Windy City Summer Fling Ch. 03

Story Info
Justine finds love, but is thwarted by lust for Alex.
4.5k words
4.3
8.6k
5

Part 3 of the 3 part series

Updated 10/07/2022
Created 06/13/2010
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"Ugh, kitty, come on," Justine groaned as her cat jumped onto her bed, began purring, and adjusted herself, plopping right above Justine's head on her pillow. "Really, Thistle? This is my morning to sleep a little." She glanced over at the clock as it read 8:30. Thistle purred, meowed and laid her head on the pillow. Justine caressed her satiny gray coat and smiled as her feline companion closed her eyes in contentment.

She let her mind wander a little. She enjoyed these precious moments where she could linger in bed without having to race off to work. Alex came to her mind as she imagined him in this bed next to her. No doubt he would've awakened her with his hands, his mouth.... She felt herself go moist and in spite of herself, she let her hands wander to her excited womanhood... With her finger she toyed with her clit, imagining Alex's tongue there. She moaned a little, feeling herself go wetter. She alternated between her clit and her soaked slit, pressing her middle finger up into herself. She closed her eyes, her mind's eye replaying the image of her riding Alex's hardened cock to ecstasy. With her pointer finger, she jiggled her precious pearl, sending herself into waves of passion. She sighed gently, bit her lip, and stretched. Alex was a tremendous lover- handsome, experienced, with a delicious hard cock and a willing tongue. She tried with all that was in her to ignore the fluttering pangs that all was not right with this situation. Evie. It still bothered her. While her body yearned for him, her heart was trying to warn her, all the while her head was siding with the body for now. She sighed, wishing things didn't have to be so damn complicated.

She smiled then, thinking about how later this day she would be hanging out with Rob Gleason. If anything, he would be a gentle distraction from her lust for Alex. She arose from her bed, sauntered into her kitchen and glanced at the flashing red light on her phone, alerting her that she either had a missed call, a voice mail, or a text.

"Missed call from Todd," she said to herself. "I'll check his message after I shower." She yawned as she opened a cold diet Coke. She glanced out of her window again, admiring the clear blue skies and sunshine that lingered in the city.

After her shower, she slipped into her cotton robe, not quite sure yet what to wear as the decision for her date with Rob had yet to be determined. As if on cue, her phone rang.

"Hey there," Rob spoke. "Dentist appointment cancelled. What do you want to do today?"

"It's a beautiful day in Chicago," she grinned. "How about we meet at North Avenue Beach around 11:30? Castaways is there. We can grab lunch, walk on the beach- just kinda play it by ear. Sound like a plan?"

He grinned, loving the sound of her sweet, yet sexy voice. He imagined her greenish brown eyes. He loved how they sparkled a little. He had such a huge crush on her. He just didn't want to screw anything up.

"Sounds great," he said. "See ya soon."

"Absolutely!"

She chose her one piece black swimming suit- the one that cut down low and showed off her cleavage. Over the top of that she threw on a hot pink cover up that looked like a sundress. She shoveled out a beach bag from the back of her closet and filled it with a few necessities, along with panties and a bra, and shorts and t-shirt in case they wanted to go anyplace else besides the beach. She spritzed her hair with a little hairspray, slipped into black flip flops, and headed out the door to her date with Rob.

She hailed a cab and jetted up along Lake Shore Drive. Sunshine illuminated the skyline, and as traffic slowed in front of Grant Park, she saw families and tourists snapping shots of Buckingham fountain. To her right, people jogged, walked, and biked along the path in front of Lake Michigan, which was calm and a perfect shade of blue. She watched boats bobbing along, their passengers decked out in bikinis, swim trunks, and shades. She wished she was on one of them. At long last, traffic moved, and the cab driver made his way the beach where North Avenue ended by the lake. She handed him the fare, and as she got out, she marveled again at the beauty of the city behind her. Slinging her beach bag onto her shoulder, she saw that others had had the same idea as her today. She scanned the crowd near the outside beach bar. Leaning against a table was none other than Rob.

She marveled to herself at just how good looking he really was. He was tall and nicely built- at least 6'5 or so. He wore black swim shorts, a gray Chicago Blackhawks t-shirt, and flip flops. There was something so endearing and welcoming about him. She smiled in spite of herself as she made her way to him in the crowd.

"Hey stranger," she smiled. His dark brown hair was gelled and he had a little bit of a scruff on his gentle face. "Ready to be a beach bum?"

He leaned down and hugged her. She smelled so sweet- like oranges. He tried not to be nervous, but oh shit, he was! "Is it too early for a cocktail?"

"It's our day off," she giggled. "How about a margarita?"

He returned with two tall plastic cups filled with icy cold liquid. She commented on his t-shirt.

"I was never much into hockey till this year when I watched all the championship games and we won the Stanley Cup," she explained. "I didn't realize it was so fast paced!"

"Hockey is my family's sport of choice," he explained as he felt the calming effects of the tequila. "I used to play when I was little."

"No kidding?" She later learned that he'd grown up on the south side of the city, and later one of the southern suburbs. When he'd landed the job in the city, it only made sense for him to move downtown to be closer.

"I hate commuting," he explained. "I'd much rather hop on the El and be done with it. I hate driving in all that shit. I have a nice condo in the Lincoln Park area. You're in the south Loop, right?"

"Yup," she nodded as they found a patch of sand on which to park themselves. He unfolded a blanket onto which she threw her bag. She stripped off her cover up dress and tried not to notice or giggle when Rob's eyes grew big. On cue, he shed his t-shirt, and she saw the tattoo that graced his left shoulder. She bit her lip, and his appeal just grew tenfold. She was a sucker for men with ink. "Awesome tattoo!"

"Oh, thanks," he said bashfully. "A lot of people say I'm not really the tattoo kinda guy being a computer geek and all."

"I think tattoos are very sexy," she flirted, sipping her margarita and winking as he looked over. "I kinda like that whole good guy with a bad side thing."

Rob turned to her and grinned as she rolled onto her tummy and looked up at him. He leaned back onto his hands and looked down at her. He had formed a crush on her the first time he'd ever seen her. Now, as she lay in front of him in a very sexy black swim suit that enhanced her very feminine, very ample curves, he nearly felt himself go hard. She had that classy, old film from the 40s or 50s kind of appeal. She was a real woman- not some skin and bones type that nearly every shallow man desired. He could almost see her as one of those retro pin up girls that had ample bosoms and scarlet lips.

"Why did you get so quiet?" She pondered, raising her sunglasses to look at him. She bit her bottom lip in admiration of him in his mirrored aviator sunglasses. She saw a totally different guy here on this beach. Not the quiet, absent minded shy guy she'd bumped into one day.

"Oh," he said quietly. "I was just thinking that maybe... I'd just do... this!" He flicked the remainder of ice from the cup of margarita, and it sloshed her on her shoulder. With that, he got up and ran as she chased him to the shore of the water.

Once they were there, she splashed him playfully, and truth be told, she loved the feel of him- his skin, his hair- and his hands on her body were quite pleasant, as well.

"You're such a cutie," she giggled, wiping water from her face and they both stood, breathless from their silliness.

He laughed softly, a tiny blush coloring his handsome face. He took his sunglasses off, and she saw his gentle blue eyes glisten. "I have a huge crush on you, Justine," he said softly. "You're so pretty, and you're so nice. I really like you."

She stood with her hands in his, totally unable to speak as a warmth spread across her heart and made it skip a beat. It was that feeling that she'd forgotten existed- like that feeling when you're a teenager and your crush turns around and smiles at you, making your knees go weak and mushy. This was the feeling every woman thrived on, longed for. She'd been so used to jerks and men ready to take her to bed- none of them willing to actually take the time to make her feel special. With that, she caressed Rob's stubbly cheek, looked into his eyes and smiled a genuine smile.

"I really like you, too," she replied softly. She let him pull her to him and kiss her gently on the lips, nose, and forehead.

He smiled, kissed her again gently, and then splashed her playfully, taking her fully by surprise.

"That's, it, mister!" She chased him out deeper into the lake only to have him turn and hold her closely to him. It was a feeling she didn't want to have go away.

Later on, after a quick lunch from Castaway's of a cheeseburger and fries, she slipped into the women's locker room to change into a soft pink tank top and gray shorts. She quickly powdered her face, applied a tiny bit of blush and lip gloss, and walked out only to find Rob waiting for her in khaki shorts and a black t-shirt. His hair was still wet, and she smiled hugely when she saw him.

"You look real nice," he said sincerely. "Even though your hair probably smells a little like Lake Michigan."

"No thanks you," she laughed wickedly.

" I thought maybe we could head down by the museums. Take your pick- we can do the Field Museum, the Adler Planetarium, the Shedd Aquarium, or even just walk around by Soldier Field. Please tell me you're a Bears fan?"

"Do fish like water?" She giggled.

He let out a sigh of relief as he opened the door for her to his silver Toyota. They chatted away like it was an old habit of the two of them being together like this. Justine felt comfortable and relaxed. Although she found him sexy and attractive, the urge to jump his bones was not at the forefront. She was certain it would be there later, but for now, it was more pleasurable to enjoy his company than anything else.

They parked in a lot a few blocks from the lake behind the Bears stadium and decided to enjoy the gorgeous weather with a long walk by the lake, and then they would decide what to do with their time.

"My friend Joe has a boat he has parked at one of the marinas around here," he told her. "He's going to take it out with a big group of our friends this Saturday. Would you like to come?"

"Oh, would I!" She said excitedly. "I think that sounds amazing!"

"Awesome," he said excitedly, then more gently, he added. "Justine, I meant what I said about really liking you. I'm not one of those jerks, ya know. I'm not just looking for a quick roll in the hay."

"That's good to hear," she said sincerely. "I'm thirty two now, and I'm exhausted with men my age acting like they're twenty one."

"Well, I just turned thirty," he replied. "I can't promise you I don't act a little juvenile at times, but not in a way that would ever hurt you."

"Oh, do tell," she asked curiously.

"Oh, just the usual stuff," he said, laughing. "Video games, Cartoon Network, bright shiny objects that catch my attention... pretty girls like you who make my heart skip a beat."

She batted her eye lashes and flirted shamelessly, fully enjoying this kind of attention. As she walked on, chatting with him and using her hands animatedly, she truly didn't see that she was walking towards the edge of the sidewalk. As she turned to face him, her flip flop caught on the edge of the concrete, causing her to twist her angle as she fell downward.

"Oh, shit!" she cursed as she rubbed her leg. "You must really think I'm a klutz."

Rob quickly helped her up and held her closely. He noticed tears forming at her eyes as she began to laugh ironically. He wiped her tears away, but didn't let go.

"Can you walk?" He held her by the waist with one hand, and her arm with the other. "You're hardly a klutz. I just want to make sure you didn't break anything."

She tried to move forward, but a vicious pain shot through her foot and ankle. She was able to hobble with his aid, and she was grateful that the car wasn't far.

"I'm afraid I've made a mess of our afternoon," she said dejectedly. "Look, if we go back to my place, I can get this thing wrapped and we could order some food if you want."

"You sure you don't want to go to an emergency room?" Rob asked cautiously, noticing that her ankle was starting to swell. "I just want to make sure you're ok, but if you don't, I'm totally fine by hanging out with you at your place."

After what seemed like ages, Rob helped her up to her second floor condo, sat her in her comfy lounge chair, and went to her freezer. All he could find was a bag of peas, but as he held it at her swollen ankle, it definitely took away the pain.

"You're an angel," she said softly as she swallowed down a few Ibuprofen to help take down the swelling. "I'm so sorry I ruined our first date."

Rob laughed as he checked her foot once more before coming to sit with her. "Justine, I never thought someone as pretty as you would ever give me a chance. I'd turn myself into a mosquito and fly across a pond of hungry frogs if it meant I could spend some time with you!"

Justine bit her lip and smiled at his comment. She motioned with her finger for him to sit next to her in the big, over stuffed chair. It was the perfect opportunity for the two of them to be close. He wrapped his arm around her as she looked up and motioned him closer to her upturned face. She caressed his face before he kissed her gently, and then the kiss became more heated.

"It's kinda hard to kiss you on this chair," he said breathlessly.

"Then let's go to my bedroom," she suggested. "Help me up, please?"

Rob sighed, ran his hand through his hair, and shook his head. "Are you sure you want to do this, Justine? I mean, it's our first date- I don't want you to think—"

"There's no pressure," she sighed as she longed for him to kiss her again. "And I wouldn't think you were just trying to get in my pants. Trust me, I know how that particular event goes."

"I'm not that kind of guy," he said gently as he kissed her neck and began to caress her breasts through her very thin tank top and bra. "My God, you taste so good..."

Their kisses became more intense as hands began to find places best explored on a bed. Together. She entwined her hands through his thick, dark hair as his hands crept up her shirt, under her bra. Her breasts were tender, yet hard as jewels as he tweaked them and teased them. She dared to put her hands between his legs. He was hard.

"You sure you don't want to go to my bedroom?" she said between kisses on his neck which she knew was driving him crazy.

"Point me in that direction," he smiled a wide smile, his large white teeth sparkling. "I'll help you up."

He helped her hobble into her bedroom where she flipped back and pulled him on top of her. He kissed her chest and laid his head between her breasts. He looked up at her, his magnificent blue eyes pulsing with admiration. With his eyes never leaving hers, he carefully undid her shorts, pulled them down deliciously, torturously slow.

"You're so wet," he said incredulously as he carefully bobbed his finger down into her. He cocked one eyebrow and sampled her only to have her moan pleasurably. Seeing how much she liked it, he put his finger back in that sweet place, found her hardened clit, and began to move upon it quickly.

"Oh, my," she inhaled sharply, digging her fingers into his upper arms. "So wonderful."

"You feel so wonderful," he whispered as he bent to kiss her. He continued his delicious torture on her hardened clit only to have her erupt in cries of ecstacy mere seconds later.

"I... I've never cum so quickly before," she exhaled, pulling him down to kiss her. "Maybe you should get undressed?"

He lay next to her, held her close to him, brushed her hair away from her contented face. "I want to wait," he said gently. "When I make love to you the first time, I want it to be special- something you'll never forget. I'm old-fashioned, I guess. I wasn't lying when I said I really like you."

She smiled, feeling that sensation in her stomach again- one she'd forgotten she'd loved experiencing. She'd been hurt so often by men who were simply after one thing. It was few and far between to find someone like Rob.

Later, after having polished off a pizza and a few bottles of beer a piece, and several episodes of South Park, Rob glanced at the time and realized he needed to head back to his own place.

"You know, Justine, you're every man's wet dream come true," he said as he stood and reached in his pocket for his keys.

"How so?" she giggled as she stood carefully on both feet. Earlier, Rob used his trusty Boy Scout techniques and wrapped her sprained ankle in an Ace bandage they'd found in her vanity. It was already feeling better.

"Not only are you fucking sexy as hell, but you drink beer, you laugh your ass off at South Park, and you dig sports." He shook his head incredulously.

"I'm one of a kind," she said seriously. "They broke the mold after me."

He reached for her waist, gathered her into him, and kissed her gently, sweetly, his tongue lingering. "I'll be working at a different location for the next week or so, but I'll call you tomorrow. Definitely this Saturday for boating, right?"

"Yes," she said, feeling almost a tad bit relieved hearing he'd be working elsewhere. Alex. Things were about to get complicated. She wanted Rob. She wanted to eat more pizza, drink more beer, watch more silly cartoons, and go to Bears games and Blackhawks games with him. He made her feel beautiful, admired, and best of all, he reminded her of what she'd always wanted before others had jaded her. "I can't wait to see you again."

"Me, either," he said as he kissed her once more and headed out the door.

She glanced at the clock and was surprised to see that it was already ten o'clock. Carefully she moved to her kitchen and found her purse to retrieve her cell phone, which she'd had on silent all afternoon. She was cautious, and hadn't wanted to be interrupted by Alex, who she was certain had called or texted.

"Eight missed calls and ten text messages," she uttered to herself. All from Alex. As she began to read through her messages, the buzzer rang at her door. Thinking it may've been Rob, she limped to the intercom, fully expecting his sexy voice.

"It's Alex, gorgeous, please, I need to see you."

She sighed, bit her lip, and pressed the button to let him in. Within seconds, he was there. As she opened the door, he was a mixture of relief, annoyed, and lust.

He grabbed her and kissed her passionately, caressing her breasts and moving her towards the couch. "I've been trying all fucking day, Justine. God, I just need to take you, feel you underneath me, taste you..."

"Ouch!" She cried as she stepped wrong on her injured foot.

"Did I hurt you?" he asked quickly as he began to undo her shorts. He was too quick for her. He was already fingering her and despite her earnest efforts to push him away, she couldn't.

"I- I was jogging today and I hurt my ankle," she uttered, but he dimly heard her. He was already on top of her on the couch, kneeding her breasts and licking her exposed tits.

"Mmm," he sighed. "I hope you're ok. Why didn't you answer my calls?"

"Because," she sighed, trying to push him away, but her body was answering the call to his lust. "I- I was busy, and I... oh, Jesus... Alex..." It was too much. As her head said no, her thighs opened to his touch.

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