Is this a Homestuck fanfic by any chance?

There actually isn't any. All you get is him saying, "It was a routine assignment."

Reminds me of my family...

Can't we find an image that actually does make sense in context?

That is more an example of It Makes As Much Sense In Context, but just because this picture has no context doesn't mean it isn't a good visual guide.

Maybe something from El Goonish Shive, like female!Tedd in a dress saying "I don't crossdress in women's clothing" or Elliot's "I'm too young and too male to be the mother of a 17-year-old female me!"

Get the pic, upload, then show us in a link.

Possibilities: http://imgur.com/a/UaSpJ (third one is from Skin Horse)

Oh, why not, one more Skin Horse: http://imgur.com/0JnTKbW

Not bad, but I think one of the other three would be better.

Heh, that's pretty good.

Fu- Can't... Stop... Laughing...

Than this image◊? Heck yeah.

Looks more like less disturbing in context to me.

No idea. I'm always disappointed that there are never any examples present when I visit this trope.

The whole point of examples is to demonstrate the trope. This is already done in our small list.

This isn't a trope for everything that makes sense in context. It's just a page to explain what we mean when we use this phrase.

Because...the examples don't make sense(?)

Because the Stop Having Fun Brigade likes to cut examples.

If you want a very quick rundown of how this trope came to be, it was originally proposed as a better formed version of the (Now Defunct) I Am Not Making This Up, where something seems odd if you just came into the story but does in fact make sense given the context. It was eventually modified to become a predefined message emphasizing the fact that you can't always explain the context of something without bloating the example by a factor of three. Being a predefined message, that means it is a verbal shorthand to describe something and is not a trope in and of itself.