Lady of the Windy City

The night was cold as usual for a Halloween in Chicago. The chill air whipped through the downtown streets like a dervish, pushing and blowing the travelers and revelers around like rag dolls. It wasn't anything new, and any Chicagoan would find the night disappointing without the cold wind and constant threat of rain. It made the night seem sinister and dangerous, the perfect night for Halloween.

Women wearing the most skimpy and scandalous costumes they could find and men drooling wolfishly after them filled the dance clubs. Every store, bar and restaurant decorated for the occasion and offered Halloween versions of whatever they sold. You could find a 'Devilishly good' cigar at a smoke shop, or drink a 'Dracula' Bloody Mary. For one night every year Chicago stopped being the Windy city and become the Scary City.

The W Hotel was no different from any other business in the City. Orange and purple lights decorated the hotel, while skulls and the lurking shadows of witches peeked around every corner. The Manager of the hotel dimmed the main lights and everyone enjoyed the faux-frightful atmosphere.

Melissa sat at the bar and sipped a vodka martini. She wore a short black cocktail dress which showed off her shapely legs and firm breasts and made her impossible to ignore. Her short black hair framed her face like the lustrous feathers of a raven, and her plump red lips attracted both men and women. A few young men in the bar had sidled up next to her, trying to gain her favor, but Melissa had already decided on which man would take her up to his room.

The man Melissa had set her sights on would have surprised the other patrons of the dimly lit bar. He sat at one of the small corner tables, quietly eating dinner while enjoying a drink and reading e-mail on his phone. Melissa judged that he was in his fifties, but was still in good physical shape. Though not what she would call handsome, he wasn't unattractive either. If asked, she would have described him as plain or average.

Melissa found the unremarkable nature of the man his most appealing feature. He wore a dark blue suit that was neither expensive nor cheap, and even though his phone wasn't the latest model, it wasn't old either. His ring finger was bare, so he probably didn't have a wife. She had watched him for almost an hour and he had not made or received a call, which was a good indicator that he didn't already have a woman in his life.

All of these observations helped Melissa form a fast opinion of the man. He was a single man with a middle management position and with little excitement in his life. This meant he probably had disposable cash and credit cards. He would be another perfect score.

At twenty-four years old Melissa was a successful call girl and con-artist. She was a smart young woman and had quickly learned the easiest way of making money was the worlds' oldest profession. She knew exactly what to look for in a client and targeted those that would easily part with their cash in trade for her attention. Unfortunately, thanks to a little drug-spiked drink most of her clients slept all too well after getting what they paid for. When they awoke they found their money and credit cards missing and under the circumstance were unable to engage the local police.

Many would say it was a shame that such a bright young woman had not found her place in a more respectable occupation. She kept notes on where and when she met her clients/victims, and made sure to find out as much about them as possible. If she had scammed a man who was attending a dental convention, she made sure to stay clear of the sort for months. She changed her hair and appearance often, transitioning from brunette to blond and then red head often. Her thoroughness would have taken her far in the business world.

Melissa watched as one of the waitresses stopped by the man's table. She dressed like Little Red Riding Hood, with a short red dress, white stockings and a small basket dangling from one arm. Melissa watched as the waitress did her best impression of the famous fairy tale character, asking if the man needed anything else. When she left, Melissa watched as the man's eyes lingered over the girl's body. He wasn't obvious about it, but it was clear that he liked what he saw.

Melissa waited until the man had almost finished his dinner before she made her move. She ordered a fresh drink and then walked over to his table.

"I don't mean to disturb you, but I was wondering if you could help me?" She said.

"It's no problem. How can I help you?" He replied, placing his knife and fork on the table.

"Do you mind if I sit with you for a while? My friends are late and some of the men here make me a little uncomfortable." She explained with a tone dripping with distress.

"Sure, take a seat." He said.

Melissa sat down in the chair opposite of his. She introduced herself as Holly, and he introduced himself as Steve. She found out that he was in town on business and wouldn't be leaving until the morning, but that was all. He quickly returned to eating his food, apparently believing he had fulfilled his obligation by allowing her to sit with him.

Melissa soon became annoyed that he was ignoring her with such ease. She slid her hand down her stomach and tugged on the front of her dress, pulling the thin material down to reveal more of her cleavage. She coughed to catch his attention, but after a quick glance he resumed reading whatever was on his phone.

The waitress returned to ask about drinks, and as before his eyes lingered over her as she walked away from the table. Indignation and anger raged through Melissa as she watched the waitress. The young woman was cute but that was all. Melissa knew that she was better than the waitress in every way, but her prey wasn't giving her a second look.

Steve finished his dinner and was enjoying his drink, and Melissa knew that she didn't have long to reel him in. Simply offering him sex for money wouldn't work. She thought it over for a moment and pretending to receive a call pulled out her phone.

"Hey. Where are you guys at?" She said to the silent phone.

"How long will that take? I don't know anyone here and it will cost a fortune to take a cab home." She said to the imaginary caller, her voice tinged with despair.

"I guess I'll have to stay close to the hotel. Call me when you are on your way." She said before dropping the phone back in her purse.

"Is everything all right?" Steve asked.

"My friend's car broke down and it's going to take a few hours before they can come pick me up. I don't have enough to take a cab home and the trains will be full of drunks and thieves."

"I can loan you some money for a cab if you'd like. You can mail it back to me." Steve offered.

Melissa smiled back at him as if grateful for the offer, but she smiled for a reason known only to her. His generosity proved that he was the mark she was looking for.

"I can't do that." She said, holding her hands up in refusal.

"Nonsense, I always keep some cash on me while traveling. You can't be sure when a place won't accept plastic." He said, pulling out his wallet and exposing at least a few hundred dollars in bills.

"I appreciate the offer but I never borrow what I can't pay back. I'm a college student and I don't have extra money to spend." She explained.

"Look, you can take your time paying it back. I would hate to see you stranded until your friends could get you." He said as he searched for the appropriate bills.

Melissa shook her hands and remained firm about not accepting the money. She explained that she had enough money to buy a few drinks at the bar, which would keep her from getting kicked out. She would try to stay in a corner and avoid any of the men that might hit on her.

"I tell you what. I have work to finish in my room. It will take me at least a few hours to complete. The room wasn't ready when I arrived, so they upgraded me to a suite. If you want, I can work in the bedroom and you can watch television in the other room. I'm not trying to hit on you. I just don't want to leave you in distress." He offered.

"I don't want to put you out." She said, intentionally sounding willing to accept the offer.

"I'll be fine. Trust me." Steve said.

Melissa acted as if she were thinking it over and then accepted the offer. After finding out his room number, she ordered two glasses of wine and a cheeseburger from the waitress, explaining to Steve that she had yet to eat dinner. She waved off his offer to pay and gave the waitress a few bills that she purposefully crumpled in her purse.

Upon arriving at the room, Steve left Melissa in the sitting room while he went to the bedroom to finish his work. She could hear the keys clicking on his keyboard, and almost felt sorry for him. She kicked off her heels and decided that she would at least show him the time of his life before getting what she was after.

The burger and drinks arrived within a few minutes, and Melissa ate while watching the television. She had learned early to make everything appear natural. A mark should always feel comfortable. She finished her meal and continued watching the television, making sure to allow enough time for Steve to feel that nothing was amiss.

After an hour of waiting, she retrieved a small baggy of white powder, and poured it into one of the glasses of wine. She swirled the glass until the powdered Ecstasy fully dissolved and after grabbing the other glass made her way to the bedroom.

"Hey, you didn't think both glasses of wine were for me did you? I got you one as well. It's the least I can do." She said as she stood in the door.

Steve was sitting comfortably on the bed with his computer balanced on his lap and sat the machine on a nearby chair as Melissa offered him the glass. Melissa sipped from her glass as she walked over to the window, acting uninterested about whether he drank the wine or not.

She could see his reflection in the window and kept calm with practiced ease as he sniffed the spiked drink. He took a sip of the wine as she made small talk about the view she could see from the window and smiled as he took another. He may have only been drinking the wine to be polite, but it didn't matter. What mattered was that he was taking a good dose of the drug, and would soon be up for anything.

"It's been such a long day." Melissa said as she lifted her hands above her head, feeling the hem of her dress pulling up and exposing the bottom of her pantyhose covered ass cheeks. It would take almost a half hour before the drug affected him, so until then she would give him a little show.

Melissa sat in a chair next to the window and continued her small talk. She talked about anything that entered her mind, knowing that Steve probably wasn't listening. She had caught his attention and was intent on keeping it. She started by stretching again, letting her breasts press together until they threatened to burst free from her dress.

Steve's cheeks turned a soft shade of red as Melissa pretended that she didn't notice the effect she was having on him. She instead became bolder, drawing her feet up to the chair as if she were a child. She parted her knees as she talked and felt a cool rush of air against her silk covered cunt. The French pantyhose did not have the usual white gusset and she had not worn panties. She knew that he could see her pink slit through the sheer material and the subtle widening of his eyes confirmed it.

Melissa judged that enough time had passed and decided to make her move. Without a word, she stood up and walked over to where Steve sat. She slid slowly onto the bed, crawling across it like a cat while he sat silently watching her.

"I don't think a glass of wine is enough of a thank you gift. I can think of something that you'll enjoy much more." She cooed as she reached Steve.

Melissa placed her hand against Steve's chest and gently pushed him on to his back. Thanks to the drug, he didn't resist as she climbed on top of him, straddling his waist and rubbing her crotch against his. She grinned as she felt the already hard column of flesh waiting to burst free from his trousers and slowly rubbed herself against his straining member.

"It seems like we're both thinking the same thing." Melissa cooed as she slid up and down his lap, her already wet pussy staining his trousers.

"I don't think this is such a good idea." Steve said as he lifted his hands to her shoulders as if to push her away.

Melissa leaned forward and his hands did nothing to stop her. She lowered her face to his and watched as his nostrils flared as he breathed in scent. She smiled and moved even closer until her mouth hovered above his, parting her lips with her tongue and slowly licking the plump red pillows. Melissa had not changed her plans, but all of her teasing had affected her as well and she planned on enjoying a good orgasm or two before the night was over.

Steve suddenly grabbed her shoulders and pulled her against him, his lips pressing firmly against hers and his tongue slipping gently into her mouth. The kiss wasn't forceful, but the shear passion of it almost overwhelmed her. He kissed her like he were dying of thirst and the wetness of her mouth would quench it. She melted into his arms as he devoured her, his hands sliding down her back to squeeze the firm cheeks of her ass.

Melissa had experienced many forceful lovers in the past but always managed to stay in control. Men were easy to handle as long as you offered them what they wanted most. As much as she was enjoying his attention, she knew she had to regain control. She finally broke free after a few halfhearted attempts, which was more because of her increasing sexual needs than his skill at keeping her in place.

"Let's get you more comfortable." Melissa said as she slid down his chest, her voice raspy and thick from excitement.

It only took a few seconds for Melissa to undo his belt and unzip his pants. His cock bulged underneath his white cotton briefs and she saw a widening wet spot forming where the tip pressed against the fabric. She struggled to pull the briefs down and gasped when she released his stiff prick. It sprung up as she removed the tight material and gently swayed mere inches from her face.

A familiar musky but clean smell filled her nose as she leaned forward, touching her tongue to the drop of clear liquid that seeped from the slit. She wrapped her hand around the shaft and squeezed it, forcing another droplet to ooze out to which she caught on her tongue. His cock twitched as she lapped up his cream, the tide of power swinging back in her favor.

Melissa slid her lips over the head of his cock, sucking the purple knob into her wet mouth and tasting more of his cream. She swirled her tongue around his swollen plum before taking him deeper until it rested at the bend of her throat. His wasn't too big, but it was the hardest cock she had ever felt. It felt like a steel bar covered in flesh and her pussy became wet just thinking about the firm column pounding deep into her cunt.

Melissa savored the feel of the firm cock filling her mouth and began to protest when Steve reared up unexpectedly and gently pushed her away. He pushed her on to her back before she could speak and pulled her to the edge of the bed. For a man of few words, he was definitely big on action.

Steve dropped down to his knees in front of her before spreading her legs and pushing them back. Her heart pounded in her chest as he lowered his head toward her pantyhose covered cunt and the muscles in her stomach clenched as he leaned forward and sniffed her excited slit. He continued doing so, and Melissa quivered inside as he soaked in her wet and musky scent.

Melissa jerked as he dropped his head and covered her slit with his mouth. He sucked the trapped flesh of her mound, noisily sucking her juices through the sheer fabric. She closed her eyes and concentrated on the heat and feeling of his mouth on her slit. Fresh cream flowed from her pussy as he excited her clit, his upper lip pressing against the swollen nub as he sucked.

Melissa couldn't believe that she was quickly approaching an orgasm. She gripped the sheets tightly as she thrust her hips upward against his suctioning mouth, gasping as he sucked even harder in response. His teeth grazed against her throbbing clit, causing her head to shake back and forth from the jolt that shot through her body.

"Oh yes. Yes!" She shouted as she climaxed, her body shaking and thrashing against the bed.

Melissa felt like her orgasm would never end as the spasms in her vagina continued. She gasped for air as the rest of the muscles in her body did the same, her stomach clenching so hard that she almost doubled over with every contraction. She collapsed when he finally pulled away and lie shaking and unable to move.

It was the most powerful orgasm Melissa had ever experienced, but it wasn't over yet. She was barely able to turn her head when she felt his lips brush her mound again. She looked down as he caught the wet fabric between his teeth, and with a quick jerk tore a hole in the fabric, exposing her red and swollen cunt.

The rush of cool air against her wet skin shocked Melissa, and within the few seconds that it took her to recover Steve kicked off his shoes and pushed off his pants and briefs. He unbuttoned his shirt and absently tossed it over his shoulder before climbing onto the bed where Melissa was still trying to recover.

Melissa arched her hips when she felt his smooth knob pressing between the slippery folds of her cunt. Her orgasm had been almost overwhelming, but she still hungered for the feel of a stiff cock inside her heated tunnel. Her lips formed an O but no sound came from her as he plunged into her with one savage thrust. She clawed at his back as he withdrew and drove into her again, his stiff member forcing her tight walls apart with each thrust.

Melissa found her voice and moaned loudly as the walls of her cunt grasped in futility at the invading column of flesh. She shivered as his swollen knob drilled into her wet tunnel while her delicate inner-lips curled around his shaft with every stroke. She soon adjusted to the pace and began pushing her hips upward to match his thrusts. Tears flowed from the corner of her eyes as his knob battered her cervix, but the minor pain was an added thrill that caused the walls of her cunt to squeeze his shaft like a vice.

A thin sheen of sweat covered Steve as he enjoyed Melissa's tight and willing sheathe and a low growl reverberated through his chest. She caught site of the clock and could not believe the time. He had been fucking her steadily for well over half an hour and wasn't showing any sign of slowing down. She knew that her pussy would be sore as never before.

Melissa felt the familiar tingle of an orgasm building between her legs and held onto Steven's shoulders as she closed her eyes and concentrated on how his shaft felt as it pumped deep into her creamy cunt. She whispered incoherently to him as he arched his back, changing the angle of his rapidly pumping cock. His shaft slid smoothly against her swollen clit and she shuddered as she quickly achieved another orgasm.

Her second orgasm was deep but not as jarring as the first, allowing Melissa to enjoy the warm waves the rolled through her. She felt her swollen vaginal canal fill with fresh orgasmic milk, her heightened sensitivity allowing her to feel every vein and curve of his swollen shaft.

Melissa was basking in her orgasm when she felt his cock swell deep inside her overheated pussy. Her eyes widened as he thrust inside her and held still, his cock erupting against her cervix. He moved only slightly as spurt after spurt of hot spunk flowed into her cunt, and she moaned at how warm his seed felt as it filled her, finally oozing out along his shaft. She closed her eyes as a feeling of warmth and fullness she had never before experienced washed over her.