I have only been dressing for 15 months (for more than 5 minutes at a time) so maybe I’m not ‘qualified’ to answer this question, but these are my thoughts anyway. Cross dressing is a journey and it is you who decides the final destination, whether that be trans or enjoying a quickie dress for some gratification or somewhere in the middle.
When I first started dressing, I put on a bra and panties and a skirt and walked about the house for about an hour and then got changed back intro drab. It felt good, but naughty and I was wondering if it was ‘wrong’ to be having these feelings. After a couple of weeks of doing almost the same, but for slightly longer each time, I joined CDH to be part of an accepting community and somewhere I could ask for help in understanding these new, yet slightly strange feelings I was having.
My home life is such that I am very closeted, and I don’t see a way of changing that anytime soon. SO is a certain way and revealing my dressing to her could go in any of several ways and I don’t like not being able to control that and hence I’m unlikely to put myself in that position.
Now, I’m not saying never to full transition, but I am saying not at this point in my life and that’s totally OK. I’ve reached my destination for now which, for me, is underdressing most days and dressing several times a week at home when time permits. I’m happy with that. I don’t drive so going out in my local area could be somewhat challenging but maybe some day.
The point to all my ramblings is that if you be more girly as time goes on, then that’s fine. You’ll also find some days, the urge is stronger than others. Have you considered a wig rather than growing your own hair out as this might give you more flexibility in your look?
As I said, you (and lots of the girls on here) are far far more experienced than I am here, but I wanted to give you my thoughts on the off chance something was helpful *giggles*