Another quick 30-ish minute challenge for the morn.
 
 As always, any and all feedback is highly appreciated!
 
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 The Dangers of Gambling!
 
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 Theo was sitting in his comfortable gaming chair in his room playing one of the newest shooter games on the market. With an allowance such as his it wasn’t a problem to just take a walk down to the local video game store and pick up even newly released games. It wasn’t as if he had anything else to spend his money on these days. Well… except for one thing.
 
 Theo shifted a bit, and let out a small gasp as he felt the large plug that he had in his ass, shift around, and put a bit of pressure on his p-button. Despite his attempts to stifle the moan, it still went across the mic he had in, meaning his teammate definitely heard that.
 
 It got a small chuckle from his teammate who had convinced him it was a great idea to wear a plug while gaming together. Of course, XXX_Hijacking-Sissy_XXX was doing the same. And Theo had the pics to prove it as well.
 
 As they were making their way to the next engagement, Theo thought of the plug that Hijack apparently had in. The thing was massive. Not as big as a fist but it had certainly been getting there. He’d been sent two pics, one with it out, showing off just how big the plug was compared to his closed fist, and one where Hijack had his ass in the face of the camera and the end of the butt plug firmly in his large, smooth, and white ass.
 
 Theo had his in partially because he was curious, and mostly because he had lost a 1v1 versus him in the game’s arena mode.
 
 “You know it’s better if you lean back.” Hijack told him over the mic.
 
 “What?” Theo responded.
 
 “You should lean back, you wouldn’t want to get a hunched back now would you? Lean back. It’ll be fun, I promise.” Theo nodded despite Hijack being unable to see him, and straightened his back, and leaned back on his chair.
 
 Like before, Theo felt the plug rubbing the special place in his ass, sending a wave of pleasure through him, and making his already hard dick get even harder in his pants. He couldn’t touch his cock, they were in the middle of a fire fight with a squad in the game so he couldn’t even pleasure himself at all, except…
 
 Despite himself, Theo found himself shifting around on his seat as he leaned back, rubbing the plug in his ass more and more against his prostate, turning the quick wave of pleasure into a continuous emanation of pleasure. Theo felt himself start to breathe a bit more with his mouth as he both enjoyed himself on his toy, and lined up a head shot on an enemy combatant.
 
 “Enjoying yourself?” Hijack asked, and Theo blushed.
 
 “Yea, yeah...” Was Theo’s timid response. He heard a giggle come from Hijack.
 
 “Hey you know that thing that you said you had to do?”
 
 “Yeah?” That “thing” being something of a social gathering for the elite of Brockton in which they also brought their kids along.
 
 “Wanna make things interesting?” Hijack started to sound like he always did when he was going to try to do a bet with Theo, usually one that would have rather perverted consequences if he lost the bet. Theo spared a glance at his gamer tag. XxX_Sissy_Slvt_XxX, the consequence of one of their previous bets. Sure he could just not do it but then it wasn’t like he had many friends who would ever see it.
 
 “If you get MVP in the match, I’ll let you change your name back to what it was before. If you don’t end up MVP, you gotta wear that plug and send me a pic of your cute ass all plugged up while at your thing, okay?” It was a tempting offer… Theo checked the leaderboard for the match. He was in second place for the entire team. He was already doing well as MVP if the match continued on like this. Theo smiled, excited at the chance to change his name back to what it was before.
 
 “Deal.”
 
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 “Sit up straight.” Theo’s father, Max Anders commanded, and Theo, reluctantly, sat up straight, accidentally shifting the butt plug in his ass up against his prostate, sending a wave of pleasure through him, and making his cock strain in his pants.
 
 Theo lamented his situation. He hadn’t even had time to cum. He’s just barely been beaten out for third place by some guy named Void_Cowboy, and so not only was his gamer tag still XxX_Sissy_Slvt_XxX, but now he was stuck at this event with a butt plug in his ass, constantly making pushing against his prostate, constantly making him shift around, accidentally causing the plug to rub up against his special place more, and causing him to leak out pre-cum in his pants.
 
 He hadn’t even had a chance to masturbate as his Dad walked in just as he was finishing the game and told him that they were leaving in five minutes and to get ready. Hijack had heard all of this and had laughed at Theo’s predicament. It didn’t help that he had accidentally leaned back in surprise when his Dad had swung open the door, causing his plug to rub right up against his prostate, sending an especially intense wave of pleasure through him that had his cock twitch.
 
 Theo felt a vibration from his phone and picked it up. Seeing that it was from Hijack, he leaned back a bit more, rubbing the plug against his prostate some more and checked the message.
 
 “Check in time lil’ boi!” Alongside the text was a pic was an image of Hijack with his ass in the camera, showing off that he also was still wearing his massive butt plug. In the background, there was also a blond girl with freckles with the face that showed both surprise, and outrage at Hijack’s rather brazen behaviour. Maybe his girlfriend or sister?
 
 In either situation, Theo resigned himself to what he had to do, and excused himself from the table to head to the men's room. Trying his best not to walk funny because of the plug that was in his ass. 

Empire's Heir (Worm)
 
Theo Anders has reached the age when boys like to experiment, now if only his father wasn’t a Nazi.
 
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 “Mmmmhmm,” the girl on the screen moans as a dildo enters her, giving off the impression of great pleasure. Intellectually Theo knew that it was probably exaggerated. However in the hormone and lust laden mind of Theo there was little difference. He was enraptured by the slutty girl on his screen. The rapid thrusting of her large dildo, her full ass, latex clad arms, legs, and her small pink chastity cage.
 
 As the chastity cage and the flaccid dick inside of it indicated that this person was not a man but rather a trap. A passable trap but still a man nonetheless. None of his family nor their associates would approve of what he masturbated to.
 
 They would approve of what I’m about to do even less. He thinks as his gaze moves over to the sleek black tower of rubber. Standing tall and lubed up with hand lotion is Theo’s largest black butt plug. Tall, thick, and so far his favourite toy. When he had used the plug before he had felt something pleasant as he thrust it in and out of his ass while rubbing his meat. Slowly in the months prior he trained his ass with smaller plugs and dildos until he could fit the large thing in his hole. It gave him more pleasure then his usual method of ‘releasing pressure’ and gave him something more to focus on than just his dick.
 
 Theo slows the hand pumping his meat as he feels himself get close to the edge of orgasm. That failed to slow the oncoming rush however so he reluctantly took his hand off of his dick. Still his hand hovered over it ready to pounce once more unto his rod should Theo’s control slip. Though he knew that greater pleasure was to come if he could hold out. The rising orgasm faded away without spilling over. Finally moving his hand away from his dick he reached out for his plug, then lowered it down to his ass. Using his toy Theo slowly began to tease his hole.
 
 Unlike the trannie Theo was watching he didn’t immediately take the plunge with his anal toy. Rather he circled the hole he intended to enter. It would go in fine he knew. Since while he had been edging he teased his hole a bit with a lubed finger or two, never able to do much more than stretch himself out. The stretching however did prepare him for this, pushing in Theo felt the plug enter into his ass. It was just the tip of the tall plug but already it stretched him more than his smallest plug ever could. His hole clenched down on the intruding rubber. In a second he could push it in further but for now he would just appreciate the pleasant sensation of the toy entering his hole.
 
 Soon it wasn’t enough however as he begins once more to stroke his cock and push the plug farther in. Theo feels his ass gradually being stretched out as the plug travels once more into his explored depths. He feels the end of the plug coming. He slows his plugs advance into his butt expecting the somewhat painful stretch that usually accompanies him trying to get past the plugs widest point for the first time in a session.
 
 Nothing. Or atleast no pain as the plug slots itself into his rear, there was only the pleasure he associated with the action. He had still felt a stretch, but like when he first put the toy in it was a pleasant kind, a little spark of bliss. Theo pulls his toy out a bit moving the thickest part of the plug out of place and causing him to feel that spark again. His left hand picked up speed with the plug as he strokes his prick, the video at the same time also reaching its climax as the scene changed to the trap being pounded by a fucking machine at high speed.
 
 The slutty moans from the video sounds loud even with its volume down to the lowest it could go without it going completely mute. It didn’t matter though to Theo as he thrust with his plug and strokes his cock. Little zaps of pleasure with every thrust in and out. His pumping speeds up again going from the quick and methodical in and out that he started with to the quick blissful pleasure of rapid fire thrusting he usually ended his sessions with. Pushing the toy one last time into his ass Theo hopped that he would get something more than just the little pleasure zaps he felt, but to no avail.
 
 Quickly however he remembered the largest dildo that he owned. The one that he never had used as he had never been able to fit it in. Maybe he could now, after all he could now fit in his largest plug at its widest point. Why not the eight inch monster in his closet?
 
 Theo abandoned his stroking as he got up from his chair but left the plug in as he moved to his closet, reaching in and retrieving the monster. It was only a little thicker than his plug at its thickest so despite his multiple failed earlier attempts he should be able to do it. Squirting some lube onto the giant cock Theo plops the dildo down on an empty part of his room in front of the TV screen. From his ass Theo removes his favourite plug and places it over on his desk and fingers his now loose rump as he returns to the dildo on the floor.
 
 He lowers himself over the cock and with his hand guides it towards his rear. The tip enters his ass sort of like his favourite plug from before today, mostly a pleasant sensation with a hint of painful stretching. However as he goes farther something changes.
 
 A wave of bliss shoots through Theo as the rubber dong went farther in. His mouth opens and a quiet ragged breath comes out involuntarily. It was hard for Theo to describe the sensation from his ass but he knew he wanted more. Quickly Theo began bouncing on his bent legs, eyes up to the ceiling, video completely forgotten. Quickly his knees began to ache and quiver as he lifts his admittedly pudgy frame over his dildo. This wasn’t the quick pleasurable zaps of his plug but a whole new sensation. It wasn’t quick enough! He needs more as he forces his already tired legs to bounce him higher so to let him come down harder. His hand strokes his dick fast and hard as he feels himself begin to be overwhelmed by the waves of pleasure coming from both his bouncing and the quick strokes of his painfully engorged glans.
 
 With one last descent onto the thick cock and one last pump of his own dick Theo feels himself explode. He is suddenly very still as he rests on both his heels and the pillar in his ass. His breath is still raggedy but he feels his good mood infect his breathing, coming out more as an out of breath laugh than true respiration. The video is still going but it is the last thing on Theo’s mind as he slowly lifts himself off of the dildo. He uses his arms to help himself as his legs feel weak from possibly the best orgasm that Theo had ever had. Fearing he would collapse Theo stumbles over to his bed, feeling like at any moment his legs would collapse out from underneath himself. Theo lays on his bed for a moment. He rests his legs and basks in the aftershocks he feels from his first rough dick ride. Slowly his strength comes back to his legs and picking himself up from off his bed he gently plucks his monster dildo from the floor. Packing it in it’s hiding spot Theo thinks as he starts to hid the evidence of his degeneracy.
 
 I think I have a new favourite.