Crossdresser Sissy Blog Ru

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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.
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 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.
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.
Clipart from the blog banner from AnnaliseArt from Pixabay.
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”.
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”.
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.
Blog banner Vector image by Settergren from Pixabay
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.
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 c
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