33 Curious guy looking for help to crossdress for Halloween

Normally I would have posted as alpha but recently i have wanted to connect with someone that is down to help me crossdress (hopefully decently) for Halloween, if I end up having a good time, I think i would be open to continuing to do it with some regularity. I want to go out around Chicago, maybe boystown or a club or bar, or a costume event somewhere dressed up but have no real experience with makeup or anything. For me it would awesome if I had a group or someone to do this with.

I look like a normal masculine guy in my day to day professional life, 6ft and 195.

Trying to post early to connect and hopefully actually pull this off.