change."

Riley dug some of her own pyjamas out of her luggage and quickly put them on.

While she waited. Addie put a few snacks and drinks into a bag to bring along with them.

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They headed upstairs to Addie's rooms. They were beautifully decorated with pictures and wall hangings. The walls were different colours in each room in stark contrast to the mostly white or muted palette of the rest of the villa.

Similar to Riley's suite, Addie had several private rooms. She told Riley she enjoyed cooking, so she tended to cook for herself rather than get meals from Chef.

Addie pulled out a couple of light blankets and the two women got comfortable on the oversized couch. Addie put on a new action movie as they chatted, snacked and scrolled on their phones.

After awhile, Addie ended up snuggled against Riley on one side of the couch. It felt nice to have a warm body just relaxing next to her. Addie was laying across her and Riley had her arm gently around her friend.

"I'm supposed to meet some of Basma's other...special friends...tomorrow."

Addie laughed, "yes, she want you to meet two of her other slaves. She have many houses and you will see her main house where she is most of the time."

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