The Cline's Conquer Time Ch. 06

"I mean, I do it all in bed. It all!" Jackie began.

"So do I, dear." Jocelyn replied.

"Men can do what they want to me. I mean, blowjobs, tit-fucking, cunt, anal, squirting, rimming. My body is a man's playground. You think Grandma does that? Will she suck Derek's dick? No! Will she let him fuck her tits? No! Will she let him fuck her cunt? Well... yeah, she'll probably do that, but she'll probably lay there like a worn out old lady? But will she squirt her juices everywhere? Will she let Derek fuck her ass? Will she let Derek rim her asshole?" Jackie postulated, holding her hands out, asking for an answer from her mother.

"I don't think so." Jocelyn muttered.

**********

Derek avidly rimmed Helena's asshole. He was at first disgusted by the idea, but in practice it wasn't that bad. He found himself soaking her asshole with spit, letting his firm, strong tongue run across it eagerly. He found himself nibbling, kissing, and sucking his wife's grandmother's asshole, and not altogether hating it. He kind of enjoyed it.

Helena was pleased at Derek's eagerness. He was really beginning to dive in. She could feel his tongue rimming her ass and taking a few tentative stabs at her asshole, seeking entrance.

"See, Derek, I knew you'd like it." Helena moaned out in pleasure. "I never had to work so hard to get a guy to suck my asshole. Most young guys are so eager to dig right in." she stated. "Ohhhh yeah! I hate to sound like an old lady, but in my day, men wouldn't go near my asshole. They wanted my cunt! But nowadays, these young guys, all they care about are a girl's tits and asshole. Sure, they still want cunt, of course. But all a guy needs is some tits and ass, right? I won't stop them. A woman's cunt, her tits, her asshole, they all need to be worshipped. I'm glad you young guys are realizing this now."

Derek was too focused on Helena's asshole to respond. And besides, it was hard to speak when you were trying to stab your tongue into your wife's grandmother's ass.

"You'd better get that asshole ready, Derek." Helena called out. "You know what comes next." she added pointedly.

Derek did know what was next. He knew what would be expected of him. He knew why her asshole needed to be soaked with spit. He knew where his dick would soon be traveling. He knew he had to do a good job.

Helena had freed his wrists once she knew he wasn't going anywhere. This allowed Derek to palm both of his wife's grandmother's full ass-cheeks. He dug his hands into the firm fleshy cheeks and kneaded them like dough while spreading them to aid him in his work. Pulling the cheeks apart allowed him to worship the entirety of her ass-crack in lavish, wet licks.

"Mmmmm, you're a good little ass-licker, aren't you." Helena purred. "Who would've known? Not Heather, I imagine." she answered with a cackling laugh. "Look at you, marrying a girl one minute then sucking her grandmother's ass the next." she said, as if trying to point out how weak willed he was. "Clearly, this was the vow you were making. Not to my granddaughter, but to me. You vowed yourself to me and my body, whether you knew it or not. You promised yourself to a Cline, and all men to do so have to go through me. Most I just brow-beat and scare off. But you, you're the first I decided to take as a lover. I think I held out for the right one. I've had a lot of guys suck my asshole, but I don't know if I've ever felt a tongue so eager. You like this a lot more than you thought you would, don't you? You love licking your wife's grandmother's ass, don't you?"

As Derek attempted unsuccessfully to spear his tongue into Helena's asshole, he did have to admit he didn't really hate this. There was something about having this perfect, round mature ass splayed out in front of him, as if it were a piece of art on display. The full, round, fleshy cheeks. The way the cheeks perfectly spread apart to expose her neat, clean, sexy asshole. That tight, tiny, seemingly impenetrable asshole. Derek pulled back to give his exhausted tongue a rest and to admire Helena's ass again.

"I still get offers, Derek. Offers to pose nude, and show off my body, like I told you before." Helena started, as Derek dived in again between her lush ass-cheeks, tongue pointed outward, desperate to conquer that hole. "I can't tell you how many times I have had men practically willing to give me the world just to see what you're seeing right now. Men and women willing pay a small fortune just to see my ass in the flesh. To see my asshole exposed to the world. They say that even though I am a grandmother I could still be one of the top nude models and centerfolds in the world. They told me that if I went into porn, I would become one of the biggest porn-stars in the world. I had to admit I was tempted. They threw the world at me. I had porn stars, men and women calling me up, begging me to join them. All those women, practically begging me to join their ranks and render them irrelevant. Those gorgeous women practically begging for the chance to worship me. Begging to smother their faces into my cunt, or between my ass-cheeks, just for the opportunity. Not even caring to have their faces on camera, willing to be obstructed just so they could see what I'm capable of. Guiding thick cocks into my cunt. Spreading my ass-cheeks, showing off my tight asshole. Licking my cunt, prepping it for cock. Sucking my tits, getting me warmed up. Offering their men to me instead. Willing to admit my superiority on camera just to get at me. Like I said, it was a tempting offer. It was tempting to have the porn world bent to my will, but I declined. Who knows, if you're right, maybe in one of those alternate universes, I am the greatest porn-star in the world."

An image flashed through his head. Helena on the front page of some website, wearing next to nothing, luring people deeper into the website, just to see the delights of her hot body. This image disappeared as quickly as it appeared.

There was a long, warm pause as Derek attempted to spear her asshole. Suddenly, Helena broke the silence.

"AWWW, FUCK YES!" she screamed out. Derek's tongue finally broke through the unclenching barrier of her ass. His firm muscle delved in slowly and curiously, forcing its way through her clenched asshole.

"Do it, Derek! I want you to dig deep and get that tongue inside my asshole! I want to feel the whole thing up my fucking ass!" Helena commanded. "If you plan to get your cock in there, you'd better be able to get that fucking tongue inside!"

Derek pushed at her ass forcefully, forcing his tongue deeper.

"I want to feel those lips against my asshole. I want to feel your lips against my asshole and that tongue inside it. I want you to French kiss my fucking asshole!" Helena squealed.

Helena's sphincter was stupidly tight. It gripped his tongue like a clenched fist, pinching it roughly, depriving the firm muscle of blood, nearly numbing it. But Derek didn't stop. He kept pushing for a few agonizing minutes, never giving up, till he got as much of his tongue as he could into her tight asshole. Finally, he could go no farther. His lips were pressed against her asshole and his tongue was extended as far as it could from his mouth, to the point where it was nearly painful. But that was the sacrifice he made to pleasure Helena's asshole. He maneuvered his tongue inside her, trying to pleasure her.

"Ahhhh! That's it, boy. That's it!" Helena gasped, reaching back and grabbing Derek's scalp, holding the young man's face against her ass. She swiveled her hips, rolling her ass against his face. She pressed his face roughly against her as she forced her ass back against him, smothering the young man in her firm ass. She held him there as he began to struggle for air.

"AHHH, RIGHT THERE!" she said while clenching her eyes shut, shivering through a small orgasm. She released Derek's head from her rear and his mouth left her ass with a small pop. It was just in time, as his face was red from lack of breath.

Helena wiped her brow as the young man gasped for air. Helena did not let up for one moment. She put her hands on the bed and pointed her ass at him.

"Alright Derek, you can't get a girl wound up then back away. You can't feed someone an appetizer and deny them the main course. You licked my asshole till I came. I think you know what comes next." she said, turning away.

Derek looked down at Helena's ass, again. He knew what she expected. He looked down and noted his dick was sticking out in front of him, rock hard again. Somehow, even after the hardest cum of his life, sucking her asshole had energized his cock into throbbing hardness again. He looked from it to Helena's spit soaked asshole. Then he looked past Helena's bent over frame to see his wife.

His wife was breathing slowly in her drunken slumber. Even so, she still looked cute. Derek smiled a bit, but then he remembered where he was, and what he was doing. The only way forward was to prove Helena wrong, to bite the bullet and spend the rest of the night pleasuring her, just so he would never have to do it again. So he could live the life he dreamed of with Heather.

So, he had to do it. He had to fuck his wife's grandmother's ass... for the sake of his marriage. He had to stick his dick inside of the tightest hole he had ever encountered, to protect his wife from confronting Helena's sick twisted ways. It's not like he secretly wanted to stick his throbbing cock into that same tight hole and use that tightness to help his fat cock cum. It's not like he secretly wanted to fuck his wife's grandmother's hot ass and take pleasure in her mature flesh. Right?

Derek pushed himself off from the headboard and got on his knees behind Helena. His cock bounced around in the air as he did, and as he got behind his wife's grandmother, his cock literally came to a stop when the fat tip of his cock wedged itself between her firm ass-cheeks, pointed directly at her asshole.

Despite Helena's earlier assertion that this was not supposed to happen, fate was giving him a sign. Maybe time and space and fate wanted him to fuck his wife's grandmother.

Maybe time wanted to be conquered.

Derek tentatively propped his hands on her hips and squeezed lightly. His dick was leaking his juices, desperate to move forward and enter Helena's asshole. Derek looked up at Heather, having a moment of hesitation. But Helena would not suffer any delays. Looking at him through the mirror, she caught his gaze.

"Do it!" she spat out. Sighing lightly, he readied himself behind her. Unsure if he would be able to force his thick meat inside her, he nonetheless flexed his strong arms and began to push forward, trying to force his meaty shaft into her.

Helena winced as the cock pressed against her asshole, which was unyielding despite the earlier warm-up. Her whole body was forced forward in response.

"Do it, Derek! I can take it! Just be a man, be a good husband, and force your cock up your wife's grandmother's tight asshole!" Helena said, staring at him icily through the reflection in the mirror. Derek looked up at her. Looked at her icy expression, and her massive breasts hanging under her. Derek gripped her hips with a renewed effort and began to push forward again.

"Hnnnnnnn, if you get that fucking dick in my asshole, you can do whatever the fuck you want to my big tits!" Helena groaned out, noting his earlier glance. Derek didn't respond. He only pushed and flexed harder, trying to bury his cock in her sweet ass just to get the privilege to play with her massive tits again.

Helena studied the young man. His fitness had never been more clear to her. All his muscles were flexing, trying to get that fat cock of his inside of her. His firm muscles on his fit arms... the sweat dripping down his firm abs. Her eyes consumed his body lustfully, and for a few moments, she almost lost her composure and reverted back to her younger self, eager to have the hottest piece of meat she could find. Eager to jump his bones and ride his fat cock to endless orgasms. Helena recovered quickly, not showing Derek this momentary loss of control.

"C'mon Derek, I thought you were strong! A big strong guy like you should be able to force his cock into an old lady's asshole!" Helena taunted. Derek's body flexed as he tried to force his cock inside of her. She pushed back forcefully, attempting to help this process move forward. Derek's face scrunched up with effort.

"Do it, Derek! Do it!" Helena demanded as she felt the pressure from the tip of the young man's dick trying to invade her backside. "C'MON DEREK, DO IT! FUCK MY ASS! FUCK YOUR WIFE'S GRANDMOTHER'S ASS!" she screamed out.

Finally, the tight asshole allowed entrance. Once the dam broke, it eagerly spread open around the pulsing tip, quickly smothering it in her tight asshole. With the force at which he was pushing his dick inside, once her asshole opened up and allowed entrance about four inches of the thick shaft followed.

"AHHHHH! THAT'S IT! THAT'S FUCKING IT!" Helena moaned out in pleasure.

Derek's eyes widened once he realized he was now inside Helena's ass. Once he realized his thick meat was quickly being consumed by his wife's grandmother's hungry ass, he slowed his descent and allowed himself to savor the pleasure.

Obviously, he had never experienced anal sex before. And now, here he was, his thick shaft buried in his wife's grandmother's asshole, and he had to wonder how he got there. How had he reached the point in life where he was not only cheating on his wife, not only cheating with his wife's grandmother, but fucking her in the ass? Feeling the way her tighter than tight asshole stretched around his throbbing shaft. Feeling how her ass muscles were already working his dick over, smothering it with tightness and pleasure. Looking at the sight of her full ass-cheeks spread apart and his large cock somehow impossibly stuck inside her small butthole.

He looked forward to the mirror in front of him and took in his own image. The image he saw looking back at him was alluring. He was looking at a different person.

Even as Derek grew into an adult, he had always felt like a kid in adult's clothes. Even during his courtship of Heather and the wedding, he felt was just acting the part of an adult, doing what adults do. He looked at the people around him, the actual adults, and he just marveled at how self assured and confident they were. How adult and well put-together they were. Derek felt like he was just pretending to be an adult and hoping no one would notice. And even when he made love to Heather, it wasn't the love-making of a confident adult. It was the unsure, shy caresses of two people playing a role neither were ready to play.

So as Derek looked at the mirror, studying the dizzying tableau there, he admired it objectively, as if it wasn't him and Helena in the reflection. He didn't see a boy. He saw a man. He wasn't playing the part, dressing in the clothes. He was a man, and he was doing what men do. He was fucking a woman, a voluptuous, sexy, mature woman. And what he was doing was not unsure love-making, but forceful, almost confident fucking. He admired his own fit form in the mirror, and he had to admit he looked pretty impressive. He looked like a model. Or a porn star. The type of guy you want to watch having sex. And the woman in the mirror, the woman he was fucking, she held up her end of the bargain.

Looking at her nude frame, her elegant but filthy face and massive hanging udders, any objective viewer would think she was a porn star. Not a typical porn star, but one of those filthy older lady porn stars, those MILFs. And she was not one of those jaded women who stayed in the business far beyond their prime. No, the woman in that reflection is one of those mature porn stars who stays in it because she loves to fuck and she is still at the top of her game. That mirror wasn't a mirror anymore. It was a television. A television playing the filthiest porn imaginable.

Helena was thinking the same thing. A voluptuous mature woman with a fit stud behind her, dick deep in her asshole, it was not an unfamiliar site to the porn-addicted grandmother. She had seen a lot of this very thing, and footage of this was lining her shelves. She had always admired how those sexy older women had used their bodies to turn young men into fuck-toys. And how brazen and confident they were to show this fact off. She had utilized her many connections to get a hold of some of the highest quality porn out there. It was not the mass marketed stuff you find on shelves. No, this was stuff only shared among the elite. A secret society of older women eager to show off how many hot young guys they had sunk their claws into. In it was fucking so rough, beastial and brutal that it would scare the weak-hearted off. But once you saw it, you couldn't get enough. That shit was addicting. High-class older sluts getting railed by gorgeous young guys. Anyone watching would want to get some of that sex as soon as possible, and add to the porn collection circling the globe. Some of these videos would even 'accidently' end up in the hands of some prospective studs this society had their eyes on. They would no doubt watch this stuff, curious of its contents. And needless to say, after a short time, footage of these same guys in the arms of an older woman would soon be in the hands of this society.

Helena was not afraid to share footage of herself, but she never had. She was too much of a perfectionist. If she was going to share to the world her hot body in action, she would make sure the sex within would be so incredible, so pitch-perfect that no one could deny her superiority. It would be a mythical porn, sex so good that the viewer could not stop watching, eyeing up her hot body and desperate to find out her identity. The thought made Helena smile.

She had dreamed of this for a long time. Rough, brutal sex, with someone now within her own family tree. Sure, he was not related by blood, but the fact that he married her granddaughter and still fucked her made up for that. She vowed to make this sex the best she had ever had. She vowed to make her dream a reality. She promised to make the world shake.

Now, if only this sex was being recorded. She thought for a moment, before remembering that nosy hotel clerk, and how eager she was to get close to Derek, and how she had been the one to prepare the room for the married couple. She had a thought. Helena's eyes circled around the room, but the thought faded away for the moment as she felt the thick shaft shift in her asshole. Her focus returned to the here and now.

"Oh, I think you can do better than that." she taunted, looking back at Derek, and at how he had only some of his thick shaft inside her.

"Can you take any more? I mean, I have a lot in you already." Derek asked. Helena smirked.

"I'd say you have about four inches in me so far." Helena estimated. "Make it ten." she finished, turning around to face the mirror. Derek paused. "C'mon Derek, do it! Fuck my ass Derek! Give me everything you've got!"

Derek got a little angry. He focused his mind, grabbed her hips, and began to push. Slowly but surely, her asshole accepted more and more of his throbbing prick inside her. He looked down to see the smooth flesh of his unblemished dick enter her hotter than hot ass. The surrounding, creamy mature flesh added to this vision.

He was amazed as he felt the tip of his dick go deeper and deeper inside. He looked up into the mirror and saw the cold eyes of his wife's grandmother staring at him, unfazed, daring him to make her react. Daring him to make her moan.

Derek still had a few inches left. Sneering a bit, Derek reared back, and...

"AHHH FUCK YES!" Helena screamed out in pleasure. With one heroic thrust, Derek had buried the remainder of his large cock deep into Helena's asshole. "That's it Derek! That's fucking it! That's how you do it! That's how a man fucks!"