All Night Long (Original Modern)

(Every character depicted in the prompts below is a consenting legal adult over the age of 18)

Poll Winner

Themes: Marathon Sex, Loving Sex, Breeding

Summary: After a bad breakup, Jesse's only comfort is his friend, Jolene. What he doesn't know, is that she's been trying to get his attention for quite some time, to the point his now ex even told her multiple times "Don't take my man." Now, she's more than ready to show him that his heart will go on while making him feel free as he'll ever be.

-x-X-x-

“Jolene…”

Her name leaves his throat in a sonorous groan as her hand down his pants slides over his cock. Jesse shudders, not just from her silken smooth palm on his member, but also her large tits pressed against his chest as she smirks up at him from her slightly shorter height.

“Shhh… let me show you how much I care about you, Jesse~”

With a slight push, Jolene sends him back into the chair behind him. Jesse sits down heavily, watching through hooded eyes as she stands in front of him. There’s no doubt that Jolene is all woman. Clad in a form-fittingly tight sweater and jeans, she smirks as she runs her hands along her own form for a moment… before dropping to her knees in front of him.

“I’m going to make you feel so good~”

Her hands come down on his knees and then slide up his legs to his crotch. Jesse’s breath hitches… but he doesn’t doubt for even a moment that she’s telling the truth. More so… he needs this and he knows it. The last week or so has been fucking hell and Jolene is promising him a light at the end of the tunnel, a respite from all of his heartbreak… how can he not reach out and take hold of that with both hands?

Jolene deftly yanks down his pants and boxers, having already unbuttoned and unzipped the former before stuffing her hand down the latter to feel him up in the first place. Jesse’s cock, half hard and quickly growing bigger, comes flopping out into open air, twitching and thickening as he hardens up more and more by the moment.

Eyes alight with excitement and pleasure, Jolene licks her lips and then leans down to run her tongue along the underside of his cock, all the while staring up into his face as she goes. Jesse shudders, one of his hands reaching out almost involuntarily to slide his fingers through her curly hair.

If someone had told Jesse even a couple of weeks ago that he would be doing this with Jolene, he would have probably punched their lights out. After all, Jesse was loyal… and two weeks ago, Jolene had NOT been his girlfriend.

No, that had been Mary Anne, the woman that Jesse had fully believed was the love of his life. Unfortunately… Jesse’s best friend Micky was after Jesse’s girl. He’d taken her by the heart when he took her by the hand and Jesse had been forced to watch his Mary Anne walk away from him.

All of this had happened a few days ago and Jesse had been wallowing ever since. His only comfort during this time had come in the form of another friend of his… Jolene. She had his back in a way no one else seemed to. She was the only one in his life who assured him he wasn’t crazy for feeling betrayed by both Micky and Mary Anne.

Everyone else wanted him to just accept it. That ‘love was love’ and there was no helping any of it. But Jolene… Jolene didn’t want him to accept it. She wanted him to move on, not for Micky and Mary Anne’s sakes, but for his own sake. She didn’t want him to forgive or forget… she just wanted him to put them both behind him and find a way to be happy again.

Jesse hadn’t been sure that was possible… until Jolene made her intentions about how she was going to MAKE him happy again abundantly clear. And now here they are, with him sitting back while she licks and laps at his cock, swirling her tongue around his glans and sliding it all around his member.

He lets out a groan as this continues, shuddering in pleasure. Just when he thinks it can’t get any better than this, Jolene suddenly pulls back, eyes flashing with impish excitement and lips curled in a mischievous smirk. Then, right before his eyes, she shucks off her tight sweater, yanking it over her head and letting her breasts bounce free.

She has no bra on, meaning that her large, pale tits are fully exposed after she tosses the sweater to the side. Bouncing and jiggling for a few moments until they finally come to a quivering stop, Jolene kneels there for a moment, framing her tits by crossing her arms under them so that Jesse can see them properly.

Then, still grinning all too wickedly, Jolene sits up and leans forward, promptly wrapping her breasts around his now fully erect cock. Jesse gasps from the sensation of such soft, pillowy tits wrapped around his dick. He groans, even as Jolene moans, her lips forming into a small ‘o’ as she begins to glide along his member.

“Like that, Jesse? Do you like having my big, beautiful breasts wrapped around your cock?”

“Fuck Jolene… you know I do…”

Jolene giggles, eyes shimmering with glee.

“That bitch Mary Anne always told me to stay away from you. But now she’s the cheater. Now she’s the cunt who left you. She doesn’t know what sort of man she abandoned… but I do. I know how special you are, Jesse. And I’m going to show it to you… all night long~”

All night long. Jesse shivers in anticipation from that promise. He believes her after all… and quite frankly, he believes he could go all night long with a woman like her. After all, there’s simply no beating that beautiful, bountiful body of hers~

Leaning forward as his cockhead pokes out from between her tits, Jolene continues to smile even as she wraps her lips around the bulbous tip of his dick. She sucks and slurps away some more, all while sliding her breasts up and down his shaft. Making out with his cockhead gives Jesse no end of pleasure, driving the young man absolutely wild as he tosses his head back with a groan.

“Jolene! Fuuuck, Joleeeene!”

She sucks even harder as he groans out her name, hollowing out her cheeks and tonguing his glans like she’s tongue-kissing him instead of his cock. Until finally, with a louder groan than ever before, Jesse tips over the edge and begins to cum.

“Here it comes, Jolene!”

His warning does not fall on deaf ears. Jolene is ready for him, staring up into his eyes even as the first spurt of Jesse’s seed hits the back of her throat. She starts to swallow and never stops, gulping down Jesse’s load like there’s no tomorrow and guzzling it until his balls have emptied… for the first time, anyways.

The moment he’s done cumming, Jolene lets her tits fall away from his cock and begins to bob up and down his member even harder, turning her swallowing into a proper bit of fellatio that keeps Jesse from ever fully going soft. And as soon as she ensures he’s staying rock hard and is ready for another round… she pulls back off of his twitching, throbbing cock with a pop and looks up at him hungrily.

In an instant, she’s up on her feet, her breasts bouncing and jiggling some more as she reaches down and unbuttons and unzips her own jeans, peeling herself out of both them and her panties. Jesse finds himself entranced by her shimmying, right up until she’s turning away from him to bend herself over the nearby dining table. Then, he finds himself entranced with her big round ass, peach-shaped and revealing a glistening wet pair of pussy lips nestled between her thighs.

“Well Jesse? What are you waiting for? I’m certainly not going to hold out on you like that bitch Mary Anne. What you see is what you get… literally. Any time, any place, you can have me however you want me~”

Such a promise… Jesse rises to his feet, mouth paradoxically both wet and dry as he moves towards Jolene’s bent over body. He kicks off his pants and boxers as he goes, shucking his shirt over his head for good measure as well.

By the time he stands behind Jolene, he’s down to just his socks… and he definitely doesn’t have the care or the patience to shuck those off before reaching out and grabbing Jolene by her hips. Instead, he leaves the socks on and focuses on the matter at hand, her gorgeously wet cunt waiting for his throbbing, twitching cock.

“Jolene… once I start fucking you, I’m not sure when I’ll stop…”

Looking back at him, Jolene giggles.

“That’s what I like to hear, Jesse. Don’t hold back~”

Well… fuck it then. Mary Anne was gone. Micky was a damn traitor. Jolene might be all he had left, but Jesse certainly wasn’t complaining about that. With a grunt, he thrusts forward and impales his new girlfriend on his cock, stuffing her full of his dick right then and there.

Jolene cries out, arching her back and going up onto her tiptoes as she leans forward on her forearms. Her ass lifts, providing him with easier access as he drives deep into her pussy from behind. And Jesse… Jesse doesn’t stop there. He’s not going to hesitate. He’s not going to slow down or wait. Not if she’s not asking for it.

PLAP! PLAP! PLAP!

Jesse sets a punishing pace right off the bat, one that has Jolene moaning and squealing right alongside the obscene noises of flesh slapping against flesh that fill the room. She shudders and shakes, the table rocking under them both… but not once does she ask for him to slow down or wait for her to adjust. In fact, it’s pretty much the exact opposite.

“Yes! Harder, Jesse! Don’t stop! More, please! Oh god, oh fuck, YES!”

Her impassioned cries and begging for ‘more, more, MORE!’ is like music to Jesse’s ears. His and Mary Anne’s relationship hadn’t been entirely frigid of course, but damn if she hadn’t been pulling away from him in recent months. Now he can’t help but wonder if that was because she was already with Micky…

But either way, it’s just nice to be desired again. Emphatically and enthusiastically desired at that. The more Jolene begs for it, the harder Jesse fucks her, until eventually she’s squealing and shaking under him, cumming all over his cock and orgasming explosively for him.

At first he worries he’s hurt her in some way… but she keeps asking for more even as she climaxes upon his prick, begging for it at the top of her lungs. And so Jesse keeps going, keeps giving her more… until he can feel a familiar tightening in his balls and knows that he’s getting close to the point of no return.

“Fuck… Jolene, I’m gonna cum!”

“I-Inside! Pump me full, Jesse! I want it! I want to be your baby mama! I want to carry your children!”

Jesse’s eyes widen as his cock surges at her words. That was one of the biggest sticking points of his and Mary Anne’s relationship… he wanted to start a family, but she wanted to wait a while longer, despite them both being adults and him having a good paying job. She’d always said they would do it eventually but…

In a fit of pique, Jesse slams forward into Jolene one last time and groans as he lets loose right into her womb. Unleashing his load, he paints her innermost sanctum nice and white, coating every inch of her insides with hot, thick, virile seed. He cums for what feels like an eternity before he’s done, panting heavily as he nearly collapses on top of her.

Jolene, meanwhile, gives him a moment to recover before bucking her hips and pushing him back. As he stumbles, she’s already turning around and descending back to her knees, grabbing him by the ass to hold him steady as she takes his cock back into her mouth and begins to suck him clean.

Except… she’s not just sucking him clean… no, she’s getting him nice and hard again, bobbing up and down until he’s ready for a round THREE of all things. Once she’s done, she pulls back and smiles up at him coyly.

“If we want to be sure the seed takes… then we really do need to go all night long~”

Well… Jesse can’t argue with that, now can he? Swallowing hard, he nods.

“Right… all night long.”

Suffice to say, that’s precisely what they do. They fuck the night away, with Jesse delivering every single load except for the very first directly into Jolene’s womb… and the beautiful buxom woman happily accepting all of them into herself as they share a lover’s embrace.

At long last, they’re finally together. And there’s nobody to stand in their way.

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Google Doc Link: https://docs.google.com/document/d/1l8y3JjmjeCzAAx_ON1IaRIwqf9un75BMrhN-nGDj1zE/edit?tab=t.0