Sakura
Sakura lay back into the tendrils binding her, panting, as she came down from her orgasm, a sense of shame and humiliation washing over her at what had happened. With Emily now having stopped her ministrations, there was no longer any pleasure to mask the pain Wynn's tendrils were inflicting on her breasts. Sakura began to emit pained moans as the tendrils squeezed and cut her breasts, and as her highly-sensitive and sore nipples were rubbed over and over by the sandpaper-like tendril. She could see Emily wiping off her face and enjoying the taste of her fluids, and she gave the girl an angry glare.
As she began to recover her senses somewhat, Sakura looked over at her captor and Rider. She could see the pain on her servant's face as the black-haired woman seemingly tortured her with more tendrils, and once again she felt guilty for putting her servant in this situation, and forcing her to suffer the same treatment as she was suffering. Her focus on her servant was cut short, however, when Wynn made another statement in English, something about girls and a man, before thrusting another tentacle inside her. To Sakura's surprise, whilst it was somewhat on the large size, it was not unpleasantly so. However, she was still rather sensative after her earlier orgasm, and this was not a particularly welcome intrusion, even if it took her mind off the torture being inflicted on her now-somewhat-blooded breasts.
As Sakura wondered what Wynn intended next, though, Emily spoke, translating what the black-haired woman had said, in her own way.
"She's intending to ruin you for any man after this", Emily said for Sakura's benefit, "Chances are that it will be quite...enjoyable."
Sakura glared at the red-haired woman with pure fury in her eyes, before rapidly changing to something between fear and sadness.
No! No! No!
The thought of never being able to enjoy sex with Shirou again petrified her. She could deal with being raped, she could deal with being tortured, but not that. She loved Shirou, she wanted to be with him, to be able to pleasure him and be pleasured by him. For this woman to take that away from her forever was unthinkable. As the red-haired woman addressed Wynn, asking if she'd like to be pleasured, Sakura broke down, unable to accept the possibility of being unable to enjoy sex with Shirou.
"No, please. I'll do anything, please", Sakura begged. "Don't do it, I'll do anything! Please, stop her!"
Sakura felt utterly despondant. She could cope with rape and torture, she'd suffered worse in her life, but losing her ability to enjoy sex with Shirou was not something she could handle. And, yet, there was nothing she could do to prevent it, aside from hope that these two would have at least some basic concept of compassion.
Rider
Rider continued panting as she came down from her orgasm, still glaring angrily at Wynn as she continued to torture her master. As Sakura, too, reached orgasm, finally, Wynn began to push the thick, ribbed dildo that was still stretching her as far as it would go, all the way down inside her until it reached her cervix. A grimace of pain came over Rider's face as the device came to rest, filling and stretching her entire pussy. With that, Wynn looked at Rider's face, before practically singing her next words.
"I do believe something interesting is about to happen", she said, beginning to rub the space between Rider's clitoris and pussy with another tendril.
"I doubt you use your bladder, correct?" she asked, mockingly, as she thrust the tendril into the small hole, causing Rider to moan in pain.
Rider squirmed uncomfortably as the tendril pushed inside her urethra, the sensation decidedly unpleasant. And, yet, Rider's masochism was such that part of her was turned-on by the sensation. However, as she writhed around in discomfort and her arousal grew, she heard Wynn address Emily.
"I believe it's time for me to ruin this girl for a mortal man", she said, before creating a new tendril and thrusting it inside Sakura.
A look of horror came over Rider's face at Wynn's words. She'd expected torture, yes, but she had hoped that, at least, no permanent damage would be caused. Despite her discomfort from the tendril in her urethra and the phallus stretching her insides, she glared angrily at the woman as the tendril thrust into Sakura. To her surprise, though, there was not as-of yet any indication of pain from her master. Still, Rider knew it was only a matter of time, she knew from experience that Wynn could alter the tendrils at will. Her horror and anger worsened when Emily spoke, translating Wynn's words. Immediately, she could see the anger, fear and sadness in Sakura's eyes.
Rider's heart broke as she listened to her master begging for mercy, knowing how she would have interpreted that statement. That she would see it as a loss of her ability to pleasure and be pleasured by the man she loved more than anything. She could see the utter despair come over Sakura's face as she realised that there was no way she could prevent this.
Despite the discomfort she was in, Rider could not simply let this stand. She would do literally anything to prevent it. Her face set in a grimace from the torments being inflicted on her, Rider addressed Wynn, trying to be as respectful as she could.
"Please, Lady Wynn, please don't do that to her. She's married and she loves her husband more than anything, denying her the chance to make love to him would be cruel. We will do anything you want, just please don't destroy her like that", she said, almost begging.