Learning Lessons 3 of 8: Caught in the Act // Chapter 4

Jess drove past the high school secretly hoping she’d see Tyler out in the field and then wished she hadn’t. He was there, he saw her, and he waved. She felt busted. And compelled.

She was on her way home from her school at 1PM and thought she might take the way around past Brady Byron, Geez, you never know you could just catch a glimpse of someone special. She had a half day, her kids went to a Spanish event with another class, some festival in Columbus and a lunch serving some authentic cuisine; she was going to catch up on some paperwork and thought she might as well do it at home.

Now she felt like this was going to be a big mistake. The turn signal was on before she knew it and she pulled into the parking lot. Tyler was running some boys, dressed in sweatshirts and sweatpants, but running with their football helmets on. It was pretty crisp out and she could see the clouds of their breath. She nosed the minivan into a parking spot right up against the chain link, the grassy field just on the other side.

Tyler stood and watched her, his arms folded across his broad chest. He was smiling. She smiled back for him, sitting in her car, watching. The boys ran past him again, their young bodies steaming in the cold. He encouraged them, slapped some shoulders. He was bundled up, looking massive in a tight sweatshirt with the Brady Byron Cougar, the hood bunched up around his thick neck. Still wearing shorts, even though it was late October.

The sun was shining but it wasn’t warm out there. It was one of the most beautiful autumns she could remember. So many sunny days, it was hard to believe winter was just around the corner. 

Tyler nodded his head to the side, towards the building. Come inside, come see me.

She knew she shouldn’t. She shouldn’t be seen with him. But she wanted to talk to him. She wanted to be near him. Frankly, she wanted to fuck him. She wouldn’t of course, not here. She should make a date. She should go in and find out when they can meet again. With Pete. Let’s do it this weekend. We will make it happen.

Now she was excited. This wasn’t some infatuated stalking incident. She was here with a purpose. She wasn’t messing around behind Pete’s back, she was here to arrange something. A time where Tyler could do it to her while Pete watches. Her life had become quite strange. She laughed as she undid her seatbelt and got out of the van.

The boys were running back into the gym, heading for the locker room. Tyler marched along behind them writing something down on his clipboard. 

Jess crossed the lot, went to the front doors, meant to pass through the admin offices like a visitor was supposed to then stopped short, her hand on the glass door ready to enter. The place was quiet, everyone in class at the moment. She changed her mind, walked down to the end of the building and came in through the side, into the double doors that lead to the stairwell. No one saw her. The halls were quiet, the only noises coming from the classrooms on either side of her. She felt suddenly very wicked. She tried to shake it off. She’d walked into this school a hundred times. She wasn’t here for anything dirty. Just here to talk to a friend. Something within her, however, wanted her to keep this a secret.

Tyler was at the end of the hall now, he held a hand up to her, watched her come to him. She looked down at what she was wearing. Conscious of her demure garb. Was she attractive to him like this? Her hair was up in a bun, she was wearing her big, black-framed glasses. Her skirt was long, almost right to the floor. She had a cotton shirt with a Victorian collar, buttoned right up. God, she was wearing a cardigan. He watched her the whole way down the long hall.

“Hi,” he said as she stepped up to him, not too close.

“Hi,” she said back, she couldn’t help her smile spreading wide.

Tyler held the door for her, and she walked into the teacher’s lounge. He followed her in. The place was empty, they were the only ones in there. She had her back to him, bit her lower lip, this felt like a big mistake.

“How do you take your coffee?” he asked her.

“Black, one cream,” she said, getting the nerve to turn to him.

He poured two mugs full of black coffee, added a splash of cream to one. He was smiling, confident. Looking over at her then back down as he put the cream back.

“I’ve missed you,” he said. 

She looked around, felt nervous even though she knew they were alone.

Tyler leaned back against the counter the coffee maker sat on. He looked really good. Too good. A cartoon ghost loomed over his shoulder, its big sad black eyes watching Jess. Reminding everyone else that there was a Halloween Dance this weekend.

She said, “I’ve missed you too.”

He brought the coffees over, set them on the table. She sat down in a swivelling chair, looped a finger through the handle.

Tyler sat next to her, the chair squeaking under his weight. “I’ve been thinking about you.”

He made her blush and she smiled, looked away. Looked into her coffee cup. “I’ve been thinking about you too.”

“You have?”

“A lot,” she said. She looked up at him, she was trembling. How honest should she be? Should she tell him she masturbated in a grocery store bathroom yesterday? That she had to run in there and get it done after thinking about what it would be like to feel him come inside her. She couldn’t—that was too embarrassing.

He sipped his coffee while he watched her play with her cup. There was a bowl of Molasses candy in the centre of the table and she pulled it over, took one out and fiddled with the orange wrapper.

“Were you in trouble?” he asked her.

“Yes.”

“It’s okay?”

“Yeah, it’s fine now. We can have sex,” she said, looked up at him, reassuring him, “he was… we made him feel left out. He didn’t like that.”

She could sense him nodding next to her.

“I’d like to see you again,” she said.

“Yeah?”

“You know, have you over for dinner.”

He nodded some more. “I’d like that.”

“Can we do it this weekend?”

“I don’t know—”

“I need it this weekend,” she said, seriously, hoping to sound sexy, but she could hear desperation in her own voice. Maybe he found desperation sexy.

“Saturday?”

“I’ll make it work,” she said. She felt relieved. Relieved and then instantly anxious. Like a countdown had just been set. Happy it was going to be done but now she had to watch the seconds click dreadfully past while she was driven out of her mind waiting.

“Pete’ll be there, right?”

“Oh, yeah. He wants to keep an eye on me now. Keep an eye on us.” She smirked, still fiddling with the candy, watching it in her fingers. “You’re still okay with that?”

He looked at her over his coffee, inhaled deeply. “I’ll take you whatever way I can.”

She blushed again, looked away. She tossed the candy back in the bowl, didn’t want him to think she was a fidget. She sipped the hot coffee, swivelled her chair to face him.

Tyler was leaning back in his chair his legs stretched out in front of him, one over the other. His big tattooed fingers circled his mug, and he looked out over it at her with his light blue eyes.

He got her fidgeting again, spinning her chair in circles, back and forth in tiny movements, making it creak.

“How do you hide that thing in those shorts?” she asked him. She thought his bulge would be huge the way he was sitting.

“It’s not always hard you know.”

She laughed, covered her mouth with her hand.

Tyler pulled his shorts up tight, spread his legs a bit for her. He got the front of his shorts up against his package, presented it to her, showing her his impressive shape under the fabric.

“Okay,” she said, “I’ve just never seen it when it’s not hard.” 

“It’s smaller,” he said. Then he thought about it a moment, rolled his chair next to hers so that their elbows were touching, both of them with their backs to the door. He stretched out the waistband, pushed the shorts out so she could see inside.

Jess leaned into him, curious, peeked into his shorts to see what it looked like. His sleeping cock was curled up in his lap like a pale banana.

“That’s not small at all.”

“Small-er I said.”

Jess put her hand into his shorts, she wanted to feel it. It was soft and surprisingly cold under her fingers.

“That’s really big,” she said. She rolled the head of his cock between her thumb and forefinger, ran her tips down his shaft, then wrapped her fingers around it, lifted it off his leg. She tried to stroke it but it wanted to slip out of her hand. She reached down between his legs and grabbed his balls. They were loose, heavy in her grip.

She looked back at the door, pulled his flaccid cock out of his shorts. She looked back down, looked at his thing in her hand. She lowered herself to it, put the head past her lips and sucked on it. It felt so funny in her mouth. Soft and squishy, squirming around, but just so darn big. She sucked it in deeper, liked the feel of it on her tongue. Tyler’s hand rubbed her back. He smelled like a powerful deodorant soap.

She used her fingers and tried to stuff as much of that soft meat in her mouth, couldn’t get it all in there. She picked a ball up and popped it in her mouth instead, sucked on it, rolled it around and let it drop, then back over the end of his cock. She thought about his cleanliness. She didn’t really know him. Didn’t know his past, kind of assumed he might have been with a lot of girls. But he wasn’t hard, nothing was going to come out of him, right? Like sucking on his finger. She sucked on him more, the soft thing starting to take some shape in her mouth, getting more workable. She gripped his balls, played with them, bobbing her head on his soft, heavy cock. She pulled off him, letting a loud suction from her lips. She had to stop, he was getting hard and she didn’t want him leaking in her mouth.

She picked it up, stroked it, using her spit. “I can’t wait for Saturday,” she said, got herself close to him.

“I can tell.” 

“Tell me what you’re going to do to me.”

“I’m going to bend you over, fuck you from behind like an animal,” his voice was breathy but deep, like a rumble.

“Oh, yeah?” she gasped, she had soaked her panties, she could feel it down there.

“I’m going to make you scream, I’m going to make you come a hundred times on the end of this cock.”

“Oh, God,” she looked down at it in her hand. He was pretty hard. Too big to be real. She couldn’t believe he’d been putting this inside her. She stroked him, her fist just working his head, rolling around it, squishing it.

“I’m going to make Pete shrivel up and die when he sees what I do to you, how I make you come.”

“He’s not even a tenth of the man you are,” she whispered to him.

“Oh, stop, stop, stop,” he said. He wrapped his big hand around her little wrist, stopped her stroking him.

“I can’t hide it if you make me hard.”

“You are hard,” she said.

“Mm. I am,” he said. He held her wrist tight, fucked her fist gently, doing it with his hips. They both watched him force her little hand apart, pushing his manhood through her grip.

“I can make it go down for you,” she whispered, looked into his eyes.

Tyler chewed his lower lip. “Come on,” he said.

He stood up, pointed his cock upright on his belly, pulled the strings of his shorts cinching it up against him, dropped his sweatshirt over it. He looked at her.

She nodded, she couldn’t see it.

He opened the door of the lounge, looked down the hall, “Okay, let’s go,” he said, waving her towards him. She took her glasses off, put them in her purse, followed him down the hall, their movement ranging from suspicious, to stealthy, to normal. Quick stepping, slowing, ducking. He got her to the end of the hall, checked into the boys locker room. He nodded his head for her to follow him.

She couldn’t go into the boy’s room.

“I can’t go in the locker room,” she whispered, still standing in the hall.

“My office is through here. It’s empty. Come on.”

She looked around nervously. This was crazy.

“Okay,” she said, slipping in behind him.

They rushed through the locker room, the place stinking with boy smell. Open lockers, stuff strewn out, equipment, towels, she didn’t want to look around--like this was a private place even though it was empty. He stopped at the next room, some sort of conference area, tables and chairs facing a whiteboard with running plans. He looked around the corner. “Come on,” he said and he took her hand.

She could see an open office ahead, they were almost there.

He got her in, closed the door behind him. 

He turned to her, they were face to face. She pulled him to her, kissed him, he pushed her away, “Hold on,” he said.

He crossed the small room, went behind his desk. There was a door on the other side and he opened it, looked out. Daylight out there, out onto the field probably. He looked around, watched something out there for a moment, then he shut the door said, “Okay,” pulled up on the bar, locked it.

Jess grabbed the handle of the door they’d just come through.

“This door doesn’t lock,” she said.

“Come here,” he said, standing behind the desk.

She went around behind it, let him pull her to him with his massive arms. He crushed her against him, she could feel his cock under his sweatshirt, hard against her body. He kissed her, gripped the back of her neck, pulled her tight, and forced his tongue deep into her mouth. She sucked it in.

Jess pulled her long skirt up, got her hands under it, hooked her thumbs into her panties and slid them down. She picked them up and threw them in her purse, didn’t want him to see them, they were a bit worn, definitely not sexy.

His hands went up her skirt now, bunching all the extra fabric around her waist. His touch was amazing. He went straight between her legs, not time for teasing.

“Oh, shit,” he said, “you are so fucking wet. Jess, you’re dripping.”

She had her hands under his sweatshirt her hands running over his rock hard stomach. She could feel his erection like hot steel against her wrist.

“Get a condom,” she said. She had no tome for teasing either.

“You don’t have a condom?”

“Oh, please, no. Tyler, why would I have a condom? You don’t have any condoms?”

“I don’t have sex at school.”

“Well, I don’t either. Don’t you put one in your wallet?” She was panicking.

“It’s okay, Jess, sit up on the desk here, I swear I won’t come inside you.”

That made her tingle.

“Oh, Tyler, I can’t.”

“C’mon, Jess, I swear I’ll pull out.”

She didn’t want to say it was more than that, didn’t want to ruin the mood by saying she wasn’t sure where he’s been, how clean he was.

“I just can’t, Tyler.”

Tyler grabbed the back of her neck, gripped a handful of her hair that had fallen out of the bun, he said, “Jess, I have to fuck you.”

“I need you so bad right now,” she said. She stroked him, felt how ready he was in her fist. She could barely close her fingers around it. “Oh, Tyler, I need this so bad.”

He lifted her up and put her on his desk, yanked her skirt out of the way. He lifted her like she was weightless.

“I just can’t, Tyler,” she whispered into his ear.

Tyler’s big hands pushed her thighs apart and she let him do it. Her soaking wet sex was exposed to his big manhood. He kissed her again, she put her arms around his neck. She felt his cock hot against her thigh. It was sliding up, getting closer to her heat. Her pussy ached for him, she would risk it, he could bury that naked cock deep inside her, she could find out what it really felt like. It would feel amazing. She knew it would feel amazing. He could pull out. What was the worst that could really happen?

She felt his hot tip at her labia. She opened her legs for him, leaned back so she could watch his unprotected cock slide inside her.

“Oh, baby, we shouldn’t,” she gasped but her legs didn’t close.

He gripped it in his fist, stroked the tip against her.

“No, Tyler, don’t. We shouldn’t,” she said but still her legs stayed spread. She wanted it so bad.

“Just the tip,” he said.

“Okay, just the tip,” God she was fifteen again. 

He pushed gently into her, struggling not to lose control and plunge it deep. She watched the glistening head, rosy-grey, part her lips. Heard the wet crackle as he penetrated her with his huge glans.

“Oh no, no, no,” she said. She grabbed it, stopped it form sinking into her. “I can’t Tyler, I can’t.” She closed her thighs on him, arched her back so her sex was flat on his desk. Her fingers were working the buttons of her shirt, moving through them one after the other. She got her top open, got her arms bent behind her working under her shirt, unclasping her bra.

Tyler watched her, stroking himself. His face was taut, angry. He had one thing on his mind.

Jess plopped herself down into his chair, gave him her best sultry look. She wanted her man happy. 

“Let’s make you come,” she said. Her fingers danced around her hardened nipples, thrilled them, showed him how aroused she was. She pushed her breasts together, let him know what she was thinking. “Come here,” she said.

He stepped forward, straddled her legs that she had kept closed together. His cock loomed over her, threatening. He was ready to burst. So hard his skin was stretched taut, his cock head gleaming. She put a hand over the wide top of it, guided its hot belly between her breasts. Enormous. Balls below her breasts, tip coming up past her chin. It didn’t work as well as she’d hoped. They were both dry. She worried about pleasing him. She spit on the head, took it in her fist and covered it. She squeezed him, coaxing some of his lubricant from him. He closed his eyes, let it pulse. Now she had him slippery, it was going to be okay. She pushed him down between her breasts again, she pinched her nipples, closed her flesh around it. He started to thrust it between them, slowly at first, testing the feel of her. 

“That’s it, baby,” she said, “fuck them.”

She had him breathing heavy now. 

“Show me that body, baby,” she said. He pulled his sweatshirt over his head, threw it aside. He was gorgeous. She watched his stomach ripple as he worked himself between her breasts. Watched the big glistening end come up to meet her, slide back down and disappear between her breasts. His huge tattooed atrms came to her, his hands gripped her small shoulders, held her steady. 

“You dfeel so good,” he moaned.

“You like fucking my tits?” she asked him.

“You’re going to make me come,” he said.

“Are you going to come in my face?” She looked up at him, her eyes expectant, she was play-acting but God, she was just so aroused too. She wanted him to come, wanted it to be huge and hot.

“Mm—yes,” he said, he was so close.

She had him in a trance now. Hard and horny.

“Do it,” she urged, “come all over my face.”

He got quicker, he was going to come.

She prayed he didn’t get it in her eyes or in her hair, but she did want him to come, wanted to hear him roar out because she had done it to him.

“Show me that come, make this big thing shoot all over me, make me—”

The door opened, three people walking in from the conference room.

Before she dove, before she threw herself flat on the floor she was aware, not sure, but had an awareness, that it was two students and a teacher. It happened very fast.

Someone gasped, someone said, Oh my God.

The door to the outside was opened, daylight hitting her in the face, making her blink. Tyler above her, shoving the door open. His shoe was kicking her in the behind, forcing her out the door. She alligator-crawled, fell outside the lip, down two steps onto concrete. The door slammed behind her. She was sitting by the football field. Her purse was still in there. Her glasses. 

Then she jumped up and ran. Ran in a straight line away from the building. Towards the woods. Ran faster than she ever had in her life. Legs pumping until she though her heart would burst. Fifty yards, across grass, students on the field, far from her, not looking. She got to the edge of the field. Houses, suburbs beyond that. Woods, trees. She launched herself onto an eight foot tall chain link fence, pulled herself over it, fell to the other side.

She looked back, saw the school, saw the door she’d come from. It opened. A woman. Angry, looking out and around. Jess rolled herself under a shrub. Her heart was pounding, her mind racing. What the fuck had she just done? Her heaving breaths became sobs as the realization came over her. This was real. This really happened.

“Oh, God,” she sobbed. “Oh, no.” The door closed again and she jumped up. She was in someone’s backyard. She ran down the side of the house, tears streaming from her. She buttoned her shirt as she ran, her breasts swinging around underneath it without a bra.

“Oh, no, oh, no,” she cried. She ran down the sidewalk, didn’t even know where she was going. She was going to lose her job. What would Pete think? What about the rumours? What would the boys hear about their mother?

What was wrong with her?