Risky Obsession Ch. 03

"That was some fuckin killer weed," Charlie said as he sprawled out on the couch and stretched his arms. The comment woke Peter who was on the opposite sofa. He rolled over with his eyes still closed.

"Dude," Charlie repeated, looking over at Peter.

"What?" he responded, eyes still shut.

"I said that was some killer weed."

"Mmm hmm," Peter said, dismissively, unwilling to engage in conversation just yet.

Charlie suddenly burst out laughing. This caused Peter to finally open his eyes and look over. "What?" he asked.

"Your fuckin dong is out!" Charlie blurted out as he laughed uncontrollably. Peter frantically looked down to see his penis head poking out under his boxers that had ridden up as he slept. He urgently tucked it back in. "Jesus," he muttered to himself before joining Charlie in laughing. "Fucking thing."

"Legit never knew you had such a huge one, dude," Charlie said. "When you got cut the other day.. Cynthia was probably like 'what the fuck'?"

Peter replayed her reaction to him ejaculating on the patio late at night. If only Charlie knew what had happened. "I guess," he responded humbly.

"How big are you hard though?" Charlie asked, never one to shy away from awkward conversations.

"Huh?"

"Your dick, dude. When you're hard it must be a foot long."

Peter closed his eyes again. "I dunno, man."

"Bullshit," Charlie laughed. "You know exactly how long it is. If I had that, I'd be proud of it. I'd have pictures of it up on the fridge."

Peter turned to him and smirked. "I am proud. Believe me."

Charlie laughed again. "You fuckin' dog, bro. Let's go upstairs. I'm fuckin' starving."

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"I'm gonna pretend I didn't hear that," Cynthia said, smiling. "I am the most senior person in this room. Someone needs to tame you guys!"

Charlie had just told another off color joke as the three boys and Cynthia sat around the kitchen table drinking coffee and eating pastries. Despite being twenty years old, Charlie still acted like a teenager sometimes, often unaware of his audience when going on a comedic tangent.

Kevin remained mostly quiet, having a bit of a hangover from the night before. Peter joined in on the jokes, making sure to steer Charlie back on track for the sake of everyone else.

"Oh yeah, Charlie. I'm sure she's definitely going to respond to you," Peter said sarcastically, referring to a girl that Charlie certainly left unimpressed with his antics. He smiled around the room, landing on Cynthia as they two made eye contact. She responded with a warm smile and a glimmer in her eyes.

Her beauty even in the morning with no makeup was unrivaled. Peter had always found her attractive, even as a young boy. But after last night, the two had a newfound connection that he could not take his mind off. His heart raced at even the slightest interaction with her. They had a secret. An unlikely encounter had left them in a unique predicament. But Peter loved it. He smiled back at her.

"I'm going back to bed," Kevin said, rubbing his temple.

"I'm going to Jane's house," said Charlie, clearly facetiously as he had just finished telling a story of his failed attempts at courting her.

Kevin retreated to his bedroom while Charlie went downstairs to gather his things. Peter and Cynthia were left to clean up breakfast together. Once they were safely at the sink with the running water, Cynthia playfull elbowed Peter. "And how are you feeling this morning?"

Peter checked the area to ensure no one was around. "I'm good. I feel refreshed. You?"

Cynthia nodded as she scrubbed a plate. "I'm good, thanks. You probably slept well huh?" As she cleaned the plate, her large breasts bounced under her t-shirt. Peter could see that she wasn't wearing a bra. His cock lurched at the glorious sight. He nervously laughed. "I did sleep well."

Cynthia crept up closer to him so that her left breast was touching his arm. Peter didn't protest as he continued to go about cleaning dishes. "I've never seen a display like that," Cynthia whispered. "You came so much!"

Peter stopped what he was doing and smiled down at Cynthia. He was about six inches taller than her. "That wasn't even my record either," he said slyly.

"My goodness. You have some serious gifts, Peter." She pressed even closer to him, this time reaching over and rubbing his thigh. "Some very serious and big gifts," she repeated.

By now, Peter was sprouting an erection, plainly visible through his shorts. Cynthia eyed it and smiled. She tapped the head of his protruding cock with her finger. "Good morning, sir," she said teasingly. She and Peter laughed together.

"Is there any more coffee left?" a deep voice from the other side of the kitchen emerged. Peter immediately recognized it as Cynthia's husband and Kevin's father, Frank. While Cynthia carried on washing dishes, Peter froze in place. He had an aching erection and was about to have a very uncomfortable encounter.

"On the table in the carafe, honey!" Cynthia called out. Peter pretended to be preoccupied washing a plate that was blatantly already clean.

"Kevin's friends are actually doing something useful around here?" Frank asked as he poured himself a cup of coffee. He had a way about him that it was difficult to tell if he was actually joking or not.

"Gotta do my part somehow, Mr. Myers." Peter couldn't turn around as he still sported a sizeable half erection.

"I didn't even hear you come home, honey," Cynthia said.

Frank sat down at the table, crossed his legs and opened the newspaper. "I came home late last night. Flight kept getting delayed over and over again," he said without looking up from the paper. Peter carefully watched for Cynthia's reaction, but she didn't seem phased by the conversation.

How late is late? Peter asked himself, as he frantically replayed the events of last night, unsure if he had been caught.

Frank was a mysterious character around the house. Peter and Charlie barely knew him as he traveled so much, but his large frame and deep, commanding voice often left them feeling intimidated. If he had seen what happened last night, Peter didn't know what he'd do. He admitted to himself he would have to fight. Not just Frank, but maybe Kevin as well. This would not be good. The fear and urgency of the situation allowed him to completely soften between his legs, enough that he could now turn around. Frank still didn't look up.

"That barbecue place on Pleasant is already gone," he announced. "No one seems to survive that corner."

"It's doomed," Cynthia added.

"Doomed forever," Frank agreed.

Charlie emerged from the basement. "Welp. I'm hittin the dusty trail folks. Oh, hey Frank, didn't know you were home." Frank ignored Charlie as he continued to peruse the newspaper.

"Yeah I'm gonna get going too. Thanks for letting us stay here last night," said Peter.

"So soon?" Frank finally looked up. "Was it something I said?" He looked at Peter square in the eyes. He had not even flinched when Charlie announced he was leaving, yet something piqued his interest. His gaze was punishing. Peter's stomach dropped.

"Uhh, yeah. I have to work... so..."

Frank turned back to his newspaper. Peter didn't dare look at Cynthia until he was well out of the kitchen and in the foyer. Cynthia followed shortly after. As Charlie headed for the car outside, she placed her hands on Peter's shoulders and smiled. "Relax," she whispered. "We'll talk soon."

Peter dashed for the car and jumped in. "You alright dude?" Charlie asked. "You look like you just saw a ghost."

"I'm good. Let's go," said Peter.

"Did Cynthia just give you a quick reach around?" Charlie joked as Peter glared at him.

Peter looked out the window as they drove off. "Do you think Kevin's dad is an asshole? He was being kind of a dick, right?"

"He's always been like that. Ever since we were kids. The guy has a giant stick up his ass all the time," said Charlie.

Peter couldn't help but wonder if Frank knew what happened on the patio. In the heat of the moment, the last thing he was thinking about was checking to see if someone was watching.

"Fuckin Cynthia's so hot, man," said Charlie. "Walkin' around without a bra. My God. You know what I mean?" he turned to Peter.

He smiled and nodded. "She's a smoke, for sure."

"Can't believe she saw you naked too. I guarantee you she thought about your dick. Thousand percent."

Peter didn't respond, opting to stare out the window instead. He had something else on his mind.

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Since his parents moved to Florida when he left for college, they didn't sell the house that Peter grew up in. Instead, they held onto it so he could stay there when home from school.

Peter jerked off constantly the following few days. He couldn't stop thinking about what happened and yearned for another opportunity with Cynthia. She told him they would talk soon, but aside from him returning to Kevin's house, he had no idea when that would happen.

One afternoon, he was lying on the couch playing with his cock watching porn when his phone vibrated. It was an unknown number.

"Hi"

Peter didn't respond.

"It's Cynthia."

Peter then stroked his cock excitedly before he typed back.

"Hi how r u?"

"I'm thinking about you sweetie," she said. "We should get together again soon. Not here tho lol"

Peter continued to jerk off. He was desperately horny and she wrote to him at the exact right time. "What are you thinking?" he replied.

"Maybe we can get a hotel or something" Cynthia typed back.

"That would be awesome. Tomorrow?" Peter replied, maybe a bit too eager. He didn't get a response. His confidence deflated. Maybe he was being too forward with his best friend's stepmom, after all.

Nearly fifteen minutes passed until his phone went off again. "You're cute. How about Thursday?"

Thursday was three days away. It would have to do. Peter responded with the thumbs up. Just as he was about to put his phone down, another message arrived.

"Send me something to look at until then."

It couldn't have been a better time to send a picture. Peter was throbbing hard. His dick looked perfect as he held it by the base, sprawled out on the couch. Precum leaked from the tip, traversing his bloated cock head. He snapped a couple pictures, picked the best one and hit send.

After only a few moments, he got a response.

"You're huge. You're amazing."

Peter smiled satisfactorily as he stroked his cock. He typed out a response. "I need to empty this thing now."

"Not there! You're going to ruin Sharon's beautiful couch."

The comment reminded Peter of who he was flirting with. This woman, although younger than his mother, knew her well. They went to the boys' sports games together. They served on the parent teacher council together. It was all so bizarre...

Suddenly, the moment arrived. Peter came fast and hard, squirting thick loads straight up into the air of his quiet living room. He moaned as he jerked himself off, shooting his cum in the air like a fountain. It came splashing back down on his belly and legs, coating himself in a familiar sticky white goop.

Afterwards, he laid there calmly, surveying the mess he made. He then snapped a photo of his deflating cock, resting on his belly surrounded by a massive mess of sperm. Without even thinking, he sent it to Cynthia.

Again, no response. Peter panicked. Did someone else have her phone? Why would she not respond to that? He tossed his phone aside and ran to the shower to clean up. As he scrubbed himself down, he thought about what he'd do if someone saw that message. Like Kevin or worse, Frank. He would have to just be honest and face the consequences.

He hurried back to the living room naked and unlocked his phone.

One new message. "Looks good enough to eat."

He breathed a sigh of relief as he plopped back down on the couch. Crisis averted.

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Cynthia and Kevin sat outside on the patio having dinner one night. As they chatted, Cynthia eyed the lounge chair behind Kevin. No more than a week ago, her stepson's best friend was stretched out on that chair jerking off in front of her. In fact, he had probably ejaculated close to where Kevin was seated at that very moment. She snapped out of it and turned to Kevin.

"How's work going?"

Kevin shrugged as he chewed his salad. "I cut grass. That's work."

Cynthia nodded. "Money's money, right?"

Kevin looked out across the pool. "I just wanna graduate and do a real job."

"You should work for your father."

"Oh yeah? And be gone 90% of the time on a plane to God knows where? No thanks." Kevin always dismissed his father's line of work. He hated that he never saw him and vowed to never get wrapped into a career like that. Besides, he enjoyed the time at home with just Cynthia. She was so easy going and things were far less stressful without Frank around.

"I agree. The travel part is hard. Money's good though," Cynthia commented as she pointed to their surroundings. The backyard was expertly manicured and the pool was modern and lavish.

Kevin nodded. He had thrown one too many parties at the house all through high school and afterwards. It was good to have a nice house, plenty of money and a stepmother he got along with.

Cynthia's phone buzzed. She ignored it as she poured another glass of wine. "That thing's been ringing off the hook. You starting a business I should know about?" Kevin asked.

She smiled. "Robocalls. They never stop." Kevin nodded in agreement.

"Hey listen," Cynthia started. "I'll be gone tomorrow night. Nurse's conference in the city. I'm gonna get a hotel with a coworker. Judy. You remember her."

"With the hair?" Kevin asked.

Cynthia laughed. "With the hair. But yes, just one night. Your father comes back the next night so we'll all be back together then."

Kevin nodded, although appeared disappointed. "What, so no movie night anymore?"

"Rain check?"

Kevin shook his head. "Unbelievable," he decreed facetiously.

"Have Amy over!" Cynthia suggested to which Kevin glared at her. "Meh," he said, uninterested. He was always hot and cold with his girlfriend.

"You'll be fine," Cynthia said as she grabbed his arm and gave it a soft rub.

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The hotel was well off the beaten path. Far outside the city center in an industrial park, the Courtyard Marriott was nondescript and only sparsely populated with business travelers. As Peter pulled in, he immediately noticed Cynthia's car parked in the back row underneath a large tree. He decided to drive around and park far from her car, just in case. His nerves were shaking. His heart didn't stop racing. He felt naughty and mischievous.

Am I gonna bang my best friend's stepmother? he thought to himself. Part of him worried he wouldn't be able to fit inside her and he'd never get another opportunity.

Shortly after just two knocks on the door, he could hear the deadbolt followed by the door opening a crack. "Come in," he heard from inside as he pushed the door open.

Cynthia was already headed towards the back of the room, carrying a wine glass. She wore a black summer dress and was barefoot. She turned back to him and smiled as he followed her. "Do you feel like James Bond?" she asked.

"Kind of!" Peter said, at ease from the opening joke.

"Have a seat. Pour a drink. Relax."

Peter grabbed a wine glass and helped himself. He didn't normally drink wine, but figured it was better to be classy tonight. He wore skinny jeans and a v-neck t-shirt that outlined his figure boastfully. He sat down on the couch, opposite Cynthia.

Cynthia crossed her legs and bounced her bare foot in the air. She smiled as she took a sip, never breaking eye contact with Peter. "You gonna whip it out?" she asked.

Peter was dumbfounded. "Really? Right now?"

Cynthia burst out laughing. "No, honey. I'm kidding. Relax. We're here now. It's safe."

Peter laughed. "Ok, but if you want to see it, you know you can. You probably have twenty pictures of it by now anyways."

Cynthia shook her head. "All deleted sweetheart. I enjoy the moment, but cover my tracks."

"Ahh, very smart."

"You know," Cynthia said as she switched which leg was crossed. "Frank can't ever find out about this. I'm serious. He can never know."

Peter became solemn. "Absolutely. I would never dare."

"Good," she said as she studied his face. She determined him to be trustworthy and a safe option for what they were about to do.

For the next hour, the two spent time getting acquainted. As good conversationalists, there was never a dull moment. Peter made her laugh with silly jokes. He was charming, funny, and seemingly more and more at ease. Cynthia migrated to the couch so they were next to each other. She propped her feet up on the coffee table and noticed Peter was checking them out.

"You like feet, huh?" she asked as she stretched out her painted toes.

"I like yours," Peter clarified. "They're slim, petite. Well manicured."

"Pedicured," she corrected him.

"Whatever," he laughed. "You have really pretty feet. In fact, all of you is very pretty. But you already know all this."

"Thank you, honey." Just then, Cynthia's phone buzzed. She picked it up so see a text message. 'I miss you.' She placed it back down without responding and focused all her attention on Peter. "Now, what do you say we see that penis of yours I hear so much about?"

Peter laughed as he put his wine glass down next to Cynthia's sexy feet. "Oh yeah?" he asked, reaching for his belt. "That's how this begins?"

"Sure is," she said, laughing, as she placed her glass next to his and got comfortable. "I'm so excited!" She clapped a few times.

"That makes two of us," Peter said before pulling his jeans down and sitting back down in his black boxer briefs. He then eyed Cynthia's bust line with a look of desire. "Do I get to see anything too?"

"In time," she reassured him. "Show me him again first."

Peter was very obviously hard as he tucked his thumbs under his waistband, delaying the reveal intentionally. He looked up at Cynthia whose eyes were glued to the massive tent standing up underneath. "C'mon!" she shrieked in excitement, like a young teenager who just had a first kiss.

He then proudly pulled his boxer briefs down. His heavy cock flung back with force, resting against his belly. Cynthia gasped as she studied its underside. "It's so big," she repeated like last time. "It's bigger than any man I've ever seen."

"You want me to jerk off again?" he asked. Cynthia didn't respond. Instead, she picked it up with her dainty hands. She began to stroke him herself. Peter moaned softly as he sunk into the couch. He spread his legs, revealing his heavy and full balls.

For several minutes, Cynthia rubbed him in silence. One hand rested on his thigh while the other did the work. "I can get two hands on you," she said as she now jerked him with both.

"Probably three," Peter estimated as they both watched her masturbate him. "Can you spit on it?" he asked.

Cynthia tucked her hair back behind her ear and leaned forward. At first, she had a hard time getting spit out. They both laughed at the insufficient amount that dribbled out. "It's hard!" she said as she caught her breath and got ready to try again. "Ok, ok, ok," she said. She then was able to spit a decent amount that dripped from her mouth down to his aching cock. She dispersed it with both hands. "How's that feel?" she asked.

"So good."

"Yeah?" she asked. "Good."

She continued to jerk him off as he moaned in delight. The imagery of her beautiful hands, dangling breasts, and blonde hair constantly getting in the way was sending him rapidly towards the edge. He even heard her moan tiny little noises every once and again. It was all culminating rapidly for Peter and he sensed he was about to cum.