Doggiedo,

When you say multiple orgasms do you mean a chain of orgasms or multiple orgasms within a single session/short time span?

I think if you can have one you can have multiple in a session. As others have said, it helps to stimulate differently/space it out so you're not tiring out any particular area. Try lots of toys! Many are pretty inexpensive on Amazon and you don't have to deal with the embarrassment of going to a store (it's also worth going on Amazon just to read through the reviews…people go into all kinds of details). Then you can have fun trying them out.