The Challenge: Ch. 02

Literotic asexstories – The Challenge: Ch. 02 by Cassioirl,Cassioirl
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Chapter 2

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The interview the next day was a disaster. The three person panel had been arrogant and condescending. Cassie felt like she was back in college trying to defend herself about a badly written essay.

The panel acted as though every answer she gave was wrong and their follow up questions made her feel even worse.

When the goodbye handshakes came, she knew she wouldn’t get an offer.

She practically ran out of the building. She started walking back to the hotel and saw a quiet bar and went inside, texting Val to see if she could join her.

———-

Cassie sat in the dimly lit, dingy bar drinking a double gin & tonic with almost no gin. She felt so stupid. She’d really let herself down in the interview and now the whole trip was for nothing.

She was still crying a bit, fighting to stop. She didn’t want Val to see her like this. On top of everything else, she felt like she’d let her friend down after Val had gone to all the effort to get her this opportunity.

“Hey, hey…don’t cry Cass…just breathe.” Val had sat down next to her and was patting her gently on the back.

“I really fucked up the interview…I’m so sorry Val.”

Val gave her a weak smile. “It’s ok. Those guys can be assholes.”

Val ordered a drink for herself and Cassie recounted the interview, saying what she should have told the panel as she gave every question a detailed post mortem.

Val let her vent and talk through all the details over three rounds of drinks. Cassie got to the end and the two of them sat quietly for several minutes.

Val finally spoke. Her voice seemed very flat and almost monotonous.

“So, the interview wasn’t a complete disaster.”

“Huh?”

“Bradshaw liked you.”

“What? He wasn’t even there?!”

“He was watching. The conference rooms we use for interviews all have cameras and mics for legal reasons. Bradshaw often watches interviews just to see what kind of people we’re talking to.”

“And?” Cassie felt cold, her skin seemed to go clammy.

“I told you about his side projects. Some of them are a bit…um…unorthodox…he likes to challenge people, asking them to do things for money.”

“Like prostitution?”

Val chuckled humorlesy.

“He’s worth billions. He could fly 10 girls here on his jet who’d do pretty much whatever he wanted them to. That kind of thing doesn’t interest him. To him, it’s more about the challenge of pushing people to do things they wouldn’t normally do.”

Cassie’s brow furrowed as she tried to make sense of what Val was telling her.

“Like Squid Game or something?”

Val laughed. “Like that…but no one gets killed. Or injured or anything. He pays for everything and his people make sure nothing permanent happens.”

“Is that…is that even legal?”

“Borderline. There’s contacts and NDAs…but some of them would probably fall apart in court.

“And he pays people to do that? To do his challenges?”

“Yeah.”

“How much?”

“For a year of challenges, if you do everything. You get $1 million. He’ll figure out the taxes so you actually get more and end up with $1 million in the bank.”

“A YEAR? Fuck…”

“It’s not all day every day. You’d be off one week each month and not every day has a challenge.”

“What if someone fails? Like you get to week 51 and fail, do you just get nothing?”

“He pays for everything during the challenge so it doesn’t cost you anything to participate. You get $10,000 into your bank account up front and after each week. So, if you bail after 3 weeks, you still walk away with $40,000.”

“Whoa. That’s unreal. Has anyone done this?”

“Not the exact challenge he has in mind. He had this elite athlete who did a series of physical challenges and a criminal who did something like this but with crime.”

“Oh. So the challenges are all…around a theme?”

“Yeah.”

“What…uh…what them does he have in mind for me?”

“Sex. Basically like a crazy sex odyssey. Anything you can imagine plus plus plus.” She took a sip of her drink, punctuating her last statement.

Cassie’s stomach sank. She wasn’t a slut or a super kinky person…could she even do this?

“I don’t think I’m the right person for this…I mean…you know me…” her voice trailed off as her brain seesawed between the money and what she might be made to do to get it.

“You’re exactly the right person. The person who could do this easily wouldn’t be interesting. The fact you didn’t just say yes means you’re the kind of person he wants.”

“But like…what are the boundaries?”

“Nothing illegal or permanent. At the end of the year, you’ll be returned to how you are now. You’ll never be at risk–his people will watch over you.”

“So…people will be like spying on me?” She was blushing at the thought of strangers watching her have sex. But, she also was surprisingly a little excited as well.

“Anything that’s a challenge will be filmed so Bradshaw can verify you held up your end of the deal–”

“Whoa–I can’t–”

Val held up her hand. “He’s rich. Nothing will end up in the internet. You’ll have a contact automatically giving you another million if it did. So, you’re protected. He also keeps his security team in line with some…unconventional methods. They’re 100% reliable.”

There was a couple minutes of silence as Cassie thought through things.

“Why didn’t you do it?”

Now Val blushed. “I kind of did. I did an earlier version of his challenge…it…paid for my penthouse and he promoted me to this team after as a reward.”

“What kind of things did you have to do?”

Val looked like she was going to answer, then stopped herself.

“I…uh…don’t want to get into it. I’m not going to lie–I enjoyed most of it. There were only a few times I felt I had to just power through. It does change you though. I found myself…craving some thing afterwards. It…opened doors that had never been opened before. You learn a lot about yourself on some really new and different levels.”

Val’s voice trailed off and the two friends sat silently again.

“Ok. I’ve got nothing to lose and I need the money. What happens next?”

“You’ll have a short meeting with Brasdshaw tomorrow and sign some papers. Then it begins.”

Cassie’s stomach sank. But, she also felt herself getting wet in anticipation and she felt a throb of excitement.

———-

It was a strange night and Cassie’s dreams were filled with a strange mix of fantasies and some moments of terror.

She was up early the next morning. As instructed by Val, she did up her hair and makeup perfectly and put her interview suit and heels back on.

It was 8:45am on a Saturday and downtown Austin was deserted as she walked the short distance to the company’s building.

She entered the revolving door, feeling the cold air conditioning on her skin. Her footsteps seemed to echo loudly on the marble floor as she made her way to the security point next to the elevators.

“Good morning. I have an application to–”

“Hi. Are you Cassie?”

“Yes.”

The security guard handed her a lanyard with a key card.

“They’re expecting you. 10th floor.”

“Thanks.”

She tapped the keycard and the metal gates opened for her. She walked the dozen or so steps to the elevator and headed upstairs.

The elevator doors opened to a professional looking reception area. Val was standing there waiting for her dressed almost identically to how she was when she picked her up at the airport what felt like a year ago.

“Hey.”

“Hey.”

“You ready?”

“I think so.”

“Ok. Follow me.”

Val walked purposefully down the carpeted hallway, leading Cassie past empty offices and meeting rooms. At the end of the hall was a wooden door with a nameplate reading “K. Bradshaw, CEO and Chairman of the Board.”

Val knocked once, then pushed open the door waving Cassie to enter.

Cassie took a deep breath and stepped in, trying to smile and look confident despite her racing heart.

She wasn’t sure what she’d expected. They’d googled Bradshaw, but had expected him to look older. He could pass for late 30s, but she knew from his bio he was 48.

Despite the early hour on a Saturday, he was wearing a suit and tie and looked perfectly groomed. He sat behind his massive dark wooden desk, laser focused on her. Cassie felt like he was scrutinising her head to toe.

“Good morning, Cassie! I’m pleased to finally get to meet you.” He stood up awkward and almost robot-like and shook her hand. He didn’t smile and his look remained neutral and impassive.

“Good morning, Mr. Bradshaw.”

“Val tells me she’s told you about our challenge and the general terms.”

“Yes.”

“Good, good. And what do you think? Would you like to participate?”

“Yes, sir. It sounds…like a…uh…good opportunity.”

“It is. Life changing money.”

He leaned back slightly in his chair and opened a desk drawer. He lifted up a stack of $100 bills with a paper band holding them together indicating it was $10,000.

“I like to give the first payment in cash to show I’m serious and so you have something tangible as we start doing business together.”

He slid the money across the desk towards Cassie. Then he lifted two folders and set them next to the cash.

“These are the contracts we need you to sign to get things started. I’ll give you 15 minutes to go through them. If you’re happy to sign them, then we can begin.”

He set an expensive looking gold pen on top of the folders and stood up leaving the two women alone in his office.

Val stepped over and spread out the contents of the folder on the table. It was six short legal documents; two copies of each.

“This is a standard NDA…this one outlines the payment terms…this is your privacy guarantee…this one is the guarantee the company will look after your wellbeing and no permanent damage…this is the release to film and record you for personal use by Bradshaw and this last one is basically the rules of the challenge. Take a quick look and see what you think.”

Cassie scanned the documents as best she could, peppering Val with questions. The gist of it seemed to be like porn contracts–sex for entertainment rather than prostitution. Fortunately, she’d dealt with contracts, so it wasn’t as daunting as it could have been. But, given the nature of the challenge, she wondered if much of these would be valid in court.

She signed all of them with Val–conveniently a notary–was able to witness and stamp each one. Val separated the documents, putting a copy of each into both folders.

Val was standing, leaning over the desk stamping the last paper when Bradshaw returned exactly 15 minutes later. The chunk noise as he opened the door made both women jump from the sudden noise in the otherwise silent office.

Bradshaw didn’t say a word, but walked back behind his desk and sat down. Val stood almost to attention as he passed.

“Is everything in order, Val?”

“Yes, sir. Signed and witnessed.”

“Perfect. These are yours Cassie.” He set down one of the folders next to the money.

Cassie picked them both up and put them into her handbag, bending the folder to make it fit.

Bradshaw stood up and walked over next to Val.

“Stand up for me, Cassie.”

Her heart skipped a beat.

She stood, her legs felt like jelly. Her faces burned with embarrassment.

“Take off your jacket. Let’s have a better look at you. Let me see what I’ve bought.”

Cassie swallowed and tried to keep her composure. She fumbled as she undid the three jacket buttons then removed the jacket and awkwardly draped it over the back of the chair.

She was wearing a white button down top and the dark grey skirt matching the jacket. She held her hands together in front of her. She couldn’t bring herself to make eye contact, so was staring at his chest.

He looked at her for what seemed like ages, leaning slightly side to side as though sizing her up from different angles.

“Unbutton your top.”

Cassie’s hands were trembling a bit. She was humiliated. She’d actually sold herself to this guy. Was she a whore?

She unbuttoned her top slowly–more to keep her composure than anything else. She felt herself getting wet. How could this be exciting her?

He stepped over to her and opened her top, brushing the hanging material aside to reveal her breasts, held snugly by a sports bra.

He pulled up the cups, exposing her chest, but leaving the bra awkwardly above it. He took her breasts in his hands, cupping them gently as though weighing them and teasing her nipples with his thumbs.

“Very nice, Cassie…lovely.”

He let go, stepping back again, his eyes still focused on her boobs.

He walked to the side of the office and sat down onto a dark leather sofa.

“Cassie, take off your top and bra. Both of you come here.”

As Cassie complied, Val walked over and stood next to Bradshaw. Bradshaw locked his gaze with her, smiled slightly evilly and reached up under Val’s skirt.

“Your friend is well trained. I didn’t give her any instructions this morning for our meeting. But, she arrived perfectly dressed and without underwear–exactly as I like her. And, her cunt is recently waxed. And wet.”

He removed his hand and made a show of wiping her juices onto a handkerchief he pulled from his jacket pocket.

“Cassie, kneel over here in front of me. Val, get me ready for her mouth.”

Cassie got down on her knees in front of him. She could feel her heels against her butt. The room suddenly felt cold…but she was pretty sure it was just her discomfort and humiliation at being topless and about to suck off a guy she’d barely met.

Val sat down next to Bradshaw on the couch. She leaned over and unbuckled his belt and unzipped his slacks. He lifted himself up slightly enabling her to pull down his pants and boxers.

She took his hardening cock in her hand, expertly teasing his cock and balls with her nails. She knew what he liked and with a few quick movements with her nails on his sensitive skin, he was fully erect.

“Cassie?”

Cassie glanced at Val who gave her just the subtlest of nods as encouragement.

She moved forwards on her knees towards Bradshaw and took his cock in her right hand. She parted her lips and tentatively licked his shaft with the tip of her tongue.

His breathing quickened in response and she became aware of the heady scent of his cologne.

She’d given head to a few guys when she’d gotten as far as the bedroom and then decided she wasn’t really interested. She tried to put herself in that same headspace–to just focus and get this over with as quickly as she could. And yet, the whole situation was exciting her.

Being used like this and seeing her friend ordered around and roughly, casually being touched made her throb. She was very wet.

She leaned forward and tentatively began licking his shaft, moving up quickly to the head and then taking his cock in her hand.

“Val?” Bradshaw nodded at her friend who stepped behind her and leaned close to her ear.

“No hands, Cass,” she whispered.

Cassie got very nervous and the whisper felt like a tickle that sent butterflies into her stomach. She’d never been able to give a blow job without her hands.

She lowered her arm and focused. Now as she licked him, his cock bobbed and bounced. She felt like she was chasing it with her tongue, struggling to make it go where she wanted. It kept bumping her nose and face which made things more awkward.

She took her time, licking him a few different ways and figured out how to move him where she wanted it. After teasing him with her tongue, she took him into her mouth and began bobbing up and down on his small cock. She was thankful he was small so she could easily take all of him. She was afraid he might get rough and it’d be difficult to temper him with just her mouth.

Val moved closer to her and pulled her hair back, pulling it into a ponytail and slipping a scrunchie over it to keep it together.

Bradshaw nodded at her by way of thanks.

Cassie was getting into a good rhythm and she could hear his breathing getting ragged. She could tell it wouldn’t be too long before he’d cum.

He nodded again at Val and she pulled Cassie’s head back just in time for him to cum on her face. Despite his small size, he fired a lot of jizz onto Cassie’s face, leaning two lines of cum dripping down her cheeks.

She started to reach up to clean it off when Bradshaw finally spoke.

“No, Cassie. Leave it there. Val will walk you back to your hotel and send me a picture of you in the room. Then you can clean it off.”

Her smiled evilly. THIS was what really got him off…

Cassie was mortified. Downtown was quiet…but not empty. And the hotel would probably have people coming and going from breakfast.

She stood up and put her top back on, trying to compose herself. Val slid the cash into her handbag as she did.

He stood and fixed his pants and moved back to his chair behind the desk, watching Cassie get herself together, but not touching her face.

“Val will give you the details of your next assignment and get you everything you need to complete it. She’ll tell you what you need to know back at your hotel. Val, get a pic of her now…do I can compare it to the hotel photo?”

“Of course.”

Val snapped a quick picture of Cassie’s face dripping with cum and sent it to Bradshaw. His phone beeped and he looked at it, smiling.

“I’m so looking forward to our year together. Enjoy your day, Cassie.”

Cassie could only nod, her head spinning from what just happened and what she’d agreed to. She looked back once at his grinning face, then turned and followed Val out of his office.

———-

Val led Cassie back through the empty office, past reception and into the elevator. Neither of them spoke. Cassie was trying to process what just happened and she thought Val was a bit embarrassed. It was obvious now how well she knew Bradshaw.

Once in the privacy of the elevator, they both exhaled and relaxed a bit.

“Is that…is that what my year is going to be like? Getting him off?”

“No. You actually might not see him again.”

“What?”

“He’s going to monitor you…by picture…video…audio…But not in person.”

Cassie looked confused.

“So, he’s paying me that money to…to do stuff with other people?”

“A lot of it will be just you. But, yeah, other people.”

“What now?”

“We go back to your hotel room, I’ll send him another picture and we’ll get you cleaned up. Then I’ll help you get ready for the year and we can go get lunch or something.”

“Ok.”

The elevator arrived on the ground floor and the two women stepped out. Cassie felt her heels were extremely loud on the marble floor, the sound echoing through the empty lobby.

Cassie walked towards the exit gate next to the security desk. The guard looked up from the computer screen and reached out to take Cassie’s guest badge.

She stepped through the gate and started to head for the exit, relieved he didn’t seem to notice her cum covered face.

She got about five steps away from the desk when the guard called her back.

“Here’s your permanent security pass, miss. That’ll get you in 24x7x365. Enjoy your day.”

Cassie took it from him and was horrified to see it was the picture Val had just taken upstairs. The cum clearly visible.

She looked up from the badge and the guard was staring at her with a massive smile, but said nothing.

Her face went crimson and she mumbled a thanks before walking briskly to the door. She’d never felt more relieved to get of a building. Fortunately, the street was empty.

The hotel was about four blocks away. Cassie walked as fast as she could in the heels, mentally counting down her remaining time wearing the cum.

They got back to the hotel and walked up the carpeted steps to the main door. A uniformed guy in his 20s held the door open and said good morning.

Cassie thought he noticed–but she couldn’t be sure. She walked past him into the lobby, turning her face slightly away from him.

The hotel was somewhat busy. A dozen people were sitting on couches and chairs around the lobby, with another 10 checking out at the reception desk. A few knots of people were coming or going from the dining room for breakfast.

The pair headed for the elavators. To Cassie’s horror, just as the doors opened a middle aged couple raced to join them before the doors closed.

Val asked them their floor and they asked for the fifth–Cassie was on the fourth so there was no early escape.

Cassie tried turning towards the wall, but they were polished and reflective. The husband was trying to subtly check her out in the reflection and his expression suddenly changed. Cassie guessed he spotted her face.

After what seemed like ages, the elevator arrived at their floor and they got out and went to Cassie’s room.

———-

Cassie practically fell into the chair. She leaned forward, holding her head in her hands and started crying.

“What have I done? What have I gotten myself into?”

“Cassie. Stop. I need you to stand so I can get a picture before you wipe your face.”

Cassie looked up at Val. She’d almost forgotten. After all of that humiliation, she couldn’t not get credit for it.

She composed herself and stood up, trying to look like she hadn’t been crying, despite her reddened eyes.

Val took a few quick photos and was tapping her phone, presumably sending them to Bradshaw.

“Go take a shower and change clothes. You’ll feel better, Cass.”

She looked shell shocked. But, Val’s words seemed to help her snap back to herself. She nodded and headed to the bathroom.

She thought it was the best shower she’d ever had. She turned the water on extra hot and blasted herself with the water, wanting to wash this morning away. To somehow remove it from her memory.

When she got out, she brushed her teeth twice before stepping back into the bedroom in the chunky bathrobe.

Val was sitting in the living room area, scrolling on her phone. She looked up as Cassie came out.

“Are you ok?”

“Yeah.” She shook her head, “I’ve done worse. He was just so…so…clinical? Just impersonal. Like I didn’t matter and he didn’t care…but he did it anyway.”

“He’s…that’s how he is. Everything is transactional. He can have a hundred girls in his room if he wanted to. But, he’d prefer to mindfuck people.”

“Am I really going to be ok?”

“Yeah. It’s crazy money for some crazy stuff. You’ll probably enjoy half of it and you can think about the money during the other half.”

“What now?”

“I’ll get you set up.”

Val pulled out a measuring tape and measured Cassie in a few places and asked her shoe size, bra size, etc. she explained it was so they could buy her clothing.

Then Val handed her a brand new iPhone and helped her set it up. It had three unusual apps on it–nothing Cassie had ever seen before. There were three numbers in the contacts: Val’s, Bradshaw’s and one entry simply called “Help–ICE.”

Val explained that the phone was paid for with unlimited internet and roaming. The Help contact was Bradshaw’s security firm and fixer. Anything she needed while on a “mission” would be taken care of if she called or text them anytime 24×7.

The three apps were a to do list app called Control, a streaming app for audio or video called Watcher and a tracking app called Locator so Bradshaw could see where she was at any time.

“Here’s how it’ll work. I’m basically your handler. I’ll give you missions and all the details you need and make sure you have anything else you need from airline tickets to clothing. Keep this phone with you at all times–even when you’re off the clock–you’ll always have time between missions.”

“When’s the next…mission?”

Val made a face as though delivering bad news. “Tonight after dinner.”

Cassie blanched and her stomach sank. She had thought there’d be breaks between things. But, she guessed he wanted to do something else with her while she was in Austin.