Illinois LeatherSir 2007 Rob Welcher and Illinois Leatherboy Joe
Alegrett. (Chicago Den photo by Tom Wray)

Rob Welcher won the Illinois LeatherSir 2007 title and his partner Joe "Bratty Boy" Alegrett took home the Leatherboy title this past Saturday night to an excited crowd at Chicago's Jackhammer bar.

Things started off with emcee Tom Stice introducing the judges, scoring some zingers off the judges and audience in his usual style.

After the introductions, the main contest kicked off with serious questions and fantasies. Sir Josh was the first with a question on what he thought would be most important for the winner of the title.  Josh felt that bringing new people into the leather community was at the top of the list. He felt the current members of the community needed to educate, be respectful and help for those wanting to learn. Of course, that didn't mean that people couldn't also have fun.

Master Wes started the fantasies with a bondage scene with his boy, Leatherboy contestant Joseph. Boy Dan had the next question about his biggest challenge, which for him would be drying off before work, which explained his watersports scene during the fantasy.

Master Z, co-founder of the Chicago-area Leather SINS organization and a board member of the National Coalition for Sexual Freedom spoke next. He thanked everyone for their support and especially the Windy City Boys Troop and Jackhammer bar who were donating proceeds from jello shots, the cover charge, raffle tickets and the downstairs bar to the NCSF.

Joe Alegety's scene was a flogging, set to Justin Timberlake's "Sexyback," proving it is possible to dance when tied to a cross.

Wes's questions was what could be the most difficult for his title year. His response was on mixing leather and politics and getting people registered to vote and politically active. Joseph's biggest challenge was uniting the community and working together.

Rob Weckler's scene was next and was arguably the most intense of the night. He, with the help of Joe and a boy who also happened to be a medical student, did a temporary peircing scene, using four inch hooks. With a low-pulsing theme, two hooks were pushed through the skin and muscle of Rob's back, with the hooks attached by a twine to a frame where Rob pulled against them and eventually lifted his legs up to be suspended by them. Tom Stice summed up the reaction of the roaring crowd by saying, "Wow."

Joe said in his speech that as Leatherboy he would work on education both of the leather community and safer sex. Rob followed up with speaking on his greatest challenge of being true to himself if he won the contest.

After the jockstrap portion of the contest, the outgoing titleholders gave their stepdown speeches. Outgoing Leatherboy Chris "Devilpup" Steuber gave a quick speech thanking everyone for their support in the past year and for coming out for the night. LeatherSir JoeE Arteaga, who went on to win the Great Lakes title, played a DVD as a stepdown, though there were a few technical glitches with it.

Rob and Joe will go on to represent Illinois at the Great Lakes Leather Weekend event in Indianapolis this August 24 through 26. In past years, Illinois has done well with the LeatherSir contestant winning in the years that Illinois has sent someone to the contest. Joe will have a challenge as Ohio has dominated the other contests for the past few years.

The Chicago Den will have video of the contest posted on the blog within the next day or two. Photos of the weekend can be seen on the photo album here.