A Shadow at The Biograph

Edited by Red_Sky_Reader

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Chloe snapped the straps on her thigh high stockings, adjusted her garter belt and checked her look in the mirror. She smiled that cheshire cat smile that meant she knew how good she looked and couldn't wait for her girlfriends to see her in her costume. They had decided weeks ago to take the Gangster Tour as a different way to spend the Halloween weekend and they were all dressing up as flapper girls from the era. A few of their boyfriends and guys from work were even dressing as real Chicago gangsters. Chloe thought it had been one of her better ideas. She looked at herself full in the mirror and admired her breasts through her silk dress. They were what the French would call perfect. Just large enough to fit in a champagne glass; small, firm and perky. She cupped her tits and caressed herself through the silk of her dress.

'God, I hope these see some action tonight... It's been too damn long!' she mused as she closed her eyes. The image of a strapping man 'taking her' raced through her mind as she teased and played with her nipples.

It had been unseasonably warm this autumn and she wanted to take advantage of the opportunity to show off her body. Chloe opened her eyes and gave herself one last go over in the mirror... She loved the 20's style dress she'd found last weekend at the thrift store, even if it was barely more than a teddy. It was black with silver lace, spaghetti straps and backless. The type that scooped the full length of her back, revealing a glimpse of the dimples at the top of her ass. Chloe secretly enjoyed the makeup stylings of that era, as well. She knew she looked good with dark eyeliner, bright scarlet lipstick and a sexy beauty mark. She added her grandmother's pearls as a finishing touch and walked through a light spray of Eau d'Hadrien before calling an Uber and walking out the door.

She had gotten to Chicago at the beginning of the summer and was thankful for her old college friends that she still had living in the city. Her new job had kept her busy and she had not met many new people, and thus far no men...at least none that were interesting anyway. Chloe longed for a real man. The kind of man she'd seen in the classic movies, not one of those tech geeks that spent their days in a cubicle but a man that knew what he wanted and wasn't afraid to take it! Her friend Susan had mentioned that her boyfriend Rob was bringing a friend that she might find attractive but she wasn't holding out much hope as the other blind dates and fix-ups, her well intentioned friends had attempted, turned out to be duds or head cases.

When she arrived at the La Salle Street Bridge, where they were to meet the tour group, a warm gust from the lake blew her perhaps too short dress up even higher. It gave anyone watching a good look at her ass and she drew attention from the boys gathered in front of a group of street musicians.

'Oh well,' she thought, 'better to start the night with some stares from strangers then to be ignored...' and at least it was nice to know that all her preparations weren't going to go to waste.

She exchanged hugs and greetings with her friends and made the obligatory new introductions before climbing aboard the trolley. Everyone looked great! They had all embraced dressing up and even the guys looked the part. Each historic site the bus stopped at was conveniently located next to a cooperating bar or nightclub, explaining the popularity of these types of tours. It basically amounted to a pub crawl with a gangster theme, which suited everyone just fine.

The first stop was Lottie's, a prohibition bar that still operated. Everyone was told the backstory about the rathskeller; a room in the basement where Al Capone, other mobsters and elected officials went to gamble. The room was known for horse racing, cards and strippers. After hearing the story about the 'girls' Lottie Zagorski had 'working' there in the 1920s, they were all given a shot of whisky and sent on their way. The next gangster stop was Jackrabbit's bowling alley, which had formerly been the clandestine brewing operation for the majority of illegal beer Chicago drank during Prohibition. The story was fun and afterwards they were ushered next door to the Publican, a trendy bar that had already started to bustle with its Saturday evening crowd. Everyone was having a great time! After two more gangster haunts and two more 'shot and a beer' joints, Chloe was happy to arrive at Goodbar, a quaint little bar next to the site of the St. Valentine's Day massacre. Chloe flirted with the cute but way too young bartender and ordered a vodka cranberry. She sipped her drink and stared out the window at the costumed Halloween revellers as they made their way from bar to bar.

'Great people watching,' she thought. Her mind wandered... Oh, how she yearned to be dominated by a real man: told what to do, ordered to please him, spanked! She wanted to be taken by a man who was filled with uncontrollable lust for her. She ached to be turned into his plaything.

"Hey Chloe, I want you to meet Ivan. He works with Rob at the Board of Trade."

She turned, smiled and shook hands thinking

'This one's got potential.' After an initial conversation she excused herself to go to the bar.

'Can't look too interested this early,' she thought to herself. The cute bartender was free at the middle of the bar so she leaned over the bar to flirt and try to see if she could make Ivan a little jealous. She could see Ivan in the mirror over the bartender's shoulder and her plan was working. After asking what his specialty drink was and flashing some cleavage she bent over the bar a little bit more giving both men a treat... she smiled a mischievous smile, 'just multitasking,' she laughed to herself. The bartender was wearing a pinstriped suit and gangster hat.

'Damn, is he cute!' Chloe thought. They flirted with each other for a while, making eye contact a bit too long at times.

'This is getting interesting,' she thought.

"Would you like to see the secret tap room where the mob used to store the money to be counted?" the bartender asked with a devilish wink. She thought a personal tour would be fun and would give her a chance to have some one on one time with the hot bartender. She was feeling the effects of those drinks now and was more than ready for a little action! Once they got out of sight of the others, their eyes met again and they both knew what would happen next. His shoulders were solid and broad, and his tongue tasted of cinnamon.

'Fireball,' she thought. Their kissing left Chloe nearly breathless! She broke away from their embrace and slowly began to undress him: first she removed his jacket, then she unbuttoned his vest. Chloe had gotten half his shirt unbuttoned when he ran his hands over the front of her silk dress bringing both of her niples to full attention. They kissed again deeply with her hand exploring his firm chest. Then he slipped his hand up under her dress and found her already moist. With his tongue pressed against hers, he slid her panties aside and began teasing her pussy. First moving over her swollen clit, then he teased the length of her slit before he buried his finger deep inside her hot pocket. Chloe gasped for air and let out a moan. His finger began pulsing as they kissed, slowly at first, getting her even hotter and wetter than she had expected. Just as she was beginning to grind to the rhythm of his hand they heard the trolley bells ring.

"Shit!" she said, "I've got to run... can't miss my ride." She left the bartender dumbfounded and drooling.

'Poor guy,' she thought to herself, 'He thought he was gonna get some.'

Chloe's friends cheered as she arrived back at the bus, joking that she'd be late for her own funeral.

"There she is." said Susan.

"Sorry guys, just needed to powder my nose." Chloe was flush and out of breath but everyone just thought that she was blushing about holding up the tour. Meanwhile, Ivan was checking her out from across the trolley when Susan mentions "He's not even the one I was telling you about. That one was stuck at the office, but don't worry, he just called Rob and said he's on his way. He'll catch up to us on the tour." Susan gave her a knowing smile.

Their next stop was the famous Biograph Theater where John Dillinger was gunned down in the alleyway just behind the auditorium. The group got a tour of the first floor and were told that the three million dollar renovation project had nearly been completed. In fact, they were going to be the last tour group to be allowed access before the theater re-opened next weekend. The guide told stories of theater employees throughout the years who had reported seeing unexplained happenings and some who had even claimed to have seen his ghost. The tour guide handed out flyers for the John Dillinger Museum in Hammond, Indiana as they were headed back towards the lobby. On their way out Chloe decided she really did need to powder her nose. She tried to retrace the guide's tour but got turned around looking for the ladies' room. She decided to see if she could find one upstairs and get a sneak peek at the second floor at the same time.

At the top of the spiral staircase there was an old fashion ladies' powder room, complete with a sitting area. Several 8 foot tall, framed vanity mirrors adorned every corner, backed by beautiful striped crimson and gold wallpaper. A bank of alabaster marble sinks lined one side of the room while plush, red velvet chairs and a chaise longue balanced the other.

'Impressive,' she thought.

She was just headed out when a shadow formed on the staircase in front of her. She quickly turned her head and saw a tall man in a dark suit appear behind her in the hallway.

"Oh shit! You nearly scared me to death."

He removed his hat. "I didn't know anyone else was here." he said.

"Oh... hey, you must be Rob's friend." Chloe said.

"My friends call me John."

"You know, you really shouldn't sneak up on people like that."

This one looked like trouble but, 'Damn, he's gorgeous,' she thought to herself.

"What are you doing here?" he asked.

After a pause, she said "The same thing as you, I suspect." Their eyes met. He was the confident type. Not the kind of man to look away. He had the sort of eyes that looked as if they had seen more heartache than happiness but still retained their kindness. She couldn't stand it one second longer.

"Want to show a girl a good time?" She said, surprising herself with the question.

'Oh well, fortune favors the audacious,' she thought to herself. He stared at her a moment longer, then John moved in closer and put his sturdy hands around her waist. He kissed her with a passion that caught her off guard. Her heart raced. The excitement was electric! As they kissed she felt herself being pushed backwards into to the ladies' room. They twisted and turned in a tangle of hands exploring each other's bodies. Before long her ass came to rest against the bank of marble sinks. He grabbed her hips and firmly turned her to face the mirror. Chloe felt John's hot breath on her neck as he commanded her to "Bend over."

He placed a hand in the small of her back and firmly guided chloe down at her waist instructing her to put both her palms face down on the countertop. She obeyed. She felt him step between her flats with his wingtips and push them out in each direction opening her legs. Her short dress began to ride up her round, tight ass leaving her feeling exposed and vulnerable while at the same time sexy as hell! She felt him step away. When she looked up at the mirror, she saw John eyeing her as though he was about to have his first bite to eat after being stranded at sea. Suddenly she could feel his right palm slip inside her left leg. He caressed her skin, producing goosebumps. He paused a moment before running his hand up her inner thigh. It came to rest at the natural crevice where her legs and ass met. His fingers stopped there for what seems like an eternity before he let his index finger explore the middle of her silk panties, stroking lightly up and down the full length of her pussy. Suddenly his strong, deep voice demanded to know "When was the last time you were fucked?" Chloe could not begin to think, let alone remember. Only a low moan managed to escape her lips. As he expertly teased her between her legs, Chloe's breath began to steam up the mirror.

"Push your ass in the air for me!" he commanded." Chloe did as she was told.

"Higher!" He called out before firmly spanking her ass.

"Smack" The feeling of pleasure and pain mixed as Chloe let out a squeal of pleasure that filled the room. John quickly returned his attention to Chloe's panties. Each stroke produced a quiver that ran through her whole body. The idea of being a stranger's plaything made her wet with desire. She cooed with every caress of his hand. The thrill was amazing but there was something else she wanted just as badly. She searched for the courage to ask for what she wanted...

'My turn' she thought and abruptly stood up and turned to face John. Just as he began to open his mouth to protest, Chloe pressed a finger against his lips and whispered, "I want an appetizer."

She let her finger drop from his lips in a line down his strong dimpled chin to the top button of his shirt. She proceeded to slowly unbutton each button with intent, deliberately making John wait longer than he liked. She finished the last button and opened his shirt revealing his rugged chest, rippled abs and a light line of curly hair leading down to his treasure. Her finger traced the path to the top of his belt. She delighted in driving him mad with anticipation. Chloe smiled as she preceded to removed the gangster's holster and six-shooter. She was surprised at its weight.

'He really went all-out with his costume,' Chloe thought to herself. She began to undo his belt and unbuttoned his trousers. Slowly... she unzipped him. His bulge sprang forward but was restricted at the last moment by his boxers. Chloe eyed her prize and released it from its restraints. His enormous cock stood erect before her, the tip glistened with drops of his sex dew. She chose to tease her man first. She stared up at him as she began lightly licking the tip of his cock. He tasted like a man should: a mixture of sweet and salty masculine sweat and earthiness all at once. Oh lord, how she loved the taste a man's cock! She gave John a mischievous smile before running her pursed lips the length of his rigid shaft, occasionally darting her tongue to make sure he didn't know what to expect next. The effect worked. John's manhood was throbbing by the time she gave him what he wanted. She swallowed the full length of his member. John groaned. She loved knowing she could drive her man crazy with desire! She could feel her pussy heat up and moisten every time his cock pulsed in her mouth. God, what she would give for a mouth full of his cum! She grabbed his firm ass and took his cock again and again, deeper in and out of her welcoming mouth.

"Good girl."

"I like you on your knees pleasuring my cock." He said with a smile. Chloe looked up and took his huge dick even further into her hungry mouth.

"Deeper!" He cried. "Daddy wants his little girl to take all of it in her pretty little mouth."

Chloe did as she was told. She grabbed his ass cheeks and slid his full member down her throat.

John moaned and just when it seemed as though he could take no more, she backed off and stared up at him with a smile that said, 'Your move'. John took the bait and extended an outstretched hand. He picked her up and carried her over to the chaise lounge. Chloe looked into his eyes as if to say 'What do you have in store for me now?' John lifted her higher and placed her down in the middle of the couch. Her dress already around her waist, John stared into her eyes as he proceeded to pull her panties down.

"Spread your legs for me!" He demanded. Her face felt flush and a hot rush of excitement shot through her body as she did what she was told. He pushed her thighs apart until her ankles touched either side of the chaise longue leaving her completely exposed. John moved to taste her, the tip of his tongue stroked gently over her waiting clit. She tensed and her nipples stiffened. Her senses tingled... the pleasure was electrifying! Back and forth he licked the object of his desire, teasing her mercilessly. Slowly his tongue traced the length of her moist twat. Then suddenly he plunged his tongue deep inside her, in and out, frantically tasting her honey. Chloe let out a gasp and allowed her head to fall back, enjoying the attention he was giving her. John's tongue explored every inch of Chloe's wetness. Closing her eyes, she let the euphoria wash over her.

"Good girl.' he said. "Spreading your legs like a good little girl for daddy."

Chloe purred with pleasure.

"Are you daddy's good little slut?"

A quiet "Yes." managed to escape her lips.

"What?" John demanded.

"Yes! God yes! I'm daddy's good little slut!"

'Take me, use me anyway you will, I want to pleasure you anyway you will have me.' she thought. Before long her breath quickened. Chloe's body began to tense up and then an overwhelming pleasure came rushing in, giving her a body shaking orgasm that caused her to quiver from her stomach to her toes. Chloe moaned in ecstasy. John smiled. He revelled in the pleasure he brought her fully, before pulling her up and redirecting her to the end of the couch. As he turned her to face the arm of the couch, Chloe caught their reflection in one of the mirrors.

'Damn, we look hot!' she thought.

John bent her over the chaise longue, her arms outstretched on the sofa. He moved her ass cheeks apart exposing her dewy wet cunt. The sight of her drove him mad with desire! He desperately needed to penetrate her but first he wanted her obedience. He let the tip of his cock explore Chloe's moist slit for a moment. He teased her cunt, stroking her with the throbbing head of his huge penis. Up and down he moved it over the length of her wetness. He inserted only the head of his long shaft inside her wet hole. He made her wait for a long beat... then he asked her.

"What does daddy's little slut want?"

"I want you." She said breathlessly.

"No! What does my little slut want?" He was driving her delirious with anticipation.

"I want daddy's cock!"

"Where do you want daddy's cock?" He teased.

"I want daddy's cock in my pussy!"

"Please daddy, please!" Chloe begged.

Then...with one thrust he was inside her, drilling her deeply with his manhood. Chloe moaned and let herself enjoy the excitement of the moment. She felt herself being pounded from behind and her moans grew louder. With each thrust of John's thick cock, Chloe was driven into the quilted side of the velvet couch. The power of his member reached deep inside her as she was forced closer and closer to the edge of ecstasy. She could feel herself getting wetter and wetter...it felt as if she could take no more. As she was driven over the edge, she cried out with pleasure. Her legs and body tensed; her fingers were outstretched and quivering. Flushed and breathless, she perceived only rapture. John had no mercy on her and kept pleasuring himself, thrusting deeper and deeper into her hot pocket.

"Is this what my little girl wanted?" He prodded her.

"Yes!"

"Yes!"

"Yes, this is what your little girl wanted! Make me do anything you want!"

"Make me your little slut, daddy!"

"Please daddy, please!"

"I'll be a good girl, I promise!"

He was relentless and Chloe's vision began to go slightly dark. She neared the edge of consciousness but the bliss was like nothing she'd known before. All she could do was enjoy the thrill of this new and powerful sensation. She was aware of John growing louder and louder, increasing his speed and thrust.