Chapter 1

Cheshire Alicia Smithson was in tenth grade, at Altamont High. She did well in school, nothing outstanding ... she was there every day, at least. And she tried, though she was no rocket surgeon. She got by.

Cheshire was finally having a burgeoning interest in the opposite sex. It went, as was her fashion, in fits and starts. At the moment, it was on again.

Cheshire had gotten her cherry popped a few months ago, at the tender hands of the Altamont High Casanova himself, Ralph Ready. Ready Ralph had single-handedly whittled the number of available virgins at the school down to a manageable size. He followed Cheshire home one afternoon, wooed and schmoozed her, and left with another notch in his gun. Cheshire still loved him a little bit, although she now realized that he was a womanizing jerk. He never came back for seconds, although she let him know it could happen. The thrill was in the chase, for Ralph.

Cheshire was a fox, and she knew it. She had grown up very nicely. She was built like the proverbial brick shithouse, in that fashion that only teenaged girls seem to possess for a few brief years. She wasn’t worried, though, she just looked at her mother, and was pleased. I chose my genes wisely, she thought. Her mom was built, and still looked good. Her mom held her thirty-eight years well. Cheshire had long dark blonde hair, and dusky features. Her lips were full, puffy and naturally red. She was that rarest of creatures, a brown-eyed blonde. She was truly beautiful, and she knew it. She hadn’t taken advantage of her looks yet, but it could happen. The right opportunity just hadn’t arrived yet.

Cheshire lived with her mom. Just the two of them. Her mom slaved away, sixty hours a week for peanuts, but somehow they survived. Money was tight. Cheshire looked with envy at the rich kids in school. The stupid bastards. She hoped they appreciated what they had. Life sucked, when you were poor. I am not gonna be poor my whole life, she told herself, time and time again. She just hadn’t figured out how to change it, yet.

A boy at school liked her. And, better yet, he was a rich kid. He had a hard-on for her, bad. The only real problem was, she didn’t like him very much. He was a spoiled brat. And he was a lazy motherfucker, she’d been in a workgroup in a science class with him, and he didn’t do shit. That one experience with him was really the main reason she disliked him so much.

One day she was at her locker, and he walked up. His name was Larry. Leadbutt Larry, she called him in her head. He smiled his sunniest smile, hoping to sweep her off her feet. He never gave up hope.

“Hi, Cheshire ... you are looking fine today...” he said. Oh shit, she thought, don’t fucking start it.

“I look fine every day, Larry,” she snapped, tossing her books into her locker and slamming it.

“Cheshire...” he was almost whining. Jeezus. “Nobody’s home at my house. Come home with me. We can watch the bigscreen and eat Doritos. Please?”

All that, and he begged, at the end. Sad. She sighed. Doritos were her favorite, though. The bigscreen was no big deal, her and her mom were poor, and they had a bigscreen. Who the fuck didn’t nowdays?

“Larry...” she started to smash his spirit with a witty quip, and then she thought ... shit. So what. What else do I have to do today? I’m free until six, when my mom comes home, and I don’t even have to be home then. Why not, why the fuck not? Let’s see how the other half lives.

She knew already how the other half lived, her best friend Vicky was rich, and Cheshire had stayed with her in her palatial mansion often enough. I mean, damn ... they even had a special room just for wrapping gifts. A whole room, just for wrapping shit. Fuck.

“Okay, Larry,” she said. His jaw dropped in shock. “Impress me.”

He hemmed and hawed around so much she wondered if he would have asked if he’d known she’d say yes. She wondered if anyone had ever said yes to him before. Probably not, judging from his reaction. She followed him to the parking lot, and let him seat her in his Challenger. Stupid goddam rich kid, she thought, as he walked around the car to his side.

She was right, it was a mansion. It put Vicky’s to shame, even. How did these people manage? she thought. She would like to know their secret. Larry hit the opener, and parked the car, and they entered the house through the garage. It wasn’t that great inside, there was shit everywhere, and the rugs could have used a good vacuuming. What the hell, she thought, rich people are people too, I guess.

Larry got her settled in the living room, and then went and fetched some chips and soft drinks. Excellent, she thought. Plain Doritos. My favorite. None of that powdered cheese shit. They munched chips for a while, while Larry thumbed through the channels. Shit. Two hundred channels, and nothing interesting.

Larry was a nerd. A geek. Cheshire knew that, and accepted his geekdom. She was just here to kill a few hours. This didn’t mean anything to her.

Apparently it did to him. He moved closer and closer, reminding her of a shark, approaching a helpless Australian swimmer. She got ready to spank him down.

“Cheshire...” he gushed, “you are the most beautiful girl in Altamont. I can’t believe you came home with me...”

Believe it, she thought. And yes, I probably am close to the most beautiful.

“Darling ... would you consider...” he gulped, summoning up his courage. Oh shit, she thought.

“Would you consider being my girlfriend?” He looked panic-stricken, like his mouth had said that without his consent. Crazy, she thought.

“Larry, my little friend,” she said. “I am a free agent, bound to no man. I will be your friend, yes, and I am a girl, thusly, I am your girl friend, probably not in the fashion you wish, unfortunately. Sometimes you must take what you can get, and be happy.”

He nodded as if she’d said something profound. He almost looked relieved. She glanced down, for some reason, at his crotch. She was stunned to see something in his pants, pushing the cloth of his slacks outward. My god, she thought. I’m doing that to him. I’m doing that for him. Me. It gave her a warm fuzzy feeling, and very nearly a case of the giggles, at the same time.

“You are my best friend, Cheshire,” he said fervently. She was embarrassed for him.

“Well,” she said. “I’m glad we got that out of the way...”

“Cheshire...” he wasn’t finished. Shit. More sloppy emotional stuff would follow, she knew.

“Cheshire ... I’ve never had a girlfriend before...” he said. You still don’t, she thought. She was polite, though, and kept her mouth shut.

“I’m ... I’m still ... I’m still a virgin...” he embarrassingly confided, and she felt embarrassed for him. She almost even felt a little sorry for him, that it meant so much to him that he’d risk embarrassment of this magnitude, just to tell her. I mean, she thought, what if I laughed? I could fuck him up for life.

“Larry,” she felt a little kindness towards him, oddly. “It’s not that big a deal ... I know lots of virgins...”

He seemed to burn with shame, and put his head down.

“Easy to say...” he said, and she thought ... yep, it’s easy to say.

Cheshire had been raised by her mom, in a thoroughly modern fashion. Her mom hadn’t placed a lot of limits or constrictions on her. And certainly no old fashioned stuff ... maybe a little bit not enough old fashioned stuff. Cheshire had a thought, about this time. A little thought, that grew into a big one. What if, just what if ... she thought. Would I really do that? Will I? Let’s just see...

“Larry...” she said softly, and he turned on the couch and faced her.

“Larry, how much cash you got?” He gulped and almost frowned. Oh shit, she thought, what if he calls me a whore and I have to walk home...

He didn’t seem upset, though. He pulled out his wallet, and spent a few seconds counting. The longer he counted the more Cheshire got pissed. These fucking rich pigs and their money, she thought. It serves him right if I take a little.

“Two hundred and forty dollars,” he finally said. Shit, she thought, what’s a fucking kid doing with two hundred forty dollars in their billfold? What the fuck?

“Larry,” she said hastily, before she lost her nerve. “I will fuck you for two hundred dollars. But you can’t tell anybody it was me. You just have to say ‘some girl, ‘ or something like that when you tell your friends. Got it?”

He just stared at her, his mouth still open. She wondered if it was worth two hundred dollars to him. She knew that rich people were usually tightwads. But she had something he wanted. And, she thought, I’m worth two hundred dollars. At least two hundred dollars.

“Blug,” he finally said, or something similar. “Cheshire ... I love you ... yes, yes, two hundred dollars ... here...”

He was waving the money at her. That was embarrassing, and she was glad nobody was around to see his humiliation. The thought did occur to her, about that time, what exactly that made her, too. She shut that out of her head. She would have time for introspection and possible regrets later. Now, she had work to do. She grabbed the cash and stuffed it into her pants pocket.

“Where?” she asked, and he stood, and led her to his bedroom.

“Lock the door,” she said. He locked it, but felt obliged to explain the situation further.

“My folks are on a cruise,” he said, “My big sister is checking on me every now and then.”

Shit. She surveyed his room. It was as big as her living room. The bastard. He had his own bigscreen even. The little fucking bastard.

He just stood there, waiting on her. She realized that he was such a suck-up that she was totally in charge, from here on. It was up to her to set the pace, to call the shots. He would probably turn himself inside out and jump up his own ass if she told him to.

“Drop ‘em, Larry,” she said, and he gulped and gazed at her.

“Your clothes. Take them off,” she said, and he nodded.

“Yeah,” he said, and in moments, he was down his underwear. He stopped, waiting on her. Well, shit, she thought. Time to pay the piper.

She slowly dropped her pants, asking herself if she was sure she wanted to do this. For two hundred bucks? Herself answered. Hell yeah. Okay, got that out of the way. She kicked her shoes off, and slid her panties down her legs, and stood before him. He sucked in a ragged breath. She knew she probably looked cuter than shit, standing there bottomless. She wondered if he could hold it until he was in her.

He did, somehow. He finally dropped his shorts, and she got a first look at his manhood. Not exactly awe-inspiring, she thought. Well, she’d hoped for another Ralph. Too bad. He was probably just basically normal, she thought. His cock was almost embarrassingly hard, it was damn near purple. She hoped it didn’t explode.

“You gonna...” he said, his voice rough, “you gonna take your shirt off?”

I’d rather not, she thought, but hell, he paid his money. She unbuttoned her shirt, and dropped it. Her bra followed. She felt nice and sexy and naughty, to be naked in front of him. He didn’t really turn her on, but she felt good, anyway. Her boobs felt good, she thought, to be out of that goddam boobcage. She absently scratched underneath them, and his dick got a little harder.

“Well!” she said brightly. “Let’s get to it!”

Forty five minutes later, she was positively bored. She lay on her back, on top of his bed, and he lay on top of her, in the old tried and true missionary position. He was puffing and panting and pumping away, fucking her ferociously, and she was absolutely bored. It had felt good at first, and she’d even cum a little bit, but now, it was getting old. She was wondering when two hundred dollars worth would occur. He seemed to be having a good time, at least. What the fuck, she thought, of course he’s having a good time. He’s getting his dearest wish, he’s getting to fuck a beautiful girl. Me.

He had slobbered and slurped on her boobs for a while, as she fucked him, but he’d finally seemed to get enough of them, to her satisfaction. At least, she reminded herself, and least he’s not a kisser. She didn’t really want to have to kiss him, at all.

“Larry,” she finally said, “Let’s try a change.”

He finally got the idea, and pulled out of her. She rolled over and sat up, on her hands and knees, in the middle of the bed. She motioned for him to get behind her, and he finally got the idea. He slid his hard cock back inside her pussy, and began to fuck again. She hoped the change would make him cum faster, if he was going to cum at all. She was starting to wonder.

She leaned to the side a bit, and grabbed the remote, on a little side table. She thumbed the bigscreen on, and waited a moment for it to light up. He acted like he didn’t even notice, he just pumped away at her ass. Lord, she thought. He’s gonna go all night.

She finally found a talk show that looked interesting, and watched for a while. It surprised her to realize a few minutes later that she was still being fucked. Good grief, let him finish, she thought.

“Larry ... darlin’,” she finally said. “Are you gonna cum, honey?” she hoped that buttering him up might turn him on a little more. It seemed to.

“Cheshire ... darling...” he said, speaking in spurts, as he slapped his thighs against her ass. “It just ... feels so ... good I ... want it ... to last ... forever...”

“Well, shit,” she said. “I got homework, darlin’ ... try to finish, if you can...” She went back to her show. Now there were dwarfs on it. Fucking dwarfs, she thought. Can you imagine. She heard him moan, behind her. He sped up a bit. Good, she thought.

Ten minutes later she was deep in Sally Jessie Raphael. In the most boring shit ever. But, it was something. Good fucking grief, she thought. Am I just going to have to walk away? Is this boy ever going to cum?

“Larry...” she finally said.

“I know, I know,” he said. “I’ll cum, okay...”

“It’s been an hour, my dear. Have a little heart,” she said, and he laughed, slightly. He sped up even more. She returned to the show.

Ten minutes later, she thought, shit. Enough of this shit. It’s starting to hurt, now. Her pussy did ache, a little. He’s got his two hundred bucks worth, and more than.

“Larry. Time to cum,” she said. “The ride stops in two more minutes. Finish it up.”

He sped up one last time, and she heard him moan. Jeezus, he’s a beast, she thought. He’s been going a solid hour. I should have paid more attention, I might have got to cum, myself.

Larry finally pumped a gallon or two of sperm into her body. She even felt some run down the outside of her pussy. Oh, ick, she thought. Hate that shit. All part of the deal, though.

Larry finally collapsed on the bed beside her. He was covered with sweat, and she thought yet again, ick. He seemed exhausted. She was a little tired, herself. It had been a long afternoon. She wondered if they’d set a record, or something. I thought young boys came quickly. I thought they couldn’t hold it back. He was definitely the exception to that rule.

She climbed off the bed, and went into his bathroom. She was about to bust to pee. And she peed, she felt some of his sperm dripping from her cunt, and grimaced. She wiped it up as best she could, but she knew she was full of the stuff. She was glad again she’d gone with Vicky and got the shot. None of that unpleasant baby crap. Better safe than sorry, for sure.

She returned to his room, and began to dress herself. He still lay, catatonic-looking, on his bed, exhausted. She knew how he felt, she was a little tired, too.

“Larry, my friend,” she said, wanting to put him back securely in the friend zone. “Remember you must keep your mouth shut about this, if you ever want it to happen again. If word gets out that I put out you’re shut out, understand?” She hoped that the promise of a possible repeat performance would be enough to get him to keep his mouth shut. She really didn’t want word to get around that she fucked for money, much less that she’d fucked him for money. What I do, she told herself, is nobody’s business but my own.

He had nodded his head thoughtfully as she spoke. She knew he’d probably tell his best friends, anyway. She was sure he’d be proud of finally getting his cherry popped. I just hope he doesn’t write my name and number on the bathroom wall. Well, he didn’t know her number. And he’s not going to.

“Do I have to walk home?” she finally said, and he pulled himself up and began to dress. He drove her home, and, on impulse, she leaned forward and gave him a little peck on the cheek.

“Thank you, Larry,” she said, remembering a witty line from a movie. “It was a business doing pleasure with you.”

He didn’t catch it, of course, he just nodded and smiled. She got out, and he drove away. My first day as an independent businesswoman, she thought to herself, with satisfaction.

Everything went fine until Friday. Nobody said a word, and she was actually thinking that he’d kept his mouth shut. The last bell finally rang, and she was at her locker, in a hurry to get her shit put up and get the hell out of there. Who should walk up, but a kid name Steve Wilson. Oh shit, she thought. She knew he hung out with Larry, she’d seen them geeking around together in the halls before.

“Yes,” she said, slamming her locker. “What can I do for you?”

He seemed a little shy, as Larry had been at first.

“I thought...” he said, and then was silent. Well? she thought. Spit it out. She knew he was getting his nerve up, though. She looked around. At least the halls were pretty empty. Everybody was in a hurry to get the hell out of there, as she was. If not for this nerd. Jeezus.

“I though maybe ... you’d have some time for me...” he said, and her heart sank. That little motherfucker, she thought. He told. The bastard told. Now word is out. Cheshire Smithson plays for pay. Shit, shit.

“Steven,” she said coldly. “I’m not sure what you have been told, but the truth is probably not as much fun as your dreams. If you will pardon me, I need to get home.”

He looked positively crushed. Shit, she thought. A lifetime of therapy, just from this one moment. She felt a stab of sympathy for him. He was a bigger geek than Larry. She knew this kid was a virgin, a virgin to the nth power. This kid would probably die a virgin, unless she took a little pity on him.