Daddy Sky has previously served as Great Lakes Ms. Leather Pride 2017 and Ms. Illinois Leather Pride 2017. She’s a Chicago based Leather Dyke, whose personal lust for Kink, Fetish, and Leather Lifestyle spans more than 28 years.
In 2005, dissatisfied with extremely limited play and BDSM Arts education options geared specifically towards Women, Gender Non Conforming persons, Enby persons, and Transfolk, Sky created Vespertine Chicago. She has dedicated herself to a core mission of fostering Kink and Fetish in everyone she meets and of stewarding the next generation of healthy, Sex Positive People, by creating a safe space in which Queer Women are centered and may play, learn and grow. A portion of each event’s proceeds are donated to local charities.
Her professional life in Kink and Leather found her serving members of The Community for ten years by helping them navigate their path while working at Mephisto Leathers, and Leather 64Ten. Daddy Sky then spent 4 years working in Personal Pleasure and Sex Education at Tulip Toy Gallery. She is very proud to be back at Leather 64Ten serving the Leather and Kink Communities directly.
Daddy Sky is a Supporting Member of the Leather Archives and Museum, and also volunteers at International Mr. Leather Weekend. She has been a Judge, Tally Monster, Den Daddy, and Event Host. The Sky truly is the limit with this Daddy.


Kelvin Davis has been in the scene for a long time you might say as he grew up around leather and kink. Being the son of a policeman, he fondly remembers sitting on the laps of the officers when he was a kid; the uniforms, creak and smell of leather, handcuffs and jail cells, all were a part of his childhood. As for other kink, first aware of the affinity for bondage came from watching Wild Wild West (no, not the movie, the TV series). His career of being a fireman, paramedic, HAZMAT specialist and instructor just added fuel to the fire.
Kelvin’s title journey consists of being 2015 Mr. Ohio Leather & IML Class of 38. His former titles are Mr. Ripcord Leather, and Mr. Gulf Coast Bear. He has been on judging panels for Detroit Leather Bear, Mr. Argos Leather, and Northwest DNA. He has worked with many charities fundraising including Leather Heart Foundation, and the McAdory Fund and Toledo Friendly, an outreach of Mr. Friendly. Kelvin is a member of Chicago Hellfire Club as well as membership in Titians of the Midwest and FLAG (Fits Like A Glove). He has presented classes at Inferno, S&MU, CLAW and TriState on a variety of classes from Dungeon Safety, Toy Making, Violet Wand and Fire, Blood Sports, Knockout Play and more
Kelvin has a 14-year relationship with his partner in crime, a collared pup, and can be found taking applications for others. When not traveling for events or busy teaching, he enjoys not so quiet evenings in the house dungeon.


Luis first started his leather journey in 2010 while visiting a friend one evening for a casual conversation and later that evening he tried on his first harness, leather jock, chaps and vest. Luis is Mr. Chicago Leather 2015 and competed at IML37 where he placed in the Top 20. He was co-founder of Chicago Leather Community Outreach and Vice President of the Chicago Band of Brothers. He has served on the production team for Mr. Chicago Leather and has been a judge, tallymaster, and has helped with several contest throughout the Midwest. He is currently on the board for Team Friendly Indiana. He is also co-owner/producer of the Mr. Indiana Leather contest. Luis lives in Indianapolis, IN with his husband, Sir Eric Masters and their two fur babies.


Will Baker is the consummate host, baker, and ethical slut. As the co-founder of the American Society for Sodomy and Fine Unaged Cheeses (ASS-FUC), he enjoys combining cheese with sex and hosts well catered orgies where the hours of sex are followed by a Julia Child meal. Will enjoys building relationships with people and sharing the incredibly important message of U=U.


Jason’s first foray into the leather community began four years ago with IML. Since then he has grown into the leather community by attending new events, networking with amazing leather people, and learning about the wide variety of the fetish life. His time as Mister Iowa Leather 2019 has been enlightening and a great opportunity to continue to grow personally and help others that like him hadn’t been involved in the community. Jason spends a lot of time in the gym as a way to both release stress and physically feel better; always searching for new ways to keep himself interested. His job has allowed him to travel to places around the world to make a positive impact on the lives of people in need. He tries to live his life by his motto: Learn, Grow, Smile.