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Thread: Any advice for going out dressed for the first time?

  1. #1
    New Member
    Join Date
    Mar 2018
    Atlanta, Ga

    Any advice for going out dressed for the first time?

    Hello there,

    I am brand new to dressing. I have always loved the look and feel of women's clothes and decided to finally let my female self out and I love it.
    I have decided to get a makeover and go out. I have been wearing panties and hose under my man clothes regularly and just have an uncontrollable urge to put on makeup and a dress to go with it and be out like that!! I am not looking to be a full time femme, just go out in occasion and have some fun.

    I am excited beyond belief to think about it and scared to death at the same time. I would love to hear any advice or stories about your first time in public dressed.

    Thanks for sharing,

  2. #2
    Member sami1952's Avatar
    Join Date
    Feb 2006
    I remember my first time out by my self, I was scare to death but once I got out of my car and started waking towards the club, I felt more at ease. after the first time it was easier for me to go out. take that first step, you won't regretted.
    janielatb: I'm in love with the person inside me.

  3. #3
    Miss Judy Judy-Somthing's Avatar
    Join Date
    Dec 2015
    Just don't go out alone late at night.
    I was chased once and harassed twice by men in cars trying to pick me up!
    One guy in a car circled around the block and came back looking for me so I hid under a car, (in my favorite dress) until he was gone!
    "This is ME" I am not CRAZY, I'm just a GUY who likes dresses!
    Since allot of men dress up in woman's clothing that makes it a manly thing to do!
    Much more fun than fishing.
    I do construction like house building and I love CD-ing, what's the difference?

  4. #4
    Stop that, it's silly.... DIANEF's Avatar
    Join Date
    Aug 2016
    The first time is scary (certainly was for me), but you soon realise all fears are in your head. If you present well almost no one looks at you, they are too busy doing their own thing. I would advise going some where moderately busy rather than quiet, where you won't stand out, and definitely not late at night in some isolated area. A little self confidence certainly goes a long way, and once you get going it gets easier and easier. Good luck!
    Here today, gone tomorrow....

  5. #5
    Platinum Member kimdl93's Avatar
    Join Date
    Jan 2010
    Almost the Great White North...
    My suggestion was to go during the day time, to avoid the things Judy mentioned, and go fairly casual. Nothing draws attention more than being overdressed.

    Easy come, easy go;
    Easy left me long ago...

  6. #6
    Carole carhill2mn's Avatar
    Join Date
    Oct 2007
    Twin Cities, MN
    Going out in public the first time is both scary and exciting! It is wise to do some pre-planning. There are many things to consider. Where is a safe place to go? Dress appropriately for the time and place. You probably should not wear high-heels. Do try to blend with your surroundings. If you are having a make-over first be sure that it is not over stated (ie, too much). Do not try to sneak around. Act as if you belong. If someone looks at you, a quick little smile is a great way to react.

    How you walk is a big thing. Take smaller steps. Do not plod like you are in a field. Be aware of your hands and arms. Try to emulate the movements of the women that you admire. Most women do not make grand gestures. Learning to speak "womanly" is a whole different matter and will take practice, practice, practice.

    Good luck and enjoy!
    Hugs, Carole

  7. #7
    Aspiring Member TheHiddenMe's Avatar
    Join Date
    May 2016
    Metro East area near St. Louis, Missouri
    I wrote (warning: at length) about my first time out locally.

    That was about 18 months ago. Since then, I've been out at least 40 times, including three times in the last week (and have another outing planned for tomorrow morning and evening). Go for it.

  8. #8
    Silver Member Micki_Finn's Avatar
    Join Date
    Aug 2016
    Southern California
    Definitely definitely dress for the occasion/location. Practice walking in the shoes you’re going to wear. Wearing heels in the house is very different than in the real world. Other than that, elbows in, chin up, chest out, ankles together, and don’t look scared. Just have a good time

  9. #9
    Yeah Ok like whatever Tracii G's Avatar
    Join Date
    Aug 2008
    Between here and there but mostly here close to the donuts.
    It all depends lets hear your ideas for your first time out and go from there.
    What you plan to do and where you plan to go that kind of thing.
    I would love to hear what you think you should wear too.
    By asking these questions we will get a better idea of what you expect.
    Might seem odd me asking these questions of you but trust me there is a reason I ask.
    Head Executive Chief of the Dept of Redundancy Dept.
    Expert plumpologist

  10. #10
    Junior Member Jenny123's Avatar
    Join Date
    Nov 2015
    Morgantown, West Virginia
    First, it's really exciting to go out in public. You will be nervous the first time. However, it's a step that I am so glad that I did. My biggest piece of advice is to try to act as "normal" as possible. For example, the first trans woman I ever saw in public was when the two of us were in an elevator together. I started to pay attention to her not because of how she looked or what she wore. Instead she faced the side wall of the elevator which is what caught my attention.

    The other issue to consider is safety as others have said. Before I started to go out in public, I spoke with a good female friend and got her input about this issue. One thing that has surprised me is the amount of thought I put into safety issues when I go out as a woman which I never do when out as a male.

  11. #11
    Join Date
    Nov 2005
    Make sure to pee before you leave the house. Or you'll come back to the forum writing posts about bathroom use.

    As others said, be careful as any woman would do when going out.
    Hiding in my room, safe within my womb.
    I touch no one and no one touches me.-S&G

  12. #12
    Silver Member Becky Blue's Avatar
    Join Date
    Oct 2005
    My advice is go with someone, not only is it safer but also much more fun!!!
    For me going out is the ultimate and I could not recommend it more highly
    A.K.A Rebecca & Bec

  13. #13
    Senior Member faltenrock's Avatar
    Join Date
    May 2007
    You might look at my started threads, I've been going out for years. I also recommend to look at youtube videos to see what works on people and what doesn't. I'll answer any particular questions if you like.

  14. #14
    Stand-up Comedian En Fem❤ Alice_2014_B's Avatar
    Join Date
    Jan 2014
    Puyallup, WA (USA)
    Confidence is key.
    First time is pretty much the toughest, but it gets easier after that.
    Feel free to PM me; like many others here, I've been out in public quite a bit.
    Melissa: "... and why are you dressed as a woman?"
    Coach McGuirk: "Because it's freeing."

    -Home Movies
    (cartoon series)

    Shoe size: 9 US women's.
    Dress size: M to L; 8-10.
    Height: 5' 6".

  15. #15
    Just do it already! DaisyLawrence's Avatar
    Join Date
    Nov 2017
    Fantasy Island
    Dress casual, nothing sexy and be confident. It all depends on how you present, if you 'pass' then you need no advise as you will be just another woman in the publics mind, if not then the tips in these replies will help.

  16. #16
    Member Drew GB's Avatar
    Join Date
    Jan 2018
    Ashland Or.
    Breathe! That’s it. Just breathe.

    This is a guilty pleasure of a movie for me. But at the very end of this clip is one of the funnier running gags that proves my point.

    You will find that most of the truths we cling to in life depend greatly on our own point of view.
    (Sir Alec Guinness as Obiwon Kanobi in Star Wars Return of the Jedi)

  17. #17
    Gold Member Helen_Highwater's Avatar
    Join Date
    Jan 2010
    Midlands UK
    A little planning goes a long way. I pays to have a plan, and a backup. Know the area you're going to. That way you won't wonder into an area you wouldn't go armed to the teeth and with backup even in drab.

    It's counter intuitive but daylight is your friend. Walking around a shopping mall as Diane says allows you to hide in a crowd.

    Ask yourself this. Do you really pay that much attention to other shoppers when out in drab. Your radar may pick up of that GG in the killer heels, short skirt and low cut top but apart from that most people don't really register. So as others have said, dress to blend. Emulate what GG's of your age are wearing, just tone down the sexy.

    I don't pass. Few really do. However I've learned to walk like a female, carry a bag, hold my arms and generally behave like a female. I'll say it again, if it walks like a duck, quacks like a duck, and looks like a duck then people see a duck. That's what you're aiming for. I've walked down busy streets and while I can't claim to be invisible, many more ignore me than look and by my acting with confidence those that look just get on with their lives.

    When you have your makeover ask the makeup artist to do your makeup for a GG just going out shopping and not for that big night out. Remember, blend.

    Don't, IMHO, go with too big a chest. Again it draws the eye. Also if you see something in a shop you really like and your confidence is good enough to allow you to try it on, a C cup is likely to make it fit better.

    Low or flat heels! If it goes well, and there's no reason it shouldn't, you'll be spending hours walking around. High heels will quickly take their toll on you feet and legs and could spoil the party.

    Don't be afraid to interact with the SA's. 99% will treat you wonderfully, ignor the 1%. If I'm out for a day's shopping I always stop for a drink and a cake in a dept store cafe or similar. Can't tell you how many lovely conversations I've had.

    Lastly, back to the plan. Give consideration as others have said, to what you'll do should the call of nature happen. If your confidence won't take you into the ladies often smaller coffee shops/cafes have dual sex toilets.

    Good luck, it's an addictive thing you're about to embark upon.

  18. #18
    Platinum Member Beverley Sims's Avatar
    Join Date
    Nov 2011
    Lowestoft UK. Beverley was here.
    A blouse and pants of some type with a wig and a little makeup.

    Stick to blending in until you get the feel of your surroundings and a lot of practice in presentation.

    The skirted or dress look can come later.
    Work on your elegance,
    and beauty will follow.

  19. #19
    Gold Member alwayshave's Avatar
    Join Date
    Dec 2011
    Washington, DC
    Flats, not heels. Easier walking or walking quickly if need be.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  20. #20
    There's that smile! CarlaWestin's Avatar
    Join Date
    Jan 2011
    Area 51
    First time out? All of the advice so far is good. I prefer to dress a little more sexy when I'm out because my opportunities are limited. I tend to choose places that aren't particularly congested. I also usually avoid places with cattle chute exits or security guards. But, if I'm dressed more blendy, I don't care where I am. Also, you might want to watch the way that women walk and then compare to yourself. Men have a natural ape walk and swing their arms. It's been mentioned here that you always worry too much about what people are thinking about you until you realize that nobody really cares. Maybe just a drive around. I've done that in every outfit you could imagine.

    Capture.JPG Capture3.JPG
    Last edited by CarlaWestin; 03-09-2018 at 08:22 AM.
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  21. #21
    Reality Check Krisi's Avatar
    Join Date
    Feb 2014
    If you expect to be taken for a woman you will need much more than makeup and a dress. A wig of course unless your natural hair is long enough to be styled as women's hair. Boobs. Not too big but women typically have noticeable breasts. Hips and butt. This is something a lot of crossdressers forget but if you look at women, they usually have much wider hips and more protruding butts than men.

    Of course there are other things. A woman in public will carry a purse. She will usually be wearing jewelry including earrings, necklace and bracelets.

    Others have already mentioned this but if you want to fit in, don't go out wearing six inch heels, a miniskirt and heavy makeup. I suggest going out as a guy and taking notes on what women are wearing first. You should dress like they do.

    My last bit of advice is to practice "being" a woman at home before you go out. Put on your wig, boobs and butt. Get used to the feeling.

    Best of luck.

  22. #22
    Senior Member rachael.davis's Avatar
    Join Date
    Aug 2008
    1. From by bestie GG - You can put your bag down, and look away in any place you'd feel comfy taking off your blouse and bra, failing that keep it on you, and be aware of who is next to you.
    2. Worse to worse - if you're wearing slacks put a spare car key, and a 20 in one of the pockets, just in case.
    3. From my therapist - you're exiting a world of "male privledge" you've lived in all your life, and you're not going to be extended the standard "feminine courtesies" Pay a lot of attention to your intuition, and if a place feels wrong have your feet help your body.
    4. kind of surprised no one else put this down, but put a "bug out bag" with makeup remover, ambiguous to male sneakers and sweatshirt in your car trunk, in case of car trouble or an accident.

  23. #23
    Member leannejacobs's Avatar
    Join Date
    Nov 2014
    I'd recommend videoing yourself walking until you can walk like a lady, there's nothing worse than a bow legged CDer stomping along, it's a dead give away, if your unsure what to do with your hands/arms, fold them, I see lots of women walk like this. If you look half way presentable no one will pay you the slightest bit of attention, nobody really cares what's going on outside their bubble.
    Now the big bit of advice, be aware, once you start this, it will consume you, you'll want more and more until it's all you think about, it's such a buz, I'm very very tall which is my biggest issue but even I can have a good walk about without any issues, avoid teens, they will clock you, ignore any comments and carry on your way.

  24. #24
    Silver Member CynthiaD's Avatar
    Join Date
    Jul 2011
    Go out in broad daylight where there are plenty of other people. Walk and act like you're totally proud of the way you look. Act like you have a perfect right to be where you are, looking the way you do. Don't try to explain anything or make any excuses, either to yourself or to anyone else. If anyone acts rude, look down your nose at them, give them the old head-shake, and walk away proud.

  25. #25
    Platinum Member
    Join Date
    Oct 2010
    Western Washington
    If you're scared to death I recommend taking 'baby steps.' What do you wish to accomplish? Where do you want to go? My first forays outside the home full en femme and not confined to a car were on Halloween. That gave me an 'excuse' and made me feel comfortable walking into stores; Winchell's Doughnut House, Safeway, etc. I do not have the inclination to do that any other time of the year. To me it has to be more than just "I did it!" moment. I rather take a walk in the early evening in a nice safe residential area that has a small stores. I do not head off to dark closed parks after dusk.

    Here's my routine. I park my car in a Safeway parking lot. I really like it when there is a gently falling rain which justifies using an umbrella to obscure my obvious masculine face if I encounter someone walking towards me. I forego the heels. I bought a pair of shoes which I consider a flat; one inch rise at the heel and deadening man made material on the heel and sole. When I did wear a 3 1/2 inch narrow heel the clicking noise in the evening cool air was a head turner. I did not need that at all. It is within my comfort zone to satisfy my urges. If you just want to test the waters of being outside a car fabricate a reason to exit the car; mail a letter at a blue box, get a free newspaper out of a box, return a library book, buy a soda from a vending machine. I love the cool breeze caressing my legs and playing with the skirt of my dress and slip underneath.

    For just strolling I've recommended before to buy a pair of women's athletic shoes and accentuate with brightly colored laces. In my area many professional women who wear high heels at work will commute in athletic shoes and carry their heels in a tote. If you have fear or need to escape a potential bad situation athletic shoes help. I would recommend a clear plastic tote so any passing people will make that visual connection and reasoning for the athletic shoes.

    You can always start small and work up to bigger adventures rather than start big and have a bad experience in a store or mall.

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