My dear trans brothers who are just starting to shave, especially you who have never taken a razor to your face before! I am taking your hand right now. I am looking you gently in the eyes, and giving you a thoughtful expression. We are connecting. We are connected now.
Now that we are connected - DO NOT SHAVE AGAINST THE GRAIN. I know it is tempting, I know, I KNOW, I have compulsions regarding hair on my face, I KNOW. But it will start a cycle that you will not like. Let me explain.
You are (most likely) used to using a razor on your legs. The skin on your face is not like the skin on your legs, and your facial hair is not like leg hair. You can take a razor to your legs, swipe against the grain with a dull razor on two weeks of growth and be mostly fine, because your legs are straight and the hair grows largely in one direction. But your face? Your facial hair does not abide by the laws of body hair. It will grow in whatever direction it damn well pleases, and your face is MUCH more sensitive, so the drag of hair on a razor can HURT, even if you don't nick yourself. You also have a biiiiiig curve from your cheek to the underside of your neck. This curve is specifically designed to fuck up your day if you are used to shaving your legs. You think that you can just follow the curve with your razor and you'll be fine. That's the devil talking. You need practice.
So what happens is this. You go to shave your face for the first time. You take a razor, put it to your neck and swipe up, expecting it to take a couple minutes at most. Your razor catches all the coarse hairs that have been growing there and tugs on them because you aren't holding the razor at a flush enough angle, and you possibly nick yourself. Now your follicles are inflamed, and your face is still not smooth. If you are unlucky or just impatient enough, you give it another pass, causing the same problem. Your face is still not smooth, and now it is inflamed and painful to touch. You now have to either wait for it to heal and try again or grit your teeth and keep shaving over it, possibly causing scarring or ingrown hairs (both of which suck). Those inflamed follicles will hold the hair at a different angle from the swelling, which will cause more razor burn when you try again. The cycle continues.
So what you need to do is this - you need to spend some time with your face, running your fingers along and finding out which direction the hair is growing. The hair along my neck actually grows in sideways so I have to shave it at a careful angle or risk it being uncomfortable, and I promise you've got places like that. Find them all, commit them to memory, and then shave with the grain of your hair (in the direction the hair grows). Commit to shaving like this for several months. Consider learning to use a safety razor for better control over what's happening, since you'll control the angle of your blade instead of having a swivel.
When you have managed to get a consistently close shave for at least a month you are ready to go back in and make a second pass (a SECOND pass - always shave as close as you can WITH the grain first, then go back with more oil and more lather) at an angle or against the grain if you really feel you need it. You now have enough control to not cause as much trouble for yourself if you do nick yourself or cause some inflammation. It has taken me almost six months of shaving to feel comfortable with a razor in my hand, and another two months to feel comfortable enough to write this post. Learning to shave properly is work, and it can be hard work, but it is also very rewarding in the gender euphoria and looking fly as hell departments.
Now go, fly free. I am releasing your hand. We are still connected by the bro bond but you can like, walk away and stuff now.
(Please use a new razor on your face and change your blade every couple of shaves, the fewer blades and sharper blades possible the better. Learning to use a safety razor is worth it, if only for the ability to switch blades every time you shave for pennies.)
EDIT: If you do not or cannot trust yourself with a safety razor, whether because of unsteady hands, mental health concerns, or triggers, please do not feel obligated to or attempt to override that safety concern. I love safety razors and there's a whole culture around them that can be very enticing, and also very isolating. You are not lesser if you are using cartridge razors or electric trimmers, for ANY reason. (Thank you to @fenmere for this caveat, it's an important one)
