I started wearing heels as part of my crossdressing, first inside my house most of the time. At the beginning, I just wanted to get used to the feeling of being "en femme" for a night of reading, watching TV, etc.
Then, I started going outside for short walks around the block, or to get to my car for a short drive to a remote "desert" area, where I would walk a few blocks in the night. In order to be able to walk in heels for longer excursions, I started to wear my shoes when working at home, even if I wasn't dressed. And I must admit that I love the feeling.
A few years ago, I went a little further in my crossdressing, and spend a few nights in a night club for Transvestites (Café Cleopatra, in Montreal) dancing and chatting with males shemales patrons (never going further). Then, I started to go to the Bank Machines, or even to restaurants and Cinema being "en femme". Sure I was not a goodlooking woman, but nobody ever seemed to notice anything special with me !
Currently, I have a beard (my beloved wife, who knows about my crossdressing, but loves me better in my male apparence, prefers me with this beard... and I must admit that, as a male, I'm better with than without). So I only venture outside "en femme" during winter time, when it's cold enough for me to wear a tuque and a long wool scarf that I can use to cover the lower part of my face. I've been to a film 3 times, in the last 3 weeks, dressed as such. But most of the times, I will just wear Hign Heels boots (4½ to 5¼ inches) under my pants, sometimes for very long walks, something like 5 or 6 kilometres or more, i.e. one hour or more. Nobody ever made any comment, even not a special look ! So I tend to do it more and more. With a great pleasure, each time.
how did you work your way up to street heeling?
in For the guys
Posted
I started wearing heels as part of my crossdressing, first inside my house most of the time. At the beginning, I just wanted to get used to the feeling of being "en femme" for a night of reading, watching TV, etc. Then, I started going outside for short walks around the block, or to get to my car for a short drive to a remote "desert" area, where I would walk a few blocks in the night. In order to be able to walk in heels for longer excursions, I started to wear my shoes when working at home, even if I wasn't dressed. And I must admit that I love the feeling. A few years ago, I went a little further in my crossdressing, and spend a few nights in a night club for Transvestites (Café Cleopatra, in Montreal) dancing and chatting with males shemales patrons (never going further). Then, I started to go to the Bank Machines, or even to restaurants and Cinema being "en femme". Sure I was not a goodlooking woman, but nobody ever seemed to notice anything special with me ! Currently, I have a beard (my beloved wife, who knows about my crossdressing, but loves me better in my male apparence, prefers me with this beard... and I must admit that, as a male, I'm better with than without). So I only venture outside "en femme" during winter time, when it's cold enough for me to wear a tuque and a long wool scarf that I can use to cover the lower part of my face. I've been to a film 3 times, in the last 3 weeks, dressed as such. But most of the times, I will just wear Hign Heels boots (4½ to 5¼ inches) under my pants, sometimes for very long walks, something like 5 or 6 kilometres or more, i.e. one hour or more. Nobody ever made any comment, even not a special look ! So I tend to do it more and more. With a great pleasure, each time.