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 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.
Blog Banner image by Ryan McGuire from Pixabay
Cynthia's Crossdresser Journey 