It seems likely to me, having planed and sanded a few boards in my life, that the saying originate in the wood shop, where going against the grain of the wood generally results in a poor result. At best the surface ends up being furry, with the ends of the grain sticking up, or at worst whole slivers of wood will get caught and will pull away from the surface.
In the context of this blog you might assume that "going against the grain" means the usual, of acting against societies' norms or your own usual tendencies, and therefore being uncomfortable in those actions and if so, you are partially correct.
More often than not these days, even though I am always cross-dressed as a male, my public behaviour is tending to be whatever I want it to be. I like to be comfortable and as natural as possible, so I am pushing the envelope of traditional male appearance just a little, and traditional behaviour quite a lot. I get looks and that is fine, because going against that grain suits me.
So many of us are wrapped up in finding the right voice, the right look and generally doing what we must to fit in as a woman. In my case, working very hard to find ways to stay with my partner who is slowly getting used to the new person in her life means not forcing the situation and knowing that soon enough I too might be concerned with those things we call passing. A compromise is working for now. She knows what is going on, and so do I. We love each other in many ways, so in this case there is no going against the grain. We are each finding the grain, and working within that as best we can.
So what about the title? When it comes to facial hair, a smooth smooth feel is what I must have all day long, which means using a fairly expensive multi-blade razor, and shaving over the same area several times in different directions. The first pass usually does not matter, but the second time is against the grain, in whatever directions that happens to be. I will keep adding lubricant (usually just good soap) and pulling evenly until my hand can pass over the whole area and feel no 'grain' at all.
Some who come here regularly might recall that hair is an issue for me in other places apart from my face, so late last year I bought an epilator. The instructions said it was for leg hair, but come on, hair is hair, right? Well, the first time any area has the hairs yanked out, they are not happy about it, but none can resist a persistent applications of this machine. I got through it because I really really wanted to; pain be damned, those things were coming out. I will not catalogue the various areas other than legs where that machine worked just fine, but lets just say I reluctantly stopped just as I was contemplating moving to my face, as tempting as that is.
Oh, and by the way, go against the grain. The only hairs that will defy those rotating tweezers are the ones that are lying right against your skin. Rub your hand back and forth a few times to get them to stand up and say goodbye.
If going against the grain on my body or in my life is what I really know I must do, then I think deeply, listen to my heart and head and I do what they tell me is right for me.