The Ride

Jenna could feel the cool evening breeze on her wet face...and her wet pussy. She felt bad for Matt, leaving him there. But she'd agreed to do what Jared asked now. So, hoping none of the neighbors were out, she made her way out to the limo in the sluttiest outfit she'd ever worn. As she walked to the car, her pussy lips rubbed together, her breasts bounced under the tight top, and that pom plug wiggled and jiggled with every step. It all made her even wetter.

She opened the door, climbed into the back and mulled over Jared's "present yourself" command. Jared loves ass and pussy, she thought. She positioned herself face down, her breasts pressed to the carpet and her ass up towards the back seat.

She didn't have long to wait. Jared slid in, gave her ass a soft smack, and then two of his fingers were buried in her cunt. Then the door slammed shut and Jenna could hear the privacy glass sliding down. She raised her head to cover herself or change positions but Jared smacked her hard on the ass again.

He paused, then spoke, an alpha-bass under his soft command, "Slut, you do not move until I say."

"Yes sir," Jenna whimpered.

Pulling out his wet fingers, he smacked her ass again and said, "Now get over on that seat where James can see you well. Pull those knees up to your shoulders, show us that wet cunt, and play with yourself until I tell you to stop."

Jenna quickly obeyed, fearing another burning smack. She climbed up onto the bench seat and lifted her feet toward the ceiling, spreading her legs wide and bringing her knees back to her shoulders. She could feel James' eyes on her private parts - as Jared commanded - all wet and on display. She began to slowly rub her fingers up and down her wet pussy - rubbing the clit, over her bare lips, two fingers into her hole, out, up, and over again. The pom-plug wiggled obscenely in her ass.

"Thanks for the show, boss," James said without taking an eye off Jenna's wet sex. "Where to?"

"Colonial and Bennett," Jared said. "We've got more winnings to collect."

As the privacy glass rose again, Jenna wondered what that could mean. Fifteen minutes and two orgasms later, she found out. Jared tossed a bottle of water over onto her seat and told her to relax while she waited. Then he exited the car. Jenna rearranged herself more properly, crossed her legs, and waited. Maybe 10 minutes later, Jenna heard the front passenger side door open and close again, some muffled conversation, and then a minute or two later the privacy glass rolled down again.

James looked back and said, "Maybe I'll get you next, mami... this one's real good though."

Jenna could just make out a red ponytail peeking into view at the top of a rhythmic bobbing in James' lap. He's getting a blowjob, she realized. It must have been good. After about three or four minutes James was thrusting and groaning. Jenna was transfixed... Suddenly the door opened and she turned to see Jared. She turned back to the front to see James grab the red pony tail and shove it down, out of view, into his lap.

"Now, there's your partner for the weekend. Real slut." Jared noted. "Great cock sucker, as James is finding out. But here she comes."

Jenna turned to see the privacy glass ascending then turned again as the back door opened and the woman stepped in. She was striking: pale skin, red hair, green eyes, full lips. She was also wearing a light blue version of Jenna's outfit. As she climbed in, Jenna took in the details. Same wedge sneakers, crotchless shorts too. The woman looked Jenna in the eye, licked a dribble of cum off her lips, and wordlessly arranged herself face down, ass up towards Jenna. She couldn't take hereyes off her plump lips and a trimmed tuft of red pubic hair above. Her breasts were slightly larger than Jenna's and were barely contained by the top. And she had a full peach of an ass, with a similar pom-pom between her cheeks.

James closed the door and Jared spoke. "Well, all set then. Jenna, this is Renee, an...acquaintance of mine. Works at a neighboring firm in town. She's paying up with her body what her pencil dick boyfriend couldn't with cash. Isn't that right, Renee."

"Yes, sir." She quietly replied.

"Now, Jenna, I think Renee here deserves a reward. Unlike you, her current predicament isn't her own fault. And, for God's sake, look at that delectable peach! Looks good enough to eat, don't you think?"

Jenna stared at Jared for a moment, until he gestured towards Renee's ass with a smile. "Yes, sir," she said.

Slowly Jenna leaned forward and laid her hands on Renee's ass cheeks. She slipped to her knees on the floor, Renee's soft calves brushing the inside of her knees and thighs. She wrapped her fingers around the base of the pom-plug. As she began to slowly pull it out, Renee moaned softly. Hers was different: a pom-pom connected to five balls - about an inch and a half diameter each one. Renee's asshole slowly distended then shrank back as each ball popped out. By the second, Jenna had begun running her tongue softly around Renee's asshole and slowly rubbing her thumb in circles over Renee's clit. And, as the last bead broke free of Renee's tight ass, Jenna set to: tonguing Renee's holes and lips and sucking on her clit. And Renee's moans and grunts continued, increasing finally to a hoarse begging to stop as wave after wave of orgasm rolled over her.

They did stop, finally, after about 15 minutes. Jenna's face was wet with Renee's sex and Renee's face was panting on the carpet.

"Good show, girls!" Jared laughed. He sighed and sank back into his seat. "Probably time for a costume change, wouldn't you say?" He waved a hand beyond them toward the privacy window. "Over on the far seat is a box for each of you."

Renee lifted her head from the floor and obediently began to crawl toward the boxes. Jenna's eyes were transfixed for a moment on Renee's wet asshole and the strawberry flush of her pussy lips pressed between her pale ass cheeks. Then, anal beads in hand, she too began to crawl over.

Renee and Jenna knelt side by side before the boxes. Her thigh pressed gently against Renee's creamy skin. They opened the boxes slowly. Inside were identical outfits. Renee lifted out a tiny plaid skirt. Two words came to Jenna's mind: "schoolgirl" and "porno". For the next few minutes they awkwardly undressed and then redressed: a tiny, cap sleeve dress shirt that didn't even cover Jenna's nipples, with a tie that rested between her breasts, and the skirt which barely covered half her ass, and a pair of clear stripper heels, even a pair of glasses. There were no panties.

"Good work, girls," Jared said once they were dressed. "Now, box up those cheer outfits. Those we'll need for tomorrow's festivities. Oh, and Renee, if you'd be so kind as to remove Jenna's plug, you can box hers and yours up along with everything else."

Jenna looked at Renee and then turned to her left, laid her face and tits down on the seat. As Renee leaned in and rested her left hand on Jenna's ass, Jenna could feel Renee's right hand tracing up her thigh towardher pussy. Renee slowly pressed her thumb in between Jenna soft lips. Jenna breathed out heavily, and then Renee began to slowly pull the plug out.

"Damn girl," she said as ridge after ridge stretched her hole until finally the head popped out, leaving her gaping slightly. "You're a sick fucker, you know that, Jared?" Renee said.

"Aww shucks, thank you. I already know you both enjoy it and we're going to prove that out plenty in the next two days. So, shut your mouth and both of you crawl over here..." Jared pointed to the floor at his feet.

Renee tossed the plug into the box. Both girls made their way over and knelt in front of Jared's knees. He lifted a smaller box off the seat next to him and into his lap. Taking off the top, he smiled. Inside were two classic, jewel butt plugs - large blue jewels, thin metal stem, and a metal teardrop maybe 1.5" at its widest.

"As I told your dumb cucks, your holes are mine this weekend. Or I suppose they could pay up what I would have paid. Barring that, I've got a lot in mind. And, what can I say, more than anything else I love anal play! Now show me those lovely asses!"

The girls glanced at one another and dutifully assumed the position again, turning on their knees, faces on the floor, asses in the air.

"Grab those cheeks and spread 'em, ladies," Jared said softly.

Jenna and Renee reached back simultaneously, fingers reaching around and pulling their ass cheeks apart. Jenna's eyes widened a bit as she felt Jared slide a lubed finger into her ass. Seeing the same look on Renee's face, Jenna assumed she was getting a fingering too.

"This is really some great lube," Jared said. "It's going to serve us well..."

Then, as Jared's finger withdrew, Jenna could feel the cold steel pressing into her hole, stretching it wide. Renee's mouth made an "O" and her eyes rolled back into her head. The plug stretched her wide and then Jenna felt her ass close over it as the jewel snugged up between her cheeks. Jared smacked their asses hard once and then tossed what seemed like a coat onto each one of them.

"Put those on, now. We need to get in to stage two but I can't have the fine ladies and gentlemen of the Four Seasons thinking you're hookers, now can I?"

Jenna smiled at Renee as if to make the best of it and rose up to kneeling again. Jenna slipped on the coat, and moved to the seat. It barely came mid-thigh sitting down. She thought "hookers" was exactly what any thinking person would see in them. Renee was on her knees now, and Jenna helped her get her arms into each sleeve. Renee turned and leaned in and Jenna felt Renee's fingers tickling her bare pussy under the coat.

She whispered, "I'm going to return the favor soon..." Then she kissed Jenna on the mouth as the car came to a stop.

"Here we are! The Four Seasons! Follow me ladies." With that, the car door opened and Jared stepped out.

Renee exited first. As she stood up, Jenna could see the black raincoats were indeed very short, just covering Renee's ass - if you weren't below it. Jenna swung both legs together out the door, keeping her knees together and her bare pussy covered as best she could. Then, offering each girl an arm, Jared led them into the hotel.