The instant Sans thrust into Frisk, he felt them start convulsing around his dick and the look on their face was just as beautiful as he’d imagined. He wasn’t anywhere near as close to the edge as they were, and was delighted to be able to stretch out their pleasure as hard as he could.
God it felt good.
The tightness, the heat, the slick wetness, the way their depths gripped him, almost crushing with the strength of their orgasm… it had been way too long. They honestly looked close to blacking out and so, in addition to everything else, he felt a wave of pride flood him.
For a time, he lost himself to the primal pleasure of it all, gripping their hips and slamming into them as they screamed and moaned out his name. Something about sex was just so easy to get lost in. Those nagging doubts and uncertainties were washed away, and for the first time - other than when Frisk pulled that little stunt with the blowjob - he was able to just lose himself in the moment. It just felt good on so many levels.
He also managed enough presence of mind to note he remembered absolutely nothing, not even faint impressions. This was the first loop. This might really work. Hope, real hope, was a wonderful thing to feel and blended well with everything else.
After Frisk more or less recovered from their fantastically intense orgasm, they slowly regained themself and started taking over the movements. He let them and lay back, letting himself be pleasured for a little while.
This. This was amazing. Laying back and letting himself just enjoy it all. Watching them move on his dick, feeling the pressure squeezing around him with the rhythmic motions, seeing the slight sheen of sweat as they lightly panted, the look of absolute bliss on their face…
It didn't look or feel like they were trying to drive themself to another orgasm. It was like they were simply savoring the experience, like they wanted to stay in this moment forever. Still, he knew it couldn't last. Both of them were driving higher and both of them would fall.
He wanted to drive them insane again. Guess that meant it already couldn't last, because the temptation was irresistible.
He grinned at them and pulled them off his dick, then teleported directly behind them. He shoved them roughly forwards, displaying their ass and a different angle on their pussy.
He didn't want them to have time to think, to anticipate, so he immediately thrust into that beautifully tight pussy again, and slapped their ass once he did so.
The sounds of shocked pleasure were the finest background imaginable for the pleasure coursing through him. He laughed in sheer delight and fell again to his need, pounding them hard.
But there was more fun to be had.
Before they fully managed to recover from the surprise, he had another one for them. Grabbing their ass, he made a nice sheath of slick magic around his thumb and drove it in all the way, making for a fantastic squealing shriek from them. He couldn’t help but laugh again.
Apparently they really liked having their ass played with, because it set them off, and he groaned as he felt them convulsing around his dick and thumb both. Nearly sent him over the edge and it was all he could do to hold back, feeling himself swell and twitch within them. He dug his fingers into their sides, trying to maintain a grip on his own sanity.
“fuck,” he grunted, holding them still and trying to pull back from the edge. “i forgot i need to… damn it, frisk, this is distracting…”
“It’s so good,” they said, flopping down onto the bed.
He laughed a little, but that made him move and his dick twitched some more, shifting his laugh into a groan.
“you feel amazing,” he said, taking a quick breath. “i almost forgot and was getting close… i need to do the thing. you need to be careful, alright?”
“I will,” they murmured, and then they whispered, “Please, Sans, stay with me…”
A sweet, but painful wave of emotion filled him at that. Bittersweet, hopeful, joyful that they wanted this to work, too; fearful, guilty that all this was technically just for pragmatic reasons…
“i’ll try,” he said, keeping the emotion from his voice, and then internally sighing at himself for doing so. “i know it’s a bit repetitive, but the first position honestly will probably work best for this. i’d kinda forgotten why i’d chosen it.”
They giggled and sat upright, spreading their knees to give him room. With another flicker of magic, he appeared below them and immediately thrust inside with a groan of satisfaction. They began to move on him once more, riding him smoothly.
In some ways, this “bridge” was incredibly easy. Sans just had to let go of all his emotional barriers and let his heart flow into them. Monsters could do it accidentally, if they were feeling really intimate during sex.
But in two rather specific ways, this wasn’t easy. One, because Frisk was human, it wouldn't be safe to happen naturally - Sans had to try to direct and push the connection consciously, which took a little bit of focus. He wasn't going to be perfectly careful, but he needed to keep it at least a little under control.
And, the bigger problem… even with everything he’d said and done, everything he’d tried… he didn’t know if he could fully let go.
He could, before. Back before he’d gotten trapped here. He knew what it was supposed to feel like. Thing is, those memories still ached. Now? He didn’t know if he could do it.
But he’d try.
He relaxed the boundaries of magic around his dick, letting his soul seep into Frisk. It didn’t feel the same as what he remembered, but then, he had no idea if it was because Frisk was human, or because of emotional issues in himself, or if Frisk had emotional issues blocking things, or if he’d made the connection wrong, or what. He had no idea if it would work. But he just focused on letting himself flow, as best as he could.
It hurt. It hurt more than he'd expected.
He didn’t touch these memories, these powerful experiences that had shaped his soul, didn’t talk about them, for a reason. He wasn't reliving them or anything, but even just trying to want Frisk to see him made him aware of what, exactly, Frisk would be seeing. It wasn’t the worst pain, but it ached.
He clung to Frisk tighter as he filled them, embracing the closeness and not just the pleasure. He tried to want Frisk to feel him, and to feel them in turn.
It wasn’t smooth, but he could feel a glimpse of them. Of their soul. A strangely deep sense of contentment, satisfaction, and simplicity of purpose. Fear, guilt, and other things flooded the mix, but at the root of it all was an odd sense of stability.
Their devotion to him, he realized. It really was baked into the depths of their soul. And it didn’t hurt them at all. It was a thing of joy, not bondage, to them. Just like they'd been trying to tell him all along.
Something loosened in his own heart, feeling that. A mirrored sort of contentment.
He looked up at them and they met his gaze with curiosity, awe, and pleasure on their face. He wondered what they felt of his soul.
They’d stopped moving as they gazed at him, and he pulled them close once more. Less desperately, less needfully, and with more tender care, he sank into them. He still couldn’t quite stop that feeling of a barrier in his own heart, a desire for them to not really see everything, but he tried to tear his heart open as he took them.
They had a look of concentration for a time as he thrust into them, that grew to an increasingly satisfied smile, though their skin grew more pale. Finally, they looked content and reached over quickly to grab a pie, once again demonstrating their knowledge of how to consume its magic without actually eating it, restoring their vitality. With that, they grinned at him brightly and joyously. Triumphantly, even.
They kissed at his neck and lay on his core, his magic overlapping their body where they lay. His pleasure slowly crested and he knew this would soon be over. He didn’t want it to end, but he wanted… he wanted the satisfaction. He let his dick grow thicker, feeling them tighten around him, hearing their breath as they grew closer to their own release.
They met his eyes as they came, moaning beautifully as their pussy clenched around his dick, and there was no resisting that. The pleasure flooded him as he came inside, buried to the hilt and gripping them with his full strength. Not within their soul, but still wrapped in their heat and pleasure. It wasn’t as powerful an orgasm as before, but it was wonderful and ever so much more fulfilling.
Frisk collapsed onto him, and they both panted in fatigue.
“That was amazing, Sans,” they murmured. “Thank you.”
He grinned, even though they couldn’t see it.
“it was sans-sational,” he said and that set Frisk into a fit of giggles.
Their laugh was great to hear, and the way their body felt on his as they laughed was even better. Especially since he was still inside. Mmm. He didn't want to stop feeling them, and until he let go of the sensation, his dick would remain to provide it.
“That was so bad,” they said, unable to stop giggling.
“your pussy quivers when you laugh,” he said with a grin. “that’s good to know. it feels good.”
They grinned back, but their expression was a little downcast.
They were afraid that he’d forget. He was trying not to be afraid, too. If it didn’t work, he’d forget all of this. The way it had felt, physically and otherwise, the insight into who they were… he didn’t want to lose this. It had been incredible. Just a few minutes, sure, but an important few minutes.
“Did it work?” they asked.
“i’ve never done this before with a human,” he admitted. “it was different. i made the bridge, but i dunno. it’s the best i can do. i guess it’s time to see if it worked.”
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“I don’t want you to forget,” they murmured into his neck.
“me neither,” he said. “for, uh, multiple reasons.”
“I’m going to try,” they said.
He hesitated, staring at them. He didn’t want to lose this. But it was time. He hoped… and he nodded.
They closed their eyes and whispered, “Please stay with me.”
That was the last thing that Sans ever heard.
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Just as the golden glow began to fade, Sans gripped Frisk’s hips and drove himself deep into their quivering wet heat and groaned in pleasure. He felt them start convulsing around his dick and the look on their face was just as beautiful as he’d imagined. He wasn’t anywhere near as close to the edge as they were, and so retained a presence of mind.
Enough to realize that this seemed very familiar.
It hadn’t worked.
They felt good on him, and that was distracting as hell, but he tried to think about those impressions he was feeling. They seemed unusually strong, but they were always stronger with emotional intensity. And this was a really intense experience. Maybe the connection had helped, but also maybe it was just because of how potent it all was.
Which meant he felt kinda hopeless. He’d have a good time, and then this version of him would cease to exist, would die. He could make them stop, but there was a chance multiple trials might make a difference, so he could just leave things to Frisk. And so this would happen over and over until Frisk gave up on this approach.
Considering how intense the start of the loop was, it might be a while. Well, he’d give them both a good time, at least. Dying man’s prerogative, right?
They took some time to come down from their initial orgasm. As soon as they seemed to regain themself at all, they started to take control, riding him, as they met his eyes and spoke. He groaned in pleasure as they moved on him.
“Sans,” they said. “Do you remember…?”
Second loop, then.
“i knew it wasn’t the first loop,” he said breathlessly. “it felt stronger than other impressions, but also maybe because it’s…”
He trailed off.
“We can try again,” they said. “Make the connection, Sans, and let me give you pleasure.”
He lay back and let them please him. It was good. They moved in different ways, and he freely let them see what worked best for him. Might as well give the other Sans-es a good time, too. While they worked his dick, he worked his magic, though he felt the wall in his heart had thickened up again. Still, he tried.
The connection wasn’t the strongest it could be, but it was the best he could do. He even got a sense of deeply rooted contentment from them, like they were satisfied with something in their life, though couldn’t really get any details. He hoped it meant they were happy, and that they were okay. He hoped they would be okay.
He knew, when his pleasure crested and he finished within them, that this wouldn’t work, that he would die, but it had been a good way to go.
They didn’t ask his thoughts, or talk, once he finished. That Sans’ last moment ended on a very high note.
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Just as the golden glow began to fade, Sans gripped Frisk’s hips and drove himself deep into their quivering wet heat and groaned in pleasure. He felt them start convulsing around his dick and the look on their face was just as beautiful as he’d imagined. He wasn’t anywhere near as close to the edge as they were, and so retained a presence of mind.
Enough to realize that this seemed extremely familiar.
It hadn’t worked.
They felt good on him, and that was distracting as hell, but he tried to think about those impressions he was feeling. He didn't realize that he was thinking the exact same thoughts he’d had dozens of times before, repeating pointlessly.
Once Frisk’s orgasm started to pass, they moved more assertively on him. They felt good - too good. The pace, the angle, the way their depths gripped him… He was taken aback by the sheer perfection of their movements. And the look on their face - how long had they been riding him for?
Good as this felt, he wasn’t going to stop them. They had this under control and he just lay back and let himself be intensely pleasured. Didn’t stop the dark thoughts, the nihilism and sense of hopelessness, but it was a damned good way to go.
“Sans,” they said with a breathy moan. “This is so good, but I want… I want…”
“i know,” he said. “it didn’t work.”
They opened their eyes and met his gaze as they rode him.
“Let’s do more,” they said. “Let’s combine ideas. Kill me, Sans.”
“what the… damn it, frisk, no, that’s…” he spluttered, but they ramped up the intensity of their movements, making it practically impossible to think.
The one thing he could readily recall was that this was a line he’d been absolutely committed to not crossing. He’d started to think that accidents might not be the worst, but still, to intentionally kill them? No.
“It’ll be so good,” they said, closing their eyes again as they started moving with maddening perfection, driving him even harder. He couldn’t think. “It’s so good when you kill me, Sans.”
They were seriously pushing him on this. On killing them during sex. And they were asking a version of Sans that was about to die, so his last act would be to cross a dearly held line, for their deranged pleasure. He couldn’t think, but he could feel, and what he felt was anger.
“i can’t kill you during sex, frisk, that’s way too far,” he said, the flames of that anger filling his voice.
“But it’s good,” they said with another moan. “I deserve it, Sans, I killed Papyrus. You should kill me. I want you to kill me when I cum… it’s so good…”
That was it. Sans had had it.
Something about this request… a line he’d considered absolutely, horrifically uncrossable, presented in the form of a demented kink. The way that wretched suggestion paired with his own desolate despair, and the impaired thoughts from the maddening pleasure. The fact that they brought up killing Papyrus now, of all times. He broke. He was completely out of fucks to give.
“fuck you,” he growled, real anger, bordering on rage, heating his voice. “i’ll kill you when i cum.”
Their eyes widened and they gasped, and of all the fucking things, that apparently set off their orgasm, as they spasmed and clenched on his dick. He had fucking had it with their fucking insanity.
He’d had it with all of his limits.
He cut all restraint from the magic binding the form of his dick, and it swelled within them. They felt incredibly tight around him, their own life energy constraining his form as his girth stretched and strained their body.
It was too much, he didn’t fit well. But his struggle to take them was just due to their position - he didn’t have the leverage.
He reached up and grabbed them by the throat, a flash of magic in his eye helping his motion as he slammed them into the bed. He flipped over onto them and drove himself between their legs. With this angle, force and intention would make him fit, regardless of physical complications. They let out a scream of blended pleasure and pain as he bottomed out, their pussy not even slightly able to take his full length, still shaking in the aftereffects of their orgasm.
This growth wasn't good for anyone. It was wild, unstable, and dangerous. He was leaking magic like a sieve, and he didn't have the magical stamina to maintain this sort of thing.
But he knew a solution to that problem.
“let me all the way in,” he growled as the limits of their flesh prevented him from going deeper. He didn’t know how to phrase things, but he didn’t care. “let me take your fucking soul.”
Another gasp of pleasure ripped from them, and a look of focus crossed their face.
His next thrust wasn’t stopped by flesh at the end, and the surge of vitality flooded him again. It was even better than before, as it was not only going through his locus of pleasure, but it was also immersed in theirs. Their vitality restored him, enabling him to keep his outsized, unstable dick in action.
He didn’t want to cum yet, because he knew as soon as he did, he’d die for real. This version of him, anyway. A minute ago, he was fine with that, but right now… he was too pissed at them to want to let go. He didn’t even know what he wanted. He was just… everything. Anger, lust, despair, hopelessness, frustration, pleasure - shit tons of pleasure - and just everything. He was just throwing everything at them in sheer overwhelming… everything.
And it felt incredible.
They twisted as he took them, reaching over and grabbing a piece of pie. They pulled it to their mouth, touching their tongue to it, and quickly absorbing the healing magic. He felt the magic flow through them, flow through his dick and into him. Neat - it was still healing magic as it affected him. Not that it mattered, when he was about to die from killing them.
But all of this felt so good.
He wasn’t going to be able to resist for long. He cut his emotional barriers, too, letting the connection flow without any sense of sanity or restraint. They shuddered again, their skin visibly going pale and they flailed for another piece of pie. As before, they consumed the magic with masterful speed.
The pleasure was intense. Mindbreakingly so. If it weren’t for the fact that he knew that he’d die when he came, there was no way he’d resist. And he was still too mad at them to give up, to go quietly to his end.
Even so, he knew it wouldn’t take long. Each thrust, feeling the physical pleasures - the tightness, the heat, the texture of their trembling walls gripping him. The soul pleasures - the vitality surging through him, carrying their lust and his both, flooding through his entire being, infusing pleasure and desire into every part of his body and soul. The emotional connection that he was halfway ignoring, in part due to being pissed at them at this exact moment, that nonetheless filled him with a sense of Frisk’s contentment and satisfaction with life.
They ate a third slice of pie. He was going to try to hold out until they’d eaten all of it. He wouldn’t live long, but this was so intensely good, he didn’t want to give it up.
He summoned his blasters when he knew his will would crack soon.
They moaned in renewed pleasure on seeing the blasters and the look they gave him was not making it easier to resist cumming. He fell onto them, gripping them tightly, trying not to let go of this pleasure. Trying to hold on, in every sense.
His emotions grew muddled within the insanity and the sheer, mind-breakingly intense sensations. He didn’t even know if he was mad at them anymore. He was just a mindless thing of need, of connection, of sexual gratification. He barely noticed when they reached out and grabbed a fourth slice. He barely heard them as they moaned out his name, and tears flowed down their cheeks, and they babbled about how good everything felt.
They came again and that was too much. Their orgasm poured through the two connections - through his dick buried in their soul, through the more normal emotional magical connection he’d forged. Combined with his own pleasure, he couldn’t even remember why he was resisting this anymore. A vague thought of death crossed his mind, but he didn’t comprehend it.
He released everything, absolutely everything, into Frisk. His orgasm, his magic, the blaster’s strike, his own soul pouring through their connection. And he felt it returning to him as their body burned beneath the assault, clenching in more than just the throes of orgasm as death took them. Their soul was already “leaking” into his from the connection, but as they died, it poured into him more absolutely.
The full measure of power of a human soul, pouring through an oversized and unstable conjuration of lust and pleasure, compounding all other sensations that were already tearing apart his mind from the intensity.
It was pleasure unimaginable. Satisfaction beyond all comprehension. It was a moment of such absolute perfection, despite all the deranged circumstances that led to it - but in that moment, none of that mattered. There was only perfect fulfillment.
Save for a single low note. He felt a faint touch of sorrow that this was the end… and then he felt disoriented as he was laying on his back for some reason, and Frisk was falling down onto his dick, immediately orgasming as they did so.