Tom's Playdate

Back to the first chapter of Tom's Playdate
Posted on May 11th, 2026 03:15 AM

Topsy was busying herself helping Tom into a large baby bouncer in the living room. It took a moment to situate him in the thing in a way that didn’t wrinkle his dress. She managed to secure the harness of the bouncer underneath his dress rather impressively. Tom was not as impressed, hoping the embarrassingly poofy dress would at least let him escape the embarrassing contraption. Unfortunately for him, Topsy found a way.

“Now you wait there while we say hi to Haruhi and her baby Rosey. Then you two can go play,” Tom responded with a pout to his mommy. The moment was interrupted by the door bell ringing. “Oh, speak of the devil.”

Butch was the one that answered the door and he was greeted rather suddenly by an Excited Rosebud.

“Uncuh Butch!” Rosebud said excitedly as Butch opened the door. There was a startled gasp of surprise as Rosebud shot out, his leash escaping the clutches of his mommy. Rosebud playfully tackled Butch to the ground.

“Rosey be careful!” Haruhi moved to pick Rosebud up but stopped short.

“Hey there sport!” Butch said rolling over so Rosebud was underneath him. “Someone’s rambunctious.” Rosebud giggled in response and the two proceeded to playfully rough house as the other alley cats greeted their guests.

“Haruhi!” Topsy excitedly ran up and hugged the woman. Haruhi knelt down to hug the cat at her level.

“It’s been a while,” Micheal added.

“It has, but you guys have had a new baby to break in,” Haruhi stepped inside and Micheal closed the door behind them. “Speaking of, where is the cutie?” The hug between her and Haruhi broke off as the two alley cats led her over to Tom, who started fussing in the bouncer at being perceived. “My gosh he is absolutely adorable. May I?” Haruhi gestured to the struggling baby cat.

“Go ahead, but he might get a little fussy though,” Topsy answered without sparing Tom much of a thought. Tom squirmed as Haruhi rather effortlessly lifted him out of the bouncer and held his weight on her hip.

“You are such a cutie,” Haruhi said playfully booping Tom’s nose. Tom struggled and squirmed but it was little use against Haruhi. The alley cats had gotten pretty good at physically controlling him, but that was nothing compared how physically small he felt being so effortlessly lifted by the woman twice his size. “Squirmy though,” Haruhi said placing the pacifier clipped to Tom’s dress into his mouth. “I think both of our little ones have some energy they need to get out,” Haruhi said gesturing to Butch and Rosebud, who had stopped rough housing and were panting and giggling as they laid next to each other.

“Why don’t we get them settled into Tom’s nursery,” Micheal offered.

“Yeah, while they’re playing, we can show you Tom’s baby book,” Topsy added. “There are some great pictures in there.” Tom shifted in Haruhi’s arms and blushed more.

“I like that idea,” Haruhi’s face lit up. “Rosey!” she called out in a distinctive commanding voice. The dog was up and by her side in a moment.

“Yes mommy?” he said eagerly.

“The adults are going to talk for a moment while you and baby Tom play, ok.” This was the first moment Rosebud had gotten a look at Tom. The adult baby cat in one of Topsy’s sissy dresses that was taking his usual spot on his mommy’s hip. The two shared only a brief glance before Tom buried his head into Haruhi out of embarrassment.

Haruhi grabbed Rosebud’s leash again with her free hand and the group followed Micheal and Topsy to Tom’s nursery. Rosebud took in the familiar yet different room when they arrived. He had taken residence in the room whenever the alley cats baby sat him, before it was made into the full-blown nursery it was now. It was definitely less pink then, and less well stocked. It now had almost everything his nursery had, except in a more girly style. Haruhi plopped Tom down on the floor and unclipped the leash from Rosebud’s harness.

“All right you two have fun,” she said moving to leave.

“Yes mommy,” Rosebud said obediently. Haruhi, Topsy, and Micheal all gently waved by to their respective babies as the left, shutting the nursery door behind them.

Tom and Rosebud were left alone in the room, and the awkwardness almost immediately set in. A long moment dragged out as the two silently looked at each other, unsure of what to say.

Tom and Rosebud had the same thought but for different reasons. Tom thought he was looking at a baby, someone who was a baby because they were enjoying the lifestyle Tom had been forced into. Rosebud saw a baby as well. A baby because Tom would no doubt regress even further than he did, provided he got other his disdain for the activity.

“How are you liking the baby life?” Rosebud asked breaking the silence. Tom shot Rosebud a look at the question.

“Eh ah iing eh ah aww” Tom said without realizing the pacifier was still in his mouth. He spit the soother out and repeated in understandable English. “I’m not liking it at all.”

“Ah,” Rosebud faltered a bit, realizing they may have stepped on a land mine.

“Yeah, I’m just so tired of it,” Tom complained. “The constant embarrassment, the lack of personal agency, the punishments, the clothes, the diapers,” Tom hadn’t realized the he reflexively grabbed a stuffed rabbit nearby and started cuddling it as he talked. “Like even just now your mommy just picked me up. It’s so humiliating.”

“Yeah, when Mommy picks you up like that it feels pretty great,” Rosebud said somewhat wistfully.

“I dunno if I’d say great,” Tom pouted.

“I mean sure being a baby has its faults,” Rosebud had picked up some plush building blocks and was absent mindedly stacking them while he talked. “But I’ve never been happier. I don’t have to worry so much you know, Mommy just takes care of that. Plus, the cuddles are nice.” Tom gave another disappointed look at Rosebud.

“Of course, even the other baby is taken in by all this weirdness.”

“That’s not very nice,” Rosebud huffed. “And for the record I’m a toddler. Between the two of us you’re the baby.”

“And what exactly is the distinction between baby and toddler?” Tom asked pointedly. “You’re still in diapers, still dressed like a baby, and you’re hanging on your Mommy’s every word and whim. At least I’m not suckered in to all this.”

“Oh really?” Rosebud said staring at the stuffed bunny Tom was still snuggling. “And you know I’m not ‘suckered in.’ Mommy really cares about me and loves me. I’m sure yours do too if you give them the chance.”

“They love humiliating me maybe,” Tom shot back. “But I think that’s it. You must be a weirdo that likes being humiliated.”

“Well, if that’s not the pot calling the kettle black,” Rosebud said a little offended.

“Don’t be mad cuz I’m right,” Tom was interrupted as one of the plush blocks Rosebud was playing with had clocked Tom rather harmlessly in the head.

“You don’t have to be a jerk about it,” Rosebud, the cause of the hurdled plush projectile sneered. “Besides mommy lets me walk on two legs I bet your mommy and daddies make you crawl. Which is pretty cute with aunty Topsy’s dress showing off your diaper like that. At that comment Tom returned the plush block to Rosebud by throwing it at him.

The alley cats and Haruhi were sitting in the living room. Topsy was proudly displaying Tom’s baby book to her friend. It was a meticulously crafted scrap book filled with all manner of cute and embarrassing snap shots of Tom.

“Look at this one,” she explained as she pointed to one of the pictures. “We caught him actually playing with his little stuffed rabbit. He was so embarrassed.”

“Cute,” Haruhi squeed. “How are the little ones doing anyway?”

Micheal pulled up an app on his phone that showed a live feed of the nursery from a hidden baby monitor. They could hear the bickering between the two.

“Doesn’t sound like it’s going well,” Micheal said concerned.

“Maybe they need a little attitude adjustment,” Butch said rotating his wrists.

“Hold on Butch,” Haruhi gently stopped Butch from getting up. “Let’s give them a chance to work it out themselves.”

Tom and Rosebud were still bickering. Soft plush toys and stuffies flew across the nursery as the two hurled them with their insults. Eventually, without any nearby soft toys, Rosebud tackled into Tom similarly to how he tackled into Butch earlier.

“Ack! Stop it you big baby!” Tom complained.

“I bet you’re ticklish,” Rosebud declared. “Cuz you’re such a baby.”

“What does being ticklish have to do with …” Tom began but he couldn’t continue as he was indeed ticklish. It was difficult for Tom to remain pouty as he devolved into intense giggling.

“I knew it!” Rosebud said panting stopping his attack. “Baby.”

“You’re a baby!” Tom replied playfully launching the same attack against the dog and sure enough he was also ticklish. Tom used the opportunity while Rosebud was laughing to spin around so he was on top of the dog. Tom didn’t get to enjoy his time on top long as the alley cats entered the nursery.

“All right little ones,” Micheal said smiling. “Time for lunch.” Rosebud managed to roll back on top of Tom in order to beat him out of the room. Tom scrambled behind with Micheal giggling as the two passed him.

The mood had turned decidedly playful as the two adult babies hastily toddled into the dining room. Rosebud ran into his mommy who expertly bent down and scooped him before he could collide into her.

“Careful baby,” Haruhi said laughing. “You having fun with Tom?” Rosebud nodded.

“He’s pretty fun to play with. For a baby,” Rosebud looked over to Tom with a smirk. Tom stuck his tongue out in response.

“You’ll have plenty of time to play some more after num nums,” Topsy said as she fastened a pink frilly bib around Tom and led him over to his high chair situated next to the dining table.

“I figured a baby would be eating out of a high chair,” Rosebud sneered. Tom pouted as he sat himself in the high chair and Micheal got to work strapping him in. Almost in response to his teasing Haruhi lifted Rosebud into her lap as she sat down.

“At least I have a chair,” Tom saw his opportunity. “You gotta sit in your mommy's lap.”

“I definitely think that a high chair is more baby than a lap,” Rosebud decreed.

“Children children,” Micheal sighed setting some plated down on the table. “You’re both babies and absolutely adorable ones at that.” Rosebud beamed at the praise while Tom pouted blushing. Micheal proceeded to fill all of the plates of Rosebud and Tom with baby friendly chicken nuggets and french fries. While the adults were given a comparatively sophisticated chicken salad. Tom was about to comment on this before Butch stopped him.

“I wouldn’t complain Tom,” Butch said smirking. “What would you new friend think if he found out we fed you too?” he whispered with a smirk. Tom gulped and started munching away at the finger food without complaint.




AUTHORS NOTE: Another commission chapter for you all. We continue with out Tom & Jerry baby puss saga as Tom has a cute play date with Rosebud. If you're interested in getting a commission from me reach out to me on discord or any of my socials, my user name is the same everywhere. Hope you all enjoy.

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