These are some drastic black-mirrorish short stories but not all centering around pains of living in a technological world and rather revolves around general pains of existence and salvation. Every tale is an amazing blend of sci-fi, fantasy but on a speculative side and even psychological thrillers.

I Have No Mouth & I Must Scream
This I believe is one of the bleakest depiction of any sci-fi universe, a super-computer that tortures five last humans alive dwelling inside the so-called stomach of an entire city-big computer. With Ellison himself narrating it, I haven't heard anything more disturbing.

Big Sam Was My Friend
Generally okay, noting its circus background and love-revenge tale.

Eyes of Dust
Another well described pains of existence in an absurd universe.

World of the Myth
I found this one along with the I Have No Mouth to be a great thought-provoking sci-fi

Lonelyache
An amazing psychological thriller that mostly happens on disturbing dreams and visions

Delusion of a Dragonslayer
It isn't that easy once your soul leaves your body, this fantasy describes the salvation itself to be painful.

Pretty Maggie Moneyeyes
This one is particularly interesting with it's anticipating story-telling and how the reality and dreams have better consecutive scene-wise structures.