My Journey into Crossdressing: Shoe shopping and other things.

I have been thinking, for some time, of buying an inexpensive pair of very girly athletic shoes. You know the ones; they absolutely shout girl, and no self-respecting cis guy would be caught wearing them. (Of course, he wouldn’t be caught dead wearing a dress either: His loss). You know the shoes, the ones with pink and, or pastel colors that are oh so cute and scream feminine. So, yesterday I went to Walmart to do some shopping. Due to circumstances, I was dressed in my cis clothing. However, it was kind of fun being dressed as a man while trying on girly shoes. Unfortunately, Walmart’s inventory was low, and I could not find the shoes I wanted that fit, I moved on to the next project. It was time to complete my makeup supplies.

I am not sure if I have mentioned it but, I have never put on eyeliner or mascara. I was looking at some pictures of women that were modeling makeup and I realized how important it was to dress up the eyes with more than eye shadow.

I found an eyeliner and mascara and made the purchase. I then headed for work.

While driving to work, I stopped by the shoe station to see what they had in stock. I found several pair of really cute girly shoes but, they came with some very ugly prices.

The next morning: I decided to leave the house early and head to the park to change into Destarte then head to Meijer to shop for shoes.

I pulled into the park. It was a rainy day so, I had the park to myself. I changed into my blue midi skirt with a blue tee and my new denim jacket. I put on the makeup, including the eyeliner and mascara. I finished getting dressed and headed to Meijer.

I went to the shoe department and started looking around. It was as I feared, Meijer, even though it is a box store, had prices more than I wanted to pay. Then, I came across a pair on clearance. The were a charcoal gray with a bright pink trim. They had my size and the price was right, so I now have a pair of girly shoes to wear.

I next went to the Meijer gas station. I went in and bought a cup of coffee. I headed toward work but, I decided to make a quick stop at Walgreens.

I found what I wanted then stopped by the park to change back into my cis clothes but, I kept on my knee- high hose, my bra, and my bling so I could be a little bit girly.

I think one of the biggest challenges I am facing with my cross dressing is finding a balance between some of the styles I would like to wear, and what would be age appropriate. I would love to try a cute babie doll style dress but, I think I am too old to pull it off. I would also like to try a mini-skirt but, again, I don’t see many ladies my age wearing them.

One other thing I haven’t attempted to wear are stilettos. I not sure if I can walk in them and I am sure they are not comfortable. I am thinking of going and trying some on for fun.

This fall, after I have lost enough weight to where I can wear outfits that have a waist, I think I am going to Maurice’s for a style session. I am wanting to find a style that will look good on me and allow me to have somewhat of a figure. I have never considered buying hip padding but, if I lose enough weight, I may need to consider it so I can have curves in all the right places. I will keep you posted.