Retro Rerun: My First Advice for MtF Crossdressers

| Jan 2, 2017
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This Retro Rerun is advice for beginning crossdressers from Diane Hutchison that first appeared on TGForum back in 1998. The advice is directed at crossdressers just taking their first steps to letting themselves explore the world of feminine attire. Since Diane wrote this her gender journey has taken her to transition and marriage. Return with us now to the late 20th century for Diane’s newbie crossdresser advice that is still as relevant today.


When I first discussed with Cindy Martin [Editor’s Note: First editor of TGF] about becoming a regular columnist here at TGForum we decided it would be a good idea for me to write articles that would be helpful to beginners. Thinking about possible subjects for these articles got me reminiscing back to a time almost four years ago when I was taking my first real step towards accepting myself as a transgender person.

The first big step I made was to attend a local transgendered support group named MOTG (Momouth Ocean TransGendered). At the time I had no clue that by taking that step I would forever change my life for the better. For that matter I didn’t have a clue as to what being transgender might entail. It would in fact be safe to say that I was pretty clueless in most areas surrounding my crossdressing. The night of that first MOTG meeting I made several friends and got lots of good advice. You will even find some of that advice in this article, but looking back now I realize that there were still plenty of “secrets,” tips and pieces of information that I wish that someone had told me then. What I have put together is two short lists of those things that I would pass on to anyone taking those first very important steps.

Emotional Advice

1) There is NOTHING wrong with being a crossdresser and you should never be ashamed of being yourself. If it makes you happy and hurts no one then don’t sweat it. When I was finally able to let go of the guilt surrounding my crossdressing my quality of life increased dramatically.

2) Don’t let anyone — including yourself — tell you that you can never pass. If it is important to you and you are willing to work at it, it will happen in time. My ex-wife often told me that I could “never pass in public in a million years.” Last Christmas season I went shopping at a large local mall while crossdressed. No one looked twice.

3) We crossdressers always tend to want to move very quickly after we get that first taste of freedom with our gender expression. Because of that we have to be extra sure that we give plenty of time and space to those close to us to sort out their feelings about our crossdressing.

4) Gender is a journey and you never know where it will lead you. Don’t make promises you may have to break later. I remember ten years ago swearing that I would never want to go out in public dressed. Now-a-days I can’t get out enough.

5) If you haven’t done so already, join a support group. I feel that one of the most potentially destructive aspects of crossdressing is the secrecy and loneliness that can accompany it. You need a place where you can totally be yourself, get support and talk to others who have been there.

Practical Advice

1) You can get away with buying some parts of your wardrobe cheaply, but never skimp on the quality of your wig. Cheap wigs look bad, don’t last and will get you clocked in two seconds flat.

2) If you have large feet like I do (women’s 13w) you don’t have to pay outrageous prices for shoes. Most Payless stores in larger urban areas carry up to a size 13. I have picked up a pair of shoes there for as little as $5.00.

3) Shopping for women’s clothes can seem like a scary task, but remember that you have a right to be there just like anyone else. Whether you are crossdressed or in drab, sales people should treat you with respect and sensitivity.

4) For applying makeup it is well worth your while to invest in a lighted makeup mirror. Used ones can usually be found at thrift shops for as little as a few dollars. Make sure the mirror has a magnifying side to it.

5) Don’t waste your money on breast creams, home “permanent” hair removal systems or “amazing” natural feminizing pills. They don’t work.

If any of the above advice saves just one person a little time, money or heartache I have done my job.


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Category: Transgender Body & Soul, Transgender How To

diane1962

About the Author ()

Diane was born and raised in New Jersey. She has two fully grown sons and a husband of thirteen years. Diane runs a two small businesses and in her spare time enjoys strategy board gaming.

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  1. KoolMcKool KoolMcKool says:

    > If you haven’t done so already, join a support group. I feel that one of the most potentially destructive aspects of crossdressing is the secrecy and loneliness that can accompany it. You need a place where you can totally be yourself, get support and talk to others who have been there.

    Whoa is this ever true. Crossdressing and TG groups tend to come and go from different cities and states. Don’t be intimidated by any snobbery, tell people what you are are, and someone will be happy to welcome you.

    >Cheap wigs look bad
    >For applying makeup it is well worth your while to invest

    There are really only 1 or 2 brands of makeup that are worth a damn…hint…try the MAC counter. Poor makeup choices can be discouraging. Wigs take practice, mess it up a little, make it look alive
    by the way…MAKEUP and WIG ARE MORE IMPORTANT THAN CLOTHES

    and look out for promiscuity, there are whoremongers out there that want to take advantage of you…don’t be drunk and stupid, stay smart.

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