Don’t Do This When Crossdressing

So, you have longed to dress as a woman and are a beginning cross dresser, but you don’t know where to start? Well, you’ve come to the right place as we talk about why you don’t do this when crossdressing.

We’ve all been in a similar situation and making the right decisions when it comes to every aspect of cross dressing is never easy. Finding your “desired self image” with the right makeup, clothes, hair style and so on can be nerve wracking to say the least. Even when the commitment to dress as a woman is so overwhelming, total frustration can cause you to shout “I give up” time-and-time again.

Don’t give up, even if you must take baby steps to reach your goal. The end result is always satisfying and worthwhile.

The following is a list of my recommendations of what “Not To Do” as you strive to fulfill your dream.

Don’t…wear your unsuspecting wife’s clothes, undergarments, makeup, wig or accessories. By doing so, you will inevitably leave tell-tale makeup or perspiration stains, among other things, on her clothing, or worse yet, tear a hem or damage a top or dress. If your spouse is OK with your cross dressing, ask her first. Your spouse will probably prefer you to buy your own clothes, so she can borrow from you.

don't wear wife's clothing

Don’t…be afraid to go out to the mall or department store in male mode and shop “for your wife” when putting together your wardrobe. Internet sales are great, but when shopping in person you can see and feel what you are purchasing and it’s a lot more fun. You may also find sales associates who are willing to help, even when you are buying lingerie.

Don't be afraid to shop for womens clothing in male mode

Don’t…shy away of sitting in a mall or department store and watching women. Get yourself a cup of coffee or a soft drink and analyze how they walk (especially in heels), move their hips and hands, tilt their head when taking, their clothing style and so on. You will learn so much in no more than an hour. Then go home and practice.

Don't be afraid to sit in mall watching women

Don’t…buy a cheap wig or anything cheap for that matter. Your wig should look real. At times, you can get lucky with a cheap wig or inexpensive clothing, but aim higher and look for moderately priced items which are of better quality.

don't buy a cheap wig

Don’t…wear too much makeup. Beard cover, foundation, eyeliner, eye shadow, mascara, blush and lipstick are perfect. And, don’t over indulge. You want to look like a woman, not a drag queen. A department store cosmetologist can be a big help as many are willing to assist in teaching you the proper way to apply makeup. Remember, our money is worth the same as any genetic female, and a CD often spends more on product.

Don't wear too much makeup

Don’t…wear false eye lashes until you are comfortable applying them to your eyes. Remember, practice makes perfect.

don't wear false eyelashes unless you are comfortable with them

Don’t…be too buxom up top or too wide in the hips. You want to be proportionate to your height and weight. Always err with smaller sizes. If you want to have 38D breasts, try 36C instead. Don’t worry about buying a corset or contoured hip pads. Buy a body shaper and create your own hip pads out of sponge rubber until you are sure and have the money to purchase professional formed corset or padding.  It takes some time to be comfortable and confident when wearing a corset, while a body shaper will pull you in at the right places and give you a slimming figure.

don't be too buxom up top or too wide in the hips

Don’t…wear outlandish clothes and colors. Dress appropriately, not necessarily for your age, but for your surroundings. You want to blend in when out and about, so dress conservatively. Think “office” styles when buying any ensemble. Skirts, sweaters, blouses, above the knee length dresses, and low heels and flats are a perfect start.

 don't wear outlandish clothes

Don’t…wear gaudy or over-the-top jewelry, ear rings and finger rings. Jewelry is important, but make sure every item is complementary to your outfit and shoes.

don't wear too much or too gaudy jewelry

Don’t… buy 4-inch heels until you learn how to walk in 2-inch heels. Walking in platform or ultra high heels is not as easy as it looks. Practice, practice and practice.

don't wear heels that you can't walk in

Don’t…let your first time out be a downer, one where you will go home and say “never again.” Of course you will be nervous, so carefully plan, execute and enjoy. You don’t need to go overboard. The first time out should be simple and brief. Take baby steps. Even going for a drive in your car is better than nothing. If you are really brave, go to a mall, a department store, a movie, some place there are people. You have worked so hard to get ready and look as good as you can, so take advantage of the moment. Try to blend in. Remember, nobody is consciously looking for a “man in a dress.”

Don't be afraid to blend in

If you can handle all the don’t do this, you’ll have no problem with the Do’s!!!

You might also want to read Nora and Eva’s observations on dress at the most recent Keystone Conference in Harrisburg PA

4 thoughts on “Don’t Do This When Crossdressing

  1. The first time i went looking at Make up I was spotted by one the girls at the store she was col with it and was great help. Later i when Bra shopping and got fitted by 2 shops on the mall one Fredrick’s (before they closed the mall shops.) they To Victoria’s Secret. Both shop i went in and asked if they bra fittings for Trans and they said yes. I was dressed in jeans and T-shirt and yes a bra and Panties.
    I had a bra that fitted ok but it was a handy me down from a friend underwire not padding . It let get good size range on me Both shops the girls were respectable and happy to help. Then we went to Macy’s and my friend said let check out the Clinique makeup both there . the girl did my make up for me and i looked great. she was again happy to help had question on my Transitioning from male to female and what I was feeling and all she was just dear and so helpful. My friend she was shocked how much I was passable after and I walked about the mall for bit more looking shops and got nothing but Smiles from everyone. I felt great It was one of those days that you remember being your self in public and all went great. I have not tried again just no time and my friend is working or she take me out again. I really want to to VS and try on bras and get one that can afford They felt so good. I know this isn’t going to happen every time but it was good I get seen as woman a lot long hair many thing but I think it is in my face too. even with out a bra you can see my boobs (42 B) through my shirts.

  2. Thank you so much!! I had a rough day but when I finished reading your page I smiled. I’m 53 and have learned most of these lessons..I still haven’t been out as June but I’m going to this weekend. I’ll go to the mall then catch a movie in the same mall. A warm hug from Alaska

  3. Thank You Carollyn, for providing this valuable information about the art of successful crossdressing, and in turn giving the beginner a satisfying experience.

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