My journey began innocently enough. My dad worked two jobs at times and my mom was a stay-at-home mom until she wasn't. I remember her applying her various make-up products while she was in her sexy bra and silky panties. I was entranced by her transformation. She would start by applying moisturizer and foundation and I loved how the eye shadow, liner and mascara made her eyes pop. She would then add a creme blush and finish with a setting powder. She looked like she could have been in a Playboy magazine. There was just something magical about how she changed from a small-town mom into an exotic-looking woman.

I can remember thinking I wanted to be a girl and even said something to my mom about this. (I should mention that she thought I was going to be a girl before I was born. She even had a girl's name picked out. I always thought she was a bit disappointed I wasn't a girl). Her reply was the doctors would do bad things to me to stop me from thinking this way. She explained they might do electroshock therapy or other draconian treatments, so it'd be best to forget about such ideas. I can also remember a television movie where a grandmother was raising her granddaughter and a caretaker/gardener figured out the girl was really a boy. If I recall correctly, the girl became the boy she had been born, but the movie left me desiring to be the girl. Once while visiting my maternal grandmother, I went into her bathroom and dusted myself with some of her scented powder. Of course, my mom and grandmother noticed and made me feel embarrassed. I was so embarrassed I covered up with a dirty rag rug to hide the smell.

While I was still fairly young, my dad was forced to stop working due to major back surgeries, which meant my mom needed to find a job. Mom was one of the first women in our community to work outside of the home, and there was a little ostracizing from the neighbors.

She became a beauty consultant, which meant she went door to door selling make-up to our neighbors. I went with her on one of her visits and was intrigued by the process of selecting complimenting colors and the sales process. The income she generated was insufficient to pay the bills and she finally got a job at a factory that made electrical motors. She made sure she still applied her make-up every day and still wore clothes that made her look nice. Even after dad recuperated from his five major back surgeries and became employed again, mom continued to work, eventually retiring. Working in a factory and being around people who tended to be a bit crude had an effect on her, but I digress.

It was when my dad went back to work, albeit in a new field of employment and mom continued to work that I turned sixteen.

I wasn't a big boy and certainly wasn't muscular. In fact, many people thought I looked feminine. I was conflicted about this, and although their comments were intended to be cruel, they made me question my sexual identity. I didn't have the confidence to have girlfriends and looking at my older brother's Playboy magazines, I related to the women. I longed to be pretty with the make-up and sexy clothes. I fantasized about being a girl with beasts and no penis. It was at this time I first applied make-up and tried on my mom's panties and bras. I can remember putting on her corset and nylons and her dresses. I even wore her high heels. She had a permanent applied that had burnt her hair and she'd bought a wig.

Back then a woman went to the store that sold wigs. So, once I was made up, dressed in her clothes and put on her wig, I looked very much like a young woman. I would get very sexually aroused and masturbate. I wanted to explore what it would feel like if I got a blowjob, so while I was made up, I laid down on the bathroom floor and raised my legs over my head. Once I had my legs pulled up as far as I could, I was able to lick my penis and put it in my mouth. I would cum in my mouth but I would never swallow, although I obviously tasted it. There was something so very sexy about seeing my red lipstick on my penis.

I wanted to feel more like a woman, so I started experimenting with putting items in my butt. I would give myself enemas and use tampons. The tampons proved to be a challenge to pull out once they absorbed the liquid, and I stopped using them after developing hemorrhoids and my dad telling me to not put anything down the toilet that could plug up the septic system.

I continued to cross-dress until I was about eighteen. I eventually got back into it occasionally after I got married. I would usually just apply some lipstick and masturbate but occasionally, I would apply other make-up. My wife and I were together for almost thirty-eight years. It was after our son committed suicide at nineteen, that I told her about the crossdressing. We went to counseling and I realized she was totally against it and tried to put that part of me back in the closet.

It was a few years later that I brought it up again. We again went to counseling and she decided she couldn't love me as a crossdresser and I couldn't be happy unless I was a crossdresser. We ended up getting a divorce and I moved to a small community where crossdressing was not acceptable.

During the separation and divorce, I had tried to explore my feminity, creating a female persona and engaging with other trans people. I realized the LGBTQIA community was not very welcoming. It seemed even the trans people were critical of others if a person didn't take hormones and/or have surgeries. I wasn't into cliques and did away with the female persona, realizing I'm just a man who likes to be feminine and enjoys a vibrating dildo.

I now have a girlfriend who will tolerate my crossdressing but doesn't really want to be part of it. We have made love dressed up but it isn't a turn-on for her. She has used the dildo on me but then makes little digs about it.

This story is one person's journey of how life can guide a person. Personally, I wish I had not been a crossdresser but I know we don't always get what we wish for. The only thing a person can do is try to be happy every day and enjoy the time he or she has on this planet while helping some others along the way.