Hayden and the Headmaster

Author's Note: AHHH! Happy late Halloween. I hope my scream didn’t scare everyone too badly. But, seriously though, everyone have a good time tonight, get out there, wear some costumes, talk to people, be safe, and responsible, help someone in need if they need it.

This is the second to last section before the FINAL chapter of Frat Pledge. There are currently two endings, one good and one bad, on my Patreon and SubscribeStar, so check those out!

There’s also 4-8 new chapters a month, polls, and we just like to have a good time.

Patreon: https://www.patreon.com/c/BadgerAttack07

Subscribestar:https://subscribestar.adult/badger

CHAPTER 7

Hayden Thompson spent the entire morning worried about his mother. The night before, he had seen her do things he never would have expected her to do as a mother, a woman, or a principal.

To Hayden, she was just doing it to prove a bigger point. She had come all that way to present herself and shut down this fraternity, only to find out that her son was pledging. He couldn’t understand why he wanted to be a part of something that hurt him so much, to the point where even now, as he sat outside Headmaster Bridget Schultz’s office, he was wondering what those guys were up to. Probably having sex and doing drugs.

Finally, a voice called him in from the receptionist’s office, and he opened the door. There was no one there yet; in fact, it would be another 45 minutes before Bridget Schultz entered the office with a file in her hand. She was a short blonde woman with a lot of spunk, who liked to wear tight skirts that showed off her thick thighs and ass, which were, impossible to hide. She always wore her hair in a tight bun and had been a key figure at the university for many years, helping it grow in both student population and graduation rates.

“So, Mr. Thompson, you are here to complain about Delta Phi?”

He was a bit surprised that she didn’t apologize for being 45 minutes late, but at least she was here, unlike his mother. “Yes, ma’am. I’m sorry, I thought my mom would be here, but she must’ve gotten into an accident or something because it’s not like her to be late.”

“Oh, yes. I spoke with Mary Anne on the phone the other day. A very lovely woman and a fellow academic.”

“That’s her. But anyway, the reason I’m here is because I want to talk about some of the hazing and bullying practices going on at the fraternity.” He didn’t know why he was getting nervous, but he was. He took a deep breath and, for the first time in his life, pushed past his discomfort. Yesterday he had almost gotten a girl to like him, and today he could win this. He could beat the fraternity.

“Do you have any proof of this hazing or bullying? These are very severe accusations.”

Her expression had barely shifted. In fact, her eyes hadn’t changed at all; it was only her lips that tilted and shifted with automated movements. He wasn’t expecting a hug, but he certainly wasn’t expecting to be greeted this coldly in the face of his distress.

“Yes, I do have some proof.” He opened his phone and scrolled through his photos until he found the image. “Here, you can see an official post from the fraternity where they photoshopped my mother’s face onto an OnlyFans model just to make fun of me.”

There it was, his winning hand. Everything else, the pushes, the slurs, the insults, had disappeared in the wind. But this picture of his mom posing seductively was his trump card because they had gone one step too far.

The principal grabbed his phone, looking astonished. “My gosh. This is very explicit.”

“I agree. At first, I couldn’t believe it either. They had done some bad stuff before, but this was going too far.”

“Unfortunately, the university has no way of proving that this image is incriminating.”

“Excuse me? I don’t think I heard you right. What do you mean there’s no way of proving this image is incriminating?” He started to get uncharacteristically angry. All his life he had heard that if he stood up for himself, things would finally work out, and now, here he was doing exactly that with no reward.

The principal straightened up, shoulders back, chest forward, and nose held high. “I mean just that. So, unless you have any other proof, I consider this meeting over.”

“You saw it on their Instagram page! I pulled it up for you. They made false pictures of my mother, nude. She’s a school principal; she could lose her job!” He was standing up now, livid, waving his phone around like a sparkler on the Fourth of July.

“Well, if your mother consented to these pictures, then they are theoretically not incriminating.” She checked her files and then closed them again.

“Principal,” Hayden said, fearing the worst. “What do you mean by that?” He was starting to figure out the answer, but he didn’t want to believe it.

“Sit down!” He did as he was told; he had always been weak toward strong women. “Mr. Thompson, if you don’t compose yourself, I’m going to have to file a disciplinary report for your actions today. If you can just calm down, I will explain everything to you.”

He sat down, slumping back in his chair like a worn pillow. The hero had lost; the bullies had won. Now, it was time for their monologue.

“When you first told me about this meeting, I decided to take a personal interest in the case to make sure I had all the information I needed. I visited Delta Phi, determined to get to the bottom of it. After all, as a principal, I am here to protect my students; as a woman, it is my responsibility to protect my female students.”

Hayden was only half-listening as he wondered how they pulled it off. He could justify one woman being turned into a submissive through pure charisma, but two powerful women? There had to be something else going on.

“So, I went, and the boys were all very kind. That is, until I went through some of their cabinets and found a number of illegal drugs, from marijuana all the way up to cocaine. I was on the phone to call your mother and tell her to cancel the whole meeting because I would have to kick them off campus, when one of the boys told me that they only had the drugs for an artistic project they had been working on.”

She pulled out a Polaroid picture of herself next to all the drugs. “They took this picture of me and then proceeded to show me the rest of their art. They even asked me to do some modeling myself.” She was blushing now, the way a teen girl would when talking about a celebrity crush.

She started to lay out more Polaroids one by one: Her standing in her black blouse, green blazer, and khaki pants. Her taking off the blazer. Her removing her khaki pants, then fully nude. One of her squeezing her breasts with her tongue out; one with her trying to put her breast into her mouth while fingering herself. One where she was on the bed with a bunch of dildos around her, and one where she was using one. Finally, one where she was on her knees in between all of the guys, covered in cum. “They are really quite artistic in their approach.”

She looked at them proudly, as if they were wedding photos. Hayden didn’t know what to do, but he wasn’t going to miss this opportunity. “Those are quite beautiful. Do you mind if I take a picture of them?”

“Sure!” she said. “Then they showed me the rest of their collection, where they had plenty of other beautiful women for their photography class.”

Of course they did, thought Hayden. “I get it. They are charismatic, they are cool, and they are confident. But that doesn’t make the picture of my mom any less illegal.”

“Well, it does if your mom’s cool with it.” And just like that, Hayden realized why his headmaster was late.

“I just came from Delta Phi because they needed me for an emergency, and when I got there, who would I find but your mother, Mary Anne Thompson. She was giving fellatio to Marcus for an Artistic project the boys are working on. It was sweet to watch her so involved,” the Principal smiled, “she really is a fantastic educator because she was giving him some very sloppy head which is exactly what Marcus has had me working on.”

Hayden was too stunned to speak.

“Then he asked if we wanted to take some pictures together for a new project he’d been working on about relationships between older women with big boobies, so me and your mom were the perfect choice.” It struck Hayden just how casually she spoke about this as if it were legitimate. She took more polaroids out of her file.

Pictures of his mom, fully naked, and wearing nothing but a cowboy hat. She was bent over a couch with old beer cans scattered around. Her ass bright red and thick. Behind her, the headmaster was wearing her current outfit except the skirt was pulled up past her thick thighs to reveal that she had two clown faced smiles, one on each butt cheek. Her hair was up in pigtails and her massive titties were fully out. A parody of the professional business woman Hayden was staring at.

His mom with her legs wide open and the Headmaster with her head between her legs while she wrapped a USA flag around the back of her head to bring her closer. Each picture was progressively more lewd until finally Marcus showed up between the two girls chugging beer with his dick fully out. Then the final picture had his mom licking recently spewed cum off of Bridget Schultz’s tits. That one was signed “Sorry she was late.”

“It was really quite fulfilling,” Headmaster Schultz said, “I used to paint in college so I was missing a good artistic outlet.” She opened up her blouse, wiped at a little bit of leftover cum and sucked it down. With a dumb smile she said, “And their cum is so yummy!”

Hayden couldn’t help himself, “FUCK!” he yelled loud enough for it to be heard across the quad. The headmaster berated him for it, but he didn’t care as he stared of to the trees. Were these guys so determined to take everything from him that they would destroy the lives of others? What is that they had that would make the women in his life pose for these… pictures. The camera.

Could it be, thought Hayden. Because if that was the case, then maybe his life wasn’t over and he would just need to pay a little visit to the frat.

“Hey, Headmaster,” he said, interrupting her trade, “I’m sorry for my actions. Could you take me to Delta Phi to apologize?”

“Of course,” she said after little consideration. Ryan smiled. He could have his mother back.