Flight of Fantasy

[Thighbootguy]

Flight of Fantasy

First, you have to understand that I enjoy wearing high heeled boots, and that translates to wearing them as part of my normal attire out in public. Some folks think a guy wearing boots with 4” stiletto heels is “different” enough to venture a comment, but most folks just glance and keep going.

I had to make a business trip to Denver and wanted to travel in comfort so I headed to the airport in jeans and a pair of knee high black leather boots with 4” stilettos.

I parked in one of the long term lots and hitched a ride on the airport shuttle. The driver and I talked about what a great day it was for traveling and he hoped I’d enjoy my flight. In the terminal, my heels made a delightful clicking sound on the terrazzo floor and I was careful to avoid slipping on the smooth surface. I checked my bag, picked up my boarding pass, and headed for security.

There was a fairly short line at the security station. I put my purse on the x-ray station belt, unzipped my boots and placed them on the belt. I now understand why folks are wearing horrible looking footwear at the airport. I went through the metal detector without setting it off and went to pick up my purse and boots. The security guy gave me a second look when I reached for my stuff as he was clearly expecting a female to gather those belongings, but since no one else claimed them he didn’t say anything. I walked over and sat in a chair and put my boots back on.

As I was finishing with my boots, I heard a female voice say, “Nice boots”. I looked up to see a middle aged lady wearing a black leather jacket and matching below the knee length leather skirt standing in front of me holding a pair of knee high black leather boots with 5” stilettos.

I thanked her for the complement and she continued with, “Do you mind helping me with mine?”

I was a little stunned, but managed to say that I’d be glad to help. We traded places and the creak of the leather jacket and skirt as she sat down was a wonderful sound. She handed me her boots and extended a foot so I went down on one knee and placed her boot on her foot and zipped it up then repeated the operation with the other one. Being down on one knee masked the fact that both of my knees had turned into rubber at the thought of helping to but her boots on. I had thought her outfit looked good with the jacket and skirt but adding the boots made it look great. I managed to stand up again and offered my hand to help her up and we started walking down the concourse together. It turned out we were heading for different destinations but we each had several hours before out flights.

As we were walking, she complemented me on how well I was walking with my heels. I thanked her and said, “It comes from practice… but you already know that.” She offered that she was surprised to see a guy wearing stiletto boots but that they looked good on me. I thanked her and said that I really liked wearing them and that, in my opinion, men’s shoes really looked boring and that I didn’t feel restricted by styles and that I enjoyed wearing things that were different from the norm. She seemed impressed with my freedom and commented that it would be nice if other men saw things that way.

Along the side of concourse, there was a shoe shine stand, and knowing that we both had time, I suggested we give the shoeshine guy something to remember. The shine stand had two chairs (no waiting) so we both sat down and put out boots up on the foot rests. I don’t know what reaction I was expecting the shine guy to have but he got a huge smile on his face and said that he would make our boots look great. He applied polish to all four boots then proceeded to brush and buff them. I did notice several passers by taking a second look at the activity. When he was done working, the boots really did look great. Hers had looked better than mine before we started but now all four just dazzled. I thanked the guy for the great job and gave him a generous tip.

We walked on and continued talking about work, the weather, fashion, … and I found we were able to talk about many subjects. I did mention that I thought her outfit looked really nice and that very few women could or would wear a leather outfit. She replied with a question, “Why do you wear those boots?” I said it was because I liked the look and that it was something different. She said, “That’s what I thought, and that’s the same reason I like wearing a leather skirt and boots.”

We got to her departure gate and we still had some time to kill when she said, “You know, that outfit you have on would look good with a jacket, here try mine and see what you think.” With that, she slipped off her leather jacket and handed it to me. I tried it on and we were close enough to the same size that it fit comfortable. I walked over to a glass partition where I could see my reflection and she was right the jacket made the outfit work. She said, “See that’s what it needed.” The leather in her jacket had picked up her perfume and I was starting to get lost in the intoxicating scent. I slipped the jacket off and gave it back to her while I still could. She put it back on and we sat down to wait for her flight to be called. I was very aware of the creak of the leather as she moved and I think she noticed. As she smoothed the leather of the jacket and the skirt with her hand she said, “You will have to get one of these.” I’m not sure if she meant the jacket or had picked up on the notion that I thought the skirt might be fun too.
I told her I was planning on doing just that. About that time they called her flight and we got up and walked over to the gate. She gave me a very nice smile and said, “I’ve enjoyed out conversation and hoped I had a good flight.” I said about the same thing and she got on her flight.

I don’t know if she realized that I was flying so high that I might not need a plane to get to Denver.

[Dr. Shoe]

What a great story! My fave outfit is my leather skirt suit. I have a mini and a pencil skirt to go with my jacket. I usually wear pumps with the pencil skirt and boots with the mini...

[Bubba136]

Conversation, sounds ---- almost sensual, perhaps?

[Thighbootguy]

Conversation, sounds ---- almost sensual, perhaps?

Maybe...maybe not. I've tried to leave enough for your imagination to work with.