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Tag: chastity

Covered In Panties Penny Barber

It is finally time to let my little pantyboy out of chastity. This sissy is especially lucky because I brought her a pretty pink cocklette ring that says PRINCESS! Once the pantyboy is unlocked I cover her little princess stick […]

Sissy Cuck Begs To Wank Penny Barber

Yes, my date went very well little sissy. Did you enjoy waiting here all locked up for your Mistress? Maybe I should give you a treat for being such a sweet little sissy cuck. How about a few seconds out […]

Mistress Cums First Penny Barber

You should realize that My pleasure always comes before yours, silly sissy. I am going to give you a little treat today though: I am going to let you play with my panties after I finish playing with myself in […]

Your New Sissymaid Uniform Penny Barber

Any sissy lucky enough to serve as my maid will be held to strict uniform requirements. From your pink chastity device to your frilly cap, everything had better perfect or else. it is already challenging enough cleaning in a butt […]

Cowgirl Sissy Penny Barber

Is my little sissy excited to dress up as a cowgirl for all of Mistress’ friends? I promised that you could be the entertainment for my buddy’s bachelorette party and I think that a little cowgirl outfit is the perfect […]

Chastity Humiliation Tasks Penny Barber

Letting little sissies and pathetic pantyboys out of chastity is not something Mistress does without good reason. If you want to play with your little sissy stick you need to convince me by showing just how willing you are to […]

PENNY BARBER – COVERED IN PANTIES

It is finally time to let my little pantyboy out of chastity. This sissy is especially lucky because I brought her a pretty pink cocklette ring that says PRINCESS! Once the pantyboy is unlocked I cover her little princess stick […]