First of all let me say I love this site it is really refreshing to know that I am not the only one who enjoys self love. So this happened about a year ago.
At the place I worked my boss used to change her shoes in the bathroom (Basically from street to work shoes. We worked in a restaurant so street shoes slid to much on the floors. Anyway I always liked her but she was married and happy which left me little chance for anything. Although it was indicated to me on a couple of occasions if things had been different we might have had a chance.
So one day I was opening the store by myself and had come in early to prep for the day. I had to go to the bathroom when I went in there I saw her shoes on the floor under the cleaning rack. I guess she had left her shoes from the other day. I couldn't help myself, so I stripped down completely and grabbed the shoes. I put one shoe up to my nose and inhaled deeply (aw the smell was wonderful) It was not pungent or anything bad. As I sniffed I began to masturbate harder and faster. I rubbed my cock with the other shoe a little bit, and I couldn't help but lick the outside a little. In minutes I was ready so I pulled the shoes down to my cock and came all over the outside of the shoes. I must have shot 6 or 7 loads onto those shoes. I looked at them for a minute or two savouring what I had done. Then I hurried up and cleaned them off completely.
I purposefully did not get any inside of them because that would not have been cool. I cleaned the floor and got dressed. Later when she came in she changed her other shoes and never noticed or said anything. She left other pairs of shoes several other times and I used those as well.
I finally moved on and changed jobs. But sometimes when I am really horny I think about that first session and how wonderful it felt to cum on those tennis shoes.