Is it possible to have two or more prepositions that are placed after the other?

Answer 1

yes. be cautioned, however, that though some words may appear in their preposition form, their function may altogether be different.

examples of two single-word prepositions:

what am i [in] [for]?
do you know what you're [up] [against]?

examples of a single-word and a two-word preposition:

you came [in] [out of] the blue.
i don't think he's in the running; he was [out] [as of] an hour ago.

Answer 2

Bad Practice

Unnecessary Prepositions
In everyday speech, we fall into some bad habits, using prepositions where they are not necessary. It would be a good idea to eliminate these words altogether, but we must be especially careful not to use them in formal, academic prose.

Bad

She met up with the new coach in the hallway.
The book fell off of the desk.
He threw the book out of the window.
She wouldn't let the cat inside of the house. [or use "in"]
Where did they go to?
Put the lamp in back of the couch. [use "behind" instead]
Where is your college at?

Good

She met with the new coach in the hallway.
The book fell off the desk.
He threw the book out the window.
She wouldn't let the cat inside the house. [or use "in"]
Where did they go?
Put the lamp in back of the couch. [use "behind" instead]
Where is your college?

Answer 3

Yes. I can think of a few examples.
I am in over my head. (in, over).
Put your sweater on over your T-shirt. (on, over).
I'll let you in on a little secret. (in, on)