Blacmailed: Cheerleader's Mom

Summary: Unprincipled Principal also forces the Cheerleader's Mom to become his eager ass slut.

Note 1: Although not completely necessary, I recommend you read

Blackmailed: Cheerleader's Cherry

first, as it explains how Principal Stanford blackmails the popular head cheerleader into becoming his personal ass slut.

Note 2: As always, I would like to thank Estragon for his copy-editing expertise, and LaRascasse for plot suggestions.

Note 3: Updated with a new epilogue December 2012.

Note 4: Updated by Tex Beethoven August 2022.

Blackmailed: Cheerleader's Mom

Prom was on a Friday and as usual, in the late afternoon Dallas, the head cheerleader, was in my office taking my cock in her ass. Her training had been completed for over a month, so now she could easily take all nine inches of my cock up her backdoor, and she was in love with my cock... with me not so much, but at least she willingly did whatever I told her to... what can I say?

Having caught her in a compromising situation a few months ago, I'd blackmailed her into becoming my little anal cheerleading slut, and I'd weaned her away from her diva princess personality.

She'd dumped her football player boyfriend as I'd instructed, and started dating a geek named Markus, the other participant in the compromising situation that had ensnared Dallas for me. He was average looking, a genius who'd already been accepted into Harvard, and was very, very well-endowed. Dallas was so popular that instead of being shunned for dating a geek, she became even more popular, as did Markus. They came across like the leads in an eighties teen comedy, or a real life version of Revenge of the Nerds.

I saw in Markus a bit of myself back when I was a teenager, since I didn't come into my own until college. So I enjoyed assisting him in reaping his newfound glory.

Dallas had become a perfect little ass slut, and her nasty talk always got me revved up. Dallas was currently bent over my desk, still wearing her cheerleader's outfit with my pole buried in her ass, begging, "Harder, Mr. Stanford, fuck your slutty cheerleader's ass harder."

She'd become such an ass slut that she always needed to be hammered. She didn't want to be made love to, she wanted to be ass fucked... hard. She was the perfect fuck: drop dead gorgeous, a great cocksucker who loved to swallow (after we'd completed her training of course), she had a tight cunt, even though it was well used, and her perfect ass could take all nine inches of my big cock. Added to that, she was submissive deep down once we'd you gotten past her diva persona, she had the filthiest mouth of any chick I'd ever fucked, and well... like I said, she was the perfect fuck. Her graduating in less than a month was disappointing, since she'd really livened up all my Friday evenings.

She begged, "Fuck me on the floor, sir, I need your cock deeper inside me!"

We tried a new position last week that she'd found online for maximum anal penetration, and it got her off like gangbusters. I pulled out of her ass, and she quickly repositioned herself onto her back on the floor. Being a cheerleader, Dallas was ridiculously flexible, and she stuck her feet up in the air and even behind her head. I'm not shitting you, it was the fucking hottest thing ever!

Looking down at my sexy human pretzel, I was treated to a perfect view of her gaped asshole. She looked up at me, her hunger for my cock obvious, as she moaned with her hand somehow managing to reach her pussy, "Please fuck my ass, Mr. Stanford, I need to get home and get ready for prom soon."

I asked, "Are you saying that prom is more important than being my ass-slut?"

She quickly apologized, her tone seeming sincere, "Sorry, sir, nothing is more important than pleasing you."

"I was just kidding," I smiled, "you only get one prom in your life. However, I'd like a favour in return."

"Sure! Name it."

Well, I noticed your mother's name on the list of volunteer chaperones, so I'd like you to introduce me to her."

"Sure, I can do that. But why?"

"Because I want to fuck her."

"WHAT? I can't promise THAT!"

"No, no, I'll do the seducing, you just need to introduce us."

"Okay, sure. That sounds like fun! But now I'd like a favour."

"Which is?"

"I want to spend my prom with your cum in my ass," she said, her nastiness never lacking for material.

"Okay, then let's make your prom wish come true right now," I offered, bending down to fill her in the most satisfying way possible.

My cock easily filled her gaping ass, and she let out a glass-shattering scream, as all my nine inches filled her. "Aaaaaaaaahhhhhh fuuuuuck," she screamed, "it feels so good!"

Once I was deep inside her, I began pounding her ass, my body slamming into her forcefully with each hard, deep thrust. Her breathing increased, as I literally fucked the shit out of her. "Fuck, your ass is so tight," I grunted, knowing I wouldn't last very long in this position and at this pace.

She rubbed her clit frantically, and while she orgasmed from getting her ass reamed, her anal muscles tightened around my cock, milking my bone. The intensity became too much for me, and while her cum exploded from one of her holes, I blasted my cum into the other one.

Once we'd both recovered, she weakly got up, with her make-up a mess. She looked into her compact mirror and joked, "I look exactly how I feel."

"Until next week," I said, getting dressed.

"I'll be here," she promised giddily, before leaving to get ready for prom, where she would no doubt win prom queen. The only question was whether she'd made Markus popular enough to become prom king as well.

I cleaned up, and went home to shower before I needed to be back at the school in a couple of hours.

.....

As expected, Dallas was the prom queen, and she looked like a princess in her bright pink gown. I smiled, knowing that beneath that innocent-looking exterior was an ass slut who still had my cum in her ass from this afternoon.

After the prom's king and queen dance (with Markus being the king, by the way), which really showcased Dallas's popularity, Dallas took me aside and introduced me to her Mom.

My cock swelled instantly, since her Mom was the spitting image of Dallas. In other words, her Mom didn't look a day older than her daughter, and they could have passed for identical twins. Dallas said formally, "Mr. Stanford, I'm pleased to introduce to you my mother, Devon Allen."

I extended my hand, recalling she was a widow, my brain already scheming about how to fuck her, "It's very pleasant to meet you, Mrs. Allen."

"Please call me Devon, Mr. Stanford," she replied politely, her Texas accent enhancing my fantasy about fucking her.

"Well, if you're willing for us to relate on a first name basis, then I'll be grateful if you call me Warren," I smiled back, already plotting my blackmail scheme.

"Well, Warren," she smiled, clearly accustomed to using her charm for winning over any man (her beauty always giving her a tremendous head start), "Dallas tells me you've completely changed her outlook about school."

"Well..." I shrugged nonchalantly, glancing at Dallas, who had a devious grin on her face.

"No, I'm serious. Dallas was a real handful, but since you kept her after school that day a few months ago, she's become a totally different person. I can't thank you enough," the naïve mother gushed, unaware that she was thanking me for fucking her daughter's ass.

I kept the inside joke going between Dallas and myself by replying, "Oh trust me, the pleasure was all mine. Once I got past her diva-ish resistance, she became quite the eager learner."

Dallas was almost unable to restrain herself from bursting out laughing, but she managed to add with a straight face, "Yes Principal Stanford, thanks to you, I've become an enthusiastic student!"

I added, "And she never holds back until she's mastered all her objectives."

This time Dallas couldn't hold back from laughing as she added, her innuendo dripping as she stressed the word 'coming', "Yes, I just keep

coming

again and again."

Mom, oblivious to the innuendo, suggested, "Well Warren, if there's ever anything I can do to thank you, just let me know."

Certain I was going to fuck her tonight, I smiled, "Actually, now that you mention it, I was hoping you might help with some PR for the school. Maybe you could publish a piece about our various achievements?"

Her eyes lit up. "What a great idea! What do you have in mind?"

I glanced briefly at Dallas before turning back to her motherly twin and asking, "Do you have a few minutes right now?"

Looking to her daughter, she asked, "Dallas, do you mind?"

Dallas said, "Oh no, go right ahead. Markus wants to dance some more, and then we're leaving for the all-nighter, and I'll be getting home sometime tomorrow morning. So go ahead and discuss those PR matters with Principal Stanford by all means; I've learned he's very thorough whenever he's working on a piece."

Did she mean whenever I was working on a piece... of ass? Okay, the subtlety was gone, especially since she'd just made it clear she'd be waking up tomorrow morning next to Markus, probably in a hotel room. I was pretty sure her mother had also gotten the obvious innuendo about me that her daughter had just tossed at her, but instead of saying anything motherly or prudish, she just gave her daughter a hug, then turned to me and said, her dazzling smile succeeding wonderfully in charming me, "Lead the way, Warren."

I gulped, astonished I hadn't been busted right then and there, and I said smoothly, "Right this way, Devon."

I glanced back to Dallas, who mouthed, "Good luck in fucking my Mom!"

I just smiled and led my MILF to her impending servitude.

Once we arrived in my office, I closed and silently locked the door before sitting down at my desk.

Devon sat down demurely across the desk from me, the same way I imagined she always did. She asked innocently, "So what... exactly... do you do with the students on Friday afternoons?"

"Actually, I only work with your daughter," I admitted.

"Really?" she asked, "nobody else needs the extra help?"

"Oh. I'm sure there are many other students who could use my expertise, but I limit my tutelage to a rare few. Truth be told, your daughter is my first and only private pupilso far," I answered cryptically.

"How so?" she asked, intrigued by my non-answer.

"I could explain, but I think showing you something will be much more informative," I said, standing up and going to my DVD player. I selected a disk labelled Motivation #14, and popped it into the player. Before pressing 'Play', I explained, "There are several different issues that can motivate a student to excel in their studies. Some students will work hard at their schoolwork simply because they enjoy learning, others do it because they need high marks to obtain scholarships, others work hard to pad their resumés, and a very few others require quite unique motivations to reach their potential."

The pretty MILF said, "Well whatever you've been doing to motivate Dallas has really been successful. Her marks are averaging in the eighties for the first time since middle school."

I smiled, "Well, I simply made it clear to her from the beginning that if she didn't get her marks up and keep them up, I'd discontinue her training."

"Her training?" she repeated, surprised by my choice of words.

Pressing 'Play', I stood close to where the mother was sitting, and placed a hand on the back of her neck. She asked, "What are you doing?"

"Just watch, and you'll see," I ordered, massaging her neck while a close-up of her daughter sucking cock began playing. From the camera angle, it was obvious that Dallas was doing the sucking, but the cock could be just about any guy's.

"What the hell is going on here?" she demanded, her typical self control vanished, and she attempted to stand up.

I held her in place and ordered, "Sit back down, and I'll explain."

She sat back down, but started ranting, "What's the meaning of this? I'll have your job!"

I chuckled, "Devon, your daughter is a nasty ass-slut, and she's been one for some time... since long before I entered her life. She was caught having sex with Markus in a janitor's closet, so near the end of a lengthy discussion, I put her in her place."

"In her place? What the hell does that sexist bullshit mean?"

"Well, your daughter was a stuck up, ignorant bitch who thought she ran the school, so I gave her an object lesson about who really runs the school," I explained, cool as a cucumber.

"So in other words you're admitting you had sex with my daughter?" she asked, shocked by this sudden turn of events. We'd started with her flirting me into a position around her little finger, but now she had no control over me at all. The player had been played.

"Yes, and not just once. We've been fucking every Friday afternoon for a few months now," I admitted, "but that isn't the point."

Surprising me by quickly leaning forward and escaping my grip, she snapped, "I don't know what

your

point is, but

mine

is that I'll get you fired forthwith, you fucker!"

I chuckled smugly. "I don't think so."

"Just watch me," she threatened, accustomed to her bitchy threats always succeeding.

"Just get on your knees, slut," I countered.

"What?" she replied, shocked.

"I think that was a simple demand. Get on your knees..." I repeated, then added for emphasis, "...slut."

"How

dare

you speak to me that way?" she rallied back, wounded but still game, as if I'd just slapped her face in public.

"Just kneel. I don't have all night," I sighed, showing my impatience at her disobedience.

"I'm out of here," she said, so angry that smoke was almost shooting out of her ears.

"As you wish," I said, stepping out of her way so she could leave, before tossing out my ace of spades threat. "But if you do, this video of your daughter goes viral."

She stopped at the door, then paused for a brief moment before turning around and asking with a glare, "Are you blackmailing me?"

"Yes, I'd say that's the perfect term for what I'm doing," I replied.

Her strong persona seemed to deflate a bit, as she shifted from dignified to bargaining. "Maybe we can make a deal."

"Sounds good to me," I replied, setting her up perfectly.

"Okay, how much?" she asked.

I laughed. "Oh, I don't want your money."

"You don't?" she said, her face again registering surprise.

"Nope, I want your ass," I revealed.

"What?" she asked, hoping she'd heard me wrong.

"Well, I love fucking your daughter's ass; it's amazingly luscious and tight, but she'll be graduating soon and going away to Harvard with Markus, so I'm going to need a new ass. You look a lot like your slut daughter, your personality is as bitchy as your slut daughter's used to be before I began training her, and I can see that you're a stuck-up bitch who uses her looks to get what she wants, just like your slut daughter used to be," I explained, humiliating her even more.

"How dare you insult my daughter and me like that?" she countered, totally affronted by my assessment.

I sighed. "We could play this game all night, but I have a prom to get back to. So either leave and start figuring out how to get me fired without demolishing Dallas's reputation, or get on your knees and get my cock ready for your ass. And don't worry about confidentiality; I haven't outed your daughter to anyone but you, and I sincerely doubt you're going to go around telling anyone else."

This was the moment of truth. I was risking my entire career on the premise that she'd choose to protect her daughter and her family's reputation instead of doing the right thing and putting a stop to my sexual predation. I found the few seconds of silence exhilarating, as I awaited the news of my victory.

As expected, I won, although she still tried to manipulate me. Tears beginning to stream down her face (the same crocodile ploy her daughter had attempted at first), she pleaded, "Please! Can't we work something out?"

"We already have," I chuckled, "you've agreed to be a good little fuck-toy just like your daughter, and in return I won't out either of you."

"But if you release the video, you'll out yourself too, and then get fired," she pointed out.

"But I'm not in this video," I rebutted, "how dumb do you think I am? This is your daughter with Markus."

"Oh," she said, crestfallen.

"So I'll ask you only once more: will you get your ass over here and get on your knees?" I demanded, my patience waning.

She began slowly walking towards me, tears still rolling down her face. "If I do this, will you give me the DVD?"

"Sure," I said, "if you do everything I say, like a good slut."

Her face went crimson, and she stared at me for a few seconds before finally falling to her knees. Her hands were shaking as she unbuckled my belt, pulled down my pants and underwear, and then just froze, staring at my nine-inch cock.

I could tell by the surprise on her face that she was impressed. "I know; it's very impressive, isn't it?"

Keeping her bitch persona in place, she shrugged dismissively, "I've seen bigger."

"Good," I countered, "then you'll be able to get the whole thing down your cocksucking throat."

She glared at me once more before opening her perfect lips and taking my cock into her mouth. Very quickly I realized she'd already sucked a lot of cock, since she was doing something with her saliva that I can't explain. It was as if her mouth had actually been transformed into a wet pussy.

I moaned, "You're a great cocksucker, Devon." She ignored my compliment as she continued bobbing back and forth like the experienced MILF slut that she obviously was.

Not wanting to shoot my load yet, I pulled out and ordered, "Get up and bend over my desk, slut."

Her eyes went wide, "You said I only had to blow you!"

"No, I said that if you did

everything

I told you to like a good slut, I'd give you the DVD. I guess you listen just like a high schooler, only hearing whatever you choose to hear. Now do as you're told."

Her glare returned, but she reluctantly stood up and bent over my desk. I was pretty sure that although she was acting all high and mighty on the outside, she was secretly enjoying her submission. Checking whether I was right, I pulled down her skirt to learn whether her cunt was wet. She was wearing pantyhose, so I ripped them open at the crotch.

She turned her head around and snapped, "Those are... or they

were...

twenty-five dollar pantyhose, you asshole."

I threw my own attitude right back at her. "If you wore thigh-highs like a proper slut... or better yet went commando, I wouldn't need to rip open your pantyhose for access, bitch. Now let's see whether your cunt is all wet from thinking about my big cock."

I used my hand to feel her very damp panties. "Your panties are soaked, Devon. Why's that?"

"Not because of you," she threw back weakly, still in denial of the power I was already wielding over her. She was like so many bitches I'd fucked over the years: a dirty slut hiding behind the façade of a pretentious bitch.

"Really?" I asked and countered, "If I didn't cause this swamp, then it must be from watching your daughter sucking cock."

"That's ludicrous," she protested, although with a soft moan as my finger parted her wet pussy lips.

As I slipped a finger inside her pussy, I asked, "So, Devon, have you ever had your back door filled?"

She turned to look at me. Her eyes wide, she responded with her last bit of dignity, "God no, that would be disgusting!"

"Interesting. That's what Dallas said before I trained her to be a perfect ass-slut," I said.

"Please stop talking about my daughter so disrespectfully," she said, her tone angry, yet my finger in her cunt clearly distracting her.