Christmas with Jackie - Ch. 6 (Patreon)

Jackie shimmied out of her panties with one hand, while her other hand held snugly onto her brother’s body. Kicking the underwear aside, she climbed onto her bed, clearing a space for herself so she could be most comfortable. Then she sat down, her back resting against some pillows she’d propped up against the headboard, and deposited Denver in between her spread-out legs.

He looked up at Jackie’s sex, standing loud and proud in front of him. There was a decent amount of bush above it, although she seemed to keep it relatively well maintained and clean at least. He was standing around 20 feet back from his perspective, which really gave him the ability to observe it in its entirety. But just the fact that he wasn’t even as tall as her private parts was enough to get his heart racing again, agonizing over what was just moments away.

“I know this won’t be very easy for you,” she said. “Obviously it’s gonna be a bit awkward for me too. But it has to be done.” She looked somewhat sympathetic, like a parent about to discipline their child. “So I’ll give you a few moments to get yourself ready,” she added, “or in the right headspace or whatever. Plus I need a few minutes to get my body ready too.” She didn’t wanna be looking at him anymore for this next bit, so she lay her head back and closed her eyes as she stuck her middle three fingers in her mouth to suck on. After a few seconds, she took her hand out and slowly guided it downwards, starting to gently massage the top of her vulva. Denver couldn’t bear to watch it either, and turned away, as Jackie gradually picked up a bit of speed, working her way to her clit and being careful not to go too fast. She was taking deep breaths in and out, imagining a couple celebrities, a guy from her work she thought was cute, even one of her exes. But she couldn’t get Denver out of her mind. Not him specifically, but the idea of him, the sight of him being so small and helpless. She didn’t want to think of it, but she couldn’t help it.

After a few minutes, Jackie felt like she was ready, and opened up her eyes again to look down at her brother and pick him up with her other hand. His eyes flashed open too as he was suddenly lifted upwards and turned around to face his captor. “So I was gonna just stick you inside,” she said, grabbing the dildo and holding it bottom up beneath Denver. He looked below him at the deep and hollow shaft, and started squirming uncomfortably, wanting more than anything in the world for this whole experience to be over. “But then I realized it might get annoying cuz you’d be bouncing all around. So if you want, I wouldn’t mind taping you down or something. The important part is that you’re inside.” She said it all so disturbingly nonchalant. Minutes away from stuffing her older brother up her pussy, and she was explaining the whole situation as if she was simply talking about her day. It left him speechless, and his mind was still trying to process what was about to happen. There was a moment of silence as she waited to see what he’d say, but he was frozen in fear. “Well I’ll take that as a ‘no’ then,” she sighed. “See you in a little bit!” And then he was dropped into the hole below.

Denver landed with a soft thud at the curved bottom of the dildo—which luckily hadn’t hurt his durable body. Everything around him began moving as Jackie set the dildo on its side, causing him to tumble a bit until it felt like he was in a long corridor instead of a deep well. It began moving, and outside of the air holes he could see the sides of her thighs, until the dildo bumped into something. And then began pushing. With a bit of resistance, it kept going forward, a soft squishing sound coming from outside the tip, causing Denver to hyperventilate. It was happening. The awful, unthinkable nightmare. True to her word, he was finally being pushed into his enormous sister’s giant, hungry cunt.

The air holes near the tip got blocked off as she pushed it inside of her, and the inner walls of her vagina slid along the shaft’s exterior, welcoming their guest. Denver felt horrified as a shadow fell over him, and a tangy smell started to fill his cave. He got onto his feet and turned to run towards the back of the dildo; he knew he couldn’t escape, but staying near the back would be less traumatic than remaining up front, where it was deepest, darkest, and the smell was strongest. But Jackie had to pull the dildo out a little bit, which made her brother trip. Another push inwards, and then a retreat, as she gently coaxed her vagina to get bigger. Unable to stand anymore, he crawled towards the back in desperation.

But after a particularly lengthy withdrawal, a sudden shove inwards caused Denver’s nude body to tumble forward, but he tripped too far and ended up running into the hand she had covering the exit while gripping the base. Realizing that Denver bumping into her hand meant that he’d been staying near the back, Jackie rolled her eyes; “Fine, if you’re still trying to resist, I guess I’ll just have to be extra about all this,” she muttered, and rotated her body to face the wall while lifting up her legs and laying on her back. As she scooted forward, she set her feet onto the wall for balance, and raised her butt off the bed so her crotch could point upwards like her upper legs. It obviously was a bit of a strenuous position to maintain, so she grabbed her pillow and stuffed it under her hips for support, and then relaxed onto her back, satisfied with her solution to her brother’s reluctance.

Denver had heard what she’d said, but he didn’t understand what she meant until he felt his body jostled about again, starting to slide backwards as she lifted her legs. He grabbed ahold of two air holes just as his prison went vertical, and he heard Jackie sigh contentedly outside. “There, that should be good,” she said to herself, and then resumed with plunging the silicone dick in and out.

Her brother could barely hold on due to the continuous movement. Worse yet, her vaginal fluid was starting to leak into the holes. Including the ones Denver was holding onto. It trickled in between his fingers, but because of the bouncing nature of the hollowed-out dick, he couldn’t keep his hands glued down, so with every bump, a little more of the slippery liquid seeped under his hands. “No… wait,” he frantically said, feeling his grip slipping. “Please!” But Jackie couldn’t hear him. He couldn’t hold on any longer, and he fell back down to the bottom.

His back instantly got wet after he landed, since the liquid that was seeping inside from all around drizzled down into a pool at the bottom. To a normal person’s perspective, it wasn’t very much, but for the two inch tall man, it was easily enough to coat half his body.

Jackie continued pumping him up and down, gaining speed as she rubbed her clit with her other hand. Every plunge would send her toy just a tiny bit deeper, and Denver with it. His body bounced helplessly around inside, every new landing covering more of his skin with her juices.

Jackie’s breathing picked up, feeling herself getting close to the edge. She closed her eyes and took a deep breath as she pulled the dildo halfway out of her, and then with a final push, thrust the rubbery cock so deep inside that it blocked out all the holes and sent Denver into a world of darkness. That final shove proved to be enough for the girl, and her pussy started rhythmically pulsating around her brother as her body relaxed, tired but satisfied, pleasure washing over her body.

Denver was crying in the dark, humid recesses of Jackie’s pussy as she finished; his mouth was clamped shut to keep anything from getting inside, but every inch of him—including his face—was covered with the secretions of his little sister’s most intimate area. After letting the effects of her orgasm wear off, she pulled the dripping wet cock out and turned back around to her former sitting position, giving herself a break but still holding the dildo upright. But she didn’t take Denver out.

He couldn’t even stand up, so he just looked up at the ceiling, and started yelling to get her attention to free him. “HEY! LET ME OUT NOW, PLEASE JACKIE!” His voice was so tiny, but she just barely heard his squeaks and leaned forward, gazing into his cage.

“Sorry about that, I just had to give myself a minute,” she explained with a sigh. “Anyways, you don’t look bruised or hurt or anything, so that’s good. And we’re halfway there!” WHAT? I thought that’d be it! he thought with worrying surprise, as she got onto her knees, carrying him to behind her body. “Done with the front, now it’s time for the back!”