Windy City Summer Fling

"West Loop- twenty minutes tops."

They could barely keep their hands off each other during the seemingly long ride back to his place. They kissed with abandon as the taxi driver spoke in a foreign tongue on his Bluetooth. Alex whispered hot, dirty promises in her ear as she ran a hand over the bulge in his pants.

"I have to take a different route," the cabbie said in his thick accent. "There seems to be an accident on State."

"Whatever works, my friend," Alex uttered to the guy, and then he whispered in Justine's ear. "Let me have just a little taste of your pussy, Justine." He slid his hand up her thigh and rubbed his finger up and down the soaked satin of her lavender panties. Ever so slightly he slid his finger to the treasure within and thought his hand would catch on fire. He wiggled against her clit, teasing her, then painfully slow with his finger, dragged it down her thigh and to his mouth. He licked it, his eyes closing.

"Just like I thought," he whispered. "Tangy, like a tropical fruit. I can't wait to feast."

After what seemed like eons, they reached the front of his building where he paid their driver and guided her up to the fifth floor.

"I suppose you want to grand tour of my condo, right?" He joked, his arms around her waist.

"I'd be more than happy if you'd start the tour in your bedroom, and we'll just stay there for the whole thing."

He dropped his keys on the table and swept her up into his arms. She had no other choice than to wrap her hands around his neck. When they reached their destination, he placed her gently on his bed, closed the door, and pulled the shades.

"Justine, you've intoxicated me with your beauty," he whispered as he admired her lying on her back in front of him. "Raise your dress up for me, and I want you to slowly pull your panties down. Spread your beautiful pussy lips for me."

He sensuously undid his belt and undid his jeans as she complied to his wishes. She raised her hips ever so gently as she pulled her panties down. She ran her hand down to the pliant folds of her nether lips. While she did so, he stripped and his amazing cock sprung forward with gusto.

"Now," he uttered as he ever so gently lay next to her. "Take your dress off, and take your panties off the rest of the way. That's my angel, oh yes... perfect." He leaned in and kissed her gently as her little dress fell to the floor. She lay half naked in just her matching lavender silk bra. He expertly caressed her nipples, enjoying the softness of her garment. His hand danced down her tummy, swirled around her belly button, and at last he found her pussy- hot, warm, and ready.

"MMM, Alex," she sighed as he ran just the tip of his finger up and down her saturated slit. She ran her fingers through his salt and peppery hair as he kissed her cleavage. Somehow he managed to raise her up and free her of her bra. The man was an expert. His mouth found her tits and licked them generously as he continued to play with her pussy.

Curious, she reached her hand down to feel his throbbing hard cock. He groaned and moved her hand away. Reluctantly he looked up at her from kissing down her torso. "You'll get your chance, Angel. For now, I'm hungry. You've got exactly what I have a craving for."

"Oh yeah?" she whispered as his finger dipped in deep. "And what would that be?"

"Mmm," he said as he licked her quickly at first, then more gently. "A hot, tangy, but oh so sweet, little pussy. You want me to lick your twat, angel? Tell me what you want me to do."

"Mmm, Alex," she whimpered, completely breathless. "I want you to finger me deep while you completely torture my clit. I want you to make me cum over and over and over again... mmmm! Yes baby, just like that!"

He savored her taste, savored her scent, and felt his cock go absolutely solid. He wanted to bury himself deep into the delicious pussy of this considerably younger woman, but he would feast on her till she was practically begging for him. After her third orgasm, he came up for air and was ready to mount her, but she pulled him up to her instead. She licked her musk from his sensual lips before pushing him over onto his back. She straddled him expertly, but didn't impale his member quite yet. She fingered her breasts and eyed him while doing so. She ran her hands down her torso and languidly placed them on his chest. She bent, kissing down inch by inch till finally she found herself up close and personal with his cock. She couldn't believe she had wound up in his bed like this, but she focused on the bliss of her reality and snaked her tongue out to greet it. He moaned as she treated it like her favorite candy. She loved giving head. She loved the warm hot, velvety feel of a man's cock, and she loved bringing him to the very brink of desire. It was a power surge that she felt now as Alex gripped her head in his hands.

"I gotta put it in your pussy, baby," he uttered painfully. "If you reach in that drawer over there, you'll find some condoms. The quicker the better." He'd given the possibility of this happening quite some thought. On his way from work last night, he'd stopped into the drug store for protection. He was so grateful to have thought ahead!

She leaned over carefully, undid the wrapper, and smartly rolled it down onto his large member. He rolled her underneath him and entered her gently. It was a tight fit, but he closed his eyes and let out a sigh of relief.

"You don't know how badly I've been wanting to do this," he whispered. Her pussy was so hot and inviting. He closed his eyes and relished the feel. Even inside the thinly-made condom, he had never felt such bliss.

"Mmmm, Monday morning at 9 am was about the time for me," she replied as she slowly lifted her hips to meet his thrusts.

"I had no idea the attraction was instant," he replied as he kissed her forehead and cheeks. "I know it was for me." He wrapped his hands around her and they moved together as one entity. He simply looked down at her and was mesmerized by her beauty. He felt her pussy muscles contract around his very happy cock and he shivered.

"You like that?" she asked wickedly. "Well, get ready sweetheart. I'm going to fuck you like this all afternoon."

"Mmm, is that a promise?" He gasped again as she pushed him off of her and she expertly straddled him. She slid down his cock painfully slow, squeezing him as she did so. He was worried he would cum right then and there. "I have a feeling my new addiction is going to be Justine Kendall."

She rocked on his cock, squeezing him as she did so. She felt the mossy patch of hair on his chest, and tossed her head back in pure bliss. She barely felt his fingers dig into her hips as he thrust upwards into her velvety paradise.

"Your cock feels amazing," she cried as she continued her glorious movements. "I have been imagining it. Making love to you like this- it's even better than I dreamed."

He let out a groan and reached up for her ample breasts, fondling them, rolling her erect nipples round and round between his fingers. He had rarely made love like this in the past. The torrential storm in his groin longed to burst, but he held back, closing his eyes to prevent an early ending. He savored the moment- the feel of her, the sight of her, the scent of their moisture blended with sweat, cologne, and her gentle citrus perfume. It was a scene he wouldn't soon forget.

"Hold me, oh Jesus, Alex, I'm going to cum," she whimpered, and he complied, wrapping his hands around her waist. "Harder, sweetheart, and don't stop. Don't ever stop fucking me."

"I've got you, angel," he soothed as he felt her explode on top of him. The sight was perfection. She flung her head back in pure bliss, her mouth slightly parted, her eyes fluttering like the wings of a hummingbird. It unmanned him, and as much as he'd wanted to stay hard for her, he gripped her hips and fell from the ledge right along with her.

"Ohhhh yes," he cried. "Justine, my sweet angel, YES!" He shattered into a thousand pieces beneath her and he felt her cry out again in pure ecstasy as he floated among the stars. They panted, and she kissed him wildly all over his face. She moved from his body and rested her head on his chest. He let the endorphins carry him as he closed his eyes and concentrated on the beating of his heart.

"Fucking amazing," she panted. "For an English teacher, I'm simply lost for words."

He laughed gently, then pulled her close to him as she reached in for his exhausted cock. "Oh baby, you're gonna have to give him some time to regenerate. You wore him out."

"He'll be ready in an hour or two," she sighed as she stretched. "Long about the time I'm ready for Round two. But first, I could really use a nap. Mind if I open the window a bit?"

He watched her young body slide out of bed and discreetly reach around the curtain to open the window. As he figured, a gentle breeze blew in- just enough to cool their bodies off.

"You surprised an old guy like me can still fuck like a champ?" He asked curiously, though part of him was truly concerned. He'd never ventured out of his comfort zone- no matter how many times he'd wanted to in the past, he'd not acted on his desires.

"No surprise whatsoever," she mumbled as she latched onto him tighter. "Mm, you're very comfy, Alex. It's naptime."

He held her closely as she drifted off into slumber. Getting involved may've been a risky choice, but damn, was it worth it. He had zero regrets, and he couldn't wait to have her again and again. The day was young, and he was certain he could convince her to meet him again Sunday night after he'd fulfilled certain obligations. He hoped things wouldn't get too complicated, but he'd worry about it later. Tomorrow perhaps, or even Sunday when reality would take him by the lapels and shake him nice and good, but his heart and his cock reminded him that Sunday was the night he'd want her with him again... Ugh, good God.... He tried to push it from his head and heart, so to really focus on his here and now, he gently caressed her thighs, so soft and sweet. She moaned softly as he found her pussy still wet and stimulated from before. He pinched her clit till she exhaled her release. She awoke long enough to kiss him gently.

"You love to make me cum, don't you," she uttered hazily. "I'll return the favor. I promise. Just give me forty minutes or so."

An hour later, she awoke him with her lips all over his body, and this time it was a repeat performance of it again with Alex dominating her this time.

She finally felt refreshed and renewed. Her body had reacted nothing short of spectacularly to his, and she felt the awkward time coming as he rose to prepare a shower together.

"So, we might as well get the weird stuff outta the way," she said carefully as she sat naked on the edge of the bed. "Look, I'm a no nonsense kinda gal. I guess it's the teacher in me. We just had outrageous sex. There's also the matter that we work together and share an office. Was this just a one time "hit and quit it" type of deal, or are we going to enjoy ourselves again sometime?"

His heart skipped a beat and he spoke without even thinking twice. He had brought on this situation himself. He'd worry about the consequences later. For now, he wanted something perfect in his life. He needed an escape. He wanted Justine. "I want to continue this. But it has to be casual. And discreet, Justine. I've never crossed the line with an employee before." He edged over to her and sat down, rubbing her thighs and slowly reawakening her desire once again. She leaned back on her arms as he stuck a finger into her now drenched pussy. He licked up her honey and moaned. "I can't get enough of this, and I don't plan on letting it go. C'mon, my sexy angel. Let's go shower so I can dirty you up again later."

The shower lasted at least an hour because she found it very entertaining to sink to her knees and suck him off while he braced himself against the warm flow of the water. She lapped up his cum only to have him finger her pussy not once but twice to complete, pleasurable oblivion. She had never been so hungry to please and be filled by him.

Once they were out of the shower, she was amazed by his gorgeous form. He was tall and muscular, the hair on his chest just the right amount. He was dark complected, which she later found out was due in part to his Romanian heritage. His body hair was black, which he neatly trimmed around his well-endowed package that she already couldn't wait to have more of. She came over to him and caressed his ass cheeks, which he fully enjoyed.

"Didn't you tell me you had plans this evening up in Boystown?" He glanced at the time and knew he needed to get her out and get going.

"I'm sure they'll understand," she purred. "Especially where amazing sex is concerned."

"But if they're expecting you, you really shouldn't stand them up," he replied, urging her to do the right thing. He would've been more than content having her around, but it just couldn't happen. Not tonight.

"True that," she said as she smoothed her dress and slipped into her sandals. "I suppose we need to get to the office so I can pick up my laptop."

The cab ride was a little tense, as she could tell that something was weighing heavily on his mind. She totally understood his need to put the barrier up. This wasn't a relationship, and the truth of the matter existed that they really didn't know each other all that well. She'd had casual flings before, and she'd experienced the awkward mornings after. She had to work with this man, so she played the role she needed to do. There was no harm in their situation as long as she didn't get too emotionally involved.

It was after six pm, so he had to alert the security guard Dino to escort them inside to the elevator.

"We just need to run up to the office real quick. Ms. Kendall needs to pick up a few items she left behind from this afternoon."

"No worries, Mr. Flynn," he replied as the trio walked to the elevator. "You know I'm always here to help you out when needed."

Alex grinned and stepped in the elevator after Justine. They rode up in silence, and Justine pretended not to be concerned. They stepped into the office and Alex laid his things on the desk, including his cell phone. Justine grabbed her leather bag and sat while Alex punched out a few things on his lap top.

"Damn," he uttered. "I need to get into Harry Schalm's office real quick. Look, sweetheart, sit tight for a few minutes, ok? I'll be right back." He kissed her forehead gently and disappeared. Ten seconds later, his text message alert went off. She thought about calling after him, but decided not to.

She'd always been an honorable, honest woman. She kept secrets, rarely if ever gossiped, and considered herself to be an overall decent human being. With all of her might, she tried to ward off the urge to read the text, but she was weakened by her curiosity about this man she'd just been intimate with not even ninety minutes ago.

"I miss you sexy. Where've you been today? Please call me soon. xoxo Evie

Evie? She wondered? She had no claims, no attachments to this man. But, she had way too much self-respect for herself to be on anyone's list of possible hook ups. She found a post-it and scribbled her good byes to him, then grabbed her bag and exited his office quickly. She pressed the button to go down and luckily the elevator opened shortly there after. A man looked up at her and grinned. It took her a moment, but then realized it was none other than Rob Gleason.

"Justine! What are you doing here so late?"

She smiled widely and was genuinely happy to see him. He had gotten his hair cut, but a little stubble graced the surface of his face. She was taken aback by just how handsome he really was. His blue eyes were deep and kind, and she felt a positive vibe from him.

"Oh, I forgot a few things in the office. Luckily I've made some connections to get in after hours," she said sweetly, smiling up at him.

"Yeah," he said shyly, nodding his head and scratching his chin. "I hear ya. I had to stay a little late this evening to finish up a few projects. Are you... um... you got big plans this evening?"

They headed out into the busy sidewalks of downtown Chicago. She could hear blues music drifting out from one of the local watering holes thick with people celebrating the advent of the weekend. She paused in front of the rickety wooden staircase that would lead her up to the El platform that would take her to her cozy condo a little bit south of the downtown area. She loved her sweet little neighborhood in the South Loop.

"Just meeting up with a few friends for cocktails later," she told him quickly. She really needed to catch the next train, but she hated to be rude to such a sweet guy. She guessed he was maybe twenty nine or even thirty. He had a babyface underneath the stubble, and she could tell there was a good physique under his black khakis and gray polo.

"Oh, that's cool," he said, nodding. He wanted badly to ask for her number, but he was such a chicken. Give her a little time, he thought. Or rather, give me a little time. Gotta find some courage. She also looked urgent to get going, so he cleared his throat and made way to exit. "Hey, I'll see you around next week sometime, ok?"

"Definitely," she replied as she made her way up to the El platform. She swiped her pass and just barely made it onto the already crowded car. Her cell rang- a number she didn't recognize.

"Justine speaking," she said above the din in the car.

"Why did you leave me?" Alex. He sounded offended. She decided not to mention the little intrusion of privacy she'd made. The whole matter was changed now- no matter how sick and delicious the sex had been. She'd have to do a little ground work to find out who Evie was.

"I had to rush, Alex. Todd and Braxton need me up to their place quicker than they'd planned, and I didn't know how long you'd be. I thought you'd understand."

"Lucky I had your cell phone number on file," he said, sounding a little dejected. "In any case, I won't keep you. Sounds like you're already on the El. How does Sunday night sound? Is 9 too late?"

She shook her head and closed her eyes, wanting more than anything to say no, at least until she'd had a chance to find out he didn't have a serious girlfriend somewhere out there, but she just couldn't find it in her to turn him down. The sex had been too unbelievably fantastic to turn down.

"Nine it is," she replied in spite of herself.

"I'll text you periodically tonight and tomorrow- just to let you know how I'll be thinking about eating your pussy again- fucking you silly, Justine. God I can't wait."

"Until then," she said huskily, her thighs trembling. She hit end on her phone after he'd said good bye, and gripped onto the bars as the car screeched to a halt. She hoped she wasn't playing with fire.

Meanwhile, Alex decided to take the opportunity to clear his mind. He loved walking in the city back to his condo. He knew he was taking a huge risk getting involved with Justine. It was beyond him how he'd lasted as long as he did. She shook his head in disbelief in thinking they'd only been working together two previous times before today. The afternoon delight had been mind-blowing. He'd found new energy- a new spark in his being when he thought of Justine. There was just the sticky matter of Evelyn. Sam and Piper. God, what was he thinking?

His phone rang. Evelyn.

"Hello, sweetheart, how was your day?" He said, the saccharin sweetness bulging through in high doses.

"Sam has a baseball game tonight and Piper is on her vegetarian kick again- refusing to eat anything I cook! Really, Alex- this whole long distance marriage thing is getting super old. I'm a pseudo-single mom, for Christ's sake! What time do you plan on heading out of the city? It's already going on seven."