Xmas Party- Dolly and Jack Part 1
Jack Logan checked himself in the mirror one last time before heading out to the firm’s Christmas party. He insisted on tying his own bowties instead of wearing a pre-tied model whenever he wore a tuxedo, and he’d had a tricky time trying to get it right this evening. It wasn’t perfect, he decided, but that was part of the charm of a “real” bowtie—that it wasn’t perfect. Or so he told himself. Jack actually liked black tie events, but was not especially looking forward to this evening’s party, because his wife Allison was out of town at her grandmother’s 80th birthday celebration. Jack expressed his regrets that he couldn’t go to the family birthday celebration, but maintained that the office party was a requirement. The senior partner, Arnie LaBreque, was an odd sort. He didn’t really like most of his junior partners or associates, but demanded that they all attend the stuffy party he hosted at his house each December. And Jack would be without Allison, feel awkward explaining where she was, and have no one to stand with or sit with. Great! An entire evening being a third or fifth wheel!
Jack had one thing going for him tonight, though—he happened to live around the corner from the senior partner, so he could walk to the party and get back home without worrying about drinking and driving. Jack had gotten the opportunity to interview with the firm, in part, through connections from living where he did. Jack had the lowest priced house in the subdivision, but he was in the right subdivision. Though it was a fairly warm night, Jack nevertheless wore his black topcoat to complete the formal look. He sipped a vodka in a plastic cup on the way over, knowing, as neighbors do, where the trash can could be found to deposit the cup before reaching the door. He also had one other reason to look forward to the party—Dolly LaBreque, former Miss Georgia and University of Georgia cheerleader, the boss’ trophy second wife, would undoubtedly be dressed to kill. Jack was pretty sure that if he bothered to look up cougar in the dictionary, after the definition of the animal, when they got to the slang about mature, hot, sexy women, he’d find Dolly’s photo. Probably, there was a duplicate listing under MILF as well. She was roughly in her late 30s. Jack wasn’t sure when she’d been a college cheerleader, and he knew her pageant days were a while ago, but damn, she was still hotter than most 20-somethings. Yes, he’d fantasized he was fucking her during sex with his wife and when jacking off, as well.
When Arnie and Dolly opened the door, Arnie extended his 70-ish hand for a perfunctory handshake and mumbled, “Merry Christmas, Rick,” at which point Jack saw Dolly flinch in response to Arnie getting his name wrong, as she then took his hand in both of hers to say, “Yes, Merry Christmas, please come in.” As she moved Jack past her, away from Arnie, she leaned in and whispered, “I’m so sorry about Arnie and your name, Jack,” as the tip of her nose brushed his ear. “Let me take your coat,” which was handed to a coat attendant, one of the workers hired for the party. “No Allison?” Dolly asked, and Jack felt the warmth of his drink and the warmth of Dolly’s hand on his wrist, smiling in appreciation of the boss’ wife getting his name right and his wife’s as well. “Out of town, again, I’m afraid. This time, it’s for a family event, her grandmother’s 80th birthday. I did let Arnie’s secretary know in advance, for headcount purposes. I hope there wasn’t any mistake on the list.” Dolly rolled her eyes. “Don’t worry, Arnie didn’t hire Steffi for her administrative skills.” Dolly’s eyes locked on Jack’s in a knowing way. “I’ll check on you later. I need to pay special attention to such a distinguished guest who’s also a neighbor,” as she reached up and actually adjusted his bowtie slightly. Her slender, elegant, French manicured fingers were garnished with a four-carat diamond in a platinum setting, accented with emeralds that captured her blue eyes. Dolly winked and gave Jack a hostess-appropriate kiss on the cheek before turning back toward the door to resume her hostess duties. Jack felt in a slight daze as he made his way to the bar, in search of more vodka, and exchanging holiday greetings with colleagues along the way. Wow, he thought, I’m definitely going to fantasize about her tonight when I get home after putting in time at the party.
Dolly was always a knockout, the perfect hostess, and good with names, but never before so friendly or warm. She was really the stuff of fantasies, and Jack suspected that, at some point or another, every man and woman in the firm had wondered what such a smoking sexy younger woman was doing married to a man old enough to be her father, or maybe grandfather. The men, and probably half the women, wondered if she was as good in bed as they fantasized she was. Dolly was the daughter of one of Arnie’s oldest clients, the founder and chairman of the board of a local retailing firm that had grown wildly into one of the 30 companies in the Dow Jones index. That growth had fueled much of the firm’s growth as counsel. After the Miss USA pageant at the conclusion of her junior year in college, when she was a semi-finalist, she married her college sweetheart, J.T. Johnston, a football player at Georgia and who was drafted by the NFL’s Miami Dolphins shortly after the couple’s honeymoon. Dolly divorced him in his second season after her football-playing handsome husband was pulled over for DUI on South Beach with a lovely dark-haired Latina in his car and the Latina’s thong panties in his hand. Later that night, her husband discovered that his lady friend was only 17, so, while not statutory rape, he was contributing to the delinquency of a minor by buying her drinks. No one could ever prove who had given her the cocaine that was present in her urine. The signing bonus was marital property, and, in the divorce settlement, Dolly was compensated well for the embarrassment. J.T. was cut by the Dolphins shortly afterward and never lived down the incident, nor the question, “Why were you fucking around with that high school aged slut when you had a beauty queen at home?”
A brief period of promiscuity after the divorce gave Dolly a temporary feeling of relief from the entire ordeal, not to mention the chance to really experiment sexually in a way that J.T. never provided. J.T. was a handsome, well-built guy with lots of stamina, but was sort of a meat-and-potatoes, three- or four-position lover. Not until after her divorce did Dolly realize that there was an entire sexual galaxy she might never have discovered if J.T. hadn’t ruined everything. So, maybe he really hadn’t ruined everything, she sometimes thought.
While trying to stay out of the paparazzi spotlight and Miami Herald South Beach scandal columns, Dolly decided to put her Bachelors of Business Administration to use, so she accompanied her father to some board of directors meetings. As much as she tried to avoid appearing slutty, she found that business was no substitute for the rush of hot, illicit, unbridled—and unsanctioned—sex. So she learned to be very careful to avoid attention as she devoured the best men (and, for the first time, some very hot women, too) that she found as willing lovers. But her increasing exposure to the corporation her father founded and some of the corporation’s key business partners proved to be an excellent means of focusing on something other than an early and publicly failed marriage and fairy tale gone very wrong.
Not that Dolly had been unhappy revisiting slutdom for the first time since college. Now, despite having thrown so many previously unexplored taboos or cautions to the wind (Three-ways! Interracial! Anal! Swallowing! Older Men!), she was still the same person who had been raised with traditional values, new sexual frontiers to be conquered notwithstanding, and eventually felt that she should do the socially responsible thing and get settled again. Since Dolly had been discreet about her sexual activities, her reputation was intact. Yes, she wanted to get back on the mature path she’d thought she’d started with J.T. when she’d gotten married. She decided that her next husband would be older, stable, and secure—someone who would feel lucky to be with her, not some hot shot who didn’t appreciate her. Enter Arnie LaBreque, recently divorced from his overly critical first wife, nicknamed “the bride of doom.” Arnie had married the bride of doom for her money and social standing and tried for as long as he could to ignore her insufferable, demanding, critical manner. Arnie’s career took off as her family’s network provided him the right introductions to grow his law firm, and then, when Dolly’s father grew to be a career-expanding big-ticket client, eventually Arnie realized he could easily afford an ex-wife. Arnie met Dolly at a board of director’s meeting in Vail, admired her in her tight fitting ski outfit, and, at that point in time, approaching age 60, retained enough manners and style to remind Dolly of her dear father and appear stable. He also reminded her of the eager, handsome fathers of a couple of her Kappa sorority sisters whom she’d fucked early on during college, before she got serious with J.T. Something to be said for mature men who knew how to make a woman cum.
So, although Dolly was in her late 20s, she accepted Arnie’s invitation to stay an extra evening, ski, and then join him for après ski followed by dinner the night after most of the other directors flew home from Vail. Dolly’s father gave a nod of approval before getting on his Gulfstream to return to Atlanta. When it was just Dolly and Arnie by candlelight, well, if not love at first sight for her, it seemed safe. And new and exciting. She didn’t sleep with him in Colorado, just some drinks in a Jacuzzi and some passionate kissing after dinner. Okay, he did have a great villa. And looked like the kind of rich, handsome guy who is always showing up in social column photos in a tux with a gorgeous, younger blonde on his arm. Dolly could see herself as that blonde. Two weeks later, he took her to Sea Island, rented her a cabin of her own to prove he was a gentleman, and she proceeded to seduce him in his beach house. It was okay sex, not more, not less. He was average, acceptable, nothing flashy, but she did have an orgasm, so Arnie passed the test. They were married a year later, after a mostly faithful year in which she satisfied her need for heat with the occasional fuck buddy and even some experimental bi activity. She wondered if she’d be able to adapt to faithful monogamy. She didn’t.
Back at the Christmas party, Jack looked back toward Dolly as he sipped his Gray Goose and surveyed the party. Dolly was in a black strapless dress, black hose, and 5-inch black pumps. She had two children with Arnie, giving him six children in all, the oldest of whom, his first daughter with the bride of doom, nicknamed “the princess of doom,” was three years older than Dolly, and had, in fact, been a senior in Dolly’s sorority the year Dolly pledged. Dolly was stunning with her long, thick, blonde hair, in which she wore an elegant diamond holiday pin this evening. She wore a double strand of pearls, and her bare shoulders and toned back and arms reflected the persistent fitness regimen that made her a well-known knockout in the community. She was decidedly feminine, yet athletic and toned. Women feared her, since she seemed to have it all—looks, manners, fitness, money. Was there a portrait of her in the attic, decaying? Men from about age 18 to 88 wanted to fuck her. At least those in good enough shape not to worry that this powerhouse might fuck them in half wanted to fuck her.
And since Arnie had proven unfaithful, first with previous secretaries, then with one of his law firm’s associates, and for the past half-dozen years with Steffi, the unskilled in business assistant whose sole skill appeared to be subjugating herself to men for personal gain while serving as that man’s executive assistant, Dolly had decided to enjoy certain liberties with men whom she considered “safe” for sexual release purposes as her own form of retaliation. Dolly was independently wealthy, far more than Arnie, as a result of her shares in the company her father founded. Heck, the few million she’d gotten from J.T. the football player at the time of her divorce was mere pocket money. Arnie was careless enough to make Dolly curious, and careless enough for the P.I. Dolly hired to catch him and video record him, so Dolly didn’t have much to fear. Why had she stayed married this time? Inertia. She felt safest fucking married guys who didn’t want to lose their marriages and knew they were just a rent-a-cock to her. And there was no shortage of such fun, since Arnie was not paying attention, having become so impressed with his success that he thought he could do no wrong. Arnie’s conduct was suspected by only a few, so there was no humiliation for Dolly in staying with him. She had two children, who were still important to Arnie even if he wasn’t around all that much, so Dolly did her best and kept the family together. The kids loved Arnie, and why not—they wanted for nothing and he never hassled them. They had no idea what was going on, or wasn’t going on, between their parents, and Dolly was determined to keep it that way.
But Dolly was getting hungrier in her lust. And now tonight, here at Arnie’s firm Christmas party, right in the home she shared with Arnie, handsome attorney Jack Logan was unattended. Dolly turned and looked for Jack over her shoulder, smiling at him when she found him trapped in the corner, listening to tax attorney Rick Walton’s obese wife talk about her horses. Poor horses, having to lug that fat bitch around, most everyone thought whenever Cindy Walton talked about going riding.
Jack was wondering how much longer he could keep the smile on his face as this 5-foot nothing, 200-pound woman talked about standard bred horses to him. He’d somehow gotten cornered, and two large indoor plants blocked his most likely escape route. Suddenly, he felt smooth fingers slide into his right hand as he gripped his drink in his left, and, when he turned, he saw Dolly wink as she then leaned in toward Cindy, “Cynthia, darling, thank you so much for keeping our Jack company. The poor boy’s wife is tending to family out of state tonight, and he’s all alone. Won’t you and Rick allow me to borrow him long enough so I can feel like a good hostess and find him a dining partner?” Before Cindy could even agree, Dolly interlocked her fingers with Jack’s and led him away, brushing past big Cindy and into the kitchen, the closest getaway out of sight from the slighted equestrienne.
“Just in time, Dolly,” she thought to herself. She’d always gotten a little bit moist when she’d catch Jack eye-balling her. He was young, fit, handsome, married. What’s not to like about having him check her out, she’d always figured. If Dolly was going to fuck someone from Arnie’s firm, Jack would be a good candidate. Since he was married, he wouldn’t get too attached, and, since he was subordinate to Arnie, well, the possibilities were delicious and naughty. And more than once, it seemed, Jack’s pretty wife had some family thing to attend to out of state, leaving Jack to fly solo at firm functions. Seeing the RSVP list last week, Dolly had noticed that Jack was again sans date. “Come into my web,” said the beautiful spider to the yummy fly. A fly who she knew had eyes for the spider. And a fine acting job she’d done, pretending to be surprised or disappointed that Allison was out of town. Far from it. Mostly she was feeling ... a little bit moist.
Jack was barely aware of the hard-on he’d gotten from holding hands with Dolly, but his thick 8-inch cock created a tent that was noticeable to his sexy hostess. She liked that. She wondered if he was faithful to Allison, a sweet debutante in her own right. “That looked awful, Jack. You just looked as if you needed saving,” Dolly laughed. Jack allowed his eyes to go from Dolly’s eyes to her elegant neck and pearls, to her tanned cleavage, enough to be sexy, but not so much as to be slutty. Well, hopefully not enough to be slutty, she thought, as she followed his eyes. Her breasts were 36D, and, yes, she’d allowed herself a slight tune-up and lift a couple years back after her second child. Truth be told, the doctor really was only restoring what she’d looked like naturally about a decade earlier. And he hadn’t had that much lifting to do. The surgeon had bragged to her that she was so sexy that she didn’t need to have a thing done to her (which was true), but that he was so good he could nevertheless make a noticeable improvement if she cared to allow him. He’d done this bragging in bed with Dolly, having invited her up to his hotel room following a downtown fundraiser after his wife went home early when the babysitter called that their child had a fever. “You stay. If she’s better in the morning, I’ll come on back down and meet you for brunch and hotel sex,” his wife had said. As it turned out, the little girl would be sick for two more days, and Dr. Cumalot never did get brunch. Dolly provided him with wonderful hotel sex, however, and they fucked on two additional occasions when Arnie was out of town before she took him up on his plastic surgery suggestion. Then after she’d healed, she fucked him a few more times until the good Doctor felt guilty enough to break off the affair. Dolly was gracious, as she always was on such endings. And why not, he’d done great work, and between that, running, and Pilates, she truly did look like a hard-bodied 20-something gym bunny as she stood in the kitchen with 32-year old Jack. Jack was enjoying the view … and Dolly liked the look of his hard-on.
Impulsively, Dolly stepped close to Jack, allowing her firm waist to press into his erection as she kissed him, hard and fast on the lips, feeling somewhat bold to do so in the house. Jack responded and brushed his fingers on her toned, black stockinged thigh, and slid them up the slit of her dress far enough to discover she was wearing thigh highs. Their eyes met, and Dolly hurriedly asked, “Pool house sound good to you?” Jack nodded yes, and she said, “Ten minutes. Go out the side door downstairs and walk along the fence to the back of the pool house. You won’t pass through the outside lights that way.” Another quick peck on his lips and she was gone.
What just happened? Was he going to fuck the senior partner’s sexy trophy wife? Or more accurately, judging from who was the aggressor, was she looking to fuck him? Either way, conflicting thoughts filled Jack’s head. But only engorged blood and lust filled the little head, and Jack hadn’t been getting much at home lately, maybe for longer than that. Plus, he had been fantasizing about Dolly so long that he wasn’t going to say, “No thank you,” to his fantasy come true. He was going to fuck Dolly LaBreque!!
A quick visit to the powder room allowed him to adjust his cock so that it wasn’t pointing straight ahead, and then he subtly moved to the back stairs, went down a level and through a side door of the downstairs game room. He made his way along the outdoor shadows to the poolhouse and stepped through the French door around the backside, away from the house. The lights were off, but lights from the house and property sent enough radiance through some transom windows facing the house that he could see. There was an open room for socializing and enjoying drinks or snacks, with a bar and mini-fridge along with a microwave. A pair of private bathrooms with showers in each and two guest bedrooms, sparsely furnished, seemingly designed for a family member who needed a nap during a pool party …. But beds were not just for napping, and Jack heard the door click shut (he hadn’t heard it open) and a few click clacks of heels on the Spanish tile floor until those stopped. As he turned, he saw Dolly remove her second shoe, adding it to the one she’d just removed and dangled from her sexy fingers. She set her shoes down next to a futon, walked straight to Jack, and proceeded to kiss him while pushing his tuxedo jacket back off his shoulders, starting to undress him. Her tongue pushed against his lips for only a second before he realized that the game was on. He greedily opened his mouth and welcomed her tongue into it, as he reached behind her to fumble with the zipper on her dress. “I’ll get that,” she whispered, breaking their first true kiss, then she licked her lips and kissed him again, this time being happily surprised by the way the younger man’s tongue invaded her married mouth. He was a good kisser—that was easy to determine right off the bat. Hope he’s as good with his cock, she thought. “You’ve got more buttons. Let’s get you naked first, Baby,” she hissed as she continued undressing him and resumed kissing. He liked that she called him “Baby” and his cock twitched as he heard it. He stepped out of his shoes, worked his cufflinks, and unbuttoned his shirt from the bottom up. When she reached his collar, she lifted up on her tip-toes and grabbed one end of his bow tie with her teeth and pulled, untying it. Then, soon enough, his clothes, save for his boxers, were draped over a chair. His cock was at full mast, poking through the open fly of the boxers. “I want that,” she teased him, nodding in the direction of his cock as she reached behind her back, unzipped her dress, then carefully laid it down along the length of the futon. A black lace demi-bra followed. Then Jack stepped forward and slipped his thumbs inside the hips of the black satin v-string thong that covered her already wet and wanton married pussy. She took his face in her hands and kissed him again, deeply, passionately, sensually, their tongues wrestling, then dancing, then finding each other’s rhythm, moving together in massaging and mingling motions, the introductions having passed and now having advanced to the next level of lovers working together. As the tongues go, the bodies follow ….
“Dolly, you’re so sexy. Did you know I’ve fantasized about this since the first time I saw you?” Jack mumbled into her mouth between kisses and breaths. “MMMMmmm, really?” she purred back, not caring if he knew she was toying with him by using that tone. Jack hadn’t been all THAT subtle in checking her out every chance he got. Damn right, she knew this man wanted to fuck her. “So you have an old lady fantasy, do you?” she tossed out there, giving him the opening to tell her about his lust. Sure, it was cheesy of her to say. She knew perfectly well she was no old lady, just that she was older than him, but hey, what broad in her late 30s doesn’t love hearing an in-shape young 30s guy with a thick 8-inch hard-on tell her how much he wants to fuck her. “Old? Holy shit, Dolly. You’re hot, you’re a beauty queen. Hell, you’re hotter than women, well, um, shit Dolly, you’re well … shit, college girls would die to have your body,” Jack replied. His hands found their way up to her firm breasts and erect nipples, her smooth skin feeling warm and silky, as his hands moved north from her thong along her toned torso. “Well, thank you, Baby. That’s so sweet of you. The least I can do is not make YOU die to have my body. You do want my body, don’t you, Baby?” she inquired before matching her mouth deeply with his once again. He could wait to answer, as he was too busy getting lost in her kiss. She was becoming more and more aroused by the young attorney’s surrender and response to her high-risk seduction. She broke the kiss again, “Well, you didn’t answer. Don’t make me beg you to fuck me, Baby” He felt his cock twitch and strain to try to get even harder.
Jack liked her dirty talk, and Dolly could tell. She smiled a wicked smile, slid her manicured left hand down his chest to the elastic of his boxers, and slid them down his body, avoiding the satisfaction for him of any contact with his desperate cock. He watched, loving the image of her diamond engagement ring and, together with diamond wedding and anniversary bands given to her by his boss, now on his body, seeking to cuckold his boss at the boss’ own Christmas party, at the boss’ own house. Not just the boss’ wife, but a Miss Georgia, a Miss USA semifinalist. Perfect body, perfect everything. Hel-lo, mother lode!
Dolly firmly wrapped her slender fingers around Jack’s cock, led him by that tool to the first bedroom, and then pushed Jack down to a sitting position on the edge of the bed. She stepped inside his legs and brought his hands up to her thong, assisting him in starting to remove it, then putting her hands on his shoulders while he finished removing the thong over her stockings. Now just in her thigh highs, she told him, as she leaned forward to bring her breasts to his mouth, “These are too much of a pain to put on and take off in a hurry, Baby. Maybe I’ll remember to be bare-legged for you the next time we fuck. You don’t mind fucking me hard while I’m wearing these black thigh-highs, now do you?” He broke his lips away from her hard, sensitive nipple long enough to say, “Mind?” before she guided his mouth back to her breast, explaining, “It was a rhetorical question, Jack. I’m insisting you fuck me. There’s no choice in the matter. Hard, fast, deep. Before we’re missed, fuck me, Jack. Fuck your boss’s slutty wife” “Yes, ma’am,” he thought.
To be continued....
Purely fictional fantasy for your reading pleasure!