The Challenge: Ch. 06

Inside her room, Cassie followed instructions and took several selfies of her wearing the skimpy, cum covered dress.

She uploaded the pictures into the Control app and the challenge changed from "in progress" to complete.

She slipped her feet out of the ridiculously high heels and removed the dress and jumped into the shower.

She adjusted the shower as hot as she could stand and at high pressure. She used loads of body wash, working it into her skin as though trying to wash away the night.

As she scrubbed, she replayed the evening in her mind. Being made to get those people off had disgusted her. But, she also enjoyed it. If she wasn't so tired, she'd actually get back in the car for more.

Almost subconsciously she began teasing herself. She gently traced her fingernails over her breast, focusing on the nipple. Meanwhile her right hand began rubbing her clit. The whole night had been like foreplay, leaving her wet with no release.

As she replayed the night in her head, she took down the shower head and directed the water between her legs. The water felt amazing. Almost like it was throbbing, like a constant drumbeat between her legs.

Was it the freedom of being made to do things she secretly wanted to do? Was it the constant watching if Val making her feel like she was performing? Was it the humiliation of it all? Maybe some weird mix?

She closed her eyes, thinking about the pulsing cocks between her legs and her encounter with the two women. As she thought of being licked by the woman in the limo she exploded. It was so intense she had to use her free hand to steady herself against the shower wall.

After the third massive wave of pleasure wracked her body, she redirected the water and finished her shower. She towelled off and put on one of the hotel's robes and sat in the bed, relaxing.

There was a laptop sitting on the nightstand that wasn't hers. It must have been left by whoever dropped off the dress to her earlier or maybe they came back while she was out?

She opened the laptop and it came on. The desktop had a single icon in the middle of the screen with the Control app--the same one as on the phone they'd given her.

She clicked on it.

The first surprise was that her profile icon had changed from a C in a circle to a headshot of her wearing the dress tonight. She guessed it was from a photo taken at the restaurant.

Near the top, it showed the number of days remaining on the contract--364. She sighed.

The history tab listed two items--tonight's challenge and another one called "Introduction."

She expanded Introduction and now saw a brief description reading simply "initial meeting and contract." Next to it was a link to "View."

She shuddered. Val told her they'd film everything...

She clicked onto Challenge 1 and saw several video links. She clicked on and watched a few seconds. It was a split screen of her in the car--captured from four different cameras.

She looked around her room wondering if they were filming her now. Nothing looked like a camera. But, she hadn't noticed them in the limo either.

Suddenly, a chat window popped up in the app.

"Optional challenge available for completion now."

She clicked it.

"Optional Challenge--

The night manager appears to have taken an interest in you. Have sex with him anywhere other than your hotel room before dawn to complete.

Reward: reduce challenge contract by 3 days.

Accept or Decline?"

She recoiled from the task. That guy was kind of creepy. The way he ogled her made her really uncomfortable.

Her second thought was to wonder how they knew. Did they have access to the security cameras in the hotel? She thought she remembered someone in the lobby. So maybe they saw him looking at her?

If it was just another hand job, she'd definitely do it. Could she really have sex with this creepy guy? Three days might save her from something truly depraved. If handjobs in limos was day one, what did day 365 have in store for her?

She realised just pondering what to do was making her wet. Her first real task and they'd already gotten inside her head...

She clicked "Accept" and a follow up message appeared.

"Wear the dress for an additional day removed from the contract."

She sighed. That was almost worse than the task itself. She'd never felt as slutty as when the woman at reception saw her covered in cum stains.

She closed the laptop and tried to formulate a plan.

----------

As she put the tiny, stained black dress back on, she thought up a way to meet the night manager hopefully without going back to the lobby.

She picked up the hotel phone and dialled reception. The woman answered, so Cassie asked for the night manager.

He came on the phone almost instantly.

"Good evening, Miss. This is George, the Night Manager. How can I help you?"

"Hi, George. I have kind of a silly problem...I was in the hotel gym earlier today and I think I left something important in there."

"Oh. I'm sorry. The gym is locked up for the night...but, it'll be open at 7am sharp."

She tried to sound a bit flirty and helpless.

"Yeah...well...I uh...have an early start tomorrow so that might be too late. Is there *any* way you could help me now? Maybe I could meet you there? I think it would only take a few minutes..."

His voice softened. "I'd love to help you. If you want, I can meet you there in 5 to 10 minutes?"

"That would be amazing! Thank you so much. See you in a minute."

She got off the phone, still repulsed and excited by what she was about to do.

She took her handbag with her and stepped out into the empty hallway, tottering on the too-high heels which forced her to walk much slower than she wanted to.

She took the elevator to the top floor which was as empty and quiet as the floor her room was on. In addition to the gym, this level had a small business centre and a handful of larger suits. This time of night, there was no reason for anyone other than a few guests to come up.

The gym took up one corner of the building so people working out would have windows on two sides. Apart from a small bathroom and changing area, it was a single open plan room. Since it was closed for the night, the lights were off and she could just make out the outlines of equipment in the shadows.

It felt like she was waiting ages for him to arrive. Her heart was racing and her breathing was a bit ragged. She took a quick selfie to prove she'd worn the dress again.

Eventually, she heard the elevator doors, then footsteps coming down the hall. She peeked around the corner and saw George walking quickly towards her. He smiled broadly when he noticed her.

She forced a smile and gave him a half wave as a greeting--not wanting to make noise and risk drawing anyone else's attention.

When he got close, she whispered to him, "Thank you *so* much for helping me."

He smiled back, nodded the spoke softly, "My pleasure. What did you lose in the gym?"

"Just a mailing envelope. I think it's in the far corner near the window."

He pulled out his keycard and unlocked the door. There was a bank of light switches on the wall. He flipped on just one of them which turned on a handful of recessed lights, leaving the gym dimly lit.

Cassie entered and walked past George, heading purposefully towards the far corner.

As she'd hoped, he followed her at a distance.

She made her way to the window near six treadmills all placed facing outward. Cassie pretended to look for the envelope, walking around the area and bending over.

George caught up to her.

"Where do you think you left it? I can help you look."

She decided to take a direct approach. She stood up and looked him in the eye, smiling what she hoped was seductively.

"George. Do you find me attractive?"

He looked stunned and confused.

"Uh...you look...uh...very well, Miss." He was flustered--his face a mix of surprise and maybe interest, she thought.

Cassie realised she was enjoying having the upper hand with him--even though her goal wasn't something she actually wanted apart from to reduce the contract length.

But she liked the role reversal--pursuing a guy openly and brazenly like this and knowing he'd almost certainly say yes to whatever she asked. She felt a throb of excitement.

"But, am I fuckable, George? Would you have sex with me if I asked you to?"

He was stunned. Nothing like this had ever happened to him before. It was like a porn video.

He tried to compose himself and look more confident than he felt. He stood up straight and tried to meet her intense gaze.

His voice betrayed him, "Yuh...yeah. I'd uh...love to have sex with you."

"Great. Let's see how much."

Cassie walked over to him and began undoing his belt. George seemed frozen, just letting her take charge.

She unzipped his fly and pushed his pants down. He had a modest sized cock that was only semi hard. She guessed this whole scenario was dampening his performance.

She began massaging his prick between her fingers, teasing his balls with her nails in between gently squeezing his cock to full hardness.

"There it goes. Nice and hard for me."

She pulled a condom out of her handbag and handed it to him.

"Put that on while I adjust this dress."

Flummoxed, he took it and quickly opened it. He looked back towards the door which had locked behind them. They were actually in one of the darker parts of the gym.

Cassie pulled the dress up and had to wiggle her hips to get it above her hips because it was so tight.

She'd left her panties off when she got dressed so she'd have one less thing to worry about. She glanced at George and saw he was about her height, so she kicked off the heels. She noticed he had the condom on and was standing somewhat sheepishly, waiting for instructions.

She stepped over onto the treadmill and took hold of the bar.

Looking back she told him firmly, "Come over here and fuck me, George. I want a real man to make me cum."

He almost tripped over his pants which were around his ankles. He paused just long enough to pull them off and set them aside before practically running the few steps over to her. He was still wearing his shirt and jacket.

He stepped up behind her and gently guided his cock inside her very wet pussy. She moaned softly as he entered, loving some attention after the long night of foreplay. The shower wasn't nearly enough.

He began thrusting into her. She leaned forward, wanting him deeper inside her. She wished he was a couple of inches longer--but, she'd make due.

She could see him fucking her in the reflection on the dark window. His face was a mix of determination and concentration. She could make out the downtown lights on the street below.

"Fuck yeah...harder, George...deep...that's good..."

They quickly got into a good rythym. She had a small orgasm after only a minute, but wanted more. She craved proper release.

She heard him starting to grunt behind him and knew he wasn't going to last much longer.

He didn't. He thrusted a few more times and she could feel him spasm inside her. Fuck. She needed to cum.

"Did you cum, George?"

"Uh...yeah." His breathing was ragged. He started to pull out.

"I'm not done, George. I'm going to need you to do more."

"But, I'm...uh...you know."

She turned around and looked at him intensely, then took a couple of steps and sat down on a weight bed.

"Get your mouth down here and make me cum."

She spread her legs wide apart.

"I...uh..."

"Now, George."

He suddenly looked like a child who'd been scolded. But, he kneeled between her legs, the condom still on his shrinking cock.

He was really bad at this. But, Cassie didn't care. She held her lips open and guided his tongue to her throbbing clit.

After a few tries and some help, he figured out what she liked.

"That's it...keep going...right there...don't...fucking move..."

She exploded with a massive orgasm, letting out louder cries than she normally would. All the teasing of the night bubbling over into a wave of pleasure that washed over her.

Unknowingly, she'd pressed her thighs tight against his head as she ground hard against his mouth, pulling his head tightly towards her.

As the last wave of pleasure subsided, she stopped pressing his head and gently rubbed his hair as she opened her thighs to release him.

"Good boy, George. That was perfect."

They both stood and Cassie pushed the dress down and back into place.

"Let me help you with that."

She removed the condom and tied it shut, slipping it into her purse.

George looked stunned but happy. She put his underwear and pants back on and tried to make himself look presentable again.

"Did you...uh...find that envelope?"

She smiled broadly, "I got what I needed."

He smiled dumbly. Cassie thought it was only now that he realised sex was what she was after and there was no other reason to be here.

"Goodnight, George. Oh, and you might want to wash your face before you go back or your lovely coworker might notice my juices all over you."

She gave him a small peck and winked then headed back to her room.

He stayed in the gym for a few minutes--she guessed to freshen up. She was glad he did so she didn't have to share the elevator with him.

Back in her room she updated the app to mark the mission completed and uploaded pics of her in the dress and the filled condom. The time remaining on the contract had updated to show 360 days left.