High School Hookers
Chapter 3: Holly Frees Her Tits

Copyright© 2012 by Jacqueline Jillinghoff

Erotica Sex Story: Chapter 3: Holly Frees Her Tits - 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  

"You sucked his what!?"

"That's not the point," I said. "He gave me a hundred dollars."

But Holly didn't care about the money. It grossed her out too much that I put a guy's cock in my mouth. The fact that I liked it grossed her out ever more.

"But you don't know if he gave you the money for the blowjob, or to keep your mouth shut," Teri said. She was sitting on the floor beside the bed.

"It still beats seven bucks for babysitting," I said.

"What you should do," said Robyn, who was sitting at my desk, "is blow him again, only this time ask for the cash up front."

"No," Teri said. "Get him to fuck you, and charge him two hundred."

"You guys are insane!" Holly said.

"OK, everybody here who has ever had an orgasm, raise your hand," I said.

Three of us put our hands in the air. Holly sat at the head of my bed with her legs crossed and her hands in her lap.

"You only had your first one yesterday," she said.

"I had two yesterday," I said. "And two more this morning. And they were fucking awesome."

"Yeah, don't knock it if you haven't tried it," Teri said.

Holly lives across the street from me, and she's been my best friend since we were little. When we were in fifth grade, people thought we were twins. We were both petite, with the same brown eyes and chestnut-colored hair. But then I shot up, and Holly stayed the same size.

She was like a kid in other ways, too. That was mainly because of her dad. Her mother died when she was small, and as she got older, he put all kinds of restrictions on her. He never let her hang out at the mall with us or use the phone after seven o'clock, and he made her wear her hair in pigtails. Mom said he worried about her because she was all he had left, but he had to let her grow up sometime. The kids in middle school were already making fun of her hair and those stupid pink corduroy jumpers he made her wear to school, and it was only going to get worse when we got to ninth grade.

But the weirdest thing was, Holly never grew boobs. That couldn't have been her dad's fault. Those things have a mind of their own, believe me. Mine might have been small — they weren't half as big as Teri's or a tenth as big as Robyn's — but at least you could see them. Holly was still as flat as a nine-year-old. She always wore loose, floppy T-shirts to hide it, never tank tops or halters, or even T-shirts that actually fit. Her dad wouldn't let her, anyway. He said real clothes would let her points show. That's the word he used — "points." The way she dressed, I don't think I ever saw her nips poke out once.

She had one of those loose shirts on now, and baggy denim shorts. The four of us were back in my room, waiting for the phone to ring. But it didn't. Most of our customers were away on vacation. This was our last babysitters' meeting for the summer, and probably our last ever. Once school started, we'd have better things to do than look after other people's kids. My brother the geek was off at the library for a slide show about black holes and shit, which was a break, because otherwise he'd be hanging around us, showing off for Teri.

"I've been having orgasms since I was twelve," Robyn said.

"What about you?" I asked Teri.

"I don't remember," she said.

Teri was always cagey when she talked about anything personal, but we were pretty sure she'd already had sex. She was the first one of us to notice boys, back in like sixth grade when I thought they were all assholes (still do), and last summer, when her older cousin came to visit, they were home alone all day in her house when her parents were out working, and we didn't see her for like three weeks.

"Haven't you ever experimented?" I asked Holly.

But she hadn't. She never touched herself, or let a boy feel her up — as if her dad would ever let a boy near her. She never even played games, like straddling the edge of her bathtub and rocking her hips back and forth. That's how Robyn said she got started.

"Can we talk about something else?" Holly pleaded.

"No," I said. "I wanna talk about sex. There's nothing to be embarrassed about."

"Why don't you show her?" Teri said.

"Yeah, since you're suddenly the big expert," Holly said.

She thought that would shut me up, but after fooling around with Aidan and my playtime alone in bed that morning, I was horny as fuck. Mom says I'm impulsive, and I acted on impulse now.

I got off the bed and pushed my gym shorts down around my bare feet.

"Whoa girl!" Robyn exclaimed, clapping her hands.

"Wow, hot panties," Teri said. "Where'd you get those?"

She was being sarcastic. They were plain white. I'm not a clotheshorse like her. Even today, just for a club meeting, she had on a blue satin top and canary-yellow cargo pants, and I would have bet her bra and panties matched.

"I got them at the mall," I said. "You know — that place where Holly never goes."

"Cut it out," Holly said.

"Take them off," Robyn said.

So I did. And I threw them at Robyn's head.

"That's what I'm talking about!" Teri said.

"You do have a nice ass," Robyn said. "But you're still not much in the boob department."

"We have you for that," I said.

We were getting silly, except for Holly. She wasn't looking at me. She was looking down, and she was sucking on her two middle fingers, which is what she always did when she got nervous. Her face was as red as a beet. We'd been friends forever, but neither one of us had ever seen the other naked. All I had on was my red T-shirt. I wasn't wearing a bra. My nips were poking up, and the shirt hung just over my patch. The back kind of rested on top of my ass.

"Look at me," I told her.

"Yeah," Teri said. "You need to loosen up, girl."

"Help me out here, guys," I said.

Robyn, who was sitting at my desk, whipped off her T-shirt and bra.

"Wow," I said. "I mean — wow!"

I couldn't help it. Yeah, I'd seen them at the pool, but shit, they're impressive. They're like globes — white planets with pink polar caps. She's a D-cup at least, and still growing.

Teri sighed, like it was a hassle to be bothered, but she joined in. She stood up and stripped naked. I was right about her underwear: the bra and panties were both mint-green cotton. Her tits aren't as big as Robyn's, but they're nicely shaped, round and kind of solid-looking underneath, but with short, curved slopes up top and little brown nips that tilt up. But what was really stunning about her was her skin. It was the same even, tawny color all over, and smooth as polished maple.

So Robyn was topless, and I was bottomless, and Teri was nude. We stood around the bed, one to a side.

"Look at us, girl," Teri said.

Holly finally glanced up. She got an eyeful of Robyn's tits, and a tiny smirk crossed her lips.

"Like 'em?" Robyn said.

"Wow, you have tits," Holly said, trying not to sound as awed by Robyn's mammaries as I was. "Proud of yourself?"

"I've got a lot to be proud of."

"Ya know," Teri said. "One of us here doesn't fit with the others."

"You gonna do something about that?" Robyn said.

"No," Holly said.

"Come on," I said. "Let's see what ya got."

"I don't have anything," Holly said.

"You gotta have something," Robyn said.

"Well, I don't. Please."

"Strip her!" I yelled, and the three of us dove on top of her.

She fought us like a wildcat. I couldn't believe how fierce she was, smacking at us and clawing at the sheets, and all the time begging us to leave her alone. She sounded really scared. Somehow we got her flipped over on her stomach, with her head pointing toward the foot of the bed. Robyn held her down by the shoulders, and Teri and I pantsed her. Her underwear came off with her shorts. I tried to get her to keep still by pressing my hands on her ass. It was small, of course, but it was cute — a real little-girl bubble butt. I liked the soft feel of it. I was getting more turned on, and I hoped Teri and Robyn wouldn't notice me humping the back of her thigh.

"Get her shirt!" Teri said.

"Stop it!" Holly squealed, and she struggled even harder.

She bucked her ass and swung her heel into my back a couple of times. I twisted out of the way and lost my balance, and I landed ass-first on the floor. My hand went straight to my pussy. I just wanted to close my eyes and have another orgasm, but the bed was shaking and bonking me in the back of the head, and the other girls were making too much noise. So I got up again and watched for a chance to throw myself back into the wrestling match.

 
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