Ah how nostalgic. We had a drag DDR tournament once, and I had to help quite a few boys. Hahaha, it was quite fun.
Just like Lylysa said, what look do you hope to achieve. Do you want a natural look or dramatic look? Do you want to look like a women or just, well, a men wearing a women make up look? Also, if you would like product recommendations, then what's your budget approx?
Depends on those things, then we can start working on things like, if you want to disguise your stubbles then what kind of foundation/concealer to use, or easy to use eyeliner/lipsticks. Technique matters for dramatic looks, so practice make perfect (I like to do a test look before I shower, so that I can make sure everything gets washed off.
Images from Refinery29. I love the 1st one. He look better in drag than I do when I'm dressed to the nines D=
Well, first thing's first, you have to determine what type of look you want to achieve.
The world of make up is so vast that we in the forums can ramble and list of dozens upon dozens of products to use.
Not to mention the world of make up in terms of technique, style, and application is different and can vary by the genre, such as natural/every day, beauty, retro/period, special FX, drag/female impersonation/male impersonation, etc.
Throw some specifics out there and we better direct some advice!
I just wanted to add as a side note, the styles for make up for a crossdresser can be very different from someone in the world of drag.
Though they can go hand in hand with one another, the term "crossdress" and "drag" don't always mean the same thing. I've worked with clients who are crossdressers and those who do drag and I find that crossdressers aren't always looking for looks as extreme or severe as those in the drag world.
Drag implies and brings to mind more of an extravagant and embelished aspect of make up, while crossdressing can merely be someone who sides more with the female gender or things more commonly associated with being female.
Drag is a performance where a male takes on a larger than life, or different persona, they may or may not always identify with being a female impersonator as sometimes drag is so extreme and over done that it's clearly made to be a show and presentation of a man wearing wild make up as opposed to a man who wants to be considered or viewed as a woman. Though there are many female impersonators/illusionists in the world of drag, it's just a small facet of those who participate.
Crossdressing is similar in that aspect, that there are many facets of that world. There was one client I worked with who clearly was male, regardless of how high his heels were or what kind of dress he put on. On occassion he wouldn't even wear a wig, he would just wear female clothing. I would do his make up and he never asked for anything bolder than maybe a red lip or some glittered liner if he was going out for the night. His intent was never to look 100% naturally like a woman, but rather just have his outer appearance identify more with aspects of his inner persona and the gender he identified more with.
Just wanted to put this out there in case it helped with offering suggestions for make up/application techniques, and maybe, to @crossdresser, this can help bring out more specifics and expressing what you want!