Emily,
Welcome to the forum. You'll get loads of advice here, some you'll welcome, some less so. That said all of it will have your best interests at heart. I think it's fair to say that anything you've considered, someone here has been there before you so the best piece of advice I can give is heed any warnings offered.
I do want people to see my ****ty dressing and enjoy imagining that they would think I’m a prostitute and what they would do to me What they may do is kick the living daylights out of you or worse. Somewhere quiet and dark that you can walk in is also somewhere a group might go to do drugs etc. Most here will admit that they're first ventures out were usually at night and I'm guilty as charged. What I've learned along my CD'ing journey is I'm far far safer walking around a mall in broad daylight than anywhere else in the dark.
Darkness is viewed as a cloak that we can hide under. Crooks and nerdowells see it in exactly the same way.
As others have said finding a group to attend is by far your best option. I've attended a group that meets in the Gay village in Manchester (UK). There are CD'ers in all the pubs who are in heels and short, tight dresses. All glam'd up, jez some of them have such great legs, but no-one cares. They're free to chat, strut their stuff, all in perfect safety there being at least 2 big bruisers on each door to keep undesirables out.
I can appreciate just what a huge step going from alone in the dark to mixing in a busy bar is. However, once you take that step you'll never look back.
Do your homework. Check out where you want to go. What's the parking like, stuff like that. For your first few times, stay stone cold sober. Until you're familiar with what goes on and know a few faces, staying sober ensures you make the right choices. Being chatted up can be flattering, responding so that the guy thinks you're "looking for love" but then chickening out at the time of intimacy is also something to be avoided. So if you want to explore that side of your character, be clear to the other person you're position and that you're uncertain of your sexuality.
The most important thing here is staying safe. You have years ahead of you to find your way. Don't rush into it and make mistakes you'll regret for the rest of your life.