Sakura and Shirou
Shirou's moans of pleasure got louder still as Emily increased the pace of her strokes, continuing to regularly hit Sakura's now-welt-covered ass with the cane as hard as he possibly could, each strike bringing another scream of pain from the sobbing girl. Emily's vines. meanwhile, continued to whip Sakura's back, each strike bringing more pained screams from the girl and arousing Shirou further.
After a few more moments, though, the tendrils whipping Sakura's back stopped, instead moving over towards the wall. Emily continued pumping Shirou's hard length, his moans and pants becoming ever-more pleasure-filled as his arousal grew. Then, still pumping, she spoke, lust evident in her voice.
"Shirou", she said, "If you could please focus you attentions a bit lower, that would be wonderful."
Knowing that he and Sakura were "at her mercy", he obeyed her instructions, aiming his cane strikes towards the captive girl's upper thighs. Emily, meanwhile, continued to talk, all the while continuing to stroke the extremely-aroused Shirou.
"You know", she said, "I think I'll make him cum all over you. It would be a fitting way to start the task of defiling you, like you defiled me."
Shirou's arousal grew at her words, enjoying the thought of dirtying Sakura with his seed and humiliating the helpless girl. Sakura herself, meanwhile, was still letting out small screams of pain with every strike, the tears in her eyes flowing freely as the torture continued. The girl's words, too, were upsetting. Shirou was hers and hers alone, to have someone else bring him to orgasm was just wrong. And, yet, she could hear his loud moans, and knew he was close. And, when he did orgasm, she would be defiled by it, covered in his juices without any way to clean herself, her only involvement being the screams of pain that were obviously turning him on.
Sakura's thoughts were interrupted when she felt the vines return. She wasn't sure what they were up to, but she was sure it wasn't pleasant. She began to shake with fear and pain as she anticipated what was to come, the caning she was receiving from her beloved not letting up for an instant. Shirou, meanwhile, was intensely aroused by the sight, and the thought of what was to come, his moans becoming louder and louder as he rapidly approached orgasm.
Then, suddenly and without warning, Sakura felt something bite into her nipple. She let out an agonised scream as the clamp bit down and crushed her sensitive nub, before beginning to lightly tug on the clamp, bringing further moans of pain. Shortly after, she let out another loud scream as the vines applied the clamp to the other nipple as well, before beginning to tug on the chain connecting the two, each tug sending another jolt of pain through the tortured girl's body.
Shirou was now exceptionally aroused. Every scream and moan from the helpless girl was bringing him closer and closer to orgasm. The sounds of her sobbing and the sight of her beautiful body being abused was simply too much for him. He attempted to hold back, but he began to moan openly, clearly on the brink of orgasm. And, then, suddenly, with one final scream from the captive he was caning combined with Emily's sensuous stroking, he came, releasing his pent-up arousal and letting out large volumes of his cum. As he was, though, he had little control over where it landed, Emily being able to essentially aim it as she wished.
