Twenty-five years ago, Sky Cotton struggled to find her place in a male-dominated leather scene. Now the self-identified "Leather Dyke" has made a name for herself as a sex educator, leather and chainmaille artist, DJ and performer who promotes kink and fetish awareness.
Cotton's first introduction to the leather scene came when she met Benedict Michaelowski, a leather daddy who worked at former Chicago leather bar Manhole. Michaelowski introduced Cotton to Vince (last name unknown) and Deitard (last name unknown), whose basement had been converted into a dungeon for fetish parties.
At her first dungeon party, Cotton was surprised when a group of police officers entered Vince and Deitard's basement. Cotton rushed upstairs to tell Michaelowski that the party had been busted.
Michaelowski replied, "Honey, it's uniform night."
Michaelowski explained that Vince and Deitard were uniform fetishists. The men showed Cotton their uniform collection.
"They had cop, fireman, postal worker, UPS, FedEx, repairman, priest, cardinalevery single uniform possible," Cotton remembered. "I had never seen anything so beautiful in my whole life."
With her new kink-oriented friends, Cotton began attending International Mr. Leather, a contest and conference of leathermen held annually in Chicago since 1979. Cotton fell in love with the event, but she was dismayed that the only women's event the conference offered was a "women's meet and greet."
"If you want to meet someone, you can meet them, you can greet them, but if you want to go and play, only boys get to do that. I wasn't happy with that."
In August 2006, Cotton began working at Mephisto Leathers, now Leather64Ten, located in Rogers Park. Studying under leather designer Paul C, Cotton found a home for herself and the perfect location for an event that catered to women's interests.
In the spring of 2006, Cotton cleared out the basement of Mephisto Leathers and advertised Vespertine, a women's play party where queer women and transfolk could engage in BDSM (bondage, discipline, sadism and masochism) and safe and consensual scene play in a safe environment.
More than 60 women attended the first Vespertine, an annual event that coincides with International Mr. Leather.
"With Vespertine, my mission was to create a safe space for any woman who wanted to find something out about herself," Cotton said.
Vespertine has grown to include more demonstrations and BDSM arts education. Cotton hopes to reach feminists who struggle to find balance between their belief in women's empowerment and their interest in kink, particularly submission.
"The submissive [in a BDSM scene] is a submissive by choice," Cotton said. "For me, women's BDSM and women's play is about women being able to experience for themselves non-traditional roles. It's their way to empower themselves."
For the past four years, Cotton has taken her mission to broaden awareness of kink and fetish to the stage. Cotton performs with SS-Triple-X, a "fantasy fetish" performance group that brings queer, body-positive burlesque to Chicago audiences.
As a mentor to the next generation of queer women, Cotton hopes to show others what the leather community has given her.
"The leather community gave me a place where I felt I fit," Cotton said. "I've always bridged all groups and ages and generations, because I don't really take no for an answer. I just stick my hand out and say, 'Hi, I'm Sky,' and in the leather community, they love that."
Text and photos by Malic White.
THE STATS
Age: 49
Neighborhood: Uptown
Hometown: Niles, Ill.
Relationship status: Partnered with a girlfriend of two and a half years
Pets: Two cats, Doe and Booty Pants
Little-known fact: Cotton is an avid gardener and chef.