Penny Barber knows the guy who hired her as a matchmaker has no chance with any of her female clients but she decides to have a little fun with him anyway. She strips him naked then bends him over to see if he will let her put a butt plug in his ass. The submissive little loser just says "Yes Ma'am" so she pushes her bullying even further. She spanks his little cock with a ruler and ties his balls with a little white ribbon while making fun of him right to his face. Penny has such a good time playing with his adorable little erection that she even goes so far as to suggest he let her sit on his face. She claims this is all to help evaluate him for matchmaking services but Penny has already decided that she is going to keep this obedient little toy for herself.

Are you excited that your pretty girlfriend is going to watch you get unlocked for strokies today and see your cute little erection for the first time?

"You're gonna regret messing with me over one little prejac joke. You think that video is the first time I heard a rumor about your premature ejaculation issue? Not even close. Your days of embarrassment and humiliation are just getting started." I think it best you know up front, I plan to make you the biggest sissy in the world!

Hooking up with your old bully was not humiliating enough. Your step-MILF had to make sure you her suck his cock live on cam.  

Little compilation of Queen MILF Penny Barber bullying a wimpy guys and bratty girls. Dual spankings, ass kissing, and one poor girl even gets used as a handjob cum rag...

Bullying My Step-Sissy Part 2 will be out next Sunday.

From our archives-Stealing panties from a sorority is a common way to haze freshman frat boys but would a real pledge sneak into the girl's dorm already wearing panties and a chastity device? Penny realizes right away that this intruder is a real sissy pervert, not an unlucky freshman getting hazed. She plans to make sure the whole school knows the truth once she is finished with his spanking, ass kissing, and full feminization punishment.