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I crossdressed as a kid up to about 16 years old. Never did it again until 28 years later. Now it's 4 years since I started again. Yes, there was guilt and "what the hell am I doing" for the first 3.5 years back doing it but I've found peace in myself with it now. My wife knows and although not totally supportive she's aware I can't help it and let's me get on with it in my own way.
I'll always be back & forth with this. I recently went over a year without dressing for a multitude of reasons only for it to come back stronger. I think it's learning how to deal with it that's the hard part.
I have purged so many times over the last 40 years that i would have a wonderful houseful of clothes, Ive bought and donated more girls clothes than i have ever owned as a guy. More shoes, wigs, dresses, skirts, and on and on. I should have kicked myself in the butt many times, I am luck to go 2 weeks with out buying something new.