Tiffany Chester

Tiffany Chester — commonly referred to as Mistress May during her day-job — is a main character and recent graduate-turned-Dominatrix on Bonding. She is the best friend of Peter Devin, who also acts as her assistant.

She regularly wears a Police type leather outfit during her performances as Mistress May.

Early Life
Little is known about Tiffany's early life, other than she and Pete were high school best friends, but lost contact after having an awkward sexual encounter. She then attended college, where she graduated. Shortly after, she became one of New York's top Dominatrixes.

Throughout the series
Tiffany works at an underground club as a Dom. She recruits Pete, her best friend again after reuniting, to come help her as her assistant and she agrees to give him a cut. She shows him what she does- nothing sexual but anything ranging from tickling men to peeing on them to dressing up as a penguin to wrestle. Her job is unique but she loves it. She even has a "man servant" at home in her house, who pays her to act as his Dom. His name is Rolph.

While working as a Dom, Tiff is also getting a master's degree. She dislikes her professor and most of her classmates, except for Doug who starts to grow up on her little by little.

Tiff and Pete continue to work together and hang out together until they get in a fight and start to drift when Peter confronts Tiff about her control issues.

Doug asks Tiff out and she reluctantly agrees. To her surprise, they have a good time and start to bond, until Rolph shows up in a jealous fit and tells Doug to back off. Tiff is embarrassed of her job and runs away so that she doesn't have to admit to Doug what she does. However, eventually she comes to terms with it and shows up to her master's class in a full Dominatrix suit to show Doug and her classmates what she does.

Tiff and Pete make up and introduce each other to their new significant other.

Tiff and Pete visit the house of a new client, Trevor, who attacks Tiff after locking Pete in the bathroom. Tiff stabs Trevor in the leg after Pete gets out of the bathroom. The two flee together, after police sirens are heard.

Appearances

 * Season One


 * Old Friends, New Names
 * Pete Shy
 * The Past is Not Always Behind
 * Let's Get Physical
 * Double Date
 * Penguins
 * Into the Woods

Quotes
"I’m a dom, not a prostitute. Not that there is anything wrong with that."

- Tiffany