Thing’s I have learned being a Crossdresser: 4 Years Later

4_years_later

One of my most read blog post’s of all time is Things I have learned being a Crossdresser and as of August 2017 it has reached 1000 views.  I figured seeing as it has reached 1000 a update to the blog with the other things I have learned and where I am today was in order.  I have the original text in black and my new updates in pink.

I have learned so many things in my time as a Cross Dresser.   Dressing up like a woman takes so much skill and patience I am amazed women go through this every day.

1) Clothes

This is the first minefield you should try and cross,  and let me tell you it’s a big one.   Shopping for Men’s clothes is pretty simple as a whole.  Pants, shirt, underwear and socks.  Choose from some of your basic colors like brown, green or blue and you are set.  Women’s clothes on the other hand is a multitude  of colors and fabrics all of which make a completely different look  and statement when worn in the daytime or  night.  I have spent many many hours on the internet looking at clothes and I seem to only have touched the surface of what is out there.

I have expanded my wardrobe over the last 4 years with lots of new stuff that I never thought I would have worn before.  From long dresses, shorter skirts and sheer lace tops.  I was lucky enough to get a female friend that was very helpful in the fashion department.  I would regularly send her pictures of something I wanted to buy and get her opinions of what should or could be matched with the said item.   My best idea now is just to buy stuff that I like and think will be fun to wear.

We also cannot forget the base to any good outfit, The Lingerie.  My Lingerie drawer has expanded with my wardrobe to incorporate many more pieces.  Sometimes you will want to wear a top that has a low collar and you need a lower cut bra that cannot be seen in the collar of the top.

2) Skin care and Make up

Again, another minefield.  I feel that cosmetics as a whole is one of the most confusing things to learn as a Cross Dresser,  clothes can be figured out but to truly learn how to pick the colors that suit you and learn to apply said colors really takes practice.  Make up sections in most stores are fairly big,  at least 4 to 5 isles.  This is where will usually find,  make up,  nail polish and supplies, fragrance and various other beauty tools (brushes, sponges, etc).  I remember the first time I went to purchase some make up with my wife.  I was so nervous the whole time I just pointed at some stuff and did not really pay attention as to what colours I was getting.  Well after my first attempt at using said colours I looked like a clown and not even a funny clown,  more like a horror movie clown.  There are lots of website that give hints and tips for finding the right matches for your skin tone and skin type.  Another good option would be to consult your local stores or salons to see if they are CD friendly and have some help learning.  Most places will give lessons if you buy a specific amount of product.

I wish I would have not used the term “Minefield” once let alone twice,  Oh well.  You live and learn.

I would  like to say that I was awesome at applying my make up,  But I am only slightly better than I was four years ago.  It’s hard to to practise on make up when it’s such a time consuming thing to work on.  There is the shaving,  moisturising and so on and so forth.  I like to have at least a good 2 to 3 hours for a make up practise session because I know at least 3 times I will have to start all over again.

I am still trying to find the right shade of foundation without any luck.  I have spent more on foundation than any other make up product.  I am currently looking into getting a appointment the local MAC store to get matched.  Apparently the store here has a good reputation from the local community but they do not have a private room so I would have my appointment right out in the front of the store,  I am sure I am not ready for that yet.

I have given up on trying to only find “The Right Colours” for me.  Instead I buy whatever colours I want to try and have fun with.  My lipstick and eye colour choices have not gone extreme in any way but I am for sure going for brighter red and pinks and so far they look pretty good.  As far as skin care I am still pretty relaxed about it only paying attention to my skin just before I get ready to apply my make up.

3) Shaving your legs

I am positive every woman is a contortionist with a perfect sense of balance and eyes like a hawk.  I can’t seem to shave my legs without missing a huge area of hair,  not being able to see some areas at all or almost falling over and killing myself.    My wife was nice enough to teach me how to shave my legs years ago.  I say shave but the first time was more like clearing a forest,  and I ran out of hot water in the shower TWICE,  it was well over a hour experience.  Now I only shave in the winter months which is when Cynthia wants to come out more and the fact that I don’t want to tell people why I shave my legs.  I know most people will not believe I am a Olympic swimmer or cyclist.

Practise makes better,  But I am still not perfect.  Once the weather turns cold in early fall I start shaving my legs and that first trim is the hardest part in my opinion and takes the longest amount of time.  It really helps to have a well lit shower and at least the edge of the tub to prop your foot up on.  Remember to use lots of shave gel and a decent razor.  I find it’s best to completely wash and get your hair done,  That way your leg hair will be softer from the hot water and easier to cut.  I get quite a few shaves from my current razor and I am usually shaving my legs at least every 2 to 3 days otherwise I end up with tons of little ingrown hairs..  If you have really coarse leg hair you may need to change your blades more often to prevent razor burn and ingrown hairs.

Since I posted this I also have started shaving my chest in the winter months as well.  There is nothing worse than having a nice lower cut top and passing a mirror and seeing all those chest hairs poking out from a really nice top.  I tried little straps that attached to a bra that would mimic the top of a cami,  they are OK but just not the look I wanted to go for.  So for the first time last winter I shaved my chest and tried to make some cleavage.  Did not go as well as some things I found on the internet but at least it looked better.  The chest area does get super itchy when the little hairs grow back in,  it almost drove me crazy.

4) Your Significant Other

If you are as lucky as me to have a wife or girlfriend who can accept your feminine side you are in a good place.  Also you are in a place to loose many things.  I cannot count how much stuff I have lost to my wife over the years.  Everything from make up to blouses.  Seems she uses it once and it ends up in her regular rotation.

I am so lucky that my Wife puts up with me even after all these years.  I know at times I was very annoying when it came to either talking about dressing or wanting her to take me shopping that I am sure at times she wished the Crossdressing would just go away.  I think I have mellowed over the years and now that I can go out and just buy my own stuff makes it a lot easier on her,  although she does still like a good shopping spree every now and then.

5) Nail Polish

Looks easy doesn’t it?  That is until you try it for yourself.  When you watch a video on Youtube the brush strokes seem oh so easy until you try to replicate it and you end up using more nail polish remover than nail polish.   Similar to make up,  Nail polish requires time to learn how to do it properly.

I gave up on painting my own natural finger nails,  way to much work only to have to take it off either that night or the next morning.  I could never get good with painting my right hand nails with my left hand.  I went and bought large sized acrylic nails and made myself quite a few sets.  The great thing with the fake nails and tip stickers it that the nails can be removed and used over and over again.  It’s also a way easier way to experiment with nail ideas.  The fake nails are fairly easy to cut and shape in any way you want then paint and with the price they will not break the bank doing so.  I did a kinda tutorial that you can read here.

I have learned how to paint my toenails decently well and I tend to keep them painted from fall right back into spring.  I use Nina Ultra Pro nail polish from Sally beauty that has a wider than normal brush.

6) Pantyhose on wet legs

You may as well fight a Polar bear because you have about the same odds at winning that fight as you do getting a pair of pantyhose up damp legs.  It’s damn near impossible to pull them up and at the same time you have to be super careful not to put a run in them or all your hard work just went down the drain.  Take a hint from me wait till you are totally dry or invest in thigh highs.

Still can’t get pantyhose on wet legs,  But I did get pantyhose on with my fake nails already done and didn’t put a run in them so that’s a WIN.

Well that’s all I can think of for now,  I am sure  I will think up some more.

And for those of you that do read my blog till the end I appreciate that you can make it through basically what amounts to ranting on for what seem like forever.

So that’s my 4 years later update.  I got some wins and some things that I still need to work on.  Crossdressing is ever evolving.

Thanks

Cynthia

 

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2 thoughts on “Thing’s I have learned being a Crossdresser: 4 Years Later

  1. Oh good grief, I think the internet demons ate my previous response. I just popped by to read your blog after you tweeted at me (re: Halloween candy!). I really loved this post! So much of it made me smile and hearing that your wife is so accepting. 🙂

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