The Challenge: Ch. 05

After they dropped off the couple, Val joined Cassie in the back.

"Are you doing ok?"

Cassie sighed. She didn't want Val to think she was enjoying herself--but didn't want to sound too defeated.

"I...uh...it's ok." Cassie looked down.

"Good. You're almost done. Just two more and we can call it a night."

Cassie nodded, avoiding eye contact with Val, But, she felt herself get more excited thinking of what might happen next.

Val tapped the tablet, making faces as she looked at available riders. Suddenly she snorted and giggled, tapping the screen.

"What is it?"

"2 riders...but the profile is for a 30ish guy--Beck. They're usually fun."

"Usually? How often..." her voice trailed off.

Val just shook her head, leaving the partial question unanswered.

Cassie wondered how much of this Val had done. Was this actually her job now? Did Bradshaw have other people he was toying with?

Marco pulled the car up in front of a Gentleman's club. The business had made an effort to look upscale, but Cassie thought they'd failed. It was just a square building with a nice sign and some basic landscaping.

Two well dressed guys in their late 30s walked towards the car, one of them was a bit unsteady. Cassie guessed from drinking.

"Oh, hey...we thought this was our car..." it was the more sobor of the two.

Val replied, "It is. Hop in if you don't mind sharing?"

He smiled at Val and looked over at Cassie, obviously checking her out.

"Cool." He turned to his unsteady friend, "Behave yourself, Dan. There's ladies present."

The two guys got in the car. They were both wearing slacks and well traveled suits with dress shirts. They looked like businessmen travelling for work who hadn't made it back to the hotel to change before going out.

"So, are you like helping the driver?" Beck nodded towards the tablet in Val's lap which clearly showed the rideshare app with Beck's profile.

Val smiled, looking somewhat like a shop clerk--only just friendly, but not overly so.

"Are you guys having a good night?" Val replied, steering the conversation.

"Yeah...always nice to see the local talent." Dan licked his lips as he leered at the two women facing him.

"This may be your lucky night. My friend here lost a bet. She'd be happy to give you each a nice hand job on the way to your hotel."

Beck turned suddenly towards her, looking suddenly very sheepish.

"Uh...well...I'm uh...no thanks. We're not THAT good of friends, right Dan?"

"I'm up for it. Sure how often does your wife let you off the leash?"

"No way. I do NOT want to watch you get off."

"That's a shame. It's kind of an all or nothing deal." Val made a point of looking towards Beck's crotch. "You're probably pretty worked up from the dancers? Aren't you?"

She leaned towards him, extending her arm and pointing towards his waist.

"Come on man. Let's do this."

Cassie got up and sat between the two men.

Dan quickly unbuckled his belt and slid his pants down to his ankles, freeing his cock which was already hard. Cassie took it in her left hand and began squeezing it gently, massaging it.

Cassie made a point of turning towards him, blocking Beck's view with her back.

Beck looked stunned. He looked across at Val who seemed to be focused on the tablet. She looked up at him briefly then tilted he head towards his friend, smiling devilishly.

"Um...maybe you could...ah...do me?"

Val looked up. "Nope. She will if you want her to. She has a free hand." She made a point of returning her focus to the tablet.

Cassie turned to face Beck, her left hand now slowly massaging Dan's cock. Dan laid back, spreading his legs a bit and getting more comfortable. He folded his arms behind his head.

Cassie started to reach for Beck's zipper. She made eye contact with him and saw the uncertain look on his face.

"No...uh...no thanks. Maybe another time."

"Ok." Cassie turned back towards Dan. There was something satisfying in Beck's discomfort. It made her tingle having this kind of power over him.

Val handed Cassie a tube of lube. She put some in her hand, then rubbed it onto Dan's cock and began to really work it, now with both hands.

Whenever she found a motion that made the lube make a clicking sound, she repeated it. She wanted Beck to hear what he was missing even though he was trying hard to stare out the window and ignore the handjob his coworker was getting just a couple of feet away.

Cassie really wanted to just climb onto Dan's cock and ride him. Beck's discomfort made her mind buzz and her pussy even wetter as she stroked the warm stiff cock between her fingers.

Dan had been hard most of the night at the club so he didn't last long. He leaned back, groaned and came in several long spurts. His cum flew in an arc, landing mostly on the car door and floor in front of him.

"Ahhhh...so good."

When he finished, Cassie leaned over and mopped up his spunk with her dress.

When she leaned back in her chair, she could see Beck was staring at her. She saw the bulge in his pants and raised her eyebrows as their eyes met.

"Perfect timing. We're almost to your hotel gentlemen." Val announced, sharing a smile with her friend.

"That was amazing. You missed out dude." Dan quickly pulled up his pants and tried to make himself look normal before he had to walk through the lobby.

Dan leaned over towards Cassie and gave her a gentle peck in the cheek as the car pulled to a stop, giving her a big thanks before he stepped out of the car.

Beck didn't move.

"We're here. Time to go," Val said, the evil smile back on her crimson lips.

"Could I...ah...stay and...you know?"

"What about your friend? He's already left." Val said evenly.

"I can...I can text him."

Cassie jumped in, "How much is it worth to you?"

He looked confused. He looked back and forth between the two women.

"I uh...thought it was a...uh bet or something."

"It is. But I needed two guys at once. You ruined it. So, if you want it, it'll cost you." Cassie lied, wanting to make him work for it. She didn't need him--she'd already completed the challenge. But, she was having fun...

"Ok...well...I don't have much cash on me...maybe 50?"

"75."

"I think I...uh...only have 50."

"That's a shame. Well, enjoy your night."

"What if I uh...gave you 50 in cash and then tipped 25 in the app?"

"They take a big cut," Val said. "The tip would need to be bigger."

"Do 50 and 50 and I'll get you off."

Beck looked annoyed and defeated. But he agreed, just nodding, not saying a word.

Val tapped a few times on the tablet and the car drove off. Marco parked around the back of the hotel near the service area. This time of night, it was deserted.

"Now leave the tip and message your friend," Val told him flatly.

Beck handed the 50 to Cassie and started typing on his phone. Val's tablet beeped a moment later and she nodded at Cassie.

Cassie started opening his pants. She undid his belt then opened his fly. She helped him pull down his pants and fished out his rock hard cock and began massaging it.

Val handed her the lube again and she began rubbing it over his skin.

"So, does your wife know what you get up to on business trips?" Val asked, looking straight at Beck.

Cassie smiled as she massaged his cock and balls. She gently poked his balls with her nails when Val mentioned his wife.

"What do you mean?"

"Strip clubs...paying women you just met for handjobs?"

"Hey, you two offered it to me--I didn't go looking for it." He suddenly looked a bit panicked and confused.

"What do you think of his cock, Cass?"

"Eh...it's a bit small for me." She squeezed him as she answered to punctuate her comment.

"Hey!"

"What kind of car do you have?" Val asked.

"What? Why are you going to insult that too?"

"Just seeing if your small dick energy affected your choice in cars."

"Come on! What's up with you bitch?"

Cassie took her hands away.

"Why'd you stop?"

"You called my friend a bitch. So we're done."

"Actually...now it's my turn." Val said coldly, smiling evily.

"You're going to finish me off?"

"No. You are." Val pulled a taser out of a compartment. "You have 2 minutes to cum or I'll zap you." She tapped her watch.

Cassie moved over to sit next to Val and made a show of cleaning off her hands.

Beck started to pull his pants up. Val pushed a button and locked the doors.

Cassie wanted to join in.. She pulled her own taser out of the handbag and clicked it, making it buzz.

"A minute forty left...then buzzzt." Val tilted her head towards him, urging him to get on with it.

"You're crazy. Both of you."

"One twenty..."

Beck frowned. Defeated, he grabbed his cock and began frantically jerking himself off. He closed his eyes--Cassie guessed trying to focus on something other than the threat in the car.

"One minute...you can make it."

"Ungh." Beck looked even more frantic.

Cassie and Val smiled at each other. They both looked like they were trying not to laugh.

Val just shook her head.

"Oooh...30 seconds. You're cutting it close."

Beck kept going. Cassie thought his jerking off almost looked painful now.

"10...9...almost out of time...3...2...1. Ooh. Too bad."

Beck kept going and eventually came about 40 seconds too late. After his cum spurted, he stopped and sat back, catching his breath.

"Satisfied now?"

"No. You took too long."

"Fuck you. Fuck both of you."

"Bad call."

Almost in unison, Val and Cassie tased him.

He fell to the floor of the limo, shaking from the shock.

Val unlocked the doors and pushed the door nearest to him open.

As the effects of the shock wore off, Beck began to crawl out of the limo, his cock still out and his pants still around his ankles.

Val leaned out the door and took several pictures of him with her camera. When she was done, she pulled the door shut and asked Marco to drive them home.

---------

Cassie was exhausted. The night had been emotionally draining and it was now late. She and Val were quiet as Marco drove them back to the hotel.

"So...is that everything?"

"Just about. When you get back to your room, take a few selfies and upload them to the app. He'll want to see the state of your dress."

Cassie's heart sank. It hadn't bothered her riding around in the slutty, cum stained dress. The car was dark and the passengers had all been distracted anyway. But, even late at night, there would be people in the hotel she'd need to get past to get to her room.

The limo pulled up outside the front door of the hotel and Marco opened the door for Cassie.

Fortunately, there was no one around. The hotel's doorman has finished for the night and the street was quiet.

Cassie said goodbye and awkwardly climbed the steps to the door in the high heels, trying to pull the dress down and in place as she went.

As she stepped into the hotel, she surreptitiously glanced at the dress. There were cum stains everywhere, especially bar the hem. She frowned, already flushing with embarrassment at the thought of anyone seeing her like this.

She walked into the quiet cavernous lobby. It was empty apart from a young woman and a middle aged man at reception--hotel staff chatting quietly behind the desk as they worked.

As she approached, the dark haired woman looked up with a service industry smile, "Good evening, Miss. Let us know if you need anything."

Her chipper voice shifted mid sentence as she took in the disheveled sight of Cassie. Her friendliness becoming a mix of confusion and concern as she looked her up and down.

Cassie burned with embarrassment, wondering if she guessed what the dress stains were. The guy at reception seemed to have figured it out and had a leering smile as his eyes roved over her body in the slutty dress.

Cassie mustered a simple good evening and a wave as she tried to hurry to the elevator. She felt like she could feel their gaze burning into her back.

The elevator seemed to take forever to arrive. Just as the doors started to open, the guy from reception sidled up to her, still wearing the awful smile.

He made a gesture inviting her to go in first and he followed.

"What floor, miss?"

"Uh...fourth...thanks."

"Same as me," he said, tapping the button.

His badge said he was Craig, the Night Manager.

Cassie took out her phone and began scrolling in some app--taking in nothing but wanting an excuse not to look at him.

"Looks like you spilled something. If you want, I can have that dress sent for dry cleaning first thing in the morning."

Cassie went crimson.

"Uh...no thanks...it's uh...I have a company I like. I'll get it later."

He just nodded, still grinning.

The elevator finally arrived at her floor. Only the high heels kept her from running down the hall--she couldn't even walk very quickly.

The guy stayed just outside the elevator, tidying up the flowers on the small table and straightening the pillows on the couch near the elevator.

She looked back only once as she arrived at her door and saw he was watching her from the waiting area.

She tapped her key and entered her room, relieved to finally be away from him and alone.