How it began

Every crossdresser has their own story of how they started. Mine probably is similar to most.

When I was very young, I went sent off to grandmom's house frequently. Cheap child-care. When I was about 6 or 7, my sister and I started playing dress-up. Since my grandfather on that side of my family had passed away a few year earlier, there were no male clothes in the house. Not wanting to find other methods of keeping me busy, I was allowed to play along with my sister. It was cute for the first couple of times. However, when it was my other set of grandparents' turn to watch us, I still chose my grandmother's clothes. This is when I was told it wasn't cute anymore and was kept from playing that game. I continued however. I used to sneak back into their stuff when I thought I wouldn't be caught; which I did. Since I had limited time to engage in my activities, I stuck mostly to shoes.

When I finally was old enough to watch myself, I started getting bold. By this time, I had started finding items in my mom's drawer to borrow. When I was sent with my sisters to a grandparent's house, I would find excuses to be left at the house. Soon I figured that I had enough time to change in case they got home before they were due. I ventured out into clothing more. I loved the dresses. Pantyhose also held a fascination for me as well, however I never tried on those, because they could easily be ruined. I covered my tracks well enough, that I never was caught (weather they knew and never said anything, is beyond me). I remember one overnight visit, when I hid a control body briefer in my room. As soon as my grandmother went to sleep, I changed into it. I don't recall sleeping much, in fear of being caught.

Of course, all this did have a sexual effect on me. I was always turned on when I dressed. I believe it was mostly due to the raging hormones a teen aged boy goes through. When I was in high school, I convinced a girl friend at the time, it wasn't fair for her to borrow my T-shirts/sweatshirts and I get nothing in return. So I asked for old items of that she wouldn't miss, just to even out the borrowing. I received a pleated skirt which I fell in love with.

During college, there was almost zero chance of dressing. During this point in my life, I was involved in a Christian group as well, and did my best to put my dressing in my past. I did tell my girlfriend at the time, about my dressing but since I was conditioned to believe it wrong, I let her know it was behind me.

Post college, I spent one year living in my parent's basement until I paid off some debt and had enough cash saved up to get my own apartment. It was also my first time telling a girl that I wasn't dating about my dressing. Angelina (to avoid using her real name), helped me order items I was too scared to have delivered to my parent's house. We lived about 3 hours away from each other, and we met up a total of 3 times, 2 of which she got to meet Karen. We had talked about sharing an apartment together, but due to things I wish I could take back, we parted ways.

When I got my apartment, I continued to explore Karen from where Angelina left off. Mail orders were placed frequently and before I knew it, I had at least 3 outfits. I also started dating my wife, who I told after our 3 date. I wanted to get it out in the open quickly, so if there was a problem, we wouldn't be too deep into the relationship. There were many rocky places in our 6 years in regards to my dressing, but it appears that smoother waters are ahead of us.

Currently, I have probably over $4000US worth of clothes. 30+ pairs of shoes, 20+ dresses, many tops, many bottoms, and even a wig now. Enough stuff that Karen has her own closet in our new house. If we move again, it's been agreed that we need two walk-in closets.