Sakura
Sakura listened to her servant plead on her behalf, hoping beyond hope that she would be spared from that, if nothing else. The spiked tendrils continued to squeeze Sakura's breasts painfully, causing her to let out more pained hisses, and her nipples continued to be rubbed with the abrasive sandpaper-like tendril, now extremely sore as a result. She listened to Wynn's response to Rider whilst she continued to suffer, uncertain how to interpret it. Wynn's tone and attitude towards Rider suggested it was good, but the agonised screaming that her servant soon began to emit suggested that Wynn had been somewhat unimpressed.
Finally, Wynn turned to address Emily, no doubt asking for a translation. Suddenly, Sakura felt the thorns digging into her skin disappear, and the sandpaper-like tendril soften, now kneeding . She sighed in relief at the indications of good will on Wynn's part, waiting for Emily to confirm the hopefully-good news.
"My bad, it seems that I mistranslated", Emily explained, causing Sakura to smile for the first time since her capture, "she just intends to make your husband's talents seem paltry in comparison to hers."
Even if Sakura still hated what was being done to her, at very least she now had the consolation that she would be able to return to her husband and enjoy her time with him. Still, the woman's words were laughable even if reassuring. Nothing, however good, could compare to the bliss of being in Shirou's arms.
With her worries reassured somewhat, Sakura could focus a bit more on her current situation. She felt the tendrils continue to squeeze her abused breasts and, additionally, to grasp hold of her sore nipples, tugging them upwards, causing her to let out a hiss of pain as the sore nipples were stretched. Then, she felt the tendril inside her slow, whilst another began to rub her hardened nub, causing her to let out another moan, this time of pleasure. She continued to moan, a little pain from the manipulation of her previously-tortured breasts mixed in with the mostly-pleasurable tones.
Rider
Rider let out a sigh of relief at Wynn's words, overjoyed to hear that she did not intend to cause Sakura any permanent harm. Of course, the woman's words were utterly false, but she had no way of knowing that. After all, she didn't know just how much Shirou meant to Sakura. And, Rider had to admit, Wynn was very good at this, even if she was somewhat sadistic at times, so she could understand her confidence.
Rider's thoughts were interrupted when Wynn decided to thrust the small tendril in and out of her urethra. Rider let out another scream of utter agony as the passage was ravaged and stretched in a way it was never meant to be, the sensation purely unpleasant. She watched as Emily began to undress Wynn, somewhat aroused by the sight, her screams gradually subsiding but the look on her face still one of pain.
Despire the pain she was in, though, Rider was able to focus enough to be able to hear Sakura's pained moans subside, and be replaced with more pleasurable ones, as Wynn seemingly made good her intentions. Happy that her master would at least not be physically harmed beyond repair, Rider relaxed as best as she could given the agonising pain coursing through her, her arousal growing once more as a result of the torture being inflicted upon her.