Jasons Education Pt 01

This story makes most sense if you first read the "Winter Getaway" series.

Jason looked at his watch to check the time as he drove. He had a sandwich in his free hand that he tried to wolf down without spilling any on himself or his truck. It wouldn't be the end of the world if he did. His clothes were covered with construction dust, sawdust, and other random solvents that had spilled on him during the day. He was beat from a long hard day at the job site. The phone rang. It was his friend Eric and it went on speaker. Eric was his childhood friend and the two of them had stayed close over the years, even working the same construction site together.

"Tell me. What's happening?" said Jason, between bites of his sandwich.

"Did I forget my tools?" Jason asked.

Eric was blabbering about something he had read online. Jason didnt listen to half the stuff Eric said. He was the kind of guy that conspiracy theory sites were catered to. After he was done blabbering, Jason sighed and asked "What is it now? Porn?"

"No, Im serious. You've got to read this. Let me send you a link."

Jason's phone dinged.

"Eric, Eric, stop. I dont need you to send me porn. Jeez..." said Jason, getting annoyed.

Eric had a nervousness in his voice. "Are you still in touch with Julia?"

"Julia?" asked Jason and replied, "Now, that's a name I havent heard in more than 10 years."

Eric cleared his throat and asked, "Did she ever call you pencil dick?"

Jason said "Dude, what kind of prank is this? Get the fuck outta here. Are the guys recording this or something? What has gotten into you?"

Eric was a little confused. "I don't know, man. I could have sworn it was about our Anna and Julia. I'm sorry. I shouldnt have assumed."

As soon as the call ended, Jason pulled off to the side of the road. He took his phone out, his hands barely able to hold it. His hands were shaking so hard that he looked like he was having a seizure.

Jason clicked the link and read "Winter Getaway." All three chapters, one after another as the traffic whizzed by. By the time he got to the third chapter, his heart was pounding so hard that he thought that he might be having a heart attack.

There it was. As Anna's husband was pounding Julia, she was spilling the story of how Anna had taken her shirt off and let Jason touch her boobs. Jason had touched Julia's boobs once before then, but Anna was this older 22 year old and it felt so surreal to touch her full, ripe melons. Anna had asked Jason to take his clothes off and had put his throbbing dick in her mouth. She had gently pushed back his foreskin and slowly sucked the tip of his head. She rotated her tongue around the tip of his head a couple of times, then taken his penis deep into her throat once before letting it go.

Jason had never masturbated. When he was younger, he had overheard some of his friends talking about how masturbation will deplete all of your cum and then there would be none left. He didn't know whether to believe them but decided to play it safe. It also meant that an eternity of cum had been stored up in his balls.

Anna had been busy explaining some technicality about giving a blowjob to Julia, when a steady stream of thick, gooey precum had started oozing out of his dick. He had tried to get Anna's attention, but it was too late. By the time she realized that he was about to cum, he felt a tightening at the base of his cock like he had never felt before. "UHHHhhh...uhhhh.....uhhhhh....." Jason said raspily before showering Anna's face with his cum. At first, it was a series of thick ropes that streaked across her cheeks and eyes, but that was just the start. It was soon a torrent of cum, splattering Anna's face in its entirety.

Then, what happened next was not in the literotica story.

Jason had been stunned, and a little ashamed. "I'm sorry, Anna. Oh God! I'm so sorry," cried Jason trying to rub his cum off of Anna's face with his hands, but it only made it worse and made some of it go into her mouth. The whole scene had been so erotic that Jason ramped up to another orgasm, cumming again, this time dribbling Anna's tits noisily with his second cum as his back crunched forward like a dog, and his hands still stickily holding Anna's face.

Jason had stepped back and frozen.

Anna had finally opened her eyes after wiping the cum clean from her eye lids. She looked down at her tits to see cum sliding down to the tips of her nipples and dripping down to the ground.

Anna finally looked up at Jason, who could not make eye contact. "Hot Damn, dude!" she had exclaimed.

She then peeled off her yoga pants and panties, and spread her legs apart to face Julia and Jason. She had rubbed herself furiously and within a minute, she was grunting and cumming. She was still covered with Jason's cum.

Jason wondered if Julia purposely avoided telling Anna's husband that part of what happened.

Jason snapped back to the present and looked down past the steering wheel of his truck to the bulge in his crotch. He gently unbuckled his work jeans and pulled out his pencil thin cock. He had never gotten over his fear of masturbation, and whenever he was turned on, it didn't take much to get the plumbing to fire up to maximum. The tip had become bright red and even without any stimulation, it started to profusely ooze precum. He touched his dick and moaned before going rigid. It took him only a second or two before he was spurting. He got a couple of gigantic splashes on his own face, and the rest landed on his steering wheel, stickily sliding down and dripping noisily to the floor of his truck.

Jason sighed. He had worked so hard to get all of those sexual thoughts from that time of his life out of his head. Here he was, back where it began.

Jason sat in his truck, covered in his own cum as he thought back to that day. Julia had made it seem like a single erotic incident to Anna's husband, but it had been the start of quite a wild ride for Jason.

He had put his clothes back on and had ran back to his house. He had opened the door and run into his tomboy of an older sister, Nicky.

"What's the hurry, bro?" she had asked. He didn't answer her and rushed to his room. As soon as he closed the door, he had roughly pulled his own pants down again and touched his dick gingerly. It throbbed. He gently stroked it once and it twitched. His butt clenched tightly and his tummy sucked in...and he then blew another load, noisily grunting and spraying the floor of his room with his third cum in just an hour.

Jason was shocked by how his body was reacting. He had expected to feel that way about his own girlfriend, Julia, but she had been a shy, inexperienced 18 year old who didn't know what to do. Anna on the other hand was this suave 22 year old who had absolutely dominated him and yet, made him feel good. He felt guilty and turned on at the same time.

Jason switched off the light to his room and got into bed. After what seemed like days, he heard a knock on the door. It was Nicky saying that dinner was ready. Jason mumbled back, "I'm not hungry tonight."

A little while passed and he heard another knock before seeing the door open and light spilling into his room. "Honey," his mom said quietly, "Is everything ok?"

She turned the light on and walked towards him and suddenly stopped a couple of feet from his bed. She looked down at her feet. Jason realized that he hadn't bothered to clean up and had left a sticky mess on the hardwood floor.

Jason's mom looked back up without changing her expression. "Do you want me to fix you some soup if you're not feeling well?" she asked.

"No, mom. I'm just really tired. I'm not sick or anything. Thanks, though," Jason said.

His mom planted a kiss on his forehead, before leaving the room. Jason's heart was pounding as he looked down at the floor. He saw the puddle of white liquid, with a smear on one end where his mom had stepped in it. Perhaps she didn't realize it and that posed another problem of whether she would be tracking it all around the house. Jason didn't have to wonder for long. Jason heard the faucet in the bath quietly turn on as he heard her scrub her feet. She knew! She was just being kind and letting him save face!

Jason just wanted to sink down through his bed and down into the ground below where nobody could ever see him again. The next morning, he called in sick at school. He waited to hear his mom's car turn on. He then waiting a little longer until the front door slammed as Nicky left for work. He then scurried down like a rodent and fixed himself breakfast. He spent the day mostly in bed and made sure to make himself a late lunch and retreated to the darkness of his room before his mom and sister got home.

"Dinner's ready!" yelled Nicky.

"I already ate," replied Jason.

"What's going on with him?" Jason overheard his mom asking Nicky.

After dinner, Jason heard a couple of impatient knocks and both Nicky and his mom barged in.

"This is an intervention," huffed Nicky, "Whatever is going on, you need to get up and engage with the world a little bit. We're going to watch a movie in a bit and all you need to do is come down to the living room and sit and watch with us. No questions asked."

"Oh, and take a shower before you come downstairs. You smell like stale teenager," said his mom, scrunching her nose in disgust.

Jason dragged himself out of bed and moped into the shower. He was half glad that his family had forced him out of his funk. The hot shower made him feel a lot better and he padded down the stairs wearing a clean T shirt and boxers. Nicky and his mom were already on the couch and flipping through the Netflix options.

"How's Julia?" asked his mom.

"Oh, she is good," replied Jason.

"We were worried that the two of you might have broken up," said Nicky.

Jason laughed nervously and replied, "Oh, not at all. She is the sane sister, believe me!"

"Sister?" asked Nicky with a puzzled expression on her face, "What's going on with Anna? Is she in trouble?"

Jason had forgotten that Nicky and Anna were the same age and know each other.

"Nothing. Let's watch the movie," said Jason.

Silence. Two pairs of eyes were now boring into him.

"Out with it, mister..." said Nicky.

"Nicky, take it easy on your brother," said Jason's mom.

Jason sighed and took a deep breath. He tentatively looked at Nicky to see if she would make fun of him. He saw her eyes soften with kindness. He recounted the struggles that he and Julia had had when they tried to fool around for the first time. Nicky stifled a laugh when he described how Julia had bitten him by accident. "I'm sorry," she said. "Go on. Don't mind me."

Jason then described how Anna had offered to help them out. Nicky looked up surprised and then made eye contact with her mom. Jason described how Anna had taken her top off and had allowed him to touch her boobs as Julia watched. Jason told them how he had felt that he was doing something wrong and taboo for feeling more turned on by Anna than by his own girlfriend. Since Julia was watching him, he had felt emboldened to reach out and touch Anna's boobs.

"Anna had these really sexy, full tits," Jason told Nicky and his mom, "Julia had nice tits too, but..."

"They are just boobs, Jason" said Nicky with a twinkle in her eyes. "That's what is making you mope around? Most teenage boys would be in heaven if they felt up their girlfriend and her sister at the same time. You're weird."

"Well...," Jason's voice trailed off. He did not want to tell his family what happened afterwards when Anna gave him a blowjob.

"It just feels awkward at first. Once you see a few boobs, you'll not feel head over heels every time you touch a new one," laughed his mom.

"You can see mine if you want," laughed Nicky and stuck her chest out at him.

Jason recoiled back.

"What? It's ok if it is Julia's sister, but not me?" laughed Nicky, loving the rise she was getting out of him. Jason sputtered.

She pulled her T shirt up until her boobs were completely exposed.

"Nicky, leave him alone," laughed his mom.

Jason was frozen in place. Nicky had very petite tits. They were barely an A cup, and her tits looked very different from Julia's B cups and Anna's C cups.

He knew that it was impolite to stare, but his mouth was open and he just stared at her chest. She had very prominent brown nipples and dark brown areolas.

"I know Anna has a big rack, but these are unique in their own right" said Nicky showcasing her chest with her hands making a Vanna White gesture. Here, do you want to touch them?

She scooted over towards him and stuck her bare chest at him. Jason looked at his mom, who shrugged. He tentatively lifed his hands up and reached over shakily to touch her. Jason was now getting turned on and felt his dick throb to life.

"What do you think, Jason?" asked his mom. Do you want a little more variety? Jason turned and looked at his mom, who had peeled her own top off.

"These are a little saggy, but that's because both of you sucked on them for a couple of years each," laughed Jason's mom, "What do you think?"

Jason turned and touched his mom's boobs. While they looked a little old compared to the teenaged boobs he had recently touched, there was a softness to them, and they were much larger than even Anna's boobs. His mom's nipples were also much longer and he couldn't believe that at one point he had sucked on them.

Jason's dick was now on full mast and tenting the front of his boxers. Every time his heart beat, his dick was lashing out at the fabric of his boxers and there was no way to hide it.

Jason cleared his throat and said, "Well, this wasn't the only thing that happened." Jason went on to describe how Anna had sucked him a couple of times until he had blasted his cum on her face and then again on her tits. He glumly told his sister and mom, "I haven't been able to get that image out of my mind. I don't know if I'm now a freak or something."

His mom's expression softened as she reached out and hugged him. She was still topless and her boobs pressed sensually against his arm. As she pulled back from the hug, she looked down at his crotch as his dick was straining against his boxers. There was already a small wet patch as his precum had started to stain the front.

Jason's mom sighed. She looked over at Nicky, who was intently staring at Jason's crotch. Nicky was topless and her nipples were stiff and engorged.

Jason's mom said, "I'm probably going to regret this" and she reached down and slowly lifted Jason's boxers over his boner and slid them down his legs.

She had never seen anything like it before. Jason had a thin, pencil like penis that wasn't much to look at, but the tip had turned an angry crimson color and a steady ooze of precum was welling up and over. She took a breath and then enveloped her mouth around her son's dick.

The taste of hot, salty precum immediately filled her mouth. She gulped as she swallowed the steady stream flowing out of her son's throbbing cock. She went deeper and deeper, until Jason's head was now pressing against the back of her throat.

If there was one advantage that Jason's mom had over Julia and Anna, it was experience. She had come of age in the 70s, and had experienced that heady decade and the free wheeling days before anybody worried about condoms and STDs.

Jason's mom opened her throat further and felt Jason's slender dick probe deeper down her throat. Then, she felt his dick buzz as his balls clenched tighter up towards his shaft. Then, she felt a rush of semen blast out of the tip of his dick that filled her mouth. Her eyes shot open wide. Well, this is different, she thought to herself. The pressure of Jason's cum as it blasted the back of her mouth caused her to choke and cough. She quickly swallowed most of it and got ready for the next onslaught. This time, her mouth filled up and she could no longer keep his sticky seed inside her mouth and it overflowed and dribbled down her cheeks and down her neck. She pulled his dick out, sputtering. Jason was not done, yet. His third squirt caught her squarely in her eye and she closed her eyes tightly.

"Oh, Jason," said his mom, "It's a little too much to handle..."

Jason turned and looked at Nicky, whose mouth was wide open in shock. She looked up at Jason and they made eye contact. There was a hunger in Jason's eyes that Nicky could not explain. She crawled over towards Jason, her tiny tits barely swaying underneath her.

Nicky had a strange expression on her face and she never broke eye contact with her brother. She kept looking into his eyes as she pointed Jason's pencil dick towards her face and away from their mom's plastered face. She covered the throbbing, angry dick with her own mouth and gently rubbed her tongue down the base of Jason's dick. Jason groaned as a third blast of cum flowed out of his dick into his sister's hungry mouth. She looked at him and gave a little moan as she felt the cum flood into her mouth. She took a huge gulp and swallowed the sticky mess in time to get the fourth blast. By this time, Jason was starting to wind down. Nicky withdrew her mouth, still looking into Jason's eyes. She kissed Jason's softening dick. She then turned and gave her cum covered mom a kiss on her cheek, causing the cum to string back and dangle between Jason's mom's cheek and Nicky's lips.

Awkwardness...

None of them wanted to make a move. This was not exactly how any of them had imagined the evening would turn out. None of them knew what to do next.

Finally, Jason jumped up and pulled his boxers back up. "I'm sorry, I'm so sorry, I'm so sorry," he cried.

Jason ran up the stairs and slammed the door to his room and jumped into bed. He didn't understand what was going on. Last week, he had been a complete virgin. In just 3 days, he had gotten blow jobs from his girlfriend, her sister, his sister, and his mom.

It didn't take long for him to drift off to a turbulent sleep. Answers can wait.