The ironies of life motivated to write this very interesting and true story...
My work requires me to do extensive international travel. In one this trips, a very attractive girl named Jo appeared in my life. At that time, she was working for one of my closest local business partners. Jo is very educated, well travel, and fashion savvy. Her style is leggings or mini skirts/dark tights paired with 3-4 inch heels either pointies or boots.
One night we are all out celebrating the closing of a big deal. Everybody is slightly drunk. When the party ended, I offered Jo to pay for a car service to take her home. She accepted and we went back to my hotel. We engaged in a good conversation while waiting for her car. She complimented me on my tie; I reciprocated by complementing her boots. We both agreed that heels, as ties, can make or break an outfit. As the car pulled over to pick her up, I joked that she can borrow my ties anytime. Night ended with a traditional kiss on the cheek.
A few weeks passed by and I had to return to her country. I got an email from her asking if I can bring her a few things from NYC. Of course I said yes. Jo said it was her last day on the office, she was switching jobs. Left her stuff, plus a tie, at the front desk for her to pick up. I thought it was a good idea to include a tie as a personal touch. The last day of my trip I receive a very unique surprise! Jo had left me a thank you note and a pair of 4-inch peep toe heels!! I was blown away! Sent her a thank you email and an invitation for coffee the next time I was in town.
I never got her new email and lost track of her. Destiny reunited us at a restaurant. It was a pleasant surprise. We had a couple of drinks and a LONG conversation about life in general including high heels. She jokingly asked if I had worn my shoes out. My response was that I was going to do it only if she wore her tie. That sparked a discussion about men in heels, drag, androgyny, etc. Turns out she is very open minded!
The last day we met and played dress-up with leggings, skirts, and heels. We both had a great time! She was very excited to have a guy friend to play dress-up. We played several times. She ended up buying a matching pair of 3-inch pointy pumps for our play-dates. She really liked how I looked in minis and leggings with heels. We sent casual emails with pictures of things we would like to try on.
During my last trip she shocked me. Jo suggested that we should go on a trip together. And I quote "... let's go together on a cruise. Not a regular one of course, a gay cruise. Lesbians only. Here's the condition, I'll do the packing. You only show up with the clothes you wear for the plane. Day before the cruise we go together to the spa to get our nails done. Only feminine clothes for you all the time ... skirts, tops, leggings, heels, etc. We are going to have a blast!! ... " My heart stopped. I had no words. I have never been into drag, but the experience sounded amazing.
She mentioned that her feelings towards me were changing, and wanted to give the relationship a try. I had found a great woman that enjoyed and encouraged open heel wearing!!! And here is the irony ... I found her a few years too late. We both are in committed relationships. We both know about each other's SOs. Our encounters have never been sexual. Not even a kiss on the lips. Both of our SOs are not supportive of alternative fashions.
As you can imagine, I respectfully declined the invitation. We remain good friends. However, email traffic has reduced significantly. Have not yet returned back to her country... You never know … I thought you would enjoy this true story …
PS ... sorry for the long post