For me, like many others, I started at the tender age of 5 years old. I remember taking a pair of my mom's panties and trying them on. From there, even at that age, I knew something was different about it with me. Over the years I had taken to "borrowing" both my moms, and younger sisters, panties (mostly panties at that time). I got caught a couple times during this stage in my life when I was around 10 years old or so. Apparently, I had taken, and held onto, too many pair of panties and it got my mom searching. When my parents sat me down to discuss the situation, I didn't have any answer for them because I didn't even know myself. The matter was dropped, and life carried on. I was more careful then by not hanging on to too much clothing anymore.
As life went on, I managed to snag a post office mail box and was finally able to start ordering my own stuff. I had just started driving at that time and could easily sneak away to check my mailbox. One day I noticed in a catalog a pair of panties that I really liked a lot and didn't want to wait to order then through a catalog. Side note, this time frame is taking place in the 90's. I saw that a store near where I lived might have it, so I drove over there to check. With the ad in my hand I, for the first time ever at that time, went into the lingerie section of a store. I searched the racks and shelves for those panties but didn't find them. I was approached by a sales associate who asked if I needed help. I sheepishly told her I was searching for something for my girlfriend. I showed her the clipping from the catalog and she helped me find it. She then asked if I wanted to get the matching bra for it too. By this time, I was still only experimenting with panties, so I had no idea what bra size I would be. I told her no, bought the panties, and left. My heart was in my chest to say the least because I didn't know what to expect.
More time passes, and I go through the dreaded binge and purge cycles of getting rid of everything, then buying it once again. I had also moved up from panties, to bras, pantyhose, stockings and garters, slips, teddies, skirts, and dresses. Not too much in the long run though as I was still living at home and my family was none the wiser of my activities. By this time, I was 24/7 wearing panties and just had a few male briefs in the event of a doctor's appointment. One fateful day I got into a motorcycle accident and was knocked unconscious for about 4 days or so. I was in the hospital for about a month from it. I have recovered from the accident since then with no serious long-term problems. One issue I had though was while I was in the hospital, my dad went to get me some clothes to wear while there and discovered my drawer full of panties. He never said anything to me but did go out and buy some male briefs to bring me instead of me wearing panties at the hospital.
When I finally moved out of the house, I felt triumphant at being able to finally clear away space in my dresser drawers for my hidden clothing. I met a woman and fell in love with her. Before we started dating, I told her about the real me because I didn't want either of us to waste time dating, only to be found out and she leave. She said she was fine with me and we started dating. After a while I proposed to her and she said yes. We were engaged for about a year and the closer we got to the wedding date, she started seeming more distant toward me. I asked her, and she stated that she thought my dressing was just a phase and that by being with her, it would go away. I told her that it was not a phase, had been with me my whole life, and would likely never change. As a result, we called off the wedding because she didn't understand the real me. That was in my mid 20's.
Now I'm in my late 30's and have been having deeper thoughts about what is causing me to dress. When I have taken online quizzes and tests in a vain effort to define myself, most all of the tests stated that they were 100% certain I was a woman. I guess my mindset tends to lead more toward the feminine as I have never fit into the stereotypical male persona. I've always been kept more to myself via reading, walks in the woods, video games, or more solitary walks of life. I started talking to a therapist but have yet to reach any definitive conclusions. Where I live right now in Mississippi, there are very limited resources. The nearest support group that I can find is over a 5-hour drive away. The therapist is an hour at least too. We'll see what I can find during this part of my life now.
I'm not even close to passing as a woman in public, so I've never tried. I'm 6'3″ tall, 260 lbs., broad shoulders, prominent Adam's Apple, big arms, huge feet, and am hairy like a Sasquatch. I have tried laser hair removal back in 2009 and it worked okay enough for my legs, but not much else. Since 2009 as well, I have had a desire to grow my own breasts. I do not want implants and will settle for whatever I can manage to grow on my own. I have tried different herbs, creams, etc. off and on and have had only minor success. I could say that I'm in the A cup range, but not much more. As stated before, I couldn't pass as a woman, nor do I want to, but there are men with breasts living happily, and I can too. I feel that I would be proud to have a pair and would find it neat to get to pick out a bra to wear each day. I have grown more confident in myself though as I went to a plus size women's store recently and bought a briefer, dress, bra, and some panties. I even tried on the briefer, and dress, while in the store and I have never done that before. I told the sales representative that they were for me, and we had a wonderful time picking out items. It was very rewarding as I've never been able to try on items at the store.
I started off my journey with panties thinking I was a crossdresser. As time went on, the term crossdresser branched out to a multitude of other categories. I'm not sure where I fit into the mix, but hopefully with the therapist involved, maybe something will show up. I do know that with, or without, the therapist helping, I am happy with who I am. I wouldn't change my past one bit (other than more confidence earlier on) and am happy that it has shaped me into the person I am today. I have had many people be happy to be around me because of my mellow, although secretive, lifestyle and I am almost certain it is because of the feminine thought patterns (not really any mannerisms) I seem to exude. Believe it or not, that is just a summary of my life thus far. Thank you to anyone who made it to the end with reading it. If it helps you in any way, for that I am thankful.