The Challenge: Ch. 03

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Chapter 3

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The two women spent the rest of the day doing normal, visitor from out of town things. Val showed her some of Austin's sights and they had a good catch up session over lunch.

Cassie mostly pushed what was happening to the back of her mind and really enjoyed not worrying about money or her family for a long afternoon.

She eventually asked Val about the whole challenge thing. Val explained that she was the first person and Cassie was now the fifth. Val thought Bradshaw had other challenges running at the same time, but she wasn't sure.

"I was at the main security office once, monitoring a mission with them. They have this room with about a dozen monitors. I noticed half of them were watching my challenger and the others were watching some guy I'd never seen before. I knew better than to ask..."

"Was he doing something for Bradshaw?"

"I think so. He phoned and was talking to the team about him."

"What...what was he doing?"

"He had him robbing a house. But, just stealing one thing--some kid's high school track trophy. It was like some of our missions...basically harmless but with a frisson of...being on the edge."

"Did he succeed?"

"Yeah," Val laughed a bit. "He got it and was almost out of the house when the homeowner woke up, I'm guesswork he was in on it since there were cameras everywhere in the house. Anyway, the guy got out before the man caught him."

Val dropped her back at the hotel.

"Meet me here out front at 7 on the dot and we'll head to dinner. The Control app will have more info for you..."--she checked the time--" any minute now."

"Ok. See you soon."

Val drove away leaving Cassie feeling suddenly alone and vulnerable.

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As Cassie made her way up to her hotel room, her phone chimed. Her heart skipped a beat and she was instantly nervous and on edge.

The Control app had instructions for her--

"Mission #2 [Day 1/365]: Go to dinner with V wearing the outfit left for you in your room. V will bring 3 men to you and 1 woman in a car. Ensure each one cums using only your hands. They're allowed to explore your body. Wipe their cum on your clothes. V will verify with Watcher.

Accept or fofeit?"

Cassie clicked the accept button and continued on to her room.

Inside she found four shopping bags containing luxury toiletries and bath lotions, a full makeup kit, a lacy bra with matching underwear and stockings, impossibly high her and a very revealing leather dress. There was even a matching handbag.

She laid everything out on the bed and waited in the living room area until she had to start getting ready. She tried in vain to distract herself from tonight's "mission" but all she could do is imagine herself giving hand jobs to random guys.

The bra and underwear were matching black lace. The bra had holes which exposed her nipples and the panties had a slit so her pussy was on display. The stockings went up to the top of her thighs.

It was tricky getting the leather dress on. It was very short and barely covered the top of the stockings. It had thin straps and was low cut with a deep V which meant her breasts and bra were on display. The dress was also mostly open at the back below the bra line. As if all that wasn't enough, it was held together with strategically placed zippers. Cassie almost felt more exposed wearing the dress than she did before she put it on.

The makeup bag had a printout of instructions for doing an "ultimate slut look for your night out" from some website she'd never heard of. She tried as best she could to recreate the look, but apart from the black eyes, it seemed to be heavy on reds.

The makeup box included massive silver hoop earrings and a non-piercing nose ring as well as a long thin silver chain.

The last challenge was the shoes. The heels were 3" tall, open toe and had only tiny spikes for support. They perfectly matched the dress and even had zipper designs on the outside.

Cassie put of the shoes to complete the ensemble and practiced walking around the room. After a few laps, she was able to walk steadily as long as she took it slow. She'd heard of "curb to club" shoes and these were definitely falling into that category.

Before she headed out, she decided to look in the handbag. It had $1000 cash in mixed denominations, a credit card with her name on it, a small tazer, a few small sex toys, lube and a dozen flavoured condoms. She shut the bag and tried not to think too much about the contents.

At 6:50 she headed to the front of the hotel to meet Val. Where the hotel had been thankfully quiet this morning, it was buzzing with activity and people seemed to be everywhere.

When she came out of her room, there were three casually dressed middle aged men chatting. They fell silent when they saw her and Cassie saw them motioning to each other and pointing towards her.

She tried to keep her composure and ignore them. She simply walked past them to the elevator. When the doors opened, they followed her inside and were also going to the ground floor lobby.

She stood against the wall, not wanting to turn her back to them. They stood to her left and right and began talking softly about where they were headed to dinner.

After what seemed like ages, the doors opened to the lobby. The men waited for her to exit first and she swore she could feel their gazes burning into her back as they followed behind her.

She stepped into the lobby and the stiletto heels sounded like gunfire on the marble floor as she walked at a steady pace to help keep her balance.

There were knots of people dotted around the lobby. Groups and couples sitting or standing, chatting and drinking. As she passed, the nearby conversations seemed to stop and everyone seemed to be staring at her.

Cassie felt her cheeks burning with embarrassment. She never liked being the centre of attention and looking this way made it infinitely worse. She wanted to run out the door, but the awkward heels forced her to walk at a slightly slow pace.

She made her way to the door and one of the younger staff members held the door open for her. She stepped outside into the overly warm Texas evening.

Val was mercifully parked just outside. She was dressed in jeans with a casual top and comfortable looking heels leaning against her car with her trademark sunglasses. Cassie noticed Val was filming her with her phone.

She smiled slightly--out of recognition than of any mockery.

"Hey Cass! Hop in."

The two women got into the car. Cassie struggled to get in without exposing herself and more or less succeeded. Fortunately, no one was very close and the car door helped block the view from the main hotel doors where people were hovering waiting for ride shares and taxis.

"That's uh...quite an outfit they picked for you." Val did a slight snort laugh and glanced over before focusing back on the road ahead as she sped off.

Cassie rolled her eyes. "I've never dressed like this! Not even on my craziest college night. What even is this? Slut S&M on acid?"

The two women laughed.

"I don't know if it's Bradshaw or someone else who picked that...but I'm guessing a 15 year old boy had a major role in the selection."

They laughed again as Val drove the short distance to the restaurant.

Cassie felt a bit better. As unnatural as this whole situation was, she was glad she could still laugh and thankful Val was with her.

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Val took her to a restaurant overlooking the lake. The building was a large wooden structure resembling an oversized house with lots of windows.

Val pulled up outside the door and handed the keys to the valet. She took some details from Val as Cassie struggled to get out of the car in the ridiculously short dress.

The valet looked up from the podium desk and ogled Cassie as her dress rode up. Their eyes locked and Cassie blushed with embarrassment as she stepped past her. The valet looked barely 18. She was a stunning, thin light skinned Black woman with beautiful long hair and a mischievous grin.

She waited for Cassie to get out and close the door before she walked to the driver's side and parked the car.

They walked into the restaurant and the host took them outside to a table on the deck overlooking the lake. For Cassie, this meant having to walk the length of the crowded restaurant as well as past all the full tables outside.

Cassie tried to relax. The people nearby had gotten used to her and went back to their own conversations. She still noticed an occasional sideways glance, but it was infrequent enough for her to focus on her meal.

When they finished eating, Val excused herself. Cassie watched her as she found someone she guessed was the manager. Val shook the woman's hand and had a quick conversation. Then she saw Val head off to the front of the restaurant and step outside.

What was Val up to?

A few minutes later, Val was back in the restaurant and eventually came back to the table after what looked like a detour to the restroom.

"Ok. I have the first part of your mission ready."

"Now? Here?"

Val smiled like the cat that got the canary and it made Cassie's blood run cold. Was Val on her side at all?

"Yeah. Go into the restaurant and head left down the hallway towards the restrooms. There's a door at the very end that says employee's only. Go in there and wait."

Cassie knew tonight's mission was to give hand jobs snd figured Val must have known someone at the restaurant.

Cassie frowned and sighed, resigned to what was coming. She stood, again drawing attention from the diners around them as she trundled gingerly across the deck and inside.

The restaurant was jam packed with every one of the dozen or so tables full of people eating dinner. She ambled in trying not to draw attention to herself and headed down the hallway, passing the men's and women's restroom doors. She found the door Val told her about and turned the knob.

She stepped into a windowless storeroom with shelves on all sides stacked high with boxes of everything from napkins to canned goods. The room was mostly shadows since the overhead lights were badly located over the shelves which blocked most of the direct light from above.

Her phone chimed and she had a message from Val--

-- I'm sending in a girl to you. Get her off. Remember she can do anything to you but you can only use your fingers to make her cum.

-- ok

Cassie stood in the room, the boxes seeming to dampen any noise so that the place was unnaturally quiet. Her heart was racing and she felt herself getting wet.

She hadn't been with another woman more than a handful of times--mostly with Val. Now she was dressed as a slut waiting to pleasure a stranger.

Val seemed to know the manager. Was she a lesbian? Was Val trading favours with her or was Bradshaw using her as well?

Time seemed to crawl. She kept checking the time, but only four minutes had passed when the door finally opened.

Cassie was both surprised and relieved to see the beautiful valet who'd parked the car for them. She was beautifull and wore a kind of retro jumpsuit that was somehow futuristic and old fashioned at the same time. Her name tag simply read "Tarsha Valet Parking."

"So, Cassie, you're my tip." Her face changed to a wide radiant smile.

"Oh...sure."

"Let's see the goods." She gestured an unhooking motion.

"My...uh top?"

"Yeah, girl. Tits out. I'm on break, so this needs to be quick, slut."

"Oh...uh...ok." Cassie was stunned by her words. She hadn't expected this kind of harshness.

She fumbled, pulling the straps of the dress to the sides and shifting the fabric off of her chest, exposing the lacy bra and her nipples.

"You came to fuck, didn't you slut?"

Tarsha reached out and roughly grabbed her breasts, squeezing her nipples between her fingers.

"No...I uh..."

Tarsha laughed, shaking her head as she reached down and hiked up Cassie's dress. She slipped her fingers through the slit in her underwear into her pussy, easily sliding two fingers into her wetness.

She grinned as she wiped her fingers dry on Cassie's chest.

"Someone likes being a slut! Don't you?"

"No...it's uh...complicated..."

"Whatever. I don't care."

Tarsha stepped back and slipped out of her uniform slacks and underwear. There was an old desk chair in the corner of the room and Tarsha seated herself in it and spread her legs.

"Get over here and get busy. I don't have all night slut."

Cassie stepped over towards her, pulling her dress down so she could move her legs properly, her boobs still fully exposed.

Tarsha pulled her towards her and kissed her, her tongue parting Cassie's lips and then sliding together. She grabbed her breasts again, pressing her nipples between her fingers and thumbs.

Tarsha took Cassie's hand and pulled it against her pussy, letting out a soft moan as Cassie's fingers parted her folds, her thumb rubbing Tarsha's clit as her fingers slid inside her.

Cassie found a good rhythm Tarsha liked and had three fingers sliding into her. Tarsha squeezed her breasts, digging into her soft flesh slightly with the tips of her fingernails.

Their kiss didn't break until Tarsha came. She pulled back her head and closed her eyes tightly as she came, squeezing Cassie's boobs even harder as the pleasure washed over her.

Cassie slowed the pace, focusing on her clit as she pressed hard against her, stopping in place when Tarsha untensed. She gently withdrew her fingers from her tight pussy.

Tarsha kissed her softly then let go of her and quickly stood up.

She checked her watch then put on her discarded clothes.

"That was nice. Get yourself together. I think your friend is outside."

Cassie just nodded. Her clit throbbed begging for attention, but she knew she had to go.

Tarsha kissed her one last time then smiled and left the room.

Cassie followed instructions and wiped her hands dry onto the dress and quickly stepped out into the hallway.

Val was waiting outside.

"Go to the car. I'll be right there."

Cassie felt kind of like a child as she obeyed. She just nodded and headed out, tottering slowly on the heels.

Val went into the storeroom and came out and caught up to her in the hall.

She smiled mischievously as she leaned close to Cassie's ear and whispered, "the smell of pussy in there is unreal! You really got her wet."

Cassie said nothing. She started to open her mouth, then just froze from embarrassment.

Val saw her expression and laughed softly as they arrived at the front door. The restrooms were close enough to the entrance that she was spared a million more stares from the diners--only the few couples waiting to sit down and the hostess stared at her.

They stepped out into the hot Texas night. A large car was waiting at the curb and Tarsha stood grinning at the valet desk.

Tarsha locked eyes with Cassie and theatrically licked her lips.

"Goodnight ladies. I hope the rest of your evening is at least half as nice."

"It'll be tough, but we'll try," Val said before adding, "thanks for your help."

"It was better than most of my tips. Oh and next time? I want to try out that tongue of yours."

Cassie reddened but remained quiet, too embarrassed to say anything in front of Val who suddenly seemed to be enjoying her discomfort.

She looked ahead of them. It wasn't Val's car waiting for them, but some kind of large black sedan akin to a small limo with dark rear windows.

As they approached, a man got out and opened the back door, bobbing his head towards it.

"This is Marco, he's going to drive us tonight."

Marco was huge. He looked like a professional wrestler stuffed into a black suit. His massive bald head towered over them with an impassive expression. Cassie noticed he wore a communication plug in his ear making him look like a member of the secret service.

Cassie said hello and he said, "good evening, ladies."

He held open the back door for the ladies, waiting for them to get in the car.

The car was a small limousine with two bench seats facing each other in the back and normal seats up front. Marco had already raised the black privacy partition between him the the passengers.

Val sat in the rear-facing seat across from Cassie.

Marco drove forward towards the main road.