Hi Geena.
I went through something like this about 5 years ago. I didn't have a beard, but I hit a point in my life where I needed to see how passable I could be. Up to this point I had been a crossdresser who dressed at home and occasionally under-dressed. The drive to go full tilt took on a life of it's own. I was compelled to see what I could look like.
First I had to get a wig. I emailed a local shop explaining who I was and what I was after. They said I am more than welcome to drop in. I made an appointment and off I went. I must have tried on 12 to 15 different wigs. An assortment of lengths, styles and colors. It took 2 or 3 visits. On the second visit I took a woman's blouse and changed into it at the wig store in order to get a better idea of what would work. Finally selected one mid-length sandy blond wig. It's good but afterwards there was a little Bob wig that I kept thinking about. I had to have it. I went back and picked up the Bob as well. I now have two good quality wigs. The Bob is my favorite.
Second, I booked a session with a makeup artist. I wanted to see what the pros could do with me. This was a good choice. Again I emailed explaining the situation. No problem, I'm more than welcome. They had one particular makeup artist they thought would be good for what I needed. She was terrific. She took me from a boy to a girl. First visit I went into a busy beauty salon. There I sat, the only guy in the place at a makeup station right in the middle of about 20 females all in the process of getting pretty. I was in drab the first visit getting makeup put on my face. What a surreal experience, unbelievable really. I went back two more times. On the second and third visits I was fully dressed, wig and all. Never a bad comment. I felt totally welcomed in the salon. Actually had compliments on my outfits. Aww..... I remember one point where my Bob wig was getting in the way. The girl doing my makeup took a bobby pin and pinned my hair back out of the way. One of those silly little things that made me feel really girly. Always hugs going in and out. I was just one of the girls.
On the second visit to the salon, I watched as most of my male features disappeared and my feminine persona appeared. I sat there mesmerized at the girl in the mirror. The more I stared, the more I was convinced that I was passable. So much so that on the way home I veered into one of the bigger shopping malls mid-day Saturday. I had to put this to the acid test. Yikes, what a harrowing experience. I was so scared. It went well though. A few early bumps but as I went on nobody stared or looked at me. Couldn't believe I was being perceived as a typical female, nothing standing out catching odd looks. Hey I was passing. Certainly a confidence builder. There was no turning back after this. Just crossdressing at home or under-dressing wasn't going to cut it. Still do it but now I can do so much more. I always like to have options open to me.
With all of that behind me, I have a feminine look I'm quite happy with. I've taken it out in public several times. I'm confident in my look. It's pretty good. I claim my place in the world. I can slip into female mode in about an hour and a half (makeup takes time).
Now I consider myself much more as gender fluid than a CDer. I can slip from male to female and back again easily and confidently.
In terms of it changing things (lifestyle, going too far, etc.), it hasn't. The breadth of what I do has grown, but I'm still a guy who dresses like a girl occasionally. Going farther is certainly fun and I still enjoy doing it. Playing with wigs, makeup and full outfits is fun and a much richer and rewarding experience. But for me I'm really fine with gender fluid. Slip back and forth as desired. I'm really glad I explored the extremes. It's opened up some doors for me and I've had some experiences that I really cherish. Wouldn't have happened if I didn't push the envelope.
Not sure about your financial situation, but getting the pros to help really made a difference. I can't imagine trying to learn about makeup on my own or trying to buy a wig off the internet. I also met and interacted with some really nice females who were fine with who I am and what I do. They were all so sweet and supportive.
