I have a friend who has recently decided to explore cross dressing. This is something that he has obviously been thinking about for a long, long time, and I am excited that he is finally going for it. I am also (selfishly) thrilled to have another person to shop with, because most of the people that I care anything about up here are very busy and on a very different schedule from mine. A is my only other shopping buddy and I don't want that to be the only thing we do together, and I hate to make the b.h. go shopping unless he absolutely needs something, because although he politely waits for me wherever we go, he clearly does not enjoy himself and I don't want waste our very limited time together like that.
Also, my new shopping buddy is inclined, like me, to troll thrift shops and goodwill and the like, spending no more than five or ten dollars on a given item, but piling a cart high and trying on ten or twenty things in a go. Today was our first journey together. We went to get makeup first. Not being very good at that sort of thing myself, I felt like my advice was rather useless, so I took him to the MAC store. His idea was that he would go in and pick a few items that he liked and take them home and try them out. My idea was that we would have a professional makeup artist show him how to do it.
"That's what the people at these stores do, I argued. That's what they're here for."
He was skeptical, sure that he wouldn't be comfortable and doubtful that a person working there would be either.
When we walked in, we were greeted by a man in a very lovely flowing pair of black pants with a huge belt buckle. He had a shaved head, and had shaved off his eyebrows and painted them on with a gorgeous, movie star flourish. He asked what he could help us with. My friend (I'll have to come up with a name here eventually, but I am being so careful not to out him that I can't even think of a good fake name so am going to go with X) answered immediately that he wanted to buy some makeup.
"Are we talking like, standard men's grooming, or-"

"No," said X.

"Or Halloween-"

"No," said X again, this time a little more quickly. "More like everyday use. Trans stuff."

"Okay, great. Why don't we sit you over here..."

That was pretty much the end of it. I let the girl who was there put a face on me, and actually learned a few things. X has a great time and looked lovely when all was said and done. He bought a whole round of stuff, which cost a lung, but will likely be a near-lifetime supply, so there you go.

After that we hit an overpriced vintage store where he got a great pair of cowboy boots, and then off to g00dwill where we hit the motherload. I got a new hat and a scarf and a sweater and a long sleeved shirt for eight bucks, and we found X a handful of skirts and tops that fit and were flattering.

After I dropped X at work, I picked up the boys and went to Hubbard park for an hour and a half. We hiked and played with other dogs and wore ourselves out.