The Daily Life of a Free Use Sister

"You know, your lips feel absolutely wonderful," said Jayden.

Holly said nothing, still seated with her knees pressed against the soft carpet of the floor.

"And the way you use your tongue," he continued, "Nothing at all like what happened during your first time. You know, with the teeth and all."

Holly scowled at him again, her face perfectly blank despite the precum rolling about in her mouth. There was no way she didn't remember, but it was hardly as if she was going to let something like that show. Even if it had taken place the day after her sentence had been declared, and would have ended with just that if only she had the dignity to resist biting down.

A blowjob, that was all he had wanted after an entire decade of being bullied by her. And would have been happy with as well. Only except with one thing leading to another and his dick feeling rather abused, it wasn't long before she was standing naked in front of him with a marker shoved up her ass while he teased her nipples over and over again without ever once letting her go over. Then, by the time he finally thought to let her go she was practically begging him to fuck her instead, and the rest simply followed. A brief tussle in the sheets with her still sobbing from the frustration, and it wasn't long after he had emptied himself into both her holes with the two of them lying there together in bed that their newfound relationship had started to grow. All the way up to where they were now.

Jayden smiled as he looked down. The room was so quiet he could practically hear her breathe. One last swipe of his cock across her lips, and Holly sighed as he waved for her to stand back up. Biting down on her lips as she walked over to lay down across the bed, she wrapped her arms underneath the hollow of her knees as she slowly drew them up against her chest. Spread out in front of him like this, every last inch of her most intimate place was laid bare for him to see and tracing his fingers around the very edges of her slit, he watched as the tiny little nub hidden underneath her hood start to twitch.

Seventy-three to one. Better luck next time, he supposed.

"Excited?" he asked.

Holly grit her teeth.

"Are you sure you don't want something to hold onto down here?" he asked, "A finger perhaps? Or maybe a pencil or two to squeeze down against while you wait for me to finish?"

"Only if you agree to shove the same up yours," she said flatly.

Well now, how nice of her to consider his feelings. Unfortunately for her though, that was a bit outside his realm of expertise. As such, another brush across her labia, and he smiled as she tightened her grip. Following that, it was a simple enough matter of spreading her labia apart with his hands to tap against the opening of her entrance below. A perfect little donut of pink that practically begged for him to stick his fingers in, and against the several month-long period of denial built up within, it was all but impossible for her not to flinch.

"Jayden...!" she gasped.

"I'm listening," he said.

"You promised I could pick!" she said.

Tap... tap... tap...

"So I did," he said, "Your butt today, wasn't it?"

"Then hurry up and get it over with already," she snapped.

She squirmed, shaking her hips about as she tried in vain to escape, and he laughed as the movement only caused her legs to spread themselves even wider so that he could see both her holes. As fun as it was to continue teasing her like this though, it could hardly be said that he didn't also keep the promises that he made, and so with one last pinch across her clit he stepped forward to press his member against the opening of her anus. For a moment the muscles of her ring almost seemed to resist, pushing back against his glans even as they slowly stretched apart to swallow him whole.

The passage was painstakingly sedate, but he pushed on. Little by little though, he started to make progress with the arousal trickling down from her entrance above helping ease the insertion. One inch, and then another, each one claimed with a careful precision angled in just the right way to press up against her g-spot through the thin barrier in between, and trapped underneath him by his weight, Holly gasped as she felt the sensitive skin of her flesh stretch around his dick. So warm, so tight! Like a soft furnace of tightness to bury himself in.

Then, at just a little over halfway through, the pressure finally broke through as the hair-trigger response of her body finally took over, reluctantly pulling him into the searing heat of her all too welcoming depths.

"Oh...!" she said.

Oh was right. Instantly, her legs closed around his waist to draw him close as her pussy started to twitch. Not that it would help her much against the emptiness, but the effort had to be worth something at least. For a moment the two of them stood there like that, him doing his best to stay still while she whimpered against the frustration of having his dick filling up her rear. It was hard not to cum right then and there. Through sheer power of will, however, he managed to keep himself in check and after waiting a couple more seconds for her to get used to the feeling, he slowly pushed himself forward to bottom all the way out before withdrawing to repeat the process once more.

The tightness was beyond anything he could imagine. Up above, Holly moaned as her clit stood up even further into the air. Biting down on her lips, she pulled against the sheets as another trickle of crystal-clear fluid seeped out from the parted opening of her entrance to flow down to the place where they were connected, and she whimpered at the increased sensation of friction.

"Feels good, doesn't it?" he teased her, "Almost like you're about to hit the edge?"

Still lying there on the bed, she closed her eyes tightly as she tilted her head back.

"Bet you wish you took me up on my offer before we got started," he continued, "Well, it's not like you have long to wait. Just think about it. Tomorrow, you'll get to enjoy every last bit of my dick filling up your pussy instead of just your rear, and I might even be nice enough to touch your clit. A shame you won't be able to properly enjoy it. Given how tight you are down here, I can't even imagine how good it would feel once you're finally allowed to finish."

Maybe she was listening, maybe she wasn't, but there was no mistaking the way her nipples started to stiffen on her chest. Holly whimpered again as the walls of her rectum clung desperately to the entire length of his shaft. Already the thrusts were starting to become easier as she opened up against the intrusion, and slowly he felt himself sliding deeper and deeper into her rear. Pulling himself out of her again, he smiled as he felt her clench. Every time he spread her apart, it was obvious to see just how much she wanted to react, to cry out against the frustration as the tight opening of her anus slid smoothly over the sensitive tip of his glands. And were it not for the wonders of technology, she would have probably already climaxed a long time ago instead of being forced to hold it in.

The thought was next to intoxicating. An entire year of being able to use her as he pleased, all while she was unable to do anything except endure the desperation of being denied like this. Panting, he thrust himself one last time into her rear. Against the pleasure running through his veins, it wasn't long before he reached his own peak and as the pressure in his prostate finally broke through the limits of his endurance, he grunted out loud as he came.

"Oh," he gasped, "Yeah, that's it. Take it all."

Holly threw her head back, her legs spread wide apart as he pushed himself all the way forward until her hips were pressed up against his. Still trapped underneath him though, there was little she could do except freeze in place as she felt his member starting to stiffen. It was a cruel reminder of what she was missing as the orgasm suppression device came to life around her clit, keeping her trapped on the very edge of a climax that had to wait until her sentence was complete. Too bad it probably wouldn't even feel like anything with how desensitized her body would be by then, and with her hands trapped by her sides in the middle of the courtroom as the doctor finally took off the ring, there wouldn't even be anything she could do about it as the public security cameras recorded her misery for the entire internet to see.

The stories were common enough that the documents were already starting to be rewritten to account for it. A mandatory ruined orgasm in front of the judge after an entire year of being forced to hold it in. Or perhaps maybe several if the contractions that resulted happened to be insufficient. As such, closing her eyes tightly, Holly sobbed as the first spurt of semen started to flow out into her rectum, the stickiness of the load standing out in perfect contrast to the transparent thinness of her own frustration. A second spurt, and then a third, and Jayden let out a sigh of satisfaction. It was almost as if there was a tiny little sliver of heaven wrapped around his dick, a soft pillow of comfort that perfectly milked him for every last drop of his seed.

A minute passed, and then another as he continued to paint her insides with a thick layer of his fluids. Against the overwhelming sense of pleasure, by the time his dick had grown soft enough to slip back out it was almost as if his head had been wiped blank. Slowly sitting up again, he looked over at his sister as she continued to sob with her clit still rock hard at the top of her slit. Buzzing softly from the aftermath, the orgasm suppression gave out one last pulse as it finally fell silent.

"Satisfied?" he asked.

Holly groaned as her pussy let out another twitch. Reaching out to give her a gentle pat across her head, he picked up a tissue to wipe away the leftover remnants of their combined fluids. Then, grabbing his school uniform from where he had left it beside his desk, he walked over to the bathroom to shower and get dressed. She would probably join him a couple minutes later once she had recovered enough from the fucking, but for now it was probably fine to just leave her like that.

Stepping through the door, Jayden looked back one last time over his shoulder. Still played out across the bed, Holly rolled over to prevent his semen from leaking out against the sheets. Between her legs, her pussy peeked out at him, the swollen lips of her labia completely soaked through with the frustration of her recently suppressed climax, and he felt his dick rise up at the thought of using her again later in the evening.

That was for later though. Turning away, he smiled to himself as he went to wash his hands in the sink. Out of all the people in the world that he could have been paired up with, truly, he must be the luckiest person alive to have a sister as nice as his.