Six key questions to ask yourself to help you determine where you really are at with your cross dressing

So reading up around the internet trying to get some inspiration for new blog posts I came across this article
“Six key questions to ask yourself to help you determine where you really are at with your cross-dressing.” I decided to try and answer them myself and use this to add some more back story to myself and maybe some insight as to where I am going.

Do you still crossdress to the same extent as you did when you first started?

Not even remotely. Years ago when I started dressing I could not even look in the mirror, the moment I saw my reflection I was horrified with the person staring back at me and then the moment would be over. I would try to push these feeling I had way back down and try to keep a lid on them for as long as possible. With time and help from my wife, I was finally able to accept this part of me and try and explore it more. I now have no issues with my reflection.

How does the quantity of female clothes (from En Femme or other sources) you own relate to the number of male clothes you possess?

My female wardrobe is smaller or maybe equal to my male side.  I have never done a side by side comparison of the 2 sides of my closet.   

Cosmetic surgery to make you feel and look more feminine?

I would never undertake any type of cosmetic surgery unless it was necessary. I am happy with my looks as are and can always feminize with makeup.

Comparatively, do you spend more time crossdressed or think more about crossdressing than you did, say, 3 years ago?

In the past, I could go years without even thinking of dressing.  I would need to dress for a bit then the urge would fade away a bit which was also due to self-esteem issues.  I find now that the urge is always there and I pretty much think about it daily,  although I don’t need to act on it and hopefully don’t bother my wife about it as much.

Have you gradually been breaking your own personal taboos such as vowing never to go out of the house crossdressed or going out in daylight rather than only at night?

The summer of 2018 I was granted the opportunity to dress whenever I wanted to for almost 3 months. I took this time to dress for hours at a time and even decided that I was going to take the plunge and head outside during the daylight hours. It was a great time and I would love to be able to do this again.  I would love to be able to head out at least once dressed still.

Have you ever plotted a short holiday or vacation to spend a few days or even a week en-femme?

Although it would be nice I have never been in a financial situation that would ever allow this type of holiday. Maybe someday though.

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It Takes How Long?

So I am still at home recuperating from an injury a few months ago, and I am now to the point where I could dress if I had the time to. According to my wife I have almost 8 hours after the kid leaves for school in which to dress, But how much time does that really give you. That got me onto the question of how much time does it really take me to get ready?

So my best guess, worst case estimated times for how long it takes me to get ready are

  • 1 hour – To pick out clothes / set up
  • 1/2 to 1 hour – Showering
  • 1/2 hour – To shave my face.
  • 1/2 to 3/4 hour – Nail application.
  • 1/2 or 1 hour for makeup prep and application.
  • 15 minutes to get dressed.

So lets break this down a bit further.

Picking Out Clothes / Set Up.

One hour to pick out all the clothes I will be wearing. I could do less but if I am taking some pictures it is way easier to have everything out and have it all hanging up to be swapped out between pictures. Our closet is very small and I only have a handful of items hanging up so most of my clothes are still packed into totes so everything has to be removed so I can find what I am looking for. Plus I also at this time try to get the camera and tripod all set up so all I have to do is either drag it outside or have it already to go inside.


Half hour to a full hour depending on if I have already shaved my legs. The first time is the hardest due to the fact that I have not shaved my legs for at least 6 months. I stand in the shower for quite awhile to give the hairs time to soften and then with at least 3 brand new razors and a ton of shaving gel I get to the point where I can use a final new razor to clean up all the stragglers.


Half hour dedicated to shaving my face very slowly and carefully as to clean up all the stubble I can find. I don’t really have a favourite type of razor for this as I usually have to pick out the cheapest razors at the time but for the most part I prefer multi blade razors with the aloe strip so my face is not shredded. I shave at least twice to make sure I have everything cleaned up because there is nothing worse than your foundation sponge getting caught on left over stubble. After my face has had a chance to calm down I apply my moisturiser so it has lots of time to set in.


Half to Three quarters of an hour for Nail application. I never paint my own nails because I am terrible with my non dominant hand and my natural nails are always in bad shape due to my work. I take the time and make my own fake nails which I can then wear with just some 2 sided tape and remove at the end of the night and then use again. With fake nails I don’t have to worry about trying to grow out my own and I can make multiple pairs all with different lengths and shapes. Worst part about application is cutting the proper shapes for each nail then trying to get the protective tape off the back and then applying each nail so it looks straight hence the larger amount of time allocated for this task.

Makeup prep and Application.

Three quarters to one hour to set-up and apply makeup. I really like to sit down and take the time to apply my makeup. I take a bit to get all of my products set out along with all the brushes and tools I will be using. Then it`s down to the business of starting application. Foundation has to be built up and concealer added to brighten the eye area. Eyeshadow takes me the longest to make sure both eyes look somewhat the same, and depending on what look I am trying to achieve. I also try my best with my eye liner but as of yet not attained a job that I am ready to say I am happy with. My lips have to be lined out with a brush or liner and try to make my lips look bigger and then filled with the brush and then right from the tube. Moving onto some blush and trying my best to contour then finishing it all off with some highlighter.

So really the only time if would take me the almost four full hours to get dressed would be if I had not dressed for awhile and was taking picture’s. I don’t have to spend an hour to pick out clothes and match them and I could get dressed easier if I hold my nails off till after getting dressed. If I knocked off a fewer of the higher times off I could probably get it down to two hours and fifteen minutes which seems decent and was probably my average last summer. I am sure now that I am able and do have some extra time there will be some dressing in the near future but there are no plans as of yet. Maybe with some luck I can get the wife to help me with some pictures.

So how long does it take you to get ready? Do you have any methods that can cut your time down? Let me know in the comments.

Thanks for reading

Revlon Lipstick Collection.

So staying on the topic of makeup for a few more posts, I thought I would go through my Revlon Lipstick collection and tell you what colors and finishes I currently have. I was prompted to try out the Revlon Super Lustrous Lipstick after finding them on sale for $4.99(Cnd) so at that price, it did not hurt to try. I really liked the feel and finish so I bought a whole bunch more. I would like to say all of the colors I bought were perfect but you know that would not be true

I don’t recall the first one I bought was but I was impressed, So far the only one I really don’t like is Plum Velour which has sheer coverage. I have very small lips and was never able to get them to look right even when overdrawing my natural lip line. As of writing this I still have not been able to use the Show Stopper color yet but seeing as I still have some free time I think I may be able to fit it in soon (I hope).

Another great thing is they have windows in the lid which makes it easier to see what color you are reaching for, except on the Matte versions. I like this idea even though I keep all mine with the label facing up so I can read the names.

One last thing I have to say about these is that I really love the presentation on Love is On. The packaging reminds me of higher-end brands and with the color and writing on the inner tube, it just looks really fancy to me.

027 – Violet Frenzy – Pearl

051 – Red Rules The Word – Matte

052 – Show Stopper – Matte

053 – So Lit! – Matte

435 – Love That Pink – Creme

657 – Fuchsia Fusion – Pearl

720 – Fire & Ice – Creme

740 – Certainly Red – Creme

745 – Love Is On – Creme

850 – Plum Velour – Sheer

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Yet another Makeup Purchase.

So after Christmas and before my accident I had been able to pick up some new makeup. I was hoping for some quiet time after the holidays were over but things did not turn out like that. But I guess I can post up the new makeup I was able to get. The pictures are not the greatest because I was not able to walk around the house to get the best light for the pictures.

Just a little after Christmas I found some of the E.L.F. Holiday kits on sale at the local drug store for 60% off. I grabbed a new 48 color Eyeshadow kit that came with eyeshadow and blending brushes which themselves would be well worth the price I paid for it. Not sure I will even use the eyeshadows since I have barely been able to even use half of the colors from the last E.L.F. set I bought last year so I may give this to my wife and keep the brushes for myself as she has a decent set of brushes. I was super happy with the set of eye brushes I picked up last holiday season. It’s amazing how much more detail and control you can have using the right tools for the job instead of the crappy little sponge applicators you normally get with eyeshadow.

The second kit I picked up was an E.L.F. Contouring kit that also came packaged with a nice wide brush for application. I started some practase last summer using contouring and I really liked how it looked. The brush that came with this kit seems like it will be a real help seeing it’s a thick wide shape to help.

Maybelline products have been high on my lists recently because I tried there Matte+Poreless foundation and I was amazed at how it felt, the coverage and even how it looked in pictures too. I have tried some of their lipstick, mascara, eyeliner and highlighting kits all which I am so far really liking. So when I first saw the adverts for their new Color Sensational Made For All lipstick shades I knew I had to pick up a few. More specifically Red For Me and Ruby For Me seeing as I have been going for more vibrant reds lately. I am really happy with other Color Sensational lipsticks I have and am hoping these ones are just as good.

Red For Me is a Matte red and the Ruby For Me has a great sheen too it from what I have seen in ads and videos on the net. All the new cases have a similar color as the lipstick inside with a matte finish on the Red For Me. I have yet to try these but I am hoping that sometime soon I will be able to sit down and try all this new stuff seeing as with my injury I am going to be off my feet for a bit longer while everything heals.

Thanks for Reading.

Update 2019

2018 ended on some high notes and 2019 seemed to be going fairly well, until recently.

Starting off 2019 with a Break

A few weeks ago I was in an accident that required an emergency visit to the hospital via an ambulance. I had called the wife to tell her to meet me at the ER and as I was talking to her I realized that I had painted my toenails a very bright sparkly red just recently as well as shaved my legs. This has always been a fear of mine and one of the main reasons I never, ever underdress at work. The fear hit me as I was talking to my wife about the toes, She said we could tell everybody that our kid had painted them. This option made me feel a little bit better. Fast forward to the hospital and sitting in the ER waiting room for what seemed like days and I was finally ushered into the back and up onto a hospital bed, I knew the moment of truth was to be soon. Doctors and nurses swarmed around me and I was told the socks would have to come off. There, in all there red sparkly glory were my nails, and not a word was said. It was only after the initial check was done that a nurse finally commented on how nice they looked and who had done them for me. I was then pushed all over the ER from room to room as I needed X-rays and other tests with my bright red toenails entering the room before I.

I was ushered into surgery the next day and was temporarily fixed up and spent the next 4 days laying in a room getting ready to go home and wait for the surgery to actually fix the problem, all the while with my toenails out for the entire ward, nurses and doctor to see. Of course I did not spill the beans and let out all my secrets, but still, I did not hide them either. It’s 2019 world and I can damn well have pretty nails too.

In appreciation of my Wife

My wife and I have been together for over 22 years between dating and marriage and to this day I am not sure how I lucked out and found the love of my life, A person that is truly kind, helpful and loving to the highest degree. If you remember way back when I posted a blog from a letter my Wife had sent to me titled Wifey’s point of View you would remember we have been through some pretty dark times and always come through the other side a little bit better. It’s dawned on me now after my accident even more how much my wife has done for me over the years and how much she does now. When I came home from the hospital I was pretty much useless, not able to get around very well, bound to a chair and unable to stand long enough to feed myself, and she was there for me the whole time. The worst part about this was she was just getting over some medical issues herself and this did not help at all. She was tired, stressed and still a bit sick but she was there for me. And I feel like a total ass at this point because most of the things I did around the house I now cannot do so I have to watch my poor wife struggle and do it. And through her aches and pain’s she does without even a argument

Dear, you are the greatest.

So it looks like I will have quite a bit of time for this injury to heal and with that time I was hoping I would get some more blog posts in. I am pretty sure my dressing for this season is over but recently I did purchase a new E.L.F. Holiday Contouring kit and picked up 2 of the new Maybelline Made For Me lipsticks in Red for Me and Ruby for Me. I am hoping that sooner than later I will be able to post my view’s on these.

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Getting over my Shopping Fears.

shopping fears

While browsing through the makeup aisle recently,  I thought about how long it has taken me to get to the point where I am comfortable enough on my own to head into the store and look at and buy whatever makeup or clothes I want.  It’s been about 20 years since I bought my first items of makeup with my Wife’s (Then Girlfriend) help.  Since then it’s been a long trip learning how to shop for makeup and clothes by myself.  It took me a long time to bring my confidence level up to the point where I am able to head out and shop on my own which I think is better for both of us,  don’t get me wrong I love shopping with the wife but when shopping for Cynthia it can be stressful.  My wife does not wear a lot of makeup to begin with so she does not really enjoy browsing.

I can still recall like yesterday how our first trip went.  After telling the wife about Cynthia I had asked if she would help me pick up some makeup.   She agreed and we headed to the local Wal-Mart.   I can remember sitting on the car waiting to go in and shaking like a leaf I was so stressed out.  I wanted the entire Covergirl Fall line at that time but I was not able to afford it.  We were both a little nervous about the whole situation and just wanted to get in and out as fast as possible.  Some bad choices were made,  but we were young and it was a learning experience.

Shopping trips went on like this for years,   heading into stores with a vague idea of what I wanted or needed with the wife quietly asking me questions.  This caused the wife much stress as she was always worried that someone would overhear that our purchases were not for her, but me.  I admit I was worried about this as well back then,  but that faded.

It took a long time for me to reach the F**K it moment and realize that no one cares what you are buying,  they just want to go home.  It was also getting annoying for the wife to have to go out and help every time I wanted something new from the stores,  and I can totally agree with that.  I am not going to lie,  It was so easy for me to drop into a pink fog,  it was not even funny.  I cannot even imagine what it was like living with me at those times.

It was the perfect storm that helped me get off my ass and over my fears.  Firstly one of my favorite stores was having a 70% off sale which meant I could get the bra set I had my eyes on,  and only for about 17 dollars.  Secondly the wife was sick at the time and was in no shape to be heading out in the crappy January weather.  I knew it was now or never,  I checked online and made sure the items I wanted were still in stock in store,  I made my list and waited till I was done work and headed off to Addition Elle.  I did have a friend who offered to take me as well,  but I knew if I did not do this on my own now I never would.

With list in hand, I sat in the car for at least a good 10 minutes waiting for the store to look a little more empty.  When it looked quiet I headed in and straight up to a sales assistant at the front counter and asked for some help getting some presents for my wife,  she was more than willing to help and thought my list was a great idea.  I am sure while talking to her I was as red as a beet but she either didn’t notice or didn’t care.  In no time she had found 3 of the 4 items I really wanted and was ever so helpful in finding something very close to the last one I wanted.  I paid my bill and left the store with my purchases and felt as high as the clouds that I had done this myself.

Of course, once I had completed this task it just seemed to get easier and easier.  Soon I was not even taking a list in with me,  just walking in and heading right over to the sale racks,  looking through and grabbing what I wanted.  Not more mention of buying for my wife because no one ever asked me,  no one really seemed to care as long as I paid and went on my way.  It was true about what they said,  SA’s don’t care (at least from my experience) what the purpose of your visit as long as you be courteous,  pay and leave.

It was not long before I was applying my new-found courage to the makeup aisle as well,  taking my list along with me if I was ever asked if I needed help.  A list is a must have for the makeup aisle just because of the sheer number of brands and products available.  I have been approached only about 3 times while browsing for makeup.  The worst part was going through the checkout and I was sure the lady scanning was going to look up and see who was purchasing the foundation.  Not once did she look up from her task of scanning my items to verify if it was a male or female buying the items.

This post is not a damnation of people who feel they can’t go out and buy for themselves yet.  I was in your heels at one time and I know exactly how you feel.  You may never become comfortable enough go out and get stuff on your own and that’s completely fine.  So many more options are around you could buy everything you ever need and not talk to another human being.

Some tips I have.

  • Do make a list.  Some clothing store websites have the option to check stock,  but it might only be updated every 24 hours.  Make sure you have some backup pieces if needed.
  • Pick stores with self-checkouts.  This can limit your needed interaction with clerks if this makes you nervous.
  • Take proper measurement to reduce returns.  If you are not going to be trying clothes on you will want to make sure you get the proper size.
  • Read reviews before buying products.  I find Makeupalley is great for this as it’s all people who have brought the product.
  • Don’t break your bank,  pick a few items you need and just get those.

When it comes down to it no matter why you are Crossdressing it should be fun and exciting and shopping is just part of it.


Thanks for reading



Oh, Happy Autumn. Fall 2018


Normally I never start dressing until at least late October,  but this year I was given the opportunity to start in August,  a very hot August.

The summer here in South Eastern Ontario was brutally hot,  so even though I had the opportunity to dress,  it was too sweltering to do so most times.   I tried,  I really tried to dress on some of the warm days not wanting to waste the time that I had,  but in 25-degree heat,  I was sweating again after even having a cold shower and foundation does not apply well at all on a sweaty face.

But now that fall is starting to creep in and the days and nights are getting cooler it’s way better.  And with the extra time I have had in this seasonal transition period I have been heading out of doors for some better picture taking.  I was able to head out last weekend and get some pictures of myself in the beginning of the layering/sweater weather season.

I started with working on my makeup,  using mostly products from the Maybelline Fit Me lines I have been picking up.  I am really,  really loving the Fit Me Matte + Poreless foundation in Buff Beige (130).  The coverage is awesome and the match is what I have been dreaming of.  I was also trying out the Maybelline Master Blush Color and Highlight kit. img_20180922_100255.jpg This is the first time I have really used a highlighter and I really liked how it turned out,  just an extra little POP.

For my lips, I used some Maybelline Color Sensation lipstick in IMG_20180822_182417Blissful Berry (410),   it’s a gorgeous berry shade but does not really show up great because my cameras are not the greatest.  I spent a lot of extra time on my eyes this time and used my Covergirl Trunaked Dazed palette IMG_20180826_135033which has some really striking colors in it if you are trying to make a statement.



So after I had my makeup all done I decided to start casual with just a pair of jeans and a few tops and get a bit dressier from there.  The first top is longer with slits on both sides.  It’s hard to tell from the pictures but it has a red metallic thread woven throughout the top which gives it a really nice look.


I first tried A infinity sweater.  I think these were popular about 5-6 years ago but I have not seen any recently.  It looked okay, but with the ammount of extra fabric this piece has it’s probably easier just to get a basic top and a scarf.


I then moved onto a knee length cardigan which I think is my favorite look of all.  I love how this sweater trails behind you in the wind when you walk.  With the extra large holes in the knit,  I doubt it would be the warmest but it lookes nice.

I changed from the shimmery top to a sleeveless wrap top with a ruffle.  This is more of a summer top but with the right sweater it could be a bright pick me up into the cooler fall.  I paired it with a black ruffled bolero.

I moved on from the tops and pants and tried a dress that I had purchased back at the start of 2016 but have not worn a lot.  It’s long sleeved,  so it’s perfect for cooler weather and the fabric is a bit heavier.  It has a slit up the leg on the left side.  With the long sleeves I would not wear a sweater with this but I may try and pick up a shawl to go along with it

So there are some of my fall picks.  I am sure as the weather gets cooler andI still have some decent time outside I will have some more posts to throw up.


Thanks for reading