Hello all! Part 19 of the Working Bois series is here! Wes' wonderful Part 18 cap is here, or use the general tags for all the caps done by Wes and done by me are linked. Additionally, as a bit of a late update, I have decided to post the images for the next caption contest tonight (6 hours from now, roughly) so people can start submitting things before this fun series ends.
Today's cap involves Carli doing something a good sissy shouldn't do...so Mr. Blackstone has to punish his sissy MILF secretary. But how do you punish a sissy who LIKES all the depraved, embarrassing, sexual punishments that you can give? Read on to find out!