This page is intended for those who have thought about crossdressing and maybe even dabbled in it a bit and now are thinking about taking it farther. It can be very intimidating once you decide to explore crossdressing especially if you are not comfortable asking for help. Most mature crossdressers evolved over time experimenting with bits and pieces of clothing acquired one way or the other and most likely purged at some point. I hope this page can help you figure out whet you want and start you on your feminine journey.
WHERE TO START?
You probably see women out and about and say “Wow I would love to look and dress like her” possibly walking into a wall in the process. Been there done that! But can you pull that off or is there a better look for you that would be a better fit for you. To find this out there is some work to be done. Before the journey starts you need to figure out where exactly you want to go. Assuming your goal is to make the best possible female presentation possible given the male body that you have, you need to evaluate what you have to work with. Many guys dream of passing and it is a good goal but not achievable for most. We will head that direction and can change course later. Wigs, heels, dresses, breast prosthesis, hip pads, makeup and jewelry are easy to buy, much more so than years ago. Once you know what you need you just order it but not before the evaluation is done.
The evaluation priority is from the top down in my opinion and passing is not even on the horizon at this point.
The biggest problem men have to deal with is the face which is what people spend the most time looking at. Just coating it with makeup does not accomplish anything unless it is done properly. When you hear people talk about makeup foundation it is really a misleading term because it is not really the foundation. The true foundation is the skin on your face which is where the evaluation starts. If your skin is smooth like a baby or fashion model you are very lucky and a rare find. Most likely you have large pores and dead skin cells on your face which will become much more visible after applying makeup on it. The smaller your pores and smoother your skin the better your makeup is going to look so goal number one is to fix the skin.
I recommend a micro dermabrasion facial from a salon which in guy terms is sandblasting your face. The salon is going to do great stuff to your face cleaning pimples and blackheads off then sandblasting. Yes sandblasting your skin to remove the dead skin then moisturizing it making it as smooth as possible. Maintain the skin progress that you make by daily moisturizing right after your shower in the morning. You will need to do it more than once to achieve smaller pores but when you do can stop if you like. I like to do it the day before I go out dressed because my makeup looks much better. I do it a couple of times per year and it costs between $80.00 and $125.00 depending on where you live. Once your skin is the smoothest it can be and pores very small you have solved a big part of the challenge.
The lighter your beard the easier it is to cover with gray or white hair you can pretty much just shave close and your done. The darker the hair the harder it is to cover requiring heavier base makeup to cover. Max Factor has a tube foundation that comes in stick which I used many years ago and works well. You can smooth it on and then thin it out to make a more natural look if the beard does not show through. The ultimate is to remove your beard with laser or electrolysis treatments. Electrolysis is the only one they say is permanent but takes a long time to accomplish. Laser is much faster and lasts a long time and in some cases permanent. I have done both laser first then electrolysis the went back to laser.
The body you have also dictates what kind of female shape you can get because you need to add padding for hips and breasts. Doing this right saves not only lots of money but time also. Ideally once you make this decision it will last forever and you will buy all future women’s clothing based on the correct size. Silicone Breast forms range from about $80.00 to $500.00 depending on the brand and silicone hip pads about $300.00. To do it right your looking at $400.00 to $800.00 to create your female shape so it is a big investment. It can be done cheaper with foam rubber but they feel nowhere near as good as silicone and will tear at some point and need to be replaced. Your silicone forms will outlive you and be your foundation for life. You will need to measure yourself then calculate what female size is correct for you. Beer belly’s are a problem and will take you to the shape wear, corset, or waist cincher route.
I don’t know anyone who starts out wanting to dress like their grandmother but I suppose its possible. Your age plus or minus a decade is a good rule of thumb unless you are a fetish dresser in which case their are no rules. You most likely won’t pass but will get lots of attention. My style is conservative as you can see from my pictures because although I want to be noticed I also want to make a good impression. Dressing conservatively does not offend women or attract men which is perfect for me. I would like women to appreciate my sense of style along with the time and effort I put into being me. They don’t have to say anything or approach me and any way just appreciate. I make no effort to pass or blend in using my male voice to communicate so there is no mystery who I am. While I dress conservatively I am also guilty of overdressing for most outings especially in 3 to 4 inch heels. If I had to wear jeans and tennis shoes I would stay home or go as a guy.
Choosing a wig is right up there with the face in importance because its one of the first things people are going to notice about you. A woman’s haircut sends a sign of how they think or their personality. I won’t get into psychology but if you think about the hair on the women you know it should be instructional. For many years I wore shoulder length styles but discovered shorter wigs could work for me if the style was right. Most women over 50 have gone the shorter route because it is a lot less work. The color makes a huge difference because your skin tone plays a huge role in what color will look best on you. Pretty much the older you are the lighter the color should be not necessarily gray maybe but blond with gray streaks. I would advise buying a cheap wig in the color you are thinking of and then going to a wig salon for a consultation fully dressed as a woman. This way when the stylist puts different color wigs on you the differences will be obvious. Some will make you look great while others not and all based on your makeup which in turn is based on your skin tone.
This is where the benefits of your previously discussed smooth skin really pay off. The makeup foundation product matched to your smooth skin (true foundation) gives you a great base to start the pretty process. Once the proper foundation color is established matching face powder is next as they are used together. The colors you will use for blush and contouring will come from a palette compatible with your foundation. Eye shadows follow also based on the foundation shade and guess what? All of them are related to the hair color of your wig. If you take an attractive red haired fair skinned woman with her makeup perfectly matched and put a shiny jet black wig on her it changes her makeup. The same would be true if the woman had natural jet black hair and she used fair skinned red head makeup. Makeup is a crucial step because men need it to have any hope of passing, blending in, or just looking as much like a woman as possible. I am a big fan of contouring also to change the face shape making it look more feminine.
Here again it is best to get help from a makeup artist and there are two ways to do it. One is to make an appointment with one of the stores in the Mall like Sephora or MAC (My favorite) and have them show you. Just call them first and let them know that you are a crossdresser and possibly schedule your appointment in the evening when the store is less crowded. That is a gutsy approach I never would have done it years ago but have done it now. The other approach is to go to a TG Makeover store where they specialize in Transgender / Crossdresser products. Most do makeup on you for a fee and most likely have the products that you will need. Some will also have a limited supply of wigs so possibly you could accomplish wig & makeup at the same time.
I hope that you now have some basic idea of what you need to start your journey. The Crossdressing 101 page is a good place to start exploring for more detailed information. You will find detailed instructions on other pages telling you how to accomplish items 1 through 6 above. I recommend starting with the HOME page then explore all the pages to see how it all links together.