Well for me it would depend how much I won, but for starters let's say I won $16.9 million:
The first thing I would do is pay off my debts. Secondly I would go buy a nice home and furnish it with new furniture. In my new home I would devote an entire room to my diapers: a closet to store them, each organized by brand and type. And since my new home would be away from my home town I would probably decide to wear diapers all the time - 24/7!
Once I am set up in my home I would start shopping for cars. The first car I would buy is a brand new Mustang Shelby GT500, in red with white stripes! Then I would buy a brand new Ford F350 Harley Davidson Superduty truck. It would be used to tow all the future "toys" I get - such as speedoat, house boat, snow mobiles, ATVs, fifth-wheel RV and a car hauler.
Then I would start my used car shopping! I'd do a lot of research on muscle cars and try and locate them across the country.
And my first holiday would be a round-the-world cruise, of course diapered the whole time!