Last letter = First Letter, min 3 syllable word chain

lollygag

gratuity

yellowish

Honorably

yammering

gibberish

hiccuping

glamorous

Symbiotic

clandestine

evasive

Extrapolate

expectant

tertiary

Yosemite

Sometimes it seems that every third letter I get is Y.

Endoscopy

yellowfin

nostalgic

Consequential

luminous