When he started his job, he bought into the taglines that came with it: a stepping stone for students who want to advance in their career and pursue graduate or professional training despite curricular difficulties. He convinced himself that this was a loophole to the game, and placed all his efforts into it. If he could just advance without having technically played the game, he would still have won. He would have beaten the system. Hell, he would be better than that system.
He later learned that this was the problem with being
entitled
. You want to be that one exception to the rule. You want to bend the rules and make your own way. You want to play the game on your terms. He reasoned, with substantial wealth and position, entitlement did work. But he had neither, and sitting at the bar, he realized he never would.
He had squandered his one opportunity at gaining it.
But his 1 year-ago self didn't know any of this. He applied for hundreds of graduate programs, professional programs, significant job titles, but he did not obtain a single one. There wasn't even a tease of one within his grasp. The rejection letters quickly mounted up, and his self-worth exponentially declined.
This started to affect his work. He now hated his dead-end job. He hated the salary. He hated the potential it teased. He hated his colleagues playing the game and succeeding in life. Rather than using it as a humbling experience, his ego shot him in the gut, and left him out there to bleed to death.
This was when that final domino of vices fell over. First came the drinking. Sure he had drank a lot during college, as everyone did, but now it had grown to the state of alcoholism. He was drinking alone. He was adding alcohol to his morning and lunch-time drinks. He was drinking daily. He'd often show up to work with a BAC of 0.1.
Then the smoking started. Cigarettes and weed became a commonality. He transitioned into cigars. That first cigar, a 7", 54-ga Churchill Romeo y Julieta Habana Reserve, was the beginning of his more recent persona. He viewed it as a symbolic entity, the irony of his status. But his sardonic sense of humor made him appreciate it, revel in it. His ego enjoyed the abuse. The adrenaline kick from the nicotine created in him a link between that image and a facade of happiness. The puff of smoke it elicited shrouded his true image, and he relished in this obscurity. So he chased it.
It was with this that he acquired a taste for scotch. Expensive scotch. Bottles he would normally spend months saving up for and use up within two weeks. Logically, this was also when his credit debt started to accumulate (exclusive of his already outrageous academic debt).
Then, 2 months before this night at the Obsidian, he saw an advertisement for a particular forum on a cigar aficionado website. An escort rating forum. He had never considered escorts or hookers or prostitutes, as he had considered himself an honest and virtuous man. But this was before his self-confidence was shot. Before he continuously struck out with desirable women. Before he could no longer elicit a returned phone call from a similar-minded woman. Before his moral ambiguity had lost all senses of rigidity.
He quickly realized his desire to frequent this site overshadowed his compulsion to check his email. This was also the first time he ever paid for a forum membership. He had to that day never paid for porn, but he was so entranced, he had to pay for this forum in order to gain further access in learning about escort services and finding the good ones. Most importantly, he paid it to learn of the explicit details of what the escorts offered.
Of course with his recent infatuation with image, he first scoured high end escorts. The $500+/hr types. The ones that look like models, carry themselves as successful business women, dress like orange county housewives, and fuck like porn stars (or so the claims on the forum would have you think). His initial reaction was to scoff at the ridiculous price, mainly because he couldn't afford it. But they were fucking hot. Hotter than any girl he had ever had a chance at (Ivy League girls aren't known for their towering beauty).
He then started searching for mid-tier escorts, the $300/hr types. They were plenty attractive, and still seemed down for serious business. His search into low-tier hookers (because they clearly make no effort to appear as escorts) revealed them as too unreliable, fake, and risky. His dive in morality stock was independent of his intelligence, and he knew better than to risk being arrested over a few hundred dollars. He may not have had confidence, but the ego still remained.
On his rare days of relative clarity, most often found when walking along the river to work, on days he had not had that first 9am drink, he started to ponder where he was headed with all this. It was Neo's rabbit hole, so to speak. But his own, dark, silk-lined passage. A yellow brick road paved with faux gold, into a thunderstorm. Towards a city of moral ambiguity. Where did it lead to next? Hard drugs? Violent crimes? Poverty? Republicanism? What next would he need to do to just feel
alive
? He knew his definition of alive was not correct, but it was the most appropriate he felt he could use.
And if he fell into that, when, if ever, would he be revived? Could he live a normal life, the suburban one with the white picket fence that had been picked out for him when he was just in high school? Would he gain the strength to rebuild his life? Would he even want to?
Scotch usually made those questions go away. Hence why he was drinking it now, finishing his first double and ordering a second at this bar in the hotel where he was to meet a woman he would pay for sex. For the opportunity for him to fuck her, and step onto the elevator to his hell.
He knew before he stepped up to the batter's box he had to learn the rules of the game. It was odd how he chose to play within these rules, an irony he never realized. A game that, under societal law, was explicitly illegal. But he still wanted to play, and play under their rules. He convinced himself that it was because he was afraid of the risks of getting caught. But in truth, it was because in this realm, he was not entitled to anything. He was not entitled to fuck her. In this world, outside of the principles of the real world, money and power did not entitle you to fuck her on your terms. Not at this high a stage.
He found several escorts who were rather detailed in their expectations of their customers. The usuals being: be clean, wear a rubber, don't talk about the money, present it in an unmarked envelope, and don't ask for explicit sexual acts until she initiates. One thing he was surprised with was the list of gifts these escorts preferred. He supposed that fancier restaurants now suggested a tipping scale, and so escorts would do the same. But buying a $500 piece of lingerie as a gift for a service that you are paying $300/hr seemed lavish. Then again, he realized he wasn't the usual client. He was only an imposter. He did not have wealth. To him, $500 did not equal a special gleam in a woman's eye. Especially, if he was only going to fuck her.
After a month of research, he decided he was going to pay one of these girls for their time of service. He picked one from the hundreds available. He looked at his savings, and cut back on his other expenses, to save up enough plus overhead. He also decided to buy a gift, to fit in with those other clients. He also wanted more than 1 hour, and figured all this would add up.
The girl he picked described herself as a voluptuous black woman. He had never been with a black woman, and thought this was the way to go. He typically was attracted to blondes, but he tried to let go of as much of his old ways as possible. The forum showed great reviews of this woman, saying she had an insatiable appetite for sex, that she was enthusiastic to suck cock, that she knew how to milk a cock with her pussy, and that she took it in the ass. Anal was one of things he never got to experience in college, and this experience had opened up that possibility. Ivy League girls didn't typically like anal, who knew.
Looking at her pictures, she was average height, with long, voluminous hair. The kind of hair a man wants to grab while fucking a girl from behind. Her breasts were large, a self-described 38D, with large, heavily pigmented areolas and nipples. Her erect nipples were magnificent; they nearly protruded out an inch. She had light stretch marks around her breasts. She carried some extra weight on her torso. Her stomach seemed like it would have a generous jiggle to it as she took cock. Her groin also carried fat, with a couple of stretch marks towards her belly button.
Her thighs were heaven, he had thought. Creamy, thick, smooth, with a hint of muscle tone underneath. He figured she could probably swallow the life out of a man with those massive thighs. Similarly, her ass was something he had never previously experienced. Plump, round, with a good jiggle to it. He even rubbed himself to orgasm just thinking about violating her ass from behind, using a picture of her bent over an office desk as ammo.
She wasn't something he considered a head turner. But she had this aura about her. She had confidence in her body, in her poses, her text. She had a passion for writing, and her prose oozed sexuality. She never wrote explicit erotica, but her mannerisms exposed an incredibly sexual being. She presented a persona that one would suspect hardly wore panties due to a constantly wet, aroused pussy.
He made contact by email, asking very courteously for a meeting the following week after work. He also used her code words for the VIP package (anal), because using her specific words were part of the game.
He received a response pretty quickly, and the date was set for the following Tuesday evening. In preparation, he made a run to the bank, withdrew the correct amount of cash (because other forms of payment were prohibited, obviously). He also visited a local branch of a high end lingerie boutique, and purchased an off-white lace babydoll set, with matching thong. He was excited for how she would look in it. Even on the rack, he could image her ass swallowing that thong whole and never look back.
The morning of, he received a text with the location of the rendezvous, and he had set out an hour early from work to arrive at the hotel, and to drink to calm his nerves. On the train ride there, he was nervous holding the gift, and felt the eyes of the other habitants of the train peering at him. He felt as transparent as cellophane. As he stepped off the train, he immediately spotted the tower of the Marriott Hotel. He walked in, and took a spot at the bar.
Half way through his first scotch, he received a text. It read: 'Sorry hun, plans got twisted. Gotta cancel tonight. Email me for another night.'
He read it twice. He was pissed. He was really pissed. His thoughts went silent. He could feel his face turn red. He could feel his forearm muscles tighten. His brain neurons simulated him throwing his drink at the wall in frustration. His body almost responded in a mimicking manner. He almost lifted his arm off the bar. Fortunately, his neurons processed the consequences quicker than his motor neurons could translate a message to his muscles. His self-perception and wallet thanked him for the restraint. Instead, he lifted the glass to his lips and gulped the scotch, dropped $30 on the bar and walked out.
On his way out the door, he again read the text to make sure the alcohol and nerves weren't playing a game with his mind. The contents were the same. He picked at the word "hun" with profanity. Was she trying to be a pleasant bitch? Was she trying to be professional in a personal way? Fuck her. Well, that was the point, right? He laughed to himself on his pun, and made his way straight to the lingerie boutique to return the "gift."
At home, he poured himself another drink, and immediately hit up the forum to find another whore. He was pissed, and he was going to fuck someone. But it wasn't that easy. Higher quality escorts weren't available on the dime to new customers, most listed that explicitly on their sites. So he gave up on his quest, and passed out after his third double, not even bothering to masturbate.
The next few days, he turned to a feigned sense of faith. He started to call the events of the previous night a sign. It was destiny making her cancel, because it was a huge mistake for him to continue. He was saved. The gods had given him a chance to right himself.
This thought barely lasted into the weekend. His shit job kicked his ass, and the bookmark for the forum was burning to be clicked. He swore his eyes were playing a trick on him; the letters in the web address were bolder than the other bookmarks. He found himself visiting the site again before Sunday midnight.
This time he argued he had saved enough money for the top-tier escort. He found one after some deliberation. It was like choosing one's first Ferrari.
She was a contrast to the first. She described herself as a thin, curvy French courtesan. She was 5'10", with long, wavy dark brown hair, juxtaposing her very lightly tanned cream skin. She had an athletic hourglass frame. Her breasts were just barely a B cup. Her nipples were proportional to her breasts, and tinted a matte oak brown. Her ass was a perfect handful, toned and muscular. Her pictures showed her in a variety of cocktail dresses, lingerie, and a nude pose of her backside, with her bent over and turned to look towards the camera with her hair hanging on her side. The camera loved her; there was no denying she had spent time as a model.
