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It wasn't often that Chester got bored; after all, he had the world in his hands, and he used that to make everything more fun.
Even in his private moments.
His work at the candy shop was an example of fun, especially when he managed to play the best pranks on Mandy. Her cheeks inflated like little red balls, her nose twisted into the cutest scowl he'd ever had the pleasure of seeing. When her screams echoed through the castle and the illuminated beams of her shots followed him, Chester's adrenaline made his blood boil through his veins. He was euphoric and had more fun than he should have with this little game of cat and mouse.
That's why he got rid of his jester costume as quickly as possible when he got to his room at the end of the day, suffocating from the heat (and the blood on his cock) that had built up over the day. He flopped down on the bed and watched his cock curving over his abdomen, hard and very much in need of a little attention.
Well, his box of surprises served many purposes.
He thought about how rude Mandy could be to him and his fingers stroked around his cock. She would surely make him pay bitterly for every one of Chester's pranks, her hatred so great that she would close her fist around his cock and repeat constant jerky movements, aiming to break his pathetic length. That thought made Chester's cock throb in his hand, and he arched his hips, fucking into his fist.
Lawrie could also be bad. Of course, he was the bad cop after all.
Chester's free hand rummaged through his box and pulled out a thick dildo that resembled Lawrie's cock. It wasn't metallic like his, but it was similar in length.
He thought about how Lawrie would grab him by the hair and throw him against the wall of that interrogation room, pressing his body against his. Oh, so mysterious. Chester bathed the toy in a lubricant he'd also taken from the box and rubbed it against his cock, feeling it throb with each rub. His hips thrust against the firm, vibrating material, and Chester bit his tongue to hold back a moan.
His fingers traveled down his perineum and found his hole, thinking now of how Draco could easily grab him from behind and fuck him until his senses became fuzzy. Draco from behind and Lawrie from the front—both dicks meeting inside him, rubbing against each other as they thrust deep enough to make Chester scream. His insides would be completely filled, and his body would press between them. Hearing the moans of both of them so close to his ears would bring him to a climax at an embarrassing speed.
His prostate was poked, making Chester roll his eyes and thrust his hips so that his fingers went deeper. He thrust them deep inside him, also accelerating the speed at which the vibrator moved against his cock. The stimulation was so intense that he felt like he was going to pass out at any moment.
But what would really make him pass out was Berry's huge cock. If he could have it inside him, fucking him like a cheap whore, Chester was sure he'd cum in seconds. He pulled his fingers out of him, his trembling legs barely able to stay in place, and went back to rummaging in his box.
What he pulled out was a string full of small shiny balls similar to the bells on his hat, but which would work as a kind of anal beads. The existence of the bells of different sizes would surely help to form the exact size that Chester imagined Berry would be. He spread his legs wide and tilted his hips to receive each of the bells in his greedy hole, leaving the vibrating toy halfway up his cock to travel his free hand over his stiffening nipples in search of more stimulation.
The one who would love to overstimulate his nipples with clamps and other tricks that only she knew was Charlie. They had known each other since their teen days, so Chester was already familiar with how cunning that spider could be with her mouth and fingers. She would circle both nipples with her tongue and nibble them gently between her teeth just to tease.
This made Chester pinch his nipple, starting to pull the bells out and then pushing them back in. The way his insides tightened around their plump shape made Chester see stars, his body on fire from each of these stimuli, and his vivid imagination taking him straight to all those he dreamed about.
He threw his head back against the pillow and curled his toes, getting closer to that delicious pressure on his balls that warned him he was close. His jaw dropped in a loud groan as he pushed all the bells inside him and his inner walls tightened around them, thirsting for more of the addictive sensation of the bells teasing his insides with each pass.
Everyone he dreamed of would love to torture him like this, that much he was sure of.
Mandy would love rubbing that little vibrating toy on him and forbid him to come, forcing him to beg for it; Lawrie would fuck him without the right to vocal opposition until he learned his lesson—his mouth and ass would be full of him anyway; Draco would be the same, but gentler, appealing to his relaxed side by fucking him out of his body as gently as possible; Berry would be aggressive and leave his skin scarred with slaps and hickeys. He would mark him to show Chester that he was his alone and nobody else's; Charlie could peg him, and Chester certainly wouldn't complain about having her deep inside him while he was held down by her tough spider webs.
A scream escaped his throat and Chester stopped thrusting the anal beads into himself, feeling his climax hit him with the force of a truck. His cum poured down his abdomen and splashed a little on his jaw and collarbone, painting his flushed skin with his guilty pleasure. The vibrating toy remained switched on against his cock, even though it was so sensitive that it hurt. Unfortunately, Chester didn't have the strength or breath to turn it off now.
And who knew, maybe he'd be ready again for another round?
After all, he had the world in his hands.