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!”

Transgender Heaven - Gender Journey

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.





  1. Dani 7 months ago

    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. I had a blast. I no longer fear going in public. Michelle is here!

  2. Helena 7 months ago

    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!

  3. Brianna Rain 7 months ago

    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.

  4. Laura Lovett 7 months ago

    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 her right to be herself.
    I first observed her dog, which took no notice of me, being more interested in sniffing around, then glanced at her with as natural a smile as I could muster.

    She smiled back, quite broadly, and said “Hello”.

    Until that moment, her look had been one of quiet melancholy, and, as I echoed her hello in a husky voice, reflected that her smile was either for me or at me – either way, I felt responsible for bringing the smile to her face, even for that short moment.

    That small thing brought what I can only describe as a smile inside. My whole feminine being lit up with a smile and I felt glad to be Laura.

    Enjoy the little things. They are essential parts of the bigger picture. The small steps become bigger steps as the confidence increases.

    I have since done bigger things and am looking forward to the next with excitement.

    Love Laura.

  5. Lindsay Freeman 7 months ago

    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.

  6. Harietta 7 months ago

    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 I got a fab airbrush makeup (free) demo at Sephora in The Eatons’ Centre not far away and my drag day was not ruined. In fact I had coffee with the MU artist after.
    But my advice..if you want to go (out) in confidence save up some dough and pay for a pro.

  7. Johnanna 7 months ago

    I love your story. oh my!!

  8. Morgan Staar 5 months ago

    nice article..I was fortunate to have a friend that forced me to test my limits…first a walk to the park, then the mall, then lunch at the mall, met some of his friends, basketball game at his school on a friday nite, the first dance, school picnic…every weekend was a wonderfully scarey adventure….your one your way…enjoy

  9. Sophie Valcar 5 months ago

    l know exactly how you feel but with me l don’t feel confident yet to go out because l feel my makeup is bad and l walk like a men and yes lam practice both .It’s funny because you want to be like all the other girls just get up and go right. l know l will get there in the end. many thanks to you.for till us your story take care. love Sophia

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