The Alderman
Cliff Bradley was one bullet short of making the Chicago Daily News obits in the summer of 1930. He had gotten tangled up with the mob who got itchy about a bundle of misplaced cash. They wanted it back. It turned out that 10K had been stolen by a teen-age hooker who considered it a tip. Unfortunately, the Chicago outfit didn't see it that way. They terminated both their disagreement and her in the customary way, the mob's way.
Lots had changed since then. Alphonse Capone was out of prison after serving an eight year sentence for tax evasion. Ed Kelly was serving his third term as Chicago's mayor. FDR was serving his ninth year as President, and the Japs had rearranged Hawaii the year before.
But not everything had changed in the Windy City. The Cubs hadn't won a World Series since 1908. Chicago alderman still accepted bribes and were the grease that kept the Democratic machine running smoothly. Corruption and vice were still on the menu giving a private dick like Bradley a steady stream of clients.
Cliff's secretary, Stella, who he called "Songbird," had left after marrying a piano player. Currently, she and the piano man were doing gigs at Capone's old hangout, the Green Mill. The Mill was now a dive patronized by drunks and addicts, but it was steady work for Stella whose voice matched the surroundings.
Stella's replacement wasn't much as a secretary except for her looks. He agreed to hire her more for decoration in his drab third floor office than her inept typing skills. "Ditzy" is what he called her. She called herself Loretta.
Loretta was the eighteen year old daughter of an influential family in Alderman Reilly's forty-second ward. She first met Cliff on an urgent private matter and the alderman had been anxious to help the family. That's what an alderman does in Chicago if he wants to be reelected.
Loretta was nervous but not shy when she waltzed into Bradley's office that first day. She wore a snug fitting blouse that emphasized every sumptuous curve and a knee high skirt that wrapped around her hips held precariously by two scarlet red buttons. Loretta wore bright yellow barrettes on two blond pigtails, looking like the cute ceramic doll Cliff had seen in the Marshall Field's window.
She needed help with an abortion. It wasn't for her, she said. It was for a friend who got knocked up by some kid from Bridgeport. Cliff said he didn't do doctor referrals. She pleaded for his help. He told her abortion doctors weren't exactly advertising in the Daily News' Personal Ads. She shed a few crocodile tears. Cliff needed to be persuaded.
Loretta was good at persuasion. Cliff's Achilles' heal was that he could be swayed by a persuasive female. He was weak that way.
After a few more fake tears, she loosened her blouse as her next attempt to change Cliff's mind. He gave her his best poker face as if he hadn't noticed. Cliff was good at negotiating deals.
Loretta unhooked her bra and let it fall to the floor. Cliff loved the view but waited for a better offer. She undid the two red buttons letting her skirt unwind from her tight ass. She was playing him like a Stradivarius. He liked the music and his cock was now doing the dealing. She sat on his desk slipping off her panties, spreading herself open like a slow yawn. She smiled when he unzipped his pants, letting them encircle his ankles.
She licked her lips while watching his hard dick twitch with excitement. It reminded her of a dog's tail when it's begging for attention. Loretta knew she had won even before he thrust himself deep inside her wet youthful cunt.
The transaction was signed, sealed, and delivered the moment he ejaculated inside her with the repetition of a machine gun. Cliff had no worries about getting the girl pregnant. By the look of things, her sensitive breasts and darkened areoles made it clear to Cliff that the Bridgeport boy had beaten him to it.
"Gosh, Mr. Bradley, that was quick. Do you always close a deal that fast?"
"Only when it's urgent business," Cliff answered.
"So we have a deal, right?"
"Yes, we have a deal," he affirmed. It was the kind of deal he didn't mind losing.
Loretta returned to Cliff's office a few days later. Bradley gave her the name and number of a practitioner specializing in shady medical procedures. She kissed him and suggested they meet again. She said she liked the way he did business.
That was the only time Cliff fucked Loretta. Not long after, Alderman Reilly called thanking Bradley for his help. The alderman had another reason for calling. He wanted Cliff to hire Loretta as his secretary. You don't turn down a Chicago alderman.
She showed up the next day with her purse and a scent that put him in the best mood he had been in since Songbird left. The bad news was he wasn't going to fuck her again. He knew better than screwing his secretary after Songbird ran off with fingers.
Loretta's most valuable personal belonging was a compact mirror that was her constant companion. Cliff was certain he heard her in the outer office whispering, "Mirror mirror, who's the fairest of them all." She was vain that way.
Loretta had been pecking at Cliff's typewriter since the fall. She could now do it with two fingers, and it was December. Winter in Chicago is an import from Canada, sent free of charge. This December day was a Canadian special. The winds howling off the lake were as treacherous as a Nazi Blitzkrieg carrying enough snow to cover the Tribune Tower up to the thirteenth floor, if it had one.
Ditzy called in sick with a cold, the kind of cold that penetrated your skin as if you were naked in an ice cream freezer. She wouldn't be coming in on Monday. Going AWOL wasn't unusual for Ditzy, especially after she had been shacking up with a guy for a one night stand. Ditzy might have been vain, but she wasn't frigid. Sex came only second in importance to her mirror.
The streets below on this bitterly cold Sunday were so quiet you could hear a clock ticking in the apartment across the street. Loretta's absence didn't matter to Cliff and clients were unlikely to be calling unless they wanted him to shovel their driveway. He would sleep in his office as he often did. Cliff wasn't alone on those occasions. A radio, a bottle of Scotch, a carton of Chesterfields and his .38 heater is all that he needed for company.
In the afternoon, he switched on the Bear/Chicago Cardinal game. Toward the end of the third quarter, it wasn't going well for his beloved Cardinals. Cliff turned it off when the phone rang. It was Molly, the madam he knew from the upstairs bordello at a speakeasy that Bobby Farrell ran during Prohibition. Only by 1942, the speakeasy had closed along with her whore house.
Molly was still in business having found a new location in the western suburb of Berwyn. It was once a family owned hotel back in the thirties, but time had passed it by. She purchased it as shrewdly as the Dutch buying Manhattan. Molly called her whore house, "The Birdhouse." Downstairs was a tavern. Upstairs were the rooms. Cliff had made a few social calls when it first opened. He liked the place better than Farrell's speakeasy. It was less dangerous as long as Molly continued to pay off the cops. And the girls were prettier and young. Molly's girls were Poles and Czechs who had left Europe just before the war started. They were the lucky ones.
"Cliff," she barked on the other end, "I've got another delinquent who refuses to contribute to the Orphanage Home. I need some help with this guy."
"You mean he didn't pay the girl."
"I mean he didn't pay the girls. This was the second time. He wanted a threesome last week with two of the girls. That was fine until he told them he would pay at the bar. He didn't and walked out without touching his wallet."