Blackmailed: a Cheerleader's Cherry


Caution: This Sex Story contains strong sexual content, including Ma/Fa, NonConsensual, Reluctant, Coercion, Blackmail, Heterosexual, MaleDom, Anal Sex, Teacher/Student, School, .

Desc: Sex Story: A slutty cheerleader is blackmailed by her principal after being caught in the act...her punishment..her virgin ass.

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

Note 2: Thanks go to Estragon for his copy-editing work.

As Principal of the biggest school in our part of California, every day is an adventure. Drug busts, celebrities' kids, drama, cyber-bullying, gangs, I have seen it all. I have had ridiculously attractive mother's flirt with me, and even straight out offer me sex, to not expel their child. I have had very pretty teenage girls offer themselves to me on occasion as well ... but I had always resisted the temptation.

A divorce, a long dry spell, and bitterness at the academic changes being made in my district all coalesced at once and allowed my moral shell to wither ... and when I succumbed ... I really succumbed.

The day it started had been a compete shit-show and 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 room with Markus Zenron ... Markus Zenron? He was our chess champ, and resident geek in every sense of the word. Not in a million years could I have been ready for this. It made no sense. Far as I knew, she was dating Elden Winster, the starting quarterback. I pulled the two into my office and asked the obvious question, ignoring the question I really wanted to ask, "Why would you two choose to fool around in the janitor's room?"

Markus looked like he had already shit his pants and Dallas was already in tears. But fifteen years of this job and I knew those were not real tears, but I-can-cry-on-cue-to-get-out-of-trouble tears.

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

Ignoring the crying girl, I explained, "You understand if this goes on your record, you can kiss Harvard goodbye."

"Y-y-yes, sir," a completely devastated Markus stuttered, like the geek he was.

"I may be able to look past this indiscretion if I could only understand why," I offered, curiosity getting the better of me.

Markus looked down and explained, "Dallas told me to meet her in the janitor's room after school. I thought it was a joke and didn't plan to go, but..."

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

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

"What was true?" I asked.

Dallas finally spoke up. "Don't you dare, Markus."

I glared at the blonde cheerleader, her face a mess from the mixture of tears and make-up. "You can tell your version once he is done, young lady."

She quit although the glares she aimed at Markus would have stopped 99.999% of boys from continuing. "Actually Dallas, go wait outside."

"But," she began to protest.

"No buts, go!" I ordered, my voice rising and my tone daring her to continue questioning me.

Once she left, I said, "Go on, Markus."

"She was asking if the rumour about the size of my um-well-um..." the shy nerd paused.

"Your penis?" I queried.

"Yes, sir," he answered.

"So she wanted to see if the rumour was true about the size of your penis."

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

I smiled, "How long had you two been in the room before you were caught?"

"Less than ten minutes, sir."

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

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

"Hoe long had the two of you been having actual intercourse before you were caught?"

"Only a couple of minutes," he replied.

Poor fucker. Get to fuck the hottest cheerleader in school and get caught only a couple of minutes in. Life is a bitch. "Tell you what, Markus. You are a good kid and I would hate for you to lose your free ride to Harvard. Can you keep a secret?"

"Yes sir," he replied, the glimmer of hope shining eagerly.

"This never happened. No one knows but you, Dallas, Mr. Harkus and myself. So don't let anyone know and I will pretend it never happened."

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

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

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

"You are welcome. Send Dallas in on your way out."

"Yes, sir."

A minute later, Dallas walked into my office and closed the door. She walked to her chair with a sexy wiggle, one I am sure had worked to get her out of trouble in the past. Sitting down, she made sure she showed a lot of leg. I chuckled to myself, thinking she would soon be showing more leg than that.

"Ms. Allen, what are we going to do about this predicament?"

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

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

She quickly defended herself. "I apologized for the plagiarizing one, I was in grade ten and stupid. The hazing was harmless fun."

I gave her a stern look as I replied, "A girl in the hospital with alcohol poisoning is not my version of harmless fun."

Realizing I was not amused, she shifted her theory. "I know. I felt so bad for that, but we just didn't realize she couldn't handle her liquor."

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

"You're out," she whispered. The tears, either real or fake to manipulate, began to form.

"Yes, you are out. And you can stop with the waterworks, they may have worked for you in the past, but it won't cut it with me."

The tears stopped almost as quickly as they began.

"And 'out' in school terms means suspension or expulsion, Ms. Allen."

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

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

A frantic look in her eyes emerged as she pleaded, "There must be something you can do."

I shrugged, "Oh, there is lots I can do, but why would I?"

Catching on to my implications, she smiled for the first time in a while, and using her sexual wiles, her voice dripped with seduction, "There must be something I can do to change your mind, Mr. Stanford."

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

"I will do anything you want, Mr. Stanford," she smiled, assuming I was going to make her give me a blowjob or maybe fuck her.

"The word 'anything' is a very dangerous word, Ms. Allen," I warned, standing in front of her and looking down.

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

"So I have been told, " I smugly retorted.

"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 the sudden name-calling.

"How many guys have you fucked?" I continued the interrogation.

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

"How many cocks have you sucked?" I asked, continuing the verbal assault.

"Mr. Stanford, please stop," she requested, real tears now forming.

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

"I don't understand?" she replied.

"You are a slut and I could use 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, aren't you? I will ask you again how many boys have plugged your cunt?" I asked, my pants falling to the ground.

"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?"

"Even more," she admitted.

"Well add one more to your tally, Ms. Allen." I grabbed her shoulders and gently pushed her onto her knees.

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

"No. If you obey everything I ask you to do, I won't suspend you," I clarified, before instructing, "Now get sucking, my slut."

She leaned forward and took my cock in her mouth. For having sucked so many, she really was an amateur at it. She had no real style, no constant rhythm and no ability to deep throat. She would clearly need a lot of practice.

After a couple of minutes of her sloppy cocksucking, I said, "For a slut, you sure need some work on the proper way to suck off a man."

She quit sucking me and said, her confidence back, "I have never had any complaints before."

"Well I am a man, not a boy and I expect more. I expect you to worship my cock. To take it all down your whore mouth, to bathe my cock with your saliva, and to get in a constant rhythm. It should feel like I am fucking your mouth."

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