DOCTOR DAN'S EROTIC STORIES
CONFIDENCE MAN
AUTHOR | Blackdog |
DATE ADDED | 15th November 2002 |
AUTHOR EMAIL | |
STORY CODES | F/m, pedo, school |
This story
may not be reproduced in any form for profit without
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I was in the principal's office again, and getting yelled at. Here it was just the second month of my freshman year, and 14-year-old ass was getting pounded.
But in a very nice way. Our high school's pretty, 37-year-old principal, Ellen McCarthy, was nude on her huge desk, her lithe legs wrapped around my naked behind, her pretty ankles beating a rapid tattoo on my thrusting ninth-grade buns.
Her arms were tightly encircling my neck and shoulders, and her hot, middle-aged cunt was greedily swallowing the stabbing motions of my swollen teenage prick. My face was cloaked by the fragrant short-blond hair of her Meg Ryan-ish do.
"Fuck me harder!" she shouted into my right ear. "Fuck your hard boy-cock into your principal's hot pussy! Fuck me harder, you stiff-cocked wonderful bastard! Make me cum so hard, you terrible nasty wonderful young stud!"
I have to say that under these conditions I didn't really mind being called to the principal's office, even if it was the third time this week. And this was way after school, at 7 o'clock on a Thursday night! I guess poor Miss McCarthy just couldn't get enough of what I had.
And what, may you ask, would a skinny 14-year-old have to offer a lovely school administrator 23 years her junior? Why would she drop her panties, spread her legs and point her pretty toes to the ceiling for some geeky ninth-grader who was recently too afraid to even speak to girls, let alone bone the principal on her own desk?
Well, as the saying goes, thereby hangs a tale...
I never much liked my Uncle Mike; few members of our family. did. He was loud, he was pushy, and he drank too much. He stayed up all hours, ate all kinds of spicy and outrageous stuff, and never bothered to spare your feelings if there was some weak spot in your armor.
He was married and divorced four times; he lost many a job but always found a new one quickly, and often a better one. Nothing seemed to faze him -- no struggle or setback appeared to make an impact. If his wife left him or his boss fired him, he would merely reach for another cigarette or beer and go on with whatever story he was telling.
For all these reasons, Uncle Mike was both the subject of considerable criticism and disguised envy. He was not have been what you'd call a role model in the classic sense, but he was definitely -- in his own way -- "cool."
I never much speculated on what made my father's half-brother so blasé about life's ups and downs until the summer he came to live with us while his latest messy divorce was being resolved.
Mike was not what you'd call a handsome man; but like folks like Humphrey Bogart and Clark Gable, he had a certain charisma, a presence that evoked a response in people, especially women. His other qualities eventually drove females off, but some elusive charm drew them in initially.
Wiry, dark-haired with an archaic pencil-thin mustache, Mike almost always had a cigarette or beer glass at his lips, but this one August day in the driveway on the side of the house he set them aside and started to talk to me.
"Jack," he said, as I was carrying a bag of trash from the kitchen to the cans on the side of the house. "How old are you now?"
"Fourteen," I said, a little surprised that he was even addressing me. Since I had no money to lend him or smokes or drinks to provide, why would be waste his time on me?
"Fourteen," he said, tapping a fingernail on his teeth as if he was trying to remember something. "Gonna be in high school in the fall."
"That's right. Brooksville High," I said.
"That's a big step, going into high school. A lot of big memories, a lot of important stuff happens in high school. Seems a shame to see you in such a sorry-ass condition to begin with," he said, not unkindly.
I turned red with anger and embarrassment. "Whe- well, what do you mean by that?" I finally replied, my face hot and my steam rising.
"Well, look at you," he said as he slouched on a chair outside the kitchen porch. "You walk around like you expect to be punched in the face any minute. I don't see any skirts comin' around sniffing after you, and if you've got any friends, I haven't seen 'em."
They say that the true sting in reproach is the element of truth in it. What was accurate was that I was not the boldest lad to be entering high school, and that my timidity was as obvious as if I had worn a bright red T-shirt with the word "Wimp" stenciled on it.
"Now, don't get all upset," he said. "I don't piss on a man unless I got a reason to. What it is is that I was just like you my summer of being 14, and something happened that changed my life. I figger that maybe it's only fair that I should pass it on to you, since I never had a son." A pause. "That I know of."
Fucking the principal on her desk was only a burden in the sense that it sometimes took a little off my fastball -- if you receive my meaning -- when I sodomized the head cheerleader.
Pretty, perky Jenny Kennedy, with the long honey-blonde hair that reached to the middle of her back drove to school every morning along the same route I took when I hoofed it. The first month of school saw her bright-blue Mustang convertible roar indifferently past me; now her car slid up silently alongside me and she hissed" "Get in!"
I would quickly dart into her front seat and instead of her driving to the school three blocks away, she would wheel the brand-new steel chariot to a nearby shopping center, pull in behind the stores in an area secluded by trees, bushes and storage bins and throw herself into my arms.
"Mmmmmm," she'd say after she broke a long, tongue-twisting kiss. "I did like you said and didn't wear any panties today. Are you ready to fuck my asshole again like you did yesterday?"
In a moment she was on her hands and knees, her sweet plaid cheerleader skirt flipped up and me mounted on her soft-rounded ass, my rigid phallus drilling urgently in and out of her happy shitter.
"God, feels so fuckin' good!" she grunted. "So fuckin' good to be fucked deep in my asshole! God, I never knew! Just keep slammin' that hard cock of yours up my sexy cheerleader ass! Fuck my asshole and shoot out all your hot cum deep in my ass! Make me leak your hot sperm all day long at school! Buttfuck me hard!"
I did my best, which meant that my thrusts soon brought the 17-year-old prom and homecoming queen to a shuddering anal orgasm, but also resulted in me hosing a thick, hot stream of sperm deep in her schoolgirl guts. Eventually I would pull out, panting. and she would moan in delight.
"God, that was good! Who would think the head cheerleader at Brooksville High would be a butt-slut for a freshman boy?" she said, her perfect tush still upraised and leaking semen.
"I love being your butt-slut, Jack," she said, turning her face to me, an imploring look coming over her pretty 12th-grade features. "Do you think you could fuck my ass one more time this morning? Please?"
As I say, what did I have that put me in this admittedly unlikely but enviable situation.
In a word: confidence. A self-confidence both very ordinary and very special, and provided by the guidance of my roguish Uncle Mike.
"C'mere, kid," he said motioning me over. "Let me tell you what you need to know. And listen carefully; I'm not gonna cast pearls before slime."
"Swine," I corrected him.
"Whatever," he said. "Life's not complicated, but there's a few things you gotta remember. First thing is this: everybody's as scared as you are. no matter how they look. Deep inside everybody's puttin' on a front. People admire and follow folks who look like they've got the world by the tail, if only 'cause people figure a little of that self-confidence might rub off on them.
"Second is this: Everybody puts up a front. Everybody's got secrets: secret ideas, secret weaknesses, secret lusts, secret shit. And usually, the thing they're most secret about is the thing that they complain the most about. Want to spot the closet drunks? Find out who preaches the most against demon rum. Want to find out who's the hottest bitch, the kind of girl who'd do it with a donkey in the mud for $5 and a bus pass? Look around for the most frigid bitch there is.
"Third thing is this: If you look like you know what you're doing; you can get away with almost anything. A smooth operator could talk himself into Queen Elizabeth's outhouse, or Fort Knox. Talking your way into a girl's buttery little panties is child's play, compared to that.
"Fourth and lastly -- for now -- is this: confidence -- complete, unwavering confidence in yourself -- is a better superpower than X-ray vision or shooting fireballs out of your hands. For one thing, it's more likely to get you laid."
I listened to all of it, nodding here and there. "Well, Uncle Mike, it sounds good, but just saying 'I'm confident' doesn't seem to be enough. How do you go from being, well, self-conscious and doubtful to being so sure of yourself?"
He gave me a sly smile, and reached under his chair. "Oh, you'll need a little hand," he said, raising a baseball bat he'd secreted there. "Believe me, this is going to hurt you a lot more than it's going to hurt me."
For an instant I wondered what the heck-- and -- then -- I...