Easing Into Appearing in Public: Take Small Steps

I haven’t quite developed the confidence to just go out anywhere and do anything en femme, but I’m trying to edge towards that. Most times when I’ve been out, it’s been walking around my neighborhood after about 2 am and before 5 am. In other words, there’s not much chance of me encountering people and potentially having to interact with folks. I’m trying to work up to the idea of being accepted (or at least tolerated) as any other person who is wearing a dress or skirt.

When I first moved into this neighborhood, I was a little apprehensive about what would happen if I went out and then be seen by one of my neighbors. In the next day or a two might they come to me and ask me, “What the heck were you doing? Why?” I wouldn’t have an adequate explanation, because I don’t really know the answer myself. I’d rather not make enemies of my neighbors, or at least not ostracizing myself from them (because you never know when you might need a favor). One day, I just thought, I’m going to do it. If some sort of undesirable encounter were to occur, I’d be sure to make up something plausible. “Oh, I think you’re mistaken; it may have looked like me, but no, it wasn’t. I had someone visiting me overnight. You must have seen them.” Then I could just go back to never going out again; that would be OK. I’ve lived that way for years anyway.

I put on a nondescript shirt and a conservative length, dark-blue, corduroy jumper  (this one actually, except no tights, and athletic shoes instead of flats.) With some trepidation, I ventured outside. I remember eventually standing out in front of my house and thinking, “Hey! Oh my goodness, I’m outside…IN A JUMPER…In FRONT, where people CAN easily see me!”

Every now and then, I again put on something pretty and went outside, “in the middle of the night.” Each time, I stayed out a little longer. I walked down the sidewalk of the dead end street where I lived. One day, I put on this outfit, and went outside. I walked the four houses down to the corner of my street, as I’d done in similar outfits. But instead of returning as I usually had done in the past, I thought, this is going soooo well, just keep on going! I went all the way around the block. I have to say…that it was a sensual feeling as I was aware of the swish, swish, swish of my slip and how the dress moved against my legs as I walked. It was so exciting to have gone so much further than ever before, and importantly, without incident.

After a while, I began feeling that this is all well and good, but…how about taking it to the next level and go out in the daytime? How wonderful it would be to walk around where it’s undeniable that people will see me, if only from a distance. I set out on a mission…to go to the parking lot of one of the local supermarkets  dressed like this. I had a plan…sit in my car until no one was particularly close, get out and walk towards the store. I’d take my cell phone out of my purse, pretend to read a text message on it, and then return to my car…as if the message I’d read was urgent and I needed to return home. I must say…I think it went well.

I’d brought a pair of heels and a pair of flats with me. I wanted to try walking in both, just for the experience of wearing each of them. On the way home, I passed by a Target, which had just recently been in the news on their policy of wanting to be transgender-friendly. I repeated the exercise in the Target parking lot, this time in the other shoes. I didn’t look around as much as I usually do; I kept my eyes straight ahead to watch where I was going. I felt that if I looked around, I might notice people staring at me disapprovingly…ignorance is bliss and all that. Although I may have convinced myself I would feel better, this is probably not the best of strategies. If trouble is headed your way, whether it be someone looking somewhat disapprovingly at you and thinking, “It’s a dude in a dress?” maybe even meaning you harm, or a vehicle headed in your same path, it’s probably better to look around and remain safer overall. It did make me nervous for that reason.

So really, if being out in the public en femme is a goal of yours, you don’t have to tackle it all at once. It’s likely you can start small, in somewhat more controlled conditions. You can try the far-less-likely-to-encounter-people situation of the really early morning, when nearly everyone is likely to be asleep. For other ideas, you can search Web sites and YouTube, and read what our fellow sisters have shared on this site. There are many good tips on how to look better and build up your confidence (such as giving yourself an “out” like the text message thing I thought of). You can keep pushing at your boundaries until you are at the level where you feel comfortable.





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I have been dressing in women's things pretty much ever since, in my early teens, I wondered what the women in some of the first Sheer Energy ads felt like. After I tried on my sisters' pantyhose, my curiosity grew and grew. I would "borrow" more and more things, and eventually decided I wanted to wear whatever I wanted when I was alone (or at night when everyone else was asleep). When I got my own apartment, I was even more free to pursue what it feels like to be in a leotard, dress, skirt, tights, or whatever. With some encouragement from CDH, I have even now been out a little bit in public, to experience a small taste of what it's like to be like women.

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Michelle Liefde

MaryJo, thank you! For the inspiration. I agree small steps do help. I have not gone for a long walk yet but do feel that it will happen. I grow a bit bolder with each little thing I do be it wearing mascara, or a tank top under a sweater or getting the mail in my hallway. Or just walking down the pathway to my door.

Gina Angelo

thank you for sharing your experiences Maryjo. You describe some very realistic steps one can take to make that big leap from private to public. Because of circumstances (spouses, neighborhoods, states etc) not everyone can do it the same way. I went in feet first in the deep end when I first went out, but I did it in a different city from where I live. And my first few times going out were in other cities that I knew were tolerant, and it wasn’t until six months later did I go out locally. So keep at it sister, do… Read more »

Rozalyne Richards

Hi Maryjo thanks for sharing your story with us, my story is just the same i started in small steps, i first started with going out in my back garden and sat down on my swing seat and it was always late at night, then i started to go out in my car always at night too because no-one can see if your a woman or a man at night, the last couple of times I’ve pulled up in a town centre not to near to where i live and did a bit of window shopping, it felt good to… Read more »

karen Jones

Hi I am just new but as I said in my bio I have thought about make overs and they are afew in the GTA. I decided that I would spend my money on makeup and learn myself. So I dressed up simply but pretty and went into my local shoppers drug mart and ask for help with my makeup. Without any questions the clerk sat me down and we did my makeup. 2 hrs later I am done purchased my stuff and went to the mall. It was nervous at first then I was fine and proud to walk… Read more »

Gisela Claudine

Thanks for sharing MaryJo. I love your enthusiasm. It’s inspiring. Nice tips.
I haven’t reach that point but I would like to do it occasionally. I have been out in my back garden who is very secluded. Once I was made up by a female friend which is an experience I would share some day. It was once and it has not been repeated. Although I have wrote a few poems in where somehow I have caught the feeling. At least I tried.
I think I would choose a place away from home for that.
I really liked your article.


Baby steps my dear! What a fantastic situation you have. My 2 cents: If the only thing holding you back is your fear of what to say when asked,”why?” Your answer is simple, “it makes you happy.” Those that want to be around you will continue to be around and the others won’t. Be bold. I found the key is to blend in and not attract too much attention. I mean mini skirts, bullet bra, and 5 inch heels might send a different message than some ankle jeans, a loose top, and low healed wedges. Look around you and see… Read more »

Camryn Occasionnel

Hey Maryjo, enjoyed reading about your experiences in easing into public view. Coward that I am, I can’t even imagine at this point crossing the threshold of my front door en femme to get to my car!! So you’re already much further along than I am. I have no idea when I might summon up the courage to advance as far as you have. But I plan to spend the next half year or so trying to evolve a more convincing female image. When, IF, I can get that done to my own satisfaction, I think what I will do… Read more »

Jacky Burnside

Maryjo, I can totally relate! After a lifetime of cding in secret, I have also begun to appear publicly dressed as a woman. It is very exciting, but scary as H…!
Go for it Girl! xxx


Thank you Maryjo for your wonderful story. Baby steps definately do work. I started taking mine about 5 years ago and to this day, everytime I do go out, it still feels like the first time. People I come across either don’t notice or don’t care. I go out on the average of at least 3 times a week and I am still getting use to it. However, each time I do go out, when I first step out of the car, I am about as nervous as a long tail cat in a room full of rocking chairs. But… Read more »


I’d say your doing it Right—one step at a time-to avoid tripping–Going with a spouse or freind can also make you feel safe–I(n my early days of Really dressing ) wife would do me up & we would drive out of town where people would’nt know me–we would do things like stop & I’d pump the gas & go inside to pay–stop at a store & I’d go get pop/water or whatever—sometimes go through a drive through get food & find a park or rest area sit at a picnic table & eat—then it got to stopping & going into… Read more »

Chrissy Landwer

You’re very brave and I hope you get stronger at achieving your goals. I know it’s awkward and I am dealing with some issues as well. I love all fem. and can never reveal this to anyone at home or work. My best advise is to get with other who share similar interests and dress and go out together.
Gook luck,

Michelle Phillips

Thanks for sharing Maryjo. My story is a little different. I have an awesome spouse who understands and supports me. We go shopping together, etc. Well I decided I was going out in public last week. We had already booked seats at a pro-wrestling event and I decided what the heck…Michelle is going. We spent all day shopping, getting our eyebrows done and then my bride really did me justice with makeup. Yea, I got a lot of looks and whispers but I just didnt care. It waant about being pretty or accepted….it was about me expressing my feminine side.… Read more »


It’s all about the small steps, but they are also giant steps! You are an inspiration! And your outfit is just too cute for words!

Brianna Rain
Active Member

Maryjo, thanks for this article. It’s very inspiring and I hope I can gather up the courage to take small steps of being out in public like you have.

Laura Lovett

The first walk I had as Laura was around a recreation ground at around 2.30 in the afternoon. I saw 2 other people, one in the distance, the other a lady walking her dog, who was coming down the path I was walking up, so unavoidable. As I approached the very first person I had met who wasn’t my wife, while dressed entirely in women’s clothing, badly made up and as obvious a MIAD as you could hope to see, I felt very nervous, but determined to exercise my right to be myself, and also determined to let her enjoy… Read more »

Lindsay Freeman

Do what makes you comfortable I have gone to get several pedicures en femme .Fully dressed from head to toe including jewelry and favorite perfume.


Here’s my advice. Baby steps..to be sure. But here’s what makes my public appearances work…a giant step. I save up some cash and pay for professional hair and makeup. I keep the cost and the anxiety down by finding private makeup & hair pros on Kijiji or Craig’s List. I would hesitate to go to a dedicated crossdressing makeover studio. They can be expensive and not that great. One I went to on Gerrard St. in Toronto was a giant disappointment. Their binder of “looks” lokked tacky and “drag queenish”. The makeup station looked sketchy and I walked out. Fortunately… Read more »


I love your story. oh my!!

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