Regressing the Bully

Salty Milk

Billy looked at Emily with a blush as they walked around her apartment. "Breastfeeding?" he questioned, still appalled by how cute his voice sounded.

Emily looked over at the boy with a smile. She had taken Billy to her place by their school, ready to move into the mansion in a week or so. She had planned on splitting time between both places as time went by, wanting him to still maintain that bond with him and not be seduced by the power

"I thought you were quite obsessed with my breasts when you were older," she teased.

Billy just blushed. They looked much bigger now and she wasn't wearing a bra under her top! Emily has caught him staring at her cleavage on more than one occasion at school, even paddling him for the offence. But now...

"It feels weird Miss Emily!" The boy whined, pulling his purple silk pyjamas she had him change into embroidered with the family crest. Emily herself had matching robes that clung to her hourglass frame.

"I grew up with it sweetie, it's quite normal with your cousins," she leaned to pick him up, carrying him to their bedroom. "And it's Mommy now, do you want me to take a strap to you to make you remember it?"

The boy immediately shook his head, very much like a little boy his size would have. Billy remembered Miss Emily during detention, folding up her sleeves and grabbing her thick strap as she had him bent over her desk. She always whipped him to a blubbering mess, his bottom red and welted and often plugged with a thick ginger root. She wasn't authorised to give more than a quick hug however so Emily was happy at being able to snuggle with him now.

"I'm still gonna get spanked now aren't I?" He complained, nuzzling into her as he took in her perfume.

"Yes. But it's just going to be my hand for now," Emily carried him to her armless spanking chair by the side of the bedroom just in front of a full-length mirror. Billy shivered, seeing the pair together now. He was no longer the big strong man who towered over Miss Emily but a small cute, chubby runt! And she looked so hot, so beautiful! Beautiful and terrifying at the same time.

He hugged her tightly as he felt her fingers on his pyjama bottoms, pulling them down and exposing his very soft, fleshy baby butt. "A very long cry over my knee should get my baby into the right frame of mind."

She took her seat and bent him down over those extra long shapely legs. Her hand began to knead and squeeze his butt. Billy could see her smile getting wide in the mirror as she did so.

*Whap!*

"Owwie!" The boy squeaked as Emily began a quick crisp lesson, absolutely *loving* how cute and soft his butt was! She liked to thrash his sexy athletic butt back in the day...well, as early as a month ago...but this?

This was perfect!

It helped that he was finally hers, she smiled. Her boy, her little man who she would raise on her breasts. "Ouchie owie owiee!" The cries were getting cuter and raspier as she smacked and smacked, happy he still retained his adult resistance to a hard lesson.

"Cry it out, buddy boy. A Rothschild boy's spanking from his mommy only finishes when you have enough tears to soak mommy's breasts." She paused, spreading his cheeks as she began spanking in between them on the tender inner curves.

Something that got the boy to howl like a banshee. She always spanked him there, using a special groove strap at the end and leaving him feeling raw and tender. And that was as a huge athlete!

"Mommie I'm sowiee!" He began to beg and plead as Emily continued to spank for another full two minutes before she stopped. Little Billy found himself sobbing into her magnificent bare breasts as his tears flowed into her nipples.

"Our boys drink salty milk," she whispered into his ear, letting his lips wrap around her nub as he tasted the sweetest milk he ever had mixed with the salt of his tears. The boy suckled himself to sleep, finally realising the truth. He was Emily Rothschild's little boy and his life has changed forever.