These are the stories of Kelly MacGuire.
She was in her mid-thirties when Dan met her, had been married four years, and had one child, Evelyn, two years into the marriage. She used to work as a consultant to the computer industry for the Chicago office of a major consultancy, where she met her husband, Mike. However, after Evelyn was born, she never went back to work full-time. She did, however, remain working on a contract basis for the company, helping it recruit at various colleges and business schools around the country.
In what remained of her time, Kelly chose instead to take care of Evelyn, as she and Mike didn't need the additional income. He made plenty of money to maintain their three-story, Lincoln Park walk-up and a pair of European imports. They traveled often, and he kept her in stylish clothes and beautiful jewelry, not the least of which were her engagement and wedding rings. The engagement ring was a 3-karat emerald cut diamond in a platinum setting with baguettes completely covering the band. Her wedding ring matched the engagement ring in both beauty and extravagance.
The young woman was a bit shorter than average but kept herself trim and fit through an almost daily regimen of exercise and a proper diet. Her breasts were significant and hadn’t started to droop at all, though given their size and six months of breastfeeding Evelyn, they aren't exactly pushing up her chin, either. But they are beautiful, sitting proudly on her chest, capped with wide, light pink areolas and thick nipples that tended to grow thicker and almost obscenely elongated when she was sexually stimulated.
But to look at her, one would never associate Kelly with the word "obscene." She had the face of an angel, and looked strikingly similar to Josie Bissett, if you can reach back in your memory to Fox's "Melrose Place." Her eyes were usually baby blue but sometimes appeared brighter than that. Her hair, a shade or two lighter than dirty blonde, hung just past her shoulders, but she occasionally wore it in a ponytail. She usually didn’t wear too much makeup, insofar as her natural beauty didn’t require it, but her lips were often smeared with a muted pink or subtle red lipgloss. Put her in her typical “Lincoln Park mommy” outfits – stylish capri pants, a sexy but still reserved blouse, a pair of Tod's moccasins – and you would never suspect what lurks beneath Kelly's conservative façade.
These stories are about what lurks beneath. In her heart of hearts, Kelly understood and reveled in the fact that she was an adulterer. She was highly sexualized and thought nothing of cheating on Mike whenever the mood struck her – which was often – and had thoroughly discarded any semblance of adherence to her marriage vows, and to any norms of morality, as well. Both before and after she met Mike, many men had pawed her breasts and nipped their teeth at her engorged nipples. Her pussy – which she religiously waxed (Mike thinks it's for his benefit) – has been eaten and stretched by men from all walks of life, young and old, and all manner of cultures – and colors. Nor was her anus off limits, having been invaded by cocks long and short, fat and skinny, white, black, brown and yellow, young and old, not to mention more than a few inanimate objects.
What might be even more surprising than her continuous acts of infidelity was the relish with which she attacks each act. Too many beautiful women are lifeless in bed; they have bodies to stir the interests of any straight man and many curious women, but the imagination, enthusiasm, and aggressiveness are missing.
Not so with Kelly MacGuire. She begged for it. Her appetite for sex was nothing short of ferocious. Some of the things that came from her mouth would stupefy the average listener. And it went beyond that. Kelly certainly understood her own mind, her unquenchable thirst for sex, but she also demanded, in her own underhanded way, that her partners did, too. Only when they have grasped this – only when they reminded her of what she is, of what she was doing, of how immoral and indecent her behavior was – did Kelly really reach her pinnacle. Yes, Kelly begged for the physical release, but also for the psychological release brought on by degradation and humiliation.
When engaging in these acts of infidelity, Kelly was prone to flaunt her marital status, and her left ring finger was always adorned with her engagement ring and wedding band. It didn’t matter one whit to her that that hand may have been wrapped around a thick, black cock in the back room of her parents' country club, or guiding a long cock up and into her hairless pussy as her seven-month-pregnant body straddled a freshman college student in his dorm room, or inserting a finger in her anus while being pounded from behind by an immigrant Cuban in a run-down flat off Calle Ocho in Miami.
Though Kelly often sought out strange men while dressed in upscale-mother attire with just a smear of color across her lips, she would occasionally be found with blood-red fingernails and heavy lipstick to match, tight tank tops with her huge breasts bulging out the sides, skin-tight leather pants or mini-skirts, and stilettos that bordered on slutty and screamed: “Fuck me.”
Many strange men have taken Kelly MacGuire up on this offer. Too many to count, and too many to fully recount here. The stories here, however, are some of the highlights, embodying some of Kelly MacGuire's sluttiest, filthiest, and most obscene sexual deeds as a married, but not even remotely faithful, mother of one.
*
Being one of the last big summer events before Labor Day, the Chicago Air and Water Show always provided for a fun weekend. Marc, one of Dan's best friends, owned a condo in Bucktown just north of Division Street, and every Saturday of the Air and Water Show, he threw an all-day party. He lived on the top floor of a newly constructed three-flat, and a stairway from his living room led up to a private deck that spanned the entirety of the roof. The party would usually start in the late morning and continue throughout the afternoon and evening. The great thing about Marc's Air and Water Show parties was his proximity to one of the flight paths: his condo sat just below one of them, and throughout the afternoon, all manner of planes – from streaking F/A-18 fighter jets to World War II-era prop planes – passed directly overhead.
True to form, Marc's party for last year’s Air and Water Show was another great one. Dan went over early on Saturday to help him at the grocery and liquor stores, and then to set up. Several trunk-sized coolers on the roof deck supplemented a beer refrigerator inside. A large gas grill smoked most of the day, laden with burgers, brats, chicken, and steaks. From beginning to end, about seventy-five people would attend this party.
Midway through the afternoon, Dan sat at one of the tables on the roof deck, talking with a group of friends. Some of these had gone to college with him and Marc, and others they knew from their respective jobs. Marc's older sister, Belinda, was also at the table talking with some of her friends. As a lumbering Air Force C-130 passed overhead, Dan turned west and watched its image recede.
He was about to turn back to the conversation at the table when a striking blonde walked through the door and out onto the roof deck. She glanced around, as though looking for someone, and a bright smile formed on her lips as she waved in Dan's general direction. Looking behind him, Dan heard Belinda shriek, and saw her wave back, and get up. Dan leaned toward Jeff, who was sitting next to him.
"Who's that?"
Jeff turned to look toward the blonde newcomer, and said, "Not sure. I've seen her before. I think she's friends with Belinda."
Dan turned his attention back to the athletic body bearing an angelic, almost regal, face. As she walked toward the table, he took in the tanned and toned legs that protruded from beneath a white, pleated tennis skirt; footy socks with pink cotton balls at the back and Nike tennis shoes covered her feet. She wore a pale blue polo shirt that hung loosely but still gave away the fact of her large breasts. Flaxen locks were pulled back in a ponytail, revealing flushed cheeks.
When she and Belinda met on the other side of the table from where Dan was sitting, they embraced in a big hug. "Hey, Kel, what took you so long?"
"I had a long session with my tennis pro. I thought I'd get here earlier, but he kept me longer than I thought," Dan overheard the girl reply in a soft, sweet voice.
"Well, let me introduce you to everyone. Everyone, this is Kelly, a good friend of mine from college. Kelly, this is Nancy, Marie, Jeff, Dan, Christian, and Matt. I think you may have met Nancy and Marie before; the guys are friends with my little brother." Kelly gave a shy wave to everyone at the table; Dan could not help but notice how strikingly blue her expressive eyes were.
After everyone said their 'hellos' and 'nice to meet yous,' Belinda said, "Hey, let me get you a drink. What do you want? We have wine, a bunch of different kinds of beer, some White Claws. There's also vodka and whiskey, mixers, too."
"White Claw sounds good."
Kelly moved to a vacant chair at the table and sat down while Belinda went to get her drink. Crossing one trim leg over another, the tennis shoe bouncing to the rhythm of the music coming from the stereo, she struck up a conversation with Nancy and Marie, whom she had in fact met before. Dan stole a few surreptitious glances her way but, not wanting to be obvious, returned to his conversation with his friends. When Belinda returned a few minutes later, Dan saw, from the corner of his eye, Kelly reach for the bottle. He turned his head her way and watched as her long, tanned fingers gripped the dripping bottle. The light pink polish on her nails appeared almost transparent, but what Dan noticed more immediately was the huge diamond gleaming on her ring finger.
A Blue Angels F/A-18 streaked above the roof deck, casting a fleeting shadow as it did. When the plane had cleared the area and people could talk again, Dan again joined his conversation, but still heard Kelly say in response to an unheard question, "Yeah, he's pretty wonderful," as she took a pull from the can.
"Where is he now?" Nancy asked.
Swallowing, Kelly said, "He's down in the Carolinas with some friends playing golf. Some sort of guys' weekend. I can't wait for him to get back, though. He's been gone since last Saturday."
"When’s he getting back?" This from Marie.
"Tomorrow night, late. Thankfully, my parents have Evelyn for the weekend, so I've had some peace and quiet." From there, the conversation among the women at the table devolved into babies and work, and Dan stayed attuned to his own conversation.
Over the next several hours, Dan mingled with various groups of people, sometimes sitting at the table, but moving around the roof deck and into the condo. He would occasionally see Kelly talking with this group or that, and often stared too long at her classically beautiful features – or her generous breasts, or shapely legs, or tight little butt.
By the time nine o'clock rolled around, Dan was pretty beat. He'd gotten up early to help Jeff with the party, and started drinking around eleven that morning. The alcohol, combined with the hot, August sun, left him ready for bed. He found Jeff and said his goodbyes, and talked to a few other people before bounding down the stairs and into the condo. Approaching the door, Dan ran into Kelly, almost literally. She had a tennis bag slung over her shoulder, the strap crossing between her breasts, accenting their prominence.
"Takin' off?" he asked, as he held the door open for her.
"Yes. I've had a long day and just want to get home and relax," she responded, as she descended the stairs, Dan following her down. "Too much alcohol and sun whipped me," she said over her shoulder.
"I know what you mean. That's why I'm outta here with you."
On the sidewalk, Kelly looked both ways, as did Dan, waiting for his Uber to arrive. “You, uh, ordered a car, right?” he asked. “I mean, it’s not a bad neighborhood at all, but you know how it can get over here.”
The woman chewed her lip pensively. “I tried…twenty-minute wait. I guess I figured I could find a cab.”
Dan was shaking his head before she’d even finished. “No…we’re not gonna let that happen. Where do you live? Kelly, right? I’m Dan, by the way.”
“Yes…I remember…I live in Lincoln Park. Not too far from here, really. Armitage and Sheffield.”
He nodded as a black SUV pulled onto the street and glided to a stop at the curb. "I'm just north of there. Come on. We’ll drop you near your place. I don’t want you walking around this time of night."
Kelly hesitated. “Are you sure?” she responded, stepping off the curb behind him. “I don’t want to be a burden.”
Dan opened the door and held it for her. “Don’t be ridiculous. Get in.”
Kelly thanked him and eased past him and began to climb into the big SUV. Dan marveled at the way her tennis skirt swooshed back and forth over her firm bottom as she leaned in to put her tennis bag and racquet on the back seat, then climbed in after her.
On the way over toward Lincoln Park, Kelly and Dan made small talk about their lives, comparing notes on their neighborhoods and rising real estate prices. As the Uber neared Clybourn and Sheffield, it got snarled in traffic. Dan peered through the front window and sighed. "We could be here all night." After a pause, "Tell you what. You're not far from here, let's just get out and walk. It'll probably be faster."
After the driver pulled the SUV to the curb, Dan and Kelly got out and started walking up Sheffield. A few blocks on, she pointed toward an alley and veered that way. "Let's cut through here. I'm on the next block over." Dan followed her into the alley.
"It's not safe to walk through alleys at night, you know," he said in a playful tone as they walked through the garage-lined alley.
"I know that. But I've got you as my protector, right?" she giggled, lightly bumping her shoulder into his arm. Her soft voice was almost rousing. "Thank you for letting me ride with you, by the way. That was very nice of you. When we get to my house, I'll dig my wallet out of this bag."
"Seriously…stop, it was my pleasure."
Kelly again bumped her shoulder into him, but this time with a bit more force. Dan wobbled a little, away from her, and Kelly followed him, using a little hand to gently shove him up against a garage door. When Dan's back hit the door, her other hand joined the first, and Kelly, up on her toes now, leaned in close to him; he could feel the softness of her full breasts press against his ribs.
"Your pleasure is right," she whispered, letting a hand drop down Dan's chest, over his stomach and waist.
Through his shorts, Dan felt her dainty hand search for and discover his cock, which she gently kneaded through the fabric, her full, pink lips landing soft kisses along his neck.
"Jesus," Dan murmured.
Feeling his cock thicken under her manipulation, Kelly's manicured thumb and forefinger found the zipper of Dan's shorts and eased it down. Her long fingers wormed their way through the opening and into his boxers before pulling his cock out into the muggy night air. Gripping the lengthening shaft in her small hand, she began lightly jerking it as it swelled in her palm. "Mind if I suck on it?" she whispered into his ear, blowing hot breath as she did, sending chills up Dan's spine.
Without waiting for an answer, Kelly dropped into a squat, her tennis skirt ruffling in a breeze that blew down the alley. Her left hand still stroking at the base of Dan's cock, Kelly's pink lips parted and her soft wet tongue darted out, taking a quick swipe at the cockhead. "Mmmm," she moaned before her pretty mouth opened wider and engulfed his now-bloated head. She bobbed her head up and down a few times, leaving his shaft slick in her saliva.
Dan looked down to see the end of his burgeoning cock disappear between the woman’s lips. Kelly placed her free hand on his ass, pulled the rest of his cock into her mouth, and began a slow in-and-out rhythm, twisting her soft lips around the now-swollen shaft. He placed a hand on top of her head and she increased the pace at which she was sucking him. Kelly's hand dropped from Dan's ass and disappeared underneath her tennis skirt; when he heard her take a sharp breath through her nose, Dan knew her dainty fingers had found her clit.
Three garage doors down, a light flickered on, and the grinding sound from an aging garage door opener pulled Kelly's mouth from Dan's shaft and her fingers from her clit. A strand of spit hanging from her lower lip, she quickly stuffed Dan's cock back through his zipper opening, and moved away from him, picking up her tennis bag as she wiped her mouth.
"Come on. Let's go back to my house," she said over her shoulder, leading the way down the alley, her tight little butt swaying beneath her tennis skirt. Where the alley met the street, she took a right and walked a few doors down, then bounced up the entry steps to a three-story walkup of 1930s vintage.
She keyed the door and Dan followed her in. The structure may have been built decades ago, but the interior had been rehabilitated more recently. Spread out before him was a living area straight from a contemporary interior design showcase. But Dan barely had time to study the front portion of the home. As soon as Kelly had shut the front door, she dropped the tennis bag at her feet and without saying a word, led Dan by the hand past the front room and halfway down a hallway, pulling him into a home office.
In one corner of the office sat an antique partners' desk with a Tiffany lamp casting a soft glow throughout the room. Across from the desk were a leather club chair and a matching couch. The walls above the chair rails were painted the hue of felt on a billiards table, with deep oak paneling below. Built-in bookshelves held volumes from Brad Thor, David Baldacci, and other such notable authors, various trinkets, and pictures of Kelly and a man about her age, and of the two of them and a toddler. Golf prints – one from the 2021 British Open at Royal St. George caught Dan's eye – adorned the walls.
Kelly pulled Dan onto the couch, and sat on his left, facing him, tucking a leg beneath her. When he settled and his mouth opened to say something, her bright blue eyes smiled into his, and her left hand reached out and cupped the side of his face, pulling it toward her. Their lips met, and Dan felt her sensuous tongue slip into his mouth; he moaned into her, blood rushing to his cock as he settled deeper into the leather couch.
Kelly brushed her hand down his cheek and neck – Dan shuddered as her nails scraped softly against his skin – to his chest, rubbing his pectorals. The two continued their passionate kissing, and Dan moved a hand to Kelly's hips, leaving it there for a moment or two before tracing up the supple lines of her torso. He hesitated a moment, and cupped one of her jutting breasts in his hand, gently kneading the flesh. Receiving no rebuke, he increased his massaging and, through the fabric of her polo shirt, felt a nipple grow and thicken.
Having spurred Dan into action, Kelly slowly dropped her small hand toward his waist, her manicured nails tracing circles across his stomach as she did. While her tongue shoved into Dan's mouth, she gripped the bottom hem of his shirt and pulled it up, exposing his belt buckle. Gently pulling the belt loose, she deftly released the button of his shorts and pulled the zipper down, spreading the material of his shorts as she went. When Kelly broke their kiss and gave a slight tug at his shorts, Dan lifted his hips from the leather cushion, and she pulled his shorts and boxers to his ankles, where they caught on his shoes. He settled his naked butt back on the cool leather of the cushion.
Her prize now exposed, Kelly lightly ran her nails up and down the shaft of his cock, teasing the swollen glans and sending shivers up Dan's spine as he rested his head on the back of the couch. Closing his eyes, he snaked a hand behind her and slowly but firmly rubbed the small of her back. As his cock continued to expand, Kelly wrapped her fingers firmly around it, stroking it, burying her head at the base of his neck, her full, wet lips kissing him there, causing him to moan deep in his throat. Dan opened his eyes to see Kelly's elegant hand wrapped around his cock, her manicured nails almost but not quite meeting. The diamond from her engagement ring glittered in the warm light cast from the desk. He shuddered at the sight, and his breathing increased almost to a pant.
"My, my," she whispered in his ear. "What's got you so excited?"
"You do," Dan breathed.
"Mmmm…you like my large breasts pressed against you?" she taunted, still in a whisper.
"Mmm-hmm." Kelly suddenly leaned up and buried her hot tongue deep in his mouth, then just as quickly pulled back, her hand stroking his cock all the while. A drop of pre-cum formed at the tip, threatening to break free and run down the shaft.
"My little pink tongue in your mouth?" she continued at his ear.
"Yes," he panted, as her thumb swiped pre-cum from the tip of his cock, lubricating the shaft.
"Doesn't bother you that I'm married? That you're in my husband's house, on his couch?"
"Oh, god, no," Dan nearly grunted out, his thick cock pulsing in Kelly's dainty, little hand.
"Ooh, that excites you, huh?" she said a little louder, feeling the shaft tremble in her fist. "What excites you about it, Dan?"
"That you…shouldn't…be doing…this," he exhaled, his eyes screwed shut again.
"Doing what, Dan?" Her voice was back to a whisper now, and she blew hot breath into Dan's ear, nibbling at the earlobe. "Stroking a stranger's cock? Acting like a slut with my husband gone?"
"Mmmmm," he barely let out. Kelly increased the pace of her stroking; Dan could feel the back of her wedding ring catch on the ridges of his cock, and groaned deep in his throat.
"So you like fucking around with married women, huh?" Dan could only nod as Kelly collected more pre-cum and further lubricated his shaft. "Like having their little hands wrapped around this fat cock, rings staring you in the face?" Dan exhaled deeply, moaning, his hips jerking under Kelly's ministrations as pre-cum flowed liberally now from the shiny tip of his cock. His eyes closed in bliss, Dan couldn't see it, but a smirk of satisfaction formed on Kelly's soft lips. She leaned even closer into Dan's ear, her oversized breasts squishing against his shoulder. Whispering even lower, she said, "We're made for each other, Dan."
Kelly pulled away from him and shifted her trim legs so that both were tucked beneath her. She grabbed the bottom hem of her polo shirt and pulled it up over her chest, revealing the pink sports bra that held her breasts. She tossed the shirt to the floor and reached behind her with both arms. Her breasts jutted forward and up as she undid the hooks behind her, pulling the bra off in one easy motion. Dan's eyes hooded as her firm breasts, capped with thick, light pink nipples, came into view. A soft tan line surrounded them, revealing that Kelly had sunbathed in a bikini often that summer.
Having discarded the bra, Kelly again leaned toward Dan, dragging her breasts against his chest. She lowered her chest toward his waist and pulled the now-hanging globes across his cock. Dan replaced his left hand on the small of her back, venturing lower toward her firm, skirt-covered ass. He felt a thickening nipple scrape across the flesh above the root of his cock before dragging over his twitching shaft. Kelly turned her head, shaking her dirty blond tresses from in front of her face, and looked up at him, her bright eyes sparkling in amusement. "Feel good, Dan?" she asked, somewhat needlessly.
"Oh, god, yes," he almost hissed. "You have amazing breasts." She moved her chest up his, dragging her nipples along the shirt that still covered him. She placed her wet, pink lips at his earlobe, sucking it between her teeth and nibbling lightly. She moved slightly and blew hot breath into his ear.
"They're not breasts, Dan," she whispered, her left hand again finding his thick cock, stroking, pulling, tugging. "They're tits," she said louder, biting hard on the last word. Softer again: "My husband calls them breasts. Everyone else who gets to play with them calls them tits. So call them tits, okay?" she finished, again taking his earlobe between her teeth, the pace of her hand on his shaft increasing. Again, Dan could only nod, but he increased the pressure of the massage he was giving her ass cheeks, slowly pulling her tennis skirt up as he did so.
Kelly's mouth left his ear, and she wasted little time lowering her face to Dan's cock, drawing the head between her full lips. She allowed some saliva to escape from her pretty mouth and dribble down the side of his shaft. She dropped her face further, and a few inches of Dan's cock slipped easily into her hot sucking mouth, Kelly bobbing and twisting her head, her lips locked tightly around the now-slippery shaft.
Dan had by now managed to pull her tennis skirt up and over her hips, exposing her tanned ass, his hand rubbing her sacrum just above her asshole. Kelly slid her legs back, lying flat on her stomach now, as her mouth continued to glide up and down Dan's cock; he could feel her tits compress against his thigh. Her saliva dripped down the shaft, glistening over his neatly trimmed pubis. She felt her wetness lubricating her pussy and rubbed her legs together, hoping to intensify the feeling of bliss she felt between her thighs.
Not obtaining the satisfaction she sought, Kelly rolled her hips slightly toward the back of the couch, exposing her thong-covered pussy to the room's faint light. Dan’s hand remained motionless and stayed where it was, thus traveling along Kelly's ass cheeks and around to the front of her hips as she turned. When his fingers felt the lace of her thong, he ran two of them along the incredibly smooth skin that resides in that crease where a woman's inner thigh meets her pelvis. Lying now on her right side, her lips still clutching at Dan's shaft, Kelly raised her left leg onto the back of the couch, giving him better access to her pussy.
Though his brain was fogged with lust, Dan didn't need to be force-fed instructions. He slipped a finger beneath the edge of Kelly's thong, and then another, the thin fabric stretched over his hand. The two fingers smoothed their way downward along the woman’s outer labia, picking up trace amounts of her wetness as they went. On his way back up, the outer labia eased open, saturating Dan's fingers with her growing mess. At the apex, his fingers slipped over a hard, little bump, and Kelly inhaled a quick breath through her nose. During their journey, those fingers did not encounter a single hair.