Summary: Unprincipled principal forces even the cheerleader’s mom to be his eager slut.
NOTE 1: Though it’s not completely necessary, I suggest you read Blackmail: The Cheerleader’s Cherry first , as it tells the story of how the president of Stanford blackmailed a popular cheerleader into becoming his personal slut.
NOTE 2: As always, I’d like to thank Estragon for his copy-editing expertise, and Larrascas for his plot suggestions.
Note 3: Updated in December 2012 with new epilogue.
Note 4: Updated August 2022 by Tex Beethoven.
Blackmailed: Cheerleaders’ Moms
The dance was on Friday, and as usual, in the late afternoon, cheerleader Dallas was in my office with my cock in her ass. She’s had over a month of training so now she can easily fit my nine inch cock through the back door, she loves my cock… not much, but at least she’s willing to do anything for me. Tell her… what can I say?
A few months ago I caught her in a compromising situation and I blackmailed her into becoming my little anal cheerleading slut and breaking her out of her diva princess persona.
She followed my instructions and left her football player boyfriend and started dating a geek named Marcus, another participant in my mess for Dallas. He has average looks, he’s a genius who got into Harvard and his talent is very, very good. Dallas was so popular that instead of dating geeks going away, she became even more popular, as did Marcus. They’re like the protagonists of 80s teen comedies or the real-life version of Revenge of the Nerds.
I see a reflection of my teenage self in Marcus because I didn’t start being myself until college. So I’m excited to help him find new pride.
Dallas has become a perfect little slut and her dirty talk never fails to turn me on. Dallas was now bent over my desk, still in her cheerleader outfit, my rod buried in her ass, and pleading, “Harder, Mr. Stanford, fuck your slutty cheerleader ass harder.”
She became a slut who always needed to be spanked. She didn’t want to be fucked, she wanted to be fucked in the ass…hard. She is the perfect fucker: very pretty, a great ass that loves to swallow (after we finish training her, of course), her pussy is tight even after being well used, and her perfect ass can take all nine inches of my big dick. Plus, once we get past her diva personality, she is submissive deep inside, has the dirtiest mouth of any girl I’ve ever fucked, and… like I said, she is the perfect fucker. She graduated in less than a month, which was disappointing because she brightened up my Friday nights.
she begged, “Put me on the floor and fuck me Sir, I want your cock deeper!”
Last week we tried a new position she found online that allows for maximum anal penetration, which she was really excited about. I pulled out of her ass and she was soon back on the floor. As a cheerleader, Dallas is so flexible that she keeps her legs in the air and even puts them behind her head. I’m not kidding, it’s the hottest thing ever!
Looking down at my sexy human pretzel, I had a perfect view of her open ass. She looked up at me, her desire for my cock obvious, and she managed to reach her pussy with her hands, moaning, “Please fuck my ass, Mr. Stanford, I have to get home and get ready for prom as soon as possible.”
I asked, “Are you saying prom is more important than me being a slut?”
She immediately apologized, her tone sounding serious, “I’m sorry, sir, nothing is more important than making you happy.”
“I’m just kidding,” I said, smiling, “You only get a chance to go to the ball once in your life. However, I would like a favor in return.”
“Of course! Name it.”
Well, I saw your mom’s name on the list of volunteer guardians, so I wanted you to introduce me to her.
“Of course I can do that. But why?”
“Because I want to fuck her.”
“What? I can’t guarantee that!”
“No, no, I will seduce you, just introduce us.”
“Okay, sure. That sounds fun! But now I want to help.”
“Which one?”
“I want your cum in my ass for my dance party,” she said, her shit never lacking in material.
“Okay, so now let’s fulfill your prom wish,” I bent down to satisfy her in the most satisfactory way possible.
My cock filled her gaping ass with ease and she let out a glass shattering scream as I filled her with all nine inches of cock. “Ahhhhhhhhhhhhhhhhhh” she cried, “this feels so good!”
Once I was deep inside her I started pounding her ass, slamming my body into it with each hard, deep thrust. Her breath hitched as I really fucked the shit out of her. “Fuck, your ass is so tight,” I grunted, knowing I couldn’t last much longer in this position and at this pace.
She rubbed her clit hard, her anal muscles tightened around my cock and started milking my boner as she reached climax from the anal reaming. The intensity was too much for me and as soon as her cum spilled out of one of her holes, I shot my load into the other.
When we all recovered, she stood up limping, her makeup a complete mess. She looked in her compact mirror and joked, “I look exactly like I feel.”
“Until next week,” I said as I got dressed.
“I’ll be here,” she promised enthusiastically before heading off to prepare for prom, where she will undoubtedly win the title of prom queen. The only question is whether she makes Marcus popular enough to become prom king.
I clean up, go home and shower, and in a few hours I have to go back to school.
……
As expected, Dallas was the prom queen and she looked like a princess in a bright pink gown. I smiled, knowing that underneath that innocent exterior was a butt slut who still had my cum in her ass from this afternoon.
After the Prom King and Queen prom (by the way, Marcus was the king) which really showcased Dallas’ popularity, Dallas pulled me aside and introduced me to his mom.
My cock immediately swelled because her mom looked just like Dallas. In other words, her mom doesn’t look a day older than her daughter, and they could easily be mistaken for identical twins. Dallas said formally: “Mr. Stanford, it’s my pleasure to introduce you to your mother, Devin Allen.”
I approached her, remembering she was a widow, and my mind was already thinking about how to fuck her, “Nice to meet you, Mrs. Allen.”
“Please call me Devon, Mr. Stanford,” he replied politely, his Texas accent reinforcing my fantasy of fucking him.
“Well, if you want us to be on a first-name basis, I’d be happy if you called me Warren.” I replied with a smile, already plotting my blackmail scheme.
“Well, Warren,” she smiled, obviously accustomed to using her charm to win over any man (her beauty had always given her a big head start), “Dallas tells me you’ve changed completely. What does he think of school.
“Uh…” I shrugged casually and looked over at Dallas who had a sly smile on his face.
“No, I’m serious. Dallas is definitely a tough person, but ever since you kept her after school that day a few months ago she’s become a completely different person. I can’t thank you enough, she was clueless.”
I replied, “Oh, believe me, I’m glad. Once I got over her diva resistance, she became very eager to learn.”
Dallas could hardly hold back her laughter, but she said with a straight face: “Yes, President Stanford, thanks to you, I became an enthusiastic student!”
I added, “She never backed down until all her goals were achieved.”
This time, Dallas couldn’t stop herself from laughing, and as she stressed the word “come,” she said in her natural style, “Yeah, I just come every now and then .”
Mother, unaware of the hint, suggested, “Well, Warren, if there is anything I can do to thank you, please let me know.”
I was sure I was going to fuck her tonight, I smiled and said, “Actually, now that you mention it, I was hoping you could do some PR for the school. Maybe you could write an article about our various accomplishments?”
Her eyes lit up. “What a great idea! Do you have any ideas?”
I took a look at Dallas, then turned to his twin’s mother and asked, “Do you have a few minutes now?”
He looked at his daughter and asked, “Dallas, do you mind?”
Dallas said, “Oh, no, go ahead. Marcus wants to dance a little more, and then we’ll spend the night, and I’ll be home tomorrow morning. So, keep talking to us about those PR things.” Anyway, the Stanford principal; I found him very serious every time he created a piece.
Does she mean that whenever I’m dealing with a piece of…butt? Well, the subtlety is lost, especially since she just made it clear that she’ll wake up next to Marcus tomorrow morning, probably in the hotel room. I’m pretty sure her mother also understood the clear hint her daughter gave her about me, but she didn’t say anything maternal or reserved, just hugged her daughter, then turned to me and said, the brightest smile of the people being very successful in attracting me to her, “Lead the way, Warren.”
I swallowed, surprised I wasn’t caught red-handed, and said calmly, “This way, Devin.”
I looked at Dallas and he said, “Good luck fucking my mom!”
I just smiled and led my mom to her upcoming bond.
When we reached my office, I quietly closed the door and sat down at my desk.
Devin sat down hesitantly at the desk across from me, just as I had expected him to. He asked innocently: “Then what are you doing with the students on Friday afternoon?”
“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 guidance to a very few. To be honest, your daughter is my first and only private student to date.”
“Why is that?” she asked, interested at my lack of answer.
“I could explain it, but I think it would be more informative to show you something,” I said, standing up and walking towards my DVD player. I selected a disc labeled Motivation #14 and placed it in the player. Before pressing “Play,” I explained, “There are many different questions that can motivate students to excel in their studies. Some students will study hard simply because they enjoy studying, while others will study hard because they need high grades to succeed.
The beautiful MILF said, “Well, whatever you did to motivate Dallas definitely worked. His GPA is in the eighties for the first time since middle school.”
I smiled and said, “Well, I made it clear to her from the beginning. If her results don’t improve and she can’t continue, I will stop her training.”
“His training?” she repeated, surprised by my choice of words.
Pressing play, I stood up beside where my mother was sitting and put my hand on the back of her neck. She asked: “What are you doing?”
“Just watch and you’ll see,” I commanded, massaging her neck as I began showing close-ups of her daughter sucking cock. From the camera angle, it’s clear that Dallas is the one sucking, but the cock could be anyone’s.
“What’s going on?” she asked, her usual self-control gone, and she tried to stand up.
I held him and ordered: “Sit down first and I will explain.”
She sat back and roared: “What does that mean? I’m going to take your job!”
I laughed and said, “Devin, your daughter is a bad slut and she has been for a while… long before I came into her life. She was found having sex with Marcus in the janitor’s closet, so finally, she got caught .
“Instead of that? What’s the point of that sexy nonsense?”
“Well, your daughter is an arrogant, ignorant bitch who thinks she runs the school, so I’m teaching her a lesson about who really runs the school,” I explained calmly.
“In other words, you admit that you had sex with my daughter?” she asked, shocked by the sudden turn of events. We used our pinkies to flirt with me in the beginning, but now she has no control over me at all. The player has been played.
“Yes, and more than once. We had sex every Friday afternoon for months,” I admitted, “but that’s not the point.”
To my surprise, she quickly leaned forward, broke free from my grip, and said, “I don’t know what you mean, but what I mean is, I’ll fire you right now, you bastard!”
I smiled triumphantly. “I don’t think so.”
“Look at me,” he threatened, his vicious threats accustomed to always succeeding.
“Get on your knees, bitch,” I replied.
“What?” he replied, shocked.
“I think this is a simple request. Get on your knees…” I repeated, then added for emphasis, “…bitch.”
“How dare you talk to me like that ?” She became angry, hurt but still mischievous, as if I had slapped her in public.
“Get on your knees. I don’t have all night.” I sighed, showing my impatience at her disobedience.
“I’m leaving,” she said, so angry that smoke nearly came out of her ears.
“As you wish,” I said, moving out of his way so he could leave, and then dismissing my Ace of Spades threat. “But if you do, this video of your daughter will go viral.”
She stopped at the door, paused, turned around and glared: “Are you blackmailing me?”
“Yeah, I’d say that’s a perfect description of what I do,” I replied.
Her strong character seems to weaken a little as she begins to bargain with the shyster. “Maybe we can make a deal.”
“Sounds good to me,” I replied, preparing myself fully for him.
“Okay, how much?” he asked.
I laughed. “Oh, I don’t want your money.”
“Don’t you think so?” she said, another look of surprise coming across her face.
“No, I want your ass,” I revealed.
“What?” she asked, hoping she had heard correctly.
“Well, I love fucking your daughter’s ass; it’s so sexy and tight, but she’s graduating soon and going to Harvard with Marcus, so I need a new ass. It looks a lot like you, slut lady, your character is just as evil. It was before I started training your slut lady, I can tell you’re a stuck up bitch who uses her looks to get what she wants, just like your slut lady, women and children are the same as before,” I explained, humiliating her even more.
“How dare you insult me and my daughter like that?” she replied, completely hurt by my comment.
I sighed. “We could play this game all night, but I have to get back. So, either get out and start thinking of ways to get me fired without ruining Dallas’ reputation, or get on your knees and get your cock ready for this up your ass.
This is a crucial moment. I have put my entire career at risk if she chose to protect her daughter and her family’s reputation rather than do the right thing and stop my sexual harassment. I found these few seconds of silence thrilling as I waited for news of my victory.
As expected, I won, although she still tried to trick me. Tears streamed down her face (her daughter had used the same alligator tactic initially) and she begged, “Please! Can’t we think of something?”
“We have agreed,” I said, laughing, “that you have agreed to become a nice little sex toy, just like your daughter, and in return I will not spare either of you.”
“But if you posted the video, you would be outed and fired,” she explained.
“But I’m not in this video,” I protested, “How stupid do you think I am? This is your and Marcus’ daughter.”
“Oh,” she said sadly.
“So I’ll just ask you one more time: can you come over here and get down on your knees?” I asked, my patience running out.
She started to walk slowly toward me, tears streaming down her face. “If I do this, can you give me the DVD?”
“Sure,” I said, “if you do as I say, like a good slut.”
Her face turned red and she stared at me for a few seconds before finally dropping to her knees. Her hands were shaking as she undid my belt and removed my pants and underwear, then stood still, staring at my nine-inch cock.
I could tell by the surprised look on her face that she was touched. “I know, it’s impressive, isn’t it?”
She maintained her bitchy image and said dismissively, “I’ve seen bigger ones.”
“Well,” I replied, “then you can swallow the whole thing.”
She looked at me again, then opened her lips and took my cock in her mouth. Soon I realized that she had sucked a lot of cock because she was doing something with her saliva that I couldn’t explain. It seemed as if her mouth had literally turned into a wet pussy.
I groaned, “You’re such an asshole, Devin.” She ignored my compliment and continued to rock back and forth like a seasoned MILF slut.
I didn’t want to shoot just yet, so I pulled away and ordered, “Get up and sit on my desk, bitch.”
His eyes widened, “You said I just wanted to blow you away!”
“No, I said if you do what I tell you and like a good slut, I will give you the DVD. I think you listen like a high school student and only hear what you want to hear. Now do as you please as you are told.”
She glared at me again, but reluctantly stood up and bent over my desk. I am pretty sure that although she appears arrogant and domineering, secretly she enjoys being submissive. To check if I was right, I pulled her skirt down to see if her pussy was wet. She was wearing pantyhose so I tore it right at the crotch.
She turned around and said, “Those are…or were … twenty-five dollar tights, bastard.”
I hit back at her with my attitude. “If you wear stockings like a real slut…or better yet go commando, I don’t have to rip your tights off to get in, bitch. Now let’s see if your pussy gets wet from thinking about my big cock”.
I touched her wet panties with my hands. “Your panties are wet, Devin. Why is that?”
“Not because of you,” she replied weakly, still denying the power I had over her. She was just like the bitches I had fucked over the past few years: a dirty slut hiding behind a showy exterior.
“Really?” I asked, replying, “If I didn’t create this swamp, it must have been from watching your daughter suck a dick.”
“That’s ridiculous,” she protested, although a soft moan escaped her mouth when my fingers parted her wet labia.
As I fingered her pussy, I asked, “So, Devin, is your ass filled?”
He turned and looked at me. He widened his eyes and replied with the last shreds of his dignity: “Oh my god, no, that’s disgusting!”
“Interesting. That’s what Dallas said before I trained her to be a perfect slut,” I said.
“Please stop talking so disrespectfully about my daughter,” she said, her tone angry but clearly distracted by the presence of my fingers in her pussy.
