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“You want me to do what?!” Henry was flabbergasted. He stared at his mother in complete astonishment.
“Oh, come on, baby,” Henry’s mother rolled her eyes with a sigh. “I know you’re embarrassed and this is all new—but I know you’ll love it!”
Henry blinked as if he were trying to break out of a hallucination, “N-no! This is weird—it’s not right, mom!”
“Henry,” his mom said in a scolding tone, “don’t try and pretend that you don’t want this. I found what you were looking at on your computer—it’s filled with those videos!”
Henry’s face turned a deep crimson and he avoided his mother’s eyes. “I-it was just a fantasy—I didn’t want it to actually happen!”
His mom rolled her eyes again, clearly not believing a word he said. “Fine,” she stepped back from her son, “if you’re going to be fussy about it, then I have no other choice.”
Henry’s brows furrowed, “What do you mean?”
His mom turned around and left the room, leaving Henry to sit in his confusion all alone.
That evening, Henry was sitting on the living room couch and watching TV when the doorbell rang. His mother entered through the kitchen, she was wearing a fancy blouse and tight pants. They hadn’t talked since his mom had come to him with her . . . suggestion and Henry didn’t want to be the first to start a conversation.
The door opened to reveal a taller woman with a very professional air to her. She smiled at Henry’s mom and they shook hands.
“Hi,” the woman said in a sweet and kind voice, “you must be Ms. Willis, Henry’s mom?”
“Yes, that’s me,” Henry’s mom said with a smile. “And you must be Mary.” The woman nodded as she pulled back her hand and rested it on the handle of a suitcase standing next to her. “Come in, come in!” His mom encouraged.
“Here, let me grab your coat,” his mom offered politely, “and Henry is just in the living room.”
Henry paused the TV, sitting up straight to look at the woman—Mary—and trying not to look as confused as he was.
Mary smiled at him, “What pretty young boy!” She complimented, though it seemed more directed to his mom than Henry.
“Isn’t he?” His mom laughed.
Mary nodded, “So, do you have everything set up?” She asked his mom, not even acknowledging or introducing herself to Henry.
“Yes, sort of,” his mom said while looking around the house for anything forgotten. “I’ve got all the bathrooms locked up, bedroom closed—I’ll clean it out later, I set up the new one in the guest room, and you’ve got all the supplies, right? I didn’t have a chance to run to the store.”
“Perfect,” Mary said cheerily, “and yes, I’ve got all the basic supplies in the bag. Some new clothes—if we even need them,” they both laughed, “bottles, cleaning supplies, and of course, both diapers and pull-ups.”
“Um—what?” Henry finally butt into the conversation, still utterly confused.
“I broke the news to him this morning,” his mom loud-whispered to Mary, “he’s been pretty fussy about it.”
“Nothing I can’t handle,” Mary assured. She turned to Henry who was still sitting on the couch, placing her hands on her knees as if talking to a toddler. “Alright, honey, we’re going to be changing you into something a little different, okay? I’m here to help you get adjusted to it!”
Henry stared at her as if she were speaking a different language—he couldn’t even begin to process what she was talking about.
“I’ll help you get him changed before I head out,” his mother offered, walking over to Henry.
Before he could register what she was intending, Henry’s mom was pulling off his shirt. Instinctively, he raised his arms without even realizing. But when she went to unzip his jeans, it finally clicked.
“What—m-mom, stop!” He tried to push her hands away but Mary was suddenly right next to him and grabbed his wrist. Mary was much stronger than he expected and Henry was unfortunately failing gym class.
His mom was unfazed by Henry squirming his legs and managed to pull his pants and underwear off all in one go. Henry was left completely naked and exposed as his mom gathered his discarded clothes under her arm.
“Alright,” his mom huffed from the effort, “you’ve got it from here?”
“Yes, thank you,” Mary chirped and let go of Henry’s wrists, he immediately covered his crotch and curled in on himself, hyper aware of the large window anyone could see him from. “Enjoy your evening Ms. Willis, you’ll have a well-trained baby boy when you get back!”
“Thanks again, Mary!” His mom smiled as she grabbed her coat and keys, “Good luck!” And with that, she was gone.
Mary went into her suitcase and pulled out two packages—one of diapers, the other of pull-ups. She turned around to find Henry in the exact same position, frozen in shock, fear, and humiliation.
“Now, Henry,” Mary’s voice suddenly went stern, “you have two options. Either I put you in a pull-up or diaper, or you stay completely exposed for anyone to see.” She gestured to the wide window that put the whole living room on display.
Henry stayed silent, unsure how to get out of the situation.
“If you let me pad you up, I might just put you in some jammies I brought—but only if you be good and do as I say.” Mary promised with her commanding tone, “But if you don’t comply—you’ll stay naked all night, you’ll be forced to make a mess on the furniture and carpet, and you won’t get any rewards.”
Henry wasn’t sure what a reward would entail but he was positive it wasn’t going to be getting his normal clothes back. He was ashamed to say that he wasn’t sure he’d be able to put up too much of a fight. He couldn’t see a way out this scenario and he wasn’t totally convinced he wanted to find one. No! Henry thought, This is wrong! It’s gross and I DON’T want anything to do with it!
“What will it be, Henry?” Mary pulled him from his thoughts, “Diaper or pull-up?” She was holding up one of each in her hands.
Henry swallowed, avoiding eye contact as he very shamefully said, “. . . Pull-up.”
Mary smiled triumphantly, “Good boy.”
Henry avoided looking at Mary or any of the supplies she had brought as he was . . . changed. Mary had gotten him to stand up as she helped him step into and slip on the pull-up. It felt weird to have on, every time he would move it would crinkle and the padding between his legs reminded him of how long it took him to start wearing underwear in the first place. He was a late bloomer.
Once he was in nothing but a pull-up, he awkwardly sat back down on the couch. Mary put the diaper back in her suitcase and retrieved a sippy cup that was already filled with milk. She set it down on the table in front of him and grabbed the remote.
“Be sure to drink up, baby,” she encouraged sweetly, all sternness washed away. “The sooner you use your pull-up, the sooner you get your reward! Now, let’s put on something more appropriate for a baby boy your age.”
Mary flipped through the channels before she settled on something, “Aha!” She exclaimed, “A Barbie Princess marathon! Your mom told me how this is your favourite!” She chirped as she sat down on the couch next to him, immediately getting comfortable with a blanket.
Henry tried not to move as much as possible, not wanting to cause any crinkling and too humiliated to get comfortable himself. He stared at the milk in front of him, smart enough to assume that this was going to be his only option for something to drink. He’d just had supper and hadn’t had a chance to use the bathroom before Mary had unexpectedly shown up. He also had very little to drink with his meal, so he was fairly thirsty.
“It’s okay, baby, don’t be shy,” Mary had noticed that Henry was staring at the sippy cup. “You must be awfully thirsty, you should drink your milk so you can grow to be big and strong!”
Henry didn’t want to test Mary, especially when he had no clue how long the evening would last and his mom would come home. So, he grabbed the sippy cup and sucked it into his mouth.
Mary beamed at him, “Great job, baby!” She praised, reaching over to pet his hair, “I knew you were going to be a well behaved little boy!”
Henry blushed and turned back to the movie, absentmindedly taking the occasional sip from his bottle.
As the movie went on, Henry finished his milk faster than expected but was still not fully relaxed—especially since his bladder had filled. He tried to ignore it the best he could by subtly bouncing his leg, but soon enough it wasn’t helping. Henry started to squirm which caused the pull-up to crinkle, catching Mary’s attention.
A mischievous smirk crossed her lips, “you know, Henry, your mom already locked all the bathroom doors.” She informed him happily, “And you’re wearing pull-ups for a reason.”
Henry shook his head, looking away from Mary as the urge to go grew stronger. He couldn’t stop himself from rocking in the pull-ups, accidentally causing him to grind against the fabric which was a whole other level of embarrassment.
“Oh, poor thing,” Mary pouted as she scouted closer to Henry. “Little baby is nervous about using his pull-ups for the first time—here, let me help.”
She placed a hand on his chest to guide him to lean back. Too focused on not peeing himself, Henry followed her lead and shifted to lean back against the couch. His thighs were glued together, hiding his hands that were protecting his padded crotch.
Mary placed a gentle hand on his knee to guide his legs open. Henry felt his eyes start to well up as he did nothing to stop her from spreading his legs.
“Shhhh, it’s okay baby, there there.” Mary cooed softly, it wasn’t until then that Henry noticed the phone in her other hand, recording his compromising situation. A tear slid down his cheek and his chin wobbled. “Oh, poor baby, I know this is scary, but you’re going to feel so much better once you just relax.”
Henry shook his head again, avoiding looking at the camera as if it would make it go away. “Come on, honey, how ‘bout you move your hands so I can see what’s happening? Can you do that sweetheart?”
Reluctantly, Henry pulled his hands away from his crotch and covered his face instead to hide the shame. With nothing to hold back the flood gates, his body released and a hissing sound filled the room. Henry started peeing in his pull-up, turning the white yellow as he could do nothing to stop himself even if he tried. The warmth enveloped his privates which sent a shameful tingle down his spine. All the videos he’d watched resurfaced in his mind and his crotch heated up even more.
Finally, his flow came to a stop and he was left in his warm and puffy pull-up. Mary set the phone down once he was done and put her hand on the pee-filled fabric.
“Well done, baby!” Mary praised before grabbing onto the hem of the pull-up and pulling it off of Henry. “Oh, look at this! It’s absolutely soaked!” She placed the pull-up on the ground next to the couch then turned back to Henry. “Speaking of—look at how wet it is down here!” She scoffed and ran her middle and ring finger through his sopping folds.
Henry squeaked in surprise and removed his hands from his face, looking at Mary in bewilderment.
“Who knew such a little thing could get this soaked,” Mary tease as she spread his folds to get a better look at him. Henry’s face turned a deep red, and before he could do or say anything, she slipped her fingers into his sopping hole.
“Ughn!” Henry gasped and clenched instinctively.
“Little baby is so tight!” Mary chuckled, moving her fingers in and out of his hole. “Be a good boy and relax, sweetheart. This’ll feel so good!” She promised as she used her thumb to circle his clit.
Henry gaped like a fish, pleasure overwhelming him in a way he could never imagine. He’d never been touched like this by another person—knowing it was wrong made it feel so much better. His head fell back as the pleasure built up faster than he was expecting.
“Aw, does baby like that?” Mary cooed, “Does he like being full of my fingers? I bet me rubbing your clitty feels so good.” She hummed as she sped up her thumb, pulling a moan out of Henry. “I also bet you wish your mommy was here,” she pouted, inserting a third finger into his hole. “Wouldn’t it be nice to have mommy doing this for you? Cleaning you up after you wet yourself, changing you, playing with your pretty pussy—doesn’t that sound nice?”
Henry couldn’t help to close his eyes and picture his mom, her fingers deep inside of him as she praised him. His moans built up at the thought, the desire for his mommy becoming even stronger. Before he knew it, he was pushed over the edge.
“Mommy!” Henry moaned as he came on Mary’s fingers.
Mary slowly pumped her fingers in and out of Henry, carefully rubbing his clit as he came down from his high. “There we go baby, good boy. Let it all out, you did so well!” She praised, though Henry didn’t hear much of it as his brain went all foggy.
He allowed Mary to move him as she needed while she cleaned him up. Henry was wiped and powered and pampered with a fresh pull-up, although he never did get any jammies to go over top. But he’d already forgotten about them anyway, not minding being exposed in his pull-up.
Mary did give Henry a blanket to keep him from getting cold as well as some freshly warmed milk. Henry suckled on the milk absentmindedly as his attention was caught by Barbie on the TV.
As he drank his milk, he thought more about his mommy. He pictured her fancy blouse and its low neckline. His face went pink as he thought of what was underneath the blouse, what kind of bra she might’ve been wearing, and wondering what it would be like to suck on her breast. He started to drink faster as he thought of being cradled in his mommy’s lap while drinking her milk.
“Here, I’ll grab you some more,” Mary said as she grabbed the empty sippy cup from Henry. He hadn’t even noticed he’d run out, he was too distracted with the satisfying sucking motion that he didn’t even realize he wasn’t getting anything out of it.
The night continued on like that, Henry constantly having something to drink in his hands while watching TV. Gradually he moved closer and closer to Mary, starting with just leaning against her to eventually fully sitting in her lap.
Soon enough, so many Barbie movies had passed, Henry had no clue what time it was. He was starting to miss his mommy.
“Well, sweetheart,” Mary patted Henry’s bottom, “your mom should be on her way home now—she really enjoyed the video I sent her!”
Henry blushed and felt a little tingle in his tummy. He was so focused on being excited to see his mommy, that he didn’t even bother stopping himself as he began to wet himself.
Mary, whose hand was still on Henry’s bottom, felt the heat filling his pull-up and smiled. “Good job, baby!” She praised, “How about we get you changed somewhere a little more comfortable, yeah?”
Henry nodded, unsure but excited to see where she would take him.
Mary scooped Henry up in her arms with ease, carrying him upstairs. They passed his room, instead heading into the guest bedroom. Inside was filled baby toys and other baby items, the walls were pink and the bed was like an extra large crib. Opposite of the bed was a large table—a changing table. A cute pastel shelf next to it contained all your diaper changing needs.
Mary laid Henry down and slipped off his pull-up. Henry automatically opened his legs, allowing Mary to see him fully exposed.
“Good boy! Already knows what to do,” she cooed as she tickled his tummy. Henry giggled, squirming a bit to try and get away from her tickles. “Baby deserves his reward, doesn’t he? Yes he does! Yes he does!”
“I can take care of that,” standing in the doorway to the guest bedroom was Henry’s mother. “If you don’t mind, Mary.”
Mary turned around and smiled, “Of course! I’ll leave you to it!” She winked and moved out of the way.
“Mommy!” Henry moaned as he got full view of his mom.
“Hello, darling,” she smiled and came over to the end of the table, “have you been good for mommy? You look absolutely adorable!”
Henry nodded and whined as he squirmed his hips, desperately needing friction now that his mom was here.
“You deserve something special, now don’t you baby?” She said as her thumb rested on his clit, gently starting to rub. “That’s it baby, nice and wet for mommy. Just relax and let mommy take care of you.”
Henry moaned as his mom dragged her fingers through his folds. He started to whine when she pulled away for a moment, but it soon turned into a gasp as he felt something much larger run through his pussy. Suddenly, he felt it slowly ease itself inside of him.
“Aw, baby,” his mom cooed as Henry’s eyes glossed over, “you like the feeling of mommy’s cock inside you?” She said as she bottomed out. Henry moaned loudly as she started to thrust shallowly inside her son. “You look so cute split open on mommy’s cock! You love it, don’t you baby?”
“Mommy!” Henry groaned as she rubbed his clit in time with her thrusts, “it feels so good!”
“I bet it does, sweetheart,” she started to move faster, wet sounds filling the room. Henry clenched his hole around his mommy, trying to milk her cock. “You’re so adorable, baby,” she cooed, “did you have a good time wearing your diapers?”
Henry whined and nodded, grinding his hips down in time with his mom’s thrusts. “Yes, mommy!”
“Mommy’s so happy to hear that, baby,” she smiled as her thrusts became deeper, making Henry feel so full. He moaned as she slowed her pace to make sure she was fully bottoming out with each thrust. Drool fell down his chin as his eyes started to lose focus.
“Feels good, doesn’t it, sweetheart?” His mom asked as moved faster but still made sure to stuff him full.
“Mmm, mommy,” was all Henry managed to get out, groaning as his mom put more pressure on his clit.
“Aren’t you thankful mommy put you back in diapers?” She asked in an infantilized tone, watching his eyes glaze over with the more she moved. “Those big boy pants were too much for you, weren’t they?”
Henry moaned and nodded, slightly gurgling as well with all the drool built up in his mouth.
“You needed these diapers, didn’t you, sweetheart?” His mommy continued, her hips moving faster along with her thumb. “Because you’re just a little baby—my precious baby boy.”
Henry nodded furiously, panting as his mother pounded her thick cock into his sopping pussy. “Mommy, mommy!” He moaned loudly as he suddenly came on his mommy’s fingers and cock.
“Good boy!” She praised, slowing her thrusts and her rubbing, “That’s my good boy, let it all out, baby. Just relax. Mommy has you.”
As Henry’s climax died down and he relaxed to his mom’s comforting words, he couldn’t stop himself from releasing completely. Urine trickled over his mom’s cock still inside him and soaked the table underneath him.
“Oh, baby,” his mom cooed, continuing her rhythmic thrusts as Henry peed. “Look at you, making a mess,” she tsked, “good thing mommy will clean it all up.” She reassured.
Once Henry’s bladder had emptied again and his orgasm had fully gone down, his mom pulled out of his swollen pussy.
“Look up at mommy, darling,” she said sweetly as she tugged on her cock. Henry, who was still a bit dazed, managed to look at his mom. It didn’t take long before she was spurting all over Henry’s stomach and chest, a little even managing to land on his neck and chin.
“You look gorgeous like this, baby!” His mom praised as she leaned over to kiss her son on the forehead, pulling away to admire the state of him. “You did so good today, baby. How about you catch some sleep? Mommy will clean you up.”
Henry didn’t need to be told twice, falling asleep almost immediately, excited for what his mommy would have in store for him tomorrow.