The Matrons of Regal Bay Ch. 50

Isaac rolled into position between her spread legs and took aim. Gwen pulled her knees up and he saw her hole open wide. He pressed his hips down and entered her with ease. "Now fuck me!" she demanded. "Put that fucking cock to use and fuck me with it!"

Isaac obeyed, and started ramming as hard and as deep into Gwen's cavernous cunt as he could. The bed bounced and banged against the wall as he fucked her, going so deep with every thrust that his knob crashed into her cervix and his balls slapped hard against her anus. The smacking of his scrotum against her asshole was giving her little jolts of delight that had her pussy juicing up nicely once again. The added lube was all Isaac needed to redouble his assault of her willing cunt. She dug her finger nails into his shoulders as he leaned above her, wanting to leave marks for her daughter to find.

"That's so very good, Isaac," Gwen purred as her body began to tremble once again. "Keep that up, baby, and Mommy will be cumming again!" She smiled as his eyes widened at hearing her words. She felt his smooth rhythm falter ever so slightly, and pick up again as he began to smile down at her. He was finally accepting that this encounter would not be the last time he would be making love to her, his new mother.

"I love you," Isaac muttered under his breath, but Gwen heard. She reached up and stroked his head, and then he lowered himself fully atop her. His mouth went to hers and for the first time in their relationship, Isaac kissed Gwen as deeply, and as lovingly, as he kissed his own wife, and her daughter. Her mouth opened and she sucked his tongue in. In that moment, she felt his cock pulse wildly as he stuffed his cock deep and held it there. Isaac groaned into her mouth as his semen began to paint her womb.

"Uuunnngggghhhhh!" Gwen growled back at him, and as his seminal warmth flowed through her body, her own orgasm began to peak. Her pussy fluttered around his shaft and as her back arched upward, her cream gushed out. "Oooohhh, Christ! That's it! That's it!"

Isaac was panting heavily atop her after pulling him mouth free of hers. He looked down into her face, her features screwed up as if she were in pain as she climaxed. He could feel her pussy around his cock fluttering, and it felt so much like Sophia's. Even Gwen's face reminded him of his wife as she enjoyed her orgasm, even though the two looked hardly alike at all at most times.

With his load deposited high into his mother-in-law's body, Isaac rolled off her and collapsed beside her. The room seriously needed an airing out, he realized.

Gwen rolled into his shoulder and draped an arm across his bare chest. Both of them were sweaty and in need of a shower. "Thank you, Isaac. That was wonderful."

Isaac had no idea what to say. He finally nodded, and replied, "Thank you, Gwen. I liked it myself." Gwen gave his cheek a quick kiss before she rolled away. Gathering up her discarded clothing, she told him, "I've got some errands to run today, if you'd like to join me."

"I'd like that," he replied, and Gwen smiled to herself, knowing that he would do anything she asked of him, now that she's shown him what life in the Van Winkle family was like.

Still naked, she turned back to him before heading out of the room. "After, if nobody's back yet, maybe we could enjoy another roll in the hay!"

"I'd like that, too," he grinned.

***

Gwen returned to her perch on the balcony with a fresh pot of hot tea. She had enjoyed Isaac so many times in the years since she first introduced him to their lifestyle that she'd often have trouble recalling them. After pouring a cup full of the tea, she settled into the wicker seat to watch the bright, full moon ever so slowly make its way downward towards the black waters of the Pacific. The gentle breeze tickled her nipples beneath the nearly sheer night gown and she felt them bud up. She also felt the cool fingers of the wind play along the insides of her thighs, right up to her naked crotch, and she let her legs spread just a little more. She enjoyed the feel of night's cool breath upon her damp slot, which made her body shiver excitedly. She sipped warm tea as her thoughts turned to her other son-in-law, Vincent Wilson, though not the first time she'd enjoyed him and his wrist-thick manhood, but to the evening Vincent was invited to a family orgy for the first time, on the day his twin daughters were born.

Except for Isaac, who was busy with work in Sacramento, and their youngest son Graham, who was at school, the family had gathered for the birth of Olivia's twin daughters. They had flown up to Spokane on the family jet, though technically it was owned and operated by the Van Winkle Foundation. The hospital was located some miles from the university, where Olivia still had another year of school to complete, and where the apartment she and Vincent lived.

Vincent was a few years Olivia's senior and had begun work after graduating from Gonzaga as a fire fighter. He was a big, sturdy young man, and having played Rugby for the school, he displayed several past injuries, including a nose that had been broken many times. He was ruggedly handsome, Gwen thought, and reminded her of a lumberjack more than a fire fighter.

The family had witnessed the birth of the twins, and after several hours, they left to let Olivia sleep. After a dinner at Pizza Hut on the way back to the hotel, everyone was invited to the suite Oskar had paid handsomely for. It didn't take long, or many drinks served, before the celebratory festivities began.

As Olivia recovered in the hospital, Oskar and Gwen, together with Vincent, Sophia, and Garrett, celebrated the birth of yet another generation of Van Winkles in the time-honored tradition of a family orgy. Within half an hour of their arrival in the suite, Gwen was on her hands and knees, kneeling on the big king-sized bed, with Sophia in a similar position alongside. Behind Gwen stood her son, Garrett, who had his rock-hard cock sliding into her smoothly and easily. He'd been fucking his mother for many years now and knew how Gwen liked to be taken. Her heavy breasts hung beneath her and she bent her elbows so that her sensitive nipples dragged back and forth across the bed's sheets with every lunge. The action sent shivers down her spine and made her pussy vibrate around her son's piston.

Gwen looked over and watched as Sophia gulped her father's long, thick cock down. As Garrett's cock continued to work her pussy over, Gwen took in the delight that was on her husband's face. He was obviously enjoying their daughter's talented mouth, and the loud slurping she made on his manhood nearly drowned out the moans and grunts the men behind them were making. Oskar was relaxed against the headboard, kingly in his demeanor she thought, while watching both his wife and daughter as they were taken by two fine young men. He had been a good father for his daughters and had taught them both, Sophia and Olivia, how to pleasure a man and his tool from the time they understood what went where and why. Behind Sophia's upraised hips was Vincent. Gwen knew that Vincent, although still not a married member of the family, was enjoying the fact that he was allowed to enjoy the pleasures that his fiancé's twin sister offered him. Sophia barely resembled Olivia, yet in Vincent's mind they were very much the same. The 28-year-old fire fighter had already enjoyed Gwen's favors when Olivia introduced him to the family a little more than a year before. This was the first time he had experienced sex with Sophia, however. He was addicted, of that there was no doubt. And so was Sophia, as Vincent was a well gifted young man.

"Oh, fuck, Mom!" Sophia grunted after she let her father's cock fall free of her mouth. She sucked in a deep lungful of air and let her head hang while Vincent continued to pound her from behind. It was the first time she had experienced what her sister had told her about him and Sophia was enjoying it. Her own husband of less than a year was unable to make the trip up to be with Olivia as she gave birth to her twins, and she found Vincent, who was a year older than Isaac, to be very similar in many ways, except for his cock. Vincent was as thick as a beer can, she decided, much like her Uncle Hugo. She'd already cum on Vincent's cock once and was racing towards a second orgasm, and they'd only been enjoying themselves little more than fifteen minutes or so.

Gwen reached over to stroke her daughter's chin. Sophia turned and looked at her with half-lidded eyes. "Didn't I tell you...that Vince has a...fat dick?" she panted along with Garrett's deep thrusts. With everyone, her son's cockhead banged at her cervix, sending jolts of pleasure through her body. Sophia grinned in response and let her head drop once again; enjoying the pounding she was getting from the muscular stud her sister had landed.

When Garrett eventually slowed, Gwen took the opportunity to slide forward away from him and turn around. She brought her son's long cock to her lips and slurped it down. Garrett's hands went to her head and took hold of his mother's short blonde hair. His hips began to rock almost as fast as they had been when he was poking her cunt. Now, her son began to face-fuck her, something he'd learned from watching his father no doubt.

Beneath her, the bed began to bounce faster and she let Garrett's cock go free. Beside them, Vincent was picking up his pace, fucking Sophia with rapid, sharp strokes. "Oh, god! Oh, god! Oh, god!" he was panting. His climax was imminent and Gwen stepped from the bed. Gathered around, Gwen, Oskar, and Garrett watched as Vincent worked both himself and Sophia towards their mutual climax. When it happened, Gwen thought it the most beautiful of sights.

"Oooohhh, yeeeesssss!" Vincent roared towards the ceiling. He slammed his cock hard and deep into Sophia's vagina, which was exploding with its own creamy climax.

"Aaaaaahhhhh!" Sophia cried out. She dropped to the mattress, burying her face into the tangled sheet as her body trembled upon Vincent's fat fucker.

"Take it, Sophia!" Gwen moaned excitedly. "Take all of his hot seed!"

"Give it to her, Son!" Oskar added for Vincent. Garrett looked to his father, who was grinning wide as he watched his daughter cum and be filled with cum, while also stroking his own long cock. Garrett also was jacking his manhood, keeping it ready to go back to work at a moment's notice.

As Sophia and Vincent began to ride down the other side of their shared peak, Gwen rolled back into the bed to lie beside the joined lovers on her back. She reached for her daughter's equally heavy breasts and began to cup the left one. Meanwhile, she spread her legs and told her husband, "Give me your cock, Oskar. I need you inside me."

Gwen's husband, one of the three famed Van Winkle brothers who built Regal Bay up from the Pacific Coast fishing village it once was into the growing, thriving city in now is, moved over to her. He was now looking at her with as much lust as he had been looking at their daughter. He never failed to pleasure her, or any of the Van Winkle women. Even at his age, and Oskar had just celebrated his 65th birthday, his cock was always rock-hard and ready to please. As he knelt on the bed between his wife's spread legs, he gave his long cock, still slick with their daughter's spit, a stroke or two before he leaned across his much smaller lover's body. Gwen reached between them and took hold of Oskar's cock to guide it in, but needn't have bothered. Garrett had worked her over well and her vagina was still agape, ready for her husband to fill her with hot, hard, German-born steel.

"Oooohhh, yeessss! Fuck me, Oskar! Yeessss!" Gwen cried out as her masculine bear of a husband began to drive his long cock deep into her and then withdraw just enough to make her body tremble and beg for more. He didn't disappoint her. He never did.

Standing beside the bed, watching as his mother and father began to fuck once again, Garrett felt left out, but for just a moment. While their parents made love on the bed, Sophia called for her brother to join her at the long sofa that occupied the wall of the hotel suite. Vincent had collapsed against the headboard of the bed and had lit up a marijuana cigarette.

"Sit here," Sophia told Garrett. Once settled on the cool leather cushion, Garrett watched his sister drop to her knees and push his apart. His cock, still throbbing and waving from his brown tangle of pubic hair, was soon wrapped by Sophia's fingers. She stroked him, discovering that their mother's cream still coated him. As their mother and father engaged in intercourse on the bed, Garrett watched as Sophia took his cock head between her lips and began to lap across the tip with her tongue.

"That feels good," Garrett sighed. He slipped his hips a bit further towards the edge and leaned back into the sofa. He reached out and began to stroke his sister's blonde hair when her head began to bob up and down. Inch by inch she took her brother's manhood into her mouth, until she showed him her oral skills by taking his entire length with every gulp.

With her heavy breasts lying on Garrett's thighs, Sophia backed off her brother's dick and wrapped her fist around the base. She then began to work the top few inches over with her tongue and lips, bobbing along at a quicker pace when Garrett's moans, and his cock's throbbing, began to pick up.

"Oh, god! Suck my dick, Sissy! That feels so good!" Garrett was panting while he watched.

Sophia let his cock free of her lip-lock for a moment, to give her brother a broad smile. "I'm glad you like it," she said, adding a lick across his leaking tip. "Maybe we should do this more often." Sophia went back to giving her brother head.

Meanwhile, Oskar had driven Gwen into a moaning orgasm and despite not yet climaxing himself, he slipped free of her quivering quim and headed for the suite's wet bar. His long cock dripped with his wife's cream as he went, something Garrett noticed. "Fuck! That was great!" Gwen declared after a moment of rest. She rolled onto her side, nearer Vincent, and reached for his limp member. She looked up to find him nearly asleep after finishing off the dope. Her attentions turned to where her daughter was giving her son a lengthy blow-job. "I think I want a taste of that," she said to no one in particular, and joined her daughter on her knees a moment later.

Garrett watched as his sister removed her mouth from his cock and presented it to his mother. He'd been getting blow-jobs from his mother for a long time, but this was the first time he'd had both her and another trading off. His balls were being held, and at times squeezed, by Sophia, and as he watched his mother go down his shaft, he felt Sophia's grip tug and twist them.

"Ooooowwwww!" he groaned. He bucked his hips upward involuntarily and the result was banging his knob against the back of his mother's throat. Her grunt told him that she hadn't been expecting it, and Sophia giggled. However, Gwen was an expert cocksucker and held her mouth down upon her son's shaft. She gulped, and his cock popped down her throat. Her lips pushed into his thick hairs as she took him as deep as she could, and then held him there. She stroked her tongue along the underside of his shaft while working her throat muscles.

"Uuunnngggghhhhh!" Garrett suddenly groaned and took hold of his mother's head. He held her in place, forcing her to take his cum directly into her throat as he began to shoot off. Gwen had been in this position before, and knew how to relax. She had to hold her breath as her son's cock throbbed in her mouth and fed his hot semen down her throat. She wanted to taste his seed, and waited until he started to relax before she could pull up. The last of his semen coated her tongue as she pulled back until just his knob was held in place by her lips. She swallowed her son's cum and ran her tongue around his crown to clean up any stray morsels. When Gwen had finally let Garrett's dick fall free of her lips, he was completely spent, and completely limp. Garrett was also panting heavily on the sofa, looking as spent as his cock was. Gwen gave her son a wide, proud smile, and then leaned in to give him a quick kiss.

"Did you enjoy that?" she asked her son, getting only a nod in answer. She turned and gave Sophia a quick kiss as well before turning her attention back to her husband. Oskar stood at the wet-bar, a tall glass in hand. His cock hung heavy from his crotch, invitingly, Gwen imagined.

"What would you like, my husband?" Gwen asked as she stepped right up to her bear-like lover. She stroked his hairy chest with one hand while cupping his heavy balls in the other.

"I'd like to see my wife and daughter pleasuring each other, so that I might pleasure them as well," Oskar replied in his deep growl. Gwen knew very well what he was suggesting, and spun away to take Sophia's hand in hers.

"You heard your father, young lady!" Gwen told Sophia. As she pulled her daughter to the bed once again, she asked, "Would you like to be top or bottom?"

Sophia kissed her mother before replying. "I was top the last time. It's your turn." Sophia leaped onto the bed and lay on her back, to be quickly joined by her mother, who straddled her head before lowering her face between her daughter's upraised and spread knees. As Sophia put her talented tongue to work on her mother's gaping vagina, she felt the bed move beneath her hips. Gwen felt it as well and lifted her mouth away from Sophia's wonderful flavors to find a thick cockhead brush against her mouth. She saw that it was very familiar, belonging to her husband. She smiled, and opened wide. Oskar's cock pushed in.

"This reminds me of the night Daddy took my virginity!" Sophia announced before returning her mouth to her mother's dripping slot. Gwen was unable to reply, as she had Oskar's cock wedged deep into her throat. His thick, coarse pubic hair tickled her nose, as it always did, making her throat muscles vibrate, giving Oskar the added sensations he had come to enjoy. The feel of his wife's mouth wrapped so tight around his shaft, her tongue flicking along the underside as her throat worked his knob, had come to be his favorite act of so many he and she had enjoyed over their long marriage.

Oskar slowly backed his cock from her throat and mouth, and Gwen left it dripping with her saliva. She reached out to help him take aim, and then watched as he plunged downward into Sophia's gaping slot, which drew a long, guttural grown from her daughter's lips that vibrated her clit and cunt. She rolled her hips and pressed hard against Sophia's mouth.

"So beautiful," Gwen sighed as she watched her husband once again slide his manhood in and out of their daughter. She put her tongue to work, lapping up the cream left on his shaft from her pussy as he withdrew, and then a quick flick across her clit as he slowly re-entered. Indeed, this had been how they had been, so long ago, when Oskar found her and Sophia on their daughter's bed, with Gwen atop her daughter sharing each other's pussies. Oskar had said nothing. He just stepped up, pulled his long, hardening cock from his trousers, lifted Gwen's face from Sophia's crotch, and replaced her flicking tongue with his manhood at their daughter's entrance. Gwen pushed her cunt hard into her daughter's face to muffle the scream as Oskar shoved himself home. Gwen groaned through an orgasm in that moment, watching her daughter loose her virginity to her father up-close while having Sophia's mouth locked to her gushing pussy. It was an act that was to be repeated two nights later, with Olivia.

After several strokes along his daughter's love-chute, Oskar pulled free and moved to the other end of the intertwined women. Sophia had her mouth tight to her mother's pussy, but a tap of his cock to her forehead caused her to lift away. Sophia saw her father's penis, just inches away and glistening with her own cunt cream, and as her mother's tongue returned to working her vagina over, Sophia opened wide and allowed his cock to slide deep into her own throat. As good as her mother was Sophia could match her inch for inch when it came to throating a man, thanks to her father's wonderful training.