Can you be literal about non-literal things?

Solution 1:

"I'm literally going to fit him for cement shoes."

This would mean more than simply "I intend to kill him." It would mean "I intend to encase his feet in cement and throw him in the river [or lake, or ocean, etc.], thereby killing him".

That said, the sort of person who would actually kill someone in this way — who would speak those words in a literal sense — is someone who is not too worried about violating convention and would very likely not be fussy about speech and grammar; he might easily mean "literal" in its corrupted "figurative" sense.

EDIT

I see from the comments that some people insist on carrying any expression of literalness out to six decimal places; in other words, that for a thing to be described as being "literally" some state or condition, the state or condition must be exact to that amount. Or more.

I disagree.

The act of "fitting someone for cement shoes" (or overshoes, or boots) refers to a very specific way of killing someone. It is a figurative description, but one which describes a real action: putting someone's feet in a tub of cement, letting it harden, and then hurling the poor unfortunate to his death by drowning. To that extent, I insist that someone could be "literally fitted for cement overshoes" if they were killed in the manner that the trope suggests. The expression does not cover murder by gunfire, garotte, stiletto, or poison, but it does cover that particular case. Literally.

Let's look at another case:

I'm going to literally beat you to a pulp.

Now, the literal-minded may insist that the word "literally" may not be used there, because "to a pulp" is a figure of speech. But if they do, they first have to explain exactly what degree of beating qualifies or doesn't qualify as producing pulp. A mashed nose or smashed ear or other severe deformation may be construed as a "pulping," and if one allows that at some point pulp is produced then the argument becomes trivial and pedantic and not worth the trouble. The objection is reduced to the state of an advertising claim for orange juice: no pulp, some pulp, lots of pulp.

I believe that if someone threatens to "literally beat me to a pulp" I face severe damage to my person. Whether or not that qualifies in some minds as "pulp" is irrelevant.

Now, we have to look at this on a scale. The guideline to apply here would involve whether the action or state described as "literal" does contain actual parts of truth ("some pulp") or none at all ("no pulp"). If someone says

It literally made my head explode.

we may poke fun at them by saying their head has made a splendid recovery since them, because they seem to be talking out of it. In that case, the figurative expression (even though it does describe a state of abject bewilderment or consternation) is rendered ridiculous because it is too far from reality to be considered literal in any sense ("no pulp").

To sum up: This is all a matter of degree. Some figurative expressions, if they refer to actual actions or conditions that can be produced, may be modified by some form of the adjective "literal" — even to the literal-minded. (Hey, did we agree on what a mind is yet? Literally?)

Solution 2:

Literal has an absolute meaning, and if you accept that absolute meaning then "I'm literally going to fit him for cement shoes" means only, literally, that -- to measure the person's feet so that you know what size cement shoes he would wear.

However, people use literally in a non-literal sense quite often, just for emphasis:

She was literally tearing her hair out.

(...where the subject was not, literally, tearing her hair out)

So we can accept that, in everyday speech, literal has varying levels of absoluteness.

You've identified a situation where a figure of speech is layered on top of other meanings:

• "Fit him for concrete shoes" could imply...
• "Encase his feet in concrete and throw him in water" could imply...
• "Kill him" (either using the actual method above, or some other method) could imply...
• Scold him seriously

... and you want to know whether adding literally strips away one layer, or all of them.

The answer is that if we take the absolute interpretation of literal, then it strips away all layers. As I showed above, it would mean to measure him up and find out what size concrete shoes he would take.

However if we take the less absolute interpretation of literal, then the meaning becomes ambiguous. We simply can't tell how many layers of interpretation literally removes from the meaning. We just have to use our knowledge of the context to make an educated guess.