Sorry for long post. I very rarely post here. When I do its generally huge novel so sorry about the size of post.
Since I originally made my introduction post things have changed a lot for me and my views of cross dressing. I have only been dressing up for about a year now. I foolishly tried (and failed) to ignore this part of myself for many years and did not act on it. The only person that knows I do this is my fiance who embraces it and has helped bring it about to where it is. We go shopping at least once a week and she buys me more clothes/make up/shoes as gifts than I buy myself. We are both very liberal and come from an art background. Nothing like watching a movie and doing your nails with your significant other.
This all started from an awesome pair of 3 and a half inch ankle boots she got for me last week that I really really like.
The problems comes from I've always prided myself in being very eccentric and went against the social norms. It has always been important to me to do my "own thing" and have nothing but admiration for those who do the same. At the same time I recently feel like I am a liar. Cross dressing for whatever reason is clearly big part of who I am, and I am hiding it now just as I did before putting on my first skirt/top. Hiding it out of fear, and fear alone.
I am different than most of the posters here (I think? No offense if I am wrong). I am simply a man who likes pretty clothes, make up, shoes, etc etc. When I am home I am cross dressed basically the entire time. When I get home I change, and I sleep in female clothing. I don't want to pass as a female, I have no interest in changing my voice, and I like the masculine things about me. I keep that masculine side about me when I am dressed as much as I do when I am not dressed. I simply am just me regardless of what I am wearing.
So back to these boots she got for me. I like them so much it almost seems like a waste that I am never going to be able to wear these out and about. I ask myself if I pride myself with being such an individual willing to go against the grain should I not be wearing these boots when I want (assuming it's safe)? To not wear them would be out of pure fear of rejection from a part of society I don't care for to begin with. It makes me feel like a fraud to my values. Easy values to have and preach yet so hard to practice I have found.
Also I am 6'6 and come in at 250 pounds. With these boots I would be about 6'9 and god would I ever stand out. Yet, I am starting to think that perhaps I shouldn't be ashamed of this cross dressing and just do it. I know I can't do it where I currently live (we are moving from here soon as we get our second degrees). We live in perhaps the most conservative area of America. It would be dangerous to go out dressed in even minor things.
I am curious about couple of things. Is there anyone here that has experience dressing in female clothes yet not at all trying to pass as a woman that might actually stand out as much as I do? If I decide to go through with it and say just wear the boots I love so much, maybe simple top, and simple jeans (no make up) how much hassle can I expect to get from it? Remember... I would be standing 6'9 in these heels and already catch attention as it is. I've considered a pair of flats and nothing else female to start off with so I don't stand out as much.
I simply don't know what to expect from this. I am afraid to do it. As I said I feel like a fraud for not following my own beliefs. It is almost like I MUST to do it simply for the fact to not do so would not be sticking to my own personal value system. Yet, I don't want to end up as some kind of youtube video and be the object of a lot ridicule.
So does anyone have any advice or experience with such things? I would appreciate it and insight from those of you who have been into this longer than I have. Like I have said I only been acting on this for a year. Being so large, and knowing I am going to stand out so much just makes it worse. I already can't blend into a crowd as it is lol.
I am feeling like a fraud/liar to myself and beliefs by not doing it.