Windy City Summer Fling

Justine stared out of the window of her tenth story condo overlooking the vast expanse of the city of Chicago. Summer had finally come to her beautiful city, and she smiled as she took a long swig of Diet Coke. Another week was about to begin, along with summer session where she would be teaching an introductory poetry class for the first time at one of the city's junior colleges. She was anxious to see what it would be like to teach adults, as her regular gig was teaching freshman and sophomore English for a Chicago Public high school. Although she loved her job and all its ups and downs, it would be refreshing to be among people who were paying for their education and truly wanted to be there as opposed to disgruntled teenagers who were there as a requirement by law.

She polished off her beverage and gave herself one last parting glance. Her dressy black Capri pants had been paired off nicely with a flowy white shirt that had a kitschy little sash that tied in the back, accentuating her ample bosom. She smoothed her auburn highlighted dark brown hair as she slipped gracefully into new open toed black sandals. Grabbing her school bag, she reached to pet her cat Thistle and bounded out the door.

She tried to ignore the anxious flutter of her heart as the El train squealed around its tracks and into the heart of the city. She took a deep breath and entered the building. Here I go, she thought.

"This is Mr. Flynn's office, Ms. Kendall," the quiet secretary said as Justine found the English department. "He should be out of class momentarily, so if you want to go in and wait, I'll let him know to expect you."

"Thank you, Diana," Justine replied. "It was really nice of you to show me around."

Justine sat down in a comfortable leather chair in Alexander Flynn's office. Mr. Flynn was an instructor at Chicago Community, as well as the English department head. He had interviewed her in early spring when she had noticed the position had opened. The office was cozy and reflective of the man who would be her boss for the next eight weeks. Besides an obvious love for literature and writing, various sports memorabilia adorned the walls, including pennants for the Bears, the Blackhawks, and the White Sox. She smiled as she saw a photo on his desk of what must be his children- a young girl and boy who looked to be about seven or eight at the time. It had been taken outside of US Cellular Field when the White Sox had won the World Series.

"Please, tell me you're a south side fan," a deep voice said to her. "I couldn't bear the thought of having a Cubs fan on board for the summer."

Justine laughed and turned, smiling as she stuck her hand out to shake his. "I was just admiring your photo there. Are those your children?"

"As a matter of fact, they are. Sam and Piper. They live in Rockford with their mom and I take them to Sox games as much as I can." He set a stack of papers down on his desk and leaned his hip against the desk. "So, you've never said. Cubs or Sox?"

"Well, for what it's worth, I was born and raised on Bears football, but if I had to choose, I'll say Sox." She nervously tucked a strand of hair behind her ear and bit her lower lip. She didn't remember Alex Flynn being so handsome in her interview. She had been too concerned about making a good impression to notice his dark hair with slightly graying temples, swarthy tanned skin, and dark eyes that smoldered. He had to have been in his late forties, and she certainly noticed his tall build and stocky stature in gray khakis and a black polo shirt.

"I can live with a Bears fan," he replied, revealing shining white teeth as he smiled. "In any case, welcome on board, Ms. Kendall. I'm always happy to have fresh minds join us for summer session. Who knows? You might like the college arena so well you might give Chicago Public another thought. How long have you been a teacher again? I know you said in your interview, but the timeframe escapes me."

"I just finished my seventh year of teaching. It's hard to believe," she uttered. "Here I am, thirty one years old, and I'm an old pro."

"Ahh, to be thirty one again," he sighed. "In any case, I thought I'd be nice and let you share my office for the necessary demands- you know, grading, data entry, office hours for students." Maybe even locking the doors, pulling the shades, and having his way with her on his desk, he thought wickedly, then pushed the thought away. In addition to her intelligence and drive for literature and poetry, he had been wildly attracted to her in their initial interview. He had thought of her often since early March, and on purpose he had decided to let her share his office space. He would be the epitome of professional, cordial and polite to her, even as he tried to stifle the vision of her underneath him on his desk. It was quite exciting.

"And if you don't mind my asking, how long have you been teaching?" She was curious to know his age.

"I'm forty nine years old, Justine. Next year I hit the big five-0h. I've been teaching English for twenty five years now. My, how time flies." He crossed his hands over his chest and smiled. He liked her hazel eyes and how they twinkled. It was endearing.

He's so fucking hot, Justine thought to herself. It was going to be a challenge to remain professional, especially since they would be sharing an enclosed space when there were breaks between their schedules. He mentioned his children's mom lived in Rockford? That obviously meant he was divorced, but was he otherwise involved? She made a quick glimpse to his left hand, which remained ringless. She was intrigued by him- his dark looks, his sexy demeanor. It was hard to deny there was a strong attraction between them.

"Well, go ahead and make yourself at home here in my- er- our office. Here's a key. I'd just ask that you keep it locked up when you're not in here." He dangled the key in front of her. As she went to grab it, he playfully tugged it away. She looked up at him through her eye lashes and he winked. He grabbed her hand and placed the key in her palm. "Good luck at your first day with the adults, Ms. Kendall."

When she was sure he was far away, she grabbed her cell phone out of her purse and made a call to her best friend Todd. She pictured his tall, lanky form curled up in bed at this early hour. He was a bartender in Boystown and shared a loft there with his partner Braxton. Two gorgeous men who treated her like a princess. The problem for her and every other red blooded female in Chicago? They were in love with each other. Life was sometimes just not fair!

"I was just having a dream I was sipping sangria with you and David Duchovny at Emilio's," Todd's smooth tenor uttered sleepily. "This better be good, Ms. Justine."

"I'm in lust with the department head," she sighed, sitting down at the desk that had been put up just for her. "Tall, handsome- we're talking some kind of southern European breed mixed with Irish. Forty nine. Probably divorced."

"Mmm," he uttered cautiously. "Sounds delightful, but do be careful, lovey. It's best not to mix business with pleasure. It's always nice to look, though."

"Ugh, Todd!" she sighed with frustration. "It's been four months. I haven't ventured for real penetration since Andy. A girl's gotta get some play beyond the vibrating objects, right?"

"I think dear Andy didn't measure up to the vibrating objects, eh?"

Justine rolled her eyes and laughed, knowing there was no love lost between her gay best friend and ex yuppie boyfriend.

"I need to go, sweetie, but I'll talk to you later," she said swiftly as she glanced at the time.

"Cocktails Friday with Brax and me. Bring Delilah and Simone," he said before telling her his usual parting "I love you" and kiss-kiss.

She turned off her cell phone and sighed, glancing at the clock. She had to swing by Diana's desk to pick up her copies of her class syllabus and the first day's homework assignment. Smiling as she thought of the secretary who so generously offered to make her copies, she made a mental note to bring her some coffee and doughnuts sometime. She liked to make people happy.

Her class was a well-received one as she glanced down the roster. Although twenty five was a rather hefty number, she liked the initial class discussion she'd brought forth on a very simple poem by Robert Frost. The age range was anywhere from nineteen to fifty. It would be interesting to hear various generations' ideas and see what their talents were in composing poems.

Later on, as she typed away on her personal laptop, she heard the door crack open. Mr. Flynn stepped in quietly and closed the door behind him. She felt her pulse begin to race a little as she tried to appear calm and collected.

"Well, inquiring minds would love to know, Ms. Kendall," he uttered as he sat down in the chair across from her desk. "How did your first class go with the big kids?"

"Please," she smiled. "Call me Justine. And it was a great class this morning. After the initial introductions and beginning of the session banter like attendance and policies, we had a great discussion on some Frost poems."

"Very well, Justine," he replied, a lazy grin spreading across his face. "I'd love to come observe sometime. That is of course unless it would make you nervous. I'd love to hear you lead a discussion- maybe even join in on one."

"You're welcome to join me anytime," she replied smoothly, then remembered professionalism as she began to imagine his hands on her body. She cleared her throat and sat up properly. "Well, I'm about to let you get back to enjoying the solitude of your office in just a few minutes here. After I send this email I'm done for the day."

"Oh, it's no problem, Justine," he said gently as he casually admired the curve of her neck. He longed to brush the hair away and taste her... Good Lord this was going to be a challenge...

After a few moments of heavy silence as he worked away on his own laptop, she packed up and stood, smoothing her shirt carefully and nervously. "I'll see you Wednesday."

"Wednesday it is," he replied as his phone rang. He watched her leave and felt himself go hard. He predicted it would have to happen before the summer session ended. Professionalism be damned, he would touch her, kiss her, taste her... He imagined his throbbing cock inside of her tight velvety softness. He could hardly wait. Despite the circumstances- all of them, he wouldn't rest till he'd had her.

"I'll see you Wednesday, Diana," Justine said as she stopped once more at the secretary's desk. "Thanks again for helping me out this morning- I really appreciate it!"

"No problem, Justine," she replied. "Um, Justine, look out!"

As Justine turned to walk down the hall to the elevator, she ran right into a man carrying a stack of papers in one hand and a bottle of pop in the other. He clumsily dropped the papers and spilled some of his pop on his red polo shirt.

"Oh no," Justine said sadly. "I'm so sorry, really I am. I had no clue-"

"It's ok, really," the man replied. She sensed his underlying aggravation, but he tried his hardest not to show it. "It's Monday. Of course everyone's computer went to hell over the weekend and yours truly gets to fix it. Being an IT guy sucks sometime, but who's complaining?"

"Not you," she said jokingly as she bent and helped him pick up the papers. When she stood and neatly placed her pile on Diana's desk, she pulled some tissues out of her bag so he could wipe the pop from his shirt. He gladly took them and began to blot the best he could. "You blot like a pro!"

"I'm perpetually spilling- I oughta be a pro!" Way to go, Rob. Way to embarrass yourself yet again in front of a hot chick. No wonder you're single!

"I'm Justine Kendall, by the way," she said softly as she held out her hand. She couldn't help but giggle when he reached out his hand with tissue in it. He laughed awkwardly, stuck the tissue into his pants pocket, and shook her hand properly.

"Rob Gleason," he said shyly. "Resident IT guy. If you ever have trouble with your computer, just give me a call."

She smiled up at him. What a sweet guy! He was tall with tousled brown hair and blue eyes that shyly met her own. Unlike Alex Flynn, he was totally unaware of the fact that he was cute. With a few days' worth of stubble, there was something endearing about his rugged features.

"I'm teaching a poetry class for summer," she explained. He shuffled his feet awkwardly as Diana stifled a little giggle. "Um, I guess I'll be on my way. Nice meeting you, Rob. Hope to see you around sometime."

Rob watched her go and blushed profusely as Diana eyed him knowingly. "So I guess I'll be seeing you a lot more often in the English department now, huh? Just a little FYI, she'll be here every Monday, Wednesday, and Friday mornings."

"Sheesh," he stammered, shifting his weight from his left to right foot. "I dunno what you're talking about." He smiled and walked away, this time with a little lilt in his gait. It would appear as though a pretty girl had noticed him. Who knew what potential that could have, he wondered.

Friday had arrived and her first of eight weeks were now complete. Tension was thick in Alex Flynn's office. As she packed up her things to head out for the day, Alex leaned back in his chair and eyed her inconspicuously. He truly appreciated the casual purple knit dress she wore that day. It reached the very top of her knees and had one of those snug fitting tops that hugged her delicious tits decadently. She wore those black sandals again, and he loved her red painted toe nails. No doubt she had been spending more time in the sun as her skin glowed to near perfection.

"So, um, you got big plans for the weekend?" she asked as she delayed having to leave. He didn't seem to be too enthralled in his work at the moment. In fact, it would seem he was checking her out. She had kept her back to him as she packed up, but she felt the heat of his stare. When she turned around, he was facing her.

"I've got Sox tickets for Saturday, and Sunday is pretty much my lazy day. Gonna catch up on some reading," he said gently. "Say, if you're not busy, could I interest you in some lunch? I was thinking about hitting Navy Pier- there's several places there to eat, ya know. I know you have your laptop, so you could just leave your things here if you'd like."

"I'd love to join you," she said calmly, but inside her heart was thumping. She grabbed her purse and followed him out the door. To her surprise, Rob stood talking to Diana. She smiled and walked casually up to him, as Alex followed behind. "Hey Rob! Good to see you again! I'm not going to bump into you this time, I swear it!"

"Oh, I see you've met IT guy extraordinaire!" Alex chimed in as he joined the group. He slowly put his hand on Justine's shoulder in a way that made Rob's heart fall a little. He tried to ignore it.

"How's it goin, man?" Rob said quietly. "Good seeing you again, Justine. I guess I've got some work to do back in my office. I was just checking on some hot spots up here." Justine watched him walk off and he seemed almost deflated. She wanted to talk to him, but Alex urged her onward.

"Diana, we're headed off to grab some lunch. If you could just send out those flyers to the department I'd really appreciate it. I'll see you around."

He hailed a taxi and opened the door for her as a proper gentleman should. Expertly he directed the cabbie where they were headed, and he casually caressed Justine's knee before he placed his hand on the sticky leather of the back seat.

"So you never said what your weekend plans would entail," he asked as he edged closer to her. She smelled his cologne and felt intoxicated. Her hormones were her enemy as of late. She wanted this man so badly she could taste it, but knew it would be wrong to act on them. It had been a long time since she had felt this whirling sensation to copulate. She bit her lip as she admired his dark brown eyes.

"Cocktails tonight with some friends on Halsted," she said gently. "Tomorrow I'll do some lesson plans, and Sunday is kind of up in the air."

"Boystown, eh?" He laughed gently. "I guess going to the gay bars is the place to find hot chicks. I had a friend once who pretended to be gay. He ended up hooking up whenever he did it. I guess I shouldn't be telling you the tricks."

"Oh, I'm sure I've run into that kind before," she replied. "I guess a man's gotta do, huh?" She laughed nervously and then felt like a silly teenager.

"And here we are," he announced. He handed the guy a twenty and guided her to the entrance. The Pier was packed as normal. He put on his sunglasses and looked gorgeous in form fitting jeans and a light blue button down shirt that he'd left untucked. Looking like he'd just stepped out of a magazine, Justine saw various women checking him out- some not so shyly. She wondered if he saw and guessed that he did. "I need a Mai Tai. Come on, Justine. Follow me and I'll buy you a drink."

A gentle breeze caressed them as they headed into the hubbub of the jaunty tourist site. She breathed in the scent of Lake Michigan and roasted almonds as the neared a stand selling the delicious treats. When Alex handed her the cool juicy alcohol-ladened drink, it refreshed her mouth as its coldness stung her.

"Here's to your first week," he said, his voice covered in sexy. She clinked plastic cups with him and smiled. They bantered back and forth about various writers, discussed politics briefly, and pondered if the Bears would do anything good with their upcoming season as they sauntered to the edge of the pier. The lake was peaceful as Justine realized she'd just consumed the entire drink on an empty stomach.

"I'm a little tipsy," she said softly as Alex turned to her and laughed. He looked down at her and tugged a lock of hair.

"Can I be completely, totally, and utterly honest with you about something, Justine?" He said after a brief silence. He pursed his lips and subtly pulled her closer to him so that she had no other choice than to put her hands on his chest. He knew this wasn't smart, but he followed his heart every step of the way.

"Always," she replied as her heart pounded.

His heart fluttered a little and he almost hesitated in telling her the truth. He looked down into her sweet angelic face and exotic hazel eyes. It was enough that he held her closely to him. It was even more than he wanted her with an urgency that was damn near painful.

He leaned in carefully, moving her hair aside so that his lips graced her earlobes. She bit her lip and closed her eyes as he whispered. "I want to take you back to my condo, lift your dress up, slide your panties down and lick every last drop of your sweet pussy. How does that sound to you?"

"I think," she said suggestively, definitely the alcohol giving her its sure-fired confidence, "that I would savor every second of your tongue, and I can only hope you'll follow with your cock... right after I've licked and sucked it till you're panting my name."

"Jesus Christ, I want you," he said as he gently kissed her lips. "I've wanted you since I first saw you, Justine. I'd like to fuck you right here and now on the edge of Lake Michigan, but I suppose that would be socially unacceptable. We can go back now, or do you need to get into the office to get your things? We can always go back later. I don't plan on letting you get out from underneath me anytime too soon. One of the security guys will let us in."

"If you don't fuck me soon, I'm going to burst," she panted. "We'll worry about my laptop after I can think clearly. All I want to do touch you and taste you."

"I'll second that," he said as he brushed her hair back as he imagined doing earlier. He nibbled her neck and she gasped.

"Taxi cab now. Please feel free to use your fingers. You don't live far, do you?"