Where Do You Get the Courage?

For those of you brave enough to go out in public dressed up, where do you get the courage? While dressed, have you ever been surprised to see someone you know (that didn?t know you crossdress)?

Hmmm, I think it?s a process. When I joined this forum, I had never allowed myself to dress completely as a woman until I was in my early 50s. I just assumed I would look ludicrous. Then I saw that many members here looked very presentable, and some quite passable. That was enough for me to try dressing completely. Then makeup. I remember looking in the mirror and a little voice inside said ‘You can do this!”

That moment led me to purchase my first wig, breast forms, and shapeware. After a few days of being fully dressed around the house I suppose my next motivation was a sense of needing to step out into the world, to be free of confinement. I recall that I took my first step out the front to move a sprinkler.

I survived and the genie was out of the bottle. Within days I had made my first trip to the mall, had a makeover at a cosmetics counter, and had coffee and Starbucks. In retrospect, I know I looked like a guy in mediocre makeup and perhaps ill fitting clothes, but I got better and eventually actually felt confident that I would get the benefit of the doubt most of the time.

I recall going to a museum and while there, overhearing a guy ask his wife if “that” (me) was a guy or a girl. I took that as a win!

Its I see it, few start out with courage. We start with a curiosity, a need maybe, that becomes more powerful as we explore and test the waters.

I read all of the successful experience from the girls on this site and read the plethora of advise here. That gave me the courage to do it. I've been out once or twice a week, and have only received one snarky comment (with a Mr. in it). I even recently flew pretty and spent a week in Sedona AZ as Gracie continuously. Every time I hear "ma'am" or "miss" directed at me or someone referring to me as "her" or "she", I still get a thrill. It's such a lovely feeling.
I have seen people that know me that don't know that I crossdress. Since my wife would not like anyone to discover my little secret, I don't look them in the eye, don't panic, possibly divert my path to avoid them. I have not detected any glimmer of recognition or surprise. The one exception is a coffee shop that I frequent. The girl that often waits on me and knows me by name, didn't recognize me the first two times that she waited on me. The third time, as we were chatting, her eyes suddenly went wide and she whispered my male name. We talked a little and, with some astonishment, she said "you're pretty". Politeness or her real impression, I don't know. Nonetheless, I was on cloud nine! Since then, when I walk in dressed as Grace, she calls out "Hi Grace".

In my case it was less about courage but more about loosing all the anxiety and nervousness around leaving the house. I had already told my sister about dressing and she had seen me a few times en femme. I had told another friend that I had dressed a little in the past. One night I was visiting her and I wanted to dress. I phoned her to ask if it would be ok to come dressed. My hands were sweating and I was shaking during the call. She answered "if you want to". From that moment all my anxiety vanished. I dressed fully in a skirt and top and drove to her house. I was totally relaxed, she greeted me at the door acted totally normally and complimented how I looked. From that moment on I had no fear of going out. I have visited my friend almost every week end dressed and accepted an invite to visit a female friend in Eastbourne walked around the town for two days en femme with my friend. I don't really know how this happened but I am glad it did.

Cobbled together from previous posts.

Like many others I started with night time drives. My attire was often a mismatch of items cobbled together, not so much an outfit as scarecrow dressing. While I would find somewhere quiet to park and although I was dressed wig down to heels, leaving the car for a brief walk could be considered as a first outing fully enfemme it’s also a bit like the old question, if a tree falls in a forest and there’s no-one there to hear it, does it make a sound? Similarly by going out and no-one seeing me is it right to class it as a first outing?
Move forward a few years and now I’ve improved my wardrobe such now I have outfits in the true sense of the word it’s still evening time and I’m now walking streets with the odd other person about, usually a dog walker, we pass like ships in the night with me crossing roads to avoid close contact.

I started having a weeks holiday alone spending more and more time dressing as the years went by tentative sorties out in daylight in quiet locations. The one year I discovered a local support group was meeting while I was in the area.

Some years ago I attended a support group. I got chatting to someone who, if I’m honest, looked awful. Dress didn’t fit, cheap wig and it looked it, makeup skills non-existent. Anyway as we talked she said that next day she was going out shopping enfemme, something she did on a regular basis. I asked if she ever encountered any hostility or issues to which she replied no. To give you an idea of what I’m talking about; https://www.youtube.com/watch?v=oVLtJxBqtSA

It was at that very moment I decided if she can I can.

So next day I drove to a shopping park and I can remember sitting with butterflies the size of vultures willing myself to get out of the car. Deep breath, step out, coat on, shake out hair over collar, bag on shoulder, remember to lock car and off to the nearest shop.

Walking in I though any second security will pounce, everyone will stare, folks will laugh but no, none of these. I started to browse still nervous and as the minutes passed, the butterflies landed and I began to feel much calmer.

After about ten minutes I was in my second of what was probably10 or more shops I visited that day. One or two people looked but nothing said, most folks are too busy with their own lives to notice. I found some jewellery I liked so went to the checkout, chatted to the SA, no problems. Be calm, polite, chat about the weather or whatever takes your fancy, they’re human and standing serving can be a bit tedious I would image so something to lighten the day is good for them.

Crowds are your friend. If you’re in a hall with 10 others you’ll notice everyone else. If it’s 100 you’ll likely pick out less than 10. Same shopping, it’s easier to hide in a crowd. Dress like the GG’s your age dress for the time and place you’ll do fine.

Finally my top tip, decide on something you want to look for. A dress, skirt, top, jewellery, doesn’t matter what it is, having something to actually shop for gives you a purpose and stops you looking like a shoplifter and takes your mind off looking around to see who’s looking (no-one).


It's that first step that's the hardest. Accept that you're not going to pass in the true sense of the word but blending in is more than possible. As you gain confidence you relax. that helps you blend, your confidence grows you relax............

I don’t know where the other girls here got their courage, but I got mine from THEM. Reading stories on here of experiences out in the world, made me think why not me???!?

I read about others going out, and asked myself why not me?

Back in 2016 my wife was going out of town for four days, my sons were at college, and I decided it was time to go out. I've written about it in the Pictures section, but here is the short version. Sephora makeover, Nordy's to try on dresses, wig shop to buy a new wig, and two more times to Nordy's. Haven't looked back since. I've been out at least 750 times, as a guess.

Have I run into anyone? How about a kid I coached (for three years) who was the waiter at my table when at a restaurant with a GG friend. If he noticed, there was no tell. I've had a couple of other incidents where I was at places where I knew people, and others who know the boy me know I dress. Nothing negative has happened, and at this point I don't really care.

My philosophy is maybe people see a guy in a dress, but they don't know it's ME in the dress--and I just want to make sure it's a pretty dress. My style has evolved and the people I know like it. One GG friend even borrows my clothes (and she is freakin' gorgeous).

At some point, it's YOLO and if not now, then when?

I hope others read my posts here and at Kandi's and also decide "why not me?"

P.S. I was writing this when the post above hit the forum--so great minds think alike....

Jackie, that Courage, for me, was something inside of me that made it impossible to stay inside my house in hiding. And the big thing is that once that cat is out of the bag, there is almost no going back.

And yes I have run into people that know me in male mode while in Robyn mode. And luckily they did not recognize me. (cross my fingers).

For me personally it is not about finding the courage to be out in public but simply I have no motivation to do so and I am wholly comfortable with Danielle being a stay at home girl. I could be in the minority here and I do respect that for many people being out in public is a validation of their female side and whatever that entails. I think I could muster up the courage to be out and about in public but I cannot think of any compelling reason for myself to do so. Things like having someone address me as " Ma'am" when in my case I know they were just being polite holds no interest for me. I guess what I'm trying to say is if someone is questioning why they don't have the courage to go out maybe it could be they are like me and really don't want to and shouldn't feel guilty about it.

Having said all of that the exception for me would be attending a crossdressers event such Keystone where I could meet and talk to other crossdressers in person.

Totally agree with u, Jackie! Altho, I've been out dressed countless times to bars, clubs, T events, and parties? Those were all with T's I know or am happy to meet. Or, far from home with strangers who have no clue who I am in my drab life!:battingeyelashes:

I have the greatest respect for those T's and CD's who dress out at vanilla venues! First, there's "dressing to blend" which Sherry hates!:thumbsdn:
Then, there's the odd expressions, fish eyes, gaffaws, and random comments which drive me nuts! The worst part, when I'm out shopping, eating lunch, et. it's for a purpose. And, everyone staring at me everywhere I go means I'm the distraction sabotaging the reason I went out in 1st place!:doh:

Those of u that can do this r SO BRAVE!:love:

As with many others, I started at night time. Just going for a walk, or driving somewhere that I knew would have nobody around. I just wanted to get the feeling of being dressed outside before being amongst other people.
Once I'd done that a few times I ventured out early mornings to go for a walk. The only people I would encounter were joggers and dog-walkers and none of them seemed to notice (or care) whether I was a man or a woman.
I have only ever gone out dressed to blend in. If you go out wearing a mini skirt and stilettos, for example, you're going to attract attention.
I went through a phase where I'd drive to an out-of-town supermarket, fully dressed, and then get changed into drab in the back of my car (tinted windows) and do my shopping. Now I just go into the supermarket dressed.
It's really just a case of building up the courage and confidence in little steps.
When you've done it once or twice, you'll never stop.

I agree with you Danielle, I really don't have any strong desire to have public interaction. Between my height, frame, and facial features I really don't think anyone with eyes would look at me other than as a curiosity. Only thing I could think of might be a professional makeup session in a friendly setting as I'm terrible at applying or even choosing makeup.

I wasn't an overnight success. Things we're working towards getting out little by little in very safe spaces, then nine eleven happened. I live right there. I was planning on an event called the girls club happening that weekend. A lot of the city was closed, but not where I was going. After confirming, the party was on, I. Decided, life is too short to wait. I met new friends and old friends and continue to go out in the city for years after that, almost every weekend. I wouldn't say. That's the only push to get me out. The door but that's the one that really got me out there. Public transit and all. It's like the overnight success. Conundrum, it's never overnight, but it seems that way.

Helen, you've hit it right on the money. My heart pounding early adventures were late in the darkness when the only things moving were crickets, cops and crooks.
Then it was voluptuously underdressed in crowded situations. I guess pushing the envelope with self challenge helped the progression to enjoying the titillations of more scandalous or non conforming appearances.
When the eye on the prize became great video to edit down, the public adventures with real life encounters really became exciting. And after doing it for a while, the fond memories remind me of just how exciting my extra special life is compared to the everyday existence.

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I got my courage from the Wizard of Oz. Just kidding. It came from a desire within when I was much younger. It started with a now defunct CD support group. A few night time walks in secluded places such as a canal towpath. A local dress shop that was CD friendly. When browsing dresses on a rack the owner asked me if I would like to try on a dress. I didn?t need asking twice. However I have since regressed, grown older and less confident.

I don't think it takes courage to venture out in public.
I think the desire to be part of society as my feminine self just reached a point where it couldn't be denied any longer. I just wanted to experience life from this side of the aisle and that required doing things I would do otherwise. Once I came out to my wife and she became supportive it was just something I needed to do to be more complete.

In all the years I've been going out I have never encountered someone who was unaware. We used to restrict it to places that were not close to home, but now that's all changed and we go anywhere and everywhere including our town.

Well after dressing at home and fantasizing about wearing womens clothing in public for many years finally in my early fifties I shaved my facial hair and out I went shopping fully dressed head to toe. I do not think courage had anything to do with it for me it was just something I had to do after many outings I became almost addicted to the submissive feeling of being out in public wearing a dress and heels.
For me real courage would be telling my wife about my desire to dress in womens clothes.

For myself, I began going out in my usual drab with pretty undies on. Eventually, that wasn't enough for me and I so very much wanted to go out in a skirt and nice top. I did that once, about 4 years ago, in a crowded park some miles from where I live, and nobody paid me any attention. I haven't done that since, but am still itching to repeat it. Mostly, these days I am wearing womens jeans, work pants, or womens denim shorts in public. I was out at a doctors office this morning wearing womens sneakers, white ankle socks, bikini panties, denim shorts and a unisex teeshirt. I think the teeshirt is actually a womens one because the material is lighter, and the sleeves are shorter than mens stuff. The staff at the office didn't do a double take or anything. I think, for me anyway, I have bought everyday womens wear, like jeans, work pants, shorts and tops that would easily pass as guys clothes. Yes, I still have my skirts, dresses, leggings and nighties for wearing at home.

I bought my first femme clothes at the end of April, just before I joined this forum and I thought I'll be able to go out dressed in October/November after dark from a hotel I'll have to rent a room in.
But when I got my first pumps, I wanted to test them, so I covered my shaved beard (from today's POV very badly) and walked through neighborhood after dark.
I did it three or four times but as the summer was coming the dark meant later and later.
And when I read about other girls' outings here, that gave me a courage to go out, so at the very beginning of July I went to the city shortly after noon fully dressed directly from my apartment.
I enjoyed it, I felt free like never before and when the nervousness disappeared after 10-15 minutes I just felt fabulous. I even bought an ice cream from a stand.
At the end I was out about two hours and not being trained yet my feet were killing me from the heels and cobblestone streets.

And as others said in many ways: with that the cat was out of the bag and I had to go out more.

And yes, once I "met" a friend of mine. It was a beauty expo, he was walking with his wife and we walked the opposite way about 10-15m/30-45ft with direct sight at each other and then passed by each other. He didn't even flinch, because he didn't recognise me and they (him and wife) were just talking, so not even "Is it her or him?" looks.

The first handful of times I went out in public I was nervous but putting some effort into learning female mannerisms, makeup and dressing to blend in paid off in a rapidly increasingly confidence level. I now live full time as a woman.

I didn't begin my CD journey until I was 69 years old. The desire to go out publicly was there from the beginning.That doesn't mean I wasn't nervous about it, but my background as a performing musician helped me a lot. I recognized the feeling was not unlike the feeling of stage fright, and like stage fright you try to turn your apprehension into excitement for the performance at hand. It worked, and continues to work to this day as I go out publicly with some frequency. I wrote about it here if you wish to read about it in detail:

https://kandis-land.com/stepping-out-beating-the-fear/
https://kandis-land.com/stepping-out...ng-the-fear-2/

I present en femme all the time. I don't even remember a time when I was edging into doing so. Even before being on estrogen I had prominent hips and buttocks. Thanks to being on estrogen, I developed a bust. So I don't need any body shaping fillers.
The last time I wore trousers was 2024 late September for my mother's funeral. One thing that's masculine: my voice. I sing second bass in my church choir.
I have never been harrased or threatened for presenting like a woman in dresses.

John

I had to build up the courage over time.

I now go out and dont ever think about it.

I run my regular errands like I would normal.

I guess I am kind of weird because when I think back at the adrenaline rush I used to get, it was always followed with this feeling of relief that I did it and got away with it. Nothing bad happened.

Over time, i realized nothing bad had ever happened , only fun was to be had. It is still fun and exciting, but i will never get that rush back of stepping out the door and into the world. I have become far too comfortable with it. The newness wears off. I will say it was nice to get to a point that my hands did not shake like in the early days.

I have had some really great times going out dressed. I only wish I had done it sooner.

Sandi

Quote:

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Originally Posted by Jillcder

..........for me it was just something I had to do after many outings I became almost addicted to the submissive feeling of being out in public wearing a dress and heels.

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Some of my edited videos get a story line of the situation being a submissive response to a fictitious Mistress who always seems to have a shopping list for me.
So much fun to create a story that becomes more than the adventure was to begin with.

I am a private person and prefer being en femme to relieve stress in my home, accomplishing domestic chores. I know that sounds boring. The idea of mingling with the masses does not appeal to me. I do venture out for evening drives and strolls to satisfy the urge to "just do it!" The times when I went out with the intention of being among fellow humans has been at Halloween.

I think courage comes much more from the desire to be myself than from the absence of fear. At first, I went out to more discreet places, or accompanied by people I trusted, until I felt confident. I still get butterflies in my stomach sometimes, but I've realized that most people are more concerned with their own lives than judging me.

I've met acquaintances once or twice, and I confess it was a shock at the time, but in the end, they acted naturally. I think the key is being at peace with who you are: when we accept ourselves, it becomes easier to face any situation.

Translated from Portuguese by Google.

It occurred when the need to go out dressed was greater than my fear. Once done, it just became easier.

Perhaps some day I will get the courage. To me another component is wanting to pass and not viewed as a guy in a dress. I know some are ok with that and much respect to those girls.

I have no interest in passing, and I doubt it would be possible. That said, I try to push my own boundaries on what a guy can wear in public. I've traveled in leggings many times. I often wear obviously women't t-shirts. All of my tank tops are from the women's side, most are racerback and some are fairly low scoop. And I have many pairs of short yoga shorts. All of these I've worn outside either in public or out front as cars are driving by. Just trying to push the envelope on what's "normal" wear for guys.

It started with blending. Wearing some fem jewelry. Wearing leggings, painting my toes and wearing flips or sandals.

I still get nervous but once I get goibg it settes down.

Hugs,

Jenn

Courage is not the absence of fear but rather the assessment that something else is more important than fear. —Franklin Roosevelt

Courage is being scared to death and saddling up anyway. John Wayne in True Grit

If I am afraid to go en femme to places that ordinary women in my culture routinely go, what am I afraid of? Myself.

I go out every couple of months. Usually it's just for a day/night, but sometimes it's for several days in a row. I pass, more-or-less.

That being said, for me, going out as Sherry isn't a choice: it is something I innately NEED to do. I could choose not to do it -- and I made that choice for a long time -- but it was killing me inside.

OTOH, I'm lucky in several regards: 1. I live in the northeastern US, which is mostly safe; 2. I'm 5-7 and not muscular, so physically passing isn't too hard; 3. I have a supportive spouse -- I didn't always, so going out was harder back then, but it certainly makes it easier now that hiding isn't an issue.

And with THAT all being said, yes, it still takes courage! When I started going out, I was scared beyond belief. Little by little, I learned how to pass, how to be safe, and how to feel comfy doing it. Many years later, that first step out of my home is still a bit nerve-wracking!

To the OP's other question, no, I never ran into anyone I know while out dressed. I had a single close call, but avoided detection.

My courage came with age and of all places, the burlesque community.

For years I was a closeted crossdresser, it was a secret, and it became a habit of keeping it a secret. When I first met my now wife, I decided I needed to be upfront with her, I didn't want to it to be discovered. She could either work with it or not. Now we have been married for 15 years. Just before we got married, she bought me a gift of a series of burlesque dance lessons. I went into these classes knowing I wanted to learn to walk and dance in heels confidently, do an alluring stocking peel, all of the same things the women in class were learning. They were just as nervous about themselves learning to strip as I was. It was a bonding experience, and we formed friendships.

This new group of friends had known from the start; there was no secret to hide. Over the course of 11 years I took more classes, some of the people I met originally formed our own little troupe, I developed a few acts and performed locally. I had two different worlds, those who knew and those old friends who didn't.

At some point, having experienced so much acceptance within the burlesque community, I came to the conclusion that I kept it a secret not because I didn't want others to know, but it had become a habit. There was no real reason I shouldn't be able to tell everyone. This may not be the same for everyone, but I truly didn't fear losing friendships over my being a crossdresser. One day I just bit the bullet and told five of my male friends as we were up at my friends' cabin. No one got angry, no one treated me differently, it was just out there. I have since told multiple other friends.

The timing of this specific thread is pretty fortuitous. One of my burlesque friends is producing a show in three weeks and asked me to come out of semi-retirement to perform an old act. None of my old friends, who I had been keeping my secret crossdressing from, have ever seen me perform. Now that they know, I have 14 old friends who are showing up to see me perform for the first time.

It's not a secret anymore.