So, I'm going to go out for the first time as a boy this Saturday. I have an Underworks TriTop binder that squashes decently, but not decently enough. My growths aren't enormous, they're a 36C and I have wide shoulders which usually makes them smaller. But for some reason I just cannot get them smashed down like they need to be. I've tried the 'down and out' technique but really can't get them to move anywhere..so is there anything else I can do?

up and out.

i second "up and out", its the only thing that works for mine  good luck!

What about the massive cleavage created with "up and out"? (They're perky )

I do the up and out as well. lay flat on my back and put on my binder (it's not like the tritop it's a modified backbrace). It tends to look really good and my chest is bigger than your's.

Another tip is to layer up. I tend to wear a beater over the binder and then under the shirt.

chances are, you'll never get your chest as flat as you'd like it to be.  be creative with clothing-- an unbuttoned button down shirt over a tshirt will help TONS.

well you're not planning low cut tops, are you?  so cleavage shouldn't be a problem, even though a bit upsetting.
second what Mister said, it's the rare guy who can get them completely flat.

I know a couple of guys who manage to get themselves amazingly flat, but I finally saw one guy's "before" pictures (he just had surgery), and he wasn't very big at all.

A lot of factors contribute to the overall look. Size, shape, how dense your tissue is (mine was pretty dense), what kind of binder you have, how you manipulate the appendages underneath the binder. You might even need two binders to get the best effect. Not much fun in the summertime, but it's something to consider. And what Mister says about layering is good advice.

Also, remember not to look DOWN at your chest--look at it head-on in the mirror. The bumps always look more prominent when you look down. Having the unbuttoned shirt as your final layer will also minimize the bumps that remain in profile.

Let us know how it goes, okay?