2023 has been a really interesting year for me. I’m not going to get into great detail but suffice to say there has not been a lot of extra time for dressing at all. In this whole year, I have only had the time to dress up about 3 times completely.
I am hoping that as we finish 2023 and usher in 2024 things will start to get a little more normal around here but unfortunately, I cannot see into the future.
I am hoping that my long-time readers are all doing okay and that you all have a great Holiday season, and hopefully, there will be more to read from me in the New Year.
It’s been a while since I have been around, no real presence on social media, and not even window shopping for anything femme.
Generally, by this time, I would have already shaved my legs and been dressed at least twice but not this year. For some reason, I am just not feeling it yet.
Right now there is just way too much going on in my life for me to take the actual time that I need to do things right. Maybe soon but right now, Nada.
Hello my lovely readers, I hope you are all doing great. I have come back from my hiatus with a story of a well-spent Saturday night.
Last weekend I was graced with the time to get some dressing time, but I also had to head out early in the morning to give my Mother-in-law a hand at getting her some groceries. I waited to head out with the M-I-L until I knew all the stores we had to go to would be open so we could make one big round trip through the city. Once we had completed our trip to the hardware, grocery store, and mall I delivered her back to her house and headed home.
Once home before I could even think about dressing I needed to get a couple loads of laundry done and hung up to dry. Once my laundry was done I was feeling a little tired and headed to lay down for a short nap. I figured I would only sleep in till about 1:00, but low and behold nature thought otherwise and I napped until 2:30.
After jumping out of bed I headed to the bathroom and started to prep for my shower. I have used a combination of shaving and delapitory for my chest since early April and have not really been happy with either. Shaving leaves small hair in the center of my chest that no matter how many strokes with the blade I can never get and I always break out in little ingrown hairs afterward. The delapitory on the other hand seems to leave a smooth surface if I use enough but literally by the end of the afternoon I can feel the small hairs peaking out again, I don’t think there is gonna be a real win for me in this situation unless I use a waxing method.
I proceeded to shave my face while I waited for the delapitory to do most of its work before hopping into the shower and finishing my legs in the process.
I was so behind at this point I had not even pulled anything out of the closet to wear nor pulled my makeup and mirror down from the shelf. At this point, I was running around like crazy trying to figure out what I was doing. From the closet to the makeup shelf and back and forth to the living room where I set up my impromptu make vanity forgetting things along the way.
When I finally figured out what my plan was and had all the makeup in the living room I decided to just sit down and get to work on that and then I would pick out an outfit. Our apartment has some of the worst lighting in the world and really no matter what room I pick it’s terrible. My mirror is an older magnifying style with an old incandescent light bulb inside that put out the most horrid yellowish tint you can imagine, but at least in the living room, I can turn on some of the other lamps and try and make up for all of the shadows I get.
Once I thought I had enough light I started into my long makeup application, it takes quite a bit of time for me to make this face somewhat feminine. Loads of foundation are needed to try and cover the pores and keep the 5 o’clock shadow from peaking through. The best foundation I have found for this is Maybelline Fit Me Matte+Poreless foundation. I have not had a chance to try many other foundations but this one really works for me.
Once my foundation was completed It was time to move on to my eyes. I have so many eyeshadow palettes that I have yet to use it makes for a hard decision, so many colors and so little time. Once I had pulled some out I decided to use a combination of 2 Maybelline palettes, the Matte Bar and the Burgundy bar.
With my poor eyesight and unsteady hands, I started by using one of the matte shades for the base and then moved on to some of the more vibrant sparkly colors for the crease and lids. I can never take pictures of my eye looks as they always look terrible with my camera but I don’t think they turned out that bad.
I stayed away from eyeliner this attempt because I never had luck with it at all but I did manage to get a perfect coat of mascara without getting it all over my eyelids so I took that as a win.
I finished up with my blush, and highlighter, and capped it all off with a light dusting of translucent powder before taking one last look in the mirror and being quite pleased with myself headed decided it was time to do my last step which I normally have huge issues with, my lips.
I headed back to the bedroom and tried to find a really nice red I had not used often before, I wanted something a little bolder. I finally decided on a Matte red lipstick from the Maybelline Made For Me collection and paired it with a similar color liner. I had been trying to prep for this for a few days making sure to take some extra care of my lips leading up to Saturday with some exfoliation and extra moisturization to make sure they were as good as they could get.
I proceeded with the liner and to my surprise stayed fairly even and true.
I Filled in my lips with the liner before giving at least 2 nice coats of the matte red right from the bullet, I was pleasantly pleased with how they turned out in the mirror, easily some of my best work to date.
One last look in the bathroom mirror and I was happy with my makeup and headed off to the closet to pick a couple of outfits.
My initial plan for the day was to be able to get dressed up and take some pictures in a few different outfits. I headed into the closet and picked out a rarely-worn velvet dress I bought a few years ago. I figured I could just come up with something else after I had taken some pictures in this.
The Dress I wanted to wear.
I went back to the living room with my jewelry and nails in hand and picked out a nice pair of purple ones and started to apply them. This is possibly one of the hard parts of my dressing routine. I have found over the years the best way to keep the nails set for the night is to clean all of my nails with nail polish remover to get the natural oils off, this makes the 2-sided tape adhere so much better and I don’t have as many lost nails. The cutting and application of the 2-sided tape can be a pain but not as much as trying to remove the protective cover and then adding the nails, with each nail added my dexterity in removing the cover gets a little worse and worse, but I finally got them done.
After I had completed my nails and jewelry I again headed back to the bedroom to get into my dress. I had recently tried to clean and comb out my wig as it was starting to look a little haggard from being knocked off the shelf so many times by the cat trying to get up there. I put it on and tried to adjust it so it looked good but no matter how I tried it, I was just met with a horrid-looking mess. I tried for a good 10 minutes messing with the bangs and trying to get the side to settle down but I knew at that point I was going to require some extra time.
Instead of staying in my dress, I switched into a comfy pair of jeans and a nice black blouse. I was able to calm the wig down enough that it looked more like I was just in a slight breeze instead of the hurricane it had looked before. I got a handful of pictures which still makes it worth it.
So with all the main excitement out of the way, I settled down into the comfiest chair in the living room, put my legs up, and started some Netflix. Around 7:00 I finally decided it was time to get something to eat and I made myself a nice big plate of Poutine and watched some more movies.
Then the worst part of the day came when it was time to clean everything up. I have used the same eye makeup remover from Mary Kay for years and other than it irritating my eyes a bit, it does remove almost everything within a couple of swipes on a cotton round.
Once my makeup was removed my face moisturized again I could make sure all the other baubles of dressing were put back into their place and I was now safe to slip into bed.
So, apparently I had this finished post way back in October of 2020 and must have forgotten about it.
Maybelline is one of the other few lipsticks I have tried over the years and really liked. They have a decent amount of colors and finishes to suit everyone and if picked up in sale, won’t break the bank. Here in Canada they seem to retail for about $11.99 but I always wait till they go on sale for $6.99 or lower before I pick them up.
From my experience they do not feel heavy on the lips and for the most part have decent coverage. Out of all the ones I tried the only ones I was not really impressed with was the 100 Magenta Affair or 166 Copper Charge. I really, REALLY wanted the Copper Charge to look good but I could just not make it look right.
1. 100 Magenta Affair – Shine
2. 166 Copper Charge – Cream
3. 200 Rose Embrace – Cream
4. 211 Rosey Risk – Cream
5. 222 Flush Punch – Cream
6. 233 Pink Pose – Cream
7. 244 Pink Score – Cream
8. 266 Pink Thrill – Cream
9. 311 Crimson Race – Cream
10. 322 Wine Rush – Cream
11. 333 Hot Chase – Cream
12. 344 Coral Rise – Cream
13. 379 Fuchsia For Me – Cream
14. 382 Red For Me – Matte
15. 385 Ruby For Me – Cream
16. 388 Plum For Me – Cream
17. 410 Blissful Berry – Cream
18. 435 Plum Perfect – Cream
19. 625 Are You Red-dy – Cream
20. 635 Very Cherry – Cream
21. 645 Red Revival – Cream
22. 665 Lust For Blush – Matte
23. 670 Ravishing Rose – Matte
24. 691 Rich Ruby – Matte
So there is my Maybelline Lipstick Collection in it’s entirety. Not sure how my readers will feel about this but it at least gives me something along the lines of dressing to think about other than dressing itself. I hope you guys don’t get too bored of this format for a bit.
Just a little note to let you know I am still around although not doing a lot here. I have not dressed since my last post way back in March, just way too much stuff going on around here, it’s sometimes hard to find the time.
Between dealing with family appointments, stuff for my Mother-In-Law and making sure we have been double vaccinated, there is not much spare time left in the week. any time I do get some spare time it’s spent cleaning of relaxing doing nothing.
We have had a break in some of the heat here though so maybe soon it will be time for Cynthia to come out for a night.
25,228,800 seconds since the last time I was able to dress, here is a little back story.
After the first lockdown here in Ontario, we ended up letting our kid’s partner move in with us as his home life was not going great at the time. Sometime around July, he moved in with us and there were some massive changes for all of us. I had the little things I could do like shave my legs and underdress but that was about it, even trying to paint my toenails was like undertaking a marathon and let’s not even get into the fact about people not knocking before entering a bedroom.
But after the last few months, he started talking with his parents, and recently he moved back in with them. Of course after so long of not dressing all I could think about was dressing again, just one problem, I have never actually dressed in front of my kid, and seeing as our numbers are yet again going back up around here there no chance they would be going out for the night any time soon.
Our kid has offered before to hide out in their bedroom so I would have the space to dress but I would rather not dress than have the kid stuck in their room. So I ran it past the wife about asking the kid how they would feel seeing me dressed, she said it was a good idea.
A little more back story on our kid, they were born female but came out as gender fluid sometime in 2016. I had always said that I would never tell any of our children about my dressing, it is a major part of me but I didn’t feel it was a secret that I would burden my kids with. Coming back to 2016 and our kid coming out, the wife and I decided that it may now be a good idea to tell the kid so they did not think they were alone in the world although I don’t identify as gender-fluid, to be quite honest I don’t really know how I do identify, that’s for another post.
Back to the story.
I decided that I would talk to the kid that night, but sometimes best-laid plans don’t go so well. Maybe it was because I had psyched myself up for the entire day but Friday night I could not bring myself to ask them at all, I decided to try again Saturday. After doing some running on Saturday I was playing some video games while the kid was doing some art beside me and I just blurted out and asked if they would be okay seeing me dressed, their answer was as I expected, a “YES”.
The blouse I was wearing. My literal favorite top!
The rest of the day was fairly boring, we ate some supper around 4 and spent some time watching Netflix before I headed off to have a shower. It’s been around 10 months, and I have let some areas of my face grow in more than I should so that needed to all be cleaned up. Plus, as this may be the last few times I can dress this season I decided I would get rid of the chest hair as well. I did not to get too crazy for this first time and I just decided to wear a really nice floral print blouse and a really great fitting pair of jeans, I figured makeup would be too much work and maybe too much for the first time.
When I was all ready, the kid was in watching some videos with my wife and I planted myself in the comfy chair and played some video games while I waited. When they finally came out there was not even a “WOW” moment, they just came out and sat on the couch like every other day. My wife double-checked with how they were feeling seeing me like that and the kid replied, “it’s just clothes”. So the rest of the evening was spent just chilling in the living room as if nothing else was going on.
I had planned on getting dressed up again on Sunday afternoon and this time going for some makeup as well. The plans did just not work out the way I had intended them to, in the morning I went out to get groceries and after I got all the cold stuff put away it was so nice out the three of us decided to head out for a walk. After walking around our neighborhood for a bit we headed back home, grabbed a bite to eat and I tried to lay down for a nap.
I can’t really say I slept much and still felt as tired as I did when I laid down, but it was around 2:30pm and I had to finish putting all the canned and dry foods away plus do the dishes while I also started supper. I had given up on doing any makeup for the day because it’s just too much work that late in the day for me.
After supper, I did decide to at least partially dress up, so I headed off to have a shower and picked out a new top to pair with my comfy jeans. Once my shower was over I hopped into my underwear, popped my forms in and headed off to the living room to have a sit-down and finish watching some Grays Anatomy.
It’s a great thing to know that I now do not have to wait until the kid leaves to be able to dress anymore and seeing as our numbers are going up here in the city I can’t see the kid being able to go anywhere for the foreseeable future.
I don’t plan on dressing at home all the time now but it’s great that we all feel that I can and no one really has any issues with it.
So where does it go from here?
From what I can tell our kid seems pretty open to the fact that their Dad likes to wear dresses at times and seems somewhat interested in the knowledge that I may have that can help them with their own interests like cosplaying.
Beyond the makeup, clothes, and all the lacy lingerie you could ever pick out, the most personal thing a Crossdresser gets to pick out is her name. Out of all the things I have picked up over the years for my feminine persona my name is the most personal. There can be a million different reasons for a million different Crossdressers for how they chose their name, Some have picked old Girlfriends, movie stars, and even family names. And although it seems small, the name is how you present yourself to the world.
Yes, I had known I was a crossdresser since about the age of 7, but up until the year 2000 (17 years later) I was never able to talk to other people like me. Here on the internet was people who had embraced their female side to the point of giving themselves names, something up until this point I had never really thought of before. Also, my Crossdressering was still a touchy subject at this point. I was still very much was uncomfortable with it but it was evolving.
I decided that it was time for my femme side to have a name but I would be lying if I told you I remember all the variations I had come up with or that I had put a ton of thought into it. There were a lot of Jenny’s, Lisa’s, and Rachael’s, but I wanted something different. My exact line of thinking is lost to me now but somehow, someway I finally decided on Anastasia.
Anastasia (from Greek Ἀναστασία) is a feminine given name and the female equivalent of the male name Anastasius. The name is of Greek origin, coming from the Greek word anastasis (ἀνάστασις), meaning “resurrection”.
Wikipedia
Until writing this post I had never before looked up the meaning of the name Anastasia, but now it seems the name may have struck more on the head of the nail than I knew. It was a type of resurrection as I was really finally accepting this side of me and now I was putting a name to it. It would no longer be that thing that I did and hated later on.
Anastasia stuck around for about 4 years. I spent many long nights staring at the computer screen chatting to like-minded people. I learned so much in this short amount of time. I wish I remembered more from this time but I did not have the sense of acceptance of myself then as I do now. At this point in life, I didn’t even own any clothes of my own as it was always more important to make sure our rent was paid than getting any extras for something that I was still not totally sure about.
Almost at the end of 2004, there was a shift and I became tired of Anastasia. I think it was just more evolving to the point where I am in today. I think I hurriedly picked Anastasia just so I could fit in online, but on some level, I knew it was not really the name I wanted. I would love to say that my next name came to me as a great epiphany or in a dream-like it was some sort of cosmic intervention, but alas it was not. It is more likely that I saw it on a sign in our local town and for some reason it got stuck in my head
Cynthia is a feminine given name of Greek origin: Κυνθία, Kynthía, “from Mount Cynthus” on Delos island. It can be abbreviated as Cindy or as Cyndy. There are various spellings for this name.Cynthia was originally an epithet of the Greek goddess Artemis, who according to legend was born on Mount Cynthus. Selene, the Greek personification of the moon, and the Roman Diana were also sometimes called “Cynthia”.
Wikepedia
Some Crossdressers go through tons of names before they find one they really like and others never pick a forever name and prefer to change it as much as their clothes. For whatever reason, Cynthia became cemented in my mind and I never looked back. I cannot find the exact date when I took the plunge but my first email sent as Cynthia to a salon in my town was November 25, 2004. Sixteen years late I am still Cynthia (sometimes) and I don’t see that it will change anytime soon.
All pictures are property of either Addition Elle or Penningtons and parent company Reitmans.
I think as a Crossdresser, at times we go to the extremes and obsess. We want the best makeup, clothes, and underthings. And even though we think we need these things, sometimes we don’t always get our way. Here are some of my favorite pieces that got away.
Almost all of my clothes come from 2 stores, either Penningtons or Addition Elle, Sister stores owned by Canadian retailer Reitmans. Addition Elle recently closed all of its brick and mortar stores and are now being sold from Penningtons stores. You might wonder why I would shop exclusively from somewhat expensive stores? Well, they both cater to plus sizes, and during their sales and clearance’s you can get some wickedly good deals. I have bought some really nice skirts and dresses for less than I would spend on some takeout lunch.
You can check out Penningtons.com to see some of their stuff.
I posted this one before but this would have been the first dress I ever purchased on my own without my wife’s help. Unfortunately by the time I was able to make it to the store the dress was already sold out in my size. The lady at the store really helped me try to find something that was close and I really think the replacement one was just as good or better.
I wished I had saved more pictures of this dress but this was before I decided that keeping pictures for my blog was a good idea.
Moving back to my Christmas Wish list for 2018 I had this Baby Doll Mixed Media Flutter Sleeve Lace Dress by Michel Studio through Addition Elle.
If you can remember any of my other posts, I have a real soft spot for lace anything. I do like the fact that it has at least short sleeves but I am not so sure about the length. My legs are not what they used to be. I love the line that Addition Elle used to explain this dress.
Add some lipstick, high heels and you’ll be turning heads in this romantic and sexy plus size baby doll dress.
Moving ahead to Christmas 2019 we have 2 more dresses on the list. Firstly we have the Knot-Front Lurex Dress.
This dress is right up my alley. It’s not tight-fitting and flows but it’s also made with metallic fabric which gives it that little POP.
The next dress is the Black Lace & Pleat Dress.
I am not a fan of sleeveless dresses but I think I could deal with it by wearing this number. I really love the lace accent at the top and the cut-out in the back. I would probably still have added something to cover my arms though, shawl maybe?
This is the dress that spawned this whole blog post. This is the Addition Elle long sleeve velvet dress.
I came across this one back in late December or early January. At that time it was still at the regular price which I think was around $79.99. I will admit I did go back to the website and check it out more than once. It did finally go on sale and at one point was down to $32.00, still more than I should be spending on a new dress. It did not matter the price because there was no stock at the local Penningtons and I don’t do online shopping. This is fine because as my wife says, my side of the closet is brimming and I don’t really have room to cram another dress in there.
This dress really would have been me though. Velvet, with the mesh upper section, just screams Cynthia’s style. Plus it has full sleeves, and the only issue I can see with that is me wanting to roll them up, not really something you want to do on something this delicate looking.
Unfortunately, owning this dress was not to be, there is no stock in any Penningtons store near me and I don’t do online shopping. And honestly, even though I really wanted it I know I have no need or room for yet another dress that will sit on a hanger in my closet gathering more dust than hours of wear.
Even though the following ones did not get time in a blog post they are still pretty high on my list.
Still in lock down here in Ontario, so I thought I would re-live some happy times from the past. Be warned, there is a ton of pictures in this post.
I keep it no secret that I have never been out in public dressed, but that’s not to say that as I have gotten older that it’s not on the table.
For most of my life as a Crossdresser I had no desire to leave the house. It was equal parts fear and not being skilled enough in my dressing and makeup to even come close to passing. But has I have aged more the itch to get out has become stronger.
The first step in this process was leaving my house in broad daylight. Way, WAY back in 2018 I was asked to house sit for someone and it would be at least 3 months of being by myself on a large chunk of property well off the road. There was all the privacy I needed to get outside and enjoy some of the sunlight and more than enough driveway that if someone was to try and come in they would be seen and I could retreat into the house.
August of 2018 rolled around and I packed up all my stuff to take with me to house sit. About 3 boxes of clothes, makeup, and other miscellaneous objects along with my camera. My first chance to dress came about mid-month, I had tried previously to that but I found that +28 degree heat and humidity in Canada did not equal a great experience wearing makeup.
When we finally got to the point in August where the heat was bearable enough to wear some makeup and not have it slide off your face I decided it was time to try again. The upstairs of this house had a clothes rack hanging from the wall and was a great place to hang up all my clothes so they were ready for a quick change. Makeup was difficult because the only room that was adequate to apply was a very small bathroom with terrible lighting, through some trial and error I made it work.
Once my face was done and I was dressed in my first outfit, it was time to head outside. This was my first trip outside past the front door and the feeling of the sun on me was great, it was like I was seeing the outside for the first time with new eyes. I was still a little cautious even though there was no way I could be seen by anyone, years of trying to hide my dressing had taken their toll. I set the Tripod up and programmed the camera for a 10-second timer and a 5 shot burst. I donned my wig pushed the button and stepped in front of the lens.
I found the 5 shot was the best method for taking photos because it gives you some time to move between the shots giving the pictures a little more life.
I couldn’t tell what the pictures looked like on the crappy little screen on the camera so I figured it was best to take all the pictures I wanted with all the outfits I wanted to wear and check them on the computer later on. After my first outfit, I changed 4 more times and took close to 100 photos.
After packing up the camera I sat down in the chair with my trusty laptop in hand and waited patiently while the pictures were uploaded from the camera. Of course, there was a fair share of pictures that did not turn out or were out of focus due to me moving but the majority (at least in my mind) turned out well.
Truth be told I hate having my picture taken while in male mode, I have actively tried not to have my picture taken since I was in high school. So I was kinda shocked when after about a dozen photos I came across these couple.
There was a hot wind blowing through the yard that day and it just made the dress flutter in the wind. I have to say it’s really the best picture of me taken ever.
Scrolling through the other photo’s made me happy that I had taken the chance to head outside for this little adventure.
Clearly, you can tell this was the wrong color foundation.
I was able to experiment with so many of my outfits and dresses that up to that point had been sadly hardly every worn. The dress below specifically was one of the first dresses I went out and bought on my own with no help from my wife. It hold’s a special place in my closet.
So it continued for the remainder of August and into September and October, I was able to dress and just relax or dress and head outside to take a bunch of pictures. It was one of the most fun times I have ever spent. It was great being able to take the time to work on my makeup skills and put a little more thought into my outfits instead of just reaching into the closet and pulling the first thing out.
Not only did I have the experience of getting outside, but this was the summer when I really started to properly expand my makeup and tools. I was getting closer to my proper shade of foundation and with new sponges the applications was turning out better. Experimenting with a decent set of eyeshadow brushes really makes the application easier and look 100% better even for an beginner like me.
This was also the time when I was experimenting with different types of foundation, specifically Maybelline Fit Me Matte+poreless. I had purchased at least 3 colors and was experimenting with them during all the pictures. You can clearly see in some of the September photos that my foundation was not the proper shade. Thankfully the next color I tried was spot on and I have been a true believer of Maybelline face products since.
So do I still want to get out of the house? Yes I do, but Currently that’s not an option. Hopefully we can get ourselves out of this COVID mess and try and get life back to something normal. I still have some hopes that a local CD meeting group can be started here in the city, I have seen some other interest in it so we will have to see where it leads once people in Ontario are allowed out and about and have decent access to the vaccines.
I find myself digging back into my digital storage and looking at the pictures and not only seeing a new experience that I had but from the perspective of 2020/2021 feels like a simpler time.
The upstairs of this house had a clothes rack hanging from the wall and was a great place to hang up all my clothes so they were ready for a quick change. Makeup was difficult because the only room that was adequate to apply was a very small bathroom with terrible lighting, through some trial and error I made it work.
I was getting closer to my proper shade of foundation and with new sponges the applications was turning out better. Experimenting with a decent set of eyeshadow brushes really makes the application easier and look 100% better even for an beginner like me.
Cynthia's Crossdresser Journey 