My Transgender Cupid

Fighting the confusion of being a Transgender woman

I was at an outdoor barbecue recently when I happened to see someone looking through MyTransgenderCupid on their laptop.

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I’ve been looking to find a genuine man to date for quite some time so a specialized Trans dating site like this really caught my attention.

After many years of trying to understand myself, I’ve finally in the last year, come to terms with the fact that I am Transgender. I now clearly know that I am a Trans woman. It’s been a long road to get to this point. And I know there’s still quite a distance to go before I reach my goals of meeting a sincere man and settling down as his wife. If we could adopt a couple of children along the way that would be perfect. But, if my man didn’t want that, that’s fine too. As long as he loves me for what I am, a woman.

Evolution of Transgender women

It takes time to realize that you are Transgender

My journey is possibly not the same as many Trans women, but I think there are similarities with what others’ experience. When I think back to the time between when I was from around 12 until I was maybe 18 or 19, it was a time of almost complete confusion. If I had to summarise my pathway to my recognition that I am Transgender, it would be something like this:

  • Puberty: for most children, the onset of puberty is a tough time. Changes in the body features (Adam’s apple for boys, breast development for girls) and bodily functions (menstruation for girls) occur. Most are not prepared for this and the emotional changes can be a challenge. Girls have crushes on boys and boys start thinking more and more about sex.

For me, I certainly liked girls but was not sure if I liked them to explore having sex with or just wanted to be like them. Occasionally I saw a good-looking young man and admired him for being good-looing. I wasn’t attracted to him, or so I thought. I had more female friends than male friends and avoided much of the rough and tumble of boy’s games or fighting or anything overly physical. Most girls liked me for being softer and gentler than other boys;

  • Crossdressing: even before puberty, I had occasionally cross-dressed. I’d wear a dress or skirt and a nice top but especially liked wearing tights or stockings. By the time I was about 13 or so, I’d crossdress when even I had the chance. Once I went to a party in a full female outfit. Bra, panties, make-up and so on. The girls who I counted as a friend thought this was wonderful. They all said how I looked so feminine and couldn’t tell I was really a boy at all. I’d heard the term Transgender but didn’t really know what it meant. Another time, a year later, I went out with some girlfriends when I was fully cross-dressed and a young man starting to chat me up. He asked me to go out with him the next day on a date. I was so thrilled but also too scared to accept;
  • Gay: with another passing year my crossdressing was becoming more frequent, sometimes two or three times per week. Plus, I’d also started developing a much stronger attraction to men. Yes, I’d had sex with one or two females, just fumbling, breast touching, stroking one girl’s vagina and so on. However, I had no great urge to penetrate any one of the girls and began to think I must be gay. I tried to read up about being gay on this and even had two “dates” with men I met on the internet. As much as I liked their company, I shied away from having sex with them. I just wasn’t sure;

There are several steps in accepting that you are Transgender

  • Gender fluid: one day I came across the term “gender fluid” and though it was quite appropriate for me. Sometimes I liked to present as male and sometimes as a female. I could comfortably pass as either gender. But my sexuality still confused me. I didn’t really want to have sex with a male when I was dressed as a male. And I wasn’t sure I wanted to have penetrative sex with a female. For a while, I let things take their own course and, until I was about 17, seemed content with being gender fluid. My friends accepted me for being like this, but the word Transgender kept reoccurring;
  • Trans: it was a combination of things that made me realize that I was a T-girl. One night I watched a great video on YouTube about a male with a similar dilemma. He (she) persuaded his parents to let him consult a doctor who specialized in gender issues. Could I be brave enough and ask my parents to do the same? The next night I went to a party with some of my girlfriends. I know I looked great in a black dress I’d borrowed from one of them. My make-up was perfect and I felt wonderful.

I struck up a conversation with a young man I’d seen around a few times. I thought he was ever so handsome. And best of all he knew I was still physically a male. Well, we started dating and I think you can guess what happened eventually. Finally, I realized that I need to transition to female to make my life complete and banish all of the concerns I had about my gender and sexuality.

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