Regressing the Bully

By fennyfawk

128K 595 11

Billy the school bully is regressed and adopted by Miss Emily the hottest teacher in school. Worse still for... More

Sentenced to be regressed
Getting to know Mommy?
Salty Milk
The crack of mommy's whip
Grandparents
Cousins
Confessions
Spanked by mommy and daddy
Meeting Harry
Tasting milk
Character Art
Conversations amongst Cousins
Starlet and her boy
Boyfriend or son?

Raising your ex husband

3.6K 26 0
By fennyfawk

"So your mommy used to be your *wife*?" Billy asked Harry for the fourth time. The little one still couldn't fathom the statement. "But how?"

"Ex-wife," Harry corrected his cousin as he tried to get an advantage in the Smash Sisters game they were playing. Billy, Harry realised was stupidly talented at it to the point he barely could keep up with him. "I got divorced around the time Mommy...I mean Robin found me cheating with Vicky."

"Oh," Billy paused his line of thought, focusing back on the game as he swatted Harry away with a heavy attack, ruining his combo and getting his cousin to swear in annoyance. "WAIT, VICKY?" Billy gasped! Their cousin?

"Uh huh, Robin caught us banging on the sex swing with a dildo in each of our butts," Harry replied casually as he went for a devastating hail Mary combo... and realised it connected easily.

"Yay! Eat shit, Billy!" He yelled out loud. Finally! He had been trying to beat his new cousin for over three hours by this point. He looked at him with a big smirk to realise Billy was in shock.

"You slept with Vicky?" Billy squeaked, ignoring the rest of the details as his brain refused to process them.

"Oh," Harry blushed. "Not...really, I never *slept* with her as much as had lots of kinky sex and left before Robin found out. 'xept with Vicky being the dummy she was-and still is- she went around blabbing to everyone about it. And Robin found out. Turns out me and Vicky sleep together more *now* than before after mommy and aunt Alice put us down for naps. Kinda ironic, really."

"B-but..." Billy blushed. How could he be so casual about this? "Isn't aunt Robin mad?"

"What? At cheating on her?" Harry shrugged.

"No, I'm madder at you *swearing* and talking about sex like you're a big boy, Harold Robin Rothschild!" Robin's annoyed tones cut through the air like a whip.

Billy let out a comical squeak. When did aunt Robin come down from the pools?

Harry turned around, shivering at the words. Especially as he knew Robin was just as likely to swap out the metaphorical whip with the real one Aunt Emily had placed in the living room.

"Uhhh... I was just 'xplaining our family dynamics to Billy, Mommy." Harry whispered cutely.

"Hmm... don't think I heard you call me Mommy before, was Robin till now," Robin glared at the two boys wearing their matching purple drop-seat onesies with the family crest embroidered across the chest. Robin in contrast was wearing her red bikini, having been up by Emily's private pool on the top floor getting a tan.

"Because you were Robin then, mommy now," Harry grinned and went over to her for a quick hug.

"Is that so?" Robin smirked when he hugged her. She couldn't help showering her little ex with affection, the cute little thing! Her hand immediately went to pet his hair.

"Uh-huh, and I was past Harry then, not baby Harry you love forever and ever and wanna hug and kiss and do nothing else!" Harry knew this would never work if they were alone...but Billy was with them. Robin always got gooey when she had eyes on the pair, subconsciously wanting to be a good mother to her former husband instead of what Harry referred to as "the vengeful torturer ex".

"Baby Harry gets more than hugs and kisses," Robin gave him 'the look'. "Baby Harry also gets to have mommy's milk. But then again, you're not baby Harry. Baby Harry's not allowed to swear or tell his sweet little cousin about all the icky sex you had with your other cousin."

"That was old Vicky, new Vicky's an idiot who gets me in twouble!" Harry pouted.

"Old Vicky was the same," Robin laughed, scooping the boy up. "And don't try wiggling your way out of your punishment little man." She turned to her new nephew. "Billy, where does your mommy keep your swearing soap?"

"Huh?" Billy blinked. "What's a swearing soap?"

"For washing your mouth when you swear," Robin explained.

"I haven't got any for him," Emily replied, coming down from the pool in her skimpy green bikini.

"Oh gosh, really?" Robin looked surprised at the revelation. "Billy doesn't swear?"

"He's much better adjusted than the rest of our brood," Emily gave her son a fond smile as the little one scurried over to hug her, not wanting to be alone knowing Harry would be punished now. He still wasn't sure if *he* was in trouble.

"I guess it helps that he wasn't a foulmouthed mafia boss in his past life," Robin mused.

"True... except his past life was barely a week ago," Emily muttered thoughtfully. "I just use spankings for any mischief and bad behaviour. Haven't even visited Granny Godricks yet."

"Oh! We must visit them soon then! I could use some good canes and fashionable spanking belts, Godricks always get the best collections." Robin cheered up.

"Mommieee! No need to go to the spanking shop!" Harry cried.

Billy just shivered. Spanking shop?

"We haven't gone there in months Harry, your pain tolerance has gone up in time," Robin frowned. "You know what? I'll test it out. Go bring me the level 3 cane."

Emily felt her son's little hands squeeze her tightly. She smiled, cuddling him close. "I think we can observe this lesson cutie pie," she whispered and sat down.

"Mommy?" Billy asked quietly.

"Hush, now give mommy a kiss," Emily ordered. Billy immediately obeyed her, giving her cheek a nice long kiss as she had trained him over the week.

"Regressed little boys and girls aren't *real* little boys and girls, you know this right?" Emily questioned her son.

"Umm..." Billy looked at her unsurely, not knowing what direction she was going with this. He still had all his memories from being a much older boy and his brain was certainly that of an adult, even though his instincts got childish a lot.

"Don't get me wrong, you're legally considered a little boy and as far as I'm concerned you're my little son for the rest of your sentence till you are older. Buuut... you know and understand adult stuff like relationships, you understand sexual attraction even though you don't feel it that way, right?" Emily hadn't had *the talk* yet and realised this was the perfect time.

"Like your boobies?" Billy questioned timidly. It was weird! He had spent so much time in class fantasizing about those perfect round orbs and now he gets to drink milk out of them? Both Emily and Robin seemed to want to have the boys suckle on them a lot, Billy realised... Something which also seemed to make him feel more childish.

"Exactly. Our milk has many special properties, it helps you deal with pain for one. It's why mommy always nurses you after your spankings," Emily explained. "It's also a bonding experience, mommy likes having my baby on them." She slowly peeled her bikini off, watching Billy lick his lips instinctively.

"Especially as they're sensitive and it gets us off," Robin giggled. "Harry's gotten me off more times suckling my breasts in a year than he ever did in ten years of marriage."

"Hey! Stop telling the boys things like that! You're literally just about to cane Harry for acting like an adult!" Emily scolded her sister.

"Mommy's always been a hypocrite," Harry's voice was low as he had a thin whippy cane in his hand. Two feet long and flexible. It used to be way more painful a year ago but Harry knew that all the milk he consumed drastically changed his pain tolerance to the point it was not even scary anymore.

"Mommy's an adult, I'm allowed to say that unlike you who is supposed to be a little boy." Robin countered, picking the cane from his hand and swishing it like a sword.

"You see Billy, there is an expectation that you boys and girls are to act like kids at all times," Emily explained. "Now...we know that you won't a lot of times. We've been regressed kids as well so it's not like we are clueless about the conversations you have. But generally, an important reason why we nurse you so much is to help with your instincts, help them be more childlike...so you'll avoid this..."

As she spoke she watched Robin bend her boy across the couch and pull down his drop-seat, his chubby butt popping out. "You haven't been having as much milk as you should have Harry. Don't think we haven't noticed. You and your cousins have been avoiding us for weeks so you get to use your big boy brains to cause mischief."

The cane fell painfully across his bubbly buns, getting them to ripple before the boy screamed in pain.

"It's why I bought you to Billy, so you can be an example to him on how good boys should behave."

*Thwakk*

"Good little boys drink their mommy's milk."

***Thwakk Thwakkk Thwakkk Thwakkk***

"Because if they don't, they mentally progress to be a big boy."

***Thwakkk Thwakk Thwakkk Thwakkk Thwakkk Thwakkk Thaakk***

"And big boys get big boy whippings, don't they?"

Billy was now terrified at the intensity with which Robin whipped her son at. She wasn't holding back, her back muscles contracting and releasing as the cane flew with a terrifying hiss before it struck the soft pillowy flesh of her boy's butt.

"The older you act, the harsher we have to spank," Emily guided his mouth to her breast. "So you always try to drink as much of mommy's milk as you can. Otherwise..."

"You are lucky mommy's not getting the family whip out baby boy coz you are still salvageable," Robin continued to whip him, giving sets of six as she counted down to fifty. Which would have been hellish last year, enough to get him to pass out but Harry was now strong enough to take up to a hundred. The level 3 cane was light as a thin switch, perfect in her mind to use for corrections where she can let him have it. It was a good everyday cane now instead of being the special punishment tool.

"Daily nursing little man, five times a day. You will set an example to your cousin." Robin scooped him up and he immediately began crying, preparing his fresh dose of salty milk. Robin let him cover her nipples before she let him feed, moaning as he did so.

"No wonder he gets you off, you whip him so hard he's suckling like he's about to die," Emily teased her sister.

Robin grinned. "Aye, it's how you raise ex-husbands."

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