Confidence Man - Cover

Confidence Man

Copyright© 2002 by Blackdog

Chapter 1

Erotica Sex Story: Chapter 1 - 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  

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."

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