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Chapter 106
by
Bigbop38
What’s Jim got planned?
Some anal action for Sylvia.
You begin to slightly pick up speed, still thrusting slowly into Joy’s vagina as your erection returns. If you understand Jim’s implication correctly, things are about to get… interesting for Sylvia.
The pale woman on screen gulps, then smiles nervously. “Are you sure I can’t convince you to use my pussy? It could really use a good dicking!”
The tanned giant grins at his prize’s attempts to bargain. “Well, we can talk about that after the forfeit. Maybe head back to my room together. Though I may need to carry you, since you probably won’t be walking after this. For now, though…” The man crouches and hands her the bottle. “Lube up my cock. Then your ass. Be thorough.”
Closing her golden eyes and inhaling deeply, the blonde takes the bottle. Having steeled her resolve, she opens her eyes once more and sets about her task. As the bearded man stands back up to his full height, Sylvia takes his pulsating member with one hand. It’s still slick with her saliva, but that’s far from enough for this task. The wispy girl squirts out a large glob of lube onto Jim’s shaft, nearly half the bottle, then sets about rubbing it around. As she makes sure that the entirety of that massive schlong is coated, you can’t help but picture a prisoner being made to sharpen the headsman’s axe.
Sylvia then lubes up her right hand, before moving it around her back and down to her rear entrance. She works fast, clearly no stranger to anal, slipping a lubed finger inside. Then a second. And a third. The small woman is clearly doing what she can to stretch herself, to prepare for her anal execution. She moans lightly as she fingers and stretches her anus, working quickly since she doesn’t know how long Jim will give her. Panting softly, the girl continues to push further, slipping a fourth finger into her spreading hole. This is absolutely not the first time this hole has been stretched so wide; people who defeat her probably love to do so, to see how far they can push her since she’s so small. It takes nearly fifteen minutes, but eventually, the platinum-blonde is essentially awkwardly fisting her own ass, her lubed hand now completely inside.
The fiery-haired man, who has been watching her with a grin this whole time, holds his hand out and speaks. “Give me the bottle and stand up. I’ll finish the prep work, then we can begin.” Wordlessly, lust and fear waging a war in her eyes, Sylvia complies. Jim applies some of the oily liquid to two of his meaty fingers, and sets about digging into the pale blonde’s backdoor.
She gasps, and lets out a small moan as his thick digits press into her. “Jim… Just your fingers are… Oh, fuck, how am I gonna do this?”
“I’ve seen you take plenty of big tools up there before. You’ll be fine.”
“Not that big. Or deep… Hey, can you at least… go slow? Pretty please? I haven’t been that mean to you, have I?” The golden-eyed woman makes those eyes as doe-like and sweet as she can, staring up at her friend pleadingly.
The big man chuckles. “Oh, I don’t actually mind the teasing. It’s fun. But, you still need to be punished for it, Ms. Mouthy.” The girl’s lips quiver, and Jim speaks again. “I could be convinced to start slow… if you agree to come back to my room tonight.”
Sylvia nods vigorously. “Yes. Done. I’m yours all night. Just please, don’t completely destroy me?”
“Deal. Now, one last thing…” Swiftly, the titan of a man lifts the petite woman up by the waist, then flips her upside-down. “Let’s use it all, yeah? Probably for the best.” His green eyes twinkle as he upends the bottle of lube into the woman’s bowels, coating them with slick fluid. “Alright, here we go. Sorry for the delay everyone, but without further ado…” Jim flips Sylvia right side up again, facing away from him. Lining her pucker up with his throbbing pole, he begins to slowly lower her down. The woman bites her lip as her anal spearing begins, doing her best not to tense up. The crown of the tanned man’s huge penis presses against her pucker, then pushes in. The small blonde gasps, and you and Joy both marvel at the sight of her tiny body being slowly pierced, spreading far wider than it is meant to. One inch at a time, the fiery-haired man’s dick disappears inside the pale woman’s rectum.
Her face is amazing to watch. It starts steeled, with both nerves and excitement flooding her golden eyes. Then light surprise flashes across it as the penetration begins, before it shifts back to resolute. With every girthy inch, the blonde’s golden eyes grow wider and wider, her breath coming quicker and mascara-streaked face reddening more and more. Her breath starts to catch, and her eyes look like they are about to bug out of her head as the man finally hilts himself inside of her colon, groaning in satisfaction.
“How’s that feel, slut?” The giant asks teasingly.
“S-So full. Never been so full. Hard to breathe. HaaAAhhAh.” Sylvia’s tear stained, reddened, shocked face is the center of the shot right now, and you and Joy enjoy every second of what you’re watching. This is easily the most odd sex you’ve ever had; it barely even feels like sex. You’re just using the white-eyed nurse for your pleasure, thrusting into her without looking at her. She’s treating you much the same way, like you’re an automatic dildo that’s fucking her while she watches porn. The newness, and strangeness of this is a thrill in and of itself.
“Well, like I said, I’ll start slow. Here we go.” Jim pulls the small woman halfway off of his cock, and she begins lightly moaning as he does. The bearded man then starts thrusting up into her, gently moving his absurd length in and out of her tight hole. The golden-eyed girl begins twitching, spasming almost, as she is penetrated repeatedly by the man’s massive fuckstick. Her breath only comes in small gasps, and her moans start to ring out loudly as she stares at the crowd. They’re all watching her get ass-fucked, and pleasuring themselves or each other all the while. The exhibitionist manages a smile, and holds up two peace signs with her hands. “Oh, does that mean you’re ready for a little more?”
At Jim’s words, the platinum-blonde’s eyes widen. Before she can speak, the built man begins speeding up his thrusts, moving from very slow to a medium pace in an instant. “Wh- FUCK! JIMMMM! THA-THAT’S-“ She doesn’t manage to finish her sentence, and instead starts moaning wildly as her victor pumps in and out of her tight rear with his fat cock. Her golden eyes glaze over and she starts making near animalistic noises as she endures her forfeit, pussy juices dripping and flying whenever the man thrusts into her ass.
This continues for a half an hour, the fiery-haired giant steadily ruining the alabaster-skinned girl’s anus. Sylvia’s face is unrecognizable now; totally red with black streaks running down it, eyes hazy and not looking anywhere specifically, mouth hanging open in a silent scream as loud moans occasionally escape. There are several times where a sudden gush of fluid leaves her vacant cunt, signaling that she’s cum from anal stimulation alone. And from the audience watching her, most likely.
Jim, who’s breathing is even, speaks up. “Are you enjoying yourself bitch? Getting your asshole obliterated in front of all these people? On live TV?”
His prize replies shakily. “Yesss. Feels so good… Your fat fucking cock, splitting me open… I hope… everyone is watching…”
“Glad to hear it. Time to get serious.” Without any further warning, the 12 inch rod in Sylvia’s ass picks up speed. The green-eyed man begins fucking her with reckless abandon, slamming his cock into her over and over. The woman screams, her eyes rolling back into her head as her pussy squirts with every thrust. Loud slapping noises echo through the arena as his hips repeatedly slam into her modest cheeks, causing the flesh to ripple as the petite woman moans and cums unendingly. You’re fucking Joy at a similar pace, slamming into her and breathing hard. Both of you came an additional time during the thirty minutes of earlier ass-pounding you were watching, and you are now rapidly approaching your third orgasms. Squelching sounds fill the room, your two previous loads of semen being stirred as you thrust. The quiet nurse is now moaning loudly, enraptured by the show being put on.
Jim is grunting, his own breath coming in ragged gasps as he is finally nearing release. With swift movements, the large man flips Sylvia around to face him, kissing her once before crouching down and releasing her. He balances the small woman upside-down, on her shoulders, and puts her in a mating-press. There’s no mating going on here, however, just an ass-reaming like no other. The petite blonde is now coating herself in her own love juices, grunting and groaning as she gets pounded.
“Getting close, slut! Get ready to be filled up!” The bearded man roars, and the fucked-silly woman can only moan in response. With a final grunt, Jim hilts himself inside of her, his body jerking slightly as he pumps an incredible amount of hot cum into the girl’s body. His grunts become low moans as his climax continues, not seeming to stop. More and more sperm is shot into Sylvia’s bowels, rope after rope filling her up. It just keeps going until, unbelievably, her stomach swells ever so slightly, showing the world just how full this woman’s stomach is. With one final sigh, Jim pulls himself out of his tiny lover, whose lower half flops to the ground, her gaping anus instantly leaking semen onto the arena floor.
You finish inside of Nurse Joy for a third time, and she clenches down on you hard as you do. She lets out the loudest moan you’ve heard from her, the loudest sound you’ve heard her make. You’re both sweaty, twitching in the aftershocks of pleasure as you breathe hard. You lay down on top of the pink-haired woman, and she sighs comfortably under your weight.
“That was INCREDIBLE!!! I hope everyone enjoyed that! Let’s all give a big round of applause for James and Sylvia, what a show!” The crowd erupts into tired cheers at the announcers words, all slightly exhausted from the over-an-hour long forfeit. And all the ones earlier in the day! Jim has plopped down on the ground next to the blonde, and is lightly stroking her hair. This is the last shot you see before the program cuts away, switching to a talent desk to review the match and discuss the rest of the tournament.
What a show indeed.
What’s next?
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Pokeslut
Busty rookie pokemon trainer gets fucked (Public)
An all new Pokemon adventure awaits you in Kanto! Will you become a Pokemon master surpassing your long time rival, or will you be left to smell him later after he fucks the ever living shit out of you! (Public)
Updated on May 18, 2026
by Delta12
Created on Apr 6, 2019
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