Lawyer or banker for sure. She could not dawdle. While the bartender would get his 10%, she could not afford to have the concierge walk in. That would be an extra 10%, which she did not like to pay unless he steered a guest to her.
It was easy enough. He had a wedding band on and he was sitting alone at a hotel bar on a Tuesday night a couple of weeks before Christmas.
After a few words of sympathy—generic words of sympathy since she did not know why he was sitting at the bar—he finished his drink. She whispered “One thousand” in his ear, and he did not blink. He nodded.
Within less than fifteen minutes of her first seeing him, they were in his room. It was a nice, upper-floor suite. There was not much light, but she had the chance to look at him. He was handsome. His hair was dark brown, cut short but not super short. Traces of gray gave him gravitas. His whole manner gave him gravitas.
After he handed her ten fresh one-hundred-dollar bills—he was “prepared” for this—she went to the bathroom to take care of some things. She brushed her teeth and reapplied her lipstick and ended by dabbing perfume behind her ears and in her pussy. She left her panties on so he could remove them later. If he chose.
When she returned, he was still in his suit. He sat in one of the armchairs that were angled out for a view over the Lake. He had gotten a scotch from the minibar. He asked if she would like something, but she declined. The room was nicely if conventionally furnished, and the only light came from a tall lamp near the desk by the window.
She was twenty-nine. About five-seven. She was long-limbed with light-brown hair, which she wore slightly loose so it just passed her shoulders. Very simple earrings and one piercing along her right eyebrow. She was relatively flat-chested, but wore a push-up bra to enhance what she did have. She was tall and thin with an oval face. She had a bachelor’s degree from Marquette and a master’s from the University of Chicago. Her day job was working for a bank. Tonight she wore a scarlet dress with black pumps, beneath a faux-mink jacket as a concession to the Chicago cold. She had an apartment in Lakeview.
By then she knew, from the conversation in the elevator, that he was a big-deal lawyer from San Francisco. He emphasized that he was not married “civilly.” She figured he was Catholic. Still wore the ring. With his glass on a side table, she bent down towards him. Her tongue traced his lower and then his upper lip. His hands remained on the arms of the chair but she heard a slight wanting from his lips.
She unbuttoned his jacket, and he leaned forward so she could remove it. She folded it gently and placed it on another armchair. She returned and bent down so her tongue could again caress his lips as she loosened and removed his tie and undid the top buttons of his expensive shirt. With the tie in her right hand, she bent down to kiss the flesh she exposed by her unbuttoning. And again a moan. He gave just the slightest hint of being excited.
After folding the tie delicately and placing it by the jacket, she undid his belt. He got up so she could unbutton and unzip his trousers, and she pulled them down. She took each of his shoes off so she could remove his trousers. He sat back down, and she again bent her face to his, this time using her tongue to induce him to open his lips slightly, and then her tongue entered his mouth and became engaged with his tongue. She could taste the scotch. Now his moans were clear and his hands were no longer on the arms of the chair. They reached round to her waist, pulling her towards him as she awkwardly tried to remain standing.
Her left hand dangled down to his briefs and found his flaccid penis. It was not a dick. It was not a cock. It was a flaccid penis. All the rest of him was aroused except for his penis.
He would need managing. She moved from his lips and stood in front of him. Her hands reached for his briefs, and he lifted his ass so she could remove him. The penis was more pitiful when she could see it, lying there next to a pair of hairy balls.
She saw it often enough. Sometimes she can get it to harden. She placed her lips on it, lifting it to her mouth with her hand. After several attempts, she licked it. Slowly running up its bottom, but it remained as it was.
“Fuck.” It was him. His hand pushed her head sharply to the side and he grabbed it, trying to get it going. After ten or so strokes, the futility was clear to them both. She stepped back and reached around to unzip her dress. Maybe that would stimulate him.
“Don’t bother. Just go.”
It was easy money, but she always felt a little sad about men like him. She did not feel bad about the money; he could afford it. A headcase. It was a sentiment she did not dwell on. Her livelihood—at least the livelihood that allowed her to pay for things she could not on a banker’s salary—would not allow it. They were all pitiful.
She got to the lobby and avoided the concierge as she walked the four blocks to another of the hotels she worked.
Back in his suite, William Nelson, Esq., remained in the armchair. It happened once before, but that was only when he was trying to jerk off. Surely a high-class whore could make it work. And she had not, beautiful as she was. Desirable as she was. And he desired her. His whole body did except for the one that mattered. He sat on the chair, his right hand idly stroking his useless dick—penis—as he used the left to hold his glass. It was no use. He finished the drink, and naked except for his shirt, he went to the bathroom and put on his pajamas and mindlessly watched porn on his tablet until he was tired enough to sleep.