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Thread: What did you struggled with when first dressing?

  1. #1
    Brandi Brandie.n's Avatar
    Join Date
    Jan 2014

    What did you struggled with when first dressing?

    What did you struggle with when you first dressed?Then one fine day you was doing it like normal forgotten you had to struggle with it?
    Me first,my struggle was hosiery every time i put on tights or pantyhose I would twist the leg.I would have to take them on and off until I got it right.I could put on stockings and wind up twisting the leg lol. Today I was playing dress up and put on my hose and it hit me I got over that hump.I can put them on the right way now but,I don't remember when it clicked and started putting them on the right way..
    Walk a mile in my..heels

  2. #2
    Yeah Ok like whatever Tracii G's Avatar
    Join Date
    Aug 2008
    Between here and there but mostly here close to the donuts.
    Make up for sure.
    I know lots about make up and how to apply it correctly now but I still mess up sometimes and get it all wrong.
    Head Executive Chief of the Dept of Redundancy Dept.
    Expert plumpologist

  3. #3
    Weirdest woman ever! docrobbysherry's Avatar
    Join Date
    Sep 2007
    Orange County, Calif.
    My face!

    I nearly quit dressing before I'd really gotten into it. A hot, young woman's shape with the face of a homely old man!

    Then, Halloween came and I tried on a female mask!
    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!

  4. #4
    Senior Member Jean 103's Avatar
    Join Date
    May 2013
    Central Coast, CA
    Self acceptance and guilt.

    I still remember as it wasn't that long ago.

    As far as dressing it would be false eyelashes. I still have problems. Lucky my lashes are ok so I just use mascara.

  5. #5
    Gold Member Helen_Highwater's Avatar
    Join Date
    Jan 2010
    Midlands UK

    Shoes, trying to squeeze my size 9's into my GF's size 6's.

    Makeup as Tracii says was always an issue. It wasn't until I had a foundation match that I realised I'd been using one too light and so veered more towards a clown face.

    Now thankfully I've learned to put on a workable face and in about the same time it'd take the average GG. Still can't get to grips with liquid eye liner though.

  6. #6
    New Member Sarah Handy's Avatar
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    Nov 2019
    Houston Texas
    Walking in heels and still struggle.

  7. #7
    Silver Member Bobbi46's Avatar
    Join Date
    May 2015
    France, Villessot near St Christophe
    Lipstick! when was too much too much! now I put my lippy on and then close my lips over tissue until the surplus has come off then there is no problem with cups and so forth
    I started life a lost man now I am a found woman

  8. #8
    Gold Member alwayshave's Avatar
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    Dec 2011
    Washington, DC
    For me, it was then and still now, eye makeup.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  9. #9
    Aspiring Member Angela1954's Avatar
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    Feb 2015
    Upstate NY
    I agree with Jean. Self acceptance and guilt; which I am still plagued with from time to time. As for the other issues; as many have stated makeup. It is an art form; which I still struggle to master.

  10. #10
    New Member EyoN's Avatar
    Join Date
    Jan 2019
    I reckon many, including myself, struggled with make ups (and especially eye make-ups).

    However, I personally also found it difficult to conceal wide shoulders and chest, as well as low waistline, and it really comes to picking the right cloths. Even if the cloth is just the right length, it is almost always too tight somewhere.

  11. #11
    50's Housewife Wannabe Madilyn A.'s Avatar
    Join Date
    Jan 2010
    False eyelashes, getting my wigs just right, finding heels in my size, and sufficient time to dress and enjoy myself .
    Believe in the impossible dream, dreams do come true !!!


  12. #12
    Aspiring Member GretchenM's Avatar
    Join Date
    Dec 2016
    Denver, Colorado
    Guilt about doing something I "knew" was wrong but couldn't help myself or stop. It was a deep internal drive and it scared the crap out of me. Did it anyway. I was only 7 years old, that was 1952. And I suffered the consequences when I got caught. Drove me into a very deep closet for 60 years. Now, no guilt - it is a part of who I am, warts and all.

  13. #13
    Girly Girl gailprice's Avatar
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    Jul 2006
    London SE
    Yes, make up for me. Eyes were the worst.


  14. #14
    Senior Member BrendaPDX's Avatar
    Join Date
    May 2016
    Portland, Oregon
    Makeup, then and still now.

  15. #15
    Member Jessie Mae's Avatar
    Join Date
    Oct 2019
    Youngstown Ohio
    Makeup; eyes (hooded) and lips (thin). And self-acceptance.
    Two penguins are standing on an ice floe.
    The first penguin says, "You look like you're wearing a tuxedo."
    And the second penguin says, "What makes you think I'm not?"

  16. #16
    Member Zoeytgtx's Avatar
    Join Date
    Oct 2017
    Middle of AR.

    In the beginning, a lot of guilt and self loathing. Completely denying it was NOT ONLY the dressing. Of course, learning how to do eye makeup and liner on my hooded eyes.

    Five year later, I happily understand I?m TG and unashamedly go out in public and I present quite nicely according to my GG friends. It?s all about growing into who you really are and accepting it.

    Hugs, Zoey

  17. #17
    Join Date
    Nov 2005
    Men. How to deal with men. I knew guys were trouble but it seemed that since I became a girl I met a whole new breed of men. And it was a struggle learning to weed out the psychos.

    Make up was easy for me. Just took a pic I liked from a magazine and copied the look to my face. I already was using artist brushes to paint so I knew how to draw a straight line with the liner.

    A minor struggle was trying to find goth clothes back then.

    PS- Finding a job as a t person was a struggle.
    Last edited by Amelie; 12-12-2019 at 10:27 AM. Reason: Added stuff
    Hiding in my room, safe within my womb.
    I touch no one and no one touches me.-S&G

  18. #18
    Senior Member Majella St Gerard's Avatar
    Join Date
    Jun 2013
    Myrtle Beach SC
    Make up was tough, but I got that down, liquid/ gel eyeliner I can not do though. Heels are not that hard to master (under 5 in.) unless you have a balance problem

  19. #19
    Senior Member NancySue's Avatar
    Join Date
    Jun 2016
    Southern Illinois
    My first experience was with nylons. It was fun but, I struggled with slipping them on correctly. Then finding time to wear them again along with some guilt and fear of getting caught. I?ve overcome guilt and fear long ago...thanks to my wife. Currently, putting on my makeup is always a venture. As with life, I have good and bad days.

  20. #20
    Silver Member CynthiaD's Avatar
    Join Date
    Jul 2011
    When I first started buying my own dresses, it took forever to find the styles that looked good on me. My local thrift store has a whole rack of my mistakes. (Well, they could if they put them all together.)

  21. #21
    Exploring NEPA now Cheryl T's Avatar
    Join Date
    Feb 2006
    Jean 103 nailed it.
    It was the guilt and shame for me. I loved the clothes, could dress with ease even with seamed stockings, I was walking in heels when I was about 8, but removing the clothing and feeling all that guilt and shame was the worst.
    It was decades before I was able to accept myself.

    Now the challenge is makeup for an older gal. Eyesight requires glasses so eye makeup is my nemesis.
    Can you see the REAL Me?

  22. #22
    Platinum Member
    Join Date
    Oct 2010
    Western Washington
    My first interest in wearing women's clothing was in the early 1960's. I struggled with just the concept of wearing women's clothing. Back then the word on the street, i.e., society, was any man wearing women's clothing was a homosexual. However, the word homosexual or gay was not used. All terms were derogatory. This brought about a lot of conflict since I lusted after girls my age and unattainable starlets on the movie screen. Any way, the early years were filled with self loathing, disgust, hate, confusion about myself. Obviously the internet did not exist back then. There was no printed material around for a kid to read. Even the local library hid behind the librarian's desk the copy of the Kinsey Report. If all you had to worry about was trying to put nylons on then you are lucky. That was the least of my problems back in the 1960's.

  23. #23
    Member Star01's Avatar
    Join Date
    Aug 2018
    The first time I dressed I was too young to understand what was going on. At first it just seemed like a one time incident and as bad as I felt I obviously wasn't going to tell anyone. Well, here I am about 56 years later at 68 and I guess that it wasn't just one time after all.

    Today my biggest struggles are applying eyeliner as I need to wear reading glasses and I have always had trouble shopping for girlie things in guy mode. I went into a thrift store yesterday with my nails clear polished and star earrings while underdressed in a thong, looked at the women's shoes, looked at the ladies browsing the dress racks, freaked out, smiled and said hi to the clerk and left.

  24. #24
    Silver Member
    Join Date
    Jan 2016
    Orange County, California
    Too much self gratification, and the post shame of it. Much later, my need to acknowledge that I was true TG.

  25. #25
    Member April Rose's Avatar
    Join Date
    Oct 2017
    Star , the eye makeup thing is a no win situation for me; can't see what I'm doing with my glasses off, can't get at it with my glasses on!

    Since my first memory of being attracted to women's things was also my first memory, my earliest trouble was overcoming the feeling that I was bad and queer and going to hell.
    I am a vessel of the goddess. Let me express my calling to a feminine life through nurturing love and relatedness.

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