My Very First Pair
Yesterday, I purchased my very first pair of high heels. I went to a local discount shoe store and engaged a rather sexy middle aged sales lady. I told her I'd like to try wearing heels when I am pleasuring myself and she smiled and said she thought that was a great fantasy for men. I tried on several pair and finally settled on a pair of black pumps with a three-inch heel. She said that once I get acclimated to wearing and walking in these heels, then I should come back and see her to possibly go up to four inch. I paid for the shoes and told her I'd let her know how they worked out. I told her I also wear stockings and I think my experience will be greatly heightened with the heels. She gave me a huge breast hug and told me to let her know how things work out. I got home and immediately got into my new ensemble.
— Tim, 22