Shoehorn

Definition: (from dictionary.com)
-noun
1. a shaped piece of horn, metal, or the like, inserted in the heel of a shoe to make it slip on more easily
-verb (used with object)
2. to force into a limited or tight space

Examples:

"I always keep a shoehorn in my purse in case my shoe falls off and I can't put it back on by myself."

"How can I shoehorn all your stuff into my tiny apartment?"

Origin: (from etymonline.com)

noun: "1580s, from shoe (n.) + horn (n.); earlier shoeing-horn (mid-15c.)."

verb: "in the figurative sense of 'to put or thrust (something somewhere) by means of a 'tool,' 1859, from shoehorn (n.). Earlier it meant 'to cuckold' (mid-17c.), with a play on horn."

Awkwardness rating: 4

A shoehorn in action. (maniacstore.com)