Simon was bored. He had the day free, but none of his friends were about, so he was just rattling about the house. Even the staff had the day off. And it was even one of those perfect Los Angeles days—not a cloud in the sky, warm but not hot, a light breeze—that made him vaguely irritable. A man needed something rough to rub up against, to know he was alive. Life here was all too easy.
The doorbell rang, odd since he hadn't heard anyone from the gatehouse for the community phone up, but anything was better than just sitting and waiting for something to happen. Perhaps this was that something. He opened the door and standing outside was a young lady in a stereotypical cheerleading costumes—leeveless top, short pleated skirt and trainers. Her light tan contrasted with two heavy yellow braids and a wide, toothpaste-white smile. "Mr. Cowell?" she chirped.
"Yes?" Simon replied, non-committally as possible.
"We're washing cars to raise funds to send our squad to the state championships," she said.
"Shouldn't the football team be paying for that?" he asked. "Or basketball or whatever it is you cheer for."
"No, these are our championships. The cheering championships."
"Ah, I see. You must have a very good team, then."
"Squad, and yes we do. We're the best!" she shouted, and punched up one arm for emphasis.
"I can see that," Simon replied. "Well, I have someone professionally wash the cars—finicky finishes and whatnot—but I'm happy to make a donation."
"We're really supposed to work for it," the girl said. "Can't get something for nothing. Do you have an old car around?"
Simon regarded the girl, who couldn't be more than sixteen, and wondered what high school organization could possibly think it was a good idea to send young girls door to door performing household tasks, but it wasn't his place to question. "Very well," he said. "I know just the thing, actually. Did you bring"
"Yep! Just over here," she said, and went back down the walk way. She bent over at the waist to pick up the pail, giving him an excellent view of her tight little arse, encased in bright red knickers that matched her uniform.
Matching panties, he thought, and smiled. "Just this way," he said, closing the door behind him. He led her over to the car port that sat next to the garage, as though the house was a restaurant that needed a roof over the walkway between the driveway and the front door. "One moment, let me pull the car out for you."
The blue Honda still sat in the back corner of the garage, under a cover but still dusty with disuse. He wasn't entirely sure that he'd be able to move it, but for once the engine started right up, and he carefully backed it out past the various luxury cars and into the driveway. The girl had found the hose, apparently, and was filling her bucket with soapy water. "Wow," she said. "That's kind of an old car.
"Yes, but I'm very sentimental about it," Simon said, "so do take care."
"Maybe you should supervise me, then," she said, smiling. "You know, just to make sure I don't do anything wrong."
Simon raised an eyebrow, but she did have a point. "All right," he said, sitting on a nearby garden bench and lighting up a cigarette. "What's your name, by the way?"
"Rhiannon. You know, like the song?"
"Ah, yes," Simon said.
Rhiannon got started on the opposite side of the car, facing him, her brow furrowed in concentration as she made careful overlapping circular passes with her large sponge. She was certainly meticulous, starting at the top and working her way down, rinsing as she went so the soap had no chance to dry on the paint. She even had a squeegee for the windows. She stretched to reach the roof, one foot out in the air behind her, and as she scrubbed away Simon couldn't help but anticipate how shed look when she got around to his side of the car and he could watch her from behind.
Well, that was why these cheerleaders washed cars rather than selling candy or similar, wasn't it?
There wasn't that much that could be done for the poor old car, and it hadn't been that dirty, but Rhiannon conscientiously scrubbed away every hint of grime and dust that the Honda had picked up during its stay in the garage. As she made her way around the trunk and to Simon's side of the car, she made just as pretty a picture as he'd hoped. Her uniform was wet and clinging to her body, and her pleated skirt was making little effort to cover her bottom as she bent and stretched over the car. "Lovely," he muttered under his breath.
She probably was teasing him just a little—he sensed a wiggle here and there—but she was also innocent, almost wholesome. Which, of course, just made him want to debauch her even more, though he was trying to stay safely on his bench and not risk any unfortunate incidents.
Rhiannon was reaching up to wash the roof when the sponge slid out of her grasp and into the center of the roof of the car. "Oops!" she said.
"I can get it," Simon said, knowing that being that close to the girl was likely incredibly unwise but not being able to help himself. He walked up behind her, pressing her against the car with his weight as he reached past her to get the sponge. "Here you go," he said, handing it to her.
As his arm came down from the roof it brushed her head and suddenly the yellow braids went splat, off her head and into the bucket of soapy water.
The girl—although she was looking a bit less feminine now—gasped and her hands flew up to her head. "Oh no!" she said.
Simon set the sponge down and stared at Rhiannon. "You're not a girl, are you?" he asked.
She—rather he—shook his head.
"Are you even a cheerleader?"
"There are male cheerleaders!" he said, and his voice was deeper now. "We lift the girls and sit at the bottom of the pyramid."
Simon raised an eyebrow. "And you wear skirts?"
"No," the boy replied. "But we can make more money this way."
Simon couldn't help smirking. "So you were teasing me, with all that bending over."
The boy shrugged.
"And what is your real name?"
"Ryan," he said. "It's Ryan."
"Well, Ryan, I'll make you a deal. You can rinse off the car, and I'll pay you the going rate with a generous tip, and even help you put your wig back on straight and you can be on your way. Or ..."
"Or," Simon said, stepping closer, "you can stop the teasing, bend over this car, and let me fuck you in that tight little bottom of yours."
Ryan's eyes flew open. "But I ... I never ..."
"Mmm, a virgin?" Simon asked, rubbing his lip with one finger. "How delicious. How old are you?"
Ryan pushed his shoulders back and tossed his head. "I'm eighteen."
Simon chuckled. "I'm sure you are. Well, what do you say, then?"
"I'll do it," he replied, "if you'll kiss me."
"Of course. We needn't be barbarians. Just wait right there." Simon walked into the garage and went immediately to the glove box of the BMW, where he was sure there was some lube and a condom or two from a recent car sex misadventure.
Satisfied, he returned to Ryan, who hadn't moved an inch, so he rewarded him for listening so well to instructions with a kiss. Ryan was tentative, to be sure, but able and willing, and while Simon had firm control of the kiss Ryan was right in there with him, his hands clinging to Simon's shoulders. Simon's hands moved down to grab that firm bottom that had been teasing him for the last hour and in response Ryan pressed his body firmly against Simon's, his erection evident even through the layers of fabric between them. Obviously those layers needed to go as soon as possible.
"Right," Simon said, pulling back. "Lean over the car."
Ryan assumed the position, his hands braced on the hood of the blue Honda. Simon lifted up the skirt and ran his hand over the rounded flesh, covered in the red panties.
"Spread your legs a bit, please," Simon said, then pulled the uniform pants down from the waistband, leaving them around Ryan's upper thighs so that tight, virginal arse was perfectly framed by the skirt and pants. Simon's hands trembled with anticipation as he squeezed lube onto his fingertips and placed them on that entrancing little entrance.
Ryan gasped and arched his back, pushing his arse out further.
"You're a natural, darling," Simon said. "You were made for this." He slipped one finger in and felt Ryan's arse grab at it, almost pulling it in. "Ever played with yourself? Put anything up this pretty arse of yours?"
"Just fingers," Ryan said.
"But you want more."
"Yes," he hissed.
"Is that it?" Simon asked, rubbing the spot he'd found again.
"Oh god," Ryan whispered.
When Ryan had calmed a little Simon added another finger, and eventually another, squirting even more lube onto his fingers until Ryan's little hole was stretched and waiting for him. He wiped his hand off on the sponge, then pulled the condom out of his pocket. He unzipped his trousers, rolled the condom on, and applied more lube.
Ryan turned, watching Simon over his shoulder, and gulped, though there was a hungry look in his eye.
"Don't worry," Simon said, smiling. "I'll be gentle." He held onto his cock with one hand, Ryan's hip with the other, and slowly slid into that tight, wet heat.
Ryan moaned, closing his eyes and dropping his head, but he was also pushing back toward Simon, arching his back even more.
"That's right, darling," Simon said. "I told you, you're a natural. Relax and push, that's right."
"So ... full," he said.
"Better than fingers?" Simon asked
"Good. I'm going to move now," Simon said
"Please," Ryan said, and dropped down to his elbows, cradling his head in his hands.
Simon began to thrust then, first slow and shallow but gaining speed and depth until he was properly fucking Ryan. The boy was taking it like he was born to it, pushing back against Simon and moaning low and sweet in his throat and making it so, so good—better than Simon had expected. He reached around and took Ryan's hard cock in hand. It was a little wet from where it had brushed against the car and Simon put that bit of water to good use, stroking Ryan firmly in time with his thrusts, wanting to give him everything, make this first time as good as possible given that Ryan was being fucked up against a car.
"Oh god," Ryan said. "Gonna, gonna ..."
"Go ahead," Simon said. "Come for me, Ryan. Come with me inside you."
Those words did the trick, apparently, as Ryan shuddered and came, spraying the car and clenching his arse tight around Simon's cock.
Simon put his hands on Ryan's hips and began to pound his limp body, selfishly seeking his own pleasure, and Ryan let him, bracing himself against the car until Simon finally came, then collapsed on top of him.
"Out of breath, old man?" Ryan asked.
"Not a bit," Simon said, though he was. He pressed a kiss into Ryan's shoulder, then pulled out of Ryan, carefully disposing of the condom in the outside bin. He tucked himself away and sat back down on the bench to light a cigarette.
Ryan stood as well, dropping the pants to the ground. "So, you like the outfit?" he asked, twirling such that the skirt flew up and Simon glimpsed Ryan's cock, which he'd felt but hadn't seen.
"I do," he said. "But before you change"
"You'd better wash that stuff off the car," he said. "The owner wouldn't be pleased to find a come stain on his fender."
Ryan rolled his eyes. "Shut up, you," he said, and threw the sponge at Simon's head.