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15 Steps To Better Crossdressing – Part Five

by Jessica De Leon on June 12, 2009

[UPDATE - Download the e-book, 15 Steps To Better Crossdressing here]

Check out steps 15-13 here.
Check out steps 12-10 here.
Check out steps 9-7 here.
Check out steps 6-4 here.

When it comes to crossdressing, most are constantly looking to improve. Sure, there are masters in our midst, but the rest of us always want that latest tip or just general advice. I have compiled a list of fifteen steps to becoming the best crossdresser that you can be.

Before we get to our Top 3 Steps to Better Crossdressing, let’s recap the first twelve

  • 15. Dress Up & Go Out
  • 14. Read Fashion Magazines
  • 13. Accessorize!
  • 12. Try On Clothes (In Store)
  • 11. Attend a Conference
  • 10. Improve Your Physical & Mental Health
  • 9. Tell Someone
  • 8. Read a Book on Crossdressing
  • 7. Take Your Femme Persona Online
  • 6. Dress Up on Halloween
  • 5. Take on a Femme Name (if you like)
  • 4. Buy & Practice Makeup

Jessica Who? now proudly presents our top three steps to better crossdressing.

3. Find Your Body Type

If you’re truly serious about dressing to look your best, you should probably try to figure out your body type and dress appropriately. Many of us have big shoulders, big arms, and no hips, but do not panic. There are women with these same qualities and there are clothes out there that can downplay some of these features.

Here are a couple of links to help you determine your own body type.

This is not set in stone, though. I’m definitely an advocate of wearing what you want where you want, but these are just some general guidelines that will make you look better in your clothes.

2. Shopping

Yes, that’s right: Shopping! Most of you (if not all) undoubtedly have a handle on this. We must shop to build a wardrobe, and whether this is online or in store, try your best to have fun with it. For some, it is even more enjoyable than the actual application of makeup and dressing.
Online shopping is fun because it allows you to browse quickly and anonymously, but of course in store shopping is just the best. If you have shopping buddies, it can be an even greater experience. In addition to clothing, there are wigs, shoes, accessories and padding to shop for.

I’ve never shopped in drag but I have a friend who has, and she tells me that it is a wonderful time. I’ll definitely have to try that one day.

1. Accept Yourself

Accepting yourself for who you are is the most important step in becoming a better crossdresser. I know that it’s a bold claim, but one that I feel very strongly about. My wife and I briefly debated this one, but I ultimately convinced her that this should be the top choice.

You can have the trendiest clothing, the most beautiful wig, the best makeup collection and skills but without acceptance you will actually have little. Remember that being a crossdresser is not wrong, it is a beautiful gift (thanks, Gabi!) that should be expressed and not bottled up like some sort of pestilence.

Now, this is certainly no easy feat, and I will not pretend that it is. As you all have read, I have had my own set of struggles that are not much different from your own. It will be a gradual process, one that can be expedited by a support group, loving family, an encouraging significant other, and by following some of these steps that I have presented to you.

Unfortunately, there is no magic fix for this one. Nothing that you can buy or read will do more than for you than you can do on your own. Our society has shoved gender stereotypes down our throat for all of our lives and it can be quite difficult to undo them. I am working toward acceptance just like many of you all out there, and if you ever need support you know how to reach me. As I always tell my friends and family, “you’ve gotta do what makes you happy.”

Thanks so much for reading through my 15 steps to better crossdressing. I hope that you enjoyed them and that they can help you in your journey as a crossdresser. Stay tuned for a surprise on Monday!

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{ 9 comments… read them below or add one }

1 Savanna Lisa Lynn June 12, 2009 at 2:45 pm

#1 is so hard. I've come to realize that I dont even accept myself in drab let alone dressed up. It's tough working through that.

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2 Lynn Jones June 12, 2009 at 4:05 pm

I think self-acceptance is the hardest step. Coming out, dancing in heels, a doddle compared to this :)

All I can say is that it takes time and while you can't buy it, good friends (and partners!) and support can help you on your way.

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3 Jessica De Leon June 22, 2009 at 9:22 pm

You both are so right, I still have some trouble with it. I'm hoping for a day where I will be 100% okay with my feminine side no matter what. I realize that this is only part of my being, as the rest of the time I am completely happy with being a man.

I guess what many of us are searching for is that perfect inner balance.

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4 derek July 4, 2009 at 10:52 am

I’m a crossdresser for the last 7 years and I love wearing girls stuff better. I just wanna be able to tell my firend but, I don’t know how?

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5 Joyously October 12, 2009 at 3:10 pm

I’m unable to tell a friend that I’m in panties ,bra and nightgown
every night. What I would like is to have a CD as a friend. She could
help me with my make up,girl gossip. If we knew a couple of others
we could have PJ parties. Being a senior citizen it’s all a dream.

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6 Julie M Shaw October 14, 2009 at 7:57 pm

Thanks for these posts – informative and encouraging, too. You are a true sweetie for all you do for us, Jessica.

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7 bret April 7, 2010 at 8:02 pm

I love crossdressing been doing it for five years and plan to do it for a very long time.

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8 Stephen April 11, 2010 at 6:45 pm

I have been crossdressing for seven year now. Every time I dress up I feel so sexy. I wish I could feel this way all the time. When I get my own place I plan on crossdressing so much more. Crossdressing is so hot. I just wish I were a hot girl in the world. Maybe someday someone will support me and expect me as a person that crossdressers !

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9 Josie Blume May 6, 2010 at 10:03 am

I an a T-girl, a woman. Been one all my life and I knew it. I luv’d your series on ’15 Steps’. Thanks for sharing. I think it should be recommended reading for crossdressers and T-girls. I luv when I get the chance to dress and be myself, its just natural. I can feel sexy and feminine all the time but when I dress it does heighten the pleasure and confidence of being a woman.

Keep writing, I’ll be and am a frequent visitor. Enjoy life, well guess you already do.

One of my favorite quotes is: “I have committed no crime. My only “sin” was to be born in the wrong body.” ~ Caroline Cossey

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