Jacki’s Pleasure Winning Her Back chapter 10 by Hero_For_Hire

The evening goes by quietly. Jacki seems content to leave Jack on the kitchen counter, and Jack is more than happy to be left alone while she watches TV and indulges in a glass of wine or two… or three, or four… 

He assumes he’ll be spending the night on this counter too, and tests the bread’s viability as a mattress. Spongy… he shrugged, it wasn’t the worst place he’s had to sleep.

However, as the evening gives way to night, and he tries to get some shut-eye, he’s overcome with the sense that he’s being watched. Opening his eyes and rolling into his back, he sees Jacki looming over him. There goes that pounding chest again…

“Um… hey.” Jack tries to sound casual. “You okay?”

Jacki doesn’t say anything for a bit. She just stares at him. When she does speak, it’s clear she’s had more to drink than just a few glasses of wine. 

“So, like… what’s the appeal here?” She rests her chin on the counter and narrows her eyes, inspecting Jack. 

“I’m sorry, I don’t know what you mean…”

“I meeeeaaaannn!!” She taps the counter as if she’s knocking on a door, rattling Jack into standing up. “How does Zoe get off on this?!”

“On… me..? Being small, you mean?” 

“Yes!” Jacki responds a little too loudly. Her erratic movements and clearly inebriated state make her a 200ft tall powder keg to Jack, who is hopelessly stranded and at her mercy. 

“You’d have to ask her, I guess…” Jack answers as diplomatically as possible, hoping she’ll drop it and go to bed. 

“Nahhh’m askin’ yooouu~” she prods him playfully with her finger. “What kinda stuff does she do with you?”

Jack recedes into himself. Not only does he fear sharing intimate details about Zoe (and her retribution if she finds out he did), he was also ashamed to share how she used him like a dildo, a mere object for her pleasure and then ignored for the rest of the night.

Jacki notices this reluctance. “Fine.” she says petulantly. “Don't tell me - I’ll just see for myself…”

Before Jack can ask for clarification, her hand reaches out and snatches him off the counter. Engulfed in her palm, Jack tries to thrash and scream but her grip is too fierce. He tries to bite her, but he’s so constricted he can’t even move his head.

Jacki carries him to her bedroom and tosses him onto the bed. He screams as he flies through the air, bouncing along her mattress several times before settling in the middle. He scrambles to his feet in time to see Jacki’s ass looming over him. He dives to the side to avoid her gigantic rump as it collides with the bed, and the addition of the new weight flings Jack once again. 

“Oops.” Jacki giggles. “You okay back there?” She calls over her shoulder. 

Jack stays down. He lays on his front, panting as the bed shifts beneath him with each movement Jacki makes. She plucks him off the bed by his leg and dangles him helplessly before her. She taken off a layer of clothing, leaving her in just her underwear.

“Jacki, wait! Please don’t! I’ll do anything else, but not this!”

Jacki lets her prey twirl around in her grip. She inspects his naked body and feels the flutters of arousal stirring within her. She starts to get what Zoe finds so fascinating about this; the power and control is intoxicating. Even the way Jack pleads with her is kind of hot…

She bites down on her lip and smiles as she runs a finger along the length of Jack’s body. Jack flinched and lets out an involuntary grunt as her fingertip runs along his penis. 

“Mmm…” Jacki purrs, bringing him closer to her eye so she can get a closer look. 

Jack sees his reflection in her pupil; a scared, weak man rendered powerless by his situation, the very situation he put himself in. He tries to beg for mercy once more, but his voice comes out in a whisper. 

“Oh, before we begin…” Jacki extends her arm so he can see her entire face. “If you tell Zoe about this, I will kill you.”

She doesn’t even say it like a threat. It sounds more like a promise, or an agreement between businessmen. ‘Here is the price for this action, should you take it.’ In lieu of a formal handshake or signing of a contract, Jack nods. He understands. 

He falls as Jacki lets him go and he silently descends into her awaiting panties, an entrance held open by her free hand. 

There was perhaps a time when Jack would’ve welcomed a drunken fling with Jacki. She was a beautiful young woman, if a little too fiery for Jack’s tastes. But this fantasy was always one he was content with remaining in his head; even then, the parameters of such an encounter relied on a few things. The first, and perhaps the most important, was that he be single. But the second most important thing  - and it’s a close second! - was that they both be normal sized. 

That was the kind of man Jack was. The kind of guy who’d fantasise about fucking his girlfriend’s best friend, the guy of guy who’d actually kiss another woman behind her back. 

As Jack found himself being rubbed into Jacki’s giant, slick pussy, he came to realise his place in the world. This was his life. A life he not only unwittingly walked into, but a life wholly suited to him. He wasn’t content to accept the consequence of his decision to cheat on Zoe, no. He had to go out and seek a more severe punishment. 

Jacki’s pussy quivered as it continued to coat him in her juices, greedily pulling him deeper in until he was fully submerged inside her. Jacki’s moans came quicker and louder, and she rubbed faster and harder. 

Jack was in Hell.