Last letter = First Letter, min 3 syllable word chain

desperate

-“BB”-

engaging

galoshes

saturated

demigod

deductible

edumacational

Laertes

Sisyphus

septicemia

arterial

languishing

golliwog

-“BB”-

gallivanting

gubernatorial

lorikeet

Transmogrified

Dunciad

devastated

demoralized