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Thread: Mistakes and lessons learned first time out

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    Mistakes and lessons learned first time out

    Hello all,

    I'm planning to out soon for the first time and be around other people. I'm excited, but as it approaches I'm realizing more and more items I might need that I hadn't considered or needed before for private dressing, for example, a purse to hold my wallet and phone.

    Does anyone have experienced or lessons learned that they wish they knew before they headed out into the world? Many thanks!

  2. #2
    its important mykell's Avatar
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    im not the most experienced with this but i would say relax and have fun and know all will not go as planned but its good to have a starting reference point.
    plus a real purse is a necessity, i started with a free carryall from a makeup purchase, could never find anything in it. spent more on it than i should have but i have to keep my makeup somewhere.

    remember have fun, i like to chew gum when i get nervous, gets my mind occupied by chewing so bring some in your purse, it may come in handy....
    Last edited by mykell; 03-25-2016 at 09:30 AM.
    ....Mykell
    i dressed like a girl and i liked it! crossdressing...theirs an app for that

  3. #3
    Aspiring Member josie_S's Avatar
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    This might seem weird but make sure your car is working properly! Check tail lights (I got pulled over for a busted tail light once), but more important is to keep make up remover and a change of clothes in your car in case you get a flat or need help--I can't imagine how uncomfortable it might be to change a tire in heels or worse, how vulnerable one might suddenly feel by the side of a road. It's not sexy advice, but I've found it to be a nice peace of mind

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    Member Natasha V's Avatar
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    Wow thanks I hadn't really thought of that. Change of clothes definitely would come in handy.

  5. #5
    Lisa Allisa's Avatar
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    Wow ,where to start, depending on where your going and what you will be doing it's hard to list things. First and foremost, SMILE and keep your head up and eyes forward, it can be very nerve racking but your doing nothing wrong and relax and go with the flow. Oh yeah tissues I never have enough tissues when I need them. Good luck we're all behind you, and enjoy.
    "you are a strange species and there are many out there;shall I tell you what I find beautiful about you ,you are at your best when things are at their worst" ...[ Starman]
    It may of course be a bit disturbing to sense that one is really not so firmly anchored to the gender one was born into.

  6. #6
    Girl from the Eagles Nest reb.femme's Avatar
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    Take plenty of cash, especially if you bump into me in a bar.

    A girl on YouTube said that she always took a full makeup set with her for repairs during the night. She took the works but I always make sure I have a little bag with red and orange lippy (also acts as beard cover), one colour eyeshadow, blusher, concealer, pressed powder and a couple of makeup pads. Plus a soft brush, medium sized for general makeup application.

    I like to carry a mid sized handbag (purse) with my driving licence, travel card and debit card.

    Other than that, I always make sure to have my best socialising head on before stepping out of the door.

    Becky
    Flying high under the spell of life!

    http://www.rebsweb.co.uk

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    Quote Originally Posted by josie_S View Post
    This might seem weird but make sure your car is working properly! Check tail lights (I got pulled over for a busted tail light once), but more important is to keep make up remover and a change of clothes in your car in case you get a flat or need help--I can't imagine how uncomfortable it might be to change a tire in heels or worse, how vulnerable one might suddenly feel by the side of a road. It's not sexy advice, but I've found it to be a nice peace of mind
    Josie - Your suggestion is a good one. I experienced a flat tire and had to change it in a gravel parking lot in the middle of the day. I was wearing a short skirt and heels (I was actually going to a crossdresser event function). I had a few onlookers probably because I was changing a flat all dressed up and doing it so quickly. It was the fasted I have ever changed a tire. I did ruin the heels I was wearing in the gravel and wished I had a quick change bag like you suggested. I also learned that if something goes wrong, it is important to not get upset. Be prepared but remain confident.

    Have fun.

  8. #8
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    Again depending on where you are going I always have a pair of sunglasses, and atleast 2 femine products in my purse along with the usual items.also a little perfume. Enjoy your time out

  9. #9
    Silver Member I Am Paula's Avatar
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    Don't forget a lady's wallet! It looks terrible to pull this overstuffed brown leather thing out of a nice purse.

  10. #10
    Member Jamie Christopher's Avatar
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    Also makeup remover if you are planning on bringing a change of clothes in case of emergency; I had one early on and had the change of clothes but... no way to remove my waterproof eyeliner, mascara, eye shadow, brow liner, foundation, powder & lipstick... ended up walking into a Walgreens in drab but with my bra, forms & wig with full makeup and handbag, and bought some remover and towelettes.... turned out fine; I guess I looked like I was getting ready to do some chores....

    Jamie
    At the makeup counter

  11. #11
    Senior Member phili's Avatar
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    Re unexpected wardrobe malfunctions - a few tips so far from my days out:

    For those of us who aren't shaving our legs - tights or thigh highs are a great solution. Some sweater tights will unfortunately grab leg hair and push it straight out, but ordinary opaque tights don't. The mistake I made was thinking they would stay up. As tights pull down from walking or climbing stairs, the fun of wearing a skirt disappears. Answer: Elmer's pink kid's washable glue stick. Just wipe a quick band around your thigh, pull on your opaque or sweater tights, or thigh highs, and presto! Amazingly easy- can't feel a thing except the swish of your skirt and the breeze if there is one! Washes off in seconds with a wet washrag and just as fast out of the tights. You can also just cut off tights and make them into long thigh highs this way.

    We don't always anticipate the results of just a little breeze, and for non-tucking days, short crepe skirts with lots of tiny ruffles or pleats make great petticoat slips for that unexpected headwind that stretches your dress or skirt back over you. With these slips the interesting details are nicely obscured.

    Finally, 2 sided fabric tape is a great solution for tacking fabric that is sagging open or otherwise misbehaving! Won't hold up tights but might for sheer transparent nylons.
    We are all beautiful...!

  12. #12
    Little Mrs. Snarky! Nadine Spirit's Avatar
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    Hmmm...... interesting question.

    Things I bring:
    - a purse, love my Coach purses!
    - a female wallet, though that is just my everyday wallet as well
    - lipstick
    - a brush
    - hair clips
    - a jacket
    - blotting paper - OMG, I can't rave enough about this stuff! My skin is fairly oily and blotting paper helps to make sure things don't slide off my face. I love it. Serisouly, if you don't have it, get it. Mine is from Shisheido, but I think they also sell it at Sally's Beauty Supply.

    I think those are the only things I take every time I go out. Other thoughts:

    - visit normal places, dressed as a normal person if you don't want attention. Dressing in your sexiest outfit walking the streets at night is more attention gathering than an appropriately dressed woman shopping at Trader Joe's. Ha!
    - smile, be friendly, and talk to people even though your voice is not that of a woman
    - have fun!

    Good luck!

  13. #13
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    out in public? you're entering a new world without male priviledge, or female courtesies.
    have a bug out bag in your car with makeup remover & a quick change (sweatpants, sweater, and sneakers)
    keep your bag under your total control - my "big sister" said OK here's the deal you put your bag down someplace with your wallet, carkeys, and identification in it, and it goes away - you put your bag down somewhere you would feel ok taking off your bra.

  14. #14
    Gold Member Helen_Highwater's Avatar
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    Chris,

    Firstly, good luck on your adventure. I'm sure it'll be a blast and something you'll remember for a long time.

    OK, down to business.

    Go somewhere you know. If you don't want to go local in case you're seen and you can't do a prior drive by, use Google earth to check out the lie of the land.
    As others have said, dress age, location and time of day appropriate.
    Wear your most comfortable shoes. Heels you spend time walking around the house in without any problems can suddenly feel like instruments of torture when walking on hard surfaces for even a short time.
    Having a change of clothing and the means to remove makeup is a great safety net.
    Unless you're planning to spend an extended time out apart from a lippy and a powder compact I wouldn't worry too much about makeup.
    Handbag and purse (purse and coin purse). Make sure you have some spare change and folding money, credit and debit cards, drivers liciense or another form of ID. Also hair brush, pen, paper, tissues, sunglasses, don't forget your eye glasses if you need them, your mobi, fully charged.

    You said you're looking to be around other people so shopping is something that seems to be a real possibility. It's not easy but try to forget you're enfemme and act like you normally would (except for the walk). Remember you're not breaking any laws so behave like it's the most normal thing for you to be there. It's surprising just how quickly the nerves will calm down.

    I found making eye contact straight away with SA's gives you command of the interaction. It say's I'm not ashamed of being here. Try to make small talk, weather, has it been a busy/quiet day, that sort of thing. Don't rush when paying. Have you even known a GG have her purse ready when it comes to paying?

    Finally; good ways just to get the ball rolling are either going through a drive-in Fast food and/or using a cash machine. Short little tasks that help you settle the nerves.
    Who dares wears Get in, get out without being noticed

  15. #15
    Exploring NEPA now Cheryl T's Avatar
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    I would tell you that You Will Be Nervous !!
    You will be thinking the whole world is watching you ... THEY ARE NOT!

    It's easy to get lost in the sensation that you are the center of the universe when you go out the first time. Don't be scared to look others in the eye and smile. Yes, some may "read" you, some may snicker, but the vast majority will be so lost in their own day to day business they won't even notice you, especially if you are confident and just going about your business.

    Relax and enjoy your time out. Don't be the deer in the headlights.
    I don't wear women's clothes, I wear MY clothes !

  16. #16
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    Chris,
    Yes it does take a little more planning than you first think ! I guess it depends if you're wearing trousers or a skirt/dress, trousers make things simpler like a coat or jacket and shoes. I found little things like a purse and handbag, a women's watch and suitable glasses if you wear them. Also I had a colour match done for makeup, which does boost your confidence .
    At the end of the day we may look passable from a distance or closer at a glance but mannerisms and voice are always going to give us away, it depends how comfortable you feel with yourself to go with it .

    The question was posed recently of real or fake, and a similar one by Carla, I accept it's not an act, it's just me living my female needs and not trying to be a woman !

    As others have said when driving take drab clothes , makeup and nail polish remover, plus a torch. I'm paranoid about running out of fuel so I always fill up and as a precaution I never drink alcohol .
    Last edited by Teresa; 03-25-2016 at 03:32 PM.

  17. #17
    Silver Member I Am Paula's Avatar
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    Quote Originally Posted by rachael.davis View Post
    out in public? you're entering a new world without male priviledge, or female courtesies.

    I transitioned at 53. In the time I was male I never , even once, witnessed male priviledge. I can't even define it. It gets talked about a lot, and maybe it exists in the ivory towers of big business, but going out clubbing in drag...I don't think you'll notice any loss of male priviledge, unless of coarse you are talking about peeing standing up.

  18. #18
    Sh-sh-sh-shakin' all over jemima_bates's Avatar
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    Lots of great advice already. For me, most important are:

    - Purse/handbag. Don't be tempted to over-stuff it with a full makeup set, as it quickly becomes unwieldy. Speaking of which...
    - Essential makeup to take out for me would be lippy, concealer and pressed powder to repair any 'deviations'
    - Depending on what you're up to, plenty of cash
    - And if you're out in heels, maybe a spare pair of flats, as it might become a struggle if you're not used to it

    Most important, like others have said, is to hold your head up and smile!

    Have fun.

    Jemima x

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    AKA Lexi sometimes_miss's Avatar
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    Assume you're going to lose your purse and ID. Plan accordingly. I keep a hide a key under the car where it can't be seen even by working mechanics. Cash hidden under the car's carpeting. A xerox of my license and registration in the trunk hidden under the carpeting as well.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  20. #20
    Senior Member Hell on Heels's Avatar
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    Hell-o C C,
    The best thing I took with me that first time out was
    a good friend. Someone that had already been there and done that.
    Other than that????? I think you got enough advice already.
    Go have a great time!
    Much Love,
    Kristyn
    I smile because you are my friend, and
    I laugh because there is nothing you can do about it!!!

  21. #21
    Gold Member Read only Rachael Leigh's Avatar
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    Chris first time is always going to be a nervous time and already some great advice here.
    Mine is like others just be yourself and if your afraid to interact then don't you can just browse like many women do,
    A drive thru is an easy way to interact the first time.
    Hold your head high and enjoy the time

  22. #22
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    Quote Originally Posted by Cheryl T View Post
    I would tell you that You Will Be Nervous !!
    You will be thinking the whole world is watching you ... THEY ARE NOT!

    It's easy to get lost in the sensation that you are the center of the universe when you go out the first time. Don't be scared to look others in the eye and smile. Yes, some may "read" you, some may snicker, but the vast majority will be so lost in their own day to day business they won't even notice you, especially if you are confident and just going about your business.

    Relax and enjoy your time out. Don't be the deer in the headlights.
    cheryl hit it. Keep your chin up knowing you are not passing as a genetic woman. And that ok. Its confidence that puts people at ease, not "passing."

  23. #23
    Life is more fun in heels Genifer Teal's Avatar
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    I'd say expect to get hit on by guys. You may think- this is my first time surely they won't take a second look at me, but it could be quite the opposite. of course it depends on where you go. there are some men that are interested in us because we are trans. my first time out this guy was hitting on me so I walked away. not much longer after that he found me in the back of the bar and was hitting on me some more so I walked up to the front of the bar. not much after that he found me a third time. I had enough and left. it's only natural for this to happen. Women get hit on all the time. it's tough when it's a creepy guy and you don't know how to get away or tell him to stop bothering you. think about this in advance and be prepared should it happen. have a great time.

  24. #24
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    Quote Originally Posted by phili View Post
    For those of us who aren't shaving our legs - tights or thigh highs are a great solution.
    I found that wearing two pairs of thin tights (pantie hose) is very effective if you don't shave your legs. The first pair acts as a barrier to stop your hairs poking through. I'm fortunate enough to have fairly light coloured hair, so I can get away with very thin, light colour tights. If you have dark hair, your options might be more limited unless you go for thicker tights.

    I always take a small shoulder bag for my keys, money and makeup (lipstick and concealer, usually) and a folding hair brush.

  25. #25
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    Some great stuff here, all. Thanks so much. A couple of of things I have going for me is that I plan to be among other dressers and I'll be in a place where nobody knows me. I'm also predisposed to not give a #%~#%$&@ what people think about me.

    The issue of losing my things kinda concerns me. I think I'm just going to hold my purse the whole time. As for guys hitting on me, I'll give them fair warning before I pop them in the face.

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