Giving Thanks


It’s that time of year again when the leaves change color and fall, the wind starts to get colder and thanksgiving is upon us again, well at least here in Canada it is. I think in this day and age we really do need to look back at what we have, to keep where you are going in perspective.

I am so thankful for my wife who has put up with all of my habits over the years, from the dressing to all the hobbies and the weird little things I do. She has been by my side no matter what and that pretty much seems to sum up our relationship. It has not been all fun and games, we have had our fair share of downs that were so far down I did not think there was any way back up,  but we came back better than ever.

I am Thankful that our child feels safe enough in our house that they can be themselves. I did a post way back talking about how our child came out as nonbinary and how easy it seemed for them to be able to tell us about how they felt.  The wife and I always made sure to tell our kid that there was nothing they could ever tell us that would change how we felt about them.  We always assured them they were loved and nothing could ever stop us from loving them.

I am thankful that I live in Canada especially with some of the stuff going on in other places in the world today.  For the most part, my rights as a human being are upheld

I am thankful that I was given the opportunity to finally go out and meet someone that shares the same likes as I do.  It was a great experience and I can’t wait to do it again.

It’s not a huge list but just some of the first few things that popped into my head.

I hope all my fellow Canadians have a great Thanksgiving with Family and Friends.

Thanks for reading




My 100th Post, And… I Did A Thing!

100th post

It’s taken me 5 years, but I have finally reached my 100th post on Cynthia’s Crossdresser Journey, and to be quite honest, a journey it has been. When I started this I wasn’t even at the point where I was buying anything for myself nor would I have ever thought I would tell my kid or even meet up with a fellow Crossdresser, but all those have changed in the last 5 years. I now have no issues heading out and buying stuff for myself, my kid knows although I do not dress in front of them and coincidentally my 100th post fell just after I ended up going out and meeting another local CD.

Even I find it hard to believe at times that I have taken the time to write 100 posts, I am by no means a writer and at times find it very hard to make a cohesive narrative about myself but there are a few of my own posts that I do believe I hit the mark on and some of them are…

So before I get into the second half of this post I would just like to thank everyone who has been coming here to read my ramblings for the last 99 posts and has been able to put up with my crap sometime, Thank you very much.

And now onto the 100th Post

So back in A New Adventure, I had talked about going out for coffee with a couple of other local Crossdreser’s, at this point, it has not happened so that’s still up in the air. But at the same time, I was contacting them I was also messaging some other people I used to talk to.

Around 2004/2005 I started talking to the Wife of a local Crossdresser, we ended up meeting in an online group and started chatting. We hit it off pretty quick and we messaged back and forth for quite a long time. Eventually, we did end up meeting her for coffee but at that time her Significant Other could not attend. Fast forward a few years and as it happens life gets busy for everyone. I tried to at least keep in touch once a year just too see how everyone is doing. This year on my yearly email I was telling her how I was trying to get out more and meet more people like myself and she mentioned that her SO had attended a meeting locally and I should email and chat with him (We will call her Shelia). We emailed back and forth for a bit and we decided to head out some night and have a coffee.

I tried to pick a coffee spot that was close to where we both lived so it would be easier to get too, but hopefully not packed to the gills with people. I settled on one that was fairly close to both of us and we set the plans for Friday at 6:00 pm. I was surprisingly calm throughout week although I was getting anxious as the date grew closer. As Friday rolled around my wife started to remind me “Not to be late, you have coffee tonight” numerous times before I headed out in the morning, and luckily work seemed to go almost perfectly well which rarely ever happens especially on a Friday. I headed home, cleaned up and changed out of my work clothes and had a brief sit down, I fugured I needed to head out at about 5:30 but in my haste when hopping into the car I realized it was only 5:17, Oh well lets go anyways I thought. I arrived at the Tim Hortons at 5:30, WAY TO FREAKING EARLY. I found a spot at the end of the parking lot and parked. I scanned the parking lot again and did not see the vehicle Shelia said she would be driving. At this point I am starting to freak out a little bit, What is Shelia dosen’t show up, will we be able to talk, will we get along? not sure if it was the fact that I was nervous or the fact that I had been in the sun all day but I felt like I was on fire. The minutes seems to pass like hours while waiting but Shelia’s vehicle showed up. I got out and greeted Shelia. We headed inside and grabbed a drink and decided to talk out by the road on a bench where there was no one else.

We talked about everything under the sun, home life, spouses and work-life were all topics of conversation. And of course there is no way two Crossdressers could have a conversation without talking about fashion and makeup and I was also able to get some hints on where to pick up some decent forms and wigs as well. We also had some good laughs as well talking about some of our more hilarious dressing related incidents and just funny stuff. All and all I think we both had a good time talking and will be making some plans to head out for coffee again and maybe even a shopping trip

This was a great experience for me and I am so glad I went ahead and did it.

Thaks for reading my 100th post.


Image by from blog post by MatissDzelve from Pixabay

What’s In My Tool Box?


One thing I have for sure learned is that you need the right tools to do a proper job when it comes to makeup. I was once more than happy to use those little sponge applicators that came packaged with eye shadows, I had no idea how much better a decent set of brushes would help with even simple eye looks.

I had had a conversation with a co-worker about her application techniques and she remarked that she never used lip liners and if she did need a nice outline she would only use a lip brush. Up until this point, I had never thought about really spending money on brushes because how much better could it possibly be? Turns out it can get way better. I did some research and dropped about $20.00 on a small brush set that consisted of DSC07334powder, eye shadow, smudge, concealer, and lip brush. I really only wanted the lip brush but the whole kit set me on the right path for bettering my makeup routine. The lip brush did help me outline and define my lips more than just using the bullet but it was when I tried the eye shadow brush that I really learned what the right tools can pull off. No more was my eyes a raccoon-like mask but now I could control the definition between the colors and with the smudge brush I could work the colors into each other, it was literally a game-changer for me.

I don’t spend a ton of money on brushes or tools and a few web searches will give you tons of results for some cheaper brands like E.L.F and Wet N’ Wild, they usually have some pretty decent reviews for their brushes and they are very affordable.


Foundation Sponge.

I started off getting some foundation sponges which are really great to apply foundation in my opinion.


I place a small amount on the back of my hand and with a wet sponge use a stippling motion to apply to my face. If I run out or need to build up the foundation I can simply add more to the back of my hand. I paid 5.00 for a package of 2 at Shoppers Drug Mart.

Foundation Brush.

I have picked up 2 different styles of foundation brushes. The E.L.F. pointed foundation brush and the Still flat brush. I have not yet really had a chance to sit down with these and see if they give me any better results as the sponge does, guess that is an idea for another post.


After watching a few Youtube makeup application videos I decided to pick up a beauty blender (or knock-off) sponge. I mainly use it to blend out my under eye concealer to lighten the area. Regular retail price at Shoppers Drug Mart is 8.00 but I think I picked it up on sale.


These can be used for foundation application as well but I find the I get more coverage from the flat sponge and I really like the pointed end on the blender to do the concealer under my eyes and blend it out.

Eye shadow.

Like I said at the beginning, I used to be happy with the little sponge applicators that came with all the eyeshadows for years (and still do) to apply my eye shadow. It was not until I picked up my first real set of brushes that contained an actual eye brush that I was swayed into spending more on tools. I have picked up a few more sets since then from E.L.F. by way of there Christmas gift sets which usually come with a large assortment of shadows plus at least 2 or 3 brushes. The smaller brushes let you have so much control over how much product you apply or even the thickness of the lines you want, for me, it was truly game-changing when it came to the finished product.


I still have issues with blush as far as control and actual placement of the application.  This brush does a decent job and lets you take control of the amount of product you can apply.



My E.L.F. Contouring brush came packaged with a contouring kit as well,  with 4 colors to define your face. It is a wide thick brush that does require a light hand when picking upDSC07324 the actual product.  The first time I used it I had to take off all my makeup and start again because I went way too heavy-handed in the dark color.



I had seen some videos showing people using fan brushes for highlight application and thought it would be a great idea to try. After some more research though it turns out most people say no to the fan brush. It’s a little too light to really pick up any product.  But this was a gift from the wife so I will try and find a decent use for it.



I have a few very nice and fluffy E.L.F. brushes for my powder application.  I have a total face brush and a powder brush.    The total face brush has a rounded tip to it and the powder brush has a flat top which works for stippling you setting powder onto your face.





The Eco-tools lip brush is a very thin stiff bristle brush perfect for lipstick application. I take it right off the bullet and use the edge of the brush lightly to try and line my lips then using it on the flat I can fill in the entire lip area


then go over them again straight from the bullet. I find this way gives me the best coverage. I wish I was a little better with lipstick,  even with outlining I end up with very small looking lips.  I have tried overlining but then I end up like a clown,  I need to find a happy medium.


Getting ready and Cleaning it all up.

Yeah, I guess these are technically not tools,  but they are also kept near my tools so I will include them.

From left to right:  Olay oil minimizing toner, Olay Complete combination / oily Moisturizer,  Mary Kay eye makeup remover, and Garnier Micellar water makeup remover.


I recently picked up the Toner to use after I shave as when I try to get really close before foundation application I find that the next day I am starting to break out.  I am hoping this will give that extra little clean up after to stop that.  So far I have had the chance to try it once and it did seem to limit the ammount of spots that popped up after shaving.

Olay complete Combination / oily moisturizer is truly great for the price.  It’s amazing that after I use this my face feels so soft,  it even amazes me some time.  Quick to set in and does not leave a greasy feeling,  with a very light scent.

Mary Kay oil-free eye makeup remover does just what it says it does.  It will remove even waterproof makeup and really just peels away the eyeshadow with a couple swipes.

Garnier Micellar water in normal to sensitive skin.  I bought this one a while back and have yet to test it on a whole face full of makeup.  I really wanted this for lipstick alone just in case some of the ones I have are staining.

Not shown are my Olay daily facial clothes which I really like as well.  Not even sure they still make the same ones I have.  I purchased in a double pack and they are so good I usually cut them in half and it still has a ton of cleaning power.


A final note is keeping your brushes clean. These are coming in contact with your skin and can become dirty quite fast. There are literally hundreds of website telling you how to and how often you should be cleaning your brushes and in the long run cleaning them can only increase the length of time you can use them for.

So there you have it, all the brushes I currently use or own. It’s not as huge of a collection as some may have but so far they either all have a purpose of I am still working on using them.

Have you picked up any brushes yet? Do you plan on it? and if you did and have how did you feel when you used them?

Thanks for Reading



The Wish list

Wish List

I was in my mid 30’s before I really accepted my Crossdressing so I really still do have some things now that I am in my early 40’s that I want to cross off my wish list. Over the years I have done a few things I wanted to do and they are…

  • Tell my Spouse
  • Shave my legs
  • Buy clothes and lingerie myself
  • Buy Makeup myself.

But I still have a few left. So here they are in no particular order.

Have my other ear pierced

I have had my left ear pierced for years now with 2 holes. It would be so much easier and nicer looking if I was just to take the leap and get the other ear pierced. The only thing holding me back at this point is the price. Right now the price is the main thing holding me back as having a professional piercing job done cost $40 per hole including hardware the last time I checked. Until the time when I can afford it, I may just pick up a couple of pairs of clip on’s.

Have a professional make over done / Makeup lessons.

Ever since I was a little kid and even before I even knew what a Crossdresser was, I had always been enthralled by makeup. I would always slow down just a little bit walking through the cosmetics department at Sears so I could take it all in.

I think it would be a great experience to be able to get a full makeover done. This is an experience I have always wanted to try just to be able to get some professional pointers and possible help with my own application. I am currently looking into making something like this happen, although at this point I would just like someone to be able to talk with to get more personalized makeup options so I can stop wasting money.

Buy clothes without hiding behind a list.

Yeah I know,  I already go out and buy things on my own,  but if asked I always say I am looking for things for my wife.  To be honest I have only ever been asked if I needed help in the clothing store twice and have been asked way more times in the makeup aisle.  Even though I have measured myself and know my size I have found that even two skirts from the same company and in the same size can fit drastically different.  It would be way easier if I could just ask to try things on to see if it fits properly.  I have contacted the head office for Addition Elle and they say the store is aware and would be accommodating but it’s only my fear and the fact that I don’t want to make other shoppers uncomfortable.

Manicure / Pedicure.

This one made the list,  but not really something I would probably do more than once.  I really do enjoy painting my own toes and making my own fake nails,  but I would like to say I have gone at least once.

Go out dressed

I had decided a long time ago that I never really wanted to go outside dressed, I was too afraid to be noticed as there is no way I am going to blend in at 5’11” in bare feet and over 6 with heels. But after a chat with a former coworker I rethought the whole idea and decided that I would like to go out just once at least to say I have done it. She even suggested that maybe heading to a bigger city like Toronto or Ottawa and head out in one of them.

So that’s my wish list, do you have one of your own?

Please leave it in the comments.

Thanks for reading


A New Adventure.

a new adventure

I have found over the years as I get older I am needing more friends that share my interests when concerned with Crossdressing. I find myself quite lonely not being able to talk to anyone regarding clothes or makeup and as I have stated here many times before, my Wife is not a fan of fashion or makeup and only deals with them on an as-needed basis.

Prior to the Facebook era I was able to find like-minded people online that I would happily chat with for hours about clothes, makeup, and other such things but those chat engines like ICQ, Yahoo, and the likes have all dried up over the years and the last time I tried to visit any of them I was just met with empty “Friends” list. I tried newer sites such as Twitter and Facebook but I found them almost impossible to make any real contact with other humans.  I was kinda getting the feeling I was alone.

Then, while I was off recuperating from an injury, I joined a (Yet Another) CD oriented website like I have many times before. It was a newer one that I had not heard and seemed to have a higher percentage of Canadian Gals than I had seen before. After posting my initial greeting I was told to use the member’s search function to see if there was anyone in my area that I may be able to chat with. After a few searches I found what I was looking for, another Gal that lives in the same area as me, we will call her Joyce. I quickly sent a friend request and a message introducing myself. We messaged back and forth a few times and not much else came of it at the time and I (Like I usually do) stopped going to the site daily.

It had been a few months since I had talked to Joyce so I sent a quick message just to see how she had been doing. It was a few weeks later that I received an answer, she had been busy with summer things and was currently now meeting other CDs in our city. The Gals have been meeting at a local restaurant for coffee and to chat. Joyce then asked if I would like to head out for coffee with them at some point. I was excited at this prospect but also had equal parts doubt’s as well. I told Joyce I appreciated the offer and that I would have to discuss the idea with my wife as well, she was more than agreeable to this.

My wife has always been supportive of my dressing and has said I should get more friends with the same interests but still worries about my safety even though I am 5’11” and built like a linebacker.  I showed her the messages and she encouraged me to head out and meet these ladies if the plans could fall into place,  she said not to chicken out because I would regret it later on.

So here I sit a few days later waiting for an email for a possible coffee date with a few other local Crossdresser,  never thought this would ever happen.  When I find out more I will let you all know.

Thanks For Reading


Build-ups and Let downs.

buildups and letdowns

We have all been there when it comes to Crossdressing, the excitement, and build-up when we think we are going to be able to dress and then the let down when we can’t for whatever reason.

If you’re like me when you find out that you may have some free time that could be used for some dressing your mind starts to swim with all the possibilities.  What you will wear,  how you will do your makeup and what you could possibly do while dressed,  and again if you are like me it’s something you will obsess about from the moment you hear about it. You plan, free up some extra time and have everything ready and then the door gets slammed closed and your free time for dressing is no longer,  and if you have just spent the last 4 or so days thinking about it you can be crushed.

My dressing time is sporadic at best.  Even though the kid knows I dress, I am not comfortable dressing in front of them so it’s only when they go away for the night. With this, all taken into account the only time when I would have the ability to dress up fully would be Saturday.

Below is a recent event.

I was told recently that the Kid would be staying over with a friend on Saturday night, this would work out great. I have not had a complete dressing session since October of 2018.  We completed our Saturday chores around noon and then went to lay down for a short nap, I figured I could start to get ready around 4-ish and then I could stay dressed until around 10 or later. Around 3:30 I went and had my shower and a shave and moisturized my face in preparation for makeup. At this point, it was now closer to about 4:30, still tons of time. I happily sat in the living room discussing what we should have for supper with the wife while applying my nails. We decided on something simple as we are running low on food in the house due to a fridge that’s in its death throes. Once my nails were applied I headed off to the kitchen and made us some sort of noodle dish and we ate dinner while watching COPS (My Wife is addicted to shows like these). Once dinner was finished I rushed off to the bedroom to start getting all my other stuff out of the closet.

In the last few years since we told our Kid about my dressing, it was decided that I did not need to hide my clothes in the back corner of the closet in a box anymore,  so now it’s way easier to just open the closet and reach in a grab my clothes.  I keep all of my dresses, tops and my selection of padded bras hanging up. I pulled my black dressDSC06041 out from last summer and a grey and pink matching bra and panty set for underneath. I slipped into my underwear and popped in my forms and proceeded to have a seat at my desk.  I personally find it easier to do makeup first then finish getting dressed,  that way I am assured I will not splatter foundation, eye shadow or powder all over my black dress. I pulled all my stuff down and started getting it all ready by picking out the colors I wanted and getting my brushes out.  I don’t have a vanity but I do have a computer desk that is just the right height to sit my mirror on. I wetted my sponges and after a few false starts and many, many times trying to get the mirror just in the right position, I applied my foundation to the back of my hand and was just getting my forehead started when from the living room I hear the wife yell “Don’t start your makeup yet!!”

“Well shit, why not?” I yelled. Turns out the Kid did not take all of their needed medications with them to the sleepover and now we had to run them over. That’s when reality hits,  there is no chance at this point that I am going to be able to dress. It’s already 5:30 at this point and it’s going to be well after 6 by the time we get back. I start removing my nails and head off to the bathroom so start getting the foundation off my face.  Luckily I have some decent face wipes that take almost anything off so the foundation clean-up took minimal time and we were off to deliver the meds.  By the time we returned home, it was well after 7 and I still had to put everything away because we had left in such a rush.  I had debated just a dress and some lipstick but it was time to feed and take the dog outside before getting ready for bed.  Yet another dissapointment in the dressing department.

Do you have any stories of losing your time to dress?  how does it affect you?

Thanks for Reading


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.

Thanks for Reading