By the time college rolled around I was too big to raid my mother’s closet. I pretty much gave up dressing altogether for a few years. A funny thing happened after graduation and my entry into the “real world”. I started adding a few androgynous items to my wardrobe. Cutoff shorts cut just a little too high. Sandals with straps just a bit too narrow. Then came the day that I bought the inevitable dress for “my friend’s birthday”. It wasn’t long before I was regularly stopping by various department stores building up a small collection of women’s garments. The purge occurred not long after that.
I began blaming my dressing for a whole host of ills. “This is why I haven’t settled down and started a family”, “This is interfering with my relationship with God”, “This is taking away from time better spent with friends”, the list goes on. One night, I filled up a trash bag with the trappings of my “sickness” and made a deposit at the dumpster. I felt A LOT better after having rid myself of the need to dress. That lasted about three months. As time passed, I realized my supposed ills were never there to begin with. I had, and still have, a great group of friends, my reasons for not settling down were due to a strong need for independence without familial responsibilities. I still wonder about God’s judgement of my actions. I suppose this is the only real issue (other than a concern about the "reality" of my femme appearance) that I have at present.
I began to understand my reasons for dressing during this time, as well. It wasn’t borne of a feeling that I had been cheated at birth. I am very content with my physical gender. For me it was more of a desire to possess the freedom that women had to be whomever they wanted to be. Female attire, given the vast array of styles when compared to those “approved for men”, was just an outward reflection of that freedom. Gradually, I started adding back items that could be worn underneath my male clothes. Panties (occasionally), a toe ring and, later, nail polish. One day while my mother was visiting, I skipped the shoes and socks while walking outside. The reaction was to be expected, “We didn’t raise you like that!!!” My parents were two of the most loving people ever to walk the face of the earth, so it wasn’t a condemnation so much as a need to understand. I told her I just liked the look. We never saw eye to eye on that point, but it didn’t interfere with our relationship. My father had passed away before this all came about. I think he would have been more troubled by it, but not so much as to cause problems between us. My SO at the time thought my androgynous additions were just my way of being different. She didn’t have an issue with it at all. Granted, I never tried fully dressing around her either.
Fast forward to the present where my friends and work colleagues are not surprised to see me wearing a kilt or sarong and nail polish during the off-hours. My SO gets a kick out of seeing the reaction of the general public. I’m not trying to draw attention. I just want to be free to dress however I darn well please. Ha! Ha!
A few weeks ago, my SO was looking for a towel in my laundry room when she came across a pair of panties. The initial reaction was to be expected, “Who is she?” When I explained that my dressing was not limited to kilts, she laughed and said, “You are the only man who could get away with that excuse.” We had a vacation to New York planned and I confessed my desire to go fully dressed one night while we were there. She thought it was an excellent idea and even helped me pick out the proper makeup. There we were, strolling through the Times Square subway station on our way to “Lips” down in the village. It was one of the best nights of my life. It gave me the courage to start stepping out in town (parks and bike rides). Last night I showed some of the pictures from the vacation to one of my co-workers. She thought it was great, but she said that I needed to consult her on the choice in clothes next time. Now, I’m just wrestling with making sure that my new found freedom doesn’t turn into something that takes time away from the things that are really important. I think I’ve got a handle on that. Having found this wonderful new group of girlfriends online, I keep asking myself, “Can things get any better?”
Lots ‘o love, ladies!
Angie
I did laugh out loud about what your wife said when she found the panties. 
I think you really have it together because of the way you're dealing with this side of your life. You've allowed some form of gender expression throughout your life and your thoughts for checks and balances is very important and really cool. It should be a nice little guide for others on the way they should be with their second self.