Oral Advocacy Ch. 06: The Teacher

Then Matt knelt and slid her panties to her ankles, allowing her to step out of them. As he began to kiss her stomach and thighs, she said, "Not tonight." Gesturing for him to stand, she led him to the bed and dimmed the lights. She slowly took his jacket off and loosened his tie, lifting it over his head as she stood naked before him.

Becky began to unbutton his shirt until she reached the lowest button. Unbuckling his belt and unbuttoning his pants, she reached inside and fondled his erect cock. "I can't wait to feel you inside me," she said. Becky unzipped his pants and let them fall to the floor. Matt worked his way out of his shoes and socks and stepped out of his pants as she unbuttoned his last shirt button and took it off.

Kneeling before him, she teased him and took off his boxers. His cock inches from her face, Becky desperately wanted it in her mouth. As she looked up at him, she said again, "Not tonight." Standing up and climbing into the bed, she lay in the middle with her legs spread. Her tight, shaved pussy beckoned and Matt climbed onto the bed, kissing her as he lay on top of her. He worked his way to her breasts, sucking and fondling her nipples and making her wet with anticipation.

As he started to kiss her stomach, Becky said, "Not tonight. I said I want you inside me." Looking up, Matt smiled, looking eager and unsure simultaneously. "It's okay," she said. "I want to be your first." He moved up and kissed her again, his erection pressing against her lower abdomen. After a while she said, "I'm ready."

"I don't have a condom," he said.

"You don't need one, I'm on the pill. I want you to enjoy your first time," Becky said. Reaching down between his legs, she guided his cock to the entrance to her vagina. Becky was wet and ready. Pausing briefly, Matt slid inside Becky for the first time.

She whimpered as he entered her, her tight pussy loving the feel of his hard cock sliding deep inside. He began to hump her gently, slowly building in intensity as he made love to her for the first time. Becky whimpered louder and wrapped her arms around him, pulling him inside her as deeply as possible. Her tits bounced as he began to penetrate her more vigorously, a look of determination on his face. He thrust harder and harder, Becky by now soaked as he pounded away. She saw his face contort and closed her eyes, squeezing her pussy as tightly as she could.

Matt thrust one last time, pausing deep inside her and shuddering as he let out a guttural sound and came inside Becky. He thrust a couple more times, with each thrust he was unloading more semen inside her. Then he lay on top of her, their naked bodies pressed together with his cock still inside her vagina. Breathing heavily, he withdrew once he softened and then lay next to her.

Becky snuggled up next to him and lay her head on his chest. She didn't say a word, letting him revel in the experience. His cum began to dribble out of her, sliding onto her left thigh as she lay on her side. Becky flipped the lights off and pulled a sheet over them as she again lay her head on his chest, falling asleep with him in the darkened hotel room.

In the morning, a glimmer of sunlight shown through a gap in the curtains. Matt was still asleep, his morning wood lifting the sheet as he lay on his back. My turn, Becky thought eagerly as she carefully lifted the sheet off and straddled him. She got wet quickly, having fallen asleep emotionally satisfied by taking Matt's virginity but needing sexual relief.

As she lowered herself onto him, she felt his cock at the entrance to her vagina. It was unbelievably hard, even harder than last night. Becky moaned as she pushed down and felt Matt inside her. She took him all the way inside a few times before grinding against him. By now he was wide awake and eagerly fondling and sucking her tits as she rode him. As her orgasm built, she grabbed his hands and put them on her ass. Taking the cue, he squeezed it hard and pushed into her, taking her over the edge.

Continuing to ride him as her orgasm went on, she moved her hips up and down so that her pussy went from base to tip. Drenching him with her juices, she rode him until he arched his back and thrust upward, spraying his cum inside her. She felt it begin to ooze out as she knelt with him still inside her. Becky smiled as she raised her hips, drops of cum dripping onto the sheets.

She snuck downstairs and grabbed some breakfast, running into Jeff and Samantha in the lobby. Jeff smirked at her and said, "Did you enjoy your night with your boyfriend, Ms. Tapper?" Becky just frowned and told them to move along. Man, if they only knew who was upstairs. And man, that Samantha was unbelievably pretty.

Returning to her room, after she and Matt showered she noticed they still had an hour before checkout. "Think you can go again?" Becky asked.

"Absolutely," Matt said. This time she had him take her from behind, her face laying sideways on the mattress and her ass up as he knelt behind her. He had to work for this one, giving Becky the chance to scream, "Fuck me harder! Fuck me harder!" over and over until he was railing her as hard as he could. Able to position herself so he hit her G-spot, she engineered it so she had another orgasm just before he unloaded his third load into her aching pussy.

"How does it feel getting laid three times?" Becky asked after they dressed.

"Awesome," he said. "I'm completely drained. I've never felt like this from masturbating. I don't know if I can even get hard."

"You better be ready Monday," Becky said as he slipped out of the room first and headed for the stairs. She took the elevator, thankfully avoiding anyone they knew.

Over the next few months, Matt and Becky continued to meet up almost every weekday. He'd stop by her house on the way home after school or come over on Friday nights, letting his parents think he was out with his buddies. Sometimes he'd do both, stopping to fuck Becky on his way to a party or on his way home from one. A few times their desire got the better of them and they did it at school, mostly in the newspaper office since it was out of the way.

He got better and better at kissing, oral, intercourse, dancing, giving her massages, everything. Becky taught him how to behave with women, how to please them, how to last longer in bed, how to converse, all that he needed to know to be a great boyfriend and a great lover. She found herself craving his touch and his cock and, most of all, his company, unable to stop what she'd started.

Once, in late March, Becky was in her classroom on a Saturday when she saw Matt in the hallway through the window in the door. Gesturing for him to come inside, she asked, "What are you doing here on a weekend?"

"I'm on my way to the baseball game," he said. "I cover the team for the newspaper. I just needed to grab a few things from the office."

Becky looked at him flirtatiously, turned on by the idea of finally doing it in her classroom. Glancing out into the hallway and seeing no one around, she closed the door behind her and led Matt to her desk. Sure, she thought, someone could walk by and see us at any time. But this will only take a minute, she thought as she began to kiss Matt. She was wearing a sweatshirt and jeans, not a sexy outfit by any means. But her breasts still poked at the sweatshirt and she could feel his excitement as she fondled his cock.

Moving quickly, they both pulled their pants down and Becky bent over her desk, their backs to the door. Pulling her panties to the side, Matt began to finger her from behind as she moaned with pleasure. When she was soaking wet and begging for his cock, he slid it inside and fucked her hard, her panties still on. Becky's head and torso slid back and forth against the desk as he pulled her hips toward him with his hands while forcing her forward with each thrust.

Turned on immensely by doing it in the classroom, they came almost simultaneously. Looking up as she lifted herself off the desk, cum dripping onto the floor, Becky yanked her pants up. Her panties were soaked with Matt's cum and her juices but, as she looked into the hallway, she sighed with relief. They'd gotten away with it. "Enjoy the baseball game," she said. "I can't wait to read about it on Thursday."

A couple weeks later, at the beginning April, everything changed. Tyler started making a big deal about her 26th birthday on May 1. Becky knew he was going to propose. Suddenly nervous about it, she thought about what she should do. Of course, she was going to say yes. She loved Tyler and her fling with Matt was just sex, while Tyler was unavailable. And getting to fulfill her fantasy of taking someone's virginity, just like Tyler had taken hers. The fact that Matt had been so attentive to her needs and become an outstanding lover was icing on the cake.

But it was time to stop. She knew she couldn't continue carrying on with Matt if she was engaged. And it had to end anyway. He was graduating and heading off to college to start the next chapter in his life. She wanted to send him off in style. He was incredible in bed by now. He knew exactly how to please her, having gone down on her or fucked her hundreds of times since early November. But while he knew what she liked, it needed to translate to other women. Thankfully, it just so happened she knew exactly the right person.

Becky's sister Kim was due to arrive for a weeklong visit the first Saturday in April. Kim was three years younger and looked so similar to Becky it was obvious they were related. Kim was a single mom, left to raise now 4-year-old twin boys by her deadbeat high school ex-boyfriend. She was also incredibly hard to please in bed, something Becky had heard about enough for two lifetimes.

"So, are you dating anyone?" Becky asked as she and Kim sat in her living room catching up. Kim laughed out loud.

"Yeah, 4-year-old twins are just what single guys in their early 20s are looking for," Kim said. "As soon as they find out, they're gone. Plus, it's not like I have the same body I had before. Unlike you, I might add. You look incredible."

"Thanks," Becky said, blushing. "Since I'm basically single now too, I've had plenty of time to work out.

"What do you mean single?" Kim asked. "Did you and Tyler break up?"

"Oh, God no," Becky said. "In fact, I think just the opposite." She explained his work schedule and her suspicions about her birthday.

"Well, at least I'm not the only one not getting any action," Kim said. "But don't worry, it's just temporary. At least for you."

"About that," Becky said. "I've actually been getting a lot of action." She proceeded to tell Kim everything, in full detail, as her sister sat looking at her in shock, her mouth open but apparently unable to speak. "So that's where things stand now," Becky continued. "I know I need to end it, but he's just so freaking good in bed I don't know if I can."

"Holy shit, Becky," Kim said. "This is real, you're not messing with me?"

"It's all true," Becky said.

"Becky, this is crazy," Kim said. "It's so unlike you. Of course you have to end it. You could lose your job or your teaching license. Not to mention Tyler. Does he know?" Becky shook her head. "Are you 100% sure?"

"He doesn't have any idea," Becky said. "There were a couple close calls when Matt had to hide under the bed and then sneak out, but Tyler's clueless. And you can't tell him, you understand?"

"I won't say anything," Kim said. "But you need to end it. Like, now, Becky."

"I know, I know," Becky said. "I'm hoping you can help me out with that." Kim gave her a confused look and Becky added, "This all started with me trying to build Matt's confidence so he could get a girlfriend. Admittedly, it got a little out of control. Okay, maybe a lot out of control. Anyway, I know he's confident with me. But he needs to be confident with other women, too."

"What does that have to do with me?" Kim asked.

"I want you to spend the week letting Matt pleasure you. After all, if he can get you off, he can get anyone off," Becky said.

"I'm not that bad," Kim said defensively. Becky looked at her skeptically. "Okay, so maybe I am. But no, I'm not sleeping with your student. This is too weird. And how do you know he'd be into it?"

"He'll be into it, don't worry. And think about it rationally," Becky said. "You need to get some action. It's just foreplay and oral. You don't even have to reciprocate, I can take care of that. You know you need it bad and I'm telling you, he's absolutely incredible."

Kim started to speak but stopped herself. After a long pause, she said, "So he'd go down on me every day this week and I don't have to return the favor?"

"Nope," Becky said. "I'll take care of that, trust me."

"And when would this start?" Kim asked.

"In about 20 minutes," Becky said. "I told him to come over at 4:00."

"Damn it, Becky, I need to get ready," Kim shouted as she ran to the bathroom. When Matt arrived, Becky introduced him to her sister and they talked for a while, Matt appearing a little off guard with the unexpected visitor. When the conversation started to peter out, Becky dropped their surprise.

"Matt, I'd like you to take Kim into my bedroom and go down on her. Foreplay first, of course. She's incredibly horny and notoriously unable to orgasm. It's almost impossible to get her off, but I'd like you to try."

"I'm not that bad," Kim protested.

"Yes, you are," Becky said. "How often do you orgasm from oral? Like one in 50 times? Thankfully, Matt here is quite talented."

Stunned, Matt sat in silence for a half minute before saying, "You mean like right now?"

"Yes," Becky said. "And every day this week, if you don't mind. Is that okay with you?"

"Yeah, if you want me too," he said. Becky could tell he was nervous, which is exactly what she'd hoped. If he could make Kim climax he'd be confident he could please anyone. He led Kim into Becky's bedroom and closed the door. Becky could still hear their conversation as she stood at the door.

"Sorry, this is kind of awkward," Kim said.

"Yeah, it is," Matt said. "I certainly wasn't expecting this. But I have to say, I'm very lucky. I find you incredibly attractive."

"Really?" Kim said. "Most guys don't, at least anymore. Once they hear about the twins they take off running."

"I guess I'm attracted to strong women," Matt said. Good one, Becky thought. "Raising two kids on your own, having a career, that's impressive. And you're quite pretty." Becky heard them start kissing and went to sit on the couch, giving them some privacy.

About 30 minutes later, she heard Kim say, "I'm so sorry, Matt. It's not you, it's me. I don't know, I just can't do it. I barely ever could."

"Is there something you'd like me to do differently?" Matt asked as Becky moved to the doorway.

"No, you're doing great. I mean it. I just, I don't know, I freeze up and get inside my own head and then I lose it. I was close, and you were great. I'm sorry."

"When's the last time you had a massage?" Matt asked.

"Who knows?" Kim said. "Probably a hundred years ago."

"Flip over, relax, and let me try again," Matt said.

"Fine, but I'm telling you, I can't do it," Kim said. Moments later Becky heard her moaning and talking about how good it felt. As the recipient of many of his massages, Becky knew exactly how she felt. She got wet just thinking about it and hoped her sister did too. As time wore on, Kim started moaning louder and then started saying, "Oh yes, that feels so good. Oh God, oh God." Kate knew Matt was stroking Kim's pussy as she lay face down, her legs now spread wide to invite him in.

Shortly thereafter, she heard movement and knew Kim was flipping onto her back. "Just relax," Matt said. "Take a deep breath and let me do all the work." Becky knew his head was now between Kim's legs, his tongue licking every millimeter of her aching pussy.

Returning to her seat on the couch, she hoped Kim would be able to get off. A few minutes later, her worries eased. Becky heard Kim start to yell, "Oh fuck yeah! Fuck yeah! Just like that! Make me cum! Oh yes!" Kim continued for several minutes, Becky not knowing until then how vocal she was in bed. Finally, Kim let out a scream that could probably be heard outside. Man, she really did need that, Becky thought.

A few minutes later Kim and Matt emerged, a look of relief mixed with joy on Kim's face. "Thank you," she said sincerely to Becky. "And thank you," she said to Matt.

"Why don't you take a few minutes to get unpacked," Becky said. "You can take a warm bath if you'd like."

"Yes, that sounds lovely," Kim said. "That'll give you time to give Matt here his reward for a job well done." Becky just smiled as she led Matt into the bedroom, where she blew him and rode his cock until he came a second time, just after she did.

They continued throughout the week, Matt stopping by after school or, when Tyler was home, meeting them at his house before his parents got home from work. By the following Friday, when Kim flew home, Matt had proven that, by getting her off six nights in a row, he could satisfy anyone orally.

That night, as they lay naked in bed, Becky asked Matt who he was taking to the prom, which at Trinity happened the Saturday after finals ended, in mid-May. Prom and graduation were the two big social events for the seniors in the spring, and Becky didn't want Matt to miss either.

"I don't know," he said. "I don't really have anyone in mind. I was thinking maybe I'd just go with Lauren, one of my friends from work."

"That could be fun," Becky said. "What about Samantha Gentry?"

"That's funny," Matt said, laughing.

"I'm serious," Becky said. "You should ask her to prom."

"Are you kidding me?" Matt asked incredulously. "There's no way she'd go with me."

"Don't you think she's pretty?" Becky said.

"Yeah, of course I do. She's smoking hot," Matt said. "I mean, she's not the hottest woman I know, just the hottest senior."

"It's okay," Becky said, smiling and patting his stomach as her head rested on his bare chest. "You can think we're both hot. Anyway, for two years all I've heard is how hot Samantha is. Everyone at school talks about her, you know, and I can't help but overhear. I thought it was overblown, but then I saw her at the winter dance. I have to say, she's even prettier than advertised. I think she's the most beautiful woman I've ever seen in person."

"She's top two for me," Matt said. Becky winced. She was in too deep and needed to get out. "This is all just daydreaming, though. She'd never go out with me. I'm not an athlete, I'm not in the cool group, I'm not the best-looking guy in school. She can pick anyone she wants."

"You don't know if you don't ask," Becky said. "And I hear she's single now. Don't you work with her on the weekends? Why don't you ask her tomorrow?" She let her left hand wander down to Matt's crotch and began lightly caressing him with her fingertips.

"I don't know, it'd be embarrassing. I'd ask her and get rejected and then everyone would laugh at me for even trying," Matt said as he began to stiffen. Becky started to lightly stroke his cock.

"I think you should do it," Becky said as she crawled between his legs and began to kiss him everywhere but on his dick.

"Okay, I'll ask her," Matt said, unable to resist. Well, at least if she says no he gets to cum in my mouth again, Becky thought as she sucked him off.

The next evening Matt stopped by and told Becky that Samantha had said no. He'd talked to her at work, made a few jokes, looked her right in the eye and asked her if she'd go to the prom with him. By the way she looked away, he knew it was a no. She had some reason about not getting involved with anyone and taking a break now that she and Jeff had broken up, or something like that. She'd been nice about it, but as he expected she rejected him.