Timmy's Lesson

The ringing bell announced the end of the long day and the students poured out of the building,  shoving and trampling each other in the long hallways. It was 6pm and the sun was still up in the sky, leaving them a few precious hours to have fun and blow off steam.

Pulling apart from the marching crowd, a group of boys gathered outside the school gates.

‘Let’s go to Ben’s place!’ shouted Thomas, a tall and slim guy, pushing his friend in the center of the circle.

‘Why me?’, protested Ben. ‘You know my dad’s still angry for the mess we did last time. It’s your turn Tom!’

‘No can do, smartpants. My sister’s already having her friends over. The house is off limits’

‘You’re both pussies!’ declared Jack, a big, confident dude with a bushy lumberjack beard which simultaneously gave him his nickname and made him the leader of the group. ‘Someone step up, now!’

‘Perhaps we can hang in my garage?’ offered Timothy, a small and skinny boy whose face was covered in acne.

‘Way to go, Shortstick!’ cheered Jack, punching his classmate on the shoulder which sent the poor lad staggering backwards. ‘Alright gang, let’s roll.’

Timothy’s house was located not far from school, on top of a small hill where the local kids converged to ride their bikes. It had a large front lawn that Timothy mowed every second sunday as well as a small pool in the backyard that they sometimes used when it was particularly hot.

 The group approached the white front door and Timothy brought out his keys to let everyone in, but to his annoyance the lock jammed, unwilling to turn.

‘What’s the matter, Shortstick?’

‘Dammit, my stupid mom must have left her keys in again. Hold on, guys.’

He rang the bell insistently several times. After a few seconds there was a hurried “I’m coming” and his mom opened the door.

‘Oh Timmy, you didn’t say you were going to bring friends over?’

‘Move aside, Mom, we’re hanging in the garage!’ He shoved her violently away from the doorway and let his friends in, pointing the way.

‘Hello Ms Baker, looking good today!’ winked the group boss.

‘Thank you, Jack’ replied the busty woman, smiling. ‘I’m glad to see at least some ofyou have manners, isn’t that right, Timmy?’

‘It’s Timothy! Now leave us alone!’ He turned his back and smashed the door, a gesture which would have been more dramatic if it didn’t get caught in the carpet, halting halfway.

‘Behold the mighty wrath of Shortstick!’ teased him Jack before pushing the door shut, properly this time, and following the skinny boy’s steps.

The garage was quite cramped, the center taken by his mom’s old car, while various tools and knick-knacks lay scattered on the floor, a remnant of the times his dad was still around. His friends didn’t ask for permission and made themselves comfortable, some taking the car’s front seats, others sitting directly on top of the rusty front cover. Timothy brushed the dust of a short wooden chair and set by the wall.

‘Yo Ben, check if the radio still works!’ shouted Joey, tapping on the front class. It worked and soon the music was blasting, making them feel like members of some private rock club.

‘So, when are you gonna tell us, Nick?’

‘Tell you what?’

‘About you and Stacy’.

‘There’s nothing to tell, man.’

‘You banging her?’

‘You jealous, Jack?’

‘As if, her face is like an old pancake. I’d rather bang your mom.’

‘No you wouldn’t’

‘Yes, I would, Joey. Have you seen Nick’s mom? She’s like, hot. Besides she was hired as secretary for Mr. Peterson, she probably gives him a blowjob every morning just to keep that job.’

‘Not funny, Jack.’ frowned Nick. ‘Why don’t we talk about your mom?’

‘Hah! What about her? She ain’t pretty, but nobody’s fucking her, that’s for sure.’

‘That’s because she looks like an old spanish laundry lady!’

‘Fair enough Thomas, not gonna argue.’ shrugged off Jack, lighting up a cigarette.

‘Hey, you can’t smoke in here!’ protested Timothy.

‘Or what, Shortstick? Your mommy’s gonna come and spank me? Hehe. More likely I’ll be the one spanking her!’

‘Take it back, Jack!’

There was a knock on the door, interrupting their quarrel.

‘Boys, I made you some refreshments!’ Timothy’s mom walked in, holding a tray with sodas and snacks.

‘Thank you Missis Baker!’ answered the six guests in unison.

‘Mom, we’re not children! Can’t you get us beers or something?’

‘There aren’t any beers left, Timmy. Besides, you love sodas. Why don’t you cheer up?’

‘Why don’t you fuck off! And it’s not Timmy, it’s Timothy!!’

‘Now, Timmy, that’s no way to speak to your mo…’

‘Leave us alone, mom!’

‘Relax, Shortstick!’ interrupted Jack. ‘And thank you for the sodas, Missis Baker, you’re awfully sweet.’

‘Now that’s a polite young man. You’re always welcome to swing by, Jack.’ Missis Baker put a warm hand on his shoulder.

‘Mom!! You don’t understand anything! His name isn’t even Jack, we call him that because of the beard...’

‘So what, Timmy? Jack is a fine name and if he likes being called that I don’t see a problem. Isn’t that right, Jack?’ The hand moved to the other shoulder, pulling him in a half embrace.

‘Thank you Missis Baker, finally someone who understands a man!’ he took a sip from his soda, casually throwing an arm around her waist.

 Timothy grew red. ‘Get your filthy hands down, Jack!’

‘Or what, Shortstick?’ he chuckled. ‘You’ll stare me to death?’

The small kid rose from the wooden chair and made a step towards Jack and his mother. His classmate shrugged and removed his hand, sipping some more from his soda.

‘I’m sorry Missis Baker, I didn’t mean to make no trouble. I know your son hates it when we play sweet with you.’

‘My son needs to learn how to talk to his mother.’ she slammed her foot down on the floor. ‘Isn’t that right Timmy?’

‘Yeah, yeah, whatever, now fuck off.’ Timothy gestured towards the door and turned his back, kicking something on the floor. Missis Baker was on her way out when she seemed to change her mind, turn around, and head back towards the group of boys.

‘You know what, Timmy? Mommy’s not going to “fuck off”. It seems I’ve raised a little brat. Jack here’ - she gestured towards the big bearded boy - ‘he may have his flaws but Jack is a real man, he’s polite and he knows how to treat women.’ And with that Missis Baker put her round, tight butt in Jack’s lap, leaned back on his broad torso, crossed her legs and stared her son in overt defiance.

Timothy’s jaw dropped and his pale, pimpled face slowly turned into a mixture of green and orange, like a rotting carrot. ‘I’m not a real man? I’m not a real man?! I’ll show you a real man you fucking bitch!’ He dropped his pants down and pulled out his cock, waving it in her direction.

‘Oh, Timmy, that little thing? Don’t make me laugh.’

His friends bent in laughter, holding their stomachs and banging on the hood of the car.

‘Wooo! Way to go Missis Baker!’

‘Now, if you look at your friend over here’ continued his mother, rubbing her but with slow circular motions on top of Jack’s lap, ‘I’m sure you’ll see what a real man looks like!’ She moved aside, letting everyone see the big bulge that had formed underneath Jack’s trousers. ‘And let me tell you something my little Timmy’ - she stressed the word “little” - ‘If you plan to be bringing your junk out, you better be ready to compete!’ She slowly unzipped Jack’s pants, plunged her hand in and pulled out his half-erect member. Even in this state it was visibly a lot bigger than Timothy’s. Miss Baker kneeled next to Jack, tying her hair in a ponytail.

‘May I, Jack?’

‘Heh. Knock yourself out, Missis Baker. I ain’t complaining’

‘No!!’ Timothy turned around, unable to watch.

‘Boys’, his mother called the ones in the car ‘Would you help me teach my son a lesson?’

 The boys jumped out and grabbed Timothy from both sides, turning him around and forcing him to watch as his mother’s lips first kissed the head of the big cock, then slowly parted away and took him in, sucking him with quick and masterful motions. In less than 10 seconds it was rock hard and double it’s original size, requiring the brunette’s head to bob up and down considerably to cover its entire length.

Timmy struggled to turn around but Ben and Joey were both stronger than him and holding him tight. He tried to close his eyes but he couldn’t, the surreal spectacle holding him captive.

After what seemed like an eternity his mom pulled away, licking her lips to his profound horror and disgust. She pointed towards Jack - ‘Now this, Timmy, is a real man’s cock’ - then she pointed towards him ‘and this is the tiny flaccid wee-wee of a little brat that insults his mother. Have you learned your lesson?’

Timothy was silent.

‘I don’t think he has, Missis Baker. Perhaps he needs an additional demonstration?’ Jack’s  fingers reached underneath her short skirt and pulled down black lingerie, letting it fall dangling around her ankles. Without skipping a beat he pulled her back into his lap, lifting her skirt up. ‘And you wouldn’t be so cruel as to leave me hanging after all this, would you Missis Baker?’

Timothy saw Jack’s long dick spurr from between his mother’s legs as the older boy rubbed it against her. There was a tension in the air as everyone held their breaths, waiting to see how she’d react.

‘Dammit, Jack, you know how to ask.’ conceded Missis Baker. Her legs parted away, revealing a neatly trimmed pink pussy, then she lifted herself up on her toes, pushed Jack’s cock under her folds and then slowly slid herself back down, biting her lip.

‘Holy shit….’ uttered Ben, forgetting to hold Timothy in his stupefaction, who crumbled helplessly on the floor, offering him a direct view between his mother’s legs.

Jack grabbed the middle aged woman’s round hips with both hands and started pounding her hard, her large round breasts bouncing up and down with every thrust. The teenage boys were all on edge now, their boners bulging quite visibly under their pants. Even Timothy, crushed on the ground, felt his boy penis grow hadder from watching straight into Jack’s big cock ramming into his mother’s tight pussy.

‘Aww, did little Timmy grow stiff from watching his mommy?’ she teased him in between heated breaths. Timothy’s cheeks turned a deep red from shame and embarrassment. ‘Even with a hard on it’s still so tiny, only good boys get to have big strong dicks, you know? Like this one.’ She lifted herself up again, letting everyone see Jack’s length before sliding back on top of it. At this point Ben shouted “fuck it!” and dropped his pants as well, pulling out his raging boner and masturbating to Miss Baker’s bouncing breasts. When she smiled and winked at him the rest of the boys followed, creating a semi circle around Jack, who began thrusting faster and faster, making large splashing noises each time Missis Baker’s plump bottom smashes into his lap.

‘Pull ‘em out, Miss Baker, pull ‘em out!’ the boys started chanting; jacking off closer and closer to her. Her skin getting hot and sweaty, she nodded, undoing a few buttons of her shirt and letting her round breasts pop out, their small black nipples standing hard.

‘Wooo!’ shouted Nick, shooting a premature load on her left breast, the thick slimy jizz sticking on top of it. Out of control, Timothy’s right hand grabbed his painfully erect member and began sliding up and down, slowly at first, fighting with the shame and horror of what he was doing, but then slowly accelerating, once he had realized he would not be able to stop anymore.

‘Jacking off with your little wee-wee, are you Timmy?’, teased his mom again while another boy send a hot load of sperm over her breasts. ‘Are you not man enough to play with the big fellas?’

Suddenly Jack’s rhythm accelerated and he held Miss Baker in the air while simultaneously drilling her at maximum speed from below, his hips thrusting and retracting, each time stealing louder and louder moans from the brunette until there was one last final thrust that stayed inside her, pumping her full to the brim. The sight of the cum overflowing from her wet pussy was enough to make all the boys who hadn’t already cummed do so, making a hot mess of Miss Baker’s shirt and outfit.

 Alone on the floor, Timothy came too, making a small wet puddle next to himself. Silent tears were dripping down his cheeks and he couldn’t bare to look up from the ground. Missis Baker stood up, Jack’s dick sliding out of her with a soft “pop”, put her underwear back on and walked over to her son.

‘Well, I hope you have learned your lesson, Timmy. No more talking back to Mommy, okay?’

She patted him on the head and left the garage, the sound of her high heels the only thing breaking the silence.

Nick was the first one to speak: ‘I’m sorry Shortstick, that must’ve been rough for ya. But damn, your mom’s hot. We couldn’t let the opportunity pass, you understand.’

‘He understands alright’ chimed in Ben. ‘Before the week’s over, he’ll be the one banging your moms!’ They all laughed, except for Timothy who remained silent.

‘Come on gang, it’s getting late. Let’s roll.’ Jack zipped his trousers and walked out the door, the rest of the boys following him. Some turned around to throw a last glance at Timothy, but most just hurried to get out of there. The skinny boy was left alone with his shame.

Part 2

Things got awkward for Timothy after the garage incident. That same evening he quietly went to bed without dinner, not daring to cross his mother in the kitchen. In his dreams he was falling, straight down towards an abyss while his laughing classmates swirled around him in bubbles that resembled breasts, bouncing off each other and spraying his naked body with milk from their nipples. As the ground approached he could make the outline of the gigantic pillars rising up to the sky, except they weren’t pillars but his mother’s open legs and he was falling inevitably between them.

Ho woke up in cold sweat and, to his shame, a wet bed, something that had not happened for several years. He quickly wrapped his sheets in a ball and tossed them in the laundry basket, hoping that his mom wouldn’t notice.

After his stomach had been rumbling for more than half an hour, he finally decided to come down for breakfast, approaching the kitchen table as if it were a tiger ready to pounce on him. His mom had made ham and eggs and had already began eating, gulping down her portion with her morning coffee.

‘Morning, Timmy!’ she greeted in between bites, not paying him much attention otherwise.

‘Mor- morning’ he managed, sitting down awkwardly on the opposite side of the table. His mom was wearing a tight black t-shirt with a white apron on top, which clearly defined the shape of her round breasts underneath. Her long smooth legs, barely covered by a short skirt, were crossed under the table, extending almost all the way up to his. Timmy swallowed with some difficulty. Wherever his eyes fell, something reminded him of last night’s ordeal. Images of his mother’s bouncing tits flashed before his eyes, followed with the painfully awkward pleasure of cumming while watching the rest of the boys cum on top of her. Except for Jack. He had a very distinct memory of the moment Jack filled his mother, his strong arms tensing as they held her tight against his knees, his eyes going wild and rolling up as he groaned in pleasure, his mom glowing red as she first struggled, but then relaxed, accepting the bearded boy’s seed inside her.

All of a sudden Timothy realized that underneath his loose shorts, his boner was peaking practically over the edge of the table. Hurriedly pressing it down with one hand, he devoured another egg in seconds and rushed back to his room, face burning red with embarrassment.

The rest of the day was no better, and as it was Saturday, there weren’t any classes to help distract him as his teenage mind replayed the scenes over and over again like a broken record. Timothy stayed alone in his room, trying to distract himself with video games and youtube, a desperate attempt that only postponed his mental torment. He didn’t dare to go down neither for lunch, nor for dinner, instead shifting from his bed to his computer in an endless cycle of anxiety.

Evening fell and night came and after long hours in his room Timothy decided that what he needed was a long warm shower to cleanse his body and ease his mind. The house was dark and silent when Timothy carefully went down the stairs, bypassed the kitchen and turned right into the short corridor that led to the bathroom. There he stopped, noticing the bright glow coming underneath the door and spilling on the hallway carpet. His mom was inside.

He listened carefully, but he couldn’t hear anything. ‘What the hell is she doing?’, Timothy thought, suddenly curious. He slowly approached the bathroom door, threading silently on the soft carpet. There was no sound still. He got down on his knees, leveling his head with the old wooden door handle, and peeped through the keyhole. His mom was in the bathtub. In the limited vision of the keyhole, Timothy saw her stomach and breasts, just on the edge of the water, and a hand, sticking out and holding the edge of a book. She was reading.

The young boy found himself glued to the view, his eyes following the foam bubbles as they slid down her soft round breasts, her wet skin shining and reflecting the yellow bathroom light, the flat surface of the water offering a teasing view of the submerged silhouette. For the hundredth time that day Timothy felt his dick painfully stiff. Still peeping he reached with one hand and pulled down his boxers, starting to slowly stroke himself.

The decisions he made weren’t as much conscious as they were the only course of action available to him, a relief from the unbearable frustration that he had endured throughout the day. His pace quickly increased, intensifying along with his pleasure, and Timothy struggled to remain silent as his right hand jerked him off furiously in the dark corridor. Painfully close to orgasm, his movements became faster still, his hand suddenly slipping away and colliding with the wooden door. His body weight shifted and he tumbled forwards, his legs tangled in his boxers, his head ramming against the handle and pushing it down with his chin as he helplessly tried to avoid the unavoidable while his entire body fell forward, opening the door and crashing sideways on the bathroom tiles.

He looked up and he saw his mom, looming over him as water dripped down from her naked body.

‘Please, mom, I can-’

‘Tusk, tusk, Timmy. Always a naughty boy, doing things in secret.’ She was not standing so close, the boy’s eyes could no longer focus on anything but her body, her clean shaven pussy only an arm’s reach away from his face. His dick was hurting from his ruined orgasm, painfully stiff but Timothy didn’t dare to touch it. His mom bent down, her full breasts filling his view as they descended towards him.

‘Such a bad, bad, boy, Timmy. If only you were a good boy’ - she reached out grasping his boner with her fingers - ‘helping in the house, doing the dishes… then perhaps mommy would be nicer with you’ - she smiled - ‘and with this little thing you’ve got here.’ It only took a couple of strokes to push him over the edge, his short cock jizzing in a sticky puddle next to him.

‘If only you were good.’

And with that his mother stepped  right over him, giving him one memorable view of her exposed sex, and returned to her room, leaving Timothy completely speechless.

The awkward night turned into an awkward morning and into an awkward week as Timothy struggled to make sense of the situation. Yet somehow, he found himself in the kitchen more and more often, doing the dishes and setting the table, sweeping the floor and cleaning the counter. He would exchange awkward glances with his mom, who just silently nodded in approval and carried on, like any normal mom would do when her son was doing the housework. Yet there was something else, something that kept Timothy constantly on edge yet somehow he was unable to quite put his finger on it. Perhaps it was the trace of a smirk at the edge of her smile, the way she carried herself around him, with more dignity and elegance, it seemed to the young boy, than she had in the recent years.

The week passed with no significant events and Timothy was starting to doubt whether he was just imagining things, whether everything that had happened, too unbelievable to even put in words, had all been a figment of his imagination, a crazy dream that he’d had. His everyday life was just as before, ordinary and unexciting, so impossibly distant and incompatible with the events that were now but a blur in his memories. It was Friday night, however, that brought the reality of things back into focus.

Timothy late watching TV in the living room and the lights in the house were off. During a commercial break he got up to fetch a soda from the fridge when he noticed the bright light in the corridor, shining through the bathroom’s open door. His heart began beating faster as he quietly approached. He stopped at the edge of the door - any step further would allow him to be seen.

‘It’s okay, Timmy’, came his mother’s voice from inside, ‘you can come in.’

His mom was in the bath, this time sitting sideways, her back leaning on the opposite wall and her knees resting over the edge of the tub, leaving her legs dangling. They were slightly apart, giving him a central view of her body and breasts, leaving the submerged part to his imagination. She tucked a wet strand of hair behind her ear and smiled devilishly.

‘Well, what are you waiting for, Timmy? Aren’t you going to get your little friend out?’

The world “little” stung him, but not enough to disobey, and the teen dropped down his pants, revealing his small boner.

‘Go on, then. Mommy knows you’ve been a good boy. You’ve earned it.’

Burning with shame, Timothy began stroking his dick. Perhaps it was the awkwardness of the situation, or the suddenness of the opportunity, but for some reason he couldn’t get much pleasure out of it and in a moment it returned to a flaccid state.

‘Aww, how cute. Mommy’s little boy turned out to be a little girl.’ Timothy’s eyes began to water with tears. ‘It’s alright though’ - she continued - ‘come closer, Timmy.’

He made a few steps until he was standing right beside the bathtub, his mother’s full breasts and hard nipples tantalizingly close to him. From this distance the water wasn’t much of an obstacle to his view either, and his mom spread her legs a little wider, allowing him to watch.

It proved enough to reignite his vigor, and within seconds Timothy was masturbating furiously, unable to control himself. He shot out his load and it landed in the water, floating underneath his mother’s breasts.

‘You can go back to your room, sweetie’ she said, and Timothy, face completely red under his acne, didn’t wait for a second command to run out of the bathroom.

The following week progressed smoothly, and Timmy continued to execute the house chores with fire and diligence, earning his mother’s silent approval. His first misstep however was on Wednesday evening, when he was sitting alone on his computer when he received a message from Ben. “Check this out, man!” it read, followed by an attached link. http....5844/Dis... “This totally looks like Jessica! Can you imagine that little bitch being spanked into submission?”

He clicked on it and an image appeared, depicting a young girl, who indeed looked just like Jessica, being bent over and spanked with her panties down. It was only a matter of seconds before he unzipped his pants and grabbed a fresh tissue, eager to relieve his arousal.

‘You shouldn’t be doing that, Timmy!’ came his mother’s voice from behind, making him jump from surprise. With his headphones on, he hadn’t heard her come in. ‘Only naughty boys look at naked women online!’ she scolded him. ‘Drawings of women, nonetheless. Porn is bad as it is, but you aren’t even man enough to look at real women? I’m very disappointed.’

‘No, no, mom! It’s not what you think! Ben sent me this link and I just clicked on it and…’

‘And your pants fell down, I see.’ she finished with a grim voice. ‘I was about to let you off the hook, but lying to your mother? I can’t tolerate that! Come with me.’

Struggling to quickly pull up his pants, Timmy followed his mom out of the room and down the stairs.

‘Get your clothes off and sit in the tub!’ she commanded, disappearing into her room. Bewildered, the young boy obeyed, wondering what his mom was about to do.

She returned a few minutes later, a mysterious smile on her lips. Before the boy had had time to ask any questions, she leaned down and forcefully grabbed his dick.

‘So, my sweetie, you’ve decided to go and watch naked women behind Mommy’s back?’ She was stroking him fast and hard, her fingers squeezing tightly around his shaft and arousing him quickly. ‘Do you not know this is what bad boys do?’ He was rock hard now and she slowed down her pace, avoiding a quick orgasm. ‘After all that I’ve given you? Just when I thought you were becoming a good boy?’ She slowed down further, doing light slow strokes that kept him on edge but were not enough for an orgasm. ‘Mommy is disappointed. Mommy is disappointed so very much.’ She finished her last stroke, her fingernail dragging the length of his erect penis ready to burst, the shivers making his member pulse and throb. Then she quickly grabbed the shower head and unleashed a torrent of ice cold water over his crotch, maintaining control over him despite his violent protests.

In less than 10 seconds his penis was brought down from the edge of orgasm to a completely soft state, his balls painfully aching from the frustration. Just when he thought things couldn’t get any worse, his mom pulled out a little metal contraption and wrapped it around his flaccid member, pressing it tightly and locking it with a little padlock, to which she retained the key.

‘This is your punishment both for what you did and for lying to me. Mommy will release you if you’re behave like a good boy.’ And with that she stormed out, leaving him in the cold tub.

That evening Timothy struggled with all his strength to remove the damned chastity cage, trying all sorts of clever tricks, all to no avail. His mom had put it on very tightly and he understood there was no chance of removing it without the key. In his frustrated state, he spent the night sleepless, turning in his bed in search for salvation which never came.

Thursday proved to be a constant nightmare and Friday was a living hell. As a teenage boy, Timothy was used to waves of sexual frustration that he relieved on a daily and sometimes hourly basis. Being forced to spend two whole days on the verge was more than he could take, so as he returned home from school on Friday evening, he literally came crawling into his mother’s room.

‘Please, mom, I can’t take it anymore….’ he whimpered, legs crossed like a little girl holding herself from peeing and an embarrassed look on his face.

She looked at him and sighed. ‘Fine, sweetie, I suppose I can give you a reward for being good... ‘, she paused, pensive. ‘Do you want to take a shower with Mommy?’

He nodded, too afraid that if he spoke he’d say something which would make her change her mind. Timothy was sure he would go insane if he had to spend another day in the cage.

His mother stood up and slowly unbuttoned her shirt, throwing it on the bed behind her. Without pausing she reached behind her back and undid her bra. She was completely topless, save for the small chain necklace she was wearing, and the little key at the end of it. Her large breasts were just on the short boy’s height, his face ready to plunge between them if he stepped forward. The thought was both pleasant and painful, his confined penis hurting against the walls of the chastity cage. Then she was naked, standing before him a head taller, her perfect hourglass body taunting him with its unattainable proximity.

‘Now’s your turn, Timmy’ she said, reaching out and pulling his t-shirt over his head. His body was small and skinny, with a pale complexion and the occasional pimple, just like his face. If he had any muscles, Timothy would’ve perhaps been a bit more confident standing naked, but as things were he tried to conceal his weak body with his hands. Not minding him, his mom bent down and pulled down his pants and underwear, revealing the small metal cage around his member.

‘Let’s go, sweetie.’

She took him by the hand and let him across the corridor into the bathroom, where they both stepped into the shower cabin. She turned on the water - this time it was warm and pleasant, trickling down his body and calming him down. Then his mother kneeled in front of him, getting at the height of the cage, and used the key from her necklace to unlock the contraption. There was a small click and Timmy felt freedom for the first time in what seemed like an eternity of agony. He looked down with gratitude on his mom, her current position offering him excellent top view of her full breasts. Water was pouring down and converging between them, where it fell down her stomach in a small stream. Timothy’s cock stiffened and before he knew it his mother had started to tenderly stroke it, pressing forward and letting it lay on top and in between her tits.

‘Are you gonna be a good boy, Timmy?’

‘Yes! Yes of course I will!’

‘Can you promise Mommy?’ she squeezed her breasts around his shaft.

‘Yes! I promise!’ he was starting to pant.

‘Say “I promise, Mommy!”’ she insisted.

‘I promise…’ - he gulped ‘Mommy’.

‘Thank you, Timmy.’

She opened her mouth and her plump lips wrapped around his boner, the wet warmth of her mouth fulfilling every dream of his young teenage mind. She sucked him back and forth with the technique and excellence of women who know what they’re doing, making every fiber of his being implode into pure pleasure. He reached down and grabbed her breasts with both hands, pushing them even tighter against his body. They felt amazing, an incarnation of softness and lust that penetrated his body and mind. The boy groaned and came, his short member unloading all the frustration he had accumulated in his balls from the last two days’ torment.

She swallowed and smiled, pulling her mouth away from his now shapeless cock.

‘See what rewards you can get if you’re good?’

Timothy nodded.

‘Now stay good!’ She said with a wink, quickly putting his penis back in the chastity cage and locking it with the key. ‘Just something to help you avoid looking at naughty pictures online.’ She smiled and walked out of the shower, leaving him in the warm afterglow of the event.

The next few days were good for Timmy, and even though he was forced to wear the chastity cage all the time, his mother had a shower with him every evening, helping him relieve the frustration and rewarding him for being a good boy and helping around the house. Over time the boy grew accustomed to this routine and old drawbacks paled in comparison to the new advantages, not the last of which were the amazing blowjobs he regularly received and for which, he was sure, all of his friends would give an arm and a leg to be in his place.

This newfound confidence made Timothy grow bold with time, and he began sometimes fondling his mom as she walked by at home, slapping her ass or even pulling her hair when she was sucking him off in the shower. In turn Missis Baker didn’t seem to appreciate her son’s development, as for once he had seemed to be going in the right direction, finally following her orders and doing the chores as a good boy was supposed to. Timmy even began rushing through his tasks, doing things only halfway or sometimes forgetting to do them at all, and his mom was not happy. She began skipping reward days, hoping that his frustration would put him in his place, but instead Timothy grew even more insistent, claiming the rewards as a right that he had.

‘Mom, you’ve let me two days again, this is unbearable!’ he would say, rushing home from school.

‘But you forgot to do the dishes yesterday, Timmy!’ his mom would reply.

‘But I did them today, didn’t I?’ And they would go in the shower and she’d unlock his cage, finding less and less enjoyment in it each time.


One Friday Timothy came home especially frustrated, as his mother had let him sit in the cage without relief for 3 whole days. He could barely sit through dinner and gritted his teeth while he grudgingly cleaned the table and did the dishes, missing a few and half-cleaning the rest, eager to get things over with.

‘Mom! I’m done!’ he shouted, trying to locate her.

‘Over here, Timmy’ came the reply from his mother’s room. He headed towards the voice of his mother, flinging the bedroom door open. It was dark and he couldn’t see much.

‘You can turn on the light’ came her voice from the bed. He flicked the switch. His mom was lying on the bed, almost naked, wearing lingerie he had never seen before. Her bra, black but mostly transparent, left little to the imagination, and instead of panties she was wearing a garter belt and stockings, but nothing to cover her clean shaven pussy.

‘I’ve got something special for you tonight, sweetie.’ she said with a lusty voice. ‘Why don’t you sit over there?’ - she pointed at the carpet next to the foot of the bed, right in front of her. Tingling with sweet anticipation, Timothy obeyed the order.

‘Now just watch and enjoy’ she said, spreading her legs wide and running a finger down between her folds. Mesmerized, Timothy followed as it went up and down, circling around her sweet spots, teasing and playing with her clit, plunging inside her and sliding slowly out, covered in sweet juices. It was a wonderful and hellish journey that made his 3rd day blue balls ache and swell, screaming for the moment of sweet release.

Meanwhile his mother began playing with her breasts with her other hand, pressing them together and gently pulling and pinching her nipples, an activity that was progressively accompanied with louder and louder moans. The teen boy’s cock would’ve been rock solid by now if it wasn’t for the cage, and even so, despite the constrained space, he felt it grow as hard as it could and push against the bars of its metal prison. Timmy began rocking back and forth involuntarily, following the movement of his mother’s fingers in and out of her pussy, tingling with anticipation of what was to come.

‘Timmy, I need something in me.’ whispered his mom and he immediately sprang to his feet. ‘There is a drawer on my nightstand, would you open it and get the things for me?’

Curious, he ran to the nightstand and flung it open. Inside there was a large black dildo, a pack of condoms, and lube.

‘Can you put a condom on the dildo and pass it to me?’ ashed his mom, still touching herself.

Timothy struggled with the condom for a while but finally managed to tear it open, sliding it around the dildo. It was embarrassingly larger than him. When he gave it to his mom she asked him to sit down on the same spot again and he reluctantly did, feeling his frustration border more and more on physical discomfort and pain.

The dildo was indeed very large and thick, and he awed in amazement as his mom’s pussy stretched to accommodate it all the way in, her stomach not even bulging from the effort. It made loud, sloppy sounds every time it went in, and as his mom increased the pace, her moans quickly supplemented.

After ten minutes that lasted forever, she finally pulled it out and said ‘I’m ready for some real dick now.’

In an instant, Timothy was up, his hand outstretched for the key.

‘Oh no, not you sweetie,’ his mom laughed. ‘I’d never be satisfied with that tiny thing. I need a real man. Jack?’

The door of the wardrobe slid open and Jack stepped out, naked and with an enormous erection. Clearly he had been watching the whole thing. Timothy’s jaw dropped.

‘Now sit back on your place, Timmy’, his mom continued ‘and if you leave the room or try to do anything that I haven’t told you, you’re never getting that key.’

The young boy half-sat half-fell on the ground, his mind refusing to believe what was happening. From a front view seat he watched his mother lift up her legs and spread her pussy as Jack got into position and penetrated her, stretching her even more than the black dildo had. The moans and screams that followed merged into a sea of lust and chaos that engulfed him completely. His constrained balls had already been on the point of bursting ever since he’d entered the room, and now all that was happening was simply too much for him. When Jack grabbed his mom’s hips and began aggressively pounding her, his rhythm accelerating in an upwards crescendo, Timmy’s mind went blank, his body spasmed, and his dick - stiff, painful, constrained - slowly jizzed out a thin drip of semen from the confines of its cage. Soon after Jack’s ascension ended and with one final, powerful thrust - as if mocking Timmy’s impotence - he filled his mom to the brim, leaving small white droplets ooze out of her.

When Jack stepped away, the caged boy, head still spinning, heard his mother’s voice: ‘Come lick them, Timmy, make Mommy clean again.’

Not daring to refuse he leaned forward and stuck out his tongue, trying to wipe out the leaking semen. It was bitter and salty, but there was also the sweetness of his mom’s juices thrown in the mix. Timmy had never felt that submissive before.

When he’d finished, he looked his mom’s face and meekly asked: ‘Mommy, can you please unlock my cage now?’

‘But why sweetie? See, you didn’t need that to cum!’

‘But mom please, you promised….’

‘Hush now sweetie. You haven’t been a good boy lately. Mommy has thrown the key away.’

‘What?!’ Timmy’s eyes grew wide from horror and surprise. ‘But, but, but this means that I’ll be trapped forever! I’ll never be able to cum again!’

‘Nonsense, dear, I’ve just told you. You can cum again fine as it is. You’ve just done it.’

‘But this was just this time when Jack…’ the boy began.

‘Jack will be coming here very often from now on, sweetie.’ his mom interrupted. ‘And you’ll be watching us every time. Feel free to cum whenever you want to. But you’re never getting that key again.’

His mom got up and kissed Jack passionately, her hand stroking his dick and making it hard again.

‘Ready for round two, my love?’