Valentine's with Jackie - Part 4 (Patreon)

“You ready?”

Denver was positioned at the entrance to Jackie’s vagina, his legs firmly in Aliyah’s grasp as she teasingly traced the top of his head around Jackie’s labia. She was grinning down at him as she asked the question, but the smile was the furthest look from friendly that it could be. Denver, with his heart beating so much that he was nearly shaking, had his mouth and eyes clamped shut; he wasn’t bothering with a response, and Aliyah wasn’t really waiting around for one anyways. For a moment there was a pause, as she lined his head up with Jackie’s pussy, and then came the push inside.

From the very first push, Denver was inserted into his sister all the way up to his waist. His naked body slid against her slick interior with uncomfortable snugness, rubbing back and forth as Aliyah worked up a rhythm. He was doing a successful job of keeping his mouth closed so far, but it had only been a few seconds. And what he wasn’t tasting, he was still smelling plenty of. The smell of Jackie’s sex had a distinctive sharpness to it; he had the thought of how much better it was to smell than her asshole, but he immediately berated himself for sounding like it wasn’t that bad. It wasn’t the smell itself that was so horrid, it was the fact that he was inside the most intimate and private part of another human being—without the “protection” of a dildo like he had the first time. But it wasn’t just anyone. It was his sister. And she wasn’t even trying to do anything about it as her vagina slowly expanded and he gradually got pushed a little bit deeper with every thrust.

Aliyah, on the other hand, was ecstatic. She practically felt glad that her boyfriend had broken up with her just because it had led to this moment right here. She didn’t truly hate Denver, but he could always be relied on for an entertaining response to her ridicule, so she’d never seen the point in stopping. But this was the ultimate form of teasing; it wasn’t even teasing, really, it was so much further than that. Getting to stuff his squirming body up his sister’s cunt gave her an electrifying feeling. But she had the added bonus of being able to imagine that Denver was actually her ex, and that she was punishing him for how cruel his breakup had been with her. Once that image was in her head, it set ablaze a fresh wave of fire within her; she squeezed Denver’s legs a little bit tighter, made her thrusting motions a little bit harder, and started pumping a whole lot faster.

Jackie hadn’t planned on starting anything sexual with her friend, but she wasn’t surprised at what the afternoon had evolved into. When she and Aliyah had first met, they’d been just friends, but at some point in high school their relationship got a little “with benefits” suffix added onto the title. Jackie still considered herself (mostly) straight, but Aliyah was one of the few people that brought out the bisexuality in her. Her most romantic encounters had been with guys, but the majority of her most sexually pleasing ones had been with women. Nobody knew their way around Jackie’s body like someone of the same sex. But even more, nobody knew their way around Jackie’s body like one of her best friends.

After spending a few minutes gently playing with Jackie’s clit while pumping Denver in and out, Aliyah glided her body across Jackie’s, her head hanging over her friend’s for a moment as they both smiled at each other, before leading into a kiss. Jackie was fully receptive, and returned the kiss as she held Aliyah’s head with one hand and began feeling her friend with the other.

Now that a few minutes had passed, Denver could no longer say his mouth hadn’t opened. Not by choice, of course… well, kind of. The friction of going in and out so quickly was nearly suffocating when just breathing in through his nostrils (not to mention that Jackie’s fluids would often seep inside his nose anyways), so he’d had to open up his mouth occasionally to try and take in air. It would mean tasting Jackie’s pussy every now and then, but at least it allowed him to stay conscious. Even if he was about to pass out or die for some reason, there was no reasonable way that he could let them know. He could struggle with every bit of strength he had, and not only would both girls just assume it was him physically complaining of his discomfort, but it’d probably turn Jackie on even more.

After a few more minutes of making out from the two girls, all while Aliyah made sure to pump Jackie’s brother in and out at the perfect speed, Jackie gently motioned for her friend to retreat so she could sit up. “You’re up next,” Jackie told her friend, taking Denver’s feet from her (since that’s how far he was buried by now) and pulling him out. “I’ll give you a moment to catch your breath,” she whispered to her brother, wiping her juices off his face while watching Aliyah undress.

“I can barely breathe, there’s no room to breathe. I almost suffocated,” he pleaded, genuinely fearful that his predicament might get worse with the smaller girl he was about to enter.

Jackie sighed and grimaced; she didn’t like when Denver guilt-tripped her for stuff like this. But like she said earlier, she didn’t wanna hurt her brother. Punishment was different than pain. “Alright, I’ll let your head stick out,” she told him quietly. “Probably everything from your chest up actually, she’s kind of a bit smaller than me down there.”

“What’d you say?” Aliyah asked, not having heard their conversation. She was fully naked now though, and ready for her turn.

“Nothing,” Jackie shrugged, and then got onto her stomach in between Aliyah’s legs started pushing her brother inside, this time with his feet first.

Immediately, Denver’s suspicions were confirmed: Aliyah was noticeably tighter than his sister. He didn’t even think he’d be able to wiggle about as he got slid up to his waist. But at least Jackie was going slower with Aliyah than her friend had with her; despite Aliyah’s fiery personality, she was always won over by a softer touch. Once her insides had stretched out a bit more, Denver was able to get in up to part of his torso, just like Jackie had said, but before he could feel relieved about how much less precarious his situation would be, he found his head suddenly get enveloped by a different kind of wet lips.

Jackie had perched herself on top of Aliyah’s body, so that her friend’s head was between Jackie’s legs while her head was between Aliyah’s. Somehow Jackie was operating with an unusual amount of prowess as her mouth not only enveloped her brother’s upper body, but her tongue stuck out so that she could dance it across Aliyah’s bits in addition to using Denver’s body to stimulate her. So even though Jackie’s tongue was on the bottom of her mouth, she was able to tickle it against Aliyah’s clit since her head was upside down. Her brother’s neck also ended up providing a good cranny for her lips to seal around too and get a good grip on Denver, allowing her to continue slowly pumping him in and out while suckling on his head.

Despite all this, and to her brother’s surprise, Denver found himself still able to breathe. Because her lips had closed themselves beyond his face, his head was cushioned on the pillowy inside of Jackie’s lips. He was breathing the humid, recycled air that was inside her mouth, but it was still air nonetheless.

Aliyah, who had been working her magic on Jackie at the same time, from the other end, was eventually able to bring the girl to an orgasm, which made Jackie’s muscles suddenly tighten from a mixture of pleasure and surprise. After recovering, she crawled off her friend and collapsed onto her shoulders, gazing at her friend dreamily with a drunken smile on her face. Aliyah reached down to continue where Jackie had left off, but was surprised to feel the nub of Denver’s head sticking out instead of his feet. She hadn’t even realized that Jackie had stuck him in the other way around.

She sat up at a weird angle so that she could look at Denver, raising an eyebrow. “I didn’t know your head’s been outside the whole time,” she spoke down to him, while he struggled to maintain eye contact with the giant girl’s head looking down at him between her legs. She fished him out, but only so that she could turn him around and line his head up with her sex, just like she’d done with Jackie. “I want you to know that you’re inside of me. All these years of being on the receiving end, despite being older and bigger than us. And now look at you. You were always bottom level, and I’m glad I could be the one to remind you of that. But now it’s time to go even deeper.”

To conclude her mini-speech, she rammed his body so deep inside of her that he nearly hit his head on her cervix. Trying to breathe and operate inside Jackie had been one thing, but Aliyah was so much worse. It was so much tighter, and her inner musk was a bit more sour. It was as if the experience had instantly injected him with an evolved form of claustrophobia, and he was so desperate for room that he tried pushing outwards with his arms to give his head just that extra little millimeter of room if it could manage.

Aliyah gasped, not only from feeling Denver get re-inserted, but his squirming arms moving around inside of her brought her experience to a new level. Jackie, seeing her brother’s predicament, rushed forward to save him and pull him out, but not after Aliyah had gotten what she wanted. Denver had spent over a decade hating her for how she made him feel over the years, but with just a few seconds, she’d achieved a new level of unfair depravity that he’d never be able to compete with. Complete power and control.

Jackie pulled him out and chastised her friend for being too rough, but Aliyah didn’t care. She’d gotten her fill. Denver had never gotten the upper hand with her, and now that he’d been shrunken down and nearly choked while buried up her cramped, wet pussy, there was nothing he’d ever be able to do for the rest of his life that would match the total domination she had had over him in that moment.