The Bet

For the next hour or so, the transformed mother and her son played his favorite video games together; it quickly became apparent that she indeed was not only aware of and very into these games, but that she was just as skilled at them as he was. The two were evenly matched in any competitive games they tried, providing each other a proper challenge.

"Yes! Suck it, Jack!" she exclaimed after besting him in another match up. He chuckled at how she adorably threw her hands up and kicked her legs out in excitement. Of course, he also noticed how her ample breasts jiggled slightly with the movement.

He blushed, quickly shaking away the thoughts before coming to an idea to make things more... interesting.

"Hey mom?" he asked her. "How about a little wager to spice things up?"

She looked at him curiously, smiling. Kelly couldn't remember the last time she'd had this much fun, and was eager to keep going. "Yeah? What do you have in mind, big guy?" She had no idea where this sort of language was coming from, but she also wasn't really questioning it either.

"We play two rounds of three different games. Whoever wins the most wins the bet." With his challenge declared, he watched as Kelly grinned and leaned in, intrigued.

"Sounds fun! What do we get if we win?"

Having her, Jack paused for a moment, considering if he really wanted to suggest what he was thinking. After mulling it over again, he answered, "If I win, I want to take you on a date."

That shook Kelly a bit, the regressed mother blushing at the idea, with Jack continuing hastily, "I-I mean, obviously not a real date! It's just, I think it would make me look cool if people saw me going out with such a hot girl! N-nothing weird, honest!"

Kelly was a bit hesitant, biting her lip as she worried that going on a date might be too awkward... but it was enticing, too...

Steeling herself, Kelly smiled and responded, "Fine. But, if I win, you have to be my servant and do whatever I say for a week!"

Jack blushed at her challenge, having no idea what she could have in mind for that. Assuring himself that it was probably just chores, he smiled back and held out a hand. "Deal."

She took his hand and they shook on it. With that, the bet had begun.