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I recently reached a crossdressing milestone in my life. Twenty-five years of going out dressed as a woman, or more accurately, going out as the woman I feel is within has recently given me cause to reflect on those experiences. I'm talking about being in a public setting where I am not in control of who I may or may not run into.
Like many of us, my dressing began in private and remained that way for many years. Walking around in heels and a skirt in a safe place was only partially satisfying, and so I had resigned myself to a life of closet-dressing. I attended group meetings where several of us rented a large hotel suite where we were able to dress and hang out together. We were all pretty much in the same situation. As much as I enjoyed this, it seemed as if it were only a much bigger closet; I wanted more. Slowly, often very slowly, I went out more, often in the comfort of other crossdressers, and always taking care to be very discrete. I would look over my shoulder and carefully observe my surroundings, hoping not to cast too much of a shadow.
With time, I felt as if I could pass. I became more comfortable going shopping and dining out. One could say that practice makes perfect. The routine of going to places and doing activities, especially shopping, helped me find a level of comfort. My excursions have been very enjoyable and uneventful and rarely have there been much in the way of interactions with people when out. Again, I have been somewhat invisible, so to claim I was passing may not be accurate, especially if my presence was hardly noticed or not at all.
There were circumstances where interactions occurred, mostly with women, but also men, and they allowed me to become more confident, at least I didn't feel the need to avoid interaction, and I actually found it interesting, delightful, a part of the feminine experience. One time a woman approached me while shopping and asked my opinion on something, I wanted to look around to see who she was talking to. Rather tentatively, I gave my opinion. She was delighted to carry on with the conversation about the selections, color choices, and apparently oblivious to my presentation or didn’t care in the least. It was the first of many, and each one that followed became a little easier. Over time, it presented to me a feeling of validation that I was real. Not only real but worthy of being there, as well as being seen and heard.
Recently, I had an opportunity to meet with a friend who is much like I once was but wants to branch out and live more freely as herself. We met for coffee and immediately she wanted to know how I could do it. How could I just walk into a department store, try on clothes and shoes, when I was taller, had a deeper voice, etc., without being scared? What I told her was that it’s perfectly okay, and in most cases, no one really brothers trying to determine if she is really a woman, if they even noticed her at all.
She wasn’t buying my advice and couldn’t relate to my experience. I invited her to go shopping with me. Reluctantly, she agreed. She did browse and found a couple of items, but she could not bring herself to go through the checkout, instead, asking me to pay for her. It was clear that she was much more nervous than I realized, and she didn't think she would try it again.
I really wanted to help her, feeling as if I failed her by not relating how my confidence had been gained over time. What could I say or show her that would help her gain that same confidence and enjoy herself fully as the woman she felt she was?
I’m told that I pass very well, and as such, I try to dress and act appropriately for my age. I ask myself what it is that allows me to successfully go to the grocery store, shopping, etc. What can I pass along to my friend? Passing is a big part of it, but I see women whose appearance suggests less effort at being deemed to be dressed age-appropriately. So, part of the answer is not in passing, but in one’s confidence. Having the capacity to show up however you desire. In no particular order or level of precedence, this is how I am trying to help my friend achieve her goal of going out in confidence and safety.
We are somewhat fortunate to live in a time where being dressed in the clothes of the opposite sex is no longer a violation of the law. Culturally, it is still at odds with what many people expect.
Take care not to stand out too much. If you are going to a familiar place, take notes on what women are wearing in those places. A Cis-woman can get away with wearing almost anything, but for a non-Cis woman, something comfortable, not fussy, or unmanageable is best. I love getting a bit more dolled up and glamorous, but I avoid stopping by the hardware store or garden center in heels.
Familiarize yourself with the places you will go to. Maybe even visit them discretely while in male mode to learn what the place is like or when the best time is to visit or is it crowded, who are the clientele. It has been my experience that I received more acceptance and felt more comfortable in places where I was mostly in the company of women. Women have noticed something that might give me away, but they have always been discrete about it. I have also witnessed men who have seemed somewhat uncomfortable, but nothing happened.
Pay with cash if you are uncomfortable tendering a credit card with a male name. Smile! Women often smile and greet other women, so be prepared to return the smile.
If concerned about catastrophic circumstances, car trouble, unable to return home incognito, carry makeup wipes and a change of clothes.
Check for gender non-discrimination support in-store policies and local ordinances. There is no guarantee, but many companies provide training to employees to avoid discrimination. In the beginning, visit places that have inclusive policies.
Last but not least, it’s likely that you won’t experience violence while shopping; it is still a possibility. It is necessary to give it some consideration.
Several of my first outings were Halloween and Costume balls. There was no question that I was en femme and obviously crossdressed for all the world to see. It was somewhat desensitizing being seen that way as if I were part of a joke or gag. It did give me an opportunity to gain some of that much-needed confidence.
Be confident, be yourself, and maybe you'll have some wonderful experiences of your own to share.
This article was written a few years ago. Some progress has occurred.
Familiarize yourself with the places you will go to. Maybe even visit them discretely while in male mode to learn what the place is like or when the best time is to visit or is it crowded, who are the clientele.
Go on Google Maps and look for the graph showing busy times and if the location is currently busier than normal. Isn't real-time data wonderful? 📊
Pay with cash if you are uncomfortable tendering a credit card with a male name.
It isn't all that difficult, nowadays, to get a credit card with a female name. Search CDH for "Credit card femme" and you will find instructions and tips about how to get one of your own.
Carla, thank you for your lovely article, so nicely written. You are so right that with the right confidence to can go most anywhere en femme.
It's great you were trying to help another girl to be able to show her feminine side in public.
I cannot explain what drove me to go out, but I think it's much as you have described, an affirmation of being feminine.
Amy
Very good story, Carla! Being selective of which stores to visit is so important and can make or break one's confidence. I might add that choosing what to wear is equally critical.
Dress like a shopper, not a stripper!
Reading about the woman who came up and asked your opinion made me chuckle. Perhaps she was one of us but you didn't know it? Maybe she walked away and thought, "Hmmm, I wonder if she...?"
I love “Dress like a shopper, not like a stripper.” Great advice, I wish I would have benefitted from.
a little shopping tip-call your credit card company and ask for another card for your significant other. they will ask for her SSAN but just advise them that she is not a citizen thus no #
Hi Carla, Jane from Hobart Tasmania. I recently joined a club in Sydney, called Seahorse. We had our Christmas party, at a club. So Thete I was, dolled up, the first time in public. My beautiful wife alongside. I got to the club entrance, and entered via a side door.
I chickened out a little, but regained composure. Met my new friends. Other people not with our group joined our table.
I learnt to be proud of how I can look, be open, and kind. Have fun.
Thankyou.
Jane Stewart
Thank you Carla for your article. It was right on the money. I first started going out in the early 80s. It was a different atmosphere then how it is now. I remember sales persons following me around the store. I remember a security guard following me out of a store and calling the police. I have no idea what for, but I left the area just as a police car arrived.
I love going out shopping. It is such a nice feeling being myself.
Yours Terri
OMG!!!
I can relate to SO much of what you wrote!
I'm personally in a 'place' right now wherein I'm wanting to make some serious changes.
Shopping, going out, and being among GF's that are supportive has been huge for me, but I'm wanting to take a much bigger step.
I truly feel for your friend's apprehensions. I mean, this is very personal stuff that, in many peoples' lives could be embarrassing, shameful (dependent on their state of mind), or in actuality HARMFUL to their family, their job, or even their sanity.
I think for me, I've come to a point where I'm ready to shed my fear, and EXIST.
Carla, thank you for this post! It was beautifully written, engaging, and touching!
Valerie
Valerie,
Your concerns are valid and warranted. It is a shame, that we often have to subjugate our dreams and desires, to protect and care for those we care for and ourselves. There is certainly some of this in my life and the lives of others, so it is a juggling act we all have to negotiate with care and prudence.
Carla, great article, I totally agree it’s all about confidence and dressing your age, which doesn’t mean dressing so no one notices you. Classy but still a bit sexy is what I aim for at my age (64), show less by day, more by night. And yes the women I have encountered have been fab, especially shop assistants, very supportive. In Sydney there are a few small groups of gurls that get together and are very supportive. Sadly COVID has severely limited group outings.
Luv Nikki
Thank you Nikki,
I only wish what I offered was more helpful. Everyone’s situations are so different, and I am grateful that mine have been mostly positive.
Thank you for sharing your intriguing account of your journey.
It struck me that when presenting as the woman you feel you are, your interactions have been more with women than with men.
While I have not yet ventured farther than my driveway and front gate en femme (and certainly not in bright sunlight), I have found that I am more comfortable interacting with women - even if I think they realize that I am a man dressed as a woman.
So far, my "interactions" with women while en femme have amounted to my exchanging a friendly - but very brief - greeting with one or two ladies passing my front gate on their way to or from work - usually in the dim light of early morning or evening.
Whenever I sense a man making his way up the street, I panic and quickly make my way back inside the house.
I am unable to explain this to myself and wonder whether any of the other gurls here have a similar experience?
Love, Katherine
Katherine, I can relate to your discomfort with men. Even the men that know and accept Carla, still have a level of confusion and discomfort. My sense is, that the idea of giving up male privilege and power, is so foreign that they can’t begin to understand it. I hope with time you find more comfort and enjoyment in expressing your “Whole self”.
I also think part of what unnerves men is when they find themselves attracted to a genetic male presenting as female, they question their own sexuality and feel threatened. It's sad that they can't realize that the image so many of us strive for is to look as much as possible like an attractive woman, so that reaction should be expected and is nothing to be embarrassed about!
That's a lot of what unnerves me, and I like crossdressing.
But for all my married life I was unnerved by pretty women too.
When I ever dress successfully, I think I unnerve myself.
It's complicated but fun.
It makes my day to get a reply from one of you beauties. Thanks.
You are one of the few who really rocks the strawberry blonde hair.
Aw...that's so sweet! It's funny because I used to think there was just no way I would ever consider going blonde at all, but I think the more reddish tone is what attracted me to this color, and I don't know I'd go back to brown. Thank you so much!
Well done Carla. We got to get together one of these days
Great article, and you look so natural! I would never even think you weren't a cis-woman based on that photo. I can relate very well to this article, as I'm just started venturing out in girl-mode this past year (the mask mandates actually do wonders from my confidence!). I've been mis-gendered a few times, but got "ma'am'd" just last week.
One thing I find particularly tricky when choosing how to dress for normal activities like shopping is that you want to not over-dress, but I find that leaning more towards the ultra-femme side (without going overboard) helps with "passing." The times I've been misgendered have been because I chose pants, very minimal makeup, etc. (never mind the boobs, hair, and jewelry - come on, people!). So I find casual skirts, maybe a mid-heel boot, these things help maintain the image without sticking out like a sore thumb!
I have to agree with wearing a mask has its advantages of obscuring somethings we might otherwise need to attend to, but it also hides that so important “Smile” that can be exchanged, especially with other women, that says, “I see you, I accept you”.
Very true. Especially because I certainly feel like I look more feminine when I smile. Hopefully, someday, we'll get there...
I would love to go shopping with you if we lived anywhere close together! Your article was wonderful and I relate to so many things you said. I am not as advanced as you but I see my own experience as a earlier version of yourself. I've started to imagine myself as more than a guy that dresses up. The real me has feminine elements and my dressing is a reflection of who I am. Hiding my dressing is hiding myself.Although not completely convinced myself, that's how I see the situation. I wish there were other girls located near me that I could meet and chat with...Thanks for the excellent article.
Wonderful suggestions and thanks for sharing more of your story.,
Such a great story, Carla. I hope your story and insight gives others the courage to go out and just do it. I know for me I was here t CDH almost a year reading all the wonderful adventures before I went out and had my first big adventure. I went out and had my hair colored while I was dressed en femme. I did this in a city almost an hour away.
Now in the last 4 months (in the city where I have worked for over 40 years) I have had my hair colored, nails done (3 times now) and gone mall walking. The mall is only a few minutes walking distance from a lot of my customers homes.
The stories here have helped give me the courage for this, but I still want more and come out to more people on my life.
I to like Fiona would love someone to go out shopping with, or share a meal with.
. . .Cassie
I've been out in public only for the past three years, and loved the initial thrill. Now I feel very comfortable in my female identity and during the Covid lockdown from my job, working at home, I dressed en femme every day and went to shop, go to the post office and bank, grocery store and the like. As an older person, I think I pass mostly because we older ladies, dressed conservatively, draw little attention. Bless you for your essay, Carla.
