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Beginner's Guide to MTF Crossdressing

How to Meet Women and Influence People.....While Crossdressed!

By Diane Hutchinson


Most crossdressers, myself included, often wonder if the quest that many of us are on -- to find a woman fully accepting of our crossdressing -- is nothing more than a pipe dream. Friends, I am hear to tell you that I have found that elusive grail and better yet, I am willing to tell you how you can too. Gather around and settle in while I unlock my secrets of "How to Meet Women and Influence People....While Crossdressed!"(copyright DBH 199...of course).

People, especially those outside of the transgendered community, are amazed to find out what I was wearing that when I first met my S.O. Mary. At the time I was dressed in a rather tasteful black skirt, an attractive blue knit v-neck top, black nylons and a fashionable pair of black shoes. Well lets face it, I looked pretty darn good and well dressed for a woman in her thirties. In fact I had already been hit on by men twice that night before Mary and I crossed paths. Now don't let me mislead you, most everyone there knew I was a crossdresser before I even stepped foot into the place. The purpose of the gathering I was attending was a monthly get together of the America On Line South Jersey chat room people. All of my on-line acquaintances knew me by AOL screen name Diane1962 and from my user profile or from having talked with me knew I was a crossdresser from day one. Even though I was at a "regular" restaurant/bar most everyone there accepted me and several of the women even considered me a friend. In time I would become just another one of the girls (Who among us hasn't dreamed about that?).

That evening when Mary approached me to strike up a conversation I have to confess that I was pretty attracted to her right off the bat. She was a cute little thing and quite stylish herself. My first inclination was to go into a sort of macho mode and make light of my crossdressing as a sort of whimsical aspect of my personality. To my credit and own amazement I proceeded to maintain my natural personality which is substantially more feminine than my male persona. As a result we had a really nice long chat which was the start of our friendship and eventual pairing. Let me finish up this story with Mary's thoughts on our first meeting.

"If anything stood out to me it was his courage and how hard it had to be for him. I have to admit that I was curious too in wondering what "she" might be packing underneath that skirt. We spoke that night for a long time about all sorts of stuff like our kids, work, people we know and where he got that cute little skirt. After that night we became friends and spoke all the time. (NOTE - Modesty almost made me leave this next part out, but who I am kidding?) Several months later I met him in his male form and I wasn't disappointed, he was just as adorable. If someone was to ask me if I fell in love with Diane before or after I met her male side I wouldn't know how to answer because they are one in the same to me."

Boy, I love that woman. "Okay, Diane enough with the history, where are those secrets you promised us?" Fair enough. Here is what I took away from that experience and it has served me well. All of these "secrets" require a good deal of confidence and openness to pull off, so they are definitely not for everyone.

  1. Be honest and true to yourself. If I hadn't been honest enough with myself I never would have had the nerve to be out in that environment in the first place. I knew that my crossdressing was an important part of my personality that was not going away. Denying my feelings to myself could only lead to pain and heartache.
  2. Be honest with people about yourself if you have any intentions of having a intimate relationship with them. Had I not done that any of my relationships would have had to have started with an unhealthy dose of deception. Ultimately keeping my big secret would likely have come back to bite.
  3. Be proud of the uniqueness you process in being transgendered. Our very nature gives us each a special understanding of the genders that most men or women do not experience. Believe it or not, some women (even some men) can appreciate and respect that uniqueness.

No great revelations in those "secrets", just mostly common sense....right? I guess the trick lies in the execution of them. Hey, I never claimed it was going to be easy. If you are going to pursue such an elusive goal you have to expect some difficult obstacles. I can tell you from my experiences that in the end it is all worth it. The level of openness, honesty and closeness I have in my relationship with Mary far surpasses that of any other relationship I have ever had in my life. Nothing could be better.

My friends, I have now imparted enough of my questionable wisdom needed for you to start your quest for that special woman. Remember there are no guarantees out there, but if you take the chance there can be countless possibilities.

P.S.: I know I am one lucky SOB and that lightning like this might not strike me again in a million years. This article is totally true however and names were not changed because neither of the parties involved were in the least bit innocent ;) .

Diane


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