When did you get into makeup?

[7ftEmily]

I was recently found out by my fiancée (went VERY well.) one of her very first comments was "Can I do your makeup then?" As she was making me try on the full outfit I had on when she walked in on me. It was a little awkward for me since she was just finding out and I was trying to gauge what she was thinking. I consciously said No (really kind of wish I had said yes now haha) but I'm not 100% certain if I'm ready to go that far. I've been wearing clothing only and aside from the occasional outing with panties I haven't gone much farther. What I'm getting at is how do you know when your ready and how much did you do? Do you go minimal or all out?

[Sami Brown]

Once I started dressing, it wasn't too long before I became interested in my nails. I had already started growing them out a little in order to learn not to chew on them. I just started with clear polish and sometimes wear very light pink or neutral colors for weeks at a time. This just makes the nails look healthier, as opposed to going with a more glamorous color.

It took longer, probably another year, before I started experimenting with facial makeup. I am better at some of it than others but find that, with practice, I am gradually getting better.

[Julogden]

I've always loved makeup, so that was one of the first things I really got into. My first in-person store purchase related to gender issues included a lot of makeup, and that was back in 1969. I did okay but I got serious with it in 1978, got a good book on makeup techniques, a basic set of makeup brushes and practiced a ton.

I wish I'd had a fiancée who wanted to do my makeup. You're very lucky to have her, so I'd say let her help!

[DIANEF]

I first put on a dress (had underwear much earlier) when I was about 15, pretty soon followed that up with make up. Just lipstick and eye shadow at first, but over time more and more was added. By 20 I was going the whole hog but still without a wig.

[natalie edwards]

When a woman excitedly offers help, NEVER say no!
It comes off and whats the worst that happens? You either love it or not. But I'll bet you love it! That first look in the mirror and seeing her looking back at you is incredible!

[alwayshave]

While I started dressing at 4 or 5,I think lipstick was used when I was thirteen.

[Alice_2014_B]

Beginning if 2014 was when I first tried on makeup/lipstick.
I started very minimal and progressed as time went on.
:)

[Maria 60]

I never even considered wigs, jewelry or makeup before joining here. I was only wearing women's cloths and when i joined here i started reading threads about wigs and jewelry. I asked my wife about makeup and she suggested we don't share and that I buy my own. We did and she showed me how to apply it. With this site I now have my own jewelry, wigs and makeup, I feel much more complete and don't know how I dressed all these years without it. As for your fiancée I would go with whatever she is curious about. My wife loves having me as her husband and girlfriend to shop with and try on each other's clothes, maybe she wants you as her girlfriend. Feel blessed that she OK with it.

[Aunt Kelly]

Hi again, Emily.
Natalie's advice is sage. When your SO offers to help, you must do two things. First, say "Yes, please." Second, start thinking of ways to let her know how special she is. Seriously. You have a gem there. Make sure that you show her that you know it.

As for when to take that step, it doesn't matter. If you're curious about it, give it a try. Let your SO make you over. She'll have fun and you'll probably be amazed at the results, both visually and emotionally. Fair warning though. Feeling pretty can be habit forming. :)

Hugs


Kelly Marie

[sara66]

I started experimented with makeup when I was a teenager. Bought my own mid 20's. 95% on the time I am all or nothing when dressing.
Sara

[IleneD]

Emily;

The makeup is a final element of a complete transformation. Do it. Make up creates an impressive appearance and illusion, and in my mind is the one thing that makes an incredible difference in credible appearance. DO IT. Do the make up.

[gender_blender]

I always loved having my makeup done by friends and makeup artists for photoshoots, so I picked up some tips & watched some video tutorials.

[ashley_addams76]

About 5 years ago. Just decided to watch videos and practice. I have gotten better. The sensation of looking like a woman is amazing.

[Jane P]

Emily , I don't know how things have been going for you and your fiancé since she found out but , if things went well other than you saying no to the makeup then talk to her . Tell her that you were afraid , tell her that you didn't know what she was really thinking about you at the time . Ask her how she feels about knowing this thing about you and if she is still okay about it , ask her to do your makeup sometime if she would like . If the cat is out of the bag , find out if this will bring you closer or drive you apart . Best of luck .

[docrobbysherry]

If you've ever seen photos of me? U know I'm not!:sad:

[Cheryl T]

I got into makeup when I was about 16. I had a p/t job and saved money, bought a wig (very cheap) and some makeup. I loved it !
Unfortunately I looked like a cheap hooker since I had no idea what I was doing. All the images I had to go by were in men's magazines and you know how over the top that can be.

[Jenny22]

Makeup transforms the face, done properly, and a willing and experienced female can do wonders. Let her do it for you and thank her a thousand times! Now that the face is pretty, you need to transform your head. A good wig is the only answer. Ask your fiance' if she will help you buy one. Use a wig store, if possible. Give her a hug and a kiss and treat her to something special!

[miki s]

Haven't attempted a make-over yet but I just know it will be a disaster.

shamelessly posting to get 10 posts and access the make-up tips forum

[7ftEmily]

I appreciate all the responses I've received!

I took info from several of the posts and talked to my fiancée today. I asked once how comfortable she was with everything she's found out since last week. I then asked her about the makeup, she replied by saying " I can do yours but we'll have to buy your shades." ( I'm a darker Hispanic, she's an almost albino[me exaggerating] Caucasian.) So maybe this weekend with payday we can do something.

Believe me I've thanked her for understanding and being okay with it plenty and we even crack jokes on the subject on occasion. ( she's mentioned to let her know when I get uncomfortable.)

[CONSUELO]

Very early when trying on clothes and using lipstick. i used to watch my sisters very carefully as they put on their makeup and I also watched my Mother and my aunt and that way I learned a lot.

[NancySue]

Very shortly after I began dressing. I'd watch my mother and would copy what she did. The first few times were funny, but later, it got easier. Once, I didn't get all the lipstick off and she asked me if I had been wearing lipstick. I said "no", but I think she knew. Things are much easier now, except for false eyelashes.

[Kyle20]

I think it was when i was in high school i would watch my mother and then copy while she was at work. Neighbor came over once while i had eye liner on. She didn't say anything to me about it. One time i was watch my mother and she put mascara on me and i had it on until she was done then wiped it off.

[Rachael Leigh]

I first started to try using makeup in my 20s and was not very good, think clown lol.
It wasn't really until a few years ago I began to experiment with buying and using my own on a regular basis
I'm completely self taught in how I do it but have watched a few videos. And did have a makeover earlier this year.
For me this is one of the most enjoyable parts of my dressing I enjoy giving myself a nice clean and soft but feminine look
it's a work in progress but I love doing it

[sometimes_miss]

I tried playing with my sister's make up when I was in high school. Seeing that there was no way to hide the hideous birthmark, I just gave up and covered the mirrors. All I could see then, were the clothes and accessories from the viewpoint of my own eyes, so make up wouldn't make a difference for me anyway.

[Shannon michelle]

I tried eye shadow when I was little but still have not tried full makeup I go down the make up aisle and get so confused. My wife and I are planning a trip to MAC to at least get some help withthe right foundation.
Shannon

[Alice B]

From the very start of my trying dressing. Make up is a major factor in getting the "feeling" of being dressed.

[JeanW]

Other then lipstick never really had tried anything else but I didn't wear anything but panties till 6 years ago when we had " the talk " . A while after she had bought my first dress (had me very scared and excited) she told me maybe I should try putting on some makeup. I told her I felt makeup was something worn for others to see (I felt it was something done for sexual attraction). Her reply was us girls wear it to make us feel better about ourselves too. And it was in the bathroom if I ever wanted to try . Having had watched women in my life doing their makeup or even applying their lipstick (lipstick has always been a big thing for me) anytime I had the chance to. I guess curiousity got the best of me and she had bought a mascara and gave it to me. I finially got enough nerve to try it privately much like the dress when she gave it to me I was scared to have her see me with it on. I have since got so I do wear makeup most times its very lite and casual amount I have done a much more dramatic makeup a few times when alone now too. I when time allows also use fake nails which I truly love having on and polishing .

[Dana44]

I started makeup a long time ago. Guess my twenties. Started really applying it well in my thirties and forties. We learn something new and perhaps new ways to do the eyebrows and such getting better as time goes on.

[Aunt Kelly]

Played with mom's mascara and lipstick a time or two, but it was never a thing until I came out to my girlfriend in college. She was very supportive and would make me over. That kinda lit the fuse.

[Ceera]

I was a 'late bloomer'. Aside from trying wearing panties under my male clothes starting in 2012 or so, I didn't try dressing at all until I was in my mid 50's, back in early 2014. When I admitted to myself that I really wanted to step out that door and be seen in public as female, I knew I had to learn at least basic makeup skills.

I had dark circles under my eyes, and a relatively noticeable beard shadow even when I shaved carefully, as well as excess redness in my face from too many years of sun exposure. All of that needed to be corrected or compensated for if I even hoped to look like anything other than a man in a dress.

I started with on-line tutorials, and tried buying some inexpensive makeup at Wall-Mart and Target and the like. I also steeled my courage and went to a department store makeup counter, telling the sales associate that I was wanting to correct the dark circles and redness, while retaining a look as if I had no makeup on. Between those sources, with about three months practice, I learned enough to at least look reasonable in a club environment, at night.

When I felt brave enough to try going to a busy mall en-femme, in daytime, which was in August 2015, I scheduled a makeover at Sephora, and learned much better skills. I also started getting my eyebrows threaded, to trim them to a narrower, less bushy and more feminine look. Armed with better products (and a lighter wallet) I worked on my makeup application skills, and now feel I can pass pretty darned well. GGs often complement me on my look.

I don't tend to go for lots of eye shadow or eye liner unless I am going to an evening event where a GG might reasonably be expected to wear that type of makeup. Nor do I go for a heavy or obviously non-natural look. In general, I try for a clean, natural look, with a nice shade of lipstick and my eyebrows darkened to match my wig color.

Pic in the white blouse is early 2015, before I had that first makeover. The other pic is me now, when out for dinner with my daughter.

[MonicaGirly]

Well, I always really wanted to try makeup, but as a youngster I could never risk trying it because it takes so long to fully take off. So aside from a couple of risky lipstick tries here and there, I couldn't.
That is, until I got to college, it was actually my junior year of college when I finally lived in a place that gave me enough privacy to actually experiment with makeup and try it. Ever since then I've loved every bit of it. Maybe when I go back to school in July I'll be able to pick it back up again.

[BrendaPDX]

I only started using makeup about 6 years ago. Loved it, I can still remember the woman looking back. I and I really liked how I looked, wouldn't have minded dating me😍 Thanks for the question. Brenda