Cowboy in Chicago

"Sam, another Budweiser please," James asked as he drained the last one.

"He's open. He's open ... Touchdown!" James slapped his hands on the solid mahogany bar before him. "Sam, did you see that pass? I didn't think he'd get it between the two d-backs."

Sam sat the bottle on a fresh napkin in front of James. The University of Texas was playing on ESPN against LSU and James was wishing he were in Baton Rouge instead of sitting in this fancy bar in Chicago. He never missed a home game and tried to make many of the road trips. He had planned to follow the team to LSU but his boss had to cancel on this trip and sent him in his place.

This was the second time James had had to go to Chicago and he didn't care much for it the first time around. He had walked around and seen some of the sights but it was just too big city for him. He figured he'd have dinner, watch the game from the bar and call it an early evening. The hotel was five star rated and though he looked out of place wearing Levi's and boots, he didn't have any problems with being out of place.

James had walked around the corner and found himself an excellent steak before returning to the hotel lounge and making fast friends with Sam the bartender. He took up a barstool at the end of the bar near the TV to watch the game. Hotel guests and passers-by stopped into the bar, usually waiting for dinner reservations or just to meet friends. James had been pretty oblivious to most of the crowd. He was able to see them enter the lounge by glancing in the mirror behind the bar, but he wasn't really interested. He was watching Longhorn football.

The game was early in the third quarter and Texas looked like they would prevail. A couple groups of people had gathered at different tables in the lounge. Two professionally attired cocktail waitresses serviced the tables as Sam poured the drinks behind the bar. During a commercial break, laughter erupted from a table near the opposite end of the bar. James looked over at the commotion and saw three guys sitting with four beautiful women. There were two blondes, a brunette and a redhead. The men were all wearing dark suits, each finely tailored. The women wore dresses of varying lengths but each quite dressy yet sexy at the same time. Before James looked back at the game, the young lady with long auburn hair caught his attention. She briefly smiled at him, her green eyes flashing. James returned the smile before turning back to the game. As Texas drove for another score, his attention was now somewhat diverted. He found himself looking in the mirror, seeing the auburn-haired beauties reflection. Her back was to the bar, but he could see her profile as she chatted with her friends.

The third quarter was nearing the end with Texas up by two touchdowns. "Evening Sam. A glass of my Cab and another Bud for your friend."

James turned his head away from the screen to find the stunning redhead standing beside him. "You don't have a problem with a lady buying you a drink, do you cowboy?"

"No ma'am." James slid off his barstool, "Have a seat?" as he offered her the barstool beside him. When she was seated, James sat back on his stool.

"My name's James ma'am."

"It's a pleasure to meet you James. My name's Stephanie but my friends call me Stevie." Sam sat the two drinks down on the bar before them and walked to the other end. "You seem to have some interest in this football game. Who's playing?"

"LSU and Texas, my alma mater. Texas is up 14 at the end three."

"Texas is playing better than expected this year. Do you think they can win their conference?" James was impressed. She didn't sound like a Texan yet she knew about Texas football.

"Yes ma'am I do. Are you a football fan?"

"I watch it some and I like to stay informed." The two of them talked through the first part of the fourth quarter, James' interest in the rout was waning as he studied this beautiful lady. Midway through the quarter, one of the blondes from her table slid up beside and whispered in Stevie's ear. "My friends are getting ready to go to clubbing. You're a little underdressed but we can get you in with us. Would you like to join us?"

James thought about it for moment, "Sounds nice but my music tends to stay pretty close to country. Y'all don't look like you're headed to a country club." James cracked a big smile as he studied her skin-tight dress and heels.

"Not quite country. That's too bad, I think we'd have some fun." She slid off the stool and James did like-wise.

He extended his hand, "Pleasure to meet you Stevie and thanks for the beer." Stevie took his hand then leaned in against him and kissed him on the cheek. She leaned close enough so he could feel her breasts press against his chest. She walked over and joined her friends as they got ready to leave.

"You're not going with her?" Sam asked as he walked over to James.

"Nah. I like to dance but only to country."

"Damn, Stevie doesn't get turned down very often."

"You know her?"

"Yeah, I've known Stevie a couple years. You get to know people when you tend bar."

"Do you know her friends?"

"I know three of the girls."

"Not the guys?" Sam had a slightly confused look on his face for a moment. The girls waved at Sam as they left the lounge. He realized James didn't have a clue.

"The girls are something like regulars in here." James just looked at him. "Damn, how small is that town you live in cowboy?"

"It's no Chicago, but it's a pretty good size town. Why?"

Sam bent over the bar so he could lower his voice. "Stevie and her friends date for a living." James' eyes lit up as recognition set in. Sam could see it coming, "Don't say it!" He could hear the word 'hooker' being blurted across the bar. Some of the staff new about the girls but they kept it pretty quiet so upper management wouldn't know. As long as they didn't embarrass any of the guests, they were welcome. Who doesn't like to see beautiful women?

James leaned forward, "She's a prostitute."

"Escort is the correct terminology."

"She was so pretty and so easy to talk to. I never had a clue."

"Stevie's a great girl. She comes in here some nights when it's slow for both of us and she keeps me company. She's really a bright girl."

At that moment Sam saw the lounge door swing open and Stevie walk through the doorway. He smiled at her striding towards the bar. Her long auburn hair sat on her shoulders, her body amply filling out the curves of her above the knee dark green dress. James picked up on Sam's smile and looked in the mirror. He saw Stevie walking up to him.

"Hey cowboy, I know a great little C&W bar a ten dollar cab ride from here. Interested?" James spun around on his stool to face her. She caught the look in his eyes and knew that Sam had clued him in.

"Sorry Stevie, I didn't think you'd be back ..." Sam's voice trailed off as Stevie held up her hand.

"No problem for me. The question is does James here have a problem?"

James thought about it for only a moment, "The only problem I have is wondering how you can dance in heels that high?"

"Well I think we should get that cab and I'll show you."

"I'll call Michael and have him hail you a cab," Sam called after them.

James slipped his hat on his head and took Stevie's hand, leading her through the lobby. "I've got a couple questions for you."

"Only a couple? Well the answer to the first one is that I picked you up tonight. What's the second one?"

James smiled at her the way only a Texan can smile, "I suppose the second one can wait."

Stevie told the cabbie where to take them. In less than ten minutes they were outside a big club offering country music. You could hear the fiddle through the open door. "Will this work for you?"

"Do you know how to dance?" Stevie pulled him to the dance floor before they even had found a table. The tempo was quick, but Stevie stayed in step as James pulled her close and led her around the crowded dance floor. After a few dances, the place was rapidly filling and they thought they should find a table while one was still available.

A cute waitress with skin-tight Levi's approached them, "What can I get ya?"

James looked at Stevie, "Two Bud's will be great." James was a bit surprised after the hotel lounge. "This isn't a red wine kind of place."

"So what happened to your friends?"

"I found someone a little more interesting this evening." James actually blushed but the brim of his hat hid it. "Are you a real cowboy or do you just wear the hat?"

"I actually have some horses at home. I don't do it for a living, but I do enjoy riding 'em when I have the time." The cold beer arrived in longneck bottles. Stevie tilted her head and took a long drink in the sexy way that women can.

The lead singer of the band let out a whoop and broke out a fiddle. As he plinked the strings, Stevie pulled James to his feet and onto the dance floor. Her skintight dress was definitely out of place in the bar but you didn't hear any cowboys complaining. As the tempo picked up, the two of them moved a little quicker on the floor. James could feel his temperature rising as he danced with Stevie. After four quick tempo songs in a row, they slowed the music way down. James pulled Stevie close and she slipped his cowboy hat off his head and onto to her auburn locks. They were very close and moving gentle with the rhythm of the music. James moved his lips close to Stevie and she did likewise. She opened her lips to receive his probing tongue. James pulled her just a little closer. The kiss was warm and soft. James realized the music had stopped and he broke off the kiss. Stevie looked at him a little surprised. "The music stopped," he explained. Stevie smiled and thought to herself that he really is a cowboy.

After a couple hours of dancing and a couple rounds of beer, Stevie asked what James had wanted to ask her. "So cowboy, would you like to go someplace a little quieter?"

James didn't need any further encouragement to answer. "Yes ma'am. I've been thinking about it, but I didn't want to be too forward."

"Pay the waitress, I'll get us a cab." James caught up with Stevie on the curb. She was leaning into the cab talking to the driver. "Thanks Mikey" was all James heard as he approached the cab. They climbed into the backseat and the cab pulled away from the curb. "James, this is my old friend Mikey."

"Pleasure to meet you." James looked around and thought they were heading in the wrong direction from his hotel, but figured he must have lost his direction with all the tall buildings. Stevie turned his head with her hand and gave him a kiss. A short drive later, the cab pulled up to a tall building overlooking the lake. "Here you go Stevie."

James was a little bewildered. He looked at the front of the building and a well-dressed doorman was approaching the cab door. He pulled on the handle, "Good evening Miss Johnson."

"Hi George. How are you tonight?"

"Very well, thank you. It's a beautiful evening." By now, James and Stevie were standing on the sidewalk. Stevie pulled out a twenty and handed it to Mikey.

"Thanks for the ride. Be careful." Mikey waved out the window as he pulled away from the curb. Stevie led James across the quiet lobby to the elevator. She punched the button marked "PH" and inserted a key.

"I thought we were going to my hotel."

"What kind of girl do you think I am?" Her eyes crinkled into a smile as she asked. Neither had mentioned her profession throughout the evening.

"I - I - Um ... I didn't mean anything..." By now Stevie was smiling and laughing at his embarrassment. This time she could see him blushing.

"When I'm with someone I like, I want to be comfortable. Trust me, no matter how nice the hotel, hotels are not comfortable." The elevator stopped and the doors opened up on the thirty-fifth floor, the penthouse. There were four doors off the elevator. Apparently each door opened to a corner suite. Before Stevie put her key in the door, she turned to James, "this is a date. I met you in the bar and I've enjoyed the evening to this point. Do you want to ask that second question now or would you like to come inside?"

James looked all serious "I do have one question."

Stevie wasn't sure what to expect but she was ready for most anything. "Yes?"

"Do you have a toilet I could use?" Stevie cracked up at his question.

She turned the key and pulled him inside, "Get in here cowboy!" Stevie flipped on a light and pointed down the hall. "First door on the left." James was but a minute.

James opened the door to a near dark hallway. Music was coming from further down the hall. He walked into Stevie's bedroom. It was dimly lit but he could see her silhouette behind a standing curtain. She was apparently changing for the evening. He stared at her near naked body through the opaque curtain, it was lightly lit from the other side and projecting her image onto the curtain. It was all for effect. Stevie walked around the curtain wearing a dark green silk robe and tall heels. She walked up to James and circled her arms around his neck. He pulled her tightly to his body as they embraced.

With her heels, they were nearly the same height. As the kiss grew more passionate, Stevie began to press her body firmly against his. She reached up and grabbed his hat. She playfully put it on her own head, tilting the brim back. James moved his hands down her body, grabbing her cheeks. She was very toned. He could feel the straps of her garter, but no panties as he stroked her ass. He reached up under the edge of her silk robe and felt her soft skin for the first time. His fingers traced the straps on the back of her thighs from the stockings up to the waistband. When he reached the waistband, he moved his hands towards his body until he found the forward set of garter straps.

He slipped his thumbs inside the straps as he moved down her legs. James stopped about six inches down. He moved his fingers inward and stroked her inner thighs. He felt just a swatch of silk, he knew it would be a dark green thong between her thighs. He broke the kiss. "Excuse me ma'am, but you seem to be a bit overdressed for the occasion."

Stevie smiled at him, "Why cowboy I was just thinking the same thing about you. Can I help you out just a bit?" Before he could answer, Stevie had pushed James backward onto the bed. She reached down and lifted his left leg. She grabbed his boot at heel and toe and slipped it off his foot. She did the same with his right then removed his socks. She leaned forward and fingered his belt buckle. As she leaned, her robe opened to show James the pleasures that awaited him. He was leaning on his elbows as she undressed him.

"This is a big belt buckle you have" she commented in her best 'little red riding hood' voice. She traced her fingers down his fly as his aroused cock swelled under her touch. She didn't grab him or stroke him, she just innocently traced her fingers over his crotch. James' imagination did all the work. "U-m-m-m, it seems like my Cowboy has something he wants to show me." She looked up at his face. In some ways, it was a look she had seen many times before, the look of a man who was being played by a master. But there was something different about his look. James exuded a confidence that she hadn't often seen. It was a look that raised her excitement level. She knew this wasn't just a fuck to him and she wanted to fuck him as much as he did her.

Stevie unfastened his belt buckle and began to slowly unfasten the five buttons on the fly of his jeans. As each button fell free, Stevie bent her neck and lightly kissed the shiny silver button. By the third button, she could feel his erection pushing firmly on the other side of his fly. When she had unbuttoned each, Stevie stood up between his legs at the end of the bed. She unfastened the tie on her robe and allowed it to fall open. James could see twelve inches of skin from her belly to her neck. The robe clung to her breasts, exposing them yet hiding them. Stevie put her hands on her inner thighs and slowly slid them up her body. She paused for a moment as she passed between her thighs before continuing up her body. A small silver ring hung from her navel and her fingers lightly tugged at it. Her stomach was tight and tan as her fingers traced small circles. Stevie turned her hands upward as her fingers moved towards her breasts. "Would you like to see more?" she asked devilishly.

James just nodded his head, his eyes transfixed on her hands. Stevie massaged her breasts under the silk of the robe for a couple moments, building the excitement. Then her hands quickly nudged the silk and the robe fell free of shoulders and slid down her back. Her hands moved around her breasts, exposing her nipples to James for the first time. Her breasts were tan like the rest of her body and dark aureolas were centered perfectly. In the middle of the dark circles sat two round nipples like cherries on a sundae. Her thumbs stroked across her nipples as her hands slowly moved around her breasts. Her left hand continued to play with her breasts as her right hand moved back down her stomach. Upon reaching the top of her thong, she slid her three middle fingers under the waistband. Her fingers quickly disappeared behind the cloth. James could see the outline of her fingers as she moved them up and down the length of her pussy.

Stevie could see James' erection pushing firmly against his opened fly. "I think its time for you to get a little attention." She slipped her fingers from the thong and stood before him. Stevie leaned forward and put her hands on the top of his Levi's. As she started to pull his pants down, James lifted his hips so she could slide them off easily. She slowly pulled them down and stopped as his erect cock danced freely. Her eyes studied it for a moment, she knew it would fit quite snugly inside of her. She then pulled his jeans the rest of the way to the floor. James lay on the bed wearing only his shirt.

His cock was extended to full nine inches as he lay before her. His balls were covered in light brown pubic hair, concealing their size a bit. Stevie dropped to her knees at the end of the bed, James legs on either side of her. Her nails raked across in his inner thighs, always stopping short of his groin. James' cock danced with excitement, twitching up and down against his body as Stevie toyed with his mind and body. Stevie really enjoyed sucking a well-hung cock. Stevie enjoyed all other forms of sexual activity, and she had tried many forms, but sucking a man's cock is what always got her really hot and bothered, even when she was doing it for money. Tonight it was only for pleasure. Fortunately, James was providing her with an outstanding cock to do her magic. She had felt him up while they were dancing and she expected she would like what she'd find inside his fly.

As his cock stood fully erect just inches from her face, she was quite pleased with the results. She brought her soft lips to the tip of his cock. Her tongue lightly licked across the crown, just a drop of precum had formed. She slowly wound her tongue around the head, feeling his smoothness as she passed over his skin. James could feel her warm breath on his sensitive shaft, only heightening his sensations. It took her a full three minutes to finally move past the crown and down to the underside of his shaft. For now, she was only using her tongue to exhilarate him. She slowly licked her way down the entire length of his shaft, stopping only when she reached his balls. She worked her way back up his cock until arriving once more at the head. She could feel James holding his breath as her tongue found the most sensitive spots imaginable. Finally her lips formed an "O" and she surrounded his cock.