Blackmailed: Cheerleader's Mombysilkstockingslover©
Summary: He forces the Cheerleader's Mom to be his eager ass-slut too.
Note 1: Although not completely necessary, I would recommend you read Blackmailed: Cheerleader's Cherry first as it explains how Principal Stanford blackmails the popular head cheerleader to be 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.
Blackmailed: Cheerleader's Mom
Prom was on a Friday and, as usual, Dallas, the head cheerleader, was in my office taking my cock in her ass. Her training had been complete for over a month. She easily could take all nine inches of my cock up her backdoor, but she loved my cock...what can I say?
Having caught her in a compromising situation a few months ago, I blackmailed her to be my little anal cheerleading slut and rid her of her diva princess personality.
She had dumped her football player boyfriend, as I instructed, and started dating a geek named Markus, the other member of in the compromising situation that got Dallas for me. He was average looking, a genius already accepted to 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. It looked like an eighties teen comedy, the real life version of Revenge of the Nerds.
I saw in Markus a bit of myself young I was a teenager, as I didn't come into my own until college, thus I enjoyed assisting him in his newfound glory.
Dallas had become a perfect little ass slut and her nasty talk always had me revved. Dallas bent over my desk, still in her cheerleader's outfit, my pole buried in her ass, begging, "Harder, Mr. Stanford, fuck your slutty cheerleader's ass."
She had become such an ass slut, that she always needed to be hammered there. She wasn't one who wanted to be made love to, she wanted to be fucked...hard. She was the perfect fuck: drop dead gorgeous, a great cocksucker who loved to swallow (with some training of course), 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 you got past her diva persona and she had the filthiest mouth of any chick I had ever fucked and well...you have the perfect fuck. Knowing she was graduating in under a month was disappointing, as she had really livened up my Friday nights.
She begged, "Fuck me on the floor, sir, I need your cock in me deeper."
We had tried a new position last week that she had found online for maximum anal penetration. It got her off like gangbusters. I pulled out of her ass and she quickly repositioned herself on her back on the floor. Being a cheerleader, Dallas was ridiculously flexible and she put her feet up in the air and behind her head. I am not shitting you, it was the fucking hottest thing ever.
Looking down this human pretzel, I had a perfect look at her gaping asshole. She looked up, her hunger for my cock obvious as she moaned, with her hand somehow going to her pussy, "Please come and fuck my ass, Mr. Stanford, I need to get home for prom soon."
I questioned, "Is prom 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."
"And I want to spend prom with your cum in my ass," she said, her nastiness never getting old.
"Well let's make your prom wish come true," 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 nine inches filled her. "Aaaaaaaaahhhhhh fuuuuuck," she screamed, "it feels so good."
Once deep in her, I began pounding her ass, my body slamming into her forcefully with each hard, deep thrust forward. Her breathing increased as I literally fucked the shit out of her. "Fuck, your ass is so tight," I grunted, knowing I was not going to last long in this position and at this pace.
Her hand frantically rubbed her clit and as she orgasmed from having her ass reamed, her ass muscles tightening around my cock, literally milking my bone. The intensity was too much and as her cum exploded out of one hole, I blasted my cum into another.
Once we both recovered, she weakly got up, her make-up a mess. She looked in 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 made Markus popular enough to become prom king.
I cleaned up and went home to shower before having to be back at school in a couple of hours.
As expected Dallas did win prom queen and looked like a princess in a bright pink gown. I smiled knowing that underneath that innocent looking exterior was an ass-slut who currently had my cum in her ass.
After her prom king and queen dance, which Markus did win by the way, which really showed the power of Dallas's popularity, Dallas introduced me to her mom.
My cock grew instantly, as Mom was an older replica of Dallas. Dallas said, "Mr. Stanford, this is my mom Devon Allen."
I extended my hand, recalling she was a widow, my brain already scheming a way to fuck her, "It is nice to meet you Mrs. Allen."
"It is Devon, Mr. Stanford," she politely replied, her southern accent adding to my fantasy of fucking her.
"Well, if we are on a first name basis then I insist you call me Warren," I smiled back, already working up a blackmailing scheme.
"Well, Warren," she smiled, clearly used to her charm winning over any man, "My Dallas says you completely changed her outlook on school."
"Well," I shrugged nonchalantly, glancing at Dallas who had a devious smile on her face.
"No, I am serious. Dallas was a handful, but since you kept her after school that one day she has been a different person. I can't thank you enough," the naive mother gushed, unaware she was really thanking me for fucking her daughter's ass.
I kept the inside joke between Dallas and me as I replied, "Oh trust me, the pleasure was all mine. Once I got past her diva resistance, she was an eager learner."
Dallas was barely able to hold back from bursting out laughing, but added, "Yes, I was a real quick learner."
I added, "And she doesn't give up until she has mastered the objective."
Dallas couldn't help but laugh as she added, the innuendo dripping as she stressed the word 'coming', "Yes, I just kept coming back again and again."
Mom, oblivious to the innuendo, suggested, "Well, if there is ever anything I can do to thank you, just let me know."
Certain that I was going to fuck her, I smiled, "Actually, now that you mention it. I was hoping for some PR for our school and was hoping you could do a piece about our school."
Her eyes lit up. "What a great idea; what did you have in mind?"
I quickly glanced at Dallas before turning back to her older twin and asked, "Do you have a few minutes now?"
Looking at her daughter, she asked, "Dallas, do you mind?"
Dallas said, "Oh no, go ahead. Markus wants to dance some more and then we are going to the all-nighter. Go with Mr. Stanford, I have learned he is very thorough when he is working on a piece."
The subtlety was gone, and I was sure her mother was going to get the obvious innuendo her daughter had just tossed at her, but instead she hugged her daughter, turned to me and said, her dazzling smile attempting to charm,"Lead the way."
I stammered, surprised I wasn't busted right there, and smoothly said, "This way, ma'am."
I glanced back to Dallas who mouthed, "Are you going to fuck my Mom?"
I just smiled and led my MILF to her impending servitude.
Once in my office, I closed and subtly locked the door before sitting at my desk.
Devon sat demurely across from me, the way I imagined she always did. She asked, innocently, "So what do you with the students on Fridays?"
"Actually, it is only your daughter I work with," I admitted.
"Really?" she asked, "no one else needs the extra help?"
"Oh. I am sure there are many who could use my expertise, but I limit my assistance to a rare few. Actually, truth be told your daughter was the first," I cryptically answered.
"How so?" she asked, confused by my answer.
"I could explain, but I think showing you would be more effective," I said, standing up and going to the DVD player. I pulled out a disk labelled motivation and popped it in the player. Before pressing 'play' I explained, "For some students they work hard because they like learning, others do it because they need the marks for scholarships, others work hard to pad their resumes, yet others need to be motivated to learn."
The pretty MILF said, "Well whatever you did to motivate her has really worked, her marks are in the eighties for the first time since middle school."
I smiled, "Well, I made it clear to her that if she didn't get her marks up her training would end."
"Her training?" she repeated, confused by my word choice.
Pressing 'play', I moved over to the still sitting mother and put my hands on her shoulder. She questioned me. "What are you doing?"
"Just watch," I ordered, massaging her neck as a close-up of her daughter sucking a cock began to play.
"What the hell is going on?" she asked, her usual control gone, attempting to stand.
I held her in place and ordered, "Sit, and I will explain."
She sat back down while ranting, "What is the meaning of this? I will have your job for this!"
I chuckled, "Devon, your daughter is a nasty ass-slut. I caught her blowing Markus and after a lengthy talk I put her in her place."
"In her place? What the hell does that mean?"
"Well, your daughter was a stuck-up, ignorant bitch who thought she ran the school, so I taught her who really runs the school," I explained, cool as a cucumber.
"You had sex with my daughter?" she asked, still shocked by the quick turn of events. It started with her harmlessly flirting with me and was now she was no longer in control. The player was about to get played.
"I have every Friday for months now," I admitted, "but that is not the point."
Surprising me by quickly leaning forward and getting out of my grip, she snapped, "That is exactly the fucking point. I will have you fired."
I chuckled, smugly. "I don't think so."
"Watch me," she threatened, used to her bitchy threat working.
"Get on your knees, slut," I countered.
"What?" she replied, shocked by my demand.
"I think it was a pretty simple demand. Get on your knees," I repeated, before adding for emphasis, "slut."
"How dare you speak to me that way?" she responded, wounded, as if I had just slapped her across the face.
"I don't have all day," I sighed, showing my impatience at her disobedience.
"I am out of here," she said, so angry smoke was almost coming out her ears.
"As you wish," I said, moving out of her way so she could leave, before tossing out there my ace of hearts, with a threat. "But if you do, this video of your daughter goes viral."
She stopped at the door, paused for a brief moment before turning around, and asking with a glare, "Are you blackmailing me?"
"Yes, that seems to be exactly what I am doing," I replied.
Her strong persona seemed to deflate a bit as she shifted from dignified to bargaining. "Maybe we can make a deal."
"I agree," I replied, setting her up perfectly.
"How much?" she asked.
I laughed. "Oh, I don't want your money."
"You don't?" she said, her face again registering surprise.
"Oh no, I want your ass," I revealed.
"What?" she asked, hoping she had heard me wrong.
"Well, I love your daughter's ass, it is amazingly tight, but she will be graduating soon and going away to college so I could use a new ass. Well, you look a lot like your slut daughter, your personality is as bitchy as your slut daughter's used to be before training and I see you are a stuck-up bitch who uses her looks to get what she wants like your slut daughter used to do," I explained, attempting to humiliate her even more.
"How dare you insult my daughter and me like that?" she countered, clearly insulted by my assessment.
I sighed. "We can play this game all night, but I have a prom to get back to. So either leave and go get me fired, or get on her knees and get my cock ready for you."
This was the moment of truth. I had risked my entire career on the assumption that she would protect her daughter and her family image over doing the right thing and stopping me. The few seconds of silence was exhilarating as I awaited the victory of my aggressiveness.
As expected, I won, although she again tried to manipulate me to get her way. Tears beginning to stream down her face, she pleaded, "Please we can work something out."
"We are," I chuckled, "you are going to be a good little fuck-toy like your daughter and in return I won't humiliate you and your daughter."
"But if you release the video you will be fired too," she pointed out.
"This video isn't of me," I pointed out, "how dumb do you think I am? No this is of your daughter and Markus."
"Oh," she said, crestfallen.
"So I will ask you only one more time, get your ass over here and get on your knees," I ordered, my patience waning.
She began to move towards me, tears still rolling down her face. "If I do this you will give me back the DVD?"
"Sure," I said, "if you obey like a good slut."
Her face went crimson as she stared at me for a few seconds before she fell to her knees. Her hands shaking she unbuckled my belt, pulled down my pants and underwear and was staring at my nine inch cock.
I could tell by the surprised look in her face she was impressed. "I know, it is very impressive, isn't it?"
Keeping her bitch persona up, she shrugged casually, "I have seen bigger."
"Good," I countered, "then you will be able to handle it all in your cocksucking mouth."
She glared at me one more time before opening her perfect lips and taking my cock in her mouth. Very quickly I realized she had sucked a lot of cock as she was doing something with her saliva that I couldn't explain. It was like her mouth was a wet pussy.
I moaned, "You are a great cocksucker Mrs. Allen." She ignored my compliment as she continued bobbing back and forth like the experienced MILF slut she was.
Not wanting to shoot my load yet, I pulled out and ordered, "Bend over my desk, slut."
Her eyes went wide, "I thought I just had to blow you?"
"No, I said, if you obeyed like a good slut I would give you back the DVD. You listen like a high schooler, only hearing what you want to hear. Now do as you're told."
Her glare returned, but she reluctantly stood up and bent over my desk. I could tell that even though she was acting all high and mighty, she was enjoying the submission. To check to see if I was right, I pulled down her skirt to see if her cunt was wet like I assumed it would be. She was wearing pantyhose that I ripped at the seams."
She turned and snapped, "Those are twenty-five dollar pantyhose, you asshole."
I pointed out, throwing attitude right back at her. "If you wore stockings like a good slut, I wouldn't have to rip open your pantyhose, bitch. Now let's see if your cunt is all wet thinking about my big cock."
I moved my hand and felt her very damp panties. "Your panties are soaked, Devon. Why is that?"
"Not because of you," she weakly threw back, still in denial of the power I already had over her. She was like so many bitches I had fucked over the years: a dirty slut hid behind the facade of a pretentious bitch.
"Really?" I asked and countered, "If not me, then I guess it is from watching your daughter suck cock."
"That is ludicrous," she protested, with a soft moan as my finger parted her wet pussy lips.
As I slipped a finger inside her pussy, I asked, "So, Mrs. Allen, have you 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 is disgusting."
"That was what your daughter said too, before I trained her to be a perfect ass-slut," I said.
"Please stop talking about my daughter like that," she said, her tone angry, yet my finger in her cunt clearly distracting her.
"Sorry," I shrugged, "I was just trying to point out the obvious similarities. With training she has come to prefer a cock in her ass over her cunt."
"Please stop," she pleaded.
I obliged, pulling my finger from her cunt and going to her virgin ass.
"Please no," she begged.
"That is a rather humorous oxymoron," I quipped, as my finger teased her puckered bud.
"I'll do anything, just please not there," she begged, her strong personality gone.
"Agreed," I said, just long enough for her to think I was agreeing with her before I pushed finger in and added, "Yes, you will do anything to prevent the tape of your slut daughter from going public."
"Aaaaah," she whimpered from the penetration of her ass. "Please, stop."
Ignoring her pleas, I pushed deeper in her ass. "Sweetheart, trust me when I say you want me to do this."
"I would never," she whimpered, grimacing from my finger in her ass.
I laughed, "Well if I don't loosen your ass, the pain when my cock slides inside will be excruciating."
"Please just fuck me?" she begged.
I smiled to myself at the reality that she was begging me to fuck her cunt. I wiggled my finger inside her ass attempting the slow gape process. "Oh don't worry, I plan to fuck you."
"You are such a bastard," she whimpered, through clenched teeth.
"That is what my exes usually tell me too," I smirked, "but they all came back for my cock at one time or another," I replied, thinking of Jessie who called me up just last month, two years after we broke up, just to get laid.
I moved my finger back and warned, "This may sting a bit." I added a second finger and slowly pushed forward. She tightened her ass muscles and I recommended, "I wouldn't do that if I were you. It will only make it worse. Now just relax and trust me."
"Trust you? You are raping me," she snapped.
Deciding to play her game, I pulled my fingers out and said, "I am not raping you. Did I force you into my office?"
I ignored her explanation. "Did I force you to bend over my desk?"
"Well, no, but...."
"But nothing," I snapped. "You choose to bend over my desk like some cheap whore. If you want to blame anyone, blame yourself. You were the one that allowed your daughter to become a bitch that needed to be disciplined. I just did the job you couldn't." I knew this was cold, considering she was a widow and the lack of a father figure was not her fault.
I moved around and sat at my desk, now facing her. Tears were again welling in her eyes.
Sticking to my coldness, I asked, "Weren't you leaving?"
"You will give me the DVD?" she asked, a glimmer of hope in her eyes.
"Oh no, we made a deal for that and you have not fulfilled your end of the bargain," I answered, struggling not to smirk at my own pun.
"I really need the tape," she said, her eyes begging.
"Well, I would love to help, but I am not going to rape you," I answered.
"Sorry," she whispered, avoiding eye contact, before adding, "Please come fuck me."
"Where do you want me to fuck you?" I asked, forcing her to say the words.
"In my ass," she admitted, although her tone implied the opposite...she clearly wanted her pussy filled.
"Beg," I ordered, standing back up, my erect cock directly in front of her.
Seeing my cock seemed to help as a glimmer of lust awoke in her. Her tone was more believable as she begged, "Please, Mr. Stanford, fuck my ass."