Driving for a rideshare company
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While driving for a rideshare company, I usually only wear a skort during the early morning hours when it is still dark. Today I wore my dark green skort and heels until 10 am. I got a few smiles when riders noticed, but no one said anything until I picked up someone going to the airport. It was a young lady with several bags. I got out to place her luggage in the back and she quickly commented "I have never had a male driver who wore a skirt before!". She smiled as she said it and I replied that they were actually shorts that look like a skirt from the front. She just smiled and said that I looked good in them especially with those heels. On the way to the airport she also commented that she wished more men would wear skirts and heels. She liked the way they showed off my legs. I thanked her for the compliment. The ride to the airport was only about $15, but later I saw that she gave me a $20 tip. I felt wonderful to be noticed and complimented. Thankfully no one had anything negative to say. Needless to say I will be wearing a skort or skirt with heels from now on when I drive. I kept thinking about the lady's comment about how she wished more men would wear skirts and heels. I hope to see that happen soon. A skirt or skort can really highlight some sexy legs better than shorts.

- 24 Aug, 2025
- 15 likes
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Compliment deserved!