The Matrons of Regal Bay Ch. 50

Chapter 50

Gwen's Tales -- Part 1

Gwen Van Winkle sat in her favorite wicker glide-rocker overlooking the marina and much of Regal Bay proper from the height of her home's third-floor balcony. The old town, the bay-front village that her husband and his brothers had taken, remolded, and grown into a thriving young city, stretched out to the left and right of her. Whereas Jonas and Hugo, Oskar's brothers, had built large mansion-like homes among the foothills of the Majestic Mountains to the east of town, Oskar had taken one of the older buildings in town, had it remodeled, and settled his family there.

Oskar had always felt that to truly know a town and its people one must live amongst them, work with them, eat with them, and enjoy life with them. So it was that Oskar, Gwen, and their children, twin daughters Sophia and Olivia, and sons Garrett and Graham, grew with the town at its heart. Sophia and Olivia no longer lived in the big, renovated house. Neither did Oskar, who passed away many years ago. But Gwen did not live alone in the three-story building. Her youngest son Graham, along with his boy-friend Nathan, occupied the third floor, below what Gwen referred to as her apartments on the third floor. The second-floor bedrooms that had once belonged to her daughters had been converted to a small library/office that Graham had taken upon himself to stock, and a sewing room, where Gwen had started spending more of her free time following her retirement. The first floor was the communal area, with kitchen, dining, living, and a music room where Gwen relaxed at the grand piano Oskar had sent over from Germany for their fifth anniversary. Gwen was an accomplished player, and in her retirement, she spent many hours playing, often alone but on occasion she would have an audience.

Since her husband's passing, and her retirement shortly thereafter, Gwen had slowly become more and more of a home-body. As she rocked, looking out across the sparkling bay waters, she couldn't recall the last time she'd driven a car. The last time she'd ridden in one was when Olivia had taken her out to the mall shopping for new clothes, back in the spring. When Gwen wanted to go out, she usually walked. She enjoyed walking the old streets of downtown, and along the boardwalk. She didn't venture out onto the beaches often, as the years had taken its toll on her ankles and they easily twisted in the soft sands. Gwen did enjoy going out onto the bay, riding along with one of her long-time friends as they sailed or motored along the coastal waters. Even those day-trips were becoming fewer and farther between, though.

On this evening, Gwen had played piano alone for a while, and after a quiet dinner with Graham and Nathan, she now sat on the balcony outside her bedroom, a pot of fresh tea on the table at her elbow and a cup in her hand. She often sat outside watching the bay and the boats coming and going. The fishing trade was still thriving and with darkness falling, the trawlers were headed out. Their honks of greeting echoed across the calm bay waters, as did the thrumming of their diesel engines. All in all, it was a very peaceful and calming night. It was the last night of July and Gwen often spent this night alone with her memories. It was on this night, twelve years ago now, that she lost Oskar to a heart attack at just 65 years of age.

Gwen was now 63, having celebrated her birthday earlier in the summer. As she always did on this evening each year, she reminisced about her life in Regal Bay, reflecting on the life she'd made for herself and her children. There had been many good times, and a few bad. She had married into a family that took very seriously the concept of love in a tight knit family. She had learned very early on that she was to enjoy the sexual attentions of all her in-laws, and for the young woman from Oshkosh, Wisconsin, her first year as Oskar Van Winkle's wife had been eye-opening to say the least. She had married Oskar when she was only 22, and he was a seasoned 36. They didn't begin their family for nearly six years, during which time Gwen had delighted in the attention all three Van Winkle brothers gave her, as well as various other men, and a few women, in the extended family. She had been taken by Oskar's father on their wedding night, something of a family ritual she was to learn, as a way of officially being brought into the family fold. Jonas, the middle brother, had been the first to marry, and Gwen soon became not only tight friends with her sister-in-law Greta, but Greta became Gwen's first female lover. Gwen and Greta made love nearly as often as Gwen made love to her husband during those first few years. To this day, they still enjoyed each other's company, after more than four decades.

Gwen turned her thoughts to her daughters; Olivia and Sophia. Olivia still lived in Regal Bay, with her husband Vincent and twin daughters Emily and Amy. Olivia had recently taken soul ownership of Glorious Gowns and Nobel Tuxedos, a business she'd begun working at as a novice seamstress right out of college, and after six years as manager, Olivia was offered ownership by Kathy Gates, the original owner and one-time mistress of Oskar. Olivia's husband, Vincent, was now the Chief Fire Investigator for the Regal Bay Fire Department. He had taken a job in the fire department after he and Olivia had married, shortly after she had graduated from Gonzaga University in Spokane. They already had twin daughters, who Gwen and Oskar had taken in for the first two years of their life, until Olivia had finished school and Vincent had settled on a career.

Sophia, Olivia's twin sister, had also married shortly after graduating from college. She and her husband, Isaac Barrett, now lived in Sacramento, where Isaac was a junior partner in a law firm. Sophia worked at the California State Capitol as an Information and Records Clerk. Unfortunately, soon after they were married Sophia learned that she would be unable to have children, something that would bother her for many years, to the point where Sophia had been in therapy for depression much of her married life. Sophia and Isaac would visit Gwen in Regal Bay several times during the year, and Gwen would make the drive to Sacramento as well, usually with her single older son Garrett.

Garrett, her third child, was two years younger than his twin sisters. He had married young, and divorced just as young, with no children. Since, he put his full attention to his work at Regal Bay University, where he sat on the Board of Directors as well as acted as the school's legal team's head lawyer. Gwen suspected that her handsome son had enjoyed time with many of the beautiful young female students through the years, though he was careful not to get too involved. Gwen didn't mind his side hobby, so long as he found time to pay her a visit, and take care of his mother's needs. Garrett knew his mother well, and treated her well, just as his father had.

Gwen's youngest son Graham had been gay all his life, as far as Gwen could tell. She never feared for him, not within a family that was so very open and honest, and politically powerful within the community. Graham lived with her, along with his companion Nathan, and took care of her and her home. Both young men worked for the city, with Graham in the City Planners Office and Nathan in the Parks and Beaches Department. They respected her and her life-style, as she respected theirs. Gwen was fond of Nathan, and was growing to love him as she loved her sons-in-law Vincent and Isaac, though she may never bed Nathan as she did her daughter's husbands.

***

Isaac Barrett first came to Gwen's attention when her daughter Sophia returned home from college on spring break. With her she brought along Isaac, a fellow student who was five years older that Sophia. Isaac was working through graduate school towards a law degree, and Sophia was very much in love with him. In Gwen's eyes, Isaac was a very plain looking young man, with a high hairline that was already running towards a balding spot at the crown. He wore glasses, was slightly chubby around the waist as well as the neck, and had a voice that tended to grate on one's nerves when he got excited. He was maybe an inch taller than Sophia, who was still very slim although her breasts had finally begun to fill out. She'd only just started wearing d-cup brassieres and now was looking to go shopping wither mother to look for dd-cup, or maybe even e-cups.

"I really can't go with you this afternoon, darling," Gwen told her daughter. "I have a plumber coming by to fix that toilet on the second floor. I can't use mine until that one's fixed, and I'm getting tired of rushing all the way down here to go to the bathroom."

"That's okay, Mom," Sophia shrugged. "I'll call up Denise Masters and see if she wants to hang out."

"What about Isaac? Will you be taking him with you?" Gwen asked.

Sophia paused with a long look at her mother. When Gwen finally made eye contact, Sophia asked, "Would you rather I took him along, or leave him here? I think you'd rather the latter, as I'm sure you've been thinking it's time to introduce him to our family ways in the proper manner, haven't you?" Even as she tried to maintain a solid, stern look at her mother, Sophia eventually was grinning.

Gwen shrugged as a reply. "He's your husband, darling. It's up to you." Gwen reached up and popped one of her day-blouse's buttons to display a little more of the plunging valley of her cleavage. The top edge of her lace bra was now exposed as well. She did all this with a wicked grin on her face.

"What do you think?" Gwen asked. "Do you think this old bag can entice your young husband into sin?"

Sophia drew up and placed her hands on her mother's shoulders. "Mom, by the way Isaac's eye kept going to the older women on the beaches of Oahu during our honeymoon, when they should have been on me the entire time, I think you've got a fairly good chance of finding out just how much meat my loving husband has packaged away in those Dockers he's always wearing. And then you'll know just why I wasn't letting this man go, even with so many other, hotter, stallions hitting on me at school. Isaac is a woman pleaser, and if you work him just right, you'll be as pleased to have him as your son-in-law as I am having him as my husband." With that, Sophia kissed her mother, full on the mouth, and then retrieved her cell phone. She had her high-school friend on the phone a moment later, as Gwen began to wonder how to best approach the newest member of their sinful family.

"Where is Isaac?" Gwen wondered.

Sophia overheard and said, "He's still in bed, last I saw, Mom." Gwen noticed her daughter's sly smile. "I think I might have used him up last night," she added. Sophia grabbed up her purse and car keys and headed for the front door. "I'll see you later, Mom."

Gwen watched her daughter leave and then realized that with Oskar at the golf club all day attending several meetings with investors, and her boys in school until after 3pm; it would be only she and Isaac in the house for the next several hours. Given that she had been all but told to seduce Isaac by her daughter, Gwen was beginning to feel the need to check in on her young son-in-law. Maybe she'd have something exciting to tell Oskar that evening as they lay in bed.

She found Isaac in the bedroom that was once Sophia's alone, but had been updated to a more guest-friendly room. The décor was no longer teen-girlish, but more of a contemporary style, with wooden furniture, a full-sized bed, a reading chair near the window, and a couple of tables. Gwen had been starting to think of the room in terms of a place for her to relax, and often she would bring in her sewing, a hobby she had begun to pick up.

Isaac lay in the bed, a white sheet drawn up to his shoulders. He was still soundly asleep, even though the morning was getting late. Gwen stepped into the room and quietly shut the door, even though the house was now empty. She wanted to waken Isaac personally, in her own enjoyable way.

Gwen noticed immediately that the room stank of sex. No doubt, her daughter had enjoyed a morning fuck before getting out of bed. The aroma immediately set Gwen's crotch afire. Her daughter had known all along what her mother would do, and had purposely not said anything before leaving.

Gwen gently pulled the sheet from his upper body and eased onto the bed beside Isaac. Kneeling, she tossed the sheet away to find Isaac wearing blue boxer shorts. He hadn't awakened yet, so she began to run her hands along his body. Isaac had a bare chest, with no hair and dark nipples the size of nickels. His belly was slightly round and would soon begin to run to fat, she recognized. She leaned in to give his nipples a kiss, and that helped wake him. They were obviously very sensitive.

"Mrs. Van Winkle!" Isaac gasped when he saw her. He pushed up and back into the headboard. "What are you doing?"

Gwen smiled. "I'm sure my daughter has told you about her family. And it's something of a tradition with us to welcome new members into the family in an intimate fashion. With you, that duty falls to me, young man."

Isaac stammered, "I thought she was bullshitting me. I didn't think she was serious."

"I know this might be much for you," Gwen continued. "It was for me, when I agreed to marry Oskar. But Sophia was brought up to love her family, and as part of the family, we expect nothing less from you. However, I won't force you if you don't want to." Even as she said this last, Gwen was tugging at his boxers. When he lifted his hips enough for her to completely remove them, she knew that she had him.

Gwen took in the sight of his short cock, laying in the thick forest of dark pubic hair. It was little more than her thumb as it was. Sophia had bragged about his endowment, so Gwen figured that it would take a bit of work to get her son-in-law into usable form. Gwen reached down and wrapped her fingers around his chubby dick.

"What about Mr. Van Winkle? Or Sophia?" Isaac asked nervously as he watched Gwen begin to stroke his cock to life.

"Oskar is aware of what I have in store for you," she smiled. "And Sophia all but pushed me in this direction when she left this morning. She thought that you were ready to join in the family way." With that said, Gwen leaned over and took Isaac's dick into her mouth.

"Oooohhh," he sighed and fell back into the pillows. The warmth of her mouth pushed all anxiety from his mind. Until Sophia had come along, Isaac had never had a blow job in his life. And now here was her mother giving him one as well. If this is what life in the Van Winkle family was going to be, then Isaac Barrett had hit the jackpot.

It only took Gwen a minute or two of oral work to get Isaac full and ready. Her daughter had not lied about her husband's endowments, either. His cock grew longer by the second, until it was easily nine inches long, as long as Oskar's manhood. The crown also transformed and ballooned out into a golf-ball like knob that was quite a bit larger that the shaft it topped. Gwen marveled at the sight, as the boy's knob was larger than either of his balls.

With a final mouthful of cockhead, Gwen popped off Isaac and asked, "Would you like to put this wonderful tool to work?"

"Oh, hell yes!" he replied quickly. His eyes never left her as she stood and removed her clothing. Once as naked as he was, Gwen returned to the bed and turned her hips to him.

"Go ahead, Isaac. Stick your dick inside me." She lifted her left leg and rolled slightly onto her side. Isaac rolled to meet her and guided his cock into contact with her vagina. Her hairs tickled him as he stroked through, and when he felt her opening kiss the tip of his knob, he didn't hesitate. He pushed forward and entered his mother-in-law's pussy with a smooth, easy thrust.

"Oh, that's it, my boy! Push that long cock up into my hungry pussy!" Gwen moaned. Isaac followed her directions and with only a couple of thrusts he managed to fully embed his dick in her. "That feels so good," she sighed. "Now fuck me, Isaac. I want to feel you work this old cunt over. Do me like you've been doing my daughter."

Isaac didn't need her encouragement. He was already getting a firm grip on her leg. He pushed his cock a bit deeper into her and felt the hard wall of her uterus against his knob. He backed off a few inches, and then rammed inward again. Gwen gave off a satisfied grunt, and Isaac began to drill her with the same long-dicking thrusts he had given to Sophia just an hour before.

Gwen had been impaled on Oskar's equally long cock for so many years that the pounding Isaac's was giving her was welcomed. Few men in her world could match Oskar in length, and now that she had found another, she would be taking every opportunity to enjoy him. And the huge, round knob Isaac sported was doing new and exciting things inside her as well. She once had a toy that had a ball for the end, and Isaac's cock reminded her of that. Thoughts went to having Isaac sodomize her with it.

Isaac had already dumped his initial load for the day, and as such he would be able to last for a good long time with his mother-in-law. If Sophia had indeed set him up, then he knew that the morning quickie had been to set her mother up. It was all fine with him. Even though he had never thought about having sex with an older woman, Gwen had an attractive sexuality to her that defied age. Yes, she was the same age or there about of his own mother, but he would never have been able to get hard with her. His mother was a fat, chain-smoking slob of a bitch that had driving his father away years ago with her non-stop badgering. Isaac shook his head to clear his mother out of his thoughts, and returned to the sensations his new mother was giving him.

His hands roamed her flesh, and even though Gwen had put on some soft weight in the past few years, she was still well proportioned. Her breasts were soft and shook with every thrust of Isaac's cock into her body. His hand had one in a firm grip and she pulled the other up to give her nipple a playful lick. Isaac saw this and leaned over to give her second nipple a similar tonguing. Bent as he was, Isaac couldn't do much more than wiggle his hips. After a moment, Gwen suggested they change things up.

"Let me ride you," she told him. "Lay back and let me ride your long dick."

Isaac was more than willing to let his mother-in-law be in charge, and again followed her direction. He lay back into the pillows and watched as she straddled him, facing away. He held his cock in hand and she nudged the tip in line with her hole. His hands dug into her ample ass as she slowly lowered herself down the full length of his cock shaft.

"Oooohhh," they sighed together as they rejoined. Gwen didn't pause, and as soon as he was fully inside her, she began to rebound, rising until his round knob threatened to pop free before plunging back down.

"Oooohhh, god! You feel so good inside me, Isaac!" she huffed as she fucked herself upon him. His hands worked her ass and spread the cheeks, giving Isaac a view of her asshole. He would be visiting it very soon, if she had her way.

For many minutes Gwen bounced upon her son-in-law's long shaft, and she enjoyed an orgasm that had her cream lubricating her lover's shaft well. "Aaaahhhh, sooooo goooddddd!" she moaned as her body gently convulsed around his shaft. As she climaxed, however, she maintained her steady fucking of his cock with her trembling cunt. It was a nice climax, but nothing near what she had come to Isaac for.

Gwen continued to ride Isaac for many more minutes, enjoying his unique cock in every possible angle that she could get. Eventually, she wanted him to pound her, and eased up and off him. As she rolled into the bed beside him, she said, "I want you to fuck me, now, Isaac. Give me your cock, hard and deep."