Sakura
Sakura continued to gasp and moan despite her best efforts as Emily pleasured her, adding a third finger to her tight pussy and continuing to lick her sensitive nub. The girl's admirable attempts at resistance were further hampered when she felt several tendrils wrap around her breasts, the new sensation breaking her concentration somewhat. The sensation became decidedly less pleasant when small thorns grew along the edge of the tendrils, which then began to roughly squeeze Sakura's sensitive mounds.
"Aaaahhhh", Sakura moaned from the uncomfortable sensation of the many tiny thorns pushing into her sensitive flesh as the tendrils squeezed again and again, forcing the thorns to push down painfully.
The discomfort Sakura felt in her breasts worsened when several more tendrils began to rub slowly over her hardened nipples, the sandpaper-like texture irritating them significantly, although not causing any real damage, the feeling becoming worse and worse the longer the tendril continued to rub and abraze the sensitive nubs.
The new, uncomfortable sensations forced Sakura's attentions back to the situation she was in, making it almost impossible for her to ignore Emily's ministrations. As a result, she began to moan louder and faster, the occasional hint of pain caused by the rough treatment being inflicted on her breasts noticable in the tone of her moans. After some time, Sakura felt Emily withdraw the fingers that had been pumping in and out of her, replacing them quickly with her tongue, whilst the fingers moved to rub her now-highly-sensitive nub mercilessly.
Sakura began to pant and moan louder and louder, now having lost any semblance of resistance as a result of the combination of Emily's ministrations and the slight torture Wynn was inflicting on her breasts. The discomfort in her breasts began to become greater and greater as the rubbing and squeezing continued, inflicting small but constant amounts of pain. Sakura was now close to orgasm, her folds drenched and her nipples and clitoris rock hard, the hardness and arousal only increasing the discomfort from Wynn's abuse. Sakura felt degraded and uncomfortable, both from the abuse she was suffering and, also, the fact that she appeared to be enjoying it.
Rider
Rider felt Wynn grab hold of her jaw, before taunting her about her feelings for Sakura. Rider knew, of course, that she was entirely right, but her enjoyment of Rider's anger coupled with her knowledge of how to cause that anger was an extremely disconcerting combination. And, indeed, Rider's fears were soon proven correct as Wynn summoned up tendrils to begin to play with Sakura's breasts, squeezing them and rubbing the nipples. From where she was, Rider couldn't see exactly what Wynn was doing, but the uncomfortable look on Sakura's face and the pained tone of her moans indicated that it was more than just simple squeezing. She was inflicting some sort of torture on Sakura, solely to make Rider angry.
"Now, isn't that a fetching sight?" Wynn said, finally removing her hand from Rider's now-soaking-wet folds.
Rider tried to hold back her anger, knowing that that was what Wynn wanted from her, and that to give her it only invited more punishment for Sakura, but she was only partially successful, and Wynn could likely see the hints of anger in her face. However, that anger was quickly replaced with a look of pure pain as a thick shadow phallus thrust hard into Rider, almost lifting her off the ground, causing her to let out an agonised scream. Then, Wynn waved her hand in front of the tendril, and Rider felt yet more pain rip through her as it expanded further.
"AAAHHH!"
This was genuinely torture for the servant. And, yet, she was still highly aroused by the treatment. She continued to pant and moan, her arousal if anything becoming greater despite Wynn having stopped pleasuring her directly. It would not take much for Wynn to bring her to orgasm at all.