Caution: This Erotica Sex Story contains strong sexual content, including mt/ft, Ma/ft, Consensual, Fiction, Uncle, First, Oral Sex, Petting, Prostitution, .
Desc: Erotica Sex Story: Chapter 1 - A high school girl decides to earn a little unreported income.
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.
She sighed, and stared at him. He edged backwards a step at a time, not daring to take his eyes off her. She realized how hungry he looked. She knew he wanted her, bad. And who wouldn’t? she thought. I am highly desirable.
“Steven, Steven,” she finally said. “You got a place we can go?”
And that was the craziest thing of all, she thought. He didn’t. He didn’t have a place to go. What did he think, we were gonna do it at the park? On the playground?
Cheshire felt fairly safe, taking him home. She knew that her mom wouldn’t be home until after six o’clock. They had a little over three hours. She didn’t have much fear that he’d go an hour, even, much less three. Jeezus, the kid didn’t even have a car. They had to walk to her house. At least I’ll be home when I get done, she thought.
Steven obviously wasn’t as wealthy as Larry. She hoped he could at least come up with the ... the fee. The entrance fee. She giggled.
She unlocked the door, and led him in. She took him straight to her room, and shut and locked the door.
“Steven,” she said, “If my mom comes home early, you’ll have to hide underneath my bed until she goes to sleep.” The stricken look on his face made her giggle, and she shook her head, just to let him know she was fucking with him. She yanked her sweater over her head, and unsnapped her jeans, kicking them down her long legs. Oh shit, though. She had a thought.
“Steven, my dear...” she said, unsure how to breach the delicate subject. “Do you have the ... fee?”
He nodded, and reached in his pocket. He pulled out a disorganized wad of bills, and presented them to her. She decided to trust him, and stuck them in her money jar, on the shelf. Her jar was filling up nicely, now, she thought. Two of these guys, on a steady basis ... she would be fixed up.
He was almost undressed when it happened. He was sliding his underwear down his legs, when she heard him gasp, and out of the corner of her eye the saw a stream spray from the end of his cock.
“Oh, shit,” they both said, at the same time. Fuck, she thought. All over the floor. Fuck, what a mess.
He felt bad, and she felt bad for him. He dropped to his knees and scrubbed up the mess with his underwear. She sat heavily on her bed, and watched.
“Honey,” she said, “Don’t worry about it, I’ll take that as a compliment. We’ll just wait a while, and we’ll try again.”
He was almost too embarrassed to meet her gaze. He just nodded, and mumbled something beneath his breath. Shit, she thought. Damn, did I do that? Did I turn him on that much? She felt a rush of raw power. He wasn’t even touching it, and he came. Damn, damn. I rock.
They sat, naked, on her bed, and talked. He was a nice kid, she decided. Nice enough to fuck, at least. And this time, she told herself, this time I’m gonna cum, too. I want something other than just cash from this one.
He had a nice cock, a bit larger than Larry’s. It hadn’t actually even gone down, yet, since he’d came. It was still pretty hard. She idly reached for it, and felt him suck in a breath. She giggled, and stroked it, feeling one in her hand for the first time. That feels cool, she thought. She felt him harden under her touch.
“Steve...” she said, feeling positively wicked. I cannot believe you are going to do this, she told herself. You wicked bitch. “Steve ... relax ... I’ve never done this before, so cut me some slack, okay?”
She slid off the bed onto her knees, and put her face into his groin. She felt his legs trembling beneath her hands. She opened her mouth. Here goes, she thought.
It actually felt pretty cool, she thought. He was pretty hard, again, just getting a blow job from the foxiest girl in school was enough to get him hard again. He couldn’t believe his luck. For a measly two hundred bucks? He’d pay double that, triple that, if he had too. Two hundred bucks was a steal.
She sucked him all the way down to his groin, and then out again. His cock felt comfortable in her mouth, like she’d done it a hundred times before. The cap felt so cool, she ran her tongue around it, and curled her lips on the backside of it. He moaned in pleasure. She was sure it felt good. How could it not?
She sucked hard, and pulled out, to the cap, then plunged it back in again. Until she felt it touch the back of her throat. She almost gagged, but she controlled it. Damn, she thought. There’s an art to this. I’m not sure if I’m doing it right, but he seems to be enjoying himself.
When he came, she was surprised. She hadn’t yet actually decided if she’d take a mouthful of his cum, but he decided for her. Or, rather, his prostate decided. Suddenly, with a twitch, her mouth was full of a slightly bitter liquid. Shit! she thought, shit! She gulped, just to keep from spewing it out, and gulped again when he squirted again. Shit!
He was done, finally. He sighed a huge sigh of relief. She dropped his still-half hard cock in his lap, and sat back up on the bed.
“I should charge you double for that,” she said, and then laughed, to let him know she was joking. He smiled weakly. She breathed in her hand and tried to sniff it, wondering what her breath smelled like now. She had a pretty good idea. She sat beside him, and clapped her hand on his leg.
“Steven,” she said. She felt generous. “We still got a couple of hours before my mom gets home. If you can get it up, again, we can fuck, proper. Want to try?”
“Oh, hell yeah,” he said, overjoyed. Of course he was, she thought. “Cheshire ... you are so beautiful ... I love you, I love you...”
“Now...” she laughed, “Don’t start that love crap. This is a business arrangement, remember?”
“I don’t care,” he said fiercely. “I love you.”
Shit. She sighed. Occupational hazard. Whatever.
She found the remote, and turned on her little TV. Everything sucked, though. She finally settled on the sci-fi channel. They watched TV for a half and hour, comfortably naked. He finally started getting a little frisky, and then politely asked if he could touch her tits.
“Steve, you got another hour to do anything you want. Except butt-fuck me, you cannot butt-fuck me.” She hoped that would make him feel like he was getting his two hundred dollars worth.
“Cheshire...” he said, almost apologetically. “What I really want ... I really want to taste you.”
“To taste me? To eat me out, you mean?” Oh, that might be interesting. Ralph had done about three minutes of that, when he’d popped her cherry. She remembered it being very enjoyable. She’d go for that, she thought.
“Of course, darlin’,” she said, and lay back. She spread her legs, and fluffed her pussy hair up a bit. She giggled, and he laughed. He kneeled on the floor, and bent his head to her crotch.
Ten minutes later, she had the orgasm he owed her. He kept on going, and she had another. Her calves cramped, and her whole body shook. She was panting for breath. That was the best ever, she thought. My finger never did it for me that good. Damn. He was good.
She hoped she tasted good for him. She must, he was licking all over her. She had even clasped her knees to her chest, and pulled her butt up so he could lick her asshole. Now that, she thought, that felt sexy. A guy likes me so much he’ll lick my asshole. That is fucking sexy. My asshole. Got that? My asshole.
He finally stood. He seemed to be taking charge a bit more, she noticed. His cock stuck straight out, hard as wood. He crawled onto the bed, straddling her body. He lowered himself, and she felt his cock nestle right into her pussy lips. Okay, she thought, here we go. I hope he can hold it a little while.
Maybe because he’d already cum twice, he just seemed to go forever. Weirdly, as good as it felt, she got a bit bored again, and watched TV for a while. Goddam zombies, she laughed. I’m being fucked, and watching zombies. Fucking stupid-ass goddam zombies.
She looked at the clock. It was four thirty. They still had over an hour. I’ll be on overtime, if he goes that long, she thought. She knew that he was still pretty turned on, though. She knew she was doing it for him.
She yawned, and watched the fucking zombies. He pounded away, his cock in her cunt, her right breast in his left hand, her left breast in his mouth. She felt pretty good, but she wished he’d hurry up and cum.
Just because it was good business practice, she counted her cash when he finally left. He was honest, at least ... she was two hundred dollars richer. She made a mental note to talk to Larry Monday, and remind him to keep his mouth shut. She didn’t want every lonely heart at Altamont accosting her at her locker.
Monday, it started almost immediately. When she stopped by her locker at lunch, a boy named Darrel Slade approached, and stopped to talk to her. You gotta be fucking kidding, she thought to herself. Those bastards. This is going way too quickly.
“You make some time for me?” Darrel asked, without any small talk.
“Darrel...” she said. “What have you been told about me?”
He squirmed. He’d seemed bold, at first, but now he squirmed.
“Oh ... nothing...” he said. “Just that you were ... friendly ... a nice girl...”
Well, shit. “Yes, I am a nice girl. But probably not in the manner in which you were told about. What exactly were you told, and by whom?” she said.
“Just ... a friend...”
“Darrel. You tell me who, or it ends, here and now.” she was a bit pissed that he was so reticent, after coming on so strong at first.
He was silent. The stupid “guy’s code of honor,” she thought. She decided to change her tactics.
“Darrel...” she said, facing him, moving in a bit closer. “I might be able to ... squeeze you in ... if you tell me who told you these things about me.”
She could tell he was torn, at that. She knew it was going to be Larry, and sure enough, it was.
“Larry Wilmont,” he finally said. “He said ... that you liked to play around. That’s all he said, honest...”
Hmmph. That wasn’t as bad as some things he could have said, if that was true. Well, we will still have to have a little talk with Larry.
“Did you mean it? About squeezing me in?” he asked. She could almost feel the desperation seeping from him. Shit, she thought. What is it with these guys. They are afraid to ask any girl out, but they’ll ask me this stuff? They’ll risk my wrath and major embarrassment, and ask me?
“You got a place we can go?” she said, brusquely. She was a little disgusted with herself, that she was going to do it a third time. I’m a regular working girl, she thought.
“Yes ... nobody will be home at my house until sevenish...” he said.
“You got two hundred bucks?” she said, wondering if Larry had told him about that part of it. From the look on his face, he probably hadn’t. But, he covered well.
“Yes ... I think ... I can stop by an ATM on the way...” he said.
“Well, come on then. Let’s do it.”
He lived in a nice place. Not a mansion, but nice. They went upstairs to his bedroom, and she made sure he locked the door.
“Darrel,” she said, as she drew her jeans down her legs. “You gotta understand, you tell anybody about this, and there will be no repeat performance. Larry is out, now, because he told you. You are his replacement, but you can’t tell. Got it?”
He nodded. She hoped he understood.
“Got the money?” she asked, and he counted out two hundred dollars in twenties. She stuffed it in her pocket.
“Come on, undress!” she finally said, since he was just standing there staring at her. He woke up, and started undressing.
She got naked quickly, and sat on his bed. She looked at him. He had the nicest cock, so far, even slightly bigger than Ralph’s. And it was hard, damn it was hard. She felt a burst of pleasure, knowing that she did that for him. I am that goddam good looking, she told herself. Then again ... teenage boys ... it’d probably be that hard if I was fat and forty.
He was unsure what to do. He clasped his hands over his cock, causing her to giggle.
“Come on, get up here,” she said, and he crawled up on the bed.
She had some ideas.
“Darrel. Before we fuck, you must eat my pussy until I cum a few times. Understand?”
He nodded fervently. And what guy would want a taste of me, she thought. She leaned back on the bed, spreading her legs wide. He nestled inbetween her legs, and she felt his hesitant touch on her clit. Ahhh ... she thought. Let the fun begin.
For a novice, he was good, she finally decided. He’d even licked her asshole, when she’d curled her body up to give him access to it. And he seemed to love her clit. She came, and came again.
“Darlin’,” she finally said. “Anytime you’re ready, stick it in me.”
He licked her a little longer, and finally crawled up on the bed beside her. There was a little confusion, and he finally got himself situated on top of her. She reached down and took his cock in her hand, and guided it to her cunt. Ahhh ... that feels good, she thought, as he pressed in and out, in and out, wetting himself with her juices. He finally began pumping her, in long slow strokes. She felt another orgasm, that quickly. Damn. This was gonna be fun, she thought.
Darrel fucked her like a pro. She reminded herself to ask him later if this really was his first time. He seemed to know exactly what he was doing. She came, hard, a big one, considering she’d cum twice before when he licked her. She came so hard she felt a few drops of pee shoot out of her urethra, to her embarrassment. She didn’t figure he’d notice, at least.
He finally pulled off her, and lay on the bed, exhausted. She finally pulled herself up, and got dressed. He almost seemed asleep. On impulse, she kneeled before him, and took his soft cock in her mouth. It turned her on to taste herself on him, and she sucked him in and out, until she felt him start to get hard. He was sitting up by now, supporting himself with his arms. She wasn’t sure why she’d started, but now there wasn’t really anything to do but go to the end, she thought.
After probably ten minutes of fairly intense sucking, he squirted a little bit into her mouth, sighing deeply. She was supporting herself with her hands on his thighs, and she could feel his whole body tense and relax. You got your money’s worth, dude, she thought. More than, even.
He took her home, and she waved goodbye as he drove off. The weekend loomed before her. Now what, she thought.
Cheshire and her mother went out that night, with her uncle. Her uncle Wilbur. Cheshire and her uncle had a peculiar relationship. He’d always liked her, and thought she was something special. She accepted that he perved over her, now that she was grown up. It wasn’t hard to tell. He told jokes to her, sometimes even fairly nasty ones, when her mother wasn’t around. He said things like “Go put on your jammies and come sit on my lap,” once again when her mom wasn’t in the room. She didn’t feel that bad towards him, she knew he was just a harmless old man. And, she knew he’d helped her mom out financially, at times.
Anyway, they had a good dinner, at an expensive restaurant. Cheshire was wearing a pantsuit, and the top was cut reasonably low. She knew she looked fine, and she could see uncle Wilbur staring at the top of her breasts, time and time again. She even saw him lick his lips, once. An idea began percolating in her mind. A naughty but financially lucrative idea. She knew he was pretty well off. She knew two hundred bucks wouldn’t mean shit to him. But would four hundred? Six hundred? Hmmm.
After they went back to her and her mom’s house he followed them in. They played some card games, and at some point that evening her mother excused herself to go to the bathroom. Cheshire used the opportunity to heat things up a bit. She sat in Uncle Wilbur’s lap for a moment, and swished her rear end around on his crotch. He just froze, and she knew she was freaking him out slightly, although she was giving him what he probably wanted.
“What’d you do that for...” he finally said.
“Just because...” she answered, giving him what she imagined was a seductive look. There, she thought. Let him get all fired up.
As the evening progressed, he stared at her, again and again. She knew she was all he could think of. She asked herself again just exactly what she was expecting to make happen. She looked at him objectively. She didn’t really want to fuck him, like she had the other boys. She figured he’d pay handsomely just for the privilege of pawing around on her body a bit. And maybe ... she thought ... maybe I might ... stick it in my mouth, if that. Maybe.
Her mom moved to the kitchen, and began doing stuff in there. Cheshire leaned in towards Uncle Wilbur and whispered to him.
“Let’s go get some ice cream,” to which he readily agreed. They told her mom, and got in his car, where they could talk freely.
“Cheshire, Cheshire, my little darling,” he said immediately. “You don’t know that you do to me, girl...”
“Yes, I do,” she said. He laughed. She continued. “It’s not hard to tell, Uncle W. I could feel it, when I sat in your lap.”
He blanched at that. He wasn’t ready to go that far, that fast. She laughed to herself. She knew she was blowing his mind.
“Uncle W. I got a car fund started. I’ll need a car, in another year, when I hit sixteen. If you would consider donating a significant amount, like say, four hundred bucks, I will do something for you in return. Like, say, more of that lap dance thing?”
“Oh, shit...” he said. “Oh, holy shit ... Cheshire ... are you sure ... are you sure about this?”
“Hell yeah,” she said. “Uncle W ... you are not the first ... I’ve already got four hundred dollars in my jar...”
“Jeezus, child...” he seemed speechless. She knew he was thinking, though.
“What exactly will I get for my four hundred dollars?” he finally said.
“Uncle W, I will give you two hours of lap dances like I did while ago, but much longer, of course. And I’ll let you play with my tits some. Does that sound fair?”
“Oh, shit. Yes, yes,” she knew she was making his dreams come true. Silly old perv, she thought. Of course I am.
“When?” he asked.
“Now. Call Mom and tell her we’re going to see a movie, and we’ll go to your place.”