I can say I am getting braver with age. I've been in the closet for over 30 years. I was curious as a boy and did all the same things most of us did. As a young married male I would play Lingerie games with my first wife and she was OK with it. Now all these years later I still have not ventured out of my home as Alissa. However, I am part way there. I wear panties and girls t-shirts 7 days a week, I have 3 pair of women's jeans that I regularly wear to work. I think my closet is at about a 50/50 split of hers and his. I've gone to work for a week now with pretty painted red nails. I put on a bra the minute I get home and usually don't remove it till I go to work the next night. I am becoming more and more at ease with all of it. Truth is, no body cares. They really don't, too wrapped up in their own lives.
The clerk/manager of my local convenience store noticed my nails and said "I don't even want to know", I replied about what? She said "the nails." I laughed, then I said "well ya know, I am more of an average Joanne than a average Joe, but she is too much to upkeep for work every day". "Oh don't I know it, she responded. You have a great day Hun". And that was that. I really think a lot of you out there worry too much about what others think.
Please don't misunderstand, I am not saying I am ready to be totally open with everyone about who I am and who I am becoming but... most people that you pass by in day to day life... just don't care. They got their own issues.
As for me, 2018 is going to be a year for makeup for me. Time to learn, time to find who I can bring out. Looking forward to experimentation!