The Matrons of Regal Bay Ch. 01

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Gloria's Tales Pt. 01: Matriarch of Regal Bay relaxes with her young lover.
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Part 1 of the 74 part series

Updated 06/08/2023
Created 02/13/2017
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SteinWolf8
SteinWolf8
469 Followers

The Matrons of Regal Bay

Gloria's Tales

Chapter 1

"Ladies and gentlemen, I thank you for coming and look forward to a wonderful weekend here at the club." Gloria Van Winkle gave the group before her a round of applause, little more than a golf clap really, and smiled to those seated along the sides of the long conference table. The members of the Regal Bay Golf Club and Convention Center board of directors and department heads, men and women whose jobs it was to run the thriving facility with the expected care and attention to detail that Gloria demanded, nodded to their statuesque director as they gathered up their papers, folders, and lap-tops. The group numbered thirteen, with Gloria included, and met promptly every Wednesday afternoon at 1pm to go over the upcoming schedule. As Gloria looked at each in turn, she realized once again that she had seen very nearly every one of them naked at one time or another, and had been intimate with more than half of them as well. That thought always brought a grin to her tanned features, and a tingle to her loins.

Gloria consistently put long hours in at the Convention Center, attending meetings and seeing to every little detail of every social and private event on the schedule, each and every weekend. Gloria was a workaholic, even at her advanced age of 67, and had a very busy social schedule for much of the week. She was one of the leading citizens of Regal Bay; her late husband and his brothers having been instrumental in the rapid growth the area underwent through the sixties and seventies. Hugo Van Winkle had been a stallion of a man, and his sexual prowess was folklore. Gloria had been his second wife, nearly twenty years his junior at the time they had married. Rumor has it that he'd fucked his first wife into the grave.

Gloria had grown up in Sacramento, the child of Howard and Grace Reno. She had a twin sister, Maria, though to look at them there wasn't any resemblance at all. Where Maria had taken their mother's pale Irish beauty, their father Howard had been full-blooded Choctaw, and Gloria retained the classic look of a Native American woman. Her flesh tone was that of caramel, and her dark brown eyes and long, straight hair gave her an exceptional beauty. She had always been a tall, slender woman and moved with sure grace everywhere she went. After Hugo's death, when Gloria had only been entering her forties, she was touted as one of the most sought-after widows in the entire area.

Being one of the most visible and popular of the Van Winkle family, Gloria enjoyed her spotlight by attending most of the important functions of the community, from Christmas toy drives, to cancer research fund raisers, and the annual Memorial Day festivities on the boardwalk, celebrating the opening of the summer tourist season which the majority of the businesses thrived on. Gloria was well known about town as everyone seemed to know her by sight, if not reputation. She had donated large sums of money for the boardwalk expansion as well as the marina rejuvenation. And on several occasions, she declined offers to run for political posts, including a chance to run for mayor following her late husband's death.

Gloria enjoyed the spotlight, but only to the extent that it served her purposes. When left to herself, Gloria was a quiet, even secretive, woman. The private Gloria that only a handful of residents knew about was a sinfully playful, erotically passionate creature. What most of the general population of Regal Bay didn't know was that Gloria Van Winkle had a sexual appetite the equal of her late husband's. Those who did know, who knew of her sexual energy, wondered if she hadn't in fact screwed him to death. Those who were lucky enough to have experienced Gloria in all her true glory bet that she had.

During the expansion years of Regal Bay, when the Van Winkle brothers were changing the very foundation of the small community, their three wives, commonly referred to as the Van Winkle Sisters, though they were in fact sisters-in-law only, began to explore needs within the female community of Regal Bay, At first, with the opening of the Regal Bay Golf Club, they invited wives of the men who were working to reshape the area to form a sorority, and eventually this became known as the Regal Bay Wives Club. During the course as group dinners and get-togethers, it became clear that for all their love for their husbands, many of the women were no longer satisfied with their sex-lives. With their husbands always working, and seldom free for even an evening let along any sort of weekend, the women began to explore other opportunities. And with the three Van Winkle wives, all of whom enjoyed a wide variety of sexual passions, soon many of the women had begun to enjoy the attention of younger, virile men. And with the expansion of the local college to a full-fledged university, the influx of horny young studs filled their needs.

So it came to be that Gloria Van Winkle, along with her sisters-in-law Greta and Gwen, formed the more secretive and sinful Regal Bay Matrons Club. Originally catering to the needs of well-to-do women of middle age, in time their roles expanded. All told over the years, more than one hundred women had become members of one form or another.

During these years, Gloria had mothered five children with Hugo over the course of seven years. Twin daughters Gina and Ginger came along first, and then Gretchen, and finally twins Glenn and Glenda. As it stands, Gloria's line of the Van Winkle family now included five grand-children. When the entire "First Family" of Regal Bay is accounted for, the numbers over three generations totaled more than thirty. With all three of the elder Van Winkle men having passed away, the three "sisters", Gloria, Gwen, and Greta, had taken on the hierarchical roles their husbands had niched out in the community. Greta maintained her position as President of Regal Bay University. Gwen had taken a more prominent role in the community, as director of the community library as well as the Liberal Arts Center. Gloria had taken on the burden of running the Golf Club and the expanded Resort in addition to her duties as a member of the Board of Directors at Regal Bay University. She was also a member of the board at the new Regal Casino. All in all, Gloria was a very busy woman, always on the go, and seldom at a loss for things to do, either professionally or privately.

Small talk between the department heads standing around the table filled the conference room as each gather up their things and began to file out. "Gabriel, might I have a moment of your time, please?" Gloria asked as the group began to file out of the conference room.

"Yes, Ma'am," the youngest member of the board replied. Gabriel Bryant was her grandson, the oldest son of her daughter Ginger and had recently graduated from Regal Bay University with degrees in management and marketing. Still only 25, he was in line to take over much of the responsibilities from Gloria, when she decided to step down.

Gloria took his hand in hers and waited until the last of the group had left the room, although the door remained open. "I'd like to see you tonight. Come around after nine. I am dining with Natalya and Gabriella to go over our proposal to the LPGA. I'd like to discuss a few matters with you, as well. That is, if you're available, and up for it?" Gloria's wicked little grin gave Gabriel all he needed to know about what his grand-mother, and boss, had in mind.

"I do have dinner plans, but I'm free after," he replied.

"I don't mean to take you away from that dear young lady of yours," she smiled apologetically at her grandson. They were the same height, at 5'7", and their eyes were on the same level. She held his for a moment, and then added, "As long as she is tending to your needs, we can meet some other time. Maybe tomorrow morning."

Gabriel felt unease grip his chest, for he knew quite well what was being asked of him by his grand-mother, and he wanted nothing more than to please her, and pleasure her. "As a matter of fact, Ma'am," he stammered, "Krystal and I were looking to call it an early evening. She does have early classes in the morning. I can free to stop by sometime after, maybe nine would be good?"

"That would be splendid, Gabriel," she smiled warmly, and then gave him a light kiss on the cheek. "It's a date, then," she added in a whisper, and gave him a quick kiss across his lips as well as a lingering swipe of her open palm across the front of his slacks. She found that she still had quite the influence over her handsome grand-son.

Gloria was well aware that by the time Gabriel had graduated from high school, he had been having sex not only with his own mother, Gloria's daughter Ginger, but for several years that the young stud had been having sexual relations with several of his relations, including at least two of his aunts, as well as a couple of cousins. However, Gloria had the honor of having been his first true lover, an afternoon both of them would never forget. After all, they had a very close, uniquely open, and sexually affectionate family.

Gloria arrived at her mansion of a home, which sat along the golf course, shortly after eight that evening. She pulled her two-year-old Cadillac CLR into the open garage, activating the door as she shut off the engine. She recovered her cigarette from the ashtray and her purse from the seat beside her, and then passed through into her quiet home. Gloria still lived in the massive house Hugo had built along the fairway to the first hole of the golf course, some forty years before. She lived alone now, with the exception of a young housekeeper who lived in the above-garage apartment, though few weeks went by that some out-of-town relative or other was staying with her. And when her family wasn't visiting, Gloria had friends, very close friends, who would gather for delightful dinner parties, casual evenings, or the occasional orgy. As the matriarch of the Matrons Club, Gloria often hosted gatherings of the members, at times hosting up to a dozen or more women, for dinner, drinks, and story-telling. At times, a young man or two would be invited as well, to provide a little side entertainment, either for the group or privately for an individual. Gloria had a Rolodex full of young, willing men who enjoy nothing more than to provide sexual services to the Matrons of Regal Bay, and her grand-son, Gabriel, was one such young man.

Upon his arrival at just a few minutes past nine, Gloria greeted her grandson warmly, with a hug followed by a lingering kiss. She had no issues with showing such sinful affection to her family members. She was also on her second cocktail since returning home.

"Come in, Gabriel, darling," Gloria insisted. "Can I get you something to drink?" She led him through to a side room overlooking the expanse of front lawn that was used as a sitting room.

"A beer would be nice," Gabriel replied as he pulled off his suit jacket and hung it on the hallway rack. Following his grand-mother's household rules, he quickly stepped out of his loafer shoes.

The drapes were partly open, and Gabriel could see his white BMW 318is sitting out front, on the curve of the drive. He was proud of that car, his first major purchase after graduation, and his only real expense. Gabriel lived in an above garage apartment on his parent's property until he decided on his own home. That wouldn't happen until he was sure of staying in Regal Bay. The room he now sat it was warmly furnished and comfortably lit. The only technology his grand-mother kept in the room was a small Bose radio that had been tuned to a soft jazz station. Gloria loved jazz. Gabriel was fifty-fifty with it. He'd rather listen to techno-dance music. Something with a heavy beat, he always said.

Gloria joined her grand-son in the front room, carrying a bottle of Sam Adams in one hand and her freshened drink in the other. Her drink of choice that evening was a Sangria, a pitcher of which her housekeeper kept fresh in the refrigerator. Passing through the sliding doors elegantly, Gloria enjoyed the look upon her grand-son's face. After meeting him at the door, and while retrieving their drinks, Gloria had dropped the evening dress she had been wearing and now moved with all the grace of a mature, beautiful woman to hand him his drink. Gabriel took in the refined sex appeal of his grand-mother, who at 67 years was still strikingly beautiful. Her figure was slim and lean. Her flesh was deeply tanned, from her heritage as well as long afternoons under the coastal sun. Her long, black hair was down and fell to just above the small of her back. The pale blue slip she wore did little to cover her wonderfully firm breasts, which he knew she had had done some years back, or the wonderful swell of her butt.

Gabriel had always enjoyed watching his grand-mother walk, especially from behind. Her ass was tight, tiny, and beautifully rounded, and had been for as long as he could remember. Her legs were long and lean, and he had often enjoyed them wrapped around his torso, or slung across his shoulders. By contrast, Gabriel's mother had inherited all of his grand-father's German traits, being blonde, big-breasted and thick-bodied, and having a boisterous personality. Gabriel loved his mother dearly, and loved making love to her, but there was something exotic about his grand-mother that Gabriel had always had a passion for.

Gabriel accepted the beer from his grand-mother, who then moved to sit beside him on the small sofa, looking out towards the front law. She reached up and turned the near-by lamp off, leaving only a single overhead light on.

"Tell me about your date, Honey," Gloria insisted. She sipped from her drink as he did his, and laid a hand provocatively upon her grand-son's thigh, high up.

"You've met Krystal," Gabriel began, knowing that his grand-mother knew Krystal Heron, daughter of Katherine Heron. Katherine ran in the same circle that his grand-mother did. "She and I get along pretty well, most nights. Tonight wasn't one of them, though," he explained. "We ended up arguing on the drive back to her place."

"What about?" Gloria asked.

"Well, she wasn't real thrilled about me meeting you this evening. She wanted to spend the evening together, as I'd promised her. I told her that I had thought she had wanted to get home early for class tomorrow, and I guess I was wrong. She'd gotten rid of her room-mate so that we could have fun after dinner. I told her that if I'd known I might have changed my mind about meeting you tonight."

"She was just wanting a little something that I want as well," Gloria grinned over her drink. "You should have put out. I'd like to get a taste of her sometime, even if it's fresh from your wonderful cock!"

"Grandma!" Gabriel gasped. It didn't help that her hand was resting on his crotch.

"You know, I once had sex with her mother, right here where we are sitting," Gloria proclaimed. "She was wonderful! That young woman knows her way around a pussy with her tongue, I might add. And if her daughter tastes half a good...Yum!"

"I wouldn't know," Gabriel replied. "About her mom, I mean. I know how good Krystal tastes."

"I'd bet that's the only reason you put up with that girl, is to get to her mother, isn't it?" Gloria asked with a laugh.

"Not hardly! There's more to Krystal than sex, you know," Gabriel defended, even though he knew she was right. He'd love to get a chance with Katherine Heron, and having both at the same time was his ultimate dream.

"Who cares about all that other shit?" Gloria barked. "Sex is the only thing that matters to women. A good cock, a good tongue, a gentle touch. If a man has all of that, and a willingness to experiment from time to time, that's all a woman is looking for. Beer belly, smoking, drinking, sitting in front of the television watching sports, out running with his friends, or other women, all of that is ignored if he can give his woman a good old fashioned orgasm when eve she needs it. And I'm telling you this, right now young man, that your old grand-mother needs it. So let's stop talking about your girl-friend troubles and take this evening to a new, pleasurable height, shall we?"

Gabriel finished off his beer and smiled back at her, giving her a wink. "I'll do my best, Grandma."

Gloria leaned in close and pulled his mouth to hers. After kissing him, she told him, "I don't remember a time you didn't give me your best, young man." She then stood up and pulled him up with her, leading him by the hand through to her bedroom suite at the top of the stairs. As she went around pulling open the curtains to the view of the fairway beyond the back yard and dimming the lights, she removed her slip. Her large, heavy, matronly breasts fell free, sagging with age but only slightly, again thanks to the augmentation. They were still full and prominent, displaying thick nipples the color of chocolate at the peaks.

As Gabriel watched her in silence, Gloria stepped out of her pink panties. Now fully nude she approached him and with a sly grin she asked, "Do I still do it for you, young man? Do I still make you as hard as ever, as when you use to spy on me, with your grand-father, or your uncle, or your father?" As she spoke, Gloria stroked her grand-son's prominent bulge at the front of his slacks. She pulled his mouth to hers and then kissed him, deeply. All the while she squeezed and stroked his bulge.

"You're sure doing something for me, Grandma," Gabriel gasped as he felt his cock growing rapidly, and uncomfortably, in his slacks.

"I can sure tell, if this volcano growing between your thighs is any indication!" she giggled. "And Gabriel, haven't I told you? When we are together, you're to call me Gloria. Is that understood?"

"Oh, yes Ma'am," Gabriel replied with a moan, as Gloria began pulling at his belt and slacks fastener. His zipper went down and his cock popped free, sticking through the front flap of his boxer shorts. Their lips came back together and Gloria reached down to wrap her long fingers around his growing manhood, while he moaned into her mouth.

"Look what I found hiding!" she teased as she stroked Gabriel's cock. Now free of his confining underwear, it began to lengthen and harden in her gentle grip. "A trouser snake looking for a warm, wet hole to hide in, I suspect." As Gloria continued to pull at her grand-son's familiar cock, Gabriel shoved his trousers down, stepped out of them and his underwear quickly, before pulling her bodily to him to redouble their intimate kiss.

A minute passed before Gabriel broke his mouth away from Gloria's and with a playful snarl said, "Goddamnit, Gloria! Open up!" At first Gloria thought he meant her mouth, a request which she was more than willing to comply with. However, Gabriel had another thing in mind and roughly shoved her back until she fell across her bed.

"Oh!" she gasped as she hit the mattress, her large tits slamming against her chest with an audible slap before settling to either side of her chest. Gabriel looked down upon her with hungry eyes as he pulled off his shirt and undershirt in a single motion. Now as naked as she was, Gabriel took hold of her legs just above the ankles and pushed them apart, opening her up for him. Giving his grand-mother's crotch a hungry look, Gabriel noticed that she had trimmed her pubic patch of dark fur to a small arrowhead-like triangle, pointing invitingly at the thick bulge that was her clitoris, nestled at the top of the long, dark-flesh slot that was his grand-mother's vagina. Her slit was aged and wrinkled, with thick, chewy labia that parted as he pushed her thighs apart wider. Her juices had begun to flow, giving her inner flesh a slight glint as he took her in with his eyes. Gabriel loved the sight of his grand-mother's pussy, and never tired of it spread out before him in all its wonderful glory.

SteinWolf8
SteinWolf8
469 Followers