Oral Advocacy Ch. 08: The Tutor

Samantha pulled her car to the side of the road and checked the address again. It still said 1437 Conroy Road, just like last time. She was driving to her first tutoring session with Mr. Nevil on the third Monday in May and she was sure she was lost. The houses were enormous mansions that had to be worth millions. How can a high school teacher afford to live here, she thought as she pulled back onto the road. A few blocks later she saw 1437 on a mailbox and turned onto the driveway.

The house was gorgeous, one of the nicest she had ever seen. Sam had been to this part of town before since a few of her friends lived in the area. However, most lived closer to Sacred Heart, her high school, in an upper middle-class part of town. Their houses were plenty big and certainly expensive, but Nevil's was on a whole other level. Sam suddenly felt out of place as she parked her used Toyota Camry and got out. The house was a brick two-story mansion with an expansive front yard. Everything was in perfect shape and she could only imagine how nice it was inside.

At least I don't look out of place, Sam thought as she walked around the side of the house. She was wearing a form-fitting floral print dress that was short and low-cut enough to get attention while still looking classy. She wore her blonde hair down and knew that at 21 she could likely pass for a neighborhood trophy wife.

Nevil had told her to ring the front doorbell, but her friends had told her his office was in the basement, so she'd decided to use the rear door. Walking around the side and down the sloped driveway, she saw a large swimming pool surrounded by a huge back yard with beautiful landscaping. There was a covered outdoor seating area beyond the pool and a large patio between the pool and the house. How can this guy have such a nice house, Sam thought as she found the back door and knocked. After a while man who looked to be about 50 answered and she said, "Hi, I'm Samantha Gentry."

"Bob Nevil," he replied as he reached out to shake her hand. "I expected you at the front door. I apologize if I didn't tell you where to go." He had a firm handshake and appeared to be about six feet tall. He had a few extra pounds around the middle but otherwise looked to be in decent shape. If I'm going to get hit on and maybe groped, I could do worse, Sam thought.

"No, you did. But I didn't want to bother anyone," Sam said. "I thought using the back door would give us more privacy."

"You can go to the front from now on. Anyway, come on in," Nevil said. "My office is through that door to the left." Sam walked into what appeared to be an enormous basement. It had a pool table, ping pong table, giant seating area with an enormous television, a bar, and several tables. Large windows looked out on the back yard and another set of doors led directly to the patio. I could get used to this, Sam thought as she took it all in. "Wondering how a teacher can afford all of this?" Nevil asked.

"No, not at all," Sam said before pausing briefly. "Well, actually, yes, I am. You have such a beautiful home."

"My wife is the CEO of SND Health Systems," Nevil said. "She gets all the credit. I'm just a humble math teacher."

"That's really impressive," Sam said.

"Yes, teaching high school math is quite the accomplishment," Nevil said.

"Oh, I'm sorry, I meant that--I mean, yes, you're right, it is," Sam said.

"I know what you meant," Nevil said. "I'm just joking around. Cynthia is a very impressive woman who's managed to have an amazing career. Which is great for me, because I can do what I love, which is teaching, and still live in a place like this. Anyway, my office is right through that door."

Sam walked into what appeared to be a home office, with two desks and a small leather love seat. Nevil followed her in and left the door open behind him. He sat at one desk and gestured for Sam to sit at the other before saying, "So, Ms. Gentry, what type of math do you need help with? Geometry, calculus, algebra?"

Sam hesitated, not sure what to say. She was actually quite accomplished at math, having already finished calculus 3 and linear algebra. While it wasn't her major, she found it interesting and was minoring in it. She had come here prepared to play the dumb, ditzy blonde in the hopes Nevil would be into it. But now she wasn't so sure so, on gut instinct, she decided to play it straight. "I could use a little help with linear algebra. I got a B- in it last semester, so a refresher wouldn't hurt. Then I'd like to work on differential equations since I'm taking that in the fall."

"Linear algebra and differential equations?" Nevil asked incredulously. "What high school do you go to?"

"Do I look like I'm in high school?" Sam asked with slightly flirty tone. "I'm 21 and just finished my junior year in college."

"I just assumed," Nevil said. "Everyone I tutor is in high school. But to answer your question, no, you don't. I apologize, it's my mistake." He glanced downward as he said it, just a quick look at her ample breasts that let Sam know he was interested. This shouldn't be too hard, she thought as she smiled back at him.

"It's perfectly okay," Sam said. "Can you help me? If those subjects are too advanced..."

"Not at all," Nevil said, interrupting her. "It'll be nice to work on something beyond the high school level. I have some textbooks around here somewhere that we can use, unless you brought your own materials."

"I have my linear algebra textbook," Sam said. "But I haven't bought the differential equations one yet. Thank you so much for helping me."

"It's quite alright," Nevil said. "Thank you for hiring me. We can use your book. Just let me know what you want to start with." He sat next to her, and Sam showed him a few things she'd struggled with. They spent the next almost 60 minutes working through them. Nevil was quite helpful and seemed excited to be teaching higher-level math. The problem was he didn't appear to be excited in the way Sam had intended. He was a perfect gentleman--no ogling, leering, touching, groping, or anything inappropriate. When the hour ended, he said, "You're good at this, Ms. Gentry. Are you sure you need tutoring?"

"Thank you, that's so sweet," Sam said. "To be honest, I'm kind of an overachiever. When I was playing tennis at Miami, I didn't have much time, so I couldn't take substantive courses like this. Since I hurt my knee and left the team, I've been able to take tougher classes like this. My friends think I'm kind of a dork, taking advanced math classes for fun."

"I doubt very much that anyone thinks you're a dork, Ms. Gentry," Nevil said, taking another glance at her gorgeous body. "Anyway, our hour has ended. Same time tomorrow?"

"I'll be here," Sam said. "And please, call me Sam. Or at least Samantha."

"I guess that would be okay, since you're in college," Nevil said. "In that case, you can call me Bob." Sam smiled and walked out, taking another opportunity to marvel at his house. He's definitely interested, Sam thought as she drove away. A few more days and Becky will be all set.

But Nevil didn't do anything the rest of the week, even with Samantha's increasingly revealing outfits and open flirtation. The closest he'd come was making a comment that he was surprised someone like her was interested in advanced math courses. "What do you mean, someone like me?" Sam had asked innocently.

"Well, you were a college athlete and you're so..." he answered, trailing off.

"So what?" Sam insisted. "Are you talking about the way I look?"

"Sorry," he said. "Forget I said anything. Let's get back to work."

"It's okay," Sam said. "Trust me, I know what you mean. I'm the one going to the classes. And I know how I look." She put her hand on his forearm and added, "It's okay if you say I'm pretty. I'm not one of those girls who gets offended by that."

"Thanks," he said. "Still, I shouldn't be commenting on your appearance. You hired me to tutor you in math, not comment on how you look. I think I've said enough. Want to get back to work?"

That was the closest he'd come to doing anything inappropriate. As her first week of tutoring ended, Sam knew it wasn't even close to enough. A couple quick glances and a mildly awkward comment, which wasn't even really anything, weren't going to help Becky. She was going to have to step up her game next week.

After a Memorial Day break, they spent the first three sessions of the next week mostly talking about things other than math. It was clear Sam didn't really need tutoring in linear algebra and, based on the schedule she'd suggested, they had plenty of time to get to their next subject. Sam found she actually liked Nevil. He was funny, really smart, and a complete gentleman. She could tell he liked her too and that he was into strong women. Because of that, and since he wasn't a creep, she knew he wasn't going to try anything inappropriate. But Samantha needed him to initiate it. Ripping off her clothes and throwing herself at him would be too obvious and would likely backfire.

That afternoon she called Kate with the bad news. "I know he's meeting with the lawyers tomorrow, but I've got nothing. You need to get me more time," Sam said.

"It's not up to me," Kate said, clearly frustrated. "They won't even let me in the building, much less the meeting. You said this would be easy. What happened to the short skirts and tight dresses and the flirting? I thought no man could resist you."

"Apparently this one can, at least for a while," Sam said. "Just get me a couple more weeks. Work your high-priced lawyer magic. He canceled tomorrow's session, probably so he can go to the meeting, but I'll see him on Monday."

Kate quickly called Henry, who was still working in the principal's office as his summer job even though he'd graduated. "I need you to get tomorrow's meeting postponed," she said. "I'll do anything if you can help me."

"I have a couple ideas, but I'll take a raincheck," Henry said. "Besides, it's already done. I was just about to call you. James met with them today and apparently it didn't go well, at least for them. It went great for Becky. It sounds like he told them he imagined everything and that it was really a big wet dream that he told Nevil about and then lied because he was embarrassed. Sounds like they aren't totally buying it, but they postponed Nevil's meeting while they can figure out what's going on with James. You have an extra two weeks."

Way to go James, Kate thought. She'd have to give him especially good head tonight. Maybe even three times. Kate had been sucking and fucking James almost every day for the past few weeks, an investment that was now paying off. More accurately, it was paying off extra. Kate loved getting it every night and thankfully James was insatiable, so this was just the icing on the cake. "Thanks so much, Henry," she said. "And if you ever want to stop by for a thank you, just let me know."

Kate called Sam right away and let her know the good news. "That's great to hear," Sam said. "And don't worry, I'll hold up my end of the bargain. This is tougher than I thought, but I love a challenge."

On Monday Sam returned to Nevil's house for more tutoring, entering through the back door as she always did despite his repeated instructions to use the front. While they sat next to each other and chatted for a while about various subjects, math not one of them yet, Nevil mentioned his wife Cynthia had won a national award for hospital CEOs.

"Wow, she's a really impressive woman. So accomplished and smart. And pretty," Sam said, gesturing toward her picture on his desk. "You're a really lucky guy."

"Yes, she is." Nevil said. "And that's true, I am really lucky." He sounded a bit unsure as he said it and Sam detected an opening.

"You don't sound so sure," she said. "Is everything okay?"

"Yeah, it's fine," he said. Sam looked directly into his eyes and didn't say anything. After an awkward moment, he added, "I know I'm really fortunate, I do. But it's not always easy being Mr. Cynthia Nevil, you know? She's so accomplished and well-known, on the boards of a bunch of companies and invited to every public event in town. I'm just a high school teacher."

"I think you're really smart and that your work is really important, even if society doesn't recognize it like we should," Sam said. "And I think it's very impressive that you can handle being with a strong, accomplished woman. Not every guy can handle us, you know?"

"That's what Cynthia always says," Nevil replied. "I wouldn't have it any other way, I really wouldn't. It's just that with her working all the time and going to meeting after meeting and event after event we hardly see each other so we don't--never mind, forget I said that."

"Do it enough?" Sam asked. Nevil nodded. "Don't worry, I'm 21." Then, in a mock whisper, she added, "I know adults have sex."

Nevil laughed. "Yes, I suppose you do," he said. "Sorry, that just kind of slipped out. I find you easier to talk to than most students and sometimes I forget you're in college. But even then, I shouldn't have brought it up. That's not what you're here for."

Actually, that's exactly what I'm here for, Sam thought. Instead, she said, "It's okay. Trust me, I can sympathize. My boyfriend is back at school all summer and I haven't seen him for weeks." She uncrossed her legs and spread them ever so slightly, hoping he'd notice.

"Yes, I suppose that's difficult," Nevil said as he subtly glanced down, a hint of nervousness in his voice.

Sam smiled and said, "You're lucky you're in the same city as your wife. The same house, even."

"Yes, I am," Nevil said. "Everything's great. Ready to start on differential equations?"

"You don't sound so sure," Sam said flirtatiously, opening her legs a bit more. "Is everything okay? You can tell me anything, I promise I won't tell anyone."

"Well, it's just that with work and the kids and everything going on we don't see each other much," Nevil said. "And when we do, she thinks it's beneath her to..."

"To what?" Sam said. "It's okay, you can say it."

"To give me a blowjob," Nevil said.

"Really?" Sam asked with a surprised tone. "She doesn't do that for you?"

"No, not in a long time," Nevil said. "Probably fifteen years. But I really shouldn't be talking about this with you. I'm sorry for being inappropriate."

"I like being inappropriate," Sam said mischievously. "And I'm surprised she won't do that, since she's a strong woman who's used to being in charge. Nothing puts you in control of a man like having his dick in your mouth."

Nevil gulped and Sam let her legs open a little more as she sat up straight and thrust her chest forward. "I guess that's, uh, I guess that's true," he said, sweat starting to form on his brow. Sam could tell he was uncomfortable and not sure of what to say next.

"Thank you so much for helping me with math," she said. "You're a great teacher. If there's ever anything I can do to thank you, please let me know right away." She spread her legs wider and scooted forward in her chair, his right knee now between her legs as they sat facing each other.

"You're welcome, but, um, I, uh, I don't think that will be necessary," Nevil said. "Thanks for listening. It felt good getting that off my chest."

"I like making men feel good," Sam said. "Are you sure there's nothing else I can do for you?"

"Yes, I'm sure," he said as he stood up. His erection was visible through his pants and, as Sam stayed seated, ended up right in front of her face. Nevil turned red as he looked down and saw Sam looking at it before raising her eyes to look at him.

"I don't believe you," Sam said. "You're so hard. You want me to take care of that for you, don't you?"

"I shouldn't do this," Nevil said.

"It's okay," Sam said. "I know you want me. Do you want me to make you feel good?"

Nevil nodded. Sam reached out and began rubbing his cock through his pants. "Oh, that feels so good," Nevil moaned.

"It's been much too long," Sam said. "I don't think you should have to wait another second." She unzipped his fly and reached inside. Nevil groaned with relief as her hand gripped his shaft and stroked it as she pulled it out. It was rock hard and she began to kiss it before saying, "I need you to take off your pants." Nevil immediately obliged and moments later his boxers and pants were around his ankles, his entire dick available for Sam to kiss and lick. She pushed his shirt up and he took it off, giving her full access. "Do you like it slow or fast?" she asked.

"I'm sorry, we shouldn't do this," he said. Sam just looked up at him, a flirtatious smile on her face. "Okay, slow," he said as she took his head into her mouth and sucked it a few times, swirling her tongue around it for good measure. "Oh God, that feels so good. Oh yeah, that's so good." She felt his knees buckle slightly as she moved her lips down his shaft, taking several inches into her mouth. Sam moved back up slowly, savoring every inch of him and evidently driving him wild. Over and over he cried out, "Oh yes, oh yes, oh God" as she gave him a slow, deliberate blowjob.

After a few minutes Sam felt his cock start to twitch. She didn't speed up, instead going deliberately at about half her normal speed. She could tell he liked it by the precum leaking into her mouth and his repeated twitching. She fondled his balls and squeezed them gently, causing Nevil to stiffen further and cry out louder.

Sam knew he was close. She tightened her lips a little and took him a little deeper, just before the point at which she would gag. With her left hand she felt his thigh, which was tense as his orgasm built. Sam kept going slowly until she felt Nevil push forward and let out what sounded like a roar as cum exploded from his cock. Sam continued as he filled her mouth with semen, his hips thrusting forward as he shot into her multiple times. She sucked him slowly until he put his hands on her shoulders and pulled back, saying, "Oh God, that's too intense."

Sam released his cock and looked up at him. He was hunched over slightly, apparently weak in the knees. His eyes were still closed and he was smiling, a look of joy and relief on his face. As he slowly opened his eyes and looked down, Sam swallowed and said, "That was just what I needed."

"Me too," he said. "That was incredible. I've never had a blowjob that felt that good."

Sam stood up and kissed him on the cheek. "I'm glad you liked it," she said. "See you tomorrow." She grabbed her purse and walked out, leaving Nevil with his pants around his ankles. As she drove away she got her phone and started to call Kate but, just as she finished dialing, flipped it closed. Once wasn't going to be enough, she thought.

The next day she showed up for her tutoring appointment to find Nevil pacing in his basement. He ushered her quickly into his office and shut the door. In a low voice, almost a whisper, he said, "Sam, I'm really sorry about yesterday. I don't know what got into me. I mean, I do, but that's not the point. My behavior was totally inappropriate and I promise it will never happen again."

"That's incredibly disappointing," Sam said, frowning. "Like I said, I like being inappropriate. Did I not do a good job?"

"No, you did a great job," Nevil said. "But I'm a teacher and you hired me to teach you math, not have you give me oral sex. I'm sorry. Are you going to tell my wife? Because I'm not going to tell you not to and you can do what you want but I was hoping that you wouldn't and..."

Sam put her hand on his arm and said, "Bob, don't worry. I won't tell her. And you're right, I hired you to teach me." Nevil exhaled, clearly relieved. "So do you think you could teach me how to make out with an older man?" she added. Sam was wearing a super-short skirt that barely covered her firm ass and a tiny tank top that left several inches of her flat abs visible. As Nevil looked at her with surprise, she stepped forward, her body pressed against his. He was a few inches taller than her 5'7" frame and, as she looked up at him, she added, "Please? I need more tutoring."