When I bought my first stilettos at 18, I was so excited to finally get them. But when I put them on, I found I could barely stand in them. Forget about walking. Still, I was mesmerized with how sexy they made my legs look. I had to wear them.
I wore them all the time in the house. I stumbled around in them and never took them off even when going to bed. After several days they began to feel more comfortable. I began going out after dark for walks in them. They began to feel quite comfortable and natural.
A week later I wore them to a Halloween party where I had to walk long distances and stand for long periods of time. I was very comfortable in my heels and loved all the attention and compliments I got.
I guess the best thing you can do is make sure you have the right size, then wear therm a lot to break them in and get used to them. It’s always worked for me.