The Matrons of Regal Bay Ch. 49

Chapter 49

Gloria's Tales -- Part 4

July 25th was a special day in the lives of Gloria Van Winkle and her two sisters-in-law, Gwen and Greta. On this date in 1965, the three Van Winkle brothers, Hugo, Jonas, and Oskar, arrived in Regal Bay with ideas in mind, and several hundreds of thousands of dollars in the bank, to transform the sleepy bayside village into a thriving city. It took them less than five years to change the entire region, bringing in both jobs and money to the community, and growing the population from less than three thousand to more than thirty by 1970. That number doubled by 1975, when the General Omar Bradley Military Research Facility finally opened, with several government contracts in hand, and several hundred high-paying jobs to go along with it. The opening of a well-funded government facility brought much more than just those jobs, but also drew in all of the peripheral businesses that served the employees and families, and with those jobs came more people and more money into the area. The small college grew into a university. A golf course was designed and laid out, complete with a large club house and recreation center for the use of the research facility's employees and families, as well as the upper class of Regal Bay. And a new, modern hospital was built to serve the entirety of Majestic County. On July 25th, 1975, the county seat was officially moved to Regal Bay, and though the city had been incorporated on June 1st, for the Van Winkles, this date would always be seen as their true anniversary.

Each year since 1965, the Van Winkle brothers would though a party on July 25th, inviting those in the community who had been instrumental in the growth of Regal Bay, and the realization of the Van Winkle's dreams. With the attitude towards sex that they brought over from Germany, the brothers enjoyed and instilled within these very special friends an open view on sexual relations that eventually led these anniversary parties to become orgies. In time, this attitude began to seep into the lives of the population of Regal Bay, to the point where some viewed the city as the most sexually liberated in all of the Americas.

In time, these anniversary parties began to grow less and less of an extravaganza and more intimate, until only the three brothers and their wives, and a select few, gathered for dinner, drinks, and enjoyment of the flesh. By the time Hugo, the oldest and true Patriarch of the clan, had passed away in 1990 at the age of 60, the gatherings had been family only. Gloria, Hugo's second wife and mother to his five children, had only been 41 at the time of his death, and yet took up the reigns of the family empire easily. She was a born organizer and within months had all of Hugo's responsibilities delegated to others, be they family or not. As a result, she was able to settle into the role of C.E.O. easily enough.

Through the years, as their children matured, the second generation of Van Winkles began to attend the anniversary parties. With incest such a taboo across the country, these gatherings were closed to any outsiders. Within the family, the act had been commonplace for centuries, and as each maturing generation, those inclined were included, and those not so inclined were never forced, but neither did they attend the orgies. Traditionally, after dinner and drinks, those not wishing to engage for one reason or another, would leave. Nothing derogatory or disparaging was ever said, and the family remained close.

By the time Jonas had passed away, the last of the three brothers, the women had already taken the helm across the family, both in business as well as in pleasure. The anniversary party of 2011, just months after Jonas' passing, was a somber one, and the only not to end on a sexual note. Since then, however, the three Van Winkle "Sisters" ensured that the party went on as originally planned.

For this year, Gwen would be hosting at her in-town home. Her husband, Oskar, had purchased one of the large, original homes of Regal Bay, one which overlooked the marina, and had renovated it. It had become a landmark and inspiration to those in the immediate neighborhood, and now stood proudly among the stately old buildings owned and occupied by many of Regal Bay's hierarchy. Although Gwen herself was widowed, she maintained the large home with the help of her two sons, who still lived with her. Neither, however, would be joining in that year, as they were away. In fact, with much of the family on vacation, out of town, or busy with other family members, that year's anniversary party would only include Gwen, Gloria, and Greta. That wasn't to say that the three women wouldn't be enjoying themselves.

Gloria had cleared her calendar for that afternoon and arrived at Gwen's home before six in the evening. Gwen had invited her over early, as they usually didn't get together until sometime later. In fact, the plans that year called for dinner down town at Theros before retiring to Gwen's for drinks. After, they would let nature take its course, as it were. All three women had long ago become lovers, and didn't necessarily need the presence of male companionship to enjoy themselves sexually.

Instead of driving into town and having to park either on the street, Gloria had her grand-daughter Danielle give her a ride. Danni had just recently been licensed and was more than willing to drive her grand-mother around town. Gloria gave the teenager plenty to do, letting Danni take her to the grocery, or the mall, or even just a ride through the mountains and valleys of Majestic County. Danni had yet to join in with any of the family's activities in a sexual manner, as far as Gloria knew, though the buxom, beautiful blonde eighteen-year-old was desirable enough. Her father, Gloria's only son Glenn, had his own perversions and desires, and it wasn't at all clear to the family matriarch if her son enjoyed spending intimate time with his family.

"Thank you, again, Sweetie!" Gloria waved to her grand-daughter as Danni pulled her hand-me-down Cavalier away from the curb. The walk up to the front porch of Gwen's house was short, passing through manicured shrubs that lined the walkway. The sweet smell of fresh-cut grass filled her nose as she ascended the six steps up to the old wooden porch. She needed knock or ring the bell, and Gloria passed on into the big house. Inside the foyer, she removed her linen overcoat and hung it on the empty rack. Beneath it she had only wore her plum-colored corset, which served to give shape to her torso as well as cradle her ample breasts well, the cups curving below her large areola and leaving her nipples out on full display. She also wore matching plum panties in a French-cut, and black garters and stockings. She gave herself a once over appraisal in the full-length mirror that Gwen had installed long ago in the foyer, and liked what she saw. Her long, black hair hung straight down her back nearly to the curve of her ass, which was once again tight given the five miles she'd put in on the tread mill that morning.

Stepping across the foyer's hardwood floor, her heels clicked, echoing. She paused at the entry to the front room and saw that her hostess for the evening had already begun to enjoy herself.

"It would seem that I am not only early to the party, but tardy as well," Gloria laughed as she joined her younger sister-in-law in the front parlor room. Decorated in a turn of the century European style that Gwen's late husband had favored, the cozy parlor held two sofas; one wide enough for four while the other would comfortably seat three. These were flanked by high-backed wing chairs, with small side tables between. The only electronic device was an elaborately decorated stereo, done up to resemble an early 20's radio, though it also played CDs. Gwen had Mozart playing as background music as she entertained the two young gentlemen seated side-by-side on the wider of the sofas.

Gwen, her artificially-maintained blonde hair now cut short, in something of a bob, lifted her head from the lap of the nearer of the two naked young men and smiled. "I'm sorry, but I really couldn't wait for you. These fine young men had finished up early and after I'd served them up some lemonade, I really had no other ideas about how to keep them entertained until you arrived." Gwen's bright green eyes, sparkling behind her modern glasses, displayed a playfulness her Wisconsin accent highlighted, and yet Gloria was all too familiar with Gwen's sinfulness. Given the chance, the younger Van Winkle widow would have already drained each of the young men's balls and cast them away, as she had to so many other fine young men through the years. Gwen Van Winkle, as her friends were well aware, was a blatant cum-junky and never passed up an opportunity to suck the life out of a male member. Gloria had arrived just in time to find her on her knees with one lengthy cock between her lips and another on stand-by in her left hand. Gloria noted that Gwen was dressed very similar to herself, in a corset, garters, and stockings, though she had chosen an outfit in the rose family. She also had forgone wearing underwear, Gloria noticed.

"Are you planning on introducing me?" Gloria asked.

Gwen sighed and settled back onto her haunches, though she maintained her grip on each hard cock. "This is Landon Stevens," she said, indicating the young man whom she had previously been pleasuring with her mouth, "and his younger brother, Michael."

"Hello," Michael nodded in greeting. Michael looked as if he were about to run with Gloria's arrival. His cock had begun to soften in Gwen's hand despite her continued stroking. This was all very new to him, she recognized.

"Hello, young man," Gloria smiled warmly for him as she moved close to present her hand to him. He shook it awkwardly. "I see you're enjoying Gwen specialty," she commented.

"I had to restrain myself," Gwen laughed. "Michael tells me that he'd never had his manhood pleasured in such a way before, even by a girl his own age."

"Mike hasn't been out with too many girls," Landon said, giving his younger brother a jab in the shoulder as he did. "He's shy that way."

"Interesting that we find you here, then," Gloria commented as she stood before the younger man. His eyes were taking her in quite noticeably, and his erection began to fill out once again. He was anticipating further pleasures, no doubt. Gloria wasn't going to disappoint him.

Gwen moved over to be fully between Landon's parted knees and Gloria settled on the thickly carpeted floor between Michael's. "You don't have any issues with having your beautiful cock enjoyed by an old woman, do you, Michael? A woman who could be as old as your own grand-mother?"

In response, Michael shook his head. "No, Ma'am."

"Well, then," Gloria smiled and reached out to replace Gwen's hand with her own. His cock was warm in her grip and very rigid. It also throbbed, warning her of his hair-trigger. With her other hand, she reached up and took his scrotum in hand and began to gently roll his balls. "I'll take very good care of you."

Beside them, Gwen had resumed her oral feast upon Landon's stiff cock, taking him to the root before backing off to enjoy working his knob with her tongue and lips. Gwen had been pleasuring the male organ for nearly all her life, having been taught by a lecherous pastor back home in Oshkosh. Gwen had enjoyed the taste, texture, and thrill of having a man's cock in her mouth from the beginning, and had never once failed to bring about an overflowing release that went down her throat to warm her belly, unless she was in a mood to be screwed. She often bragged that for every time her vagina had been penetrated, she'd had three cocks fill her mouth. Gloria could believe it. She'd known the younger woman for more than forty years.

Gwen Van Winkle, for all of her being a 63 year-old grand-mother, was still as hot and horny as they came. At times, Gloria found it difficult to keep up with her younger sister-in-law. Gwen had returned to slurping upon Landon's cock, and Gloria gave the blonde-haired young man a once-over appraisal. He looked no older than Gabriel or Paul, her mid-twenties grand-sons, probably 24 or 25. She turned her attention to Michael and could see that he was somewhat younger, maybe not even twenty. He was darker haired than his brother, and slighter in build. Both young men looked rugged, with slightly longer hair than was the current style, as well as wearing scraggy-looking facial hair that was in style with their generation. Both looked as if they spent many hours outdoors, probably working under the sun rather than relaxing.

"You've found a nice set to enjoy this afternoon, Gwen," Gloria said, giving Michael a grin and wink as she tugged his cock gently.

Gwen pulled off of the blonde one's cock long enough to say, "I was just getting them warmed up for your hot pussy, dear," and then plunged her mouth back down the boy's full length in a single gulp that drew a gasp from his lips, as well as an "Oh, fuck!"

With her fingers wrapped around Michael's cock, she introduced herself. "I'm Gloria, by the way." She then gave his knob a long lick, swirling around the tip and tasting a bit of his salty pre-cum.

"I'm Michael," he replied in a shivering voice.

"You've got a nice cock here, Michael," Gloria complimented. "How old are you?" She gave his knob a quick lick as he replied.

"I'm 20, Ma'am," he replied. As young as her youngest grand-son, Gavin. She even wondered if Gavin would know Michael.

"Please, don't call me "Ma'am"," Gloria insisted. "Otherwise I'm not going to suck this big, beautiful slab of meat you brought along." She squeezing his shaft harshly and twisted, making Michael groan before saying, "Yes, ma'am! I won't call you ma'am."

"You'd better not," she finished, before dropping her own wet mouth down his full length, taking his cock into her throat smoothly. It was a talent Gloria had picked up over the years, taught to her by her late husband, and made good use of often. It drove her lovers wild, and Michael was no exception, grunting and gasping as her head pulled up and slammed down time and again in that first delicious minute of contact.

Gloria slowed her oral workout of Michael's cock as soon as she could taste his pre-cum leaking into her throat. She then pulled back and began to only run her mouth up and down the first two or three inches of cock-flesh. Michael's hand went to the back of her head. She'd just that afternoon had her hair done, having a fresh coat of jet-black dye added. She'd been showing more gray in her hair than she liked and with an evening of debauchery planned, Gloria wanted to provide a younger look. Not that it mattered to any man, regardless of age, what a woman's hair color or style was, not when they were getting head. Gloria gave Gwen a glance, noting that her short blonde hair was indeed graying to almost pure white, and it mattered not a bit to the blonde-haired guy she was sucking on.

For a good ten to fifteen minutes the two women paced each other, sucking upon the young men's cocks. Balls were fondled and squeezed, and when the need for a good deep breath over came one or the other, those heavy, cum-filled balls were licked. However, Gloria hadn't come over to her friend's house to suck some young stud off. She'd come over to get herself fucked, and that was what she was going to do.

Gloria let Michael's saliva-coated member fall free of her lips and pushed her plum panties to the floor. She stepped out of them and quickly moved to straddle him. She turned her back to Michael and reached between her thighs to take hold of his thick dick. Michael's hands went to her hips as she positioned herself and began to slide his wet knob along her equally dripping slit. Once her hole was aligned, Gloria dropped onto his post. She moaned loudly as his cock filled her, gasping a long, "Yeessss!" as her body welcomed the invader inside. Behind her, Michael echoed her groans as Gloria began to rise and fall upon his lap, fucking her upon his fuck-stick.

Beside the engaged duo, as Gloria found a steady, vagina-pleasing rhythm upon Michael's young rod, Gwen had pulled Landon from the sofa and onto the floor. "Lay down here and show this old hag how good that wicked tongue of yours feels!" Gwen cackled even as she rushed into position above his grinning up-turned face. Gwen straddled his head and lowered her hips until she had begun to feel his rapid breathing on her blonde-furred pussy. She began stroking his tanned chest and tight belly. "Don't wait for me! Get to work, Landon! You've got another bush to trim!" she laughed. Landon didn't hesitate, either. He'd been in this position many times over the last few years, usually after doing the needed yard work for the old Van Winkle widow. As he took hold of her wide hips and dug into her fleshy orbs, he sucked in the thick labia that hung obscenely from between Gwen's thighs.

"Oooohhh, that's my boy! Eat that fat pussy!" Gwen loudly demanded as she settled across his torso. She allowed her large tits to flow around Landon's belly as her lips engulfed his manhood once again. She was several inches shorter than her lover and Landon had to follow her pussy as she moved against his body. He had his head propped on one arm while tickling her asshole with a finger from his free hand as he devoured her aged cunt.

After a few deep gulps of Landon's cock, Gwen huffed, "Eat that fat pussy, Landon! You know you like old, fat pussy. Now eat me out, you fuck! Just like that! Just like your mamma does!" And Landon did as he was told, like any good young man should. Gloria probably should have been surprised by Gwen's demands. After all, Gloria had eaten out Gwen's "old, fat pussy" on several occasions, and probably would again that night after it was filled to overflowing with hot creamy boy-cum.

Gloria's tits, now released from the top of her corset by Michael's hands, bounced upon her chest as she rode his cock towards her initial peak of the evening. Her pussy was trembling as she reached down and attacked her thick clit with a finger to drive herself onward and upward. It had been a few days since she'd cum with a hard cock inside her and she needed it. Gloria let herself ride the crest and began to gasp as her orgasm broke. She threw her head back, moaning a long, "Oooohhh, fffuuuuccckkk!" as her cunt spasmed around Michael's still pumping dick. He held her hips high as he fucked up into her climaxing pussy. Her juices squirted out with every thrust and coated his shaft and balls. Gloria purred like a happy kitten as she slipped down the back-side of her climax.

"Oh, you really must fuck me, my young stud," Gloria whispered over her shoulder as she settled upon Michael's cock fully. It was throbbing deep inside her, but she didn't think he'd cum yet.

"Hell, yeah!" was his reply. Gloria eased off of his lap and swapped places with Michael. Michael stood fully a full head taller than her, and she wasn't short by any measure. Michael reminded her of Hugo, just briefly, and only in the look on his face as he anticipated the next act of their evening's play. She knew it hadn't been chance, not knowing Gwen as she did. Michael had been chosen for her enjoyment that afternoon simply because he was very much like Hugo had once been, when Gloria first met him. Though Hugo had been nearly forty at that time, he had always carried himself much younger. Michael and Hugo shared the same facial features, and in the back of her mind, Gloria didn't wonder if it wasn't just a coincidence. Hugo had enjoyed many women about Regal Bay in his years, and the mother of Michael and Landon may very well have been one. Maybe Gwen knew something that Gloria should know, and Gloria vowed to ask her younger sister-in-law after. In the mean time, Gloria was determined to enjoy this fine young stud that now stood before her with a thick, pulsing, drooling cock in hand, and aimed directly at her sexual center.