Round 2 in Her #2 Winning Her Back chapter 15 by Anderson

For a while, Jack seems to be in control of his own fate. His limb and tongue action on the walls of Kate's vagina had her struggling for breath, and slowing down to reposition keeps her interest going well in waves.

The problem arrives when Jack takes slightly too long to catch breath trying to edge her, and gets scared back into action with a threatening growl. He leaps back into action with such a flurry, even Kate easily can tell how much her threat just terrified the little man. This turns her on WAY more than she had been before, and the result is-

After experiencing Kate's earth-shattering orgasm from inside, Jack hopes she'll be overwhelmed enough to go to sleep already. No such luck. He's gradually pushed out towards the exit, and then her fingers grasp his feet and yank him out into the sudden lamplight. "Okay, little cock. Are you still hard enough to stand nice and stiff and get up in my ass with ten toes down, or am I gonna start with your little head and work down from there?" Kate smiles.

Jack shivers as his fluid-covered form hangs in the cold air, and whimpers back: "Um... please Goddess, I'm too tired to serve you properly now. Maybe we could try again tomorrow?"

Kate rolls her eyes. "When you get more stamina, you can play with my pussy longer. If you're going to complain about being tired, don't complain when I put you where you have to work less hard. Now stand nice and hard at attention if you want to go in feet first, butt boy." She doesn't give him time to think, but spits on his head, and maneuvers him behind her waist.

Jack realizes he's doomed, and has only one terrible choice in this whole situation. Blinking back tears, he goes stiff in Kate's grip, causing her to coo in approval. "Want to enjoy it to the last? Or just holding off on being tainted forever? I can't imagine what this must be like for you!" She moans. "I just have to... mmm... do my best, and savor it..."

Jack blinks back tears as he holds still, and lets his own legs be shoved into the dark ring between Kate's butt cheeks. To his horror, he feels it react and wrap around him, clamping down and pulling him further in as Kate laughs. Her fingers shove his spit-and-cum-slick figure down to his waist, and he pulls his arms away reflexively.

"Put your arms down!" Kate immediately scolds, and her anus clamps down painfully and keeps on squeezing as it pulls him to his belly. His legs kick uselessly inside her guts while he struggles to breathe and pounds on her sphincter with his fists, until it finally lets up and lets his arms in.

"That's it... good little boy. I can't imagine feeding myself to someone's ASS like that. You should just admit it. You want to be my toy ALMOST as much as I want it. Well, maybe you thought it would be Zoe, but admit it, you tried to go to her thinking she wanted to do this all to you instead, right? Well, beggars can't be choosers! Hahaha!" She turns around and let go of her butt, leaving it to finally close around him.

The worst part?

Compared to the constant squeezing of her asshole and the battering of Kate's ass cheeks, the parts of him stuck totally inside her felt good... soft... low pressure... almost a siren song beckoning to give in...

At this point, Kate is satisfied to let Jack catch his breath for now, and grabs her faithful vibrator from the bedside drawer. "No, I haven't forgotten about you..." she murmurs to it, then flips over to her belly and starts working.

For the first few minutes, Jack has relative calm stuck halfway up Kate's ass, the rest buried in between her cheeks as she runs the vibrator and thinks to herself. Then, she starts breathing more heavily. He feels her squeeze around him - voluntarily or not - more often, and a little harder each time.

His prison starts to buck and shake. Kate is moaning and gasping, all of her muscles - including, no, especially those capturing Jack - spasming almost totally out of control. Jack is having the life squeezed out of him as Kate's hips buck and her ass cheeks slam back and forth against his head and shoulders, while his ribs are crushed by wild clenching below.

As a particularly hard bounce yanks him further into Kate up to his neck, Jack realizes something else: He's not even Zoe's mom's vibrator anymore. He's an accessory for her vibrator. Her regular vibrator is giving her an even harder orgasm than he had, just now, and all he's doing is fighting for survival as his limbs flail inside her rectum and his neck struggles not to snap from all the pressure.

There's no way he can fight it. If he tries to climb out somehow, or even try to stay as far out as he is, at best he'll pass out and at worst he'll suffocate or break his neck.

But the only other option is... no matter where he goes from here, no matter if he's ever rescued and his size restored or not, he'll always be a former butt plug to a horny older woman. He feel instinctively there won't be any going back from that. Once he's fully buried in that darkness... he'll be tainted forever.

Right?

"What's the matter, Jack? Just a little further and you'll experience more of your goddess than even my husband ever did. You'd like that, wouldn't you? So get in there!" Kate laughs, as Jack realizes she's fully aware of how she's torturing him. She just doesn't care. "Ngh... or do you want to seem ungrateful?" She growls. "Most people don't try to clean their butts just to be nice to their ass toys, you know."

Fighting for his life to keep his head outside her anus, Jack finally understands how much Zoe's mom sees him as a thing for her amusement. As far as she's concerned, if she wants to shove him up her asshole, he should be grateful it's a clean asshole.

And... maybe he should? Outside is loud, hectic, painful battering and struggling and choking. He can barely see anything in the moments Kate's hips thrust and light floods into her ass crack, and then he's hammered in the face and choked.

Inside...

Inside, he was also struggling. But it was so much softer, warm... snug...

...she did clean it after all, didn't she?

...maybe just to rest for the night.

Get through the night and go back to trying to escape tomorrow.

It wouldn't be so bad.

...right?