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Beginner’s Tips and Fails in Crossdressing

Beginner’s Tips and Fails in Crossdressing
People start crossdressing for different reasons and in different circumstances.  There is no doubt that the beginning part is usually the most confusing for many crossdressers.

Crossdressing like so many other things in life is different for everyone. Some will crossdress to simply dress up without ever trying to understand it, some will crossdress for sexual reasons, some will crossdress because it simply feels right/natural for them etc.

Giving time to figure out why you like to crossdress will really help you to proceed in the right direction with crossdressing & life. Its okay to be confused or not have the answers straight away. Keep exploring and give it some more time.

Here are some Beginner’s tips and fails in crossdressing that you should know about.

1) One of the most important thing is to Just love yourself and accept yourself for who you truly are. Most crossdressers have guilt problems, hard time accepting themselves and hate themselves for being different. This makes them unable to be happy and will also affect their relationships with others. Don’t feel ashamed or guilty because you like to crossdress. So, come to terms with your crossdressing and have fun.

Beginner crossdressing tips

2) Take your time in learning different things about crossdressing. Don’t rush and try to learn and do everything at once. Take small steps and enjoy every part of it.

3) Picking  your Wardrobe – This is something you’ll have to figure out mostly on your own because each crossdresser have different preferences when it comes to clothing.

crossdressing tip - Picking  your Wardrobe

If you are just starting out, it is best to keep your wardrobe simple. Its a good idea to start with the basics that is padded bra & panties, skirt or a dress, wig and light makeup. Know your body measurements before buying any clothes, this makes a huge difference. 

4) Invest in a good quality hair wig – If you don’t have long hair, you should definitely invest in a nice hair wig.  A good hair wig will do wonders for your feminine appearance overall. Go for the best quality hair wig that you can afford. Don’t buy cheap hair wigs as they never give the feel and look of a nice hair.

Invest in a good quality hair wig


5) Makeup is no doubt a great way to enhance your feminine appearance but it does take a lot of effort. Also, good makeup products don’t come cheap. So, its a good idea to start with Makeup step by step. Begin with Mascara, eyeliner, lipstick and foundation. Learn more >> Makeup Tips for Beginner Crossdresser

Makeup for crossdressers

6) Practice your feminine mannerisms, postures and movements in front of a mirror. This will really help to create a lovely feminine personality. Also, learning to walk in heels properly will boost your feminine confidence.

Crossdressing tip - practice in front of mirror

7) If you want to keep your crossdressing a complete secret, find a really good place to hide your stuffs. Having a lock will be the best alternative. Many crossdressers don’t get caught while being dressed but get caught with the clothes or items they didn’t hide properly.

Crossdressing tip - hide your stuffs properly

8) Connect with other crossdressers & follow confident crossdressers. There are many online platforms like Facebook, reddit, YouTube where you can find many crossdressers to connect with. Having friends with similar interest will make it a lot easier to share, learn and have a great time.

connect with other crossdressers

If you are planning to crossdress in public, remember a few things:

Crossdressing in Public

– Keep your public dressing choices realistic for where you are going. Dress appropriately, wear something that suits your body type, and easy for you to blend in the crowd.  Example: Don’t wear something very tight and revealing while going out for a walk in the park. Keep some regular everyday clothes for when you go out and do normal things. Dress for the occasion. Same goes for the shoes. Wear shoes that match and compliment your outfit.

– Keep your body proportions proper and realistic. You don’t want to step out with massive porn star sized boobs. That makes it pretty obvious. Keep things around the normal size for your body type and shape.

– You are better off if you can blend in with a crowd. Use makeup to enhance your best features but don’t overdo it.

– Practice your feminine postures and movement. Know how to walk like a lady before stepping out.

Click here for more tips >> Tips for Crossdressing in Public

Fails in crossdressing:

– Stealing Clothes.

– Buying clothes without knowing correct measurement of your body.

– Buying too many things at once without proper planning.

– Wearing too much makeup.

– Not taking proper care of your clothes & items.

– Not working on developing your own style and personality.

– Not washing clothes & undergarments timely.

– Wearing very revealing clothing when crossdressing in public.

Hope you liked reading this article. If you think we missed out on something, please let us know in the comments below. Happy Crossdressing!

Facebook Comments


  1. I just went out for the first time in public….omg, I was so nervous but ready! It’s been a long time coming. I have realized that now I don’t care if I pass, I’m happy if you know or even better if you have to look a little closer. Just do you!!

    1. You suddenly realise what you’ve been missing all your life 1st time out, wait while you get some male admirers & then you can really have fun

  2. Been crossdressing most of my life

  3. Been x-dressing my life, wife saw me many years ago and we had “the talk”. We went to a therapist for this and other problems. I told the therapist everything (ok, almost everything). He advised her that there is no cure for my fetish to dress. Either she accept it or end the marriage. We came to a compromise. Unfortunately her medication condition worsened and I stayed home taking care of her. One day I said ” Being that I am now your wife, I may as well dress the part”. She just smiled so I took as a YES. Now I dress whenever I want to (almost everyday) and feel more feminine each and every time that I dress. I’m not hiding it any longer

    1. That is a very sweet story

  4. Interesante

  5. I Just Recently Shaved My Legs For The First Time.. The Best Feeling When Wearing Hosiery Or Just Even Bare…

  6. You suddenly realise what you’ve been missing all your life 1st time out, wait while you get some male admirers & then you can really have fun

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