It's how we treat strangers, not friends and family.
If you're demonstrating closeness by "not respecting" people's boundaries, that's an entirely different matter.
I don't mean to pick on your phrasing, except to suggest that how we say things colors how we think about things, and nuances like that matter when we're talking about something as, you know, nuanced as interpersonal dynamics, and especially so with intimates.
At the very least, it's not how I'd want to be treated.
I don’t want to have to ask to be touched by someone whose touch I want. Having the touch come unbidden is exciting and satisfying.
But I don’t want to be touched by someone who’s touch is repellant to me (by any degree). Having to experience or rebuff the touch is uncomfortable or disturbing.
Of course it’s tough to have it both ways! I err on the side of expecting less confirmation in exchange for more of that first example. But as for how I treat others? I err on the side of verbal confirmation, so as to avoid crossing a line someone else takes more seriously than I do.
So far it’s working alright! Is it the best system? Hard to say.
Absolutely it is, in almost any context. In most of those where it isn't, that's probably by design. It might even be the right move.
Where the line falls varies on every single edge of your social graph, all the time. Consent to be touched, or whatever, or not, isn't blanket, but "transactional" is the term used in discussions around consent, and revocable or renegotiable.
But, to your point, especially in some contexts, like flirting, the expectation is to push the boundary, not probe it. There, I think, it's very much a matter of execution. But, honestly, that's pretty speculative; I tend only to flirt well accidentally.
EDIT: Phrasing.
[Edit] I write a little about the topic of play here: https://goo.gl/jHuUQn
You are okay with a close friend touching you on the shoulder or asking personal questions because your relationship has evolved to a point where your boundaries permit it. It is not okay for a person you dislike to do those things because your relationship is such that your boundaries forbid it.
I think the 'too much' is key - occasionally, you should cross them a little. But the opposite happened in the story - he was expanding his kid's boundaries.