Check out steps 15-13 here.
Check out steps 12-10 here.
Check out steps 9-7 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.
6. Dress Up on Halloween
Most crossdressers would love to actually go out but not all of us actually do. One of the biggest reasons is fear of ridicule or physical harm. Well, what is the one time during the entire year that you can dress however you like and be completely free? Yes, ladies and gentlemen, October 31st.
Don’t be afraid to use Halloween as an excuse to gauge people’s response to you in drag. You can be serious or ridiculous in your choice of costume, but just remember to have fun. I have seen so many men in drag on Halloween and most of them were probably not crossdressers. However, I have never done this myself, which will probably change this year.

Your choices are practically limitless and you will almost certainly not shock your friends and family. Have any of you done this for Halloween? If so, what was your costume?
5. Take on a Femme Name (if you like)
Many crossdressers decide to adopt a female name to represent this side of them, yours truly included. When I first began researching crossdressing on the internet, I found that everyone had done this. As I had never before communicated with people like me, I not only wanted to fit in but I was thrilled to be able to relate to others. I chose the name Jessica almost immediately after this. I’ve had ups and downs with having a female name, but that is certainly a topic for another discussion.

Keep in mind that this is not a requirement to be a great crossdresser. In other words, you don’t have to have femme name to feel and be feminine, the choice is up to you. If you wish, you can certainly doll yourself up and call yourself Abraham or even Scrappy Coco. The point is, do what you feel is best for you.
I have to admit that even though I had taken on the name Jessica over ten years ago, I still felt quite awkward my first times introducing myself as her.
4. Buy and Practice Makeup
This is one of the most important steps toward mastering crossdressing. Eyeshadow, foundation, concealer and lip color are the objects of obsession for many of us. We actually have more to do than most genetic girls as we have to shave and work some magic to cover up that facial hair stubble. I’ve been very blessed in that my wife has done my makeup several times and is always willing to teach me, she is very patient.

If you are not so lucky as to have another person to help you with makeup skills, there are plenty of other options. There are books about makeup, youtube video tutorials and plenty of e-journals. You can also ask for tips and advice at crossdressing forums and message boards.
If you are comfortable enough to do so in public, visit a make up counter at a department store, Mac, Sephora or Ulta and ask for a makeover. They will provide you with all the things you need and of course you get to choose what you want to purchase. There’s no doubt that makeup is a vital piece of the puzzle when dressing.
Coming soon to Jessica Who? you will be able to share in my makeup tips and secrets.
Click here for the Top 3 Steps to Better Crossdressing !

{ 2 comments… read them below or add one }
Practice, practice, practice. Read what you can, watch videos too, but keep on trying. It's the only way to learn. Sure, you'll make a mess of it (I know I did!
) but with time you'll get better at it.
Yes, I definitely am up for practicing, it makes perfect