Yes

You think Will has had enough ass smothering - for now. You untangle your hands and let go of his head.

As soon as you do that he takes his head out of your ass and frantically screams "I give. I give Ashley please stop!" He is panting from lack of breath. You know that you should let him go at this point, but something takes over you. You are no longer the same person that started this match. The feeling of having someone completely at your mercy begging you to stop has given you a massive power trip and made you lose all empathy for Will.

"Beg more" you say, in a bratty voice.

"What?"

"You heard me, beg more!"

"Are you crazy? I'm not going to beg."

"Too bad then, I guess you just need more time under my ass." You hear Will shouting a chorus of no's as you grab a hold of his head and return him to his previous position wedged between your ass cheeks. Again you hear his muffled cries, this time more frantic than before, but you don't let go as soon as last time. You hold this position for almost 30 more seconds until you hear the cries decrease in volume and his legs slow their movement, finally letting go just moments before he passes out.

"Ready to beg?"

"Yes Yes oh god yes anything but more smothering."

"Make it good, or else!"

"Please Ashley don't smother me anymore. You proved you were the superior wrestler in this match, and you were able to submit me with your ass-"

"My sexy ass!"

"Yes yes, your beautiful sexy ass! I submitted to it. You are the superior wrestler."