Last letter = First Letter, min 3 syllable word chain

silliness

sycophant

testosterone

electroencephalograph

hypocorism

Minneapolis

serpentine

epiphenomenalism

Montenegro

outdoorsmanship

Pepperwinkle

emporium

megachiropteran

Nagasaki

idiocy

yellowjacket

tellurian

Nickelback

kleptomaniac

crepuscular