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I believe there are indeed glass paint markers, and I think you could probably use stencils for the bigger parts like the dresses.
http://www.michaels.com/Glass-Painting-Basics/ae0034,default,pg.html
Michaels says it has glass paint markers, at least.
I've done the hand-painted glass once and it's pretty easy, you paint it on, put the glass in the oven for a cold start and then set the heat and bake the paint on. I didn't have any problems with the glass breaking in the oven but I know it can happen, especially if you put the cold glasses into a hot oven.
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I love these glasses I saw on pinterest/etsy but they are pretty pricey for the really nice ones and I have 8 people in my bridal party... I would love to have these for the wedding so I want to try to make them mysef first, or at least try one- Do they make glass paint markers? I know I couldn't do this with a paintbrush because I don't have a steady enough hand...