Learn how to pass as a woman

Have you been out dressed in public before?

If you have you probably know the fear that comes with taking those first steps out into the world, and the constant anxiety of being read. Passing in public is the holy grail for crossdressers, but too many see it as an impossible challenge far out of reach. It doesn’t have to be.

On Crossdresser Heaven you’ll find many articles on how to crossdress – you’ll learn about the importance of smiling, how you carry yourself and the subtle cues that give your secret away. What you wear can be just as important as your mannerisms and voice. As you browse the site you’ll find advice on how to choose the appropriate clothes, as well as where to find larger size clothes and shoes that will fit you better.

If anything stands out about our community it is the sisterhood that we share. We learn and grow together – our mistakes and discoveries make it easier for those who follow to blossom. So instead of writing another article on how to crossdress, I want to hear from you:

What works for you? How do you ensure that you pass in public? How do you react if you’re read?

I encourage you to take a moment to share some of the wisdom you’ve acquired in your journey. It might just be the distinction that a new girl needs to get her started.

Advice for how to pass as a woman

From the Crossdresser Heaven community: – scroll down to the comments to see the advice and add your own!

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  1. Gracie Garcia 3 months ago

    I was apprehensive the first few time I stepped out dressed. The first time trying something new is like that. Overall I had no problems and people made no comments or pointed fingers. Actually no one paid attention or noticed for the most part. Those that did glanced or smiled approvingly which gave me confidence. Houston and here in San Antonio are very gay friendly but attitudes in Texas are changing and some of my old fears are coming back.

  2. Rebecca Williams 2 years ago

    I have been going to a group I Phoenix called Arizona Tgirls. This gives me a chance to go out without people giving me a hard time. It also gives me more confidence to go out. I suggest that if you have a group like this in your area that you join them.

  3. Debbie 2 years ago

    Debbie here again, thought you might be interested, I was out again last night (the weather was terrible ) however the bar staff and the few customers who were in secrets bar on Scotswood Rd, we’re really friendly. I will be going there again.It felt so right I only wish that I could go anywhere and be myself.give it time and who knows.

  4. Debbie 2 years ago

    Hi everyone! Just thought you might be interested in knowing I have been dressing secretly for years (I’m 68) now on hormones. I have started going out dressed ln Newcastle upon Tyne for the last few weeks at night to bars in the gay area. I do not pass yet but it is getting better each time I go out. I love it it feels so right.I am married and my wife knows and shops with me.However my grownup children do not.

  5. Sallysim 2 years ago

    My first outing was with my girlfriend just a few weeks ago. We went to the local 24 hour supermarket after we finished work at midnight. I was a bit apprehensive at first but then began to feel so at ease as we shopped for clothes etc. Nobody there including staff gave me a second glance, if they did I didn’t notice. Except one of our customers in the pub saw us and called me by my drab name but even he didn’t make a big issue of it. We’ve been out a few times since and I’ve been out on my own en femme with her encouragement. But we still plan to go out for the day or to a restaurant for a meal as soon as time will allow. I’m desperate to go out more I feel so free and confident. I’ve not had a bad experience yet but I’m sure I will have someday. But look forward to bringing Sally to the fore this new year. Ok I get some stick from my customers ( we run a pub) so it makes things a bit more difficult as you don’t get much privacy. But I use our weekly auiz night as a release as Sally hosts the quiz. At first there was a bit of ridicule but I’ve had lots of support and good comments from both staff and customers alike. Some say I look better as a woman than a drab man and others say do what you feel good with which is encouraging
    I think 2016 is going to be Sally’s year
    Take care everyone out there love to you all.
    Sally S xxx

  6. Toni Ginamaria 2 years ago

    My first outings back in 1990 were to gay bars hair dressers and shops out of town. I would go out Dressed As a Boy DRAB first and later in the day in DRAG. My spidey sense was off the charts, but as nothing bad happen and what did I could handle, I became more relaxed. I got drinks bought for me doors opened and cigarettes lit propositioned by some, other times I would attract admirers that would hang around and look down at their feet and talk awkwardly till I would take the lead and flirt and reassure them. I would smile look them in their eyes play with my hair and brush against their arm or touch them on the thigh. Eventually I would go shopping ask for advice and try on in the dressing room before purchasing. I wore 4″ heels around the house and packed flat slippers in my purse. I practiced my make-up skills, went for applications at the hair stylist and department stores. The advice I got was to prep my skin shave clean tone moisturize. As for make-up less is more. My girlfriend would tell me that department stores work on commission drug stores are more affordable and you can return anything that doesn’t work. Note I have never before returned anything, ever. Go easy on the eye make-up, less slutty/ clownish rather more natural, better appearance to blend in with natural women. Watch how other women dress in the places you are going. No leather outfits short skirts and high heels at the grocery store. Try to copy to blend in and not to stand out. Sweater if you don’t yet shave your cheat & arms tank top cardigan or blazer if you do, jeans and mid-heel boots or flat unisex shoe. My mom advice: go easy on the perfume to always stand up straight look people in the eye, ask for things in the form of a question smile often and say thank you. And finally don’t worry about what other people think unless they pay your bills. Get dressed put on your make-up and a touch of perfume grab your purse and go out stay safe and have fun.

  7. Amanda 2 years ago

    I usually only go out dressed at Halloween, Mardi Gras, or to a fetish ball. So about three times a year. I spend months anticipating. I went out with a lesbian friend once to a club. That was fun, but I didn’t pass. I don’t think I could ever “pass”.
    I ,do, wear womens shoes most of the time, and I shave my legs. The shoes are mostly unisex type such as penny loafers or knee boots that I wear under my jeans.

    Smiles
    Amanda

  8. John 2 years ago

    I love to walk around the house in my sundresses when no one is home or go outside on the back deck. I’ve never tried just driving around at night or anything else

  9. Janine 2 years ago

    I have been going out dressed for a couple of years.
    The more that I do it the easier it is.
    The hardest thing for me was getting makeup to look right.
    Finally I decided to go out dressed and go to a mall and find a store that offers to do makeup.
    I was extremely nervous about doing it but once I got to the mall and went into the JC Penny’s I found what I was looking for.
    There were three girls who worked there who did makeup and only one of them was busy.
    Taking a deep breath I chose a girl who was about nineteen or twenty and walked up to her and in my softest voice I smiled at her and told her that I wanted her to show me how to put on makeup on.
    She realized that I was a man dressed as a woman but didn’t seem to mind.
    I got seated in the chair and she went to work on my face.
    She removed the makeup that I was wearing and started with a beard concealer .
    I watched her as she was doing my eyes and lips until she had transformed me into a fairly good looking girl.
    While she was working on me she was explaining what she was doing and what she was using on me.
    After about a half hour I couldn’t believe how good that she had made me look.
    I bought a hundred dollars with of the makeup she was using and as I got up to leave I thanked her and tipped her Generously as I walked away with a new sense of confidence.
    That one time taught me a lot of things so that I could do my makeup a whole lot easier and quicker
    If you can get past the embarrassment of asking for help you will never regret it.
    I know that I didn’t.

    • Erica 2 years ago

      Next Wednesday I am planning for a morning and afternoon and getting out! I made an appointment to go to a Spa and have them do it! I can then change there an be on my merry way. The price is $35 and I think that’s reasonable. How much to tip?

    • Karri Roses 2 months ago

      Great story, Janie!! I commend you for having the courage to ask for help in putting on makeup. I think if I did what you did, I would do it on the other side of the city where I live so no one I know would recognize me.

  10. Gazzmen 2 years ago

    Gone out fully dressed twice both on halloween one to the store got ,lots of smiles not passable once to a gay friendly neighborhood very exciting

  11. Sharelee 2 years ago

    I have been out several times in Newcastle city centre by day and the metrocentre ( once). Apart from a few rude and ignorant ‘amazon’ women, most people are ok when they realise I am not a real woman. I still have to be aware of groups of young lads, but most times I can see them coming and avoid. I have found that dressing down in flat shoes, but still with a short skirt and thick tights with a little more subtle make up, helps me to blend in and not get embarrassingly noticed. I have a big nose and an ugly face, so I do get ‘read’, but I need to be a woman so much, I have to go out. It’s not just a sexual kick, but a deep need to let that woman inside me out! I still dream of being a real girl, even though I am 57 and a father of two teenage girls. My wife does not allow me to tell them or anyone of my habit and says she couldn’t cope if I ‘came out’. I can’t risk my marriage or my children’s contempt, but my feelings get harder to cope with as I get older. I feel unfulfilled and unhappy, as my menopausal wife has not wanted sex since 2008 (nothing to do with my dressing either). I have not cheated on her, by the way. Anyone any advice?
    Sharelee x

  12. lisa 2 years ago

    i like to drive around at night in a tight sweater, i use water balloons for boobs cause i like the way they jiggle, full make-up and a wig and of course my high heels. Sometimes i’ll stop and walk around not far from my car just so i can hear my heels on the pavement. I like how you always have to adjust your bra straps and pantyhose. It’s funny how as soon as i step into my panties my penis knows to turn into a clitty, and it won’t turn back till i get home and pull my panties down.

    • Gabby 8 months ago

      I too luv to drive around dressed up, showing cleavage , I tried to pull up next to bus drivers or truckers showing my cleavage and Sexy legs, makes me feel naughty and really sexy

  13. sammy magdaleno 2 years ago

    When i crossdress i go to the cemetery or to a public park & i usually wear a short sexy flary floral skirt with a pair of satin panties underneath my skirt & a long sexy auburn red wig. I always pass for a sexy woman bcuz i aways get stares & whistles especially from the mexican workers at the cemetery so i usually bend over a little to get a closer look at a plot & the workers always get behind me & all of sudden start digging for weeds as they’re looking up my skirt trying to see my panties. That’s when i bend over even more so they can really get a good view of my sexy satin red panties under my skirt. One time i was so bent over that the wind lifted up my skirt above my waist & my underwear was fully exposed & i even heard the worker say whoa! really loud to himself. That’s when i stood up & pulled my skirt back down & smoothed my skirt. I looked at him & he had a big smile on his face. I got the hell out of there & as i was walking away i heard him say out loud “nice panties!” I guess i showed a little too much but as nervous as i was, i really got turned on & i enjoyed the whole experience.

    • Joann1947 2 years ago

      I like to go out in my car and flash truck drivers they like it and it really turns me on next time I am going to try to get one to stop and I will see what happens

    • Ariana Merona 7 months ago

      OMG that sounds so hot!

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