Confidence Man - Cover

Confidence Man

Copyright© 2002 by Blackdog

Chapter 5

Erotica Sex Story: Chapter 5 - A timid high school freshman learns the secret of life and soon has cheerleaders, prom queens, teachers and even the principal dropping their panties for him.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   mt/Fa   Consensual   Mind Control   Heterosexual   Humor   DomSub   FemaleDom   Spanking   Light Bond   Oral Sex   Anal Sex   Slow  

One.

Dennis Gilbert was probably the most "sensitive," reserved soul at Brooksville High. Jenny Kennedy was about the most outgoing and brash. Who would have thought that their stories would be connected?

A sophomore, Dennis was slight and pale, one of those kids for whom the rough-and-tumble of high school was sure to be strewn with mishaps. And I just missed this one.

As I walked along the main drag of our campus I heard a thump, a few words and a burst of vulgar laughter. A few more strides and I came upon the scene: Dennis laying on his back, his books scattered, the knees of his pants scuffed and his face red.

"You OK, man?" I said, offering him a hand up, which he took.

"What happened?" I inquired, once we had recovered the spilled texts and other effects.

"Oh, the usual," said the blond-haired boy, brushing some dirt from his shirt. "Some of the local adolescent hoi polloi think that tripping me is tres amusement."

I didn't say it, but it occurred to me that using terms like "hoi polloi" and "tres amusement" -- French, right? -- were contributing to his problem. He was regarded as the sophomore class wimp. His appearance, his speech, the mystery behind why he never dressed for physical education classes all put a big metaphorical "kick me" sign on his back for those blockheads who wouldn't know a metaphor from a machine gun.

It troubled me that man -- that, is, boy -- could be so indifferent to the sufferings of his fellow man, er, boy, but I have to say that my attention was a little big distracted.

The school day was over and it was Wednesday, which meant it if it were a month later, it would have been time to meet Jenny Kennedy, the head cheerleader and a special friend of the most intimate sort. My pants always got tight just thinking about what lay ahead.

How I hooked up with Jenny, a gorgeous senior, was more than a story; it was more like a case history in psychology, maybe abnormal psychology.

Jenny, vibrant Jenny, was not only head cheerleader, she was president of the pep club, which consisted -- this year -- entirely of girls. I'm not trying to make any kind of social statement here, but the club decided that it needed some help -- preferably male -- in climbing ladders, hauling paint cans and otherwise decorating the campus for the big homecoming football game.

"You, you and you," said my basketball coach, one day at practice, pointing at me and two other poor souls. "You just volunteered to be the work detail to help out the pep club."

As conscription went, it wasn't bad duty. We got to associate -- "hang out" would be too strong a term -- with some of the minor queens and princesses of our high school while we tried our best to impress them with our sweaty masculinity. Not that it worked.

We did hang a spitload of signs and such, and Jenny -- as a reward -- offered to give us three boys a ride home in her cool convertible Mustang. By luck of the draw, the other two boys were shuttled home first.

Not a word passed between Jenny and I for the first long minute; she seemed lost in thought. I broke the silence.

"This is such a great car," I said. "Your parents must be really cool to get it for you."

Jenny sort of curled her pretty lip. "My parents are divorced. I live with my mom. My dad's a big jerk. I made him buy this for me."

"Well, he can't be that big of a jerk if he bought you such a fine automobile," I said, taking a position in which I did not really believe.

"Well, he is. Of course, he had help," she said, cryptically.

That was all the conversation until she dropped me off. "Thanks for the lift," I said. "Anytime you need help, just give me a yell."

Her face softened. "Well, thank you," she said. "Hey, I'm sorry if I've been kind of grumpy. I have a lot on my mind."

"Well, you look prettier grumpy than most girls do when they're smiling," I said, laying it on a little. "Don't forget my offer."

She nodded and put the car in gear, driving oh, about, 15 feet before braking. "What time do you get to school?" she asked, turning to me.

"Uh, I usually leave here about 7," I said. "I like to kind of clear my head in the morning and look over my homework and such when I'm fresh."

"Hmm," she said. Then "Bye" as her Mustang sped away.

"And what's on YOUR mind?" asked my Uncle Mike that evening, as I sat on my basketball in the driveway instead of tossing it at the hoop. "Gonna miracle the ball up with your ass?"

I cleared my throat, which I often did when cooking up some B.S. answer to an authority figure. Before I started my sentence, he waved me off.

"Don't try to snow me," he said, popping open a beer. "I've been bullshitted by doctors, lawyers, judges, hookers, shoe salesmen. I've been lied to by experts, me boy."

"Well," I said, "it's like this. There's this real sensitive, real smart kid at school. But the other kids treat him like a freak because he's got a big vocabulary, and he knows all about Shakespeare and Steinbeck and he doesn't play any sports or anything. He gets roughed up and pushed around a lot, and I was wondering if I should try to do anything about it."

"Oh, so now you're the new sheriff in town. You think you can go around righting all wrongs and avenging all evil," he said. taking a drink and wiping his mouth. "If you try to redress every grievance at your school you'll be at it 24 hours a day and still be backlogged."

"I guess," I admitted. 'I thought maybe there was something I could do for him. Maybe if I caught one of those jerks that bully him I could kick the jerk's ass and he'd lay off."

Uncle Mike drained the bottle and gestured with the empty. "I'm sure you could. But that'd be worse than nothing, because now he's the little faggot who needs to have some freshman do all his fighting for him."

I stood up and shrugged. "Well, then I don't know what to do," I said.

Uncle Mike was silent for a moment -- rare for him -- and then he spoke up. "Your friend, there, Mr. Gilbert. You said he was well-schooled in Shakespeare?"

I nodded.

"Well, Clark, me lad, have you ever considered the benefits of getting YOUR ass kicked?"

Two.

I bopped out of the house just as the clock showed "7:00" and began my walk to school. I was kind of pumped because Uncle Mike and I had worked out what seemed like a great scheme to strike a blow for justice on behalf of the downtrodden, i.e., Dennis Gilbert.

I hadn't gone a block when a sleek blue convertible Mustang pulled up. "Got any experience making cheerleading posters, fella?" came a voice.

It was Jenny, looking a lot happier than she had the night before.

"A little," I said. "I studied under the great Jenny Kennedy," I said, arching my eyebrows suggestively.

"Ha! You wish!" she said. "You wanna lift to school?"

A block passed. She hummed and tapped her hands on the steering wheel.

"You're in a good mood today," I said. "I'm sure it's the company."

She turned and gave me a slow smile. "You are the strangest boy. Most boys at this school think one of three things about me. They either are too scared to talk to me, or they think I'm a slut or they think I'm a frigid bitch," she said.

"Gosh," I said, "I can see why someone might be too shy to approach the head cheerleader, but those last two seem a little harsh."

She shook her head ruefully. "Actually, truth to tell, they're both right on." She looked at me. "What do you think of that?"

A beat. I looked her right in the eye, the way Uncle Mike had taught me. "I think you're the strangest girl. Most girls at this school think one of three things about boys. They're either too scared to speak honestly to them, or they think they're pigs ... or ... or ... oh, shit!" I said laughing, "I forget what the third thing was going to be."

She laughed back. You could feel the ice cracking. "Say, you wanna go for a drive before class starts?" she said. "We've got half-an-hour."

I was silent for a few blocks. It seemed like the smart thing to do. "So, you're a basketball player," she said, finally.

"Well, I'm a kid," I said, smiling. "Sometimes I play basketball, but that's not how I think of myself."

She nodded. "Yes, yes, that's how I feel, too. I'm a girl who happens to do cheerleading a few hours a week. I mean, your identity isn't defined by something you do, even something you did years ago... " she trailed off.

"Jenny," I said, "since we have been friends for, what, two days, I feel I can ask you this: what are so churned up about? And why are you so mad at your dad?"

She shook her head. Then, "Oh, what the hell. I've gotta tell somebody. For some reason ... Well, here goes..."

I listened with sober sympathy to her story. which she interrupted every minute or so with "I can't believe I'm telling you this."

Her father and her had been very close, all her life, maybe too close. It pushed her mother to the outskirts of the family, but what blew it apart was the night -- and the nights that followed -- when her father moved from a hug to a kiss on the forehead to a kiss on the lips.

She was 12, and she worshipped her daddy. His tongue in her mouth tasted good, and she felt herself get slick and itchy down between her legs as he drew the kiss out.

In a few minutes her tiny panties were dangling from one ankle, and she was groaning and mewling with pleasure as her father pushed down his shorts and slowly stroked his gnarly member into her preteen vagina.

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