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.
