Blackmailed: Cheerleader's Cherry

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A Principal disciplines a stuck-up hot bitch cheerleader.
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Blackmailed: Cheerleader's Cherry

Summary: An Unprincipled Principal disciplines a stuck-up hot bitch cheerleader.

Note 1: This story is dedicated to Doc, who inspired this ass-centered story.

Note 2: Thanks to Estragon for his copy-editing in 2012, and to Tex Beethoven for some further editing in 2022.

All characters are over 18 years of age.

Blackmailed: Cheerleader's Cherry

As Principal of the largest high school in our district of Southern California, every day is an administrative challenge. Drug busts, celebrities' spoiled kids, relationship dramas, cyber-bullying, gangs, I've seen it all. I've also had ridiculously attractive mothers flirt with me, and even straight out offer me sex not to suspend or expel their child. On occasion I've had very pretty teenage girls offer themselves to me as well... but until recently, I'd always resisted the temptations.

But a divorce, a long dry spell between affairs, and bitterness at the landslide of academic changes being made nationwide (for 'No Child Left Behind', read 'Flood All Teachers with Excessive Bullshit Paperwork to Prove their Worth, and Mandate that the Only Education that Matters is Measured by Standardized Tests, and Thus EVERY Child is Left Behind') all coalesced at once, causing my moral shell to wither... and when I succumbed... I really succumbed!

By the last school bell on the Friday I crumbled, the day had already been a compete shit-show, so I was already on the brink of losing it completely... when even I was caught by surprise. Dallas Allen, our cheerleading captain, had been caught having sex in the janitor's closet with Markus Zenron... and can you believe it was with Markus Zenron? If you don't know him, he was our chess champ; not athletic at all, but our resident geek in every sense of the word. Not in a million years could I have been ready for this... it made no sense! As far as I knew, she was dating Elden Winster, the school's starting quarterback. So I pulled the two fuckers (literally) into my office, and asked the obvious question (ignoring the obvious one I really wanted to ask), "Why would you two decide to fool around in a jani'or's closet"?"

Markus looked like he'd already shit his pants, and Dallas was in tears. But given my fifteen years of doing this job, I knew those weren't real tears, but the standard I'm-really-good-at-crying-on-cue-to-get-out-of-trouble tears.

Markus finally stammered, "I-I-I am so sorry Mr. Stanford, it was a really stupid thing to "o."

Ignoring the crocodile-tears girl, I explaine", "You realize that if this transgression goes on your record, you can kiss Harvard goodb"e."

"Y-y-yes, s"r," a completely devastated Markus stuttered, just like the geek he was"

"I may be able to look past this indiscretion... once...if I can only understand w"y," I offered, curiosity getting the better of me.

Markus looked down at his feet and explained, "Dallas told me to meet her in the janitor's closet after school. I thought it was a practical joke and d'dn't plan to go, but.".."

"But, you had to go in case it wasn't a scam," I finished for the stressed-out boy.

"Yes. And she was already there when I arrived, and she asked if it was true."

"If what was true?" I asked.

Dallas finally spoke up, or actually she barked, "Don't you dare, Markus!"

I glared at the blonde cheerleader, her face a mess from the mixture of tears and runny make-up. "Don't you dare intimidate the guy. You can tell me your version once he's done, young lady."

She stopped talking, but the glares she aimed at Markus would have prevented 99.999% of boys from saying another word. "Actually Dallas, go wait out in the hall."

"But..." she began to protest.

"No buts, go!" I ordered, "and stand on the other side of the hall, so you can't listen in," my voice rising, daring her to make any further objections.

Once she left, I said, "Go ahead, Markus. Then what happened?"

"She asked me if the rumours about the size of my um... well... um..." the shy nerd stalled out.

"Your penis?" I queried.

"Yes, sir," he answered.

"So she wanted to know if certain rumours about the size of your penis were true."

"Yes, sir," the mortified boy replied, clearly embarrassed by this conversation and desperately worried about his academic future. Like so many boys and men, one rash decision about a hot piece of tail, and you could lose everything.

I smiled, "And obviously she then wanted to see the evidence, and showing it to her seemed like a really good idea at the time. How long had you two been in there before you were caught?"

"Less than ten minutes, sir."

An idea already forming in my head, I then asked, "Did she give you oral sex?"

"Yes, sir," the nerd replied, his answer barely a whisper.

"And how long did the two of you have actual intercourse before you were caught?"

"Only a couple of minutes."

Poor fucker. Getting to fuck the hottest cheerleader in the school, and then getting caught only a couple minutes into it. Life is a bitch! "Tell you what, Markus. You're a good kid, and I'd hate for you to lose your free ride to Harvard. Can you keep a secret?"

"Yes sir," he replied, a glimmer of hope shining eagerly in his eyes.

"This never happened. No one knows otherwise but you, Dallas, Mr. Harkus, and myself. So don't tell anyone about it, I'll pretend it never happened, and I'll tell Mr. Harkus that appropriate disciplinary action has been taken, so he shouldn't mention it to anyone either."

"Wow! Thank you, sir," he agreed enthusiastically. "But what about Dallas?"

"I shall deal with Dallas," I replied. "Have a good weekend, Markus."

"Thank you, thank you, sir," he grovelled.

"You are most welcome. On your way out, send Dallas in."

"Yes, sir."

A minute later Dallas walked into my office and closed the door. She proceeded to her chair with a sexy wiggle, one that I'm sure had often assisted in getting her out of trouble in the past. Sitting down, she made sure to show a lot of leg. I chuckled to myself, thinking she'd soon be showing lots more leg... and etcetera... than that.

"Ms. Allen, I believe it's undeniable that you copulated... on school property and right after school hours with that timid young man. Also that he could never find the courage to make any moves on you, so you must have been the instigator. Do you agree?"

"Yes, sir." It was obvious to us both that a plea of 'Not guilty' would just be silly, although she wouldn't be without resources when it came to any sentencing negotiations.

"So what should we do about this situation?"

She first tried the standard approach. "Mr. Stanford, I promise it won't happen again."

I replied, "I would like to believe that, but if I recall correctly, this is your third infraction of various kinds at my school. The first was plagiarizing an essay, and the second was a hazing incident."

She hurried to defend herself. "I apologized for the plagiarizing and wrote a thousand lines on the chalkboard. I was in the tenth grade and stupid. The hazing was just harmless fun, and it happened last year."

I gave her a stern look as I replied, "A girl hospitalised with alcohol poisoning isn't what I call harmless fun."

Realizing I wasn't remotely amused, she shifted her tactics. "I know. I felt so bad for that afterwards, but we just didn't realize she couldn't handle her liquor."

Ignoring her lame rationale, I continued, "So today is strike three. You know what happens when you reach strike three in baseball, don't you, Ms. Allen?"

"You're out," she whispered. The tears, either real or fake ones for manipulating me, began to form.

"Yes, and right now you yourself are indeed out. And you needn't bother with the waterworks, they may have served you well in the past, but they won't cut it with me."

The tears stopped as quickly as they'd begun.

"And 'out' in school administration terms means either temporary suspension or permanent expulsion, Ms. Allen."

"W-w-what?" the pretty blonde gasped, her eyes suddenly grown big.

"The policy is crystal clear, Ms. Allen. I didn't write it, but I do enforce it."

A frantic look in her eyes emerged, and she pleaded, "But there must be something you can do."

I shrugged, "Oh, there are lots of things I could do, but why would I want to?"

Catching my implication, she smiled for the first time in a while, and resumed employing her sexual wiles, her voice dripping with seduction. "If I take your meaning, there must be something I can do to convince you to go to bat for me, Mr. Stanford."

I stood up, startling her, and replied, "I could overlook this infraction I suppose, but the price will be extreme."

"I'll do anything you want, Mr. Stanford," she smiled, thinking I was going to make her give me a blowjob, or maybe I wanted to fuck her... neither of which she'd mind doing in the least.

"The word 'anything' is all-encompassing and dangerous, Ms. Allen," I warned, standing in front of her and looking down at her upraised face.

She repeated, unable even to begin comprehending what I had in mind, "Nevertheless, for you I promise to do anything, Mr. Stanford." Confident in her sexual irresistibility, her hand went to the erect cock in my pants. Feeling my nine-inch cock, she purred, "Hmmmm, impressive."

"So I've been told, " I agreed smugly.

"So... is there anything I can do for you, Mr. Stanford?"

"You really are a slut, aren't you, Ms. Allen?"

"Excuse me?" she replied, shocked at my sudden name-calling.

"You're still pretty young. How many guys have you fucked so far?" I asked, beginning my interrogation in earnest.

Her hand left my trousers, but she didn't reply.

"And how many cocks have you sucked?" I asked, continuing my verbal assault.

"Mr. Stanford, please stop asking me such questions," she begged, actual tears now forming in her eyes.

"Ms. Allen, let's make this crystal clear. If you don't wish to get suspended or worse, you will do exactly as I tell you. Is that clear?"

"Yes, but I don't understand!" she replied. "What do you want?"

"You're a slut, and I could make good use of having my very own personal cheerleader slut," I explained as I unbuckled my belt.

"Please don't call me a slut," she whispered.

"But you are one, aren't you? So I'll ask you again... slut: how many boys have plugged your cunt so far?" I asked, my pants falling to the floor.

"A dozen or so," she whispered, humiliated to admit it.

Releasing my cock from my boxers, I asked, "and how many cocks have you sucked?"

"Maybe a dozen and a half," she admitted.

"Then you may add one more to that tally, Ms. Allen." I grabbed her shoulders and gently pushed her down to her knees.

She looked up, her left hand gripping my cock, "If I suck your cock, you won't suspend me?"

"Not exactly. If you do everything I tell you until you graduate, then I won't suspend you," I clarified. "Now get sucking, slut."

She leaned forward and took my cock into her mouth. For someone who'd sucked more than a few, she really was an amateur at it. She had no style, no steady rhythm, and no ability to deep throat. She would clearly require a lot of practice.

After a couple of minutes of her sloppy cock sucking, I said, "For a slut, you need some real work on the best ways to suck off a man."

She quit sucking me and said, her confidence returned, "I've never had any complaints before."

"Well I'm a man, not a boy, and I expect more. I expect you to worship my cock. To take all of it down your whore mouth, to bathe my cock with your saliva, and to establish a constant rhythm. It should feel to us both like I'm fucking your mouth."

Insulted, yet seeming determined to prove me wrong, she began to bob up and down at a steady pace, and although she never got all of my nine inches in her mouth, she did manage eight. I moaned, "That's better slut, you may make a good cocksucker yet."

This only seemed to excite her more, and her hand disappeared under her skirt.

My balls boiling, I demanded, "I'm going to come in your mouth soon, my slut. Don't you dare waste a drop."

Impressively, she continued her eager bobbing, and soon was rewarded with my salty seed. She didn't miss a beat as I coated her throat, and I figured I might need to reassess her cocksucking talents.

Once I was spent, I pulled out of her mouth and demanded, "Bend over my desk."

Clearly horny now, and I imagine desperate to finish the fuck she'd started over an hour ago, she eagerly complied.

I raised her skimpy cheerleader's skirt, removed her panties and caressed her tight ass. I slid two fingers inside her damp pussy, and she let out a pleasured moan. I pumped her cunt for thirty seconds, then pulled out and used her juices to lubricate her ass.

"W-w-what are you d-doing?" the pretty cheerleader stammered in a panic.

"Since your cunt has been used way too many times for me to feel safe using, I'm preparing your ass for my cock," I replied casually.

"No. I don't do anal," she refused adamantly.

I chuckled, "I wasn't asking your permission. You do whatever I say, or you either get suspended or expelled."


"Butt... yes, nice word choice. But what would mommy and daddy say if they knew you'd fucked some nerd at school?"

"My dad is dead, asshole," she threw back at me with a glare.

I replied, "Be careful how you talk to me, slut. I can still expel you whenever I want."

Suddenly defiant, she countered, "Then I'll tell on you."

I laughed again. "Nice try. Butt who are people going to believe, the respected principal, or some slut cheerleader?"

Shifting from confident to desperate, she pleaded, "Okay, you win. I'll suck you off again."

"Oh, I know you will, and often," I agreed, "but right now you're going to become my ass slut. Have you been back door fucked yet?"

"God, no," she replied, clearly repulsed by the thought.

"Good. I like being the first," I smiled. "Now bend over again, like a good slut."

Tears began streaming down her face as she obeyed while pleading, "Please don't, sir!"

I ignored her plea and slid two fingers rather easily inside her pussy. I asked, "Why are you so wet?"

She let out an involuntary moan.

"Is it because you're excited about your first ass fucking?" I asked, pumping my two fingers in and out of her pussy.

"Noooo," she moaned, unable to hide how much she was enjoying my fingers.

I pulled out and placed a slippery finger at her virgin puckered entrance and slowly pushed it inside. She whimpered slightly as my finger broke through the tight resistance. "Aaaaah, please stop," she begged.

"I'm only just beginning," I said, pushing my finger deeper into her.

"It hurts," she whined.

"You'll soon find the pain is temporary, my dear. Or as Coach Watters always says, 'no pain, no gain.'"

I wiggled my finger around, slowly expanding her tight asshole.

Her whimpers of pain continued as I pointed out, "This slight pain is way more tolerable than if I just went ahead and shoved my cock up your tight ass, my dear."

Again she pleaded. "I can get you money. What do you want?"

"Your ass, Ms. Allen," I replied, "no charge," and her tears again streamed down her face.

I wiggled my finger a bit more before pulling out and quickly adding a second finger. Fuck, she was tight.

She screamed, "Oh my God, I can't take it anymore."

I smiled as I pondered the fact that next was my cock, which was longer and wider than my two fingers. Ignoring her pleas yet again, I continued penetrating her with my fingers while wiggling them inside her tight butt.

Her screaming simmered down to whimpers as my two fingers disappeared between her tight ass cheeks. I explained, "Ms. Allen, your ass is getting used to being widened, or as the books call it, gaped."

"It still hurts," she whined.

"As much as it did at first?" I asked.

"No," she admitted, realizing that for the first time.

"Just relax, and I think you will soon feel a shift from slight burn to sweet tingle," I explained.

I continued the wiggles inside her sweet ass slowly widening her. Her whimpers continued, yet her complaining had ceased.

Finally, content I could fit inside her virgin ass with little effort, I pulled my fingers out and checked out her opened ass. It would still be a tight squeeze, but I liked that.

I got behind her, my nine-inch cock ready for action. She looked back scared, her puppy dog eyes silently pleading me to reconsider, but I just stared back. I wasn't going to lose face to her, like I imagine many guys had before me. For as long as it lasted, I'd call all the shots in this... affair?

Her perfect ass looked so deliciously inviting. Pulling her ass cheeks apart, I astonished her by burying my face between them and slightly rimming her gaped ass. She let out a surprised moan as I teased her puckered hole. Swirling my tongue, her anal resistance weakened as I slid a forefinger back inside her ass. She again whimpered, although now it sounded more like a whimper of pleasure than of pain. I wiggled around before sliding a second finger in.

"Aaahhh," she let out, as I widened her virgin ass for my cock.

I explained, "Good news, Ms. Allen, your tight ass is almost ready for my cock."

"Oh God," she moaned, as I explored her insides with my fingers.

Finally confident that I'd prepared her as best I could for her anal deflowering, I pulled my fingers out and moved my cock back into position. Her ass immediately tightened, so I explained, "This will feel a lot better to you if you relax, Ms. Allen."

Although I could see and feel her nervousness, she did relax the best she could as I pushed forward, ever slowly breaching her tight entrance.

A whimper escaped her lips as she grabbed the corner of my desk for stability. Not wanting to hurt her more than I already had, I continued my anal invasion at a snail's pace. Her whimpers were constant, yet not the kind of howls of pain she'd indulged in earlier. It was obvious she still felt some discomfort, but now also some pleasure. I was halfway in when I heard her first moan, and a smile crossed my face. Most girls may deny this, but once they've felt a big hard cock up their backdoor, they're addicted. I began slowly fucking her ass, each stroke going deeper into foreign territory. The mixture of whimpers and moans as this 18-year-old attempted to deal with her mixture of pleasure and pain was incredibly hot. I'd fucked some pretty girls in my life, and taken a few anal cherries as well, but Dallas was the hottest and tightest I'd ever had. Luckily I wasn't 18 anymore, so I could control my orgasm, as I focused on making this blonde bombshell into my new anal slut.

Each push forward widened her no longer virgin back door and caused a whimper to escape the blonde's sweet lips. Slowly but surely, over fifteen minutes, the girl took all of my cock, and once it was completely buried in her ass, I asked, "How does my cock feel in your ass now, Ms. Allen?"

Her breathing was already erratic as she managed to say, "I-um-it doesn't hurt as much as I thought it would."

"Does it feel good?" I asked, leaning forward a bit, going even deeper.

"Aaaaah, it feels ok," trying not to give me a win.

I promised, "Don't worry, Ms. Allen; pretty soon it will feel lots better than ok."

Determined to keep my promise, I began taking long, slow strokes inside her ass. I wasn't fucking her really, but rather prepping her for the fucking that was to come. Slowly her whimpers faded and were replaced by moans, and just like all my other first-time anal sluts, she started to really enjoy the sensations of my cock up her ass.