Blackmailed: Cheerleader's Cherry

I continued my slow burn approach, waiting for the words that always, always eventually came. 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 harder, please," she begged.

"But I thought you said anal sex was disgusting?" I asked as if she were being confusing, and unhelpfully I slowed down.

"Oh God, please don't stop. You were right, sir. It feels so fucking good."

"What does?"

"Your cock in my ass," she admitted, frustrated, wanting desperately to be fucked hard, fucked like a slut.

Satisfied with her declaration, I picked up the pace substantially. Her moans accelerated, and it turned out she was a screamer; thank goodness it was Friday evening, and the teachers exited this place faster than a teenage 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 cocks in their asses, Ms. Allen," I pointed out.

"I'm a... I'm a... then I'm a slut," she admitted, adding, "and I'm your slut, Mr. Stanford."

"And you're telling me this ass is mine whenever I want it?" I asked, as I began really pistoning inside her ass.

"Oh, yes it is, it's yours," she struggled to offer, moaning like a sow in heat.

"So you're my slut, Ms. Allen?" I asked.

"Yes I am, Mr. Stanford," she moaned.

"And my personal fuck toy?" I pushed.

"Oh, God yes," she agreed eagerly.

"And also my anal cum deposit?"

"Oh yes, whenever you want me," she moaned, her left hand now frantically rubbing her pussy.

"Don't you dare come until I say you can," I cautioned.

"Oh god, but I'm so close, Mr. Stanford," she whined.

"Then beg for it, Ms. Allen," I demanded.

"Oh please sir. Can I please come like a slut?" she moaned, as my cock continued hammering away in her ass.

"You may come when I do, slut," I grunted, "and no worries, I'm very 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 we come, baby."

"Oh yes, fill my ass with your cum," she moaned, totally opposite from her earlier refusals.

"Get ready to come, slut," I demanded, "In five."

"Four," I said, as her screams echoed around my office.

"Three."

"Two," I grunted, my balls boiling over.

"One," I declared, my cum exploding out of me and inside her tight ass. "Now, slut; cum now."

A couple 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 into her, I watched the most animated orgasm in my life. She shook, she screamed, she talked dirty, it was the hottest thing I'd ever seen. I finally pulled out and demanded, "Clean my cock, slut."

This time she obeyed with lightning speed, falling to her knees and taking my cock that was just in her no-longer-virgin-ass and beginning to bob on it, possibly endeavoring to retrieve any last remnants of cum still upstream inside my cock.

Finally spent, I pulled up my underwear and pants and said, 'You understand this wasn't a one-time thing, slut?"

"Yes, sir," she agreed, still on her knees.

"And I require you to date Markus for the rest of the semester," I announced. "Just not in the janitor's closet anymore."

She stammered, "W-w-what?"

"Yes, I think he'll be good for you. The only cocks allowed in your three cum deposit holes will be mine and your new boyfriend Markus's."

"But that will ruin my reputation," she whined.

"I doubt it. If anything, it will save you from the shallow path you were pursuing," I countered.

Still on her knees, she stared up at me, dumbfounded.

I smiled, "Unlock your phone and hand it to me."

She stood up and went to her phone. From behind, I could see my cum leaking out of her ass. She unlocked and handed me her phone. I looked up Markus' phone number and dialled it. I handed her back the phone and instructed her, "Ask for Markus."

Although I could tell she wasn't enthusiastic, she did as I'd instructed. "Hi, is Markus home? May I speak to him?"

I took the phone back. Once Markus was on the line, I explained my plan. "Hi, Markus. It's Principal Stanford. I've dealt with Ms. Allen, and we've come to a mutual understanding that we like, and we think it will please you too. She's agreed to be your girlfriend... with benefits... for the rest of the semester, and we three will keep your little indiscretion a secret. Although the next time you want to fuck her, please do it somewhere other than my school."

He asked, stunned, "Are you serious, Mr. Stanford?"

I responded, "Deadly serious, Markus. You've worked hard for all your life to be a top student, and you deserve to be rewarded. Your reward is to enjoy unlimited sex with the hottest slut in the school. She will treat you with respect, encourage you to hang out with her friends, defend you if some of the so-called 'cool kids' try to bully you, and she'll fuck you whenever you want. If she disobeys you or mistreats you in any way, please let me know, so I can reprimand her accordingly. Is all of that clear and acceptable?"

He stammered, "Y-y-yes, sir."

"You two should go on a date tomorrow night. She will pick you up at 6 pm, and she will take you out. Again, you may use her however you wish. She's a decent cocksucker, but could use some practice. Her pussy has been used a fair amount, so I encourage you to make sure you get her tested before drilling that hole, but her ass is fucking heavenly, and I highly recommend it. Actually, Ms. Allen: please tell Markus you want him to fuck your ass tomorrow."

I handed her the phone, and she looked at me with a look of stunned shock. I gave her a hard look that told her just to do as she was told.

She paused, but began, "Markus, I'm so sorry for how I treated you in the past, and I'd love for you to be my boyfriend. Who? Elden? No, he's history; I want you. Brains over brawn, you know."

My cock hard again, I figured I might as well deposit one more load into my cheerleading slut. I snapped my fingers and pointed to my desk, and she obeyed while continuing to talk on the phone with her new boyfriend. "Tomorrow night I'll pick you up like Principal Stanford said, and take you out for supper at McClarens, so dress up nicely. Then maybe a moviiiiiiiiiiiie."

My cock slipped back into her ass. I said, "Make sure you tell him what you want him to do to you."

She moaned, as I began deep thrusts into her ass. "Oh God, Markus. Tomorrow I want to feel your big cock inside me anywhere you want to puuuut it. Shove it in my mouth, my pussy, or my ass. I just want to feel your big cock inside me. Make me your sluuuuuuuut."

I slapped her ass. "Say goodbye, slut. I want you focused now."

"Bye, Markus. I'll see yoooooou tomorrow; ok, lover?" she moaned.

She dropped the phone on the desk and begged, "Oh god, thank you, Mr. Stanford, I don't know what you've done to me, but I fucking loooove it."

"You were already a slut, Ms. Allen. I'm just making sure you get treated like one," I explained.

Clearly getting off from the ass fucking, she moaned, "Oh god yes, I'm your slut."

"And Markus's slut too," I corrected her.

"Yes, sir. I'll fuck him, I'll suck him, I'll make him popular, have threesomes with my girlfriends... all for you, sir, all just to feel your cock inside me again and again," she screamed as another orgasm began to build in my little anal-slut.

"Come for me slut, come... again... while I fuck your ass... again," I demanded, sweat dripping down my forehead while I hammered her as hard as possible.

She began rubbing her pussy and begged, "Harder, sir, oh fuck, yes, your cock feels so good in my ass, so fuuuuuucking good!"

"Come now, slut," I demanded, grabbing her hair.

"Oh yes, oh god, oh yes, oh, oh, oh, 1uuuuuuuuck," she bellowed, her scream ricocheting off the walls.

I pulled out, sat down on my office chair and demanded, "Straddle my cock, slut."

She struggled to stand up, clearly exhausted, but still managed to stagger backwards towards me. I grabbed her ass and lowered her slowly onto my cock. She whimpered, this new position stretching her ass in new ways. Then after a couple minutes of getting used to her new position, she began to ride my cock. Watching one of the most beautiful high school students I've ever met riding my cock in her ass was fucking hot, as were her increasing moans. She held onto my desk for balance as she began bouncing on my cock, taking it deeper than she had before.

She squeezed out whimpers of pain, but like a trooper, she maintained a steady pace on my cock. Gradually her whimpers became moans, and she again became animated. "Oh fuck, sir, promise me you'll fuck me again! Oh god, I didn't know it could be this good! Fuck, fuck, oh god, you're inside me so deep!"

Finally getting close, I held her steady on my lap, my cock buried completely inside her. I asked, "Are you ready for it, slut?"

"God yes," she answered, having no idea what I was about to do.

I gripped her shoulders and bucked my ass up, making my cock pound deeper inside her than anyone would think possible.

Her screams once again filled the room. "Oh fuuuuuuuuck, it hurts so good, so fucking good!"

I continued the upward thrusts into my slut's ass. Each thrust had her emitting incomprehensible sounds. "Aaaaaahh!" Another thrust. "Arrrrrrrrg!" Another. "Oh myyyyyyyyyy!" The sexy screams of her pleasure and pain were so hot that soon my balls were again bubbling, I only wished I could have seen her expressions, although later on, my security camera would entertain me for hours.

I demanded, "Beg for my cum, my slut."

She begged, "Oh sir, shoot your cum up my slut ass. I'm your ass slut, your cheerleading slut, and oh god, I'm going to come again."

A few more thrusts were all it took before I surprised her by demanding, "On your knees, slut. It's time to coat your face with my cum."

She quickly fell to her knees, her mouth wide open, her blue eyes staring up at me as I stroked my cock right in front of her. Her dirty talk continued as she fingered herself. "Mr. Stanford, come on your slut. Cover my face with your cum. I want it, sir, I want it so fuuuuucking bad."

It was too much, and I shot my third load of the evening all over her face. Some hit her hair, some her forehead, but most covered her nose, lips and chin. She scooped up all of my cum she could reach, and stuffed it into her mouth, just like any good slut would do, before taking my spent cock back into her mouth.

Finally satisfied, I demanded, "Make yourself come again for me, slut."

She instantly sat on my desk, fell onto her back, shoved two fingers inside her cunt and pumped herself furiously. In less than a minute, her orgasmic scream once again echoed through my office. I watched her twitch and writhe, oblivious to how slutty she looked.

Once she recovered, I said, "May I assume you won't be getting into any more trouble, Ms. Allen?"

"Oh, no sir," she smiled, still lying on the floor, her legs spread wide open, her face shiny with my cum. "I've learned my lesson."

"Excellent," I smiled, "Of course, I think it best to be proactive with your case."

"How so, sir?" she asked, her smile so seductive I thought I might get hard again.

"Well, I think for starters, we should meet for weekly counselling every Friday, beginning right after school, the same as today," I suggested.

"I think that's an excellent idea, sir. I'd hate to regress because I was lacking proper reminders," she smiled, her fingers still inside her cunt.

*****

We continued her discipline every Friday for the rest of the school year, and she and Markus became the odd couple of the school. But because of her popularity, the other students never questioned her choice of a boyfriend, and Markus became very popular... the two of them even serving as homecoming king and queen at prom.

At prom, with my cum in her ass, after being presented as prom queen, Dallas introduced me to her mother, who was a popular journalist, a dead ringer for her daughter and, as I recalled, a widow.

A couple ours later, I deposited a load of cum in Mrs. Allen's ass...but that's another crazy story.

The End... for now... until Mrs. Allen's story in part 2 Cheerleader's Mom.