It’s a good things those windows were tinted. He couldn’t allow those people on the street to lay their eyes on him, too good for them. What else would a glamourous man in the back of a limousine think? They probably assumed he pitied them, that he couldn’t bring himself to look out the window at the masses of repulsive middle class scum going about their night routine.
That’s not why the windows stayed up. He was scared.
Scared of what?
He wish he knew.
Scared that they might see through the tint of his windows and the glare of his expensive sunglasses and into his eyes, and see him for who he was. Human.
Just human. Not a normal one, not a simple one, but human. A human who couldn’t remember if he was returning from an award ceremony or an exclusive party hosted by celebrities, or whether his newest sports car was three million or four million. He just couldn’t find himself caring.
He cared about little anymore. The part of a person that cares about anything is deep inside, and his had been drowned by expensive suits and late nights with gorgeous women.
Understanding was still the hard part. Like understanding how someone could feel the way he did when every problem had a thousand pounds of diamonds to counter the dilemma. Or understanding how to leave this paradise, or if the mark he’d left on the media and the public was too noticeable to come and be what everyone called ”normal”. Whatever “normal” meant, it sounded irresistible. He wished he knew where to buy it.
He stepped out of the limousine at the bottom of a skyscraper covered with glass and modern technology. He got in the elevator and pressed the button to his home. His penthouse that hogged the roof. Such a grand elevator. Polished and glossy. It made him wonder why it was made so perfect if he was the only one to use it. It made him wish that anyone was on it with him, just a man minding his own business, it didn’t matter. Just someone to share the space with other than a bodyguard or a woman with lustful intent.
The penthouse matched the building. It was modern, it was expensive. There was no comfort in the knowledge that there wasn’t a single person in the building who could live higher than he did. He wanted someone to. He wished to be below someone for a change.
He poured a long stream of whiskey into his cup. The lights were still off, so it was hard to tell when it was full. He let it flow over the lip and run on his fingers. His distracted body followed the only light in the room, which came from outside.
The city.
The skyline was visible through the window, but he stood on the terrace to feel the wind in his hair. This view should have been breathtaking. This whiskey should be the best thing a man should taste. This apartment should be beyond anyone’s wildest dreams.
“Am I allowed to wish?”
The only one worth pitying was the face he saw when he looked at his whiskey.
“Am I allowed to wish for one more thing?” He asked the city. One of the most expensive places to live, some said. Some people came here just to buy things.
He smirked at himself. “But here I am, asking for more.”
This time he said it to all of his possessions. The sum of his status and the person the talk show hosts thought he was.
“I wish I was sad.” even as he spoke, he could feel the missing tears that should be stinging in his eyes, like the itch of a phantom limb. A deep sadness, an overwhelming urge to cry without end would be preferable to the bleakness of his heart. The barren wasteland he called his emotions.
He drained half of the whiskey in one long sip. It’s no use. It can’t dull what’s already numb. His fingers accepted that, and the cup clattered on the deck. His legs accepted other things at the same time.
He shakily climbed the chair, then a table that bordered the railing. Just standing there in the wind, chest out to the open city. God, how he wished he could cry. How badly he wanted to break into a sobbing mess and curl into a ball of tears.
But his face was slack. His eyes wished for tears, but none came. The brilliant lights of the city simply shone in bare eyes that were as dry as bone. He feared the sting of the wind in his unblinking eyes was the only pain he could know that night.
Finally, he dared to look down. So far down…
To the people he was so used to seeing as small compared to himself.
What’s at the bottom?
Not the cold asphalt or the traffic or the life, but the possibility?
He saw a vast and unexplored potential below him. Only one step in front of him, so to speak. So easy. The discovery was just so close. So real.
He looked down. He stared. And as he watched the windy abyss below him he saw himself there. He could see that man finding an escape from the numbness that ran deeper than his bones. The Oasis in the bleak paradise…
The final refuge.
And that was enough.
The tears welled in his eyes like a blossoming flower, and finally he felt the grace of a sob tearing apart his chest that he hadn’t experienced for months. He collapsed on the deck beside the glass and the river of tears that ran from his soul joined the puddle of whiskey on the ground.
Unmoving in that spot he wept, besides the quiver of his lip and his trembling lungs. When day came, he continued to weep, and when his weeping stopped, he did not move for hours to come. He cherished every single one of those seconds that saved his life. And each night he wept, for reasons unknown to even him.
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Hey there! EverWinter here for a review!

So, to start, this is a good piece. I like the real feel to it. But this man's emotion was off. That is what it feels like to be depressed. What he was feeling was depression and a deep sense of how broken he was. Lonely too. And that needs to be woven into the story. At the beginning he wasn't scared. That's the wrong word. He felt vulnerable and broken.
And on to the end of the story. This needs to be more dramatic. He wants to feel something. Anything. Even pain. So he gets on the roof and considers jumping. He should stand on the edge. He stands there for an unknown amount of time, willing himself to jump. When a breeze passes and he becomes off balance, and then he steps back, falling next to his broken glass. That's when he should cry. And through the tears and the gasps for air, a small brief smile emerges only for a second, because FINALLY he can feel something.
Does that make sense? To make it more dramatic too, use really simple vocabulary up until he's feeling something. The fear of almost falling. The anguish that finally has shown itself and the brief, dull glimmer of joy that he has in actually feeling something. Simple vocabulary slowly changing from "He felt nothing. Nothing at all. He wished to feel anything, even pain." to "And as he fell back, reeling, the long awaited sob burst through the air," Something like that. I think that would help.
Or even, as a final thought, you could have him not even sob. Silent tears with an occasional grunt or moan. I mean, that's more dignified than a full grown man sobbing on his roof uncontrollably. Have his back pressed up against the wall, head tilted towards the sky and tears streaming down his face. I think that could work.
Anyways, I hoped this helped. Your grammar and spelling were perfect, so you did a good job there. You pretty much had it nailed what that man would act like, you just needed a little help with pinning down what he was feeling. I like this story and I hope you continue to work with it.
EverWinter
Well, this seems to be a realistic depiction of what the 0.001% feel when they realize how much time they have been wasting with the trivial materials.
For one, the setting seems incredibly realistic, and the city is basically a civilized wasteland.
For two, whoever the protagonist is, he seems to be desperate for a friend, no, not a girlfriend or trophy wife, but a actual, intelligent person who he can talk to.
And for three, the protagonist seems desperate to feel emotion, obviously the fake material happiness has long sense worn off, and now whoever he is realizes their fate.
In all, this is probably what real emotion from someone who is otherwise emotionless would feel like.