Shove it into Jezebel's ass

Stick to the plan, this was more about breaking Jezebel than it was punishing Lilith. He'd get there when he gets there and all that. Positioning his hand so that he had a little more tail to work with, he shoved the spaded tip into the lubricated pucker. Jezebel stiffened, letting out an "Eep!" but not slowing or moving thanks to his command and Lilith's merciless onslaught. Using both hands, he fed more and more of Jezebel's tail up her own ass, the fairy equivalent to several feet disappearing into her bowels as she cried out and groaned in discomfort. With a final shove, Jezebel's tail now began just above her asshole and immediately disappeared into the cum-leaking hole. He grabbed her arms, breaking her free of Lilith's grasp and causing her to flop back against his chest. Her face was pained but her breaths were pleasured and she gave him a heated look as she continued to bounce to Lilith's tireless onslaught, "Tell me what it feels like to have your own tail shoved up your ass."

Compelled to obey, Jezebel whimpered her response, "I-Aah-AhAh! It feels weird... T-too deep! All... coiled... up... Anh!" "Uncoil it. Go deeper." Jezebel arched, eyes wide, "N-AAaaaaah! It's... it's slithering inside me! OooooOH! S-stop! Tell me to stop! AAAah! It's... it's so far in!" Bowen thrust harder into Lilith, his balls beginning to tingle as the demonette continued to narrate her suffering, "Ah! I think... I think it's going around a bend! F-fuck!"

Jezebel's frantic cries and fluttering muscles pushed Lilith to the edge, her eyes rolling up as her thrusts lost all sense of rhythm, becoming a frantic jerking as she pulled her down by her hips, "Lilith don't-Ngh-cum yet!" Lilith whimpered as her pace slowed and her trembling balls relaxed once more, the anger that had fueled her dampened by her unwilling compliance.

Bowen whispered into Jezebel's ear, the well-fucked girl's speech having devolved into desperate grunts and moans, "Alright Jezzy, how much deeper do you think you can go?" Jezebel groaned, teeth biting down on her long tongue, "I-AAAAuuungh! I can go a ways deeper... p-please don't make me-" "Stretch your tail till it's fully extended in your bowels. Then try and push it deeper."

"NNnnaaaagh!" Her back arched and her hands scrabbled at his shoulders for something to hold onto, his paralyzing command apparently forgotten. Eyes rolling, she gritted her teeth as her long fleshy tail, something she'd always been proud of, wound through her intestines. After a few moments what little of her tail he could see seemed to flex and strain, apparently reaching it's limit. Which was when the second part of his command engaged and Jezebel found her arm slipping around her back to cup her tail, "W-what am I-?" She grunted as her traitorous palm shoved another finger-length of her tail further inside her. Gasping and groaning, she shuddered for a moment before speaking in a quavering voice, "O-ok. It's all the way in."

"Pick up the pace Lilith, just remember not to cum." Lilith renewed her thrusting, nails digging into Jezebel's thighs as she fought to obey the conflicting commands. Jezebel quivered and twitched as she bounced on Lilith's rod, what little control she had over her own body beginning to falter under the dual sensations of pleasure and pain "Good girl Jezzy, very good. Now I want you to start thrashing it around like you were before it was in your ass." For just a moment Jezebel's eyes focussed and her mouth opened in horror before her tail flexed and she screamed, twisting and turning as her tail churned her insides. The sight of her smooth belly shifting and twitching, with the knowledge that she was doing it to herself because he told her to, sent Bowen over the edge.

Hauling Lilith's ass closer and lifting it for better access, he buckled down on pounding her abused hole. She was practically frothing at the mouth as every fiber of her being wanted nothing more than to unload her aching balls... but they stubbornly flopped below her pistoning cock, placidly churning with ever-increasing amounts of seed, as they refused to disobey Bowen's order. With a tremendous effort of will, Bowen pulled back and his cock popped free of Lilith's fuck-hole. Without missing a beat, he dropped Lilith's hips and thrust up as Jezebel's ass descended, popping his glans in beside her still-writhing tail. With a roar he unloaded his corrupted seed into her colon, flooding the already lubricated space with many times it's previous volume. He had one thought in mind which he infused into his seed as he hissed it in her ear, "You love this."

Jezebel's resistance was at its limits. The prolonged fucking, the humiliation, the insidious power Bowen had over her body... it all conspired to crack the shield of love protecting her mind. As great spurts of hot jism fountained into her bowels, it's twisting essence found the cracks in her armor and slipped inside. It spread like ivy over her very foundations and warped her desires around themselves. The pillar of her will, her unwavering loyalty and love for her creator, remained firm but the base of identity that it stood upon shifted and shook. In the blink of an eye, and the eruption of an orgasm, Jezebel's resistance shattered and her will collapsed.

With a euphoric cry of surrender, her eyes rolled up and she bonelessly slid back against Bowen's chest, insensate and exhausted. Bowen was pleased.

He wasn't sure if it had worked or not but he'd enjoyed the hell out of it in the meantime. He wouldn't mind having a repeat session or five, whether her mind was his or not, "Well, that was fun. Oh yes, Lilith. What to do with you..." The muscled demonette was still desperately thrusting, though clearly exhausted and practically immobile, her already sizable balls swollen nearly double with unreleased semen.