Oral Advocacy Ch. 10: The Principal

"Come in," Jane said through the closed door to her office moments after Kate knocked. It was July 9, 2002, only three days before Kate would learn whether she would become a partner at her law firm. Until a few minutes ago, she was sure she had it in the bag. She'd won her first two jury trials and had successfully resolved her first client's case, to that point that she'd started to bring in teachers as new clients. Most importantly, she'd opened a new line of business with an insurance company, something the senior partners loved. Kate had always been an extremely hard worker, a skilled legal writer, and a dedicated member of the firm. She'd known for months that she was a lock to make partner.

Until now. She'd received a message from Jane's assistant saying she needed to drop everything and come to Jane's office to discuss the recent matter she'd handled for Becky Tapper, Kate's first client. Given Jane's earlier questions about why the witnesses against Becky had recanted, and how exactly Kate had gotten a student to give her inside information, Kate knew Jane was suspicious of her.

Kate smiled at the thought as she entered Jane's office. Being with Henry and James and two strangers at the same time continued to excite her. As did getting to thank Becky by banging her husband and then having a threesome with her and Samantha. Knowing that it put her over the top on her yearslong quest to become a partner just made it all the better. But her smile quickly faded as she closed the door behind her, knowing in her gut that something wasn't right.

"Hi, Ms. Rogers," Kate said. "Your assistant said you needed to see me right away. Is there something I can help you with?"

Jane gestured for her to sit across from her large desk. Jane was one of the firm's senior partners and, although they made decisions as a group, the real power in the office. She brought in more business than the others and, as a result, got to make most of the decisions. "As you know I conducted a review of your handling of Ms. Tapper's matter," Jane said. "Admittedly, I had a few concerns about why two witnesses would suddenly change their stories and why this student Henry was so eager to help you and give inside information to an attorney who, as it turns out, got herself banned from the school premises."

"That was just because the principal got tired of me," Kate said. "He didn't like how aggressively I represented Ms. Tapper. I didn't do anything wrong."

"I understand," Jane said. "I spoke with him, and we'll get to that in a minute. But I also spoke with Mr. Nevil, James, and Henry. Everything checked out, so you're good there. That brings me to the last thing we need to discuss. I talked to the principal, Flanagan, and while I agree he's a bit out there, he's convinced you did something inappropriate to get all three of these witnesses to back Ms. Tapper."

"Did he say why he thinks that? Or what he thinks I did?" Kate asked, her unease growing.

"Flanagan claims he reviewed the surveillance video from the school and found two concerning videos. One supposedly shows you in the school with the student James, including going into the newspaper office and a classroom."

"That's from when I met with him to go over his allegations against Ms. Tapper," Kate said, hoping the video didn't show the inside of either room. "I wanted to see if he really could have seen what he said he witnessed. It was after I had been banned from the building, but I thought it was worth it. Is that a problem?"

"No, of course not," Jane said. "As long as the video doesn't show anything improper. Of course, if it does, it would be hard to see how you'll get promoted on Friday."

"I completely understand," Kate said. "I'm just annoyed that my abilities are being questioned, like I'm only a good lawyer because I'm attractive."

"Trust me, I get it," Jane said. "Ask any of the older men around here how I got to be a partner. They'll tell you there are two reasons." She pointed to her enormous breasts which, Kate had to admit, were great assets for Jane. "They all think I slept my way to the top. I don't want anyone thinking that about you, which is why I'm doing this review. Inevitably one of these guys is going to make a comment, and I want to be able to shove it right up his ass."

"I appreciate that," Kate said. "And it's terrible they think that about you. You're such a great attorney. Although if I'm being completely honest, you're quite attractive too. Nothing wrong with being both, right?"

"Thank you," Jane said. "Oh, I almost forgot. Flanagan said he also has a video of you in the parking lot of the school with Henry. He didn't say more than that. I'm going to the school on Friday to watch both videos and put this to bed."

Kate forced a smile and fought the urge to panic. Damn it, she thought. Why did I have to suck Henry's dick in the back seat of my car? What would the cameras show? How am I going to explain pulling him into the back seat--especially if it shows my head bobbing up and down? "Well, again, I appreciate it, Ms. Rogers," Kate said. "Let me know if there's anything you need from me, and I look forward to this all being over soon."

"Friday at 9 a.m.," Jane said. "Everything will be resolved then, one way or the other. I know which way you'd prefer." The way she said it concerned Kate, like Jane knew more than she was letting on. Has she seen the video already? Am I going to get fired? How does she know? These thoughts and more raced through Kate's head as she returned to her office.

This can't be happening, she thought as she sat down at her desk. A few weeks ago, she'd tried to tell Jason, her best friend at the firm, how she really felt about him, only to have it blow up in her face when she'd learned that he was at a hotel with Sam and Matt. Since then, Jason had avoided her like the plague, turning and walking away as soon as he saw her. They only guy she truly cared about was apparently sleeping with Sam, Kate's sometime lover and the girlfriend of Kate's former lover Matt.

And now this. Jane would see the video and have no choice but to fire Kate, blowing a witness being something that wasn't yet accepted. Then it would all come out--sleeping with the other witness James, banging Henry repeatedly, getting Sam to sleep with Mr. Nevil. It's all over because I got careless and did it one time in the parking lot without thinking about the damn cameras, Kate thought. God, if only that video could disappear. Well, in for a dime, in for a dollar, she thought as she grabbed her purse and hurried down the hall.

Seeing Jason ahead of her, she called out to him, but he pretended he didn't hear and bolted. God, he's so ridiculous, she said to herself, but I don't have time for this today. She told her assistant she was taking the afternoon off and drove straight to Trinity High School. Arriving about 20 minutes later, she headed inside, finding the place nearly deserted given that it was July. Stopping in the restroom, she saw she looked good--tight navy skirt, powder blue button-down top, and navy blazer. Well, here goes nothing, she thought as she headed for the principal's office.

There was no one inside, but the door was open. Henry's job had ended a few weeks earlier and it looked like everyone else who worked in the office was gone too. Creeping past the receptionist's desk and down the hallway to Flanagan's office, she was pleased to see his light on. "Dr. Flanagan?" she said from the doorway. "Can I speak with you a minute?"

"Ms. Harris," he said with evident surprise as he looked up from his desk. "I don't think that's a good idea. How'd you get back here anyway?"

"No one was up front," Kate said. "Please, just a moment of your time."

"I take it you heard about the video," Flanagan said. "How dare you? You made me look like a fool in front of those lawyers."

"I'm sorry about that," Kate said. "I take it you told them Ms. Tapper slept with Matt and that you had testimony to back it up?"

"Yes, and I did. At least until you came along," Flanagan said. "I looked like a complete idiot when James and Bob Nevil changed their stories. All that time and money wasted. And worst of all, I have to keep Becky Tapper on the faculty. I know it's all true. She slept with a student and got away with it."

"He was 18," Kate said.

"That's not the point," Flanagan said, letting Kate know she was right. "She can't behave that way. And to do that with a student, right here in the school building, and get away with it. And now I just have to sit here and take it? I don't think so. At least your boss will see the video of you and Henry in the parking lot and you'll be a goner."

"She hasn't seen it yet?" Kate asked.

"No, not yet," Flanagan said. "Friday morning at nine. By that afternoon, you'll be unemployed." Kate was relieved to know Jane hadn't seen the video, but knew she had to act fast to make sure it went away. Flanagan was tall and athletic, probably 6'2" and at least 100 pounds heavier than Kate's petite 5'2," 112-pound body. She'd always fantasized about being with a guy that much bigger than her and, sitting in his office, knew this was her chance. What the hell, she thought. Might as well do some oral advocacy for myself.

"I'm sorry I was such a bad girl, Principal Flanagan," Kate said softly.

"Excuse me?" he asked.

"I'm sorry I've been such a bad girl," Kate said again. "Do you still spank students who misbehave?"

"Um, no, we don't really, um, we don't do that very often these days," he said, shifting in his seat.

"That's a shame," Kate said. "Because I've been very bad, and I think I need discipline only a principal can provide."

"Uh, well, I see," Flanagan said, standing up from his chair. "You know, now that I think about it, I still recall how to do it."

"And how is that?" Kate asked.

"Spanking, handcuffs, bending you over my desk--all sorts of options," Flanagan said.

"Good," Kate said as she stood up and walked around the desk and stood inches from him. "I think I'll need all three. I've been very bad lately."

"Yes, you have," Flanagan said as he opened a drawer and pulled out a pair of handcuffs. "It's good you came to the principal's office." Just as Kate started to smile, Flanagan grabbed her and bent her over his desk, pressing his left hand pressed against her back. He ordered her to put her hands behind her back and quickly cuffed her. Kate felt his erection press against her ass as he leaned forward and whispered into her ear, "You've been a very bad girl, haven't you?"

"Yes, Principal Flanagan," Kate whimpered, getting wet from feeling his hard cock pressing into her.

"What do you need?" he asked.

"I need your cock," Kate replied. Flanagan pulled her up and pushed her onto her knees. He quickly unbuckled his belt and dropped his pants to his ankles as Kate waited with anticipation. She gasped when he pulled his boxers down. His cock was huge, almost as big as Jason's. "Oh my God, I didn't expect you to be so..."

Before she could finish, he stuck his eight-inch cock into her mouth and all the way into her throat. His girth was impressive, certainly thicker than any cock Kate had sucked before. She gagged a little and her mouth started to overflow with saliva as he held his massive dick inside her throat for a good ten seconds. He pulled it out and quickly shoved it back in, pressing a little deeper and making Kate gag slightly again. His left hand was on the back of her head and with his right he pushed her hair behind her ear. "Look at me," he ordered. "I want to watch you take my huge cock."

Kate looked up at him, overwhelmed by his length and thickness. He pushed into her throat again, holding his cock inside as she struggled to catch her breath. Eventually he pulled out and said, "What do you want?"

"I want your cock, Principal Flanagan," Kate said. He pushed inside again and again, each time asking what she wanted. Every time Kate asked for more as her eyes watered and saliva ran down her chin. After about ten times, when Flanagan again asked what she wanted, Kate said, "I want you to fuck my face."

Flanagan smiled and started thrusting into her mouth vigorously, showing no mercy as he slid his thick, eight-inch cock into her over and over. Kate struggled to keep her eyes on his as he powerfully and roughly pressed into her throat again and again. Saliva spilled out of her mouth every time he withdrew to briefly let her catch her breath. Whenever she looked down, he ordered her to look up and then shoved himself even deeper into her throat, his left hand holding her head steady as he continued thrusting.

Suddenly, Flanagan withdrew and pulled Kate to her feet. "You weren't expecting that, were you?"

"No," she said. "I didn't think you'd be so big." He bent her over his desk again and put his dick in her handcuffed hands. Kate began to stroke him as he hiked up her skirt and put his fingers inside her panties. She struggled to stay on her feet, the desk being a little too tall for her petite frame.

"You liked that, didn't you?" Flanagan asked as he rubbed her soaking wet pussy.

"I loved it," Kate moaned. "Don't stop."

"I guess you need more discipline," Flanagan said. He yanked her panties to her ankles and pulled them off. He roughly spread her legs and squeezed her tight ass. "Yeah, you need it bad." He slapped her ass and Kate squealed with surprise. He slapped her harder, fingering her with one hand and spanking her with the other. He tried to stick his cock in her, but Kate was too short to keep her feet on the floor while she was bent over his desk. Flanagan lifted her onto the desk, with her skirt pulled up above her waist and her legs spread wide. Her cuffed hands nestled in the small of her back and his cock poised at the entrance to her throbbing, wet pussy, he said, "This is what you get for being such a bad girl."

With that he penetrated her, filling Kate like never before. He was so hard and thick and long. "Punish me, Principal," she moaned. "I've been so bad." Flanagan didn't ease into it, obviously ready to cum from being inside her mouth so long. Kate spread her legs further as he railed her. He was incredibly forceful and started hitting her G-spot, making Kate cry out and wetten further. After a few thrusts it started to really good, Kate thought as she started to lose control. His massive cock pounded into her and soon she started yelling and begging for more.

Flanagan pulled her off the desk and onto a couch in his office. Her face on the cushion, he entered her from behind with one leg on the floor and one kneeling on the couch. Kate's tiny body shook as she whimpered, completely at his mercy as he drilled her harder and harder, giving Kate a fucking like she'd never experienced. God, what Matt could do with a cock like this, she thought.

He pulled out and flipped her over, pressing her thighs to her chest. Her legs open wide, Flanagan penetrated her gaping pussy, driving as deeply into her as he could. Flanagan gave her the most intense fucking she'd ever experienced, his massive cock stretching her out like no one ever had. Just as she was about to cum, Flanagan thrust into her and let out a loud groan. He stopped and held himself inside her, the look on his face letting Kate know he was still emptying his balls. Then he thrust a few more times, softer than before, before withdrawing.

Kate stared at him with a desperate look in her eyes. She was so close and needed to climax so badly. His cum leaked out of her pussy as, to Kate's astonishment, he put his pants back on and helped her off the couch. "You've never had a fucking quite like that, have you?" he asked.

"No," Kate said, a little delirious from the experience. "That was so intense. Thank you, Principal Flanagan. But aren't you going to finish me off?"

"No, I have a meeting to get to," Flanagan said. "Here, let me undo those and I'll show you out. Mind if I keep these?" He picked her panties up off the floor and put them in his desk drawer. Returning with a key, he unlocked Kate's handcuffs and handed her some tissues. "Here, you can use this to clean up."

Astonished, Kate cleaned herself up and pulled her skirt back down, adjusting her shirt and jacket as he gestured toward the door. "You're really not going to return the favor?" she asked. "You're not going to get me off?"

"Like I said, I have a meeting," Flanagan said. "Besides, I just gave you the fuck of your life, Ms. Harris. And of course, as promised, you can see the video." With that he got onto his computer and pulled up a video file, letting Kate see herself climb into a car with Henry and start sucking his dick. Flanagan closed the file. "I'll delete that one and show your boss this one instead." He opened another file, from the next day, which just showed Kate meeting with Henry in the parking lot. "I'll play it up like I think it's a big deal, but of course this one doesn't show anything."

"Thanks," Kate said hesitantly. She couldn't believe he was going to leave her hanging like this. "You're really not going to finish me off? I was this close."

"Don't act like you didn't get what you wanted, counselor," he replied. "We both know that was the best pounding you've ever taken, both in your mouth and your pussy. But you need to stay focused. You lawyers like to negotiate, right? What do you want for the video?"

"You're right about that being a great fucking. And about us liking to negotiate," Kate said enthusiastically, an idea popping into her head. "Principal Flanagan, do you know who Samantha Gentry is?"

"Of course," he said. "All the students used to talk about her. The hottest woman in town, right? I saw her at a couple dances I chaperoned and I have to say, I agree. Why do you ask?"

"How'd you like to nail her too?" Kate said. "As a gesture of appreciation, both for giving me the fuck of my life and for getting rid of that video?"

"I knew you liked it," he said. "Of course, I'll fuck Samantha Gentry."

"Thursday night, at my house?" Kate asked. Flanagan smiled broadly and readily agreed to meet Kate and Sam two nights later. Kate jotted down her address and kissed him on the cheek. "Don't be late."

"I won't," he said. "But I will need one more thing?"

"What's that?" Kate said flirtatiously. "Want me to suck your dick again?"

"Well, yes, of course," he replied. "But I actually want one hour with Becky."

"Becky Tapper?" Kate asked.

"Yes, I've always wanted her," he said. "I only think it's fair. She's the one who started all this by having an affair with a student here in my school. She couldn't do that with one of her colleagues? I get it if her husband couldn't keep it up, but there are better options than a student. She's so hot I wouldn't have had any trouble keeping her satisfied."

"I'll talk to her and see if she'll agree," Kate said. In the parking lot she called Sam and told her everything that had just happened. "I need your help. I can't risk this guy ruining everything for me on Friday, so I want to make sure he follows through. I know just what to do." She told Sam her plan, to which Sam eagerly agreed.

"I'll leave work a little early on Thursday and drive down. I love a big cock. I can take Friday off. Then when you make partner, we can go out and celebrate," Sam said.

"There's a happy hour Friday afternoon. Everyone leaves the office early, around 4:00, to celebrate with the new partners," Kate said.

"A party with a bunch of corporate lawyers sounds great," Sam said sarcastically. "Although on second thought, I assume Jason will be there, so count me in."

"Yes, about that," Kate said. "What were you doing with him at a hotel?"

"Sorry, Kate, I have to go," Sam said. "See you Thursday." She hung up before Kate could respond. Sam and Jason? Kate thought. I can't believe this is happening. Why is he doing this to me? That's an easy one, Kate, she said to herself. Sam is gorgeous and Jason isn't getting any. But why is she doing this to me, Kate thought as she got into her car and drove to Becky's house.