We can’t believe it! Only 3 more days till our inaugural event! So let’s meet our HOT contestants! ┬áCheck back this week as we reveal additional contestants!


Tom Wray - Sir 1BSir Tom

Tom Wray is 41 years old and lives in Chicago with his husband of 9 years, Jeff Woods. By day he works in content development. By night, he covers kink and leather events for the Great Lakes Den and Windy City Banner.

His fetishes include fisting, paddling, puppy play, CBT, cigars, bondage and torturing with pleasure. He is usually top but has been known to put his legs in the air on occasion. He is also a TV, movie and book science fiction geek and has been known to identify musicals within the first four notes.

ShadiBeidas_HeadshotSir Shadi

A relative newcomer to the scene, Shadi Beidas, 34, has held an interest in leather for the bulk of his adult life. He entered the formal scene in 2015 with a run for Mr. Chicago Leather. A goofball of sorts, he flexes his virtual intellectual muscles far more often than his actual biceps.

Volunteering in establishing gay social activities in the western suburbs has become a passion of his as of late, and you can also find him kicking his heels up with the ChiTown Squares.


SarahSarah Sloane

Sarah Sloane is a leatherwoman from Chicago, IL. She has been active in the Leather and BDSM communities since 1998, and has been honored to serve as an organizer, volunteer, and educator throughout the years. She also writes and speaks on sexuality, gender, and pleasure to a diverse range of organizations, institutions, and events.

When not rabble-rousing, she knits, lifts weights, reads voraciously, and plays as much as she can get away with. She shares her life with her leather family, her boy, her other partners, and her teddy bear, Stuart.


PupScoutPup Scout

Pup Scout is an active member of the Chicago, regional and national puppy and handler community. Identifying as a Husky and an Alpha pup, Pup Scout gets much satisfaction from nurturing and helping other pups and trainers.

He is co-founder of the Inter-Fetish Coalition of Suicide Prevention and Awareness (IFCSPA) and has spoken in many venues and online forums about suicide prevention, including the Jackhammer Complex, Cellblock Chicago and ABDL Cams as a moderator. Pup Scout is the 2014 holder of International Best in Show (Bill “Trooper” Boyd memorial award) from the International Puppy Club. He loves playing video games and practices Krav Maga.


12202464_10154570669074688_1909495262_n (1)Sir Kristoff

Sir Kristoff is first generation Polish descent born and raised in Chicago, fluent in Polish. He has a bachelors in art history and religion, and is currently in grad school for software engineering. He works as a freelance designer and during his free time he explores his kinky side

As a handler, he enjoys offering attention, compassion, and obedience with pup training. His goal, should he win the title, is to be a positive influence to those he trains and create a healthy environment for future trainers and pup/dogs.