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Thread: How to find the courage?

  1. #1
    Junior Member
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    Jan 2016

    How to find the courage?

    I see and read all these stories about you girls going out as yourselves and I dream of that!! The most I have done is a short drive, never on a busy road either! How did you get the nerve to be out dressed? I need some ways to empower me!


  2. #2
    Gold Member Helen_Highwater's Avatar
    Join Date
    Jan 2010
    Midlands UK

    Most start as you have with going out in the car, usually at night. Personally I developed that by stopping somewhere quiet and initially, and I remember just how scary this was at the time, getting out and simply walking around the car. Sounds silly now but at the time it was a huge step.

    That developed to walking away from the car. Over time the distances increased then one night it turned into a walk around the block. My presentation wasn't that great back then, wardrobe was awful but I did it.

    First real human contact, a drive through Mac. I don't think the young lad behind the glass looked at me once. He could have been serving ET for all the notice he took of me.

    Wardrobe got better, walks turned into evening window shopping once the stores had closed and fewer folks around.

    I won't bore you with the details but eventually I got up the courage to go into a shop. What you learn from that experience is that, like the lad in the drive through, most people don't pay that much attention. Unless you're makeup makes you look like the Joker or you're dressed like a hooker folks generally don't care.

    Forget passing. Very few do, certainly I don't but in all the hours I've spent out and about, the worst thing that's happened to me is someone saying, "Thanks MATE" after I'd paid for petrol.

    I'm sure others will echo this. Dress to blend, going somewhere with lots of people is safer than a walk around a street late at night. At a busy mall you're just a face in the crowd. You can hide in plain site.

    The first time is the hardest but even after a few minutes in a shop your nerves will quiet down and soon you'll be an old hand at it.

  3. #3
    Aspiring Member Heather76's Avatar
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    Jan 2022
    Coastal SC
    Thank you, Helen, for that information. My 1st time "out" I was in male mode but with a bralette and DD forms under my golf shirt. I stopped to pump gas in my car. I now often drive around similarly adorned but always remove the forms before going inside a store/business. I'd love to drive to a park dressed, get out, and walk around; but, that will have to wait until an evening my wife is out of town.
    It's never too late to enjoy a happy childhood.
    Live each day as though it's your last 'cause one day you'll be right.
    I'm finding the more feminine side of me...and I ❤️ this adventure.

  4. #4
    Miss Conception Karren Hutton's Avatar
    Join Date
    Aug 2005
    South Western PA
    Olivia, my first time out I was 16 and dressed in my mothers clothing. Snuck out of the house and took a walk around the block late at night. The feeling of excitement and being scared to death was amazing! Decades later when I started dressing g again and had mastered makeup I again attempted to go out. It was at a hotel in Price Utah. Must have give to the door and checkered out a dozen time. Finally I just flung the door open and walked out and down the hallway. Passed two guys on the way out. Nearly fainted before I got to the car to take a drive. Then just expanded from there. Every outing pushing the envelope more and more. It is like addicting!

    So next time add something extra to your outing . You will have a blast! Trust me!
    Last edited by Karren Hutton; 05-14-2022 at 06:17 AM.

  5. #5
    Platinum Member kimdl93's Avatar
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    Jan 2010
    Going to seed!
    I was a late bloomer as far as getting out of the house is concerned, but then I never allowed myself to dress completely until I was in my early 50s. Once I did, that long feared switch clicked, and I realized I could do this. In short succession I went from daily underdressing, to full en femme to the first step out my front door in broad daylight.

    Looking back on those heady days I realize that at some point my need to get out simply overpowered my fears. Perhaps that is what we sometimes mistake for courage

  6. #6
    Aspiring Member MonicaPVD's Avatar
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    Jul 2018
    New England
    Olivia, Helen offers good advice. I would add driving to a town that's far enough away to calm your fears about encountering a neighbor, then stopping at a gas station to pump a few dollars of gas (just a minute or two). On your next trip, go into the station and buy a pack of gum or a beverage. That sort of gradual confidence building is key.

    There are two fears working against us when we start to go out dressed. First, fear of not passing as a woman. Second, fear of being recognized by someone who knows us.

    You can discard the fear of not passing right away. You won't pass. Period. I have been going out for years, arguably look great as Monica, and still would not be mistaken for a cis woman by the majority of people I interact with. But, guess what? It doesn't matter because people don't care. They really don't. They only care about themselves.

    The fear of being recognized is a whole other thing. I recommend that you manage that fear by beginning to go out to places that are not near your usual stomping grounds. For example, I used to go to cities or towns that were 20-40 minutes away. The chances of encountering a relative, neighbor, or friend who might recognize my car, and wonder why some awkward looking woman was driving it, were almost nonexistent.

  7. #7
    Platinum Member alwayshave's Avatar
    Join Date
    Dec 2011
    Washington, DC
    Olivia, my first time was to a meeting of other crossdressers. It was at a hotel and I got dressed there. The walk and elevator ride from my room to the conference room was terrifying, but I did not turn back. Being with other crossdressers was liberating. Having done it once, future outings just became easier.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  8. #8
    Senior Member Jean 103's Avatar
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    May 2013
    Central Coast, CA
    I was terrified at first. I had to force myself, telling myself you can do this, just fake it.

    Now I live as Jean , have absolutely no fear. I'm the same person the difference is experience.

    Just remember you are a woman. Act like one, go and do things a single woman would do. Things you already do.

  9. #9
    Member AllieBellema's Avatar
    Join Date
    Jan 2015
    NE Indiana
    Sometimes the event can help out too. My first time out was actually during a Pride fest. After getting encouraged by a friend, I went ahead and dressed up in one of my full length southern belle gowns and I was nervous at first, but I took a deep breath and dived right in. I had alot of good reactions from others when they saw me and it kept me going for a few hours. Once I was there, it was on and the nerves went away.

  10. #10
    Silver Member Maria 60's Avatar
    Join Date
    Sep 2010
    I also started with short night drives dressed from the waist down and when joining this community my confidence jumped up. The drives became longer and I started stepping out of the car. I knew I was in the right place here because on my first outings I told everyone I was walking in a quiet commercial area and a overwhelming response about the dangers of walking in a quite areas. I then started to complete my look with dressing full when driving and I remember the first time how hard and strange it felt to put on a wig when I went for a drive. I started putting in gas in the car and my biggest step was when I called a crosssdressing store in the city and the owner had mentioned to me if I wanted to go there dressed it would be ok. I took a deep breath and walked on the street and in the store in daylight and the owner pumped my up with confidence to go have a coffee with her in a coffee shop which that day was probably the most amazing day ever. I believe without the help and support of my wife and this community I don't believe I could or would have been so complete and confidence to do what I did.
    Not as much now but at one point my confidence level was so high that I got caught in a police spot check and I was so calm and confident that when the police officer approached my window I told him that I'm a crossdresser, first time in my life I said that.
    The problem is in life it's human nature to always want more and take bigger steps, my problem is I don't in any way pass that is limited me but I'm still making small strides and believe with small steps you will also

  11. #11
    Member Fiona_44's Avatar
    Join Date
    Jan 2022

    There are a number of things you can do to help ease the fear.

    - Read through the many stories here about how gals prepared for their initial trips outside. That is what ultimately gave me the confidence to go out for the first time two weeks ago.
    - Your ultimate goal is to blend in as much as possible. Wearing a short skin-tight dress with 44DDDD boobs is okay in the house but not outside. Think leggings, jeans or a reasonable denim skirt.
    - I skipped the going out at night part and went out during the day. Used only lipstick and wore women’s sunglasses to hide my non-made up eyes. If you don’t want to bother with a wig get a women’s scarf or kerchief to cover your head.
    - Go somewhere like a large park where there are a limited number of people.
    - Learn how women walk & sit vs. how men do it and learn how women hold their arms when walking.
    - As many others have already said, you will never pass fully. The objective is to blend in and stay inconspicuous.

    If you need advice just ask. There are a lot of very helpful gals here.

    Last edited by Fiona_44; 05-14-2022 at 09:58 AM.

  12. #12
    Female Illusionist! docrobbysherry's Avatar
    Join Date
    Sep 2007
    Orange County, Calif.
    Olivia, I remember all the times I was dressed to the 9's in my hotel rooms. Terrified to leave my room. I told myself I had to open the door, walk down long hall ways of other rooms filled with vanillas. Then, get on an elevator with other folks.
    Then, walk thru casinos crowded with Muggles before finally meeting up with my T girl friends!

    Opening that door and walking out was and is always the hardest dam thing to do!

    I end up taking a deep breathe with my heart racing and just DO IT!

    Nothing very bad has ever happened to me the countless times I've gone out that door. But, the amazing girls I've met and the exciting experiences I've had dressed has changed me and my life forever! I can't imagine my life without Sherry now. And, that "going out the door" anxiety is just part of the thrill!

    Just DO IT!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  13. #13
    Platinum Member
    Join Date
    Oct 2010
    Western Washington
    Olivia, I was terrified the first time out of the house, and, I did nothing more than drive around my immediate neighborhood. I still stay off I-5 as I do not want to get a flat tire, caught between exits. I stay within my personal comfort zone. Being six foot and 200 pounds (size XL, 18-20) I do not want to become an attraction at the local mall. I am content with my evening strolls through a quiet residential neighborhood within my small city. I created a reason to get out of my car. I dropped off library books at the night return slot. At one particular library branch I parked my car across a wide busy street so I had to wait for all cars to pass. It forced me to walk farther. I also stopped to retrieve one of those free newspapers from boxes all over town. Dropped off mail (actually return reply inserts, unfilled) at those blue USPS boxes all over town. I enjoy the evenings cool air playing with my dress and slip, no pants ever for me! The area for my strolling has two grocery stores. I carry a tote with the logo of one of the stores as if I am a woman returning from shopping. It's not adventurous; just walking around the blocks and maybe window shopping. I found, from a psychological viewpoint, the best time for a prolong stroll is during a light rain. The big black umbrella I use doe a lot of mask my height and bulk to some degree, and, obscure my very masculine face.

    This is within my comfort zone. Many will tell you to find a support group. Decades ago my wife gave me the green light to do that. I looked, none to be found. Needs and expectations change, and, I found as I aged, the psychological need to mingle among the masses has waned. The only times I have engaged with fellow humans has been on Halloween. Getting dolled up en femme really is not fooling anyone, but myself. Not being a party goer, Halloween adventures were shopping for party goods at grocery stores. It was minimal interaction, even less now with self checkout, but, it did put me out there. Sometimes it is small baby steps, but, it never leads to a full gallop.

  14. #14
    New Member
    Join Date
    May 2022
    Quote Originally Posted by Stephanie47 View Post
    I stay within my personal comfort zone. Being six foot and 200 pounds (size XL, 18-20) I do not want to become an attraction at the local mall. I am content with my evening strolls through a quiet residential neighborhood within my small city. I created a reason to get out of my car.
    This is my practice as well. I almost exclusively stay inside, but have had times where I wanted to put a nie pair of breasts on and go for a walk. Usually late evening, local quiet park or walking trail somewhere. Not early enough so I'm a center of attention, but not late enough to where I become a weirdo walking around at night.
    Maybe a drive here or there. That's about it.

  15. #15
    Silver Member Bobbi46's Avatar
    Join Date
    May 2015
    France, Villessot near St Christophe
    Courage comes with time, at first i was as nervous as nervous can be, It all comes down telling oneself "I can do it " and out you go. but take small steps,go to safe places and above all else DON't dress to be looked at. Many of us say "dress to blend", wise words because if you are dressed in what to woean is "everyday wear" you will be fine.
    After your first "proper" time out where everything was just fine you will feel better in yourself and the next time will be easier than the first and so forth.
    Go for it girl you can do it!!!
    I started life a lost man now I am a found woman

  16. #16
    Join Date
    Dec 2015
    Don't go out late at night, or walk round supposedly "safe" places in the dark.

    Instead, visit crowded places where everybody is busy with their own affairs. It's a lot safer and actually nobody cares what you look like.

    I have developed my confidence by local supermarket visits. Everybody pushing trollies is on autopilot. I started wearing a bra under a loose top, but now I carry my bust and bra straps fairly openly under quite feminine tops. I wear modest lip gloss and heeled sandals.

    In fact I would claim that I present myself better than many of the women shoppers!

  17. #17
    Claire M Claire M's Avatar
    Join Date
    Jan 2014
    The 1st time I went out fully dressed I went to a mall early in the day when traffic was light. I did fine until I ran into a small group of high school girls who pointed and got a good laugh. I made a quick retreat to my car. In the moment I was horrified but when I was safely back in my car I realized there was really no harm done.

    Two things:
    The hardest part of stepping out is opening the door and taking the first step. Take a deep breathe, relax and go for it. Don't feel bad if after the deep breathe you turn around and close the door. It happens sometimes, even 20 years after my first outing.

    Remember, if you are wearing women's clothing, makeup and a wig you look very different. The majority of people are too busy going about thier own lives to notice you. Someone may spot a man in a dress but its unlikely someone will spot YOU in a dress.

  18. #18
    Member Julia1984's Avatar
    Join Date
    Dec 2015
    East of England
    The first time I left the house as me I had arranged to go to a local wig supplier.

    I'm not sure how "good" I looked (and looking back at the obligatory photos, I suspect the answer was "not very"!)

    The point is that having a trusted, trans-friendly place as a destination made it all so much more achievable and less easy to chicken out.

    It helped that I'd been in touch with the seller before the visit and that she had put me fully at ease before the day.

    So. Plan; prepare; do. That's about it. The walk from the front door to my car was still one of the most exhilarating moments of my life.

    Go for it. You will thank yourself the day after you do.

  19. #19
    Member TAG's Avatar
    Join Date
    Mar 2022
    I would suggest using common sense and not go to a park at midnight dressed like a hooker.
    Go out during the day for a drive, go thru a drive thru and get a coffee or a soft drink something like that.
    I don't know if it would be called courage more getting over your fears.
    I will say once you do go out as your female self you will wonder what took you so long.

  20. #20
    Join Date
    Mar 2022
    Well, one option is just go for it! Don?t hesitate and if it feels right do it! I?ve been out twice, and decided at my age and my late start, o didn?t have any time to spare?.have a nice story but thinking not for this thread.

    Enjoy, hope it goes well!


  21. #21
    Silver Member Sometimes Steffi's Avatar
    Join Date
    Sep 2008
    Nation's Capital
    The first time I went out dressed, I met up with a girl from here an we went out to lunch at the local LGBT bar and restaurant. Then, she introduced me to two friends and they introduced me to two friends and there was always a few who wanted to go out on a Saturday night.

    Around the same time, I went to the Maryland Renaissance Festival and rented a wench costume. Most people didn't even give me a second glance. Those that did were usually GGs who clocked me. They usually gave me a big thumbs up or even a bigger smile. I just gave them a big smile back, because I knew that I wasn't really fooling anyone who was paying attention.

    I skipped the whole driving around in the car thing and just jumped to the second level.
    Last edited by Sometimes Steffi; 06-01-2022 at 10:57 PM.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  22. #22
    Heisthebride Heisthebride's Avatar
    Join Date
    Jun 2010
    It only took me thirty years of baby steps along the way; I hope it doesn’t take you as nearly as long to realize it’s not as hard as it seems. My advice probably goes against what other people might be saying about short drives or walks at night. That is absolutely an option and you should only do what you are comfortable doing, but I took all of those same little risks and it very slowly helped me to build up courage. But now at age 55 I am finally in the “I just don’t care what other people think” phase of my life. If you can jump to there, things will be so much easier.

    1. Be aware of your location. Big cities are typically more liberal, than rural areas. Gay bars, drag shows, burlesque shows, should be safer than a townie bar or biker bar. Use common sense when deciding where to go.

    2. Dress for the venue. You can dress like Little Red Riding Hood at a Halloween party, probably not at the grocery store. If you’re at a drag show, feel free to glam it up a little. But don’t feel like you can’t go to Target or the grocery store too, a cute top and skirt combo is perfectly fine.

    3. You will likely be clocked, but so what. I’m 6’4” before I put on heels, I know I don’t pass and I accept that. You have every right to wear a dress or skirt or heels if you want to. Sometimes I’ll be in male mode, no makeup, no forms or bra under my tee shirt and in a skirt. Other times I’ll be in a formal dress, long red nails and full makeup and to dinner at a nice steak place. It’s all good.

    4. Take a deep breath and just do it. I still get a little nervous. Last October I flew en femme for the first time, airport security, passing hundreds of people in the airport terminal, sitting on the plane. Every time I go out dressed I am more convinced that nobody really cares. Even if somebody does care they likely won’t even interact with you. So what if they talk about you, I think about or talk about other people I see on the street sometimes. Most of the time I rarely even notice people I pass, and they rarely notice me, even if I am dressed as a female.

    My best advice is just try it. Doesn’t matter where or when or for how long. Rip off that bandaid and you’ll discover it really wasn’t so tough, and it gets easier every time.
    Rebecca Bas

  23. #23
    Life is more fun in heels Genifer Teal's Avatar
    Join Date
    May 2005
    Don't feel discouraged. You are taking a big step outside your comfort zone. That's often where the magic happens. Many times I've had a helping hand or some circumstance which gave me the needed push to explore further. My big start was 911. There was an event in nyc 9/15/2001. I wasn't sure about going. Then 911 happened. We all mourned for a few days. When Saturday came around, the city was closed below 20th Street. The party was on 22nd street and was still happening. I went and never looked back. Spent the next several years out almost every weekend in the city. Somtime's you just need the right push to get you where you need to be.

  24. #24
    Exploring NEPA now Cheryl T's Avatar
    Join Date
    Feb 2006
    I simply decided I didn't care what others think anymore and that it was time for me to be part of the world as the woman I am.
    I don't wear women's clothes, I wear MY clothes !

  25. #25
    Senior Member Sandi Beech's Avatar
    Join Date
    Nov 2019
    Southeast US
    You know , I do not know where the courage comes from, but sometimes you just have to do it.

    My first picture post called ?Maybe I?m Crazy? has a picture where I was wearing nothing but black lingerie to a gay bar back in 2017, and as difficult as that was at the time, it only gets easier. That was the second night I ever went dressed into a bar. I had a picture of the first night but was accidentally deleted. It is just one of those things that if you need to do it, you will find a way. It is easier to do than you would think though.


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