Top 5 tips to be a happy crossdresser 22

I guess I’ve been crossdressing for a while now, and I suppose I’ve come to a few conclusions about things. Here’s my top 5 tips for being a happy crossdresser – they’ve worked for me so far :D

1 – Accept it

This is who you are. Regardless of what anyone else might think, there is nothing wrong with wanting to dress/look like a woman. You are not a freak. You are 100% the standard, normal, wonky human being that everyone else is. There is nothing wrong with you. I’ve never heard of anyone whose urges to dress dried up completely. Trying to bury or ignore a fundamental part of your personality will only lead to depression and darkness. It took me a while to accept myself, but if I can do it, so can you :)

2 – Figure out what you want, and work towards it

Some people only want to take things as far as wearing panties under their regular clothes. Others, such as myself, feel it necessary to go out and about into the world fully dressed. And there’s plenty more people in-between. These things are all OK. If these are things you want to do, but you feel like you can’t do them… you’re probably wrong. It’s been done. If you want to go out dressed, you can! But take baby-steps, and always consider your safety. If you feel like you’re in an area where you don’t think you’ll be accepted, take a vacation to somewhere better! Move! Change jobs! Meet new people who don’t care what you wear, but only care who you are as a person. It’s your life. You’re not hurting anyone. You have the right to be happy, and ability to make it happen.

3 – Don’t obsess about passing

Some girls will always be prettier than you. You might be thinking “But Liz, you’re so pretty!” – and that may or may not be true, but I still have severe issues with how I look, and will always look at other girls and think to myself “I wish I was as pretty as her”. I’m pretty certain I don’t pass in real life, but you know what – that’s ok. I’m taller than most girls when I’m wearing flats, and I almost always wear high heels, which puts me way above the norm. I have somewhat wide shoulders and an indelicate jaw, and I don’t even try doing a feminine voice. But, as it turns out, most people will either not notice at all, or glance over curiously for a moment or two before they get back to their own lives.


I have some reasonable makeup skills now, but I didn’t used to. It took time, and patience to get to a point where I felt like I could apply my own makeup and not look like an idiot. If you try putting on lipstick for the first time, and it doesn’t look right… congratulations! You’ve successfully figured out that sometimes lipstick doesn’t look good! Now you can work from there to figure out how to do it properly :D If you want a femme-voice, you have to practice. If you want to figure out how to walk in heels, you have to practice. If you want to define your eyebrows and not end up looking like a neanderthal, YOU HAVE TO PRACTICE. No one is born with these skills.

5 – Be honest

If point 1 was being honest with yourself, then point 5 is being honest with other people. I’ve heard so many stories of people lying, whether outright or by omission, about their crossdressing, and having their relationships break down because of it. Crossdressing may be a big deal to them, in which case they’ll hate you for lying about it when they find out, or it may not be a big deal at all, but they’ll still be upset that you kept something from them. My wife knew years before we were even involved that I was a crossdresser. If she found it disgusting, well, maybe we wouldn’t’ve been friends, and maybe I wouldn’t found someone who *was* accepting of it. But you need to give yourself the opportunity to find that person, and give other people the opportunity to decide it’s not for them. If you want a happy relationship… Honesty will always be the key



Take a look at my guide on how to cross-dress, or maybe see my makeup-guide for crossdressers. If you’re more interested in pics, click here to see them :)

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22 thoughts on “Top 5 tips to be a happy crossdresser

  • Natassia Crystal

    I can only agree with these tips! :)

    Though, I’d probably would make a few nuances on point 5 for the older married CD’s among us.. since they usually grew up in a world that was much more hostile towards anything CD-related.

    In the modern Western world, it’s not an unknown phenomenon anymore.. so you’re better off telling partner (although, I still will not judge if one doesn’t.. because it’s just a very difficult thing).

    Great post!

    • Liz Summers Post author

      It’s definitely very difficult, I totally agree! It’s hard though – I feel like whenever I talk to older CDs, they definitely feel the burden of being dishonest, and so the best advice I could give to anyone here on in… don’t put yourself in that position, because you’ll feel awful


  • Letizia

    That`s it. I agree absolutely.
    Rule 1 is the key. The older I get as a CD the less I am dependent on the opinion of other people. I am what I am.
    That makes me feel free and self-determined. I am proud to be a part of a world wide CD-Family.
    Your posts make me happy and relaxed.

  • joanna

    Wonderful advice with the first tip being by far the most important. Needing to do this while feeling like a freak is no way to live life. Everyone should heed your words…bravo…, Joanna

  • Carla Contini

    It was so much easier when I was younger and passed effortlessly – all I had to do was throw on a dress and curl my hair. Now it’s so much harder, I need to use makeup and I need to choose my outfits really carefully. Anyway I lost my last female partner because I came out to her and she said she could deal with it, but she couldn’t. So I have resolved not to come out to my new partner, she would never understand. She likes my feminine side but she doesn’t see the extent of it. It doesn’t make me depressed. But I’m bisexual and I miss being in female mode and having sex with men. So nowadays I just keep everything in storage; I make up a story about traveling for work and get a hotel room every once in a while so I can dress, go out for dinner, a movie, a few drinks, chat with some guys etc. But no sex, I would never do that to my partner. In the end you just have to accept that you can’t have it all. If you care about the people around you, you have to rein in your desires.

    • robert hathaway

      im 72 and I stii dress on the weekends as a female and yes it is hard to make myself look beautiful but I do and I still wear high hels with a 5or 6 inch heel

    • Liz Summers Post author

      I don’t know what you mean about the dresses. Going out on the street? Just have to be brave :) and smart! Don’t do anything that you think might get you in trouble

  • Acsde

    Hi I feel a waman inside me and I need to be crossdressing. I love to wear peter pan collar or high collar dresses with back button or zipper. Please tell me how to wear it

    • Liz Summers Post author

      Hi you made a similar comment recently – I still don’t know what you want from me! I answered already :) just wear it! If you’re looking for styling advice, I have no idea!

  • Tammy

    Hi Liz I am a crossdresser and LOVE it. But I have a problem. I am married and she in NO WAY goes for this. She thinks it is sick and if I were to come out that would be it. I have been married for 40 years and frustrated. I dress when she is out. I am now at a point where I need to dress more and I am unhappy. I have been chatting with another CD for quite some time and she said I can come there and dress. I know there would be touching, kissing etc. . BUT I definitely said there would be no anal sex. And she is quite comfortable with this. I am this close to going. I have to get rid of this frustration and enjoy some life I love before I die. What do you think?

    • Liz Summers Post author

      If your wife is comfortable with you going and spending time with, and being physical with, this other CD, then I think it’s fine.
      If your wife is being kept in the dark, which is seems like she is, then no, I definitely cannot condone that behaviour!

      I can’t tell you what to do – you need to follow your own moral compass. But ask yourself this: Is the possibility of destroying your marriage worth it, in the event that she finds out? Do you think you can live with the guilt of knowing you cheated on your wife?

  • Leigh Ann

    Hi, I had a friend tell me about your blog. Like most cd’s, I started in my early teens, fought it tooth and nail. Nothing new there. I married at 25, I did not tell my wife until about 20yrs of marriage. Hardest thing I ever did, afraid of losing my best friend, hurting her, losing her faith in me as her husband, lover, companion. After about 5 years, she has stuck with me, and at times, even embrace it. Other times, she finds her self in a shell, and I believe ashamed. She has told me she wants somebody to talk to about it. She is the only one I have known, that I have told about it, no family, no close friends, just her. I have been trying to find wife’s of cross dressers that she can confide with. So she too can understand a bit better, and just laugh, cry, share our joy, and heart ache. Do you know of any such group, website. She dosent want to go to any local groups of fear of my secret ruining my career, as Richmond VA is one of the biggest smallest city’s in the US, and with our jobs, we know Very Many people. Please help if you can
    Thank you, Leigh

  • Satbir Redhu

    Crossdressing is my will and i am proud to a crossdresser. I openly accept myself as crossdresser. When i am at office i am a man but at my home i am always woman. Senior ladies in my neighboudhood always like me and encourage me to do so by telling me ‘U are not doing anything wrong’

  • Susan

    I’m probably too old and too tall and too manly to do this whole “cross dressing” thing, but I just love the clothes! I love acting
    feminine! I love wearing lingerie. Oh, well.