Something weird was happening today. The only problem was that Thomas didn’t know what. Or how, or why, or even when, which was doubly weird since the rules were quite simple when it came to these types of events, and it wasn’t every day that he found himself enjoying himself quite as much. Not since the last time the dice had fallen into his favor, at least, and he had managed to roll a twelve. Or a seven with the softness of his sister’s pussy clamping down around his member, even if he still hadn’t been able to cum at all. Sarah had been mad about it as usual, of course, stomping off to sulk in her room, but that was just how it was. What he did not expect, however, was for him to wake up a mere twelve hours later to find himself exactly where he was now.
He closed his eyes and opened them again. It wasn’t real. There was no way it was real. There was nothing in the entire world that could convince him of the thought. Not even as he looked down to confirm that the scene in front of him was still the same as before. Him standing in the kitchen with his pants around his ankles and his underwear pulled down, only that this time it was his mother kneeling down in front of him instead of his sister as she sucked him off.
“About to blow?” she asked.
Somehow, despite the fact that her lips were currently wrapped around his dick, the words came out perfectly clear and understandable.
“Uhhh…,” said Thomas.
“Or would you rather prefer to hold it in a little longer?” she said again.
Her tongue moved up to press against his shaft, tapping ever so deliciously against the underside of his frenulum, and he shivered as his brain started to melt. This wasn’t happening, there was no way this was happening. After an entire year of being locked up in chastity, there was no way he was getting a blowjob from his mother the very next day after his sister had just failed to make him cum. And as if things couldn’t get any more inverted, apparently there was a punishment for failing to do so now, and he looked over towards the corner to find Sarah standing fully naked with her arms tied behind her back and a vibrator shoved up her backdoor. A wire ran out from the base of the toy to a socket in the wall, and judging from the growing puddle of fluids underneath her, she must have been there for quite a while.
“Mmhhh!” she said.
The vibrator turned up another notch, and Thomas blinked as he watched her squirm. It was a sight he thought he would never see. Her being put in her place, all without a single comeback or insult, and she opened her mouth to say something around the gag she wore. Whatever it was, though, the words were cut short as his mother pulled his attention back down.
“Oh, don’t look at her,” she said, “It’s me you want, isn’t it?”
“Umm…,” said Thomas.
“Or did you think that I haven’t noticed the way you always stare at my tits every time you get unlocked,” she said.
There was another spike of pleasure as she swallowed his whole, and he gasped as his knees started to buckle. As good as it felt, though, there was something off about the feeling, almost as if it felt muted, and he blinked as he tried to focus. The task was made somewhat difficult though as he felt his balls start to rise up, and gritting his teeth, he shook his head as the world shimmered around him like a veil.
Think, Thomas, think. How exactly did he manage to end up here again? The only thing he could remember was going to bed yesterday with his dick shoved back into the stifling confines of his chastity cage and his balls feeling rather sore. Something that he was quite familiar with, and against the usual sense of frustration that always seemed to accompany his dreams, it almost felt as if there was an entire ocean of cum swirling about his seminal vesicles. Only that, for some reason that he couldn’t really understand, the pressure was strangely absent now, and as his mother opened her mouth again to lick all the way from the base to the tip, it was almost as if he was free to do whatever he wanted to her.
She looked up at him, her head still bobbing up and down, and he shivered against the thought. She wasn’t wearing any clothes, his brain noted, with the fullness of her breasts hanging out, and it was a world of difference compared to the tiny and miniature cones of his sister’s. Like a pair of proper melons with the perked-up ends of her nipples sticking out, and as she took him all the way down to the base again with her face pressed up against his groin, there was nothing he could do to stop the sudden spike of urgency as he felt his semen start to boil.
Soft, so soft, like she was sucking it right out. Just a little more, and then…
“Oh no you don’t,” she said.
There was a sudden pinch around the base of his member, and Thomas gasped as his climax was cut off. Shaking his hips in frustration, he whined against the sudden absence of pleasure. Of course this was going to happen though, a small voice whispered in the back of his head. What did he expect? Like, did he think that just because it was his mother servicing him instead of his sister now that he could just go and spew it all out? Expectations indeed. Shame on him for trying to find a way around. Or at least that was what he thought for about all of five seconds before his mother smiled again and stood back up.
“Poor boy,” she said, “All that spunk, and no way to let it all out.”
“I’m sorry,” said Thomas automatically. He braced himself for the punishment that was sure to come, “Please don’t lock me back up again. I didn’t mean to do it. I swear.”
If she heard him at all though, she ignored the sound.
“And,” she said, looking at him with eyes that made him shiver, “It would be such a waste to spend it on something as simple as a blowjob now, don’t you think. How about I let you do it somewhere else?”
“I…,” said Thomas.
Wait what?
Blinking, he watched as his mother spread apart her legs, and he looked down. There, set right in front of him was her pussy, fully waxed and shaven with the delicate folds of her labia standing out, and he swallowed hard as he felt his member rise up another notch. And as she walked forward to draw him close so that his dick brushed up against the inside of her thighs as she led him over to the couch, it was as if a part of him had simply decided to give up.
This wasn’t real, he thought, for the third time in a row. There was no way this could be real. The softness of the cushions pressed up against his back as she slowly sat him down. Then, her breasts were back in his face a moment later, and she straddled his waist with her legs on either side as she slowly lowered herself onto his cock. Inch by inch, he watched as the tip of his glands spread apart her folds, the pinkness of her lips sliding smoothly over the very end of his member, and still standing to the side, Sarah whined in frustration again as the vibrator buzzed away in her rear hole. Her clit was standing up stiff at the top of her slit again, throbbing in time with her pulse, and looking over at her, he couldn’t help but notice how desperate she looked.
All of a sudden, he felt just a bit guilty about having all the fun.
“I’m sorry,” he mumbled, “After this. I’ll make sure you… well, after this I…”
He tried to lift his arm up in apology, but she simply shook her head with her eyes wide open. Almost as if pleading for him to stop.
“Mmhhh!” she said.
“I know,” he said again, “But I can’t. Not right now. Just hold it in for another couple more minutes until we’re finished, and then I’ll…”
Whatever he had been about to say next never made it out of his mouth though as his mother dropped down to fully sheath his cock inside of her, and immediately he felt his eyes roll back into his head as he groaned. The pleasure was overwhelming, a tightness he had never experienced before, tighter than even Sarah was whenever he got to put it up her backdoor, and he gasped out loud. At the same time, though the feeling was back again from before, a tingling sensation of something strange and muted in the back of his mind, but, between the softness surrounding his member and the pressure rising up in his balls, it was as if his brain was unable to produce a coherent response.
“Oh!” he gasped.
Any further conversation was quickly shoved aside as she began bouncing up and down. Her breasts moved along in turn, swaying from side to side in front of his face, and he couldn’t help but drool. Back and forth, back and forth, like a mesmerizing pendulum of feminine allure, and he reached over to cup the two mounds. All the while, her walls seemed to squeeze down with an almost painful like grip that seemed to milk him for everything he was worth, and as his long-denied climax rose up inside of him, it was only the sound of Sarah crying out besides them that prevented him from tipping over.
“Mmhhh!” she sobbed, tears running down her face as she thrust her hips forward. She looked like she wanted to rush over towards them, but with the vibrator still buried up her rear and the stimulation turned up to the maximum setting now, there was nothing she could do but stand there with her nipples hard enough to cut through steel. And trapped on the edge of his very first climax in a long while, Thomas could only lie there in ecstasy as he ignored her warnings to stop. He couldn’t. Not now. Not when this was his only chance to finally cum, and his dick felt like it was on fire as his mother continued to bounce up and down. A deep burning fire that ran deep into his balls, and as he looked over to see Sarah trying to rub her clit against her thighs, there was one last spasm inside of him as if reality was slowly slipping away until the only thing he could feel was…
Dark?
Thomas blinked. All of a sudden, he felt that he was lying down. He opened his eyes and closed them again but the scene in front of him was still the same as before. A pitch-black void with nothing in it, though as his vision gradually adjusted and the light in the distance grew brighter, it was with a slow sense of realization that he was now somewhere else. And opening his eyes for the third time in a row with the light of the sun coming in through the window at a different angle now, he turned his head to see his mother standing besides him with a rather concerned look.
Immediately, he reached out towards her again, ready to continue, but…
“Are you okay?” she asked, “I heard you moaning, you know.”
She pressed a hand against his forehead, the soft touch of her fingers feeling rather cool, and against the silence that followed, it wasn’t until another couple moments of lying there that his brain finally caught up with the rest of his body. A dream? Had it all been a dream? Surely not. There was no way a dream could be that real, could it? His heart raced inside his chest. It was impossible. Out of the question. There was no way he would ever be able to accept such a thing.
All the same though, as reality slowly came back into focus and the birds chirped at one another outside, there was no mistaking the familiar pinch of something firm between his legs. And reaching over with his hand to pull aside the sheets, he looked down in despair to find the hard plastic shell of his chastity cage secured back around his waist. Right where he had left it as if it had always been there, and as if that wasn’t already bad enough, it was with an additional sense of disappointment that he saw the half-dried trail of stickiness leaking out past the tip. Which was something that he was normally quite familiar with, only that this time instead of the transparent texture of precum, the color was like that of a thick white cream.
“Oh my,” said his mother, “Well that’s a little embarrassing now, isn’t it?”
She reached over to gather some of it up, and Thomas grit his teeth. A wet dream, he thought stupidly. And he didn’t even get to properly cum. Nothing but a thin dribble of nothingness, worse than even a ruined orgasm or a prostate milking, and as if to add insult to injury, he felt his penis twitch inside his cage again at the memory of it all. His mother bouncing up and down in his lap with her breasts in his face, Sarah standing to the side with a vibrator shoved up her backdoor, it was all was nothing more than the pathetic fantasy of a mind pushed past well its endurance. And as the hand between his legs reached over to fondle the soreness in his balls, there was nothing he could do but whimper as he watched the last remaining bit of semen still trapped in his urethra flow out.
“Well, can’t be helped I guess,” said his mother again, reaching over for a tissue to dry him off, “Though I suppose it does sort of technically count. Let’s see. In that case, how about we skip the next couple of weeks with double exercises in between so it can build back up, and once you think you’re ready to try again…”
She smiled, and closing his eyes again, Thomas fell back against his pillow with a groan. Inside, his prostate was as hard as ever. There was no relief at all.
