Windy City Summer Fling Ch. 02

"Hey sexy mamas!" Justine greeted her girlfriends as they arrived at her condo, margaritas in her hands. "I thought we'd have a few girl moments before we head up north to see the boys. We need to talk."

"Mmmm," Delilah uttered as she took the stemmed glass full of margarita. "Ritas on the rocks? Don't mind if I do."

"There's something different," Simone commented suspiciously as they settled in the cozy living room together. "You. There's something... You're glowing."

Justine scooped up her fluffy gray and white cat Thistle and removed her from the loveseat on which she was going to sit. She tried not to smile, and in order to stifle it, she sipped her margarita, but her friends continued to coerce her.

"Spill it, girlfriend," Delilah demanded. "You know you don't keep me waiting with gossip." She swung her hair over her shoulder and waved her sassy, teal painted finger at her.

"You're about to force Delilah to whip out her sista side," Simone giggled. "Really, my friend. Do tell us. Because I'm kinda getting the vibe that you got laid or something to that affect."

"Not just once, but, like, three times," she gushed, setting her stemware down on the cocktail table. She relayed all of the dirty details to her girlfriends, who oohed and ahhed over her amazing afternoon.

"I've always wondered what it would be like to fuck a silver fox," Simone mused. "I mean, like a hot, sexy, well kept older man."

"Girl," Delilah said, elongating the word. "You're crazy, you know that? Crazy good and crazy bad. Mmm. You sure he ain't got a wife or something? I've had some experiences before. Little did I know." She shook her head emphatically and popped her sensuously full lips together.

Her friends eyed her speculatively and waited for her response. What was Justine supposed to say? She decided that right now probably wasn't the time to tell them about the text message from the elusive "Evie". The voice inside her head told her it was a red flag, but she knew she was too blinded by her lust right now to care. Wife? No. His kids lived with her north of Chicago- there's no way he'd be married still, plus there was no ring... But then not all married men wore a ring... Ugh! She'd worry about it later. The internet was a great tool for finding dirt as needed. Tonight she needed to bask in the afterglow of an amazing afternoon.

"It's casual, girls," she reassured them. "I'm going to enjoy the fact that my four month drought is over, and I'm also going to tell you that I'm going to ride that cock nice and hard again Sunday night as well. So for tonight, let's put all worries aside and rest assured that Justine's a big girl and can take care of drama if and when."

Simone and Delilah looked at one another, shrugged, and raised their glasses with Justine when she raised it in a toast. "To friends, to good times, and to... the penis!"

They laughed as they headed out the door and into Simone's car to head from one end of the city to the other to visit their friends in Boystown.

Todd greeted them at the door looking nothing less than gorgeous. He'd gelled his black hair into a trendy, but subtle faux-hawk. He wore a casual pair of jeans and a white button downed collar shirt with the sleeves rolled up. He accessorized with his silver watch, tiny silver hoops in both ears, and a chunky thumb ring. She'd always found him exceptionally handsome, and even more so when he lined his crystalline blue eyes with a tiny bit of guy liner.

His partner Braxton was clearly just as handsome in a less dramatic way. Tall and lanky just like Todd, Braxton's cherubic face was adorned with dimples, light brown eyes, and shaggy blonde hair. Both men hugged their girls affectionately as they guided them to a delicious spread of Italian appetizers that were the perfect start to a decadent meal.

"Justine got laid," Delilah announced as they all sipped on Cosmos. "She did it, y'all! She got naked with the sexy older gentleman!"

"You gave into your lust," Todd teased. "Hussy."

Justine laughed and tossed her head back, but couldn't prevent the barrage of questions on her first experience with Alex. She had to admit having to retell it and relive it got her a bit excited. She hoped she'd hear from him via a text or something.

"I slept with an older man once," Braxton dished, setting his Cosmo down to talk with his hands. "Come to find out he was on the down low, so to speak."

He looked at Delilah who nodded and uttered "Uh huh... Down low brotherss. They come in all shapes, sizes and colors. I knew it!"

"A house in the suburbs, twin girls, a dog and a cat," he announced. "When he finally grew the cajones to tell me, I'd already figured it out. Just be careful, Sweetheart. Men are dogs."

"Hey!" Todd interjected, slapping him playfully on the thigh. "Not all of us are bad. Look at me- just your average gay dude with no drama. You fell in love with me, right?"

Braxton rolled his eyes and kissed him gently on the forehead. "Of course, Todd, but I'm just saying. For the most part, gay or straight- men can be dogs. But enough of this. Justine, we're dying to hear more details, but my fettucine is ready and I'm famished. Let's eat!"

While Justine was kicking back and enjoying good times with her closest friends, Alex played dad and, well, he tried to play husband, too, but not all of him responded to his wife as she'd hoped. After the kids had gone to bed, and while Alex laid reading in bed, Evelyn showed off for him her new purchases from Victoria's Secret.

She had just turned forty five, and was still trim and in shape. Her new purchase had been a flimsy black lace and satin number that hugged her breasts and accentuated her in all the right places. He admitted she looked gorgeous. She'd brushed out her blonde highlighted hair and lathered on scented lotion for her husband. He'd smiled and admired her, complimented her with all the sincerity he could find, but as she'd reached under the covers to caress and lick his cock, he just couldn't find it in himself to respond.

"But we've not made love in months, honey," Evelyn cried, frustration mounting in her alto voice. "We used to be like rabbits! Jesus, is it me? I realize we've been doing this long distance marriage for the past two years, but recently you've just been so distant."

"It was your idea to move the kids out of the city like this," he said firmly, ignoring the fact that he didn't respond sexually to her. "We had our home, we had our life."

"Right," she replied angrily. "And what kind of life were we allowing for Sam and Piper? The city is no place to raise kids."

"Says who?" He asked pointedly. "I've seen it done."

"But explain to me why you can't make love to me?" She sat on the edge of the bed, tears forming at her eyes. He felt his heart tug, remembering all the ups and downs they'd faced together. He looked at her sad form, face in hands, shoulders slumped. What had happened to them? He felt numb, sad even. He couldn't explain to her what was missing.

"I... I'm not sure, Evie," he replied, closing his eyes to the guilt that had risen within him.

It was later, much later, as Evelyn slept soundly next to him, he glanced over at the clock and it read 3 am. Justine. He wondered what she was doing. Was she in bed? Still out partying? He felt his cock harden. He heard his wife sleeping soundly, grabbed his cell phone, and went downstairs to his office where he locked the door and settled into his comfortable office chair.

"Hello?" A sleepy voice answered, sounded confused.

"Justine.... Hello, my angel," he said softly, feeling his cock harden as he imagined her sleeping form, probably wearing just a little t-shirt, or maybe nothing at all. He liked that vision better.

"Alex? Mmm.... It's late. Are you ok?" She sat up in her bed, looked at the time, and yawned.

"Better now that I heard your voice," he told her. He scooted down in his chair a bit, pulled his hardened cock out from the opening in his boxers, and began to stroke it gently. "Do something for me baby. Tell when what you have on."

"Alex!" She cried. "Where are you? Jesus, what are you thinking? Where are you?"

"Shhhh," he uttered. "I have my cock out, stroking it. I'm achy for you, angel. Tell me so I can feel better, ok?"

"Well, in that case," she replied, relaxing. She settled in and felt herself go moist. She'd done phone sex before. She'd actually enjoyed it thoroughly. "A black tank top. And that's it."

"Take it off for me," he instructed. "I bet you're good and wet."

She slid her hand down and inspected for him. "Drenched."

"Excellent," he whispered. He stroked gently now, imagining her wetness. "Feel me finger your honey. Get your finger nice and wet for me, and lick it. Tell me how it tastes."

"Just like you prefer- nice and tangy," she replied, getting wetter and more excited by the second. "Are you hard, Alex? Tell me what you're doing."

"I'm rock solid, angel," he uttered. "I have my boxers pulled down a little and I'm stroking him. He likes the sound of your voice."

She moaned a little as she entwined her fingers in her wetness. She contemplated grabbing her vibrator, but thought she'd just stick to her fingers.

"I know you're fingering your pussy, baby, but I don't want you to finish, ok?"

"Mmmm, Alex," she purred sadly. "But why?"

"Because when you cum... when you cry out and die a little death right then and there, I want to see your face. I want to hold you, I want to feel your pussy contract around me when it happens."

"But I want you now, Alex," she moaned, thrusting her hips upward as she continued her assault on her clit. "I'm fingering my clit now baby. Just let me finish. Please, Alex."

"How can I say no to you?" He said gently. "Alright then. Imagine my tongue. Imagine my fingers inside your twat, I'm licking you, teasing you..."

"MMM, yes, baby, yes," she moaned.

"I'm sucking furiously on your hard, juicy, pink little clit," he said as he started stroking again. He felt his balls contract. It wouldn't be long. "I'm stroking now."

"Oh, God, YES!" she cried as she reached her peak. "YES! Oh Alex, I wish you were here to fuck me."

"Ugh, yes, my angel, oh FUCK yes," he grunted as he milked his cock. Hot cum shot into his palm and he panted furiously. "Ohhh fuck."

"Mmmm," she sighed contentedly. "The only thing better than this is you right here with me."

"You'll get your wish tomorrow night, sweetheart," he promised, wiping up his mess with a tissue he'd found lying on the desk. "I better go for now, angel. I'll call you tomorrow."

"Good night, Alex," she sighed, hanging up her phone.

Sunday night, after he'd kissed his wife chastely, hugged his kids, and threw the Frisbee for his dog Ozzie, Alex greeted Justine at the door where he took her in his arms, and kissed her passionately. He then slid her yoga pants to the floor, sunk to his knees and took her panties down with his teeth right before he nuzzled her open, sniffed, and smiled, his tongue grazing her stiff pink button. After a few moments, he unleashed his cock, placed her on the edge of the sofa, and drove it home inside her till she cried tears of joy and release. He made love to her several times that night, not giving the life he'd left behind a second thought.

Justine sat at her makeshift desk grading papers when she realized she was in dire need of a Diet Coke. She glanced at the time and realized she had thirty minutes or so before Alex returned, and then they were headed to lunch at English, a pub on State Street. She giggled to herself, wondering how long it would take before they would have enough and just head back to one of their places for another round or four of sex. As she stood and walked past his desk, she paused. She picked up the framed photo of his kids and smiled, wondering what they were like. Did they have his laugh? His intellect? What had caused him and his wife to split? He had certainly never offered up any personal information about himself- in fact, she noted, she knew very little about him. It unsettled her a little, but she shrugged it off and made a beeline to the pop machine for her dose of caffeine.

"Oh, uh, Justine! Hey there!"

She turned with her little can of heaven and smiled up into the familiar face of Rob Gleason.

"Hey, stranger! It's great to see you again!

"Great to see you too," he said gently, his eyes shy, but his voice smooth. He glanced at her can of pop and laughed. "Good thing that isn't opened. I'd hate to have it all over my new shirt!"

She giggled, clutching it carefully. "No worries. I'll open it up back in my office."

Think fast, man. "So, yeah, um, how are things going here for you? Are you liking your summer gig here?" Stay calm. Don't screw this up.

"So far, so good," she replied, noticing how pretty his blue eyes are. "I'm liking the change of pace from teenagers to adults. I'm normally a teacher for Chicago Public."

"No kidding?" His eyes widened and he casually put his hands in his pocket. Relax, he told himself. Just ask her. It's just a question. "Say, um, I was wondering if maybe you'd... you'd like to maybe have lunch sometime?" Awkward. You're fucking awkward, man.

"Well," she smiled, flattered. She had no claims on Alex, and vice versa. Rob was a sweet guy. He was asking her out on a date. What did she have to lose? "I think it would be nice to do that. Maybe getting together on Tuesday or Thursday would be better for me since I try to do most of my work here so I don't have to take it home." Perfect. Then she wouldn't have to explain anything to Alex.

"Really?" He asked surprised, fully expecting her to say no. "I mean, really, you'll have lunch? That's solid! Does tomorrow work then?"

She exchanged phone numbers with him as he promised to call later that night. She walked away and smiled, Alex far from her mind at the moment.

"I have a date," she spoke into the phone to Todd later that afternoon while Alex stepped out to make a phone call outside of the restaurant. "What am I getting myself into here?"

"You're a hot mess," he sighed. "Is this with the silver fox or the computer geek?"

"He's not a geek," she sighed. "He's cute. A bit... unpolished, I'd say. He might be good for me. I've got reservations on Silver Fox." She went on to describe the text message from the elusive Evie. She hadn't found the guts to google her yet. She was afraid of what she'd find.

"Are you still going to fuck him?" he queried, grabbing a pen and paper from his desk. "Say, what's his last name again?"

"Probably later on this afternoon," she sighed. "His last name is Flynn. Please tell me you don't know a man on the DL named Alex Flynn. That would be a hoot, wouldn't it? But just my luck." She thought back to Delilah's story, laughing a little.

"No, princess, I don't know anyone by that name. Curious minds wanted to know is all." His fingers ached to get onto his laptop. As her best friend and closest thing to her brother, he was going to do what she was obviously not. "I gotta bounce now, babe. I'll call you later, ok?"

Alex returned, his smile sly as he bound back to the table. "That was my son. He wanted to brag about the two homeruns he made today. Chip off the old block, I tell ya."

"Awesome," she smiled. "You don't really talk about your kids much. Do you see them often?"

He felt himself tense. Careful. Be very careful. "I try to see them, oh, at least every other weekend or so."

"They're how old?" She took a sip of her water and saw that his body language had changed a bit.

"Sam is thirteen and Piper is twelve," he said quickly. "So, you ready to rock and roll, sexy?"

"Well, I just had one more question," she said sharply. "You're so elusive about your personal life. I don't even think I know your favorite color, or... or, where you went to college? How long have you been divorced?"

"Divorced?" He asked with confusion. He looked at her, his eyes like spinning saucers. Then, it dawned on him that he'd told her the kids lived in Rockford with their mom. She'd assumed they were divorced. "Oh, um, yeah. A... a few years. And, I like the color green and I went to Northwestern. Anything else?" He winked, rubbed her ass subtly, and whispered into his ear that he wanted her very badly.

"There's a lot, actually," she said as they walked out into the city. "I guess when I get naked with someone, it's not just physically."

He stopped, sighed heavily, and bent to her, putting his hands on her shoulders. "I made it clear after the first time we were together that this would be casual. I like you a lot. You're young, vibrant, exciting, sexy... everything that could possibly turn me on. Let's just do this day by day, minute by minute. I know this minute, I want you. I want to take you in my arms and make love you to, laugh with you. Haven't you ever just thrown caution to the wind and followed your heart every so often?"

She met his eyes and watched them search hers carefully. He made a point- a very interesting one. She longed to ask him about Evie, but that would spoil things fully and completely. She had to admit this... this fling... had been like nothing she'd experienced. She'd been swept off her feet by a sexy older man who could turn her knees to pudding. He was not only a magnificent lover, but smart and dedicated to his craft. She admired him just as much as she lusted after him.

They had switched things up a little and had gone back to her condo for a few hours of unbridled pleasure. She bent before him as he sat down on her couch. She caressed his knees and thighs before slowly undoing the fly on his jeans. Her eyes not leaving his, she undid her black blouse, undid her bra, and took his hands and placed them on her naked breasts. He sighed, murmuring words she barely heard as she pulled his jeans down, exposing his fully erected hardened flesh. She licked her lips, anxious to put his warm flesh into her mouth. She moistened it with her tongue, then pulled him towards her. She took his cock and rubbed it against her breasts. She moistened the tip again and rubbed his cockhead against her nipples- exciting them to little nubs of marble. With her free hand, she reached for his balls, rubbing them gently. He moaned, closing his eyes and just giving over to his senses. He turned his mind off and just zeroed in on her mouth, her breasts... all of her.

Later, he mounted her from behind, dominating her. He thrust into her wickedly as she cried out. She moaned in ecstasy when he rubbed her clit in unison with the thrusting of his bold cock. When he exploded inside of her, he pulled her hair and cried out her name as she fell off the precipice right along with him.

Later, after they'd enjoyed each other's bodies for over four hours, they lay snuggled in her bed, lying in silence, till at last he broke it. "I wish we could stop time- just for a week or so. I would stay right in this condo with you- making love, reading Shakespeare, sipping wine. No worries, no obligations whatsoever. I know it's hardly possible, but I imagine what it would be like." His voice was weary, distant even.

She ran her hands up and down his bicep, kissing it, feeling its strength. "You sounded sad just then."

"Sad? No, not sad, really," he sighed, turning and holding her close to his body. "You're young, Justine. You have so much ahead of you. Myself? I'm old. At that age, I guess, where I wish I'd done a few things differently. Not that I have regrets- I don't regret my children. They're amazing. I just look at my life now, and wonder where it all went."

"Tell me about their mom," she blurted, finding the guts to finally ask. He stiffened at first, then sighed. He was quiet for a long time, as though gathering the courage. "I... I don't mean to pry..."

"No, no," he said uncomfortably, then she felt him relax. "It took us... awhile... to conceive. Before she became a mom, she was a workaholic- you know the kind. Type A kinda gal- had a high stress job at a Wall Street based company. She was up all hours of the night trading. High sex drive. I wanted kids earlier than what we did, but she was very career minded. Sam came along and she fell in love with being a mom. She quit her job, and Piper came soon after. We had a nice little three flat on the north side, but she didn't want a life in the city anymore. It hurt like hell that she wanted to go, but she had it in her mind that it would be better for the kids in the suburbs. I couldn't argue... So she left."