Blackmailed: Cheerleader's Cherrybysilkstockingslover©
Summary: A Principal disciplines a stuck-up hot bitch cheerleader.
Note: This story is dedicated to Doc who inspired this ass-centered story.
Note 2: Thanks go to Estragon for his copy-editing work.
Blackmailed: Cheerleader's Cherry
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."
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."
Insulted, yet seemingly determined to prove me wrong, she began to bob up and down at a steady pace and although she never got all nine- inches of me in her mouth, she did get eight. I moaned, "That's it slut, you may make a good cocksucker yet."
This only seemed to excite her more as 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 miss 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 have to reassess her cocksucking talent.
Once all spent, I pulled out of her mouth and demanded, "Bend over my desk."
Clearly horny now and I imagine desperate to finish a fuck she started over an hour ago, she eager complied.
I lifted up her skimpy cheerleader's skirt and caressed her tight ass. I slid two fingers inside her damp pussy and she let out a pleasurable moan. I pumped her cunt for thirty seconds and pulled out and used her juices to lubricate her ass.
"W-w-what are you doing?" the pretty cheerleader stammered in a panic.
"Well your cunt has been used way too many times for me to use and feel safe in, so I am going to get your ass ready for my cock," I replied rather casually.
"No. I don't do anal," she adamantly refused.
I chuckled, "I wasn't actually asking your permission. You do what I say you do or you are suspended."
"But what would mommy and daddy say If they knew you had 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, "I will tell on you."
I laughed again. "Who are people going to believe, the respected principal or some slut cheerleader?"
Shifting from confident to desperate, she pleaded, "I will suck you off again."
"Oh yes you will," I agreed, "but right now you are going to become my ass-slut. Have you ever been fucked in the back door?"
"God, no," she replied, clearly repulsed by the thought.
"Good. I like when I am first," I smiled. "Now bend back over like a good slut."
Tears began streaming down her face as she obeyed while pleading, "Please don't, sir."
I ignored her plea, sliding two fingers rather easily inside her pussy. I asked, "Why are you so wet?"
She let out an involuntary moan.
"Is it because you are excited about your first ass-fucking?" I asked, pumping my two fingers in and out of her pussy.
"Noooo," she moaned, enjoying my fingers.
I pulled out and placed a sticky finger at her virgin puckered entrance and slowly pushed forward. She whimpered slightly as my finger broke through the tight resistance. "Aaaaah, please stop," she begged.
"I am only just beginning," I said, pushing my finger deeper in her.
"It hurts," she pleaded.
"The pain is temporary, my dear. Or as Coach Watters always says 'no pain, no gain.'"
I wiggled my finger around attempting to slowly expand her tight asshole.
Her whimpers of pain continued as I pointed out, "This slight pain is way more tolerable than if I just 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 and her tears again streamed down her face.
I wiggled my finger a bit more before pulling out and quickly added 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 all the while wiggling inside her tight butt.
Her scream simmered down to whimpers as my two fingers disappeared between her tight ass cheeks. I explained, "Ms. Allen, your ass is slowly getting used to being widened or as the books call it gaping."
"It still hurts," she whined.
"As much as it did originally?" I asked.
"No," she replied, realizing it for the first time.
"Just relax and I think you will feel the shift from slight burn to sweet tingle," I explained.
I continued the wiggle inside her sweet ass slowly widening her. Her whimpers continued, yet her complaining had ceased.
Finally, content I could fit in her virgin ass, I pulled my fingers out and looked at her open ass. It would still be a tight squeeze, but that I liked.
I got behind her, my nine-inch cock ready for action. She looked back scared, her puppy dog eyes desperately pleading me to reconsider, but I just stared back. I was not going to lose to her like I imagine many had before me.
Her perfect ass looked so deliciously inviting. Pulling her ass cheeks apart, I surprised her by burying my face between her cheeks and rimming her slightly still gaping ass. She let out a surprised moan as I teased her puckered hole. Swirling my tongue, her anal resistance weakened as I slid a finger back in her ass. She again whimpered, although it sounded more like a whimper of joy than 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, "It's ok, 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 I had prepared her as best I could for her anal deflowering, I slid my fingers out and quickly moved my cock into position again. Her ass immediately tightened, but I warned, "This will go a lot better if you relax, Ms. Allen."
Although you could see and feel her nervousness, she did relax the best she could as I pushed forward, ever slowly, breaking past her tight entrance.
A whimper escaped her lips as she grabbed the corner of my desk for grip. Not wanting to hurt her, I continued my anal invasion at a snail's pace. Her whimpers were constant, yet not the kind of howls of pain that she had earlier. It was obvious she felt some discomfort, but it was also obvious she was feeling some pleasure. I was half in when I heard the first moan and a smile crossed my face. All girls deny it, but once they have felt a big hard cock up their backdoor, they are addicted. I began to slowly fuck her ass, each forward stroke going deeper into foreign territory. The mixture of whimpers and moans as the 18-year-old attempted to deal with the mixture of pleasure and pain was incredibly hot. I had fucked some pretty girls in my life and taken a few anal cherries as well, but she was the hottest and tightest I had ever had. Luckily, I wasn't 18 anymore and could control my orgasm as I focused on making this blonde bombshell my new anal-slut.
Each push forward widened her no longer virgin back door and allowed a whimper to escape the blonde's sweet lips. Slowly, but surely, over fifteen minutes, the young girl took all my cock and once completely buried in her ass, I asked, "How does my cock feel in your ass, 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."
I promised, "Don't worry, Ms. Allen, pretty soon it will feel a lot better than ok."
Attempting to keep my promise, I began 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 my moans and like the other first time anal sluts, she started to like the sensation of the cock up her ass.
I continued the slow burn, waiting for the words that always, always finally come. The anal tease lasted a couple of minutes more, her moans increasing before she begged, "Please, harder, fuck me harder."
"Fuck what harder?" I asked, wanting to hear the 18-year-old say it.
"My ass, fuck my ass, please," she begged.
"But I thought you said anal sex was disgusting?" I questioned, actually slowing down.
"Oh God, please don't stop. You were right, sir. It feels so fucking good."
"Your cock in my ass," she admitted frustrated, wanting desperately to be fucked hard, fucked like a slut.
Satisfied with the declaration, I picked up the pace substantially. Her moans accelerated, and she was a screamer; thank goodness it was Friday night and teachers exited this place faster than a teen boy shoots his first load inside a girl.
"Oh yes, oh, oh, God, it-it-it feels so good," she moaned, "So fucking good."
"But only sluts like a cock in their ass, Ms. Allen," I pointed out.
"I'm a, I'm a, I'm a slut then," she admitted, adding, "Your slut, Mr. Stanford."
"And this ass is mine whenever I want it?" I asked as I begin really pistoning inside her ass.
"Oh yes, it is, it's yours," she struggled to offer, moaning like a boar in heat.
"You're my slut, Ms. Allen?" I asked.
"Yes, Mr. Stanford," she moaned.
"My personal fuck-toy?" I pushed.
"Oh God yes," she eagerly agreed.
"My anal cum deposit?" I questioned.
"Oh yes, whenever you want," she moaned, her left hand now frantically rubbing her pussy.
"Don't you come till I allow it," I ordered.
"Oh god, I'm so close, Mr. Stanford," she whined. "Beg for it, Ms. Allen," I demanded.
"Oh please sir. Can I come like a slut?" she moaned, as my cock continued hammering away in her ass.
"You can come when I do, slut," I grunted, before adding, "and I am close."
"Okkkkkk," she moaned, still rubbing herself.
Thirty seconds later, both of us doing all we could to come, I said, "Get ready, slut. Here it comes, baby."
"Oh yes, fill my ass with your cum," she moaned, so opposite to her earlier rejection.
"Get ready to come, slut," I demanded, "In five."
"Four," I said, as her screams echoed.
"Two," I grunted, my ball boiling over.
"One," I declared, my cum exploding out of me and inside her tight ass. "Now, slut, cum now."
A couple of seconds later, the 18-year old quaked as an intense orgasm exploded out of her. She screamed, "Aaaaaaah, fuuuuuuuck, I'm cuuuuuuuuuuuuuuuming. Fuck, fuck, yes Mr. Sanford!"
As I deposited my load in her, I watched the most animated orgasm in my life. She shook, she screamed, she talked dirty, it was the hottest thing I had ever seen. I finally pulled out and demanded, "Clean my cock, slut."
This time she obeyed with lightning speed as she fell to her knees and took my cock that as just in her no longer virgin ass and began bobbing on it as if to retrieve any last remnants of cum still stuck inside my cock.