that is hot. You should cum on his pillow too. Never thought about toothbrush, fucking hot!
On the subject of bullying or humiliation, have you heard of 'petticoat discipline' ? y'know, dressing him like a girl as punishment. You could also make him wear a collar and walk around the house with on a leash, make him bow at your feet and kiss them. You could also fuck her outside the door to his room, make her walk around with lingerie, etc. I wish we could have a picture of you three (with faces blurred, of course).