Ms. Leather Pride Contestants


Daddy Sky Cotton

Sky Cotton is a Chicago based Leather Dyke, Daddy, who’s personal lust for Kink, Fetish and Leather Lifestyle spans more than 27 years.

In 2005, dissatisfied with extremely limited play and BDSM Arts education options geared specifically to Women and Transfolk, Sky created Vespertine Chicago. She has dedicated herself to a core mission of fostering kink and fetish in everyone she meets that shows a genuine interest in learning Erotic Arts; and of stewarding the next generation of healthy, Sex Positive, Queer Women, by creating a safe space in which they may play, learn and grow.


Pup Contestants


Pup Sharp

Pup Sharp has been a part of the pup community for over 8 years. He credits the puppy lifestyle for not only stabilizing and enriching him as a person, but also for introducing him to his husband.

Pup Sharp is extremely passionate in promoting not only the stigma-free crusade for HIV awareness, but also the sense of community and comradeship the pup community can provide. He hopes to continue to promote and spread this awareness. He is also an active musician and composer eager to incorporate LGBT, kink-friendly, and pup-centric ideals into his work.


Pup Xolox

Pup Xolox (pronounced Zo-los) has been an active member of the Kink Community for the past few years. Not easily missed with Bright Green Mohawk or Gear. He has been volunteering his free time at local and out of State Events  as Pup or Sister. He is a member of The Abbey of The Windy City Sisters of Perpetual Indulgence and Chicago Pup Patrol. Whether he is serving his country in the US Navy or is giving time to the community, this Pup is excited to continue his growth in Chicago.



Pup Ikos

Pup Ikos was Born and Raised in the Northern Illinois Area. He resides in Rochelle Illinois. He has been in the leather community since he was 22 years old. He has witnessed a lot of in his lifetime. He has been involved in the drag community while living in Denver, Colorado.

The reason he is running for Illinois Leather Alliance Puppy is that he believes this is his time to make a difference. He believes that he can enlighten the different area of Illinois, such as Rockford, Joliet, Peoria, Springfield, etc. He plans on working with other titleholders, and being a pillar of the community, alongside other of members of the community.


Trainer Contestants


Daddy Eos

Daddy Eos was first introduced to the kink community in the Fall of 2013 and one of the first ones he was introduced to was puppy play and fell in love. During his time he has been able to explore a wide variety of kinks and meet some beyond wonderful people. In the late Spring/early Summer of 2016 is when he first experienced little play and quickly became a Daddy. Daddy Eos has an educational background and knows how important knowledge really is and wants to make it as accessible as possible.