tagFirst TimeTeach Me

Teach Me


Author's note: This is my FIRST ever. So feedback is welcomed and appreciated. Should I continue? Not my best work, but my roommate came in when I was trying to finish it up and startled the crap out of me.


The way she always stuck the tip of her pen in her mouth drove him nuts. It wasn't that she was doing it on purpose—no, he could tell. Some of his students were provocative young girls. Jailbait in miniskirts and push-up bras. Not Jenny. The pen slipped between her lips when she was deep in thought. Staring out the window or up at the blackboard. She barely seemed to notice him. Jenny never dropped things, never bent over to give him a better look down her shirt or spread her legs wide enough that he could look up her skirt when he sat low enough at his desk. She didn't even sit near his desk.

It wasn't until half-way through the semester that he greeted the students at the door and got a whiff of her delicious scent. No perfume, he guessed, probably just shampoo mixed with her own natural aroma, but to Jake Wilson, senior English teacher at South Side High, it was intoxicating. He closed his eyes and breathed deeply every time she passed him by. The scent alone caused a familiar stirring in his pants. But even as he dreamed of her the answer was always no. This was a student! Eighteen years old and God only knows how inexperienced. Kids these days were ahead of the times, but he just couldn't picture Jenny Holt on her back with her legs spread, or kneeling in front of some guy's dick with her mouth open and ready. Well, he could, but not for anyone but himself. She must be a virgin, he thought, and the idea drove him wild. Her insanely tight, untainted pussy completely sheathing his hard cock. It was enough to make him cum on the spot.

"Mister Wilson?" a voice brought him back to reality. He was in class! It wasn't even Jenny who roused him from his daydream, damnit. She was still completing her assignment, writing as quickly as her hand could slide across the paper. He answered the question of the student who interrupted him and then excused everyone who was finished with their work in hopes that Jenny might stay back. She was meticulous in her work, and everything else, he assumed.

Once the class had cleared out and she was the only one left, still writing with a fury, he moved over to sit on the student desk next to hers, "Jenny, the class is over, you can turn it in as you have it."

She absently licked between her lips and looked up at him, innocently batting her eyelashes once or twice as she smiled slightly, "I obviously wasn't paying attention." But as soon as she said it, she was already cleaning up her things, packing them away and before he could say much more, she was out the door.

"Damnit," he cursed under his breath, figuring it was just as well, probably better that he not be alone with her. When he stood up, he could feel the tightness below his belt. He needed relief.

The students were at lunch and his desk was situated just so that no one at the window could see in. He thought maybe, just maybe he could get away with beating off, release himself before his next class so that he didn't lose himself in a daydream the way he had previously. He sat down and unzipped his pants, lifting his butt off of the chair to pull them slacks down just enough so that he could wrap his hand around himself. He closed his eyes and imagined Jenny, starting to slowly pump his hand up and down, his erection growing harder. Without paying attention to anything that was going on around him, Jake continued to pleasure himself.

When Jenny opened the door and reentered the classroom she gasped loudly. She was visibly shocked and stunned as she let the door slam behind her and stood frozen, staring at her teacher, "I...Oh my God, I'm so sorry," she covered her eyes and turned around, unsure even then why she didn't just run, "I left my lunch..." she started to walk toward the desk she'd been sitting at with her back turned to Mister Wilson.

He jumped up and quickly zipped his pants, "Jenny, I'm so --holy shit, I mean," he covered his mouth and mumbled 'fuck' to himself just as she turned around with those wide doe eyes of hers and blinked at him. "I didn't think anyone was coming back." Jenny nodded her head. He winced and took a step toward her, "Don't tell anyone about this?" he touched her arm and she pulled back for a second, but not so much that his hand was removed from her.

Her skin felt like it might light on fire when he touched her, after what she'd just witnessed. She'd never been with any boy before, never seen a naked penis. But that didn't mean she didn't have hormones, nor that she didn't have questions or curiosities. She swallowed hard and tried to laugh it off quietly, "You uh...I guess you have to do what you have to do?"

"Do you?" He asked.

Without thinking she replied, "Only once or twice." In answer to a question he hadn't even known he asked. When she heard the words fall out of her mouth she gasped and covered her mouth with her hands, "I'm so, oh my god," her face turned red as a raspberry as she stood there, feet planted firmly on the ground.

"It's alright," he smiled just slightly, "Everybody does it. Sometimes...nah." He thought he'd test the waters, see what this girl who was obviously curious would allow. It wasn't like he was old and decrepit. He could be her older brother at best, but not her father.

"What?" She asked.

"Oh nothing," he turned to walk away, "I was just going to say that sometimes it's better with another person. Well, not sometimes, always. Feels better, you know?"

"No," Jenny shook her head, "I don't. I mean, I've never.." she took a few more steps toward him, "Anything."

He turned to look at her again, "Nothing?"

She just shook her head and licked between her lips, her tongue covering them in a light sheen.

Jake looked around and then his eyes caught the door. That would be bad. If she walked in, anyone could. So, he made his way across the room and locked the door, catching her eye, "Is this okay?"

Jenny just shrugged, how was she to know if it was okay? Clearly it was against the rules, but the mere touch of his hand on the bare skin of her forearm sent a bolt of energy, and a rush of blood to the area between her legs, "Maybe..."

When he crossed the room to where she was again, he kept his back to the door and leaned down, his hands grasping each of her arms, and kissed her jaw line.

She expected him to kiss her mouth, but her skin lit up, and it felt so much more erotic than a kiss on the mouth would. She moaned softly and let her arms drop to her sides, her backpack sliding off of them to the ground.

When he saw she was willing, Jake pulled her hand toward the other side of the classroom, once again out of view of the window, picked her up and placed her on his desk. Her skirts were never short like the "slutty" girls, but he could just catch a glimpse of her knees. He put his hands on them and slid up to her thighs, gently squeezing the flesh there, "Mmm," he smirked a little and waited for any hesitation or resistance from her. When none came he leaned in to kiss her neck as he moved his hands up and ran his fingers along the sides of her panties.

"Oh god," she moaned against and scooted her hips forward to the edge of the desk, "Whoa." She didn't know what else to say, or what to do, but she reached her arms up to wrap them around his neck just the same.

He looked up and asked, "More?" She just nodded. And so she felt her teacher slip one finger under the hem of her panties and touch the swollen, wet, outer lips of her pussy. She gasped even louder as the rough skin of his finger dragged along her delicate slit and pressed against her clit, "Holy shit," she found herself cursing, which she hardly ever did, and he smirked at her.

"You like that?"

"I love that," she said with much more gusto than she probably would have liked. And despite knowing that this was against the rules, she couldn't help herself. She reached down and pulled her panties off, setting them on the desk next to her.

Jake took that as a sign and knelt in front of her. He pushed her skirt up to her waist and spread her legs apart wide. He gazed at the glistening flesh before him and sighed with contentment, he'd wanted this for so long, "God Jenny, your pussy is so fucking gorgeous."

That made her blush. No one had ever said that to her, or seen her bare like this before and she didn't know how to react, "You really like it?"

"I do. Don't all the boys tell you that?" He knew it was a loaded question, a way to get her to confirm for him once more that she was a virgin.

She shook her head, "Never been with a boy like this." As she spoke, he returned his hand to her center and used his fingers to spread her pussy lips apart and licked from her hole up to her clit. He wrapped his lips around it and hummed to give her a nice vibrating feeling. Not used to this, Jenny pressed her palms against the desk and lifted herself up slightly, almost trying to get away from him, but at the same time lifting herself toward his mouth. He lapped at her with his tongue and slipped his middle finger into her hole and muttered, "Oh shit you're so fucking tight."

"Nothing's ever been...in me," she swallowed hard and moaned against when he started to pump his finger in and out of her faster. His finger curled up toward her Gspot and stroked it gently. Jenny didn't know what to do and fell back against the desk.

Jake pulled his pants down to his knees and reached out for her hand, wrapping her milky white fingers around his hardening dick, "Touch it," he said. And she did. It was one of the most amazing feelings, his cock hardening in her hand as she rubbed her thumb over the head, touching the hole in the tip and wishing she could put it in her mouth, but not daring to do so. It felt so big and strong, but she didn't know what to do with it.

He crawled up onto the desk, hovering over her, and then she knew. She could feel the burning in the pit of her stomach, she needed release. She took him in her hand and placed his cock at the entrance to her pussy. It felt so good and she couldn't help but rub it all along her slit, feeling the tip press against her clit when he got too excited.

"Fuck Jenny, I need to be inside you."

Then she got scared. She sat up and swallowed hard, "But h-how. I don't know. I've never. I mean..." she shook her head.

He resumed kissing her neck and smiled at her when he pulled his head back to make eye contact again, "I'll let you control it. You can watch it go in and stop me." Famous last words, he thought, knowing damn well once he felt her, he wouldn't be able to stop.

She nodded her head slowly and felt her teacher tug her to the edge of his desk. He spread her legs wide by pushing her knees apart and stood between them. "Ready?" He asked.

She winced and shrugged, but who is ever ready?

He placed the head of his dick at her hole and pushed forward, feeling himself press just barely into her. The thick head of his cock slipped past the first barrier of her, just barely a half inch inside her.

Already it felt amazing. There was a twinge of pain as she felt like something was stretching her apart, but every time she sucked in a breath it felt like heaven. "Okay more," ask commanded and Jake happily obliged. He pushed his hips forward more, and a little more until he felt himself come against her hymen. This was it, the mark of her virginity he was about to take.

He didn't even bother asking her this time, he pulled her forward to the edge of the desk and shoved his hard dick deep inside her as far as it could go. The most amazing feeling came over him as he felt her tight pussy wrapped completely around him. He moaned loudly and without a moment passing started to ram his dick into her, her ass shifting along the desk as he pounded over and over again.

"Oh god," she held onto his shoulders and dug her fingernails into his back, swallowing hard as she wrapped her legs around his waist.

When he'd had enough of that he pushed her back onto the desk and climbed on top of her as he'd originally planned, allowing him better access to her. He kissed her on the mouth for the first time and let his tongue battle with hers for control as he pounded her harder, grunting.

Suddenly he felt her inner muscles start to clench around him. He couldn't believe his luck. Was she actually going to cum? It felt like someone was milking everything out of him, tight as a vice, but in the best way possible. He started a trail of kissed from her mouth down her neck, and pushed her clothing aside to try and get at her breasts, but he couldn't. He couldn't pay attention to that when he had to move faster and harder in and out of her. She was begging for it.

"Oh god, yes, fuck me!" She didn't know where the words came from, but there they were. She picked her hips up and tried to meet him thrust for thrust as he she felt him swell inside of her. It was the most complete feeling she'd ever experienced and just as she was about to ask for more her body gave it to her.

His thrusts pushed her over the edge and she started to come, her body clenching and freezing as she shook with pleasure. He couldn't take much more and the feeling of her coming all around his dick caused him to explode deep inside her. He collapsed on top of her, panting and trying to catch his breath.

"That," she said, her chest rising and falling quickly, "Wow.."

What more could any guy want to hear? Maybe that she wanted to go at it again, but the bell rang. "Fuck," the both said and started to get up. He pulled his pants back up and she reached for her panties, pulling them back on. She gathered her things and quickly ran for the door. What would people think seeing that she disappeared into his room so long ago and was just coming out now? She winced at the thought and headed for the door, "Bye mister Wilson, I'll um...I'll see you tomorrow...I guess?"

"Thanks, Jenny. That was just as great as I'd always imagined."

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