Regressing the Bully

The crack of mommy's whip

"Awwwwaahh!"

Billy's cry pierced Emily's heart as he struggled to keep his position over the chair. His raw, red behind wobbled as the heavy stripe of her whip bloomed across his soft tender flesh.

"Keep your eyes forward Billy boy, Mommy has four more to go."

"Oowee but mommiee!" Billy couldn't believe how much...well a *whip* was certainly going to hurt, he realised. A proper whip coiled up braided leather that Mommy produced with a reverence that morning. The family whip, or at least the replica of the one which would be used on him regularly once he made it to the royal mansion.

"Shush, I promised you six of the best young man, you just got two." Emily took a deep breath and swung the whip around her head and bought it down with a graceful arc, the whip biting deep into his soft butt and have it wobble as if it were a water balloon.

*CRACK!!!*

Her boy's cry was excruciating for the new mother. She needed to give him two spankings a day, one at bedtime and one in the morning and unfortunately for her little one, the whip was delivered that morning. A special instructional tool, as her mother put it.

"When you get to our mansion you will be whipped, baby boy. Bared in front of your grandmother and have your little bummy striped till you don't have any tears left."

*CRACK!!*

Billy's throat was getting just as raw as his butt as he screamed his head off, watching his drop-dead-gorgeous Mommy in the full-length mirror. Thin and busty, she wore just a black two-piece lingerie with the family crest, a dragon wielding a long whip on her left breast. For Billy the iconography was apt. That was exactly what Emily felt like as she laid the fifth stroke.

*CRACK!!*

Emily watched the lines bloom on his bum. She had warmed him up with her palm, just like she did last night. Billy had only been expecting that, she knew. He had hugged her tight and cried into her chest and promised he'd be good and was an absolute angel... She so wanted to just baby her little man, her cute little angel.

"Last stroke bud," she spoke clearly.

*CRACK!!*

Emily sighed as she looked down at the whip. The deed was done. His butt was given a quick coating of fortification oil, something which helped to prevent the skin from breaking and dulled a fair bit of the pain. His endurance to a whopping was kept at an adult's level during his regression so Emily had no qualms about whipping him hard. She was raised the same way and... It was par for the course being a Rothschild. Her brother and sister probably had it worse than Billy did. They were regressed for much worse crimes.

She coiled the whip back up and put it back in its ceremonial case. Hopefully, she wouldn't have to use it for punishment anytime soon. Hopefully...

"The whip is something bad boys and girls are introduced to the moment you are taken into the family," she explained, walking over to her baby and slowly releasing him from the soft cuffs she used to bind him over to the side of the bed. She knew he wouldn't be able to keep position otherwise.

"In two months when we get to the mansion, Grammy and Gramps will have you be whipped in front of them. Eighteen lashes on your bare bum by Mommy, just like today. So consider these lessons practice for then" She moved to free his hands and flipped the boy over and smiled at the tear-stroked face.

"Mmm that's a lot of salt for your milk," she cooed, thumbing some of the tears and unhooking her bra, rubbing the tears on her nipples. Billy watched the scene both in awe and in fear.

What did he just get himself into?

"Mommy..." He mouthed...though the voice cracked under stress.

"I'm here baby, I'm still mommy even if I whipped you like that," she picked him up. Whippings were always given by the Rothschild women in their undies and they always nursed their victims. "Now have your breakfast, Mommy usually will have a looot of milk built up after a long sleep."

Billy latched onto her breast immediately and began suckling, his parched throat loving the warm yummy milk as it flowed down his oesophagus. He felt her hand tracing the welts and cried immediately.

"Sssshh, it's okay, Mommy's here. The oil will help with the pain, you'll be back to normal by the evening," she reassured him.

"But you'll whip me again then!" Billy cried at the sudden realisation, a drop of milk dribbling down his chin. If he's healed up so quickly she could do this over and over!

Emily just laughed. "Relax, your bummy's free for at least three days from the whip," she wiped the milk off and pulled him back to her breast. "It is common back in the mansion, yes, but you won't be getting it as bad as your cousins do. And here mommy's just gonna be using my hand most of the time.

She felt his nursing be more steady as she held him, relaxing in her arms. "You can nap a little baby, whippings are stressful the first few times," Emily said kindly. The young boy just gave a nod. Two days ago he was a man and now he was...

Well, Emily was still hot. He was lucky in a way, being able to get this intimate with her...though not in the way he had fantasized for months. This was...

Well, he couldn't think too much, the pain was throbbing by this point and her milk had this hypnotic property. He was soon drifting off, memories of mommy with her whip crystallizing in a corner of his mind knowing it will be one of the defining images of his new childhood.

Pain and love.