Eventually, Thomas was able to cum. A deep, satisfying orgasm, with his dick surrounded by the soft velvety folds of his sister’s pussy clamping down. Unfortunately for him, however, since there was still some time left before then, that particular account will have to wait for another while. Another couple more months of frustration perhaps, during which he would simply have to put up with the fullness in his balls.
In the meantime though, for the sake of the reader’s interests, there still remain plenty of other stories to tell. Times where he was brought to the very edge of climax by his mother and his sister only to have his member locked back up. Sometimes without even having his dick touched at all.
This story is one of those times.
------
They were down in the living room again. Him, his mother, and his older than him by one year sister Sarah with her ever-permanent scowl. Looking across at her, Thomas couldn’t help but frown. It was the same classic blend of irritation she always wore during their sessions together, painted across her face like a thick layer of makeup. Or in this case, he supposed, a mask of something considerably more off-putting like cracked and peeling drywall. Charming in its own way, and somewhat understandable seeing that she was currently lying naked and bent over the edge of the couch. The only problem was that this time, instead of standing directly behind her waiting to be unlocked, he found himself lying right next to her as well.
“Well now, don’t you two look like peas in a pod,” said their mother.
Thomas wiggled self-consciously, the movement covered up by the considerably louder response of his sister.
“Mom!” cried Sarah.
“Oh hush,” said their mother, “It’s not like it’s your first time.”
“But right next to him?” said Sarah, “Together?”
“Sure,” said their mother, “Why not? It’ll help build character. Also, pout any more with that pretty face of yours, and I might just have to bring out the camera for a picture. You two look wonderful by the way. I really don’t know why I haven’t decided to do this sooner.”
She smiled down at their upturned bottoms, and Sarah groaned in frustration, kicking her feet against the floor. Besides her, Thomas tried not to look at the way her hips stuck out, more for his own sake than anything else. It was Friday, the start of the weekend, and in place of their usual family activities, their mother had opted instead for one of their rare end-of-the-month checkups to determine the state of their health. Which really just meant a prostate milking for him and a g-spot massage for Sarah, along with several rounds of edging for them both. No point in keeping them denied after all, if they had somehow lost the ability to cum. And as awful as that sounded, even he had to agree that it was far better to wait another week than discover that he had suddenly become a eunuch.
For now, though, there was the sharp snap of latex, and Sarah stiffened up. Thomas could hardly blame her. Gloves, he hated gloves. Especially since it never failed to remind him of all the previous times he had gone through this before. Between his legs, he felt his member throb softly into his chastity cage as he bit down. Absent of the usual stimulation, it seemed to be confused on whether it was supposed to be going hard or soft, and had settled instead for a sort of in-between chub that did nothing except remind him again of exactly how long it had been since he had last been able to let it all out. More weeks than he had fingers on his hands, that was for sure, which went a long way towards explaining why even a single glance from his sister was enough to set him off. Never mind the view he had caught of her earlier with her legs parted in just the right way so that the entire length of her pussy was spread open and exposed.
Well, he thought miserably, at least he would be able to go to bed today with his balls feeling just a little bit less full. Even if it meant having his load pushed out of him from the inside without even the slightest hint of relief or pleasure. A feeling that wasn’t made any better as their mother stepped forward to place her hands against the flat curve of his buttocks from below.
“Nervous?” she asked.
“N… no,” said Thomas.
“That’s a good boy,” she said, her fingers dancing just beyond the edges of his scrotum, “Now who wants to go first?”
Another brush of her fingers, and he squirmed at the touch. A short moment of silence followed, broken only by the sound of the clock on the wall. Tick, tick, tick, it went, the rhythm interloped perfectly in time to the beat of his heart. Thomas felt himself tense up. It was going to be him, wasn’t it? The fact that it had been quite a while since he had his prostate milked like this was proof enough. Never mind the fact that his sister was here watching as well.
As bad as his luck was however, this time, just as he was about to give in and accept his fate, there was the ever-so-vigilant sound of protest from Sarah, typical wonderful Sarah, doing everything she could to avoid having yet another object shoved up her most intimate hole. Which, according to the long-established rules of discretional volunteering, only served to signal her out.
“Not me,” she said.
“Oh?” said their mother, turning to her, “And why not?”
“Do I really have to say it?” grumbled Sarah, “Go make Thomas do it instead. Besides, it’s not like you’re going to let him put it in today anyways, so why can’t I just go back to my room?”
She scowled, rolling her eyes for good measure. A rather well-thought-out argument, and it might have even worked had they been talking about almost anything else. As it was though, the moment their mother looked towards her, it was almost as if the entire world ceased to revolve. And a stone sinking into the ocean, Thomas tried not to feel too guilty over the amount of relief he felt. Really, she should have known better, especially after all this time, though he supposed that there might have been just a bit of leeway considering that she was currently lying naked and bent over the edge of the couch. That, and the fact that it had already been several months now since either of them had been allowed to cum.
For now though, given their current predicament, it was probably better for him to focus on something else. Biting down on his lips, he tried not to think too hard about the thought. Sixty seconds every week, plus the usual exercises they were required to do after school. And after so many days of being denied, even Sarah was bound to start feeling just a bit uncomfortable. Not that she would ever admit it to his face, even if it was the only way she would be allowed to cum.
Smiling, their mother lifted her hand up, and Thomas watched as she reached out not towards him but instead towards the delicate and inviting folds of his sister. A pause, in which time stood still, and then as the thin layer of her gloves finally made contact, she almost seemed to jump up as if shocked.
“Looks like we have a winner!” said their mother. Her smile grew even wider, matched in its brilliance only by Sarah’s cry of betrayal.
“But why?” she cried, “That’s not fair. You can’t do that.”
“You’re right,” said their mother, “We’ll have to get these out of you first.”
It was the usual pattern of indignation that always seemed to occur. There was another round of protests as she reached her hand out again, and cupping her fingers just below her slit, she placed her other hand against Sarah’s back and pressed down. Sarah blushed, mumbling something about never giving in, and her face grew even redder as a finger slowly made its way into her tunnel. A soft plop, followed by one more, and then a moment later, their mother was left holding the two small spheres that served as her ben wa balls. Measuring out at just under an inch in size, even from afar, they looked quite large.
“Now, that wasn’t so hard, was it?” said their mother.
Sarah said something quite unrepeatable in response. Something to do with the repeated insertion of one object into another, and the suggestion that the listener should consider it as a thought. Which was rather ironic, considering the way her bottom was pushed upward right now with her legs spread apart. Their mother only laughed, however, as she moved her fingers back up to trace a short pattern around the edges of her hood.
“Alas,” she said, shaking her head in mock pity, “If only you could adopt the same attitude with your brother. You would think that you would be a little more enthusiastic about it after all these months, but I guess not.”
Sarah could only moan in reply. A second stroke, and then a third, each pass moving closer and closer to the tiny bump at the top of her slit, and her voice seemed to cut off as she tried not to clench down. Regardless of how much she strained herself, however, the fingers still never quite seemed to reach, dancing just around the place where she needed it the most. Over and over they teased her just short of the edge with her labia fluttering open and shut. Then, one last brush against her lips, and then it was up to the opening of her pussy as she gasped at the loss.
“Why?” she sobbed, “I was almost there!”
A somewhat moot point, since it only seemed to confirm their mother’s efforts even more. She reached her hand out again, and if Thomas could feel his dick growing just a bit harder at the sounds of his sister’s frustration, then the shame was only just covered up only by the knowledge that it would soon be his turn.
And this time, unlike all the previous weeks, there was no time limit on how long they had to endure. Which meant that only the limits of their exhaustion had any effect on the number of times they were destined to hit the edge without being able to go over. Five minutes, ten minutes, thirty, or even an hour, to say that it was uncomfortable was putting it lightly. Cruel and unusual was only just a bit closer. Only that under the guise of a checkup, they really didn’t have any other option but to take it as it was.
Tap… tap… tap…
Already, they were on to the tapping stage. A ritual he only knew about via half-caught glimpses through the door every time their mother pulled his sister aside for a “talk” in her room. And with each prod of her entrance, Sarah seemed to disappear down into the couch even more. She bit down hard on her lips, her walls growing tighter with each stroke of her hole. Then, just when it looked as if she couldn’t take any more, like a perfectly tuned machine, their mother pressed her fingers forward.
“Oh…!” said Sarah.
Layers of pink split open, like the petals of a flower as the digits finally found their way home. Sarah gaped, her back arching upward as their mother pressed down. Almost like a cat hunting a mouse, and the moment they found that secret spot inside of her, her legs almost seemed to snap shut with a will of their own.
“Look at that,” said their mother, “All nice and firm.”
Sarah groaned in frustration, unable to do much but moan.
“Except,” said their mother, “No matter how much I tease you down here, you still won’t be able to cum. Not without your clit at any rate, or something else considerably thicker thrusting inside of you while you’re at school. Say, a dildo harness perhaps, or maybe even your brother.”
A pointed look towards him, and Thomas tried not to focus too hard on the implication of the words. Reaching down with her other hand, their mother continued on with the strokes, drawing back the delicate covering of his sister’s hood to expose the stiffness of her nub. An attack from both sides, both within and without, all while keeping a careful pace to ensure that she wouldn’t be able to go over. Sarah cried out loud, the stiff peaks of her nipples cutting into the pillows underneath her as she tried to hold on. Against the onslaught of stimulation though, it was only a matter of time before her body gave out.
One last press against her g-spot and clit, and then…
“Stop!” she cried, “I can’t… it’s coming…”
Her hips lifted upward again, her entire body seizing up as she tried to clench down. As much as she tried to hide it, however, there was no escaping the careful and experienced eye of their mother. One last thrust inside her, just barely grazing against the surface of her walls, and then she pulled her hand away to leave nothing but the painful feeling of emptiness inside her tunnel.
The results were immediate. A single almost orgasmic twitch, followed by a half-dozen others, and Sarah moaned in frustration as her pussy went still.
“That’s one,” said their mother, “Think we should roll some dice to determine how many more?”
Sarah sighed, her head pressed against the cushions below. Fifteen minutes in, and they were barely even a sliver of the way through. Panting, she shifted her hips in an attempt to relieve some of the discomfort, and beside her, Thomas tried not to look too hard at the fluids running down the inside of her thighs and down to the floor. Well, at least it was over for her, even as her lips continued to flutter against the phantom aftermath of her denial. For him though, not so much. And as their mother turned her head towards him this time, he could only swallow hard as he looked up from the mess that used to be his sister.
“Ready for your turn?” she asked.
“I…,” said Thomas.
He hesitated, unsure of how to answer. What was he even supposed to say to a question like that, especially considering the current situation he was in right now? In the end, though, it hardly seemed to matter since his mother simply gave him a small pat across his rear before pressing forward. And as with how things usually went, it was only a short step from there before she reached over for the lube.
A small dollop across her fingers followed by a generous squirt between his cheeks, and then it was there, the feeling of something foreign and strange pushing its way into the intimacy of his backdoor. Down below, his member twitched again, a drop of precum already gathering across the tip, and he gasped as it slowly stretched out. Gathering it up with her fingers, their mother smiled as she added it to the existing pile of slipperiness coating his rear hole.
“Relax,” she said, “The less you try to fight it, the easier it’ll go.”
“I…,” he said, “I don’t…”
“Alternatively,” she said, reaching her hand up to cup his testicles again, “Be a good boy for me, I might just let your sister kiss it for you afterwards. Only the very tip though, and only if you promise not to shoot it all out the second you get to put it in her mouth.”
Her fingers slid in another inch, and Thomas moaned as his hips involuntarily rose up in response. And as much as he tried to deny it, he would be lying if he said that his pulse didn’t increase at the thought. Between his legs, he felt his member swelling up another fraction of an inch as it started to throb. Still trapped behind the plastic walls of his chastity cage though, there wasn’t exactly a whole lot of room for it to expand, and the mental image of his sister kneeling down in front of him wasn’t helping much at all.
Another press, and he groaned, shifting against the couch. No matter how hard he tried though, it was simply impossible to ignore the feeling of wrongness as the fingers pushed even deeper into his rear hole. Slowly, he could feel himself being spread apart, and he tried not to think about how he looked, naked and bent over with his bottom stuck out. Thank god it was only just Sarah watching him right now, and not his friends at school. If they ever found out about this, he would never be able to live it down. Getting edged through his dick was one thing, but having to take it through his rear was another. And the more he tried to resist the feeling, the more the walls of his chastity cage seemed to squeeze down.
There wasn’t much time to dwell on the thought however as his mother finally found what she was looking for. Up, down, left, right, and then it was there. A slight brush against his prostate, hardly enough to even be considered a stroke, and almost as if he had been struck by lightning, Thomas found himself involuntarily crying out.
“Ugh…!” he said.
Taking that as a good sign, she repeated the motion once more, and this time with his prostate trapped directly in between, the entire world seemed to tilt out from underneath him as his balls rose up.
“Oh…!” he said again.
It was like nothing he had ever felt before. A feeling of rising urgency, and then…
Thomas paused, his entire head feeling as if it was made out of cotton as the walls of his rectum clenched down. He was going to… do what? Cum? That was what his brain seemed to be suggesting, but even as his mother started to press...
