A new frontier...

[Maximilian]

As usual, a long post. Hope you stick to the end.

Those of you who have been following my posts over the past few years could see the journey I've made from the first few scary steps in heels outside of the safety of my home to wearing skirts, otk boots over skinny jeans, a dress/tunic and more in public for all to see.

It's been a fun/rewarding ride where I've discovered that the world around you doesn't stop and fix their eyes on you just because of your fashion style. It has definitely improved my confidence and I have to thank the many members on this site for all the help and support over the years.

No, this isn't goodbye lol, just that I've discovered that there is one more thing I felt was missing which I have found. For me, it turns out to be makeup.

I think that I've mentioned in previous posts that makeup was not something I was into. Well, I guess that changed along the way. I'll say this, 'Elegant' was right!

It started by applying foundation, concealer and setting powder to give myself that even and smooth facial skin look. The fact that I have dark hair and that my facial hair grows rather quickly, I was annoyed with my '5 o'clock' shadow'. No matter how smooth my shave was, it was always there. In my opinion, A guy in heels, skirt as well as a shadow of a beard/stash do not go well together. The facial makeup took care of the problem.

The first time I went to buy makeup wasn't really nerve racking since I was dressed as a guy going to a dressy lounge. I actually went to "Shoppers Drug Mart" for the makeup since they were carrying a product designed for men.

However, after speaking to the 2 lovely salesgirls/Aestheticians, they recommended another product which did the trick beautifully.

They didn't flinch when I told them that I wanted the makeup for myself and were actually quite excited to be able to work on a guy who's had makeup put on for the first time. I've spent a good 30 minutes being worked on, talking and getting to know them. It was fun! However, the subject of freestyling did not come up.

This happened about 2 months ago. Since then, when going out in a feminine style, I always put on makeup. I like my total look much better now. But wait! The more interesting story happened last Thursday.

I was browsing the internet and came across some photos of male celebs who have put on eye makeup, most had that dark/smoky/glam rock look. I found that to be appealing. So I said, 'what the hell', lets go get some eye makeup done. The place of choice was MAC Cosmetics at the West Edmonton Mall.

This time, I chose to wear a low key feminine style, as you can see with the photo attached (an older photo yet the style is the same). I was wearing black leather pointed toe ankle boots with a 2.5 inch heel, perfect for style and heel walking comfort, blue bootcut jeans, black turtleneck top and a black leather jacket. Every piece of clothing I was wearing was intended for women, except my underwear lol.

I arrived at the mall at around 17:30, it was pretty empty to my surprise which turned out to be a very good thing once I’ve entered the store.

When entering MAC I’ve felt as though I was trespassing as it looked like the Mecca for women, kind of like what women would think of the tools sections of Home Depot lol.

Hundreds of different lipsticks and colors to choose from. I felt a bit overwhelmed. There were 1-2 female customers in the store when I’ve entered and 4 saleswomen, all young.

So here I am, walking towards one of the girls with my stiletto heels clicking. I managed to confidently tell her that I’ve recently discovered the world of makeup and that I came in order to be helped with choosing and applying eye makeup for myself.

The salesgirl, who turned out to be the store manager didn’t flinch and asked me what kind of style I was looking for. I told her that I was interested in 2 different looks. The first one being a natural day to day look which would very gently enhance my eyes. The second one was an evening smoky/dark/mysterious look. She told me that she needs to take care of something but one of the salesgirls will help me out shortly. I browse around for a minute or two until a GORGEOUS saleswoman comes from the back of the store amd tells me that she’ll be more than happy to assist me with the makeup.

I mention that I’ve never applied eye makeup before and that I was in her good hands which brought a big smile to her face. She starts picking various colors while telling me how each one will work together.

I nod without having a clue what she was talking about and tell her that she should put on whatever she thinks will work.

We looked for a high stool in the store and she asked me if I was fine with the stool positioned right beside the store entrance where everyone passing by the store as well as everyone inside can see me. “No problem” I reply.

So here I am sitting fully exposed on a high stool with my legs crossed, wearing stiletto boots and having a beautiful woman (around 5 foot 8, long red hair, green eyes, perfect makeup, body of a supermodel, wearing a black sleeveless shirt/black form fitting trousers/black leather 3-4 inch pointed toe stiletto pumps) working on my eye makeup. I was in heaven!

I spent a good 1 hour being worked on, glimpsing at the mirror from time to time to witness my transformation. Every now and then she left to help a customer, only to come right back and continue playing around with colors and brushes on my face lol.

She explained that I chose a good time to come by since it was slow and she could devote so much time to me which normally doesn’t happen. We got to know each other during this time. She turned out to be married (to a pro hockey player), a mother of 3 young kids (I wouldn't have guessed that she was in her mid 30’s), 3 years in the makeup business, a former flight attendant etc...

She loved my facial skin and said that it was so much fun working on it and that the end result will look great with my outfit. She also claimed that the evening eye makeup would look awesome with a dress although I told her that I don’t do dresses.

Obviously she noticed the heels and complimented the total look. It was funny because she talked to me as though I was her best friend, sharing stories, talking about fashion etc...

I don’t think she was totally convinced that I wasn’t gay although I told her a few times that my target crowd were women to which she responded that my outfit and makeup would make all the girls and guys jealous. I did ask her if there were any other guys who came to do their makeup there. She knew a few, specifically a guy who performed as a drag queen and came in to get his makeup done before a show.

I was really pleased with the results of her work although I was a bit taken back by my first glimpse of my evening look. She said that it will take a bit of getting used to but she thought that it looked great as well as the other saleswomen who, during that hour or so, constantly came by and said “how hot” I looked. I was unaccustomed to all the positive attention and compliments in such large doses lol!

During all that time, many customers came in and out of the store which included couples, a group of teenage boys and girls, young women and moms with their children.

A little girl, I’d say about 5, spent about 10 minutes watching how the saleswoman applied makeup to my eyes, a common thing as explained to me by her.

With all the looks I got, the only comments I’ve received came from the saleswomen who really liked the result. If I had a few doubts about their sincerity with regard to my look and makeup, it was gone by the time I left the store. The saleswoman who had worked on me gave me her card and told me to come back anytime and if I ever needed help putting the makeup on, that I should come back and she’ll be more than willing to help me.

It was a fantastic evening, so fantastic that I forgot a shopping bag of mine at the store. They kept it for me and when I returned the next day to claim it, I was received very nicely although the saleswoman working on me wasn’t there at that time.

Naturally my confidence was sky high afterwards and I decided that I couldn’t let my evening eye makeup go to waste (it will be a while before I'll be able to get the end result I got at MAC) as I requested to keep it on.

So I went to trendy Fusion restaurant which is known for its good food as well as its pretty servers/hostesses. The place was almost full so I decided to go sit at the bar since I was all by myself. The female bartender was very friendly and commented with a ‘wow’ when she first saw me, mentioning how much she like my makeup which made me look like some mysterious stranger.

I thanked her and said that we had pretty similar looks that evening since she too had that smoky look on. During our little chitchat another 2 female servers came by to compliment me after the bartender mentioned me to them. Unfortunately, all of them had boyfriends (a fact that I’ve learned through the bartender) so it was another no go in that department arggggh! It was a great evening nonetheless.

I do feel now that with the makeup, my total look is pretty much complete. I’m at the border limit between a guy with a feminine style and a guy pretending to be a woman which I have no desire to be. For those of you who’ve reached this far, thanks for reading!

P.S

I do not have a photo of mine with makeup on yet. I don't like taking ‘on the go’ snapshots anymore but more thought out photos so when I have the time and will, I’ll post new photos.

[Guest]

love the long story max, but if you took the pic with the makeup, its too small-I really cant see it all that well. (by the way, I wear lip gloss my self, I love it!)

[JeffB]

Fascinating, Max! Looks like you've taken another step along your own journey, indulging in new experiences. Good for you, my friend!

[Bubba136]

Progress! While I don't anticipate ever turning to the make-up thing (way too much trouble (fussy) for me -- don't have the patience), I congratulate you on your courage and determination to learn how it works and how make-up works. Great posting.

[Dr. Shoe]

I wear make-up too...

[Bootking]

Great move Max - it shows, fashion and make up are not just for the girls! Bravo!

[Steve63130]

The only cosmetics I ever buy are Sherwin-Williams. Steve

[wood&metal]

As a female friend of mine says of Johnny Depp/Capt. Jack Sparrow in pirates of the caribbean, "the eyeliner just makes him sexier"......

Another guy who wears eyeliner is Billy Joe Armstrong in the band, Greenday.... Women seem to love it...

Maybe there's something to it....hmmmmm

edit: youtube video link.. http://www.youtube.com/watch?v=r6vsxTZPjEA

[HappyFeat]

Max, thanks for the post! I have been pondering going to a store and having makeup applied and dabbling in wearing it on occasion. I have a approached a few sales people and have bought a couple of products, but for one reason or another have yet to try the application. Like Bubba it would be a bit fussy for me to wear makeup on a regular basis, but your very positive experience inspires me to get out and give it a try in the near future.

[jwhite44]

Great description of you day. Major disappointment that there were no accompanying photos of your session. If you ever go back, you might consider taking your camera, and asking the woman to take pictures of you at various stages her session with you. If you looking to be able to eventually do this yourself, I'd think it would be very helpful. Regarding your trip to the restaurant, unfortunately not too surprising that the women there that showed a positive interest in you all were already involved. It would be way to too simple to find a woman that both appreciated your style, and was available!

[Maximilian]

Great description of you day. Major disappointment that there were no accompanying photos of your session. If you ever go back, you might consider taking your camera, and asking the woman to take pictures of you at various stages her session with you. If you looking to be able to eventually do this yourself, I'd think it would be very helpful.

Regarding your trip to the restaurant, unfortunately not too surprising that the women there that showed a positive interest in you all were already involved. It would be way to too simple to find a woman that both appreciated your style, and was available!

Personally, I would've felt weird asking the saleswomen to take photos of me while getting my makeup done. Women getting their makeup done don't ask that so why would I?

With regard to finding a woman with an open mind to my style + single, they're out there. They might not be plenty of them but all I need is 1.

[mtnsofheels]

Hey Max, Thanks for sharing your story, awesome and exciting for you to find and explore in that area of expression! Mac counters are very friendly for sure and makes one feel very comfortable. Are you hoping to become a regular make up wearer? What eye styles did you end with? Keep exploring, Mtnsofheels

[Maximilian]

Hey Max,

Thanks for sharing your story, awesome and exciting for you to find and explore in that area of expression! Mac counters are very friendly for sure and makes one feel very comfortable. Are you hoping to become a regular make up wearer? What eye styles did you end with?

Keep exploring,

Mtnsofheels

I will definitely try to always wear makeup while dressing in a feminine style. It just looks better in my opinion.

I ended up with a day to day natural style that enhances the eye a bit with some eyeliner and natural colors. For an evening look I like the smoky look yet it's not a very heavy one, more like a 'mysterious stranger' thing.

[Dawn HH]

Maximilian:-) I thooughly enjoyed reading of your adventure into make-up and getting it applied at a store. I often thought that that would be fun for me to try some day. It is just too fussy for me to try to apply to myself and on a day to day basis is out. Steve63130:-) Got any pics available with your Sherwin -Williams make-up applied? TEE! HEE! Cheers--- Dawn HH

[roniheels]

Thank you for sharing your story. I am so glad you're happy with your own personal progress and everything you are experiencing. Please keep sharing your experiences with us and I also loved the photo of you and especially the outfit and heels you are wearing.

[danielp6406]

A long post but it was worthed to "stick to the end" of it.

Like many other, I am very curious to see your made-up look.

Wondering if the look would be like "too much" or not.

And I guess it must be quite amazing looking at that gorgeous woman too.

Are you prepared to deal with all the "fuss" about applying and removing make-up each day ?

(Or maybe your intention is to wear make-up only from time to time ?)

I hear comments from women and they all say they are "tired" about their make-up routine.

But most of them are saying they would not leave home without make-up.

An interesting thread to follow...

[Maximilian]

Like the saleswoman at MAC said, "it takes effort and time to look good". I agree that it does take time putting on/taking off makeup but after seeing the difference between dressing in a feminine style with makeup compared to going out without it, I can honestly say that it makes a big difference. It completes the look, kind of like a painter putting the finishing touches on a painting. My intention is to always try to wear makeup when wearing a feminine style. Yes, the first time I saw myself in a smoky look I thought that it was too much but it grew on me a few minutes later. However, since a feminine style isn't exclusive for me as well as the fact that I spend most of my time out of town working in a job where looking good is the last thing on my mind, applying makeup is far from a daily occurence. Obviously, the next time I post pics, I'll have makeup on. It will be a while though since I'm going on vacation until after Christmas and I'm not planning on wearing a feminine style during that time.