Getting a Skirt and Cuddling my Boy Soon

I came out to my family as a femboy about a month ago, and they've been super supportive. My mom got me some thigh highs with more on the way, and while they did deny me anything more until I work out for a month straight so I'm capable of defending myself in case of creeps, they're still supportive of me wearing what I want to.

Recently, I proposed the idea that maybe I could get certain feminine clothes based on how much I work out for wearing around the house to get used to them and all, with a skirt or some dolphin shorts being the first thing I get. And at around the same time I'll be getting these, my boyfriend will be back from his cruise trip so we can cuddle :3

Please put what you think I should get first, and things to do with my boyfriend, if you can think of any.