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Thread: When did you start doing makeup?

  1. #1
    Aspiring Member
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    When did you start doing makeup?

    I did not try makeup until I was in my late 20's. I did try lipstick in my teens but it really never took hold. Makeup was another step in my journey. When did you start in makeup? Was it full warpaint from the get go or did it progress?
    Sara

  2. #2
    Junior Member stefaniec's Avatar
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    Using makeup followed long after I first started dressing up. But it is mainly for the same reason that I didn't have much to try on in my early teens when I started. My only way of dressing up was "borrowing" stuff from mom's wardrobe which was fairly limited anyway. And she wasn't that into makeup. So my use of makeup really took off when my dressing up took off--when I was finally done with college and on my own with my own place. Of course when I first tried my hand at it, I had no idea what I was doing and it didn't look very good to say the least. But yeah, there was a good 12 0r 13 year gap between first starting my journey and then getting to the point where I included makeup in the routine.

  3. #3
    Aspiring Member Geena75's Avatar
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    I didn't try anything really until last fall, when I realized a way to show at least part of my face. Up to that point I would just try to ignore my blatantly masculine look. Mostly I work on making my eyes look right. Now I'm working on plans to shave clean and finally really see what Geena looks like.

  4. #4
    Senior Member Angela1954's Avatar
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    Started in my early 50's after my wife and I split. The first time I did it and went out I looked like the Frankenstein monster lol. Just drove down to the gas station, got out, filled my car, and quickly got back in. My techniques have improved but there is always room for improvement.

  5. #5
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    I think the first time we all did our own makeup we look terrible. It took a half a dozen attempts before it just looked bad. It took a solid year before it was acceptable, If we did makeup everyday we would look good all the time.
    Sara

  6. #6
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    I started in my mid fifties after finally shaving my facial hair. Im sure I looked horrendous early on but after a few visits to the makeup counter I have developed a decent look.

  7. #7
    Exploring NEPA now Cheryl T's Avatar
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    Oh I remember wearing mom's lipstick when I was about 8 or 9.
    My first attempt, and I do mean attempt, at full makeup was when I was about 17. I had acquired everything I needed and one day no one was home. I hurried and dressed then went to the bathroom and gave it a go.
    All the images I had to go by were magazine ads and this was mid 60's. I of course thought I looked sexy and I sure felt hot. I ventured outside in the back yard and strutted my stuff. Short skirt, garter belt and nylons, bra stuffed with toilet paper and my face probably bringing shame to hookers everywhere. Of course it ended with relief, followed by shame, guilt scrubbing of my face and an outfit change worthy of Superman.

    It wasn't until 3 or 4 years later that I had become deft enough to dare a public venture again.
    Now it's second nature of course, but then what wouldn't be after all this time.
    Wear what makes you feel Confident !

  8. #8
    Weirdest woman ever! docrobbysherry's Avatar
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    Looking at my photos? It looks like it was yesterday!
    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!

  9. #9
    New Member Leanne.cd.uk's Avatar
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    For me. I had done the little use of lipstick for years. Only so my male friends could have the lippy marks where it matters 😂.

    But after my marriage dissolved I went full on Leanne and started seeing what I could be. After a few months I found my rhythm with it and went from bloke looking rubbish to what you see on my pic today.

    YouTube helps and having a gf who will advise on bits.

  10. #10
    Gold Member Helen_Highwater's Avatar
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    Looking back at old photos shots with me wearing makeup are rare, mainly I suppose down to being in the closet and having both limited time and access.

    I was probably in my 40's when I started to acquire my own makeup, mainly multicoloured palettes of eye shadow, the odd lippy, foundation "borrowed" from teenaged daughters.

    Once I started going out enfemme did I make the real breakthrough. A visit to the Boots No7 counter for a foundation check revealed I'd been using a shade more suited to clown makeup than anything else.

    This was the big change. I now had blusher, lippy, highlighter that complemented each other and weren't competing to be the worse colour from a poor choice.

    It was transformative both in my presentation but also my confidence. Knowing the clown was gone and that I looked that much better allowed me to go from strength to strength. Short of a full makeover probably one of the best days ov my CD'ing career.

  11. #11
    Resident Polymath MarinaTwelve200's Avatar
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    I started with my moms red lipstick when I was 12 and had a day alone at home. In the late 50s and early 60, as a kid, I was oddly affected by the teen girls and women with their red lipstick. It was "freaky" as to how much it changed their appearance and gave them that "womanly look". (but I kept it to myself). One time, When I was 8, my mom was putting on her makeup. I was near by and watching, and Mom , in a "goofy mood" called to my father, "John, Lets put some lipstick on Marty". I was shocked, but Dad grabbed me and held me so I couldn't move my head and mom approached me with her open lipstick. At the very last moment she backed off and said "we better not do that, it might give him a complex. But I think the harm was done. For the 3 or 4 years I wondered what I would look and feel like if she had put that stuff on me. So finally , at age 12 I had an opportunity being home alone all day, along with the drive so I went ahead, determined to put it on myself. I first tested it on my wrist to see if it would come off. It did! so I knew I would be safe. ---Needless to say, it was very "exiting". I "got off" very quickly. And was able to successfully remove all traces of it. For the next year or so I only did the lipstick when the opportunity was there. ------Then one day, when my folks all went to visit some out of state relatives, I got to stay home for a whole day alone, I decided to try DRESSING for the first time---ALL THE way! In one fell swoop. From nylons to girdles to bras slips and a dress, topped off with lipstick and other makeup.-----I looked a MESS, but though I resembled A retro Elizabeth Taylor (That pink fog can really affect one's perception). Marina was born. And I have continued, with a few breaks in between, ever since. Getting better at it over time.

  12. #12
    Senior Member Christie ann's Avatar
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    I started makeup only about 10 years ago when I bought my first wig. It was something about being the whole package. I had the opportunity to travel a little bit so I could get makeovers at department store makeup counters. I saw the change from “ we don’t do men” to sit down here and let’s see what we can do. They gave me lots of tips, but I still looked like you gave 3 year old some crayons.

  13. #13
    There's that smile! CarlaWestin's Avatar
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    It wasn't until much later on in my journey that I started doing makeup. After my ex made me up for pictures
    I noticed how feminine my appearance could actually be. Then a couple of years ago I discovered that a minimum amount of makeup
    achieved the best results.
    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!

  14. #14
    Platinum Blonde member Ressie's Avatar
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    1974, I was 21 - our band did a gig in Chicago with the "Shadows of Knight" and the cute lead singer was wearing eyeliner. I was inspired to try it myself and since there was eyeliner in the medicine cabinet I applied some. I found it arousing but I don't remember when my next makeup experiment was. I didn't start buying makeup until around 2005 or so.
    "You're the only one to see the changes you take yourself through", Stevie Wonder

  15. #15
    Girl Power! CrossKimmy's Avatar
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    I started using make up in my 20s as well. I wish I started earlier. That and shaving my body too.

  16. #16
    New Member Donna Lynn's Avatar
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    I started using makeup in my around 1991 after my divorce, Wanted to explore more about my dressing. Had to give full dressing a try a makeup was a big part of the look. Very bad at it , A close friend said I should try a gay bar, she new of one that had a Drag show . Go dressed you will blend in, I did go I did not blend in. After 3 or 4 trips to the show on of the dressed girls in the bar gave me some tips . Found out later she was Trans not drag. My makeup got better still not good but better. Witch got me into going out more and to more places.

  17. #17
    Aspiring Member DianeT's Avatar
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    I started about the same time I started dressing, around 11. Since I stole things from my mother, I could use foundation red lipstick mascara and... yes, blue eye shadow.

  18. #18
    Aspiring Member jacques's Avatar
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    hello Sara,
    make up is probably the last item I added to my cross-dressing, maybe five years ago. I have like the wearing of Covid face masks because nobody know I am wearing lipstick!
    luv J

  19. #19
    Member Audrey34's Avatar
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    I didn't try using makeup until roughly 10 years ago. I was so clumsy at it at first, but thanks to several wonderful cis-gender lady friends, they taught me a lot and urged me to keep practicing. I'm much better but I still wish I could afford a makeover, lol...

  20. #20
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    My first use of makeup was lipstick when I was about 18. I didn't try anything else until many years later.

  21. #21
    Aspiring Member fun4metoo2004's Avatar
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    I gave it a try early on unsuccessfully. it was not until about 2018 (58 yr old) that I have done it in earnest to make it look good.

  22. #22
    Senior Member TheHiddenMe's Avatar
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    I started about 20 years ago when I was in my early 40's.

    The key for me was in October 2016 when I went to Sephora for a makeover. I had a great MUA, Julie, and I took notes and bought much of the makeup she used. That gave me confidence and the tools and process and that has made all the difference in the world. I recommend scheduling a makeover for yourself at Sephora or another place.

    I have also found that less is more. I try to get the foundation right; cover my beard, but not so much I look like a drag queen. These days, I usually don't do my eyes other than mascara. I figure if someone is close enough to see my eyes (I wear glasses), they likely know already I'm not a GG. It also makes it easier to clean up afterwards, and saves me time.
    I'm Sun-Dee at Kandi's Land; read about my outings here:

    https://www.kandis-land.com/author/dee/

  23. #23
    Member Lori Ann Westlake's Avatar
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    As I recall, I didn't start doing makeup until I was with my (fortunately very accepting) wife. This is a good question that made me ask mysell why. Up until then, it was more the "feel" and knowledge of being in women's clothing and women's underwear that I enjoyed. Being closeted, my actual appearance mattered less, and I wasn't looking in the mirror so much. I think my wife's acceptance encouraged me to explore further the accouterments of femininity, and besides, being with someone else, who was looking at me, led me to pay closer attention to how I appeared.

  24. #24
    Life is more fun in heels Genifer Teal's Avatar
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    I mastered wearing heels in my early 20s. I quickly got bored walking around the house. I needed makeup to go out.

  25. #25
    Oh to be an English Rose Jane G's Avatar
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    In my early teen I experimented with my sisters make up, just me having fun being a girl. I was in my late twenties before I bought my own. I would go out occasionally back then. I don't often wear full make up any more, as I am just pottering around the house doing stuff. though I always wear lip stick.

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