Slipping into a Shoe
When I was 14 I had been bored with just normal wanking, so I found one of my canvas slip on shoes and slipped my cock into it (but put an old sock onto my cock first so I could wear the clean shoe after), then I lay down on my bed and humped away. I then got Solo Touch up on my computer to read some masturbation stories. Soon I was cumming, having the best orgasm of my life. And I have been doing this type of masturbation ever since!