I was in the same boat not that long ago. Sandi's City Styles is right off of route 9 between Worcester and Shrewsbury. They don't go out of their way to say they are trans friendly but they have been very nice and accepting of me. They've even helped me with some of the basics I didn't get growing up. I will say that it looks like there clientele is a little in the older side, but I'm almost 40 myself and not looking for a fashion model hair style.