7 inch pain

I will be in Mississauga on business for a whole week in early June. Does anyone know if there is a particular area in Toronto that is good for acceptance of heeling in the late evening? I'm real nervous but I come from a small town with small minded people and I think it may actually be easier in a busy metropolitan place. I'm definitely going to go for it. Anyone else in Toronto do this?

This Toronto thing sounds good. I actually live near London, Ontario but it might be worth the trip to TO to go for my first real "out in public, do my own thing". I've done gas stations and winter walks with a woolly hat, raised collar and sunglasses but I havn't gotten comfortable enough to just go for it unrestricted. I want that. Is there a particular area in Toronto where heeling would be more accepted? If so, someone please let me know. Thanks.

I had a real high heel day today. Firstly, I spent the day away from my family as I drove 4 hours to see a friend. I was wearing my 4" ankle boots whilst driving and I coughed up the courage to do the "Gas Station Thing". I stepped out of the car and was immediately spotted by a woman filling her van up at the pump in front of me. She said nothing and looked away. I pumped my gas and then as I walked to the booth to pay, the two girls inside on duty saw me. I could see them staring out of the window. I went inside acting as normal as I could but I was shaking like a leaf when I was signing my name on the credit card transaction. One of the girls was stood at the end of the counter and I could see her checking out my heels. They said nothing but I could see smirks on their faces. I walked back to my car, jumped in and sped off. I was sweating with nerves but it felt great. I feel I will have to repeat this soon. Secondly, my wife went off to work the night shift tonight and I tried something very different once she was gone. I found I could squeeze my 6" pumps inside my mens cowboy boots. It was real tough getting them over but I did it. It effectively raised the heel height to 8"! (the toe base was slightly raised as well though so it was a bit of a cheat). Nevertheless, this was easily the most vertical my foot had ever been. I walked around the house like this until my ankles were shaking so much, one just buckled and gave way. It wasn't pretty but I could walk! Once I slid the boots off and just left the 6" pumps on, they seemed so much easier to walk in than ever before. Seems I might make my goal of sometime walking well in 7" heels afterall. I guess it was a bit like foot training. Practice, practice, practice eh? This idea of wearing high heels inside a largish pair of mens boots intruiged me though. This could be a way of heeling in public without too much attention. Has anyone else tried this? Seems like a real possibility to me. Although I would have to lower to 4" heels inside the boots to be able to walk even half normally. I looked hideous stumbling in my makeshift 8 inchers! Let me know your thoughts.

I have reached the point where I drive out to a quiet neighbourhood and go for a walk. I am a straight guy with no other cross dressing tendencies. I just love wearing womens high heels. I'm not into platforms or male style loafers or anything. I wear 4" tan stiletto ankle boots which I bought in a shoe store without trying them on. I can walk in 6" pumps so they are easy for me, but a thrill nonetheless. The problem I'm having is every time I go out I tell myself to walk from the quiet area into a busier area and just go for it. But as soon as I see anyone else I just do an about turn and I can't get back to my car quick enough! I end up almost running with my confidence gone again. This has happenned about six or seven times now and I just can't get over it. Anyone else having the same trouble? Maybe there's some guys out there who have been through the same but have managed to conquer their fears. Would love to hear any good advice. Thanks.