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Thread: Your story of the first time a GG made you up?

  1. #1
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    Your story of the first time a GG made you up?

    I would love to hear any memories of your first time coming out to a girl and their positive response. Specifically, when the girl decides to do your makeup and dress you in her nice clothes right then and there!


    By the way, I'm asking this because it has never happened to me. 18 years old, so hopefully in the next year it will happen!

  2. #2
    Aspiring Member abbiedrake's Avatar
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    Lol Keen ain'tcha?!
    Maybe don't hold your breathe. Might take more than a year.
    I've had it happen twice in my life, and I'm 48.
    First time was my my mother-in-law during my first marriage. We were going to a fancy dress party. I went at a hooker. I bought the clothes myself, but she did my makeup. My then wife was useless at such. But then my mother-in-law went way overboard. It's worth noting though that this was 25 years before I started CDing. Lol
    I also went to work in the exs wedding dress, but that was no makeup.
    The second time was my current, keeper wife. Last year. I didn't start fully CDing until late 2017. And for my birthday last year my wife put me in a dress she'd outgrown, styled my hair into a Bob, and fixed my makeup. I loved it. But she only did it for me. She was not a happy accomplice. Having said that she's offered to help with my makeup more than once since, despite objecting to me shaving my beard off. Go figure.
    I hope, Lindsay, that popping your makeover cherry is all you hope it might be.

  3. #3
    Exploring NEPA now Cheryl T's Avatar
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    My wife was the one who did my makeup.
    I had finally come out to her and we were going to a Halloween party. I borrowed a costume which was a Red off-the-shoulder dress, mid-calf, with a black sash and lace scarf. It was a Spanish dancer complete with hair comb, castanets and lace fan. I borrowed shoes and stockings from my wife in black and she did my makeup.
    It took some time for anyone to recognize me and I spent most of the night with the ladies as they continually asked me about my costume, some wanted to know what I was wearing beneath it...
    I don't wear women's clothes, I wear MY clothes !

  4. #4
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    Lindsay,
    Never experienced it at your age . More recently I've had skin colour checks done and had my foundation applied in a makeup booth . It did feel odd the first time as I was in drab so it did raise a few eyebrows with passing shoppers . I must admit it was a nice feeling when another SA offered to reapply my lipstick , having an attractive girl that close did feel slightly erotic . As for dressing well I've had to ask on more than one occasion to be zipped up in a changing room .

  5. #5
    Silver Member Micki_Finn's Avatar
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    This doesn’t happen. Which isn’t to say it NEVER happens, but you know, some people hit the lottery too. Most of those stories you read online are just crossdresser fantasy.

    Edit: Makeovers from women are WAY overrated. Most women have no idea how to do crossdresser makeup. They use makeup to enhance their natural features whereas what we do (if done properly) is to transform our features. You really want a makeover that’s going to make you look like a woman, get a drag queen to do it.
    Last edited by Micki_Finn; 03-26-2019 at 04:22 PM.

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    Abbie-
    I love that phrase, "popping your makeup cherry"! Haha Great to hear that your second marriage was successful in the CD "accomplice" department.

    [SIZE=1]- - - Updated - - -[/SIZE]

    Thanks for the story Cheryl. Why do any guys go with boring male costumes when Halloween is the one time of the year to not get any heat for dressing like the (more fun) fairer sex... /s

    [SIZE=1]- - - Updated - - -[/SIZE]

    Teresa,
    That sounds nice, almost exactly how I'd imagine it. A little scary, but not too "perfect" and not too negative and/or disappointing. But I wouldn't have my first time be in drab though!

  7. #7
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    My Wife was OK with my dressing; So on a Halloween, she dressed me up as a french maid.
    She helped me get into some fish net Hose, and a little white apron. to hand out candy to the kids.
    I look great, and hated to take it off at the end of the night.
    Rader

  8. #8
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    never had it
    probably never will

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    Micki,
    I'm not sure if I agree but it does depend on where you plan to go when the makeup has been applied .

    Professional makeup girls tend to be too heavy handed when they do wedding makeup , too much makeup doesn't photograph well in daylight but it is marginally better than no makeup at all .

    The best solution is learn to do it yourself , I've finally struck a happy medium between applying it for everyday and a night out . The art is how little not how much .

  10. #10
    Aspiring Member abbiedrake's Avatar
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    Micki,
    Funny you should mention getting makeup from drag Queens. Before my wife first came over, before we'd met face to face, she had a photo shoot done as a gift for me, possibly parting (she had cancer at the time and was uncertain she'd survive. It's a different cancer this time). The makeup artist was a drag queen who did a fantastic job on her. So while store makeup artists can't even do GG makeovers well it appears drag queens can do CDs AND GGs.
    There you go Lindsay. You want a girl to get girly with you it's lottery odds. You wanna look amazing get a CD to it!

  11. #11
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    When I was 15 years old. That was 1967 by the way.

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    Never happened. The few times I've been made up with my wife, (or girlfriend 32 years ago) I had to do it myself. The only girls that have made me up were paid professionals.

    Sorry if that isn't as excited as a fictionmania story!

    P.s. Mickie had a point, but there are some GG MAUs that specialize. Most need tips on beard coverage and brow taping.
    Last edited by Meghan4now; 03-26-2019 at 04:55 PM.

  13. #13
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    Micki-
    The problem is unfortunately you won't find as many drag queens in your life/geographic area as you will find women, and women that you already have a trusting bond with are even more accepting and accessible than either.

  14. #14
    Aspiring Member abbiedrake's Avatar
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    The only friend I had close enough when I was your age, and was a girl who I might have confided in (had I not taken another 30 years to start CDing) was an inveterate tomboy. Suck luck. Lol

  15. #15
    tiptoeing thru the tulips ellbee's Avatar
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    I want to say I was around 17?

    And I was a young, thin pretty-boy with long-ish hair at the time. Perfect candidate, really.


    Of course, I had started seriously dabbling in my mom's make-up well before then, at age 13. Clothes? *Much* younger, at least age 6, that I can remember.

    But my GF at the time (when I was 17) didn't know about all that.


    Don't even recall how it happened... Though I want to say it was her idea. It was earlier on in our relationship. And she was the perfect blend for this, IMO... Total girly-girl -- yet with a slight tomboy streak to her, as well. Oh, and a total hottie.

    Sometimes I used to flip through her issues of Cosmopolitan or whatever teen-GG magazines she was into, right in front of her, without a care in the world. Then I think one day while doing so, she just blurted out something like, "I have the perfect shade of lipstick for you... And I want to see what you'd look like with it on!"

    Well, of course I'm not going to say no to that!


    She put it on me, and she was right: It did look great on me!

    And she also put some face-powder on me, as well as a bit of blush, then fussed with my long-ish hair to be a bit more girly. She was pleased with the results. At that age & weight and with that hair, I did look pretty decent, despite the minimalist look.

    Of course, I wanted her to keep going. And I asked, how about some eyeliner, and mascara, and, and, and...??


    No, she was having none of that.

    And by that point, with her curiosity fulfilled, she handed me some make-up wipes to take it all off.

    Sadly, it was short-lived. And she was only willing to go so far (not much, really), when it got past the point of "being fun," to being a "bit weird."



    There are other subsequent CD'ing stories with her, that perhaps I'll share here another time. But that was the first experience. (And that wasn't the only time I got to dip into her make-up stash. )


    Another time, I will mention now, is one day after school, a bit further along in our relationship, she & I were alone in her parents' house. She was watching TV in the living room, and I just sort of casually snuck off into her bedroom -- where I found the dress & pantyhose she wore to school that day & had since changed out of.

    Oh, yeah... I was throwing those on!

    I did so, checked myself out in her full-length mirror, then slowly & nervously headed to the living room, hoping for the best. I don't recall what her exact reaction was, but something to the effect of: "Ha ha! Why are you wearing my dress? And OMG, are you wearing my pantyhose, too?? Ha ha! I was wondering where you've been... Is that what you were doing?"

    What originally I thought in my mind to be a good idea to "introduce" her to my CD'ing, quickly turned into a not-so-good one.

    "Umm, yeah, okay... Go take those off, please. Right now." And she was no longer amused, to say the least. I complied.


    Long story short, she eventually ended up cheating on me, and dumping me for the new guy.

    I was heart-broken at the time... But with her apparent non-acceptance with all this, I gradually came to realize what a bullet I had dodged.

  16. #16
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    I have been surprised how many GGs that haven't had a colour check done and are basically not that good at applying makeup . It was quite amusing when my daughter saw me for the first time , she just kept gazing into my eyes , something she's never done when I've looked like dad , when I commented on what she kept looking at she had to admit I had done a great job . My sister in law is really good at makeup but she had to ask how I made mine look so smooth , I certainly didn't expect to get any compliment from her at all . It's funny now because we often chat openly about makeup , she is so comfortable with me .

  17. #17
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    Teresa I know a few women who have never worn make up just because they didn't know how and didn't want learn how.
    I have one GGF who is in her 50s and she has never worn eye make up or had her eyebrows tweezed.
    I have tried to get her to let me trim her brows and give her a make over but she just won't do it.
    She is very attractive and with some help there is no telling how gorgeous she would look.

  18. #18
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    My aunt caught me in her bra. It was much too big for me.

    She padded me out with cotton wool, and then applied bright red lipstick and lots of mascara.

    She then made me parade round the garden. I think she was trying to shame me, but I loved every minute. Thanks auntie!

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    I was....22 or 23?

    I had a girlfriend who was very open and accepting and willing to try just about anything.

    I'm from the San Francisco Bay Area and we used to have this event called the Exotic and Erotic Ball in the City around New Years.

    My gf decided to go as a school girl and I did the "traditional" ***** thingee.

    When I came out all dressed she thought my makeup was on the "nice girl side". She cleaned mine off and sat on my lap facing me and put it on. It was....really nice....Nothing fun happened. We WERE going to a party, but we were both charged up all evening.

    I'm going to agree that a lot of GG's don't do well with us. My ex wife sure didn't. Though she did teach me some techniques that I still use to this day on my eye lashes. And my daughter taught me to do a nice wing. Oth I have a very light beard and it is getting lighter with age, so beard coverage is not such a huge thing with me.

    I think as the generations change it will happen more and often. Good luck to you!

  20. #20
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    Hi Lindsay , That kind of thing only happens in MY DREAMS. >Orchid ..++..
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  21. #21
    tiptoeing thru the tulips ellbee's Avatar
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    BTW, for those who doubt it happens?

    Head on over to YouTube & search for something like "do my boyfriend's makeup" or "do my brother's makeup"


    Plenty to choose from.


    Some take it a bit further, like with clothes and/or wig.

    Sometimes they'll even go out in public afterwards.


    Yeah, yeah, I know... It's YouTube, so it's "not real."

    And yet, they're actually *doing* it -- in front of tons of people, at that!


    Just imagine how often it's NOT filmed & uploaded.

    I know my first experience wasn't. Then again, Al Gore hadn't yet invented the internet.

  22. #22
    Super Moderator Raychel's Avatar
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    Back when I was like 12 years old, My friend had a couple of sisters that wanted to dress me up and do my makeup
    Being young and stupid, I didn't let them. Looking back, I sure do wish I had.

    the only other time, My wife did do my makeup and help me get dressed for a Halloween party one time.
    I was so uncomfortable going out in public.
    my sister's reply when I told her how I prefer to dress

    "Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with"

  23. #23
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    Not sure this is what you want but I was 21 and my college girlfriend 18. When I told her about the crossdressing I was very emotional as I felt like a total freak (this is 45 years ago). It felt very scary to tell her as a bad reaction could have really humiliated me, but at the time we really liked each other and I knew I needed to tell her for us to keep getting closer. She reacted great, was very cool with it and completely took away my guilt. I had major fantasies about being made up by a girl (that was my biggest fantasy) and she totally fulfilled those - no holding back as she just went with what turned me on. It wasn't that she was so into it, but my excitement turned her on and she wanted to make me happy. She was a very pretty girl; she was very into fashion and very comfortable and good with makeup. I still remember her happily showing me the deep red lipsticks she had bought for playtime after I told her my fantasies.
    Over the years, with other women, I had more difficulties as a lot of women don't like male crossdressing but I did finally meet my current wife some 20 years ago and she totally adores male crossdressers - she has been into them since she was a kid. The odd thing is I don't even dress much anymore as it isn't quite the kick it was when I was younger although I still do like it.

  24. #24
    Female Illusionist! docrobbysherry's Avatar
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    I was over at a GG friend's last nite. She puts on her makeup in front of me if we r going out. She has to be good at it because she does a lot of live shows in Hollywood. She said mine makeup work work is terrible, (she's quite rite), and she'll do mine next time we meet!

    I would agree with Micki. But, only if u want to look like a kabuki dancer!
    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!

  25. #25
    Member amandagurl2014's Avatar
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    Had makeup done at salons several times. Most of it was positive experiences and it was worth the $ spent just to get to chat with the girls. Got tired of wasting money and decided to learn how to do it myself. Spend the money on the right products and it will pay off and save lots of $$$ in the long run. Several trips to ultra later and my makeup now is comparable to what I had to pay $30-40 to have done a few years ago. Still go to a salon to keep my brows in shape. I now have a bestie, a Cato sales lady I met about a year ago. She is around 15 years older than me. We have become great friends. It shocked me that she pursued a friendship with somebody like me. We text everyday and go out for lunch or shopping every now and then. The key is that I have been upfront and honest about myself with her. She will touch up my makeup sometimes but has never fully done it for me. She bought me a nice maxi dress and flats this past Christmas. It just feels great knowing that another person genuinely cares about you and does not think your crazy because you like to dress up and feel pretty.

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