Thank you for the nice comments to the first part of my article. There are many other things I had to learn by myself, or from talking to friends about their own experiences when going out, and some I learned by watching women in my life doing what they do; first my mom, then my wife, and later my daughter.

1. – If you don’t feel like going out en femme, then don’t. It’s supposed to be enjoyable and not a chore. It will help if you’re able to go out of town to another city or at least a good distance away from your own part of town.
2. – Before going out, turn off your phone or set it to vibrate. You don’t want to have to answer it when you’re within a group of people. Answering an urgent call you have to take using your guy’s voice might not be for the best.
3. – It’s always tempting to tell people about your crossdressing. You should consider, that even if you really trust in somebody, this might be a really juicy piece of gossip and hard not to share. Unless you want everybody in your place of work to find out, it’s better that you don’t tell. Once the cat is out of the bag, there’s no way to put it back in.
4. – Along with the previous point, dressing as a woman for Halloween at the office sounds like fun, but most people expect to see a “man in a dress.” If you look too good, the chances are some people will think it’s more than just a onetime thing for you. It’s best to avoid unless being outed at work won’t have bad consequences.
5. – The sooner you tell your girlfriend/fiancé/wife about your dressing, the better. For many women, crossdressing will be an issue, and if you also add in the fact that you were keeping it secret, their sense of betrayal can be far worse than coming to terms with the idea of you wearing women’s clothes.
6. – Remember that tolerance isn’t the same as support or acceptance. If you have a wife who is tolerant of your dressing, pushing it too far forward might cause some negative outcomes to your relationship. Support and Acceptance can end very quickly if you believe you can do anything you want regardless of what you may have previously agreed on.
7. – Purses and shoes don’t always have to match. The rule about no white shoes after Labor Day or before Memorial Day is outdated.
8. – Keep your accessories and jewelry under control. If you over-accessorize you’ll draw more attention than you may want. Just because you have a lady’s watch doesn’t mean you should wear it with a formal gown. The same can be said in wearing a fancy necklace with a sweatshirt. It’s best to partner the right accessories to attain the right look for the situation you are attending.
9. – One more about shopping… If you act as if you don’t belong in the ladies department, boutique, or elsewhere, then people will react in a similar manner to you. Relax, be calm and confident!
10. – Just because it’s trendy doesn’t mean you have to wear it. Some fashionable items may be all wrong for you and draw unwanted attention.
11. – When out as a woman, if possible, be a good tipper if you’ve received good service. At the nail salon, a restaurant, etc, tipping well is a good way to set things up right for your next visit.
12. – Unless she is fine with it, DO NOT wear your girlfriend/SO/wife’s stuff. Get your own! Many wives would rather burn their clothes than wear them again after they find out their husband wore them.
13. – Make-up is not eternal. After a few months, even expensive stuff will need to be replaced. It does go stale. Don’t plan on using it until it’s gone.
14. – “Perfect hair” usually makes people think of “Wig”. Let it look more natural… Perfect hair is great for a wedding or another big event, but it’s not typical when grocery shopping.
15. – DO NOT, and I repeat, don’t use duct-tape to create cleavage! (I tried it… once. Have a scar to prove it)
16. – If you want to wear a short skirt, be sure you know how to sit properly. It’s best you know how to cross your legs in ladylike fashion.
17. – Please resist the urge in trying to find out what other people might be saying about you, or if they’re pointing fingers, or are purposely ignoring you. Remember, everybody can be “read”. Most of the time, it isn’t a big deal.
18. – At a restaurant, try to order something that can be cut into small bites before eating it. Eating a whole turkey leg tends to mess up your makeup.
19. – Oh yes… breasts. They are not really supposed to be at the same level as your armpits! And the larger they are, the more they tend to hang lower. Don’t push them up so high! Look at the average women and how they carry them!
20. – This should be always on your mind when shopping…. keep your receipts!! If you don’t try things on at the store. , most (at least in the US) will gladly exchange most items of clothing within a few days of your purchase. There’s nothing worse than buying something pricey that doesn’t fit when you try it on at home and then are stuck with it.
21. -For anybody wearing a wig, in particular if you are a tall girl, watch out for low tree branches. I was out with a girlfriend and she lost her hair to a tree… the kind of thing you laugh about much later, but she was mortified at the time.

Remember that priority number one is to be safe. You should enjoy being out, and you can do it, but it does come with the risk of not only being read, but being recognized. It’s always wise to plan your initial outings in places where that risk is minimized and where you can have fun and be safe…

Stepping Out Secrets
The following two tabs change content below.
The clothes I wear do not define who I am. I am the same person regardless if I present as a man in jeans and a plaid shirt or as a woman in a gorgeous gown. That may have been the most important moment in my self awareness. I don’t have a girl side or a guy side competing in one body. When I get to present as a woman I’m being myself as much as I am myself in my every day life. Being able to realize that I don't have to separate my personality in a "Feminine side" and a "masculine side", but that every aspect in me should be integrated into a well balanced persona was very liberating.
  1. Samantha G..... 10 months ago

    Great article Gabriela, spot on advice !!

  2. April Serrano 9 months ago

    Great tips, thank you for sharing!

Leave a reply

Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account