In large, heavy-bottomed pot with lid, combine olive oil and 1 tablespoon truffle oil. Add about three popcorn kernels. Heat over medium-high heat until one kernel pops. Add remaining popcorn kernels; cover.
Once corn begins to pop, shake pot constantly over heat. When popping slows, remove pot from heat and transfer popcorn to large serving bowl.
Melt butter and mix in remaining truffle oil. Pour mixture over popcorn; toss. Sprinkle parmesan cheese, salt and pepper over popcorn; toss to distribute evenly.
Serve immediately or store in airtight container.