Sharon's Little Plan Ch. 02

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Jason's situation only seemed to get worse and worse...
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Part 2 of the 2 part series

Updated 02/08/2024
Created 02/03/2024
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esthreals
esthreals
35 Followers

The past three days had been a nightmare for Jason. At first, he had tried to pretend like nothing was out of the ordinary. This failed almost immediately, as with every step he took, he was reminded of his unfortunate situation by the swinging hunk of metal in his pants. Taking a walk was uncomfortable, and taking a toilet break was a plain disaster. But this was nothing compared to his first night sleeping while wearing that infuriating chastity cage. Jason had woken up more times than he could count, greeted by an intense sting in his crotch. His cock felt like it was trying to burst its way out of its cage.

In short, Jason felt like shit. And he wanted to make sure his Mom knew that. The very next morning after that first hellish night, Jason had pleaded to no end to his Mom, trying to convince her that this was way too harsh of a punishment for those few minor things he had done. "I warned you that your first night would be a bit rough, Honey," Jason's mother had simply waved him off. "But I promise that it will be better tonight!" Sharon didn't seem to be moved at all by her son's miseries.

She had been right, though not by much. Only by the third night, Jason managed to sleep through it in one go. That morning was the first time that Jason felt like he would be able to live with this for now, as he was finally getting used to the chastity cage, slowly but surely. But apart from being able to live comfortably enough, there was another glaring problem.

"Mom, can I talk to you for a minute?" Jason called from the living room. He was lazing around on the couch watching TV, still wearing his pajamas as he had just woken up.

His mother walked into the room, also still in her pajamas. Jason couldn't help but admire her astonishing figure as she stood there in the doorway. She could make absolutely any outfit look sexy, couldn't she? Those curves were just to die for.

"What is it, Honey? Do you want me to make some breakfast for you too?" Jason's mom asked.

"No thanks, already had some", he refused politely. "I wanted to talk about something else with you."

Sharon's expression swiftly turned serious. "Is something wrong with your chastity cage, Hon? I thought you said that you finally slept well..."

"I know Mom, and it's getting better, but there's something else." To show what he was getting at, Jason stood up from the couch and pointed at his crotch. "How am I supposed to go outside, looking like this?" They both looked at the obvious bulge in his pajama pants. You could even see the outline of the metal ribs of the chastity cage.

Jason waited for his Mother's answer. Sharon opened her mouth to wave away another one of Jason's complaints, but she didn't have anything to say this time. "I- Yes, I think I get what you're trying to say", she finally conceded.

Gaining his first ground in three days, Jason immediately tried to capitalize on this. "It's not an option if I can't go outside anymore, right? How am I ever supposed to meet with friends, looking like this?"

"I know, Baby," Sharon gave in. "But-"

Before his mom could start her next sentence, Jason swiftly interjected. "Alright, so what about this: I'll wear this chastity cage thing whenever I'm home, but can we please take it off if I want to go out?" He had been waiting for the right moment to try getting out of this shitty situation and waited with bated breath for his Mother's response.

Unfortunately, Jason's Mom already had a plan of her own. "I don't think that's necessary, Sweety," she simply said, crushing her Son's hopes and dreams. "I've already been looking for a solution to our little problem here, and I think I've found something. Come with me", she gestured toward the staircase. Jason couldn't help but have a bad feeling about this, together with a sense of déjà vu.

***

"Tadaa!" Sharon presented proudly. They were in the same position as a few days ago, with Sharon sitting on the edge of the bed and Jason standing in front of her. Unlike that day, Jason had already dropped his pants without hesitation, putting his caged cock in full display. He didn't feel nearly as embarrassed, as his Mom insisted on checking up on his package every morning and evening. Even Jason himself was surprised that he was getting used to this bizarre routine.

"That was your bright idea?" Jason said exasperated, with a hint of anxiety in his voice. His Mom was now showing him another one of those chastity cages. This time though, it was a model made out of black plastic, with plenty of holes on the side and on the tip. Jason's problem with it was that it seemed smaller than the one he was wearing right now.

"It sure is!" Jason's cheery Mom responded, dismissing his sarcasm completely. "This will definitely solve our 'big' problem here, won't it Honey?"

Only then, Jason realized that he had fucked himself over once more. "Yeah, but..." Jason anxiously tried to come up with any excuse, but he was grasping at straws. "But I don't think it'll fit, you know? Like last time..." Jason tried, alluding to the fact that his Mother had to fight a tough fight to get his monstrous cock inside his current chastity cage.

"Oh, you don't need to worry about that. I think I've gotten the hang of this", Sharon tried to comfort her Son. "And now that our 'little' guy here has gotten used to a chastity cage, I think it won't be a problem," she speculated, as she gave a playful tap to the metal cage, making it swing side to side. Jason's cock wasn't bulging out of the cage anymore, but it was still filling it out completely.

Before Jason could come up with any other objections, Sharon was already retrieving the small key from the necklace underneath her pajama shirt. Jason was shocked when he heard the sweet sound of the brass lock clicking open, the lock that had taunted him for the past few days. It almost felt uncanny when the metal cage was removed, finally giving his dick some space to breathe.

Jason couldn't relish in his newfound freedom for long, as Sharon hadn't been lying when she said that she had gotten the hang of this. Before Jason realized it, his Mom had already changed the metal ring behind his balls for a new plastic one. After she swiftly applied copious amounts of lotion to his package, Sharon skillfully slid the new cage around his cock. To Jason's surprise, his cock hadn't grown an inch since being released from its cage. It made him a bit worried, and he had at least expected that putting on his new cage would be as horrendous as the first time.

This wasn't the case at all, though. Sharon only had to compress his cock by the small decrease in length between the cages. Before Jason knew it, he heard a familiar brass lock clicking shut once again. He stood there stupified, as his mom pulled up his pants.

Sharon nodded approvingly. "This is miles better than your old cage, that's for sure", she said. There was still a slight hint of a bulge, but that was to be expected. It was still one of the largest cages available, which was necessary to be able to contain Jason's massive cock. Sharon figured that the bulge would be even less visible if Jason wore his usual jeans.

"Isn't that great, Honey? Now you don't have to worry when you're going out!" Even though his Mother was elated, Jason didn't seem to be able to match her happiness. This wasn't the first of his plans that had backfired, and he was getting the feeling that it wouldn't be the last.

***

Sharon had been doing the laundry as usual, until she saw something in the corner of her eye that caught her attention. As she was sorting Jason's clothes, she noticed a subtle stain in Jason's underwear. She retrieved the piece of clothing from the sorted pile and looked more closely into it. After close inspection, Sharon knew enough. She had been expecting it, but it still took her by surprise. She felt her stomach tense up in anticipation. 'I guess it has already been a week, hasn't it?' she realized. Now that Jason had mostly gotten used to his chastity cage, he had encountered his new foe: sexual frustration.

Sharon went upstairs to go looking for her son after she had rushed through the laundry. Her heart was beating wildly in her chest, anxious to start the next phase of her plan. This had to wait for a bit, though, as her son was nowhere to be found. Sharon then remembered that a friend of Jason's had stopped by, so she figured that they had probably gone to the gym across town.

This put Sharon in a bit of a bad mood, as she was itching to talk to Jason. She impatiently sat down at the kitchen table, put a hand under her chin, and started tapping the table with her long nails. After doing this for a few minutes, she was thoroughly irritated by herself. She decided to go for a short jog, which would hopefully make the wait a bit more bearable.

Before that, Sharon needed to change into more suitable clothes. She was wearing a tight pair of jeans that perfectly highlighted her figure, but they would be impossible to run in. After changing, Sharon was posing in front of the mirror in her bedroom. She had swapped the pair of jeans for a pair of equally tight running leggings. She twisted and turned, propping up her butt, concluding that these leggings looked even better on her. 'Maybe I should wear these more often?'

Sharon had also changed into a sports bra, which could do a better job of keeping her boobs in place than her usual tanktop would. All in all, Sharon looked positively gorgeous at the moment, and she knew she would turn plenty of heads during her run. There was only one person whose head she was actually interested in turning, though.

***

Sharon came home sweaty and exhausted. She had accidentally taken the wrong turn somewhere, making her do the large loop around town instead of the smaller one she had been planning to do. She walked up to the front door with shaking knees, barely being able to stand anymore. She noticed that the door was open, indicating that Jason had already gotten home in the time that Sharon had been running around town. Once inside, Sharon walked upstairs immediately, longing for a shower to get rid of all the sweat.

She suddenly bumped into her son, who had just come out of the bathroom himself. He was wearing nothing but a bath towel, showing off his muscular upper body. Veins were popping in his arms, and muscles were bulging in his chest, as blood was still rushing through his body after an intense workout.

"Wow, looking good, mom!" Jason complimented her. "Had a good run?"

It took a while for his words to sink in, after which Sharon quickly tore her eyes off her son's chest. "Thanks, Honey. It was good, although maybe a bit too long." Her eyes now landed on his crotch, knowing of the caged monster that was hiding behind that towel. She could feel the excitement building in her stomach. "I have to say, you are also looking the part, Hon", Sharon unconsciously added.

"Oh?" Jason responded positively surprised. "You like what you see?" he teased, pushing out his chest.

"I do-", Sharon started, as her fingers reached forward, but she caught herself in time. She swiftly took a step back, creating a bit more distance between them. "Ahem, well anyways, now that we're both here," Sharon coughed while she avoided looking at Jason's smug face. "I needed to talk to you for a minute."

"Sure, Mom, go ahead", Jason egged her on. He made it clear that he wasn't planning on getting dressed in the meantime, and was shamelessly devouring Sharon's hot body with his eyes.

Sharon chose to ignore this, focusing on what she was about to say next. "Have you been feeling... sexually frustrated lately?"

This got Jason's attention, wiping the smug smile from his face. "What do you mean?" he nervously asked.

"Well..." Sharon hesitated. In the meantime, she noticed Jason's wandering eyes halting at her breasts. 'It can't be helped', she thought. Her glistening cleavage would attract the eyes of any man nearby. She then realized that he was staring at something else. Jason's eyes were locked on the small key pushed between Sharon's breasts, barely visible but still out in the open.

"Most men start to build up some serious sexual tension after their first week," Sharon continued. "And for health purposes, we will need to relieve some of it once every so often. Are you listening, Hon?" Sharon asked, wondering if Jason had heard anything she had just said.

"Were you wearing that necklace outside, Mom?" Jason suddenly asked.

'That is what he is worried about?' Sharon was dumbfounded. Boys worried about the weirdest things, didn't they? "Of course Honey, I wear it all the time", she proudly proclaimed. She fished the key from between her breasts and showed it to him.

Somehow, this made Jason even more displeased. "Do you really need to?" he asked, irritated. "Can't you like, take it off when you're going out or something?"

"Oh? And why should I?" Sharon returned the question, a dangerous tone in her voice.

Jason didn't seem to notice it, though. "Don't you think people will find it weird that you're wearing a key on a necklace? What if people we know see it?"

"Jason." Sharon cut off his whining, the tone of her voice downright dangerous. "I keep the key to your chastity cage on me however I see fit. If I wanted to, I showed it off to all our friends and family, proudly proclaiming what it's for."

Jason's face turned white at this threat. "But I don't", Sharon continued. "So consider yourself lucky." A silence fell between the two.

"Can I continue where I left off now, Honey?" Sharon finally asked.

"Sure," Jason grumbled in response.

"Alright, so as I was saying, we'll be relieving some of that tension every week, starting from today," Sharon announced.

"What do you mean, tension?" Jason asked, still playing dumb even now.

Sharon sighed. He really didn't want to play along today, did he? "'Sexual' tension, Hon. Have you noticed something building up the past week?"

"Not really, no", Jason denied, now avoiding his mother's gaze.

"Honey, I do the laundry in this house. I know you've been leaking in your underwear. Have you been having wet dreams at night?"

"Mom!" Jason acted offended, but the red flush on the tips of his ears betrayed him.

'He's like an open book', Sharon giggled internally. "It's perfectly normal, Baby, especially considering that this is your first time wearing a chastity cage."

"I never said I had any 'wet dreams', though", Jason stood his ground.

"Okay, alright, my bad", Sharon put her hands up. "I just figured that it would be healthy to release some of your sexual frustration about once a week. But if you say you're still feeling great at the moment, we can wait for a few more weeks."

Sharon saw Jason's eyes widening. She didn't need to, but if she played her cards right, she could get a little confession out of him. "Is that alright with you, Honey?" she asked innocently.

Jason hesitated for a moment. "Ehm, well, can we still do that once-a-week thing? It's not like it is really bothering me at the moment, but could we do it just to be sure, for if it gets worse?"

It was a feeble attempt, which Sharon easily parried. "That's not what we agreed on, Honey. I was only considering that for your health, as you can't keep holding it in if it is building up too much. But if you say everything is still fine, we'll just wait a few more weeks."

This was the final blow for Jason. "Okay, mom, you win. I probably did have a wet dream or something. I'm just too horny, you know?"

Sharon felt butterflies in her stomach. Hearing him say this out loud made her all hot and bothered. "I know, Baby. You know what? Let's ease that feeling right now", Sharon said as she grabbed his hand.

***

Mother and Son were once again in their usual positions in Sharon's bedroom. Jason only had to drop the wet towel to undress. Sharon had a tingling feeling in her stomach every time she saw that big monstrous cock of his, locked in its little container. She couldn't help but fantasize about taming it even more.

Jason held his breath as the chastity cage was removed, his cock free again. Like last time though, it didn't seem to be in a hurry to get hard. "Let's not make things weird, Hon," Sharon stated. "This is just something that has to be done for your health, okay?"

"Mm-hmm," absentmindedly agreed. He couldn't care less about Sharon being his mother right now. He was just too damn horny!

"Great! Let's first get you nice and hard, before we get to the main part." Sharon fished out a normal bottle of lube from her nightstand and got to work. For the next few minutes, she delicately spread it all over Jason's balls, along his shaft and the tip of his cock, using only her fingertips.

As if woken up from a deep slumber, Jason's cock finally started to rise. For the first time in a week, it slowly grew under Sharon's touch. Her eyes widened when it was finished, as Jason's absolutely massive cock proudly pointed up in the air, jumping at every touch. Sharon was getting wet herself from all the excitement, but a part of her still felt disappointed. 'I guess it didn't work...' she thought to herself, as she shot a glance over her shoulder toward her nightstand, where the tube of lotion was hiding. 'It's not like I used too little of it, anyway', she resigned herself. The tube was already halfway done in just the few times she had gotten the chance to use it.

Sharon decided to take her mind off it and let Jason finish, who was waiting impatiently in front of her. "I'll start slowly, Baby. Make sure to warn me when you're getting close, okay?"

"Mm-hmm", Jason nodded again. He hadn't heard a thing his mother had said.

Sharon slowly closed her slender fingers around the base of Jason's cock. She grabbed it tightly and started slowly making her way up to the tip. Once she reached it, Jason tried to push his hips forward, but Sharon pushed back against his pelvis with her free hand to stop him. "Let Mommy do the work, Baby." Jason let out a low grumble, but he did stop thrusting his hips.

After a few painfully slow strokes, Sharon added a second hand, stimulating Jason's glance as she stroked along his length. At this point, Jason started audibly moaning. Meanwhile, Sharon couldn't tear off her eyes from the monstrous cock she was stroking. Her mouth was watering, eager to try taking in its length. 'No, I can't...' she struggled.

Before Sharon could've made any drastic decisions, Jason let out a deep grunt and pushed his hips forward, sliding his cock one more time through both of her hands. "Fuck..." he moaned before he reached his climax. Sharon's eyes widened in surprise and she let out a squeal when the first spurt of cum spewed out of Jason's gigantic cock. It almost reached the ceiling, flying over Sharon's head and coating the covers of her bed. She kept holding onto the base of Jason's spasming cock as the second and third strokes shot right into her hair and covered her face. The last spurts sprayed all over her chest, staining her sports bra, covering her already sweaty cleavage, and dripping down her perfect breasts. To Sharon's great surprise, it had taken her a mere ten strokes to make Jason's massive cock absolutely explode.

After what felt like ages, the final dribble of sperm finally ended, leaving the room, and especially Sharon herself, completely covered. Jason had his eyes closed, enjoying the feeling of sweet release. Still holding onto his gradually softening cock, Sharon ripped Jason out of his post-orgasm bliss with a tone that could freeze the Sahara desert. "Jason..."

Jason finally opened his eyes and was shocked by the unbelievable mess he had made. His Mother's face looked scarily pissed off, but that was lessened by the fact that it was covered in cum. "This wasn't supposed to be for your enjoyment!" Sharon started her tirade. "You were supposed to warn me when you were close!"

esthreals
esthreals
35 Followers
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