Chapter 11
by
lustquilll
Does he go for sloppy seconds?
Of course he does
His mind screamed no. Every fibre of his being recoiled from the idea of trying to follow Leia’s act. It was suicide. It was an invitation for more humiliation, more crushing evidence of his inadequacy. But the words were already out, almost involuntary. “Yeah,” he rasped, his voice rough. “Yeah, I can go again.”
A mischievous glint danced in Sara’s eyes. “Well, don’t keep me waiting, big boy.” She tossed Leia’s condom onto the bedside table without a second thought. It landed with a soft, wet thud, a stark reminder of the monumental act that had just transpired.
Jack swallowed hard, his hands trembling slightly as he reached for a condom from the packet on his side of the bed. It was a standard size, the kind he always used, perfectly adequate for his modest dimensions. He fumbled with the wrapper, his fingers clumsy, and then rolled it down his already thin, four-inch cock. It felt almost comical, this flimsy sheath, compared to the heavy, engorged one now lying discarded.
He moved over her, his entire body rigid with a mix of dread and a faint, **** hope. Maybe, just maybe, he could make her feel something. Maybe he could erase Leia’s touch with his own. He positioned himself, his eyes searching hers, but she was already closing them, a sigh of anticipation escaping her lips.
He pushed inside her.
The immediate sensation, or lack thereof, was a shock. Sara, usually tight and responsive, felt… cavernous. Loose. Ruined. Leia’s massive, thick veiny cock had stretched her, dilated her, accustomed her to a size and pressure that Jack’s modest shaft couldn’t even begin to replicate. He felt like a pencil in a bucket. There was no grip, no friction, none of the familiar, comforting tautness that usually promised at least a modicum of pleasure for him.
He began to thrust, trying to imitate the deep, powerful strokes she had earlier praised. He pushed, harder than he ever had before, trying to reach the depths she had spoken of. But it was like sailing a small dinghy in a vast ocean. He felt lost, adrift, insignificant.
Sara’s initial moans of anticipation quickly faded, replaced by tiny, confused murmurs. Her brow furrowed slightly. “Hmm,” she hummed, her eyes still closed, a puzzled frown beginning to etch itself between her brows. “Jack? What’s… what’s going on?”
He kept thrusting, ****. “What do you mean?” he managed, his voice strained.
Her eyes fluttered open, dark blue and searching, now clouded with a definite disappointment. “You feel… so much smaller, baby,” she said, her voice laced with an almost childish complaint. “And I can barely feel you. What happened? Where’s all that… bigness from before?” She shifted her hips, trying to find a better angle, a more substantial purchase, but it was futile. “Come on, Jack. Fuck me deep, like before! Push, baby, push! Really get in there, like you were just now.”
Each word was a hammer blow. Smaller. Barely feel you. Fuck me deep, LIKE BEFORE. The phantom of Leia’s monstrous cock loomed large between them, an invisible wall of flesh and power that Jack could never hope to penetrate, let alone surmount. The humiliation was a raw, burning fire in his gut. She was literally begging him to be someone else.
He redoubled his efforts, gritting his teeth, sweat beading on his forehead not from exertion, but from sheer, agonizing shame. He tried to push deeper, to mimic the powerful movements, but his small frame and thin cock were simply not built for it. He felt nothing but air and the slick, empty cavern of her stretched pussy.
Sara sighed, a sound of utter exasperation. “Is something wrong?” she asked, her voice tinged with concern, though the underlying annoyance was clear. “Are you… tired? Is that it? Maybe you’re just not as hard after that first session. It was pretty intense, I guess.” She tried to reassure herself, to make excuses for him, but her body language screamed frustration. She tried to guide him, her hands on his hips, but it was like trying to steer a toy boat in a hurricane.
The lie, the convenient excuse, was a tiny reprieve, but it did nothing to assuage the gnawing inadequacy within him. He was hard. Just catastrophically outmatched. And then, as if on cue, his body betrayed him completely. The familiar, unwelcome tingle, the quickening pulse, the inevitable surge. He felt a pathetic shiver, a tiny release, a mere trickle of sperm into the regular-sized condom that now felt even emptier than before.
He pulled out immediately, his face flushed, his eyes unable to meet hers.
The End for now
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The Boss' Hammer
Jacks decisions
Terrible financial decisions have left Jack in a impossible situation. Does he leverage his beautiful wife Sara to his well endowed Futa boss to keep his job.
Updated on Oct 23, 2025
by lustquilll
Created on Sep 10, 2025
by lustquilll
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