High School Hookers
Chapter 5: Holly Joins the Team

Copyright© 2012 by Jacqueline Jillinghoff

Erotica Sex Story: Chapter 5: Holly Joins the Team - 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  

We stayed another hour or so while Aidan recovered. We had some more wine, and he told us about safe sex and shit like that. Our sex-for-money scheme really turned him on. He said if we were serious about it, he'd sneak us into his office for gyno exams and set us up with condoms and birth control — for a nominal fee, of course. He also said he'd introduce us to some rich friends of his who he knew wanted to have sex with underage girls. Also for a nominal fee. That's when Robyn called him a pimp. He called her a Jew slut. I could tell they liked each other. His dick perked up again, and she let him bang her before we left.

For a nominal fee.

Robyn and I were on board with becoming prostitutes. Just the word excited us, like we belonged to a secret club nobody else our age had a clue about. We weren't sure about Teri, but Robyn figured she'd be up for anything, especially if the money was good enough. She had a clothes habit to support. It was Holly we were worried about. She was so naïve, and her dad was so controlling. I mean, he taped up her tits, for Christ's sake. He'd probably never let her out of the house, and even if he did, she'd probably let something slip out and ruin the whole thing.

Fortunately for us, and for the plan, it was her dad who turned her into a whore. I don't think he meant to, but his attitude kind of convinced her it was the thing to do.

It happened like this:

While Robyn and I were picking up some cash at Aidan's, Teri and Holly biked over to Target, where Teri helped Holly pick out a couple of bras on sale — 28B, a real adult size, Holly said proudly. She paid for them out of her babysitting money. Teri boosted some black lace panties for herself. Just to show Holly how it's done, she said.

Holly decided to wear one of her new bras when her dad got home. Teri offered to wait with her in case anything happened, but Holly said no, she had to do it herself. If her dad didn't say anything when Teri was there, the crap would definitely hit the fan when she left. Better to get it over with, Holly said.

Teri called up and told me what was going to happen. Robyn stayed over at my house for dinner, and she and I kept watch out the living room window. My brother Carter kept bugging us, wanting to know what we were looking for. He's sixteen, and he's hot for my girlfriends. He'd stared at Robyn's tits all through dinner, even though she'd put her bra back on. I swear he was rubbing himself under the table. Just like Aidan rubbing himself through his robe. Men are men, I suppose, no matter how old they are. We told him to fuck off.

It was almost eight o'clock when we saw Mr. Harbison's car pull into the driveway across the street. Holly's dad is a good-looking guy, and a lawyer, and he's always well-dressed. He had on this tan summer suit with a lime-green shirt and a dark green tie, which was still knotted neatly at end of a long, hot day, and a matching handkerchief in the pocket. His hair is light brown, with gray at the tips, and he wears tortoise shell glasses with round lenses. For a total asshole, he's pretty scrumptious. Robyn and I watched him open the front door. He took a step inside and froze.

Holly was standing in the living room, waiting to greet him. We couldn't see her from where we were. She told us about it later.

"What's all this?" he demanded.

I would have loved to have seen the look on his face. Oh, I forgot to mention — the reason he noticed her bra right away was that Holly had stripped down. Besides her new underwear, all she had on was her droopy denim shorts.

Like she said — get it over with.

"All the girls wear them," she said.

"If all the girls used drugs, would you do that?"

"It's a bra, Daddy."

He looked her over from head to toe — her bare midriff, her short bare legs and her bare feet, her little tits in their soft cotton cups. I hate to admit it, but at that moment, I would have felt sorry for Mr. Harbison. Holly has a nice, compact body. It had to drive him crazy to see her like that. I mean, his own daughter, practically topless. She's the bravest girl I've ever known, but she can be a real dope. She should have expected what happened next. All she wanted to do was prove to her father she was growing up. Sex was the farthest thing from her mind.

Maybe she should have kept her tits taped up.

We saw Mr. Harbison put his briefcase down. We saw the door close behind him. He walked up to Holly and put his hands on her naked shoulders.

"If you want to grow up so badly," he said, "you should grow up all the way."

Her nipples were poking up under her bra. Her dad ran the ball of his thumb over both of them.

"It's a very nice bra," he said. "Very flattering. It gives your breasts such a nice ... definition."

"You mean I can wear it?"

"Yes. But not just now."

It was Holly's turn to freeze. Her dad reached around her and unhooked her bra strap. He was so quick she barely felt it. A chill went through her as he slid the straps down her arms and kissed her collarbone. Her bra landed on his expensive brown shoes. He squeezed her right tit with his left hand, puffing out the nipple. His right hand went down her back and into her shorts.

She felt a hardness against her tummy, and even she knew what that meant. His lips went up her neck. They brushed her cheek. He whispered in her ear.

"You remind me so much of your mother."

He let go of her tit and tilted her chin up, looking hard into her eyes.

"Kiss me, Kitten. Like you did when you were little. You were Daddy's little Kitten, remember?"

That made her feel warm inside. She was never happier than when she was a little girl sitting on Daddy's lap, and she'd do anything he wanted if she could feel that way again. So she kissed him. On the lips. Lightly, then harder. And harder. He crushed her in his arms. He put his tongue into her mouth, and she let him do it. It was love, at least, the most love had shown her since her mother died, and it made her head swim.

So she barely knew what he was doing when he unzipped her shorts and pushed them down. They fell off her feet as he scooped her up in his arms. All she was wearing now was her little-girl panties — a pair he bought her, pink with tiny red hearts and red bow in the front. She was small enough that she could still wear kid sizes, except they were snug, and they hugged her shaved slit.

"Are you hungry?" he asked her.

He makes her wait until he gets home before she can eat, and she was starving. She only nodded, her eyes wide.

"I thought tonight we'd go out to eat," he said. "Later."

 
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