Private Dick

Jack Cassidy slipped the depot agent a fin. "I'm sure you can get me in a sleeper on the rattler to New York." The agent quietly took the money and checked the massive ledger in front of him. Adjusting his spectacles, he tapped an entry in the book.

"Well, Mr. Cassidy, we have one berth available on the train, but Mr. Gutman asked for privacy on this trip."

Jack stared hard at the agent. Normally it wouldn't have been such a big deal to wait for the next train to New York, but he was paid to do a job and that job required him to be in New York as soon as possible. Jack pulled out his wallet and slapped down three big ones on the agent's book. "I cannot stress how important it is I'm on this train."

With a practiced deftness, the agent palmed the bills and made a mark in the ledger. "I'm sure Mr. Gutman wouldn't mind having a bit of company on the trip." The agent made out the ticket and handed it to Jack Cassidy. Jack nodded and turned away from the counter. Taking a few steps, he stopped when he noticed a beautiful woman. She was dressed in a white jacket, which flared at her supple hips and framed her ample bosom. Her hat rested at a precarious angle was neatly pinned to her piled chestnut brown hair. Her mid-length white skirt fit tightly to her long shapely legs. She held an unlit cigarette and her handbag in one hand as she rummaged with the other looking for a light.

Jack flicked his zippo and offered the flame to the damsel. She looked from the flame to his face and smiled before lighting her cigarette. She took a deep drag and blew out a white stream of smoke. "Thank you very much," she said.

Jack clicked the zippo closed and tipped his hat to her. "It was my pleasure," he responded. Without another word her walked down the long corridor to the trains, swinging his small case in his hand and whistling a little ditty.

On the train, the porter directed Jack to the sleeping car. Jack dropped a few bits into the porters outstretched hand. He sized up the empty compartment. Two bunks currently lifted and locked against the compartment wall, a moderately comfortable bench and a window, overlooking the milling crowd on the station platform. Jack hung up his hat and coat. Reaching into his jacket he removed his heat and slid it into his case and pulling out the Tribune. He stowed the case, sat back on the bench and flipped to check out the box scores.

The door of the compartment crashed open to reveal a nebbish little man clutching a satchel to his chest. His suit was rumpled as if it had been slept in, several nights in a row. The man looked stunned as his eyes fixed on Jack. "Who are you?" he asked, his voice revealing just how high-strung he really was.

Jack reached into his pocket and pulled out his deck of Lucky's. Freeing a cigarette he offered one to the man. "Gasper?" The man merely shook his head standing in the door. Jack could sense this was a man on the run from something or someone. "You might want to close the door, that's if you aren't interested in attracting attention to yourself. I'm Jack Cassidy, your bunkmate."

The man stepped into the compartment, wary of Jack, but not wanting to have his back out in the open. He closed the door. "That can't be, I paid extra to be alone."

"They overbooked, had no choice but to put me up with you. I'd get a refund if I were you." Jack lit his cigarette. "I take it you are Mr. Gutman?"

"Sherman."

"Come in, have a seat. Looks like you could use a rest."

Sherman plopped himself down on the cushioned bench next to Jack and slouched. "How far are you going?"

"All the way to Dodger Stadium. You?"

"To the end of the line," Sherman said his voice flat.

The train whistle blew three times and the train began to slowly move. Jack stood. "Looks as if you need some time to get yourself together. I'm heading to the lounge car. If you come out, I'll buy you a drink."

Jack Cassidy walked through the narrow corridor once more until he reached the lounge car near the rear. The lounge car was already filled with travelers weary of the journey that had just started. Behind the bar a portly man with a handlebar mustache poured fingers of whiskey and told a few ribald jokes. Jack noticed a woman sitting at the bar. She wore the dress of a working girl, a railway can-can. Her golden tresses hung loose and her face was painted like a canvas of a Dutch Master. She rested her chin on her hand and her elbow on the bar. Her other hand absently stirred a cosmopolitan. Jack couldn't resist a pretty face, and even if she was wearing a price tag, it never hurt to window shop.

"Is this seat taken?" Jack asked, setting his hand on the stool next to her.

"Hello, handsome, seat yourself right down. What brings you to leave Chicago?"

Jack sat on the stool and ordered a bourbon from the bartender, "and whatever the lady wants." He looked into her alert, bright blue eyes and saw the fresh faced youth from some country town, beaten by the city, but not broken, yet. "I have business in New York."

Her eyes sized Jack up quickly. "Family business or dick business?"

The bartender brought him his drink. He lifted it in a silent toast to her and sipped. "There ain't nothing wrong with your peepers. I've got the gumshoes on; I'm a private dick. I didn't think I would ever be considered for a mafia type."

"I wouldn't have thought so either, but I know Raymond the Tooth is on the train."

Jack set his drink down and thought a moment. Raymond the Tooth wasn't exactly near the top of the family, but he had a street reputation. Not only was he gifted with the ladies but also he had a cast iron heart. The man could watch his own mother dance on a rope and not feel any sorrow.

When Jack didn't say anything she continued. "You aren't wrapped up in that, are you? I've spent enough time in Chicago to know to stay clear of 'the Tooth' and his Bruno. Say, bo, what's your handle?"

"Jack, Jack Cassidy. And what does a dame like yourself go by?"

"Carmen Mars."

"You work this line a lot, Carmen?"

"For a year, now. Chicago to New York can be a lonely 42 hours for many men. Will it be a lonely trip for you, Jack?"

Jack smiled and finished his bourbon. He noticed Carmen hadn't had but a sip of her drink since he had sat down. "You aren't much of a drinker, are you?"

"It pays to keep your wits about you, or else you may find yourself planted in the railroad bed. Its good advice for anyone on this rattler."

Jack looked up just as the woman in white stepped into the lounge. He heard Carmen softly declare the presence of trouble, but he wasn't paying that much attention. The woman in white had him enthralled. "Pardon me, Carmen," Jack said as he stood from the stool to approach the woman.

"I'll be here," Carmen said with a high degree of confidence.

Jack sidled his way over to the woman in white. "May I buy you a drink, Miss?"

"Well, if it isn't my hero of the moment. I'd be delighted if you would buy me a drink. I could certainly go for a champagne cocktail."

She took a seat in a booth and waited for Jack to return. "Will you join me, Mister… oh dear, I can't believe I've accepted a drink from a man I don't know. Please remedy this awkward moment for me and save me yet again."

"Jack, Jack Cassidy," he said as he sat in the booth.

She offered her dainty white hand to him, "Iva Vargas."

Jack took her hand, not knowing exactly what she expected him to do with it and shook her fingers lightly. She chuckled.

Jack looked into her brown eyes and smiled from their warmth. "Where are you off to, Iva?"

"I have a cousin in Baltimore I'm going to visit. And what of yourself, Jack?"

"I've got a little business to attend to in New York."

"Well, then, it looks like we have some time to get to know each other. Would you like to move to someplace quieter? Your compartment maybe?"

"I would love to, but I'm sharing it with a real nervous bloke, well, speak of the Nick himself." Jack looked up to see Sherman, still clutching the satchel enter the lounge car.

"That's him? How fortunate. Let me go freshen up." Iva stood and walked past Sherman to the door leaving the lounge car.

Sherman spotted Jack and took Iva's seat. "About that drink . . ."

"I've got you covered, Sherman. Glad to see you leave."

"I had to use the restroom," Sherman said.

Jack signaled the bartender for a bottle and then turned to Sherman. "What you need, son, is to relax. Whatever has you this tense can't be dealt with if you have the jitters. I think I know what will help. Stay here."

Jack got up and walked over to Carmen how was explaining the nature of her presence to a rube who still wasn't clear on the idea. With typical Chicago manners, Jack cut in front of the straw-chewer and set a bill in front of Carmen. "See my friend, there, he needs to relax. Go ahead and take this bottle to him, and make him feel relaxed." Jack looked at the c-note on the bar and dropped another on top of it. "Real relaxed."

Carmen smiled, but only slightly. "You got it." She took the bottle he had gotten from the bartender and sauntered over to Sherman. Jack watched her fine curves. Her heart-shaped ass swaying with each step made every man gape like wolves at a chicken ranch. She settled in next to Sherman and began whispering to him, pawing him, and doing everything in her power to make him feel like he was the center of the universe. It worked, as it would work on most men. A woman who focuses her charm and intelligence against a man's ego will always win. Soon they got up and left, heading to Carmen's compartment where she would be able to keep control of the situation.

Seconds later Iva Vargas returned. Jack met her near the door. "Where did the little fellow go?"

"I made sure he had something to do for a few hours. Shall we?" Jack opened the door for Iva. She looked about the bar for a brief moment but then followed Jack's lead. The two walked through the narrow corridor; being compressed once as a large 6'7" black man, dressed in a tuxedo passed them the other direction.

Jack looked at him for a second and then after he had passed recognized who it was. It was Quentin "Knuckles" Parker, the championship boxer accused of throwing a fight. The fact was immediately lost as he refocused on the luscious brunette walking in front of him. When they arrived at the compartment, Jack opened the door for her and she entered.

"Quite a cozy little nest you have here," Iva said as she unpinned her hat from her hair.

Jack took her by the arm and stepped close to her. She was a few inches shorter than he was; so she had to look up at his granite jawed mug. "I'm sure you have a cozy little nest of your own." He pressed his lips against her full moist lips and kissed her. Their kissed turned into a torrid embrace. Iva started pushing Jack's jacket off his shoulders. Clothes began dropping to the floor left and right. With a bit of fumbling, Jack was able to lower the bottom berth. He fell back onto the bunk as Iva performed a subtle striptease. She let the rest of her outer garments drop until she was standing in front of Jack in her white bra, garter, panties, stockings, and dangerous stiletto heels. Jack responded with a generic, "You are amazing."

Iva draped herself onto the bunk. Jack eagerly cupped one of her breasts as he kissed her. Her nipples hardened at the slightest caress and she gasped as his thumb and forefinger rolled the fleshy nub underneath her bra. Soon, he had freed her breast and set upon it with his mouth.

Within minutes he had Iva writhing. His fingers delicately stroking her clit in her panties and his mouth sucking on her large tit. A skilled hand unclipped Iva's garter from her stockings and rolled her panties down her leg. Jack kissed her breast and began kissing her delicate flesh down across her navel to her heated, wet crotch. No words were spoken as his fingers began to explore her moist crevice and his tongue found the hardened mark.

She smelled of earthy gardenias, a sweet very carnal but pleasant smell. With an animalistic growl, he set upon her thick bush, lapping at her feminine ambrosia. His fingers forcefully thrust into her womanhood compelling a lustful moan from her. Jack licked from her moist hollow to her throbbing clit, several times before wrapping his thin lips around her slit and giving it a gentle suck and lick. He kept his fingers in constant motion, which translated in a constant action from her hips and waist.

"Mmm, Jack, that is wonderful. Oh, god, harder, I need you, I need your cock," Iva said in a near constant stream between gasps and moans of pleasure.

Jack was already iron hard. His cock needed some stimulation of any kind. With little effort, he shucked his trousers to the floor along with his underwear. Her raised himself above Iva's prone form and guided himself into her hot, moist channel. As he eased himself inside her, Iva raised her knees, clutching Jack tightly. "Fuck me, fuck me like I'm your first!" Iva demanded.

Jack complied. He was enraptured by this woman - this woman that embodied all the elements of desire for him, whom he met a mere three hours before.

The clickety-clack of the train against the track and occasional blast of the whistle were the only sounds heard over the grunting, moaning, and sounds of pleasure coming from Jack and Iva. The train ran through a small town, blasting its whistle all the way just as Jack brought Iva to her first orgasm. She shrieked with pleasure, her body seizing and relaxing several times.

Jack was still fully aroused. He took this opportunity to set his thick penis between Iva's sizable breasts. Nary a word passed and Iva had laced her fingers over her tits letting Jack fuck her fleshy mounds. Jack Cassidy was close to cumming and Iva sensed it. She pushed him back a bit, sat up, grabbed his member and began pumping it over her mouth.

The laconic detective bit down and from clenched teeth muttered, "Oh, sweet Jesus, here I come." His seminal load blew into Iva's mouth and onto her chin, a second contraction dribbled cum onto her chest. Without hesitation, Iva scooped the fluid into her mouth and gently grabbed Jack's tiring cock to lick off the excess from the tip.

Sherman and Carmen entered Carmen's room. It was dark and Carmen left the lights off.

Carmen led Sherman to the bench in her compartment and encouraged him to sit. Within seconds she was on her knees in front of Sherman, her hand stroking his flaccid member beneath the thin fabric of his trousers. Some life was being worked into the limp cock, but Sherman seemed focused on something else.

"Do you have a girlfriend?" Carmen finally asked.

"I do. Her name is Shelly, Shelly Bush."

"Love her?"

"More than anything."

"More than getting a blow job from me?"

Sherman hesitated and dropped his head. "Yes. She means the world to me. I don't know what I would ever do without her."

Carmen stood and sat next to Sherman, taking his hand in hers. "Tell me about her."

"She's wonderful. Optimistic, though a bit naïve," Sherman waxed romantic. Carmen listened to him tell her about the darling young girl he had met in the office who saw passed his less than charming exterior. She fell in love with the man she knew Sherman could be and that was when he knew he had to make some very dangerous decisions. "See, the man I work for, Raymond Brugella, is not a good man at all. He has been dodging his taxes for five years. I have the proof and I knew in order to be worthy of Shelly, I needed to do the right thing."

"Raymond Brugella? Raymond the Tooth?" Carmen asked, alarmed.

"Yeah, that is what his associates call him."

"I know of him. You know he is on the train, right?"

Sherman shot up from the bench. "What! That can't be! How could he have known? The whole plan is ruined!" He paced in the short compartment, fretting about his situation.

Seeing him become more frazzled and how she was paid to relax him caused Carmen to slip into ultra seductress mode. Without a word she dropped back to her knees, undid Sherman's belt, dropped his trousers and took his soft penis into her mouth. Within seconds, Sherman was hard and enjoying the feel of Carmen's mouth along his long shaft. Carmen kept pumping her mouth up and down his cock, her hand gently caressing his balls, her golden hair brushing against his legs. Even in his state of distraction, Sherman couldn't hold back his orgasm. Carmen drank down his cum in a few quick gulps, not losing a drop. A few more pumps with her hand and a kiss temporarily released Sherman from his stress.

The train slowed in the night to pull into a lonely station. Waiting at the station was a young woman, dressed in a beige outfit complete with a matching hat and gloves, holding a small case by the handle with both her hands. The porter helped her aboard and another took her ticket. The pretty young lady in her early twenties, reddish blonde hair, perfect hourglass figure, looked nervously about the train. She spotted another porter and asked the kind man, "If I were looking for someone, where would I begin looking for 'em?"

"Well, Miss, if I were you, I'd start in the lounge. Everyone eventually finds themselves in the lounge car, it is in the back of the train this'n way."

"Oh thank you very much," the lady replied.

She walked to the back of the train and entered the smoky lounge car. She couldn't see whom she was looking for so walked up to the bartender. She still carried her valise with her. "Excuse me. Excuse me, sir." It took a moment to get the bartender's attention.

"What can I get for you?" He asked, twirling the tip of his mustache in admiration of the virginal beauty in front of him.

"Oh, nothing, I'm wondering if you could help me."

"I'd love to, but I don't get off work for another two hours."

"Pardon? No, I mean, well, I'm looking for a man by the name of Sherman Gutman. Has he been in here?"

The bartender looked at her with a straight face even though he wanted to laugh. "Listen, Miss, I get many guys in here a night and they all look the same to me. None of them are real eager to give me their names."

The woman looked crestfallen. What she didn't notice was a handsome man sitting near the bar with a large black man in a tuxedo overheard her. He stood and walked up to the woman. "I believe I can help you, Miss? Pardon me, what is your name?"

"Shelly Bush."

"Ah, yes, Shelly. Sherman has spoken dearly of you. I happen to know where he is. Was he expecting you?"

"Oh, no, not at all. He said he might be in trouble. I was visiting my Mom and I knew what train he was booked on. I wanted to stop him before he did something foolish." Shelly looked up at the man with an amazing amount of hope in her eyes.

The man waved to the large black man he was sitting with. The massive muscled man dressed in a dapper tuxedo approached. The first man spoke, "This is Shelly Bush, she came aboard hoping to find Sherman Gutman. Would you escort her to my compartment." The man turned to Shelly, "I'm Raymond Brugella, an associate of Sherman's."

Shelly's eyes widened in disbelief as the hulking ex-boxer forcefully grabbed her and dragged her through the train. Few people paid any attention. Raymond followed close behind.

"This is my lucky day, Shelly. You've given me the perfect bargaining chip with Sherman, and a bit more," he added with a lascivious smile.

Jack Cassidy lay in bed on his back smoking a cigarette. Iva Vargas rested her head on his barrel chest listening to the thrumming of his heart.

"You are quite a man, Jack Cassidy."

"And you are quite a woman."

Iva brushed her fingers across Jack's firm torso. "When do you think Sherman will be back?"

Jack crushed his cigarette into the little metal ashtray on the wall and grabbed Iva by her lustrous brown hair, lifting her head up. "I don't recall giving you his name?"