Oral Advocacy Ch. 10: The Principal

Leaving the door open, she removed her panties and crawled inside. Crouching on the floor of his thankfully roomy back seat, Sam began to suck Jason's dick as he reclined with his upper back against the door on the opposite side. By now she had grown addicted to his 8.5-inch cock and couldn't get enough of it. She worked her way up and down the top half as she held the bottom half in her smooth hand. Stopping every so often to stroke him from end-to-end, Sam slowly and deliberately sucked him until he was good and hard.

Sam lifted her head and, while stroking him lightly, said, "I want you to make me orgasm one more time." She turned around and put her left knee on the car seat and her right foot on the floor. Facing away from Jason, she lowered herself onto his cock and began to ride him. Her engorged clit rubbed against his huge dick as she moved up and down on his shaft. Using her hand, she started to rub her clit and quickly climaxed, yelling loudly as she did. Sam started riding him harder, taking him as deep as she could until she heard Jason start to grunt.

Knowing he was about to cum, Sam pulled herself off him and began sucking and stroking his dick again. She loved tasting herself on him as he grunted and his muscles and balls tightened. Moments later the taste of his cum mixed with her juices in her mouth as Jason blew a massive load into her mouth. Sam held her lips tightly on his cock as he finished shooting into her, then sucked him a few more times before lifting her head and swallowing as she looked into his eyes.

"I hope that helps you patch things up with your fiancé," Sam said. "It seems like the two of you have a bright future ahead of you."

"I know you don't believe me," Jason said as he pulled his pants up and then started to button his shirt. "But I do love Carrie, and I'm going to fight for our relationship."

"I admire your loyalty," Sam said. "I really do. I'm not trying to mess things up for you. I know it's none of my business, but you know I think Carrie's not the one for you. I'll leave it at that. And thank you for letting me have that incredible cock of yours. I know I'll be thinking about it for the rest of my life."

"Thanks, Sam," Jason said as he finished buttoning his shirt and got out of the car. "For everything. Man, I can't believe I got to hook up with someone so hot."

"We can think about each other whenever we get horny," Sam said flirtatiously. "Good luck with everything. I'll talk to Kate. I don't want you two to not be friends because of me." She kissed him on the cheek and hugged him before starting to walk to the stairs as he got into his car. As he passed her on his way out, he stopped and held up her panties. "Keep them," Sam said, smiling as Jason rolled up his window and drove away.

When she got back to the bar, Kate was still on the patio outside, now at least half drunk. She and her few remaining colleagues, all men, were telling stories about their cases. As soon as Kate noticed her, she stopped talking and said, "Well, if it isn't Samantha Gentry, the hottest woman on the planet. What do you think guys, isn't she gorgeous?"

They all mumbled their assent, obviously taken with Sam by the way they stared at her but not sure of how they were supposed to respond. "It's good to see you too, Kate. Congratulations on the promotion. It sounds like you've had quite the day."

"Yes, thanks to you," Kate slurred. "Guys, Samantha here is available if anyone wants to sleep with her. Right, Samantha? Any takers? You can just walk back to the office and she'll..."

"Kate, that's enough," Sam said sternly. "I think it's time for me to get you home before you embarrass yourself."

"Embarrass myself?" Kate said. She started to laugh, after a while adding, "You, of all people, are worried I'll embarrass myself?"

"Gentlemen, it was nice to meet you," Sam said. "I'm sorry we can't stay longer, but I need to get Kate home. Settle her tab and she'll pay you back on Monday. Kate, get up and come with me." Kate sat still so Sam added, "Now, Kate," in a stern voice and lifted her under her shoulders onto her feet. Sam was amazed at how tiny Kate was.

Wrapping her arm around Kate's back and under her shoulder, Sam walked Kate to the door as she protested leaving. They walked to the parking garage Sam had just been in but this time went to her car, the whole time Kate babbling on about how she was fine to drive and wasn't really drunk. When they got to her car, Sam dumped Kate into the back seat and tried to close the door. Kate stopped her, insisting she could drive home.

"Get in the car, Kate, I'm driving you home," Sam said. "You can get your car tomorrow." She pushed Kate's legs inside and slammed the door, quickly jumping in the front seat and starting the engine before Kate could react.

As she backed out and started driving, Kate said, "You're a real bitch, you know that?"

"I know," Sam said. "I slept with Mr. Nevil for you, and his wife. And with Tyler and Becky and Flanagan, and, of course, with you. I also let you sleep with my boyfriend for a year and a half because you can't find your own man, but yeah, I'm a real bitch."

"You know what I mean," Kate said. "I'm talking about the one you didn't mention. How could you, Sam?"

"Come on, Kate, the poor guy hasn't gotten laid in months!" Sam yelled. "And he has that incredible cock. Matt always fantasized about seeing me get fucked by a huge dick, so I did it for him. And myself, of course. In fact, I just sucked and fucked him in the back seat of his car after you had your little fight. Since you weren't going to do anything about it, I did."

"Fuck you, Sam!" Kate screamed from the backseat as they drove to her house. "You know I like him!"

"He's not your boyfriend," Sam yelled back. "He doesn't know how you feel because you're too big of a pussy to tell him!"

"So, you slept with him and let his fiancé think it was me?" Kate said incredulously.

"I did what needed to be done," Sam said. They drove on in silence, arriving at Kate's house a few minutes later. Sam helped her inside and got her out of her clothes. Kate looked incredible but Sam decided to let it go, instead helping Kate into bed, where she promptly passed out. Before she left, she looked in Kate's phone and got Jason's address, just in case.

On Monday Kate went to work as a partner for the first time ever. She saw her new office, with a fresh nameplate that said, "Kate Harris -- Principal." Just like she'd always dreamed. After two long meetings and endless paperwork, she was surprised at how quickly 6:00 p.m. rolled around. She stopped by Jason's office and, finding it dark, learned from the associate whose office was next door that Jason had taken the week off.

"Did he say why?" Kate asked.

"He said he needs to help Carrie with wedding planning," he replied. "That's all I know for sure. I think he's also trying to burn some vacation time and look for a new job."

"Thanks," Kate said, crestfallen at the news. Wedding planning? They're still going through with it? Jason's wedding was on August 3, less than three weeks away. Wonderful, Kate thought as she walked to her car. Either he goes through with it and marries Carrie, or they break up and I'm the homewrecker.

On the way home, Kate suddenly realized she needed to set up Flanagan's assignation with Becky. Then, remembering her offer to Jane, she recalled that she needed to patch things up with Sam. From her car, she called and Sam answered on the first ring.

"Sam, it's Kate. I'm sorry about Friday night," she said. "I was upset and got too drunk and I know that's no excuse, but I'm sorry for what I said about you."

"It's okay," Sam said. "I have been a bit slutty lately. Especially with Jason."

"Please, Sam," Kate said. "Not now. I have a favor to ask. My boss hasn't gotten laid in forever and I kind of promised her that she could sleep with Matt. You know, to get her back on the horse. I told her you might like to watch."

"Is she hot?" Sam asked.

"Absolutely," Kate said. "She's older, about 55, but she has a great body and a cute face and her tits are enormous. Double Ds, for sure. I think she's kind of a Cynthia Nevil type--used to being in charge and needs to just get a good fucking. What do you think?"

"I'd love to watch Matt ravish an older woman who's even more desperate than you were when you two met. Count us in," Sam said. "We'll be there Saturday night. Make it a nice hotel suite, like the one I fucked Jason in both times."

"Damn it, Sam," Kate said. "Why are you doing this?"

"You're the smart lawyer," Sam said. "You should be able to figure it out. See you Saturday."

The rest of the week Kate worked extra-long hours having to handle her cases and get set up in her new role. By Saturday afternoon she was ready for anything but work and, as she checked into a two-bedroom suite at the city's nicest hotel, happy for the diversion. As planned, Sam, Matt, and Becky arrived at 7:00 p.m. Kate put Becky in one bedroom and Matt and Sam in the other. They were on opposite sides of a huge living area, close enough for Kate to move between them but, she hoped, far enough apart for privacy. Joining Becky in her room, Kate said, "Becky, you look incredible."

"I wore exactly what you said to wear," Becky said. As Flanagan requested, Becky was wearing his favorite outfit--a light blue blouse with a matching sweater, a knee-length black skirt, and black thigh-high stockings. She knew she looked good in it, and often wore it to work since it was both professional and sexy, which Flanagan had obviously noticed. Underneath, she wore black silk panties and a light blue pushup bra that clasped in the front. He hasn't noticed those before, Becky thought, but he will soon. "I'm really excited to get fucked by a long, thick cock. But I'm kind of nervous," Becky said. "I've never taken one bigger than Tyler's. And Matt's. In fact, those are the only two I've ever taken. Kind of sad, huh?"

"No, not at all. Kind of sweet, really. But don't worry, you'll love it," Kate said. "Now let me go check on Sam and Matt and I'll be right back." She closed the door and walked across the living area into the other bedroom, finding Sam and Matt sitting on the bed still waiting for Jane. "You two ready to go?" Kate asked, already knowing the answer.

"Yep," Matt said. "Is it true it's been ten years for her?"

Kate nodded. "And you thought I was bad," she said.

"I still can't believe you hadn't gotten laid in three years before we met in your car," Matt said. "Damn, you two are so hot I want to take you right now."

Just then there was a knock at the door. "Sounds like you won't have to wait long. But remember, ease her into it," Kate said. She left the bedroom to answer the door. "Good evening, Jane, come on in." Jane was wearing a navy-blue skirt suit with a tight white top, likely having just come from the office. Her shoulder-length red hair was down and she looked nervous. "Is everything okay?"

"I'm sorry, I'm just really nervous," Jane said. "My stomach is churning, and my palms are sweaty. I haven't done this in so long."

"Don't worry," Kate replied. "Trust me, Matt is incredible. Here, come on in and meet him." She ushered Jane into the bedroom. Matt introduced himself and shook her hand, as did Sam.

"Wow, you're absolutely stunning," Jane said to Sam.

"Thank you," Sam said demurely. "You are too. Kate, you said she's 55, but there's no way. Look at her! Matt, don't you think she's hot?"

"Definitely," Matt said. "I can't believe I get to be with another gorgeous woman."

"Please," Jane said, blushing. "I don't compare to these two. You don't have to blow smoke up my ass. But it's nice of you to say."

"I'm not just saying it," Matt said, reaching out and taking her hand in his. He put it on his crotch and Jane reflexively pulled back. "It's okay," he added. "I wouldn't be so hard if I wasn't attracted to you. Want to get started?"

"Yes," Jane said. "Sorry, it's been so long I'm kind of out of practice." Matt stepped forward and kissed her, first with just his lips and then using his tongue. He started gently rubbing her breasts, clearly enamored by their enormity. He pushed her against the wall as he fondled them more aggressively, quickly working his hands underneath her shirt. He unclasped her bra and began feeling her up, to Jane's obvious delight. "Oh, that feels so good," she moaned.

"Wait 'til you feel what's next," Matt said as he pulled her jacket off and lifted her shirt over her head. He yanked her bra off and thrust his mouth onto her massive breasts. Kate was impressed with how firm they still looked at Jane's age and, by the way Matt devoured them, a little jealous. Soon Jane's skirt was at her ankles and Matt was fingering her inside her panties as he continued sucking her tits. Just then she heard another knock at the door. Thankfully, Matt and Jane didn't notice, but Sam did.

"Sounds like Flanagan's here," Sam whispered. "Good luck. I'll let you know how this goes." Kate turned to leave just as Matt put Jane onto the bed and removed her panties. As Kate started to close the door she saw his head drop between her legs and, as Jane started to moan louder, got even more jealous. She's in for a treat, Kate thought as the door latched behind her.

Kate went to the main door and found Flanagan waiting, dressed in gray dress pants and a dark blue dress shirt. She asked him to hold on a for a second and ducked into the other room, finding Becky seated on the bed. "Ready?" she asked. Becky nodded. "Great, I'll be right back."

Kate popped her head into the other room just as Jane orgasmed powerfully. By the way her back arched and her hips bucked, Kate could tell it was intense. Jane's loud scream confirmed it and, just as Kate and Sam looked at each other and smiled, Matt said, "Now you need to be fucked hard, don't you?"

"Yes," Jane whimpered. "I need it so bad." Kate knew she needed to get to Flanagan but couldn't resist watching. Matt was quickly out of his shorts and boxers and then inside Jane in missionary position, her legs spread wide and her tits bouncing as Matt started to pound her. Jane whimpered louder and then cried out with pleasure. Wishing she could stay but knowing it would be a while, Kate gently closed the door and retrieved Flanagan from the hall.

"Sorry about that," Kate said. "Just some last-minute preparation. Follow me. Becky is in here."

"Ah, yes, this is perfect," Flanagan said as he entered the bedroom and Kate shut the door behind them, hoping he couldn't hear Jane. Flanagan approached Becky and brushed her hair behind her ear, his hand gently touching her cheek. "It's good to see you again, Becky. What can I do for you tonight?"

"I want you to fuck me the way my husband can't," she said. "His cock is too small to satisfy me the way I need it." She reached down and began to rub his erection. "I need yours inside me."

"I know you do," Flanagan said as he began to kiss Becky's neck. "Your husband is always at work and leaves you home all alone. Aren't you glad you have such a great boss?"

"Absolutely," Becky said. She unzipped his fly and reached inside. "Mmm, a really big boss too," she added seductively.

"I feel bad for you, being married to a resident physician," Flanagan said. "You must be so horny all the time. I bet you've been tempted to do it with a student, maybe even in your classroom or the newspaper office. But I'm glad you came to me instead."

"He's not a res--I mean, yes, you're right," Becky said, catching on to what Flanagan needed. "I have been tempted by a few students, but I'm so glad I waited for you. Much better to have a real man satisfy me. Do you like my outfit?"

"I love it," Flanagan said. "I get so hard every time you wear it, thinking about what's underneath."

"How about you do more than think about it?" Becky said. She took off her sweater and then slowly lifted her shirt over her head, revealing her gorgeous breasts covered now by only her bra. She unbuttoned her skirt and shimmied out of it, standing before him in her thigh-high stockings, silk panties and bra. Becky began to slide her stockings off, but Flanagan shook his head.

"Leave them on," he said. "Wow, your body is even better than I'd imagined." He reached out and squeezed her tits, sliding his fingers inside her bra from the top and rubbing her nipples until they hardened. After a moment Becky dropped to her knees and pulled his cock through his fly.

"Dr. Flanagan, this is incredible," she exclaimed. "It's even better than I'd imagined. All those times I saw you in the hall, I just wanted to drop to my knees and suck you off. It took everything I had to resist, but I can't anymore, especially after last time. I need your cock again." Becky started to suck him slowly as he reached down and continued to fondle her tits with his right hand. "Take your pants off," she directed. "I need your balls too."

Flanagan quickly obliged and removed his shirt too. Now naked, he stood straight up as Becky sucked him off. Kate saw his back arch slightly and said, "Principal Flanagan, don't forget."

"Forget what?" Becky asked as Flanagan pulled her to her feet.

"Don't worry, Ms. Harris, I haven't forgotten," Flanagan said. "This is what she's referring too, Becky." He spun her around and bent her over the edge of the bed. Pulling her panties to the side, he penetrated her from behind. Becky gasped loudly as he entered her and began thrusting gently. Kate saw her face contort a bit at first, but then turn to a smile as Flanagan slid in and out of her. After a few minutes Becky was begging for more.

"Oh yeah, Dr. Flanagan. Fuck me like that," she said. "I need your cock so bad." Suddenly, he stopped. "Don't stop," she said. "Please, don't stop." Flanagan flipped her over and lifted her onto the bed, where he pulled her panties off and tossed them to the floor. He climbed on top of her and began sucking her magnificent tits as he fingered her, making Becky moan and start begging to be fucked again.

"Not yet," he said. "First, you need this." He started kissing his way down her abdomen to her thighs, working his mouth all around her pussy before finally diving in. Kate was happy to see him really go at it, burying his face in Becky's pussy until she orgasmed intensely. As it continued, he penetrated her throbbing pussy again, making Becky cry out with pleasure. He gave her a good, long, hard fucking, first in missionary position, then from behind, then with him standing next to the bed and her legs in the air and her tits bouncing.

Finally, after Becky orgasmed again, Flanagan unloaded inside her, his whole body shaking as his semen poured into Becky. By now soaking wet from watching them, Kate fought off the urge to touch herself, instead slipping out of the room quietly to check on Jane, Matt and Sam.

As she opened the door gingerly, she saw the three of them were in bed. Sam was naked and kneeling next to Jane, rubbing her clit as Matt fingered her vigorously. Just then Jane orgasmed powerfully, spraying her juices all over her thighs and Matt and Sam. Her eyes closed, Jane began to laugh with what sounded like a mix of joy and relief.

"I take it everything is going well in here?" Kate asked.

"Yes, quite well," Sam said. "She was in bad condition when we started. I've never seen someone so backed up. She's already had five orgasms, three from oral, one from Matt screwing her, and now that one."

"Kate, thank you so much for this," Jane said as she opened her eyes. "You weren't kidding, these two are unbelievable. Matt, do you think you could go one more round?"

"Definitely, Ms. Rogers," he replied. "As long as I can suck on those tits again." Jane smiled and pulled his head down onto her breasts. Kate smiled at Sam and left the room, returning to the other bedroom to find Becky blowing Flanagan again. Kate reached inside her skirt and began to touch herself. Moments later Becky pulled off and looked over.