High School Hookers - Cover

High School Hookers

Copyright© 2012 by Jacqueline Jillinghoff

Chapter 7: Kitten and The Make-A-Wish Foundation

Erotica Sex Story: Chapter 7: Kitten and The Make-A-Wish Foundation - A group of high school freshmen graduate from babysitting to a sexier, more lucrative way of earning pocket money. They rock their school and their neighborhood, taking control of their lives in the process.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Ma/ft   ft/ft   Fa/ft   Mult   Teenagers   Consensual   Incest   Father   Daughter   First   Oral Sex   Masturbation   Babysitter   School   Prostitution  

Believe it or not, Holly still hadn't fucked. After that scene with her dad, she'd moved into his room, and she was sleeping in his bed every night, but he didn't have the balls to go all the way with her. Holly couldn't explain it. Maybe he thought that if he didn't take her cherry, he wasn't doing anything really wrong, that if he only came in her mouth, he was really a good guy. She went out on some jobs after school started, but all she did was blow the guys — which she was great at, by the way, with all the practice she got with her father.

We called her The Virgin Whore.

That changed in middle of October, when we got a call from a guy who said he needed somebody petite.

"That's Kitten," I said. "She's the petitest girl we have."

"How much does she weigh?"

"How much does she weigh? I don't know — Kitten, how much do you weigh?"

"About ninety-five," Holly said.

"About ninety-five," I repeated into the phone. I heard some mumbling.

"Hello?"

"Yes," the guy said. "No one smaller?"

"For that, you'd have to get a twelve-year-old," I said.

"All right, then."

I gave him the price and told him where to pick her up. When I hung up, Robyn said, "What was that all about?"

"Another perv who's into little girls," Teri said. "Don't forget your Teddy bear."

"It was weird," I said. "I think there was somebody else there with him."

"More clients, more money," Robyn said. "Think tonight's going to be the night?"

"I hope so," Holly said. "I'm sick of you guys bragging."

"Well, then, don't suck them off right away," Robyn said. "Make them want more."

When the time came to leave, Holly brushed her hair in my dresser mirror and put on her new fur-collar jacket. She looked hot. Not that she was ever slutty. All she had on was a pair of jeans and a blue turtleneck, but the jeans hugged her butt, and, now that she was allowed to wear a bra, she filled out her top sweetly. Her tits were modest, but totally munchable. She looked like what she was — a cute fourteen-year-old piece of ass.

The three of us walked her to my front door. We hugged her and kissed her goodbye, and we wished her good luck, which was a mistake. These days my brother Carter seemed to be hovering around us all the time. He was in his room with the door open when we trooped past, and he followed us out through the living room, spying on us like he was on a mission from Mom. I knew what he was thinking. He was wondering why Holly needed good luck for a babysitting job. I decided we had to get cellphones to take our calls. I didn't want him eavesdropping on the extension in his room. I was scared he already was.

It was still light out when the guy picked Kitten up in front of the tot lot. He introduced himself as Mr. Schumann, which was strange. Most guys want you to use their first names. He drove an old white pickup with heavy pipes in the back, nothing like the new-smelling Mercedes and BMWs we usually got. The front hood didn't even go down all the way. It was fun riding up high, though, and the guy was better looking than most — trim, with long legs and a square jaw, like a cowboy. He was dressed like a cowboy, too, in a plaid flannel shirt, jeans, and tan work boots. He had a quiet voice, and he seemed interested in her. He wanted to know how such a pretty young girl got into this line of work, as he called it.

"My friends are doing it," she said. "And I'm sleeping with my dad, so I thought I might as well."

"Sleeping with your dad? Isn't that a little messed up?"

"It chills him out," she said.

"Well, whatever, we're grateful you were available tonight."

The "we" made her wonder, but grateful — that was sweet. Holly liked this guy, and what she was grateful for was that he would be the first guy to fuck her.

As things turned out, though, he wasn't.

He lived like forty minutes away, she said, in a white Cape Cod that looked dingy in the twilight. The lawn was scruffy, and the driveway wasn't paved. It was gravel that crunched when they pulled in. The front steps were covered over with a wooden ramp, and just as Holly and her cowboy got to the top, a woman opened the door.

"Sharon, this is Kitten," the guy said. "Kitten, this is my wife, Sharon."

Holly went inside. The cowboy came in behind her closed the door while the woman looked her up and down.

"She's awfully young," the woman said. "Just how old is she?"

"Better we don't know," the husband said.

"Do you get paid first?" the woman asked.

"Yeah," Holly said.

The woman pressed a thick wad of bills into her hand. Holly counted it out. But instead of putting it in her pocket, she stood there with it, looking from one to the other, and wondering just what they wanted with her.

"Is that not enough?" the woman asked.

"Not for two people."

"That long drive and you didn't explain it to her?" the woman asked her husband.

"I thought we both could," he said.

"That's my man!" she said. "Look, Miss..."

"Kitten," Holly said.

"Kitten. You're not here for us. You're here for our son. He's in the other room."

"OK," Holly said, but she wasn't feeling at all comfortable.

"He's very sick," Mr. Schumann explained. "We asked him if he wanted anything, and he said, flat out, he wanted to know what it's like to be with a girl."

"Is he going to die?" Holly asked.

"Yes," Sharon said.

"Don't worry, he's not contagious," her husband said. "But his bones are weak. If you're not careful, he could break something. That's why we insisted on somebody small."

"Well, I'm small," Kitten said.

"If you don't want to, we'll understand," Mrs. Schumann said. "But you'd be doing us a favor. You don't have to do much. Just touch him. Let him touch you. Whatever he feels up to."

"Is this something you'd want to do?" Sean asked.

"Sure," Holly said.

She couldn't say no, could she? For a second she even thought she should do it pro bono, as her dad the solicitor would say. But they guessed what was on her mind, and they insisted she keep the money. Their friends had raised it them — not for this, specifically, but for anything they needed — and they wanted her to have it. They said it was worth it to put a smile on their son's face. She stuffed the bills in her jacket pocket.

They took her back to a door behind the living room. Mrs. Schumann leaned against it, knocking and turning the knob at the same time.

"Sean, honey," she said, "your date's here."

The boy was already naked, with a yellow afghan pulled up to his chest, and a sheet underneath folded back into a white border. His thighs were open, and the covers sagged between them, hugging the lump of his scrotum and the nice curling snake of his wiener. On his right side, the afghan rose to a peak where it covered his foot. On the left, it was flat. It dropped off below his knee like a cliff.

"Sean, this is Kitten," Mrs. Schumann said, like she was talking to a little kid. "Isn't she nice?"

"She's cute," Sean said.

He had the same square jaw as his dad, the same sky-blue eyes. He would have been really cute, except his cheeks were sunken and veined, and his eyes bulged under his big bald head. For a second, Kitten thought she was about to do it with an alien. Even the bed looked like a space pod, with its shiny silver rails and the control box next to the boy's hand. He'd raised the mattress, so he was half sitting up.

"We'll leave you two alone," Mrs. Schumann said. "How long do you think you'll be?"

"You paid for an hour," Kitten said.

"Oh, I don't think I'll last an hour," the boy said.

"Have fun," the mother said.

She left with the dad, but they didn't close the door all the way. Maybe in case something went wrong.

"I hope this isn't too weird for you," the boy said. His voice was surprisingly strong.

"I think it's great your parents are letting you do it."

"They said I could have anything I wanted. What else is there?"

"You OK for it?"

"I think so," he said. "I'm having a pretty good day."

"Let's see if we can make it better."

She put a condom on the nightstand and turned the reading lamp toward the wall. The boy's eyes glittered in the softened light while he watched her strip. First, she dropped her jacket on the floor. Then came the turtleneck, which mussed her hair a little and tugged at her cat's-eye glasses, and then her loafers, and her jeans and socks. She turned around for him, modeling her underwear.

"That's a pretty bra," the boy said. It was a half-bra, really, jellybean pink, with lace scallops over the cups. Her panties matched. Jasmine had picked them out for her, naturally.

"It unhooks in the front," she said.

"Can I?"

"Sure."

She leaned over him, holding the rail, while he fumbled with the snap. It took him a minute to figure it out, but he looked proud when he finally got it open and pushed the straps back over her shoulders. She shrugged it off, and his hands went right to her tits. He felt them gently around the sides, and lifted them underneath, weighing them (guys love to do that) and brushed the nipples, which got pinker stiffer under his touch. Kitten told him not to be afraid, that she liked it when guys pulled on them.

"I have a girlfriend with really big boobs," she said. "Next time I'll bring her over, and she'll let you suck on them."

"Can I suck on yours?"

"Yeah, do what you want."

It was awkward, though, with her standing, and sitting up was hard for him. So Kitten climbed into the bed. She rode his stomach like a cowgirl, just where the mattress bent, careful not to put her full weight on him, and, supporting herself on the top edge of the bed, she lowered her tits toward his face.

He crushed them between his hands, and right away tried to see how much of them he could fit into his mouth. Kitty's tits are the perfect size for that game. He got them most of them in, one after the other, chewing and sucking. His hands went around her back and down her panties, squeezing her ass. Kitten could feel how horny and desperate he was. It was like he was trying to burn the experience his brain, so when his time came, the last thing he'd be aware of was the feeling of her soft titties in his mouth.

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