The Challenge: Ch. 04

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Chapter 4

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"So, how does this next part go?"

"We're going to be rideshare drivers...well...Marco is. I'll be in the front so you can complete the mission."

Cassie gulped. She'd thought Val would be with her which would make things easier.

"Can you...can you stay...with me?" Cassie felt suddenly desperate to have Val with her.

Val pursed her lips, her eye's hidden by her dark sunglasses. She seemed to pause, thinking.

"Is that really what you want? Me sitting here watching you give a handjob and getting groped by a stranger?"

"It uh...no but it's better, I think, than me just...alone."

"Ok. I'll stay with you for the first one at least."

"Thanks."

Val just nodded in reply and turned on a tablet that had been left for her on the seat. She tapped it a few times, then held it up facing Cassie. It was mirroring Marco's phone, allowing her to control the rideshare app.

"Let's see what's available...let's try...this guy...Jeff." She tapped the screen and it beeped in reply. She tilted the screen towards Cassie and showed her the rider bio pic for a middle aged guy who looked presentable.

Marco turned the car in response and headed to the pickup point in a restaurant parking lot, arriving a few minutes later.

Jeff was standing on the sidewalk waiting for them and approached the car as it stopped. Marco rolled down the window and spoke to him briefly to verify his identity.

Jeff opened the door and was surprised to see the ladies inside, "Oh, sorry...I thought this car was mine."

"It is. Do you mind sharing with us? We're going the same place?" Val replied.

Jeff looked back and forth at the women then checked his watch, looking a bit confused and maybe annoyed at having to share. But, his eyes settled on Cassie and that seemed to make the decision.

"Ah...ok..."

"Sit with my friend, Cass."

Cassie looked nervous, but patted the seat next to her by way of invitation.

Jeff climbed in and closed the door behind him, sitting next to Cassie and looking at the rideshare app on his phone.

Jeff had short, tidy dark blonde hair and wore beige pants with a casual denim button down shirt. He looked like someone who'd been to a business casual after work event. Cassie guessed he was mid-30s.

"You're only going a few blocks, so I'll have to be blunt with you. My friend here lost a bet and has to give a hand job to a stranger..." Val smiled broadly, "would you like to be our stranger?"

Jeff looked startled and slightly confused.

"I uh...have a girlfriend. I'm meeting her in like five minutes..."

"I could have our driver pull over until you're done and my friend will make sure you're nice and cleaned up before you arrive."

Jeff looked from one woman to the other, his brow furrowed, thinking.

"Is this for real? Is this like a scam or some prostitution thing?"

"No. I'll try to convince you...show this nice man your tits."

Cassie felt like a piece of meat. Val was practically begging this random guy to let her jack him off. She tried her best to smile and keep her composure. She felt like she was shaking from nervousness and was slightly disgusted with herself, her stomach churning. But, she held it together.

"Sure," she said as evenly as she could and swiftly undid her top, turning slightly towards him to give Jeff a clear view of her barely covered boobs.

"What...uh...what'll you do?"

"I'm here to confirm she went through with it. So, I'll just sit here and say nothing." Val smiled broadly, trying to reassure Jeff as best she could from behind her dark shades.

"Ok...let's do it. Just tell--"

Val nodded and tapped on the tablet. The car slowed and turned down a side street before parking in an empty parking lot in front of a few businesses closed for the night. Marco left the car idling.

Cassie unbuckled her seatbelt and leaned towards Jeff. She unbuckled his seatbelt, then his belt. He leaned back in the seat as she undid his pants and unzipped him. She slid her hand into his pants and pulled his flaccid penis out, squeezing it gently and pulling it slowly trying to make him hard.

"Can I...touch you?"

Cassie sighed, she knew this would be more than a hand job... She forced a smile, "Sure. Just my top though, ok?"

"Sure!"

His hands were instantly on her breasts. He roughly pushed the bra aside and groped her, squeezing her boobs as though trying to weigh them by touch.

The fondling did the trick and his cock stiffened in Cassie's hands.

She continued stroking him with one hand while she teased his balls with the other. She felt his cock spasm when she took hold of his balls. She stroked them underneath, teasing him with her fingernails.

Jeff leaned forward and took her left nipple into his mouth, suckling and roughly biting her.

Cassie was conflicted. She felt used and humiliated. This was so degrading--making her practically beg to get used like this. To let a total stranger maul her and fondle her.

But, she was very wet. Whatever her conscious thoughts, something deep down was awakened and responding. She couldn't deny she was getting off on this. And knowing Val was sitting there watching somehow made it even more slutty and exciting. She was like a whore and Val was her pimp.

She kept working his cock and felt it twitching under her touch. That and his ragged breathing told her he was getting close.

He leaned back in the seat and spread his legs a bit to give her more access. She kept stroking him, changing tempo to longer, slower strokes and teased his balls more intensely, rubbing them in small circles.

He exploded, his cum firing upward an inch or so in a few bursts, landing on his cock and around the base.

Cassie pumped him a few more times, then wiped her hand on her thigh, spreading a line of his cum across her dress.

She saw Val pointing and gathered as much of his cum with her fingers as she could and wiped it on the dress as well, leaving a sizable stain on the fabric near her thigh.

Val nodded approvingly and handed Cassie a few hand wipes. Cassie took them and wiped Jeff's cock clean and helped him get dressed.

Val tapped the tablet and Marco drove off.

Jeff had just finished fixing his clothes when the car arrived at the bar where he was due to meet his girlfriend.

Marco opened the door and Jeff stepped out. His girlfriend greeted him with a kiss and didn't seem to notice his rideshare companions. Jeff tried to wave goodbye without alerting her.

Marco closed the door and drove off to pick up the next customer.

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The next pickup was a guy on his own named Ken. He was a thirtysomething, well dressed guy heading for a restaurant across town.

When he got into the car, he looked slightly annoyed.

"I thought this ride was me only"

Val replied, "it's kind of a special service tonight and no charge--"

"Whatever...as long as I get there. It's not what I was paying for."

Val smiled crisply, trying to shift the conversation. "Maybe my friend can make it up to you?"

He glanced at Cassie, then back to Val. "I doubt it. What is this like a gentleman's club promotion or something? Some kind of scam?"

Val looked stung. "No. My friend here lost a bet and--"

"Look. I just want a ride. Just a quiet ride. You two do your bets or whatever with someone else."

"Would you like to see her tits?"

Ken said nothing. He took out his phone and made a show of actively ignoring them.

Val pursed her lips, looking annoyed and a bit surprised. Her eyes met Cassie and she just shrugged.

Cassie felt even more humiliated by his rejection than by being used earlier. To be offered up to this guy who just flatly turned her down...

Marco dropped him off a few minutes later.

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The next pickup was a young couple in their twenties. Enrique was a clean cut, nicely dressed guy who looked like he worked out. Becky was every inch the rock chick with a few tattoos, semi-tousled long black hair, jeans and shirt black leather jacket.

Val started her pitch and Enrique politely declined the offer.

But, Becky looked intrigued and jumped into the conversation.

"Ok...so you"--pointing at Cassie--"lost a bet. And you"--pointing at Val--"are like...helping make sure she does it...like an enforcer or something."

The two women nodded.

"That's hot." Becky licked her lips, thinking.

"Ok...so...if I let you give 'Rique a hand job. Can I make out with you while you do it?"

Enrique looked mortified, "Beck, I don't think--"

"Shhh. What do y'all think?"

"Sure. The only rule I have is that I can only use my hands to get him off."

Becky smiled broadly and turned to her boyfriend. "Come on...it'll be fun. You'll get to watch me make out with her...I know it's not quite a threesome...but come on?"

Enrique was bright red. But, Cassie noticed a growing bulge in his pants...

"Ok," he said after a long pause.

Val tapped on the tablet and the car changed course.

Becky kissed her boyfriend and helped him out of his clothes, leaving him only in his shirt and socks. His penis was enormous--at least 8" and very thick. Cassie noticed he was completely hairless around his cock and balls. Becky briefly kneeled on the floor and gave it a few long licks, making it even harder.

Cassie reached for his cock and Becky gently took her hand and said in a singsong way, "not ye-et. Let's give him a show first."

She sat next to Cassie and began kissing her, their tongues sliding against each other as Becky began trying to unzip the dress.

Cassie helped and quickly had the dress off, leaving her wearing only the revealing bra and underwear. Becky slipped out of her clothes and embraced Cassie, French kissing her passionately and cupping her breasts.

Enrique reached for his cock and began to stroke it when Becky suddenly turned and slapped his arm.

"No no no! Just watch. She'll play with you in a minute."

Enrique groaned, but set his palms down on the seat, his cock fully erect and pulsing in desperation, craving attention.

Becky took her time. After a long, passionate kiss, she began kissing her way down Cassie's neck before pulling her breasts out of the bra and gently massaging them with her hands as she kissed, suckled and softly bit each nipple in turn.

Cassie loved the feeling of her mouth on her. Her touch and tongue were magic, making her skin feel like she was being teased with electricity. Each caress made her want more. Her touch was heavenly and made her want more.

"Now, 'Rique, what would you like to see?"

He turned bright red from embarrassment and stammered, "uh...uh...whatever Becks. It's really hot."

"You gotta say it. What do the girls in your favourite porn videos do?"

He looked down at his feet and there was a brief silence. Cassie was embarrassed for him and saw Val grinning across from her, obviously enjoying his discomfort as much as Becky was.

"Um...you know...licking and stuff."

"So should I lick her pussy, ass or keep sucking her tits?"

"Well...um...pussy would be hot."

"You heard the man. Can I eat you out?"

Cassie giggled. Becky had made this weird situation even stranger. She couldn't believe how confident and nonchalant she was about all of this.

"Ok."

Becky got onto the floor of the limo facing Cassie and spread her legs.

Cassie leaned back, trying to make herself more easily accessible to Becky.

Becky leaned in and spread open her lips with her fingers, holding her open and then licking her sloppily.

"Mmmmm...she tastes amazing'Rique...super sweet."

She slid two fingers inside Cassie, making an exaggerated show of collecting Cassie's juices on her fingers.

She raised her fingers towards Enrique's mouth, "taste this. Open up."

Enrique opened his mouth slightly and Becky slid her fingers inside. He pursed his lips, suckling them clean.

"See? Sooo yummy!"

Cassie looked at Val who's expression was a mix of incredulousness and just holding herself back from laughing. Only her dark glasses helped hide her expression a little.

Becky withdrew her fingers from his mouth and focused on Cassie. Her expert tongue quickly had Cassie squirming and grinding against her lips. She moaned softly, cooing in pleasure as Becky focused her tongue on her clit and reentered her with her fingers.

Becky used her free left hand to gently guide Cassie's hand over to Enrique's cock. Cassie began teasing it with her nails, stroking it gently from bottom to top, detouring to tease his balls.

Cassie had never been in a threesome before. Was this even a threesome? Or was it something else? Either way she was enjoying it and Becky knew how to please with her tongue. She was getting close...

As Cassie's moaned became more desperate, Becky focused on her clit. She suckled it between her lips, using her lips to bounce on it while her tongue kept changing direction.

Cassie exploded, her body going rigid as she came loudly, holding the back of Becky's head, pulling her tighter against her pussy, not wanting her to stop or move. It was perfect.

As the pleasure subsided, Becky pulled away, pausing to place a soft kiss on her labia before sliding on the floor in front of Enrique.

"Now, 'Rique, let's give the nice lady a sperm sample, shall we?"

Cassie was stroking his cock with her hand in long steady strokes. Becky leaned forward and began licking his balls, taking them in turns into her mouth and making exaggerated popping sounds as she released them.

Enrique was about to cum from the attention of the two women after the show. As Cassie pulled down on his cock, Becky took the tip into her mouth and Cassie pumped him into her waiting mouth.

Val suddenly spoke, "Wait, Becky! Don't swallow that! She needs it to complete the bet."

Becky made a show of not swallowing and pointed at her cheeks.

She raised herself up and put her face above Cassie's, waving her fingers about to get her to open her mouth.

Cassie figured out what she wanted and opened her mouth. Becky leaned down and kissed her again, letting his cum leak onto Cassie's tongue before breaking the kiss and pulling away.

Cassie picked up her dress from the floor, laid it on her lap and drooled the cum onto the hem, quickly smearing it around so it wouldn't drip off.

Everyone got their clothes back on as Marco drove on to their destination after a quick message from Val via the tablet.