Empire's Heir (Worm)
 
Theo Anders has reached the age when boys like to experiment, now if only his father wasn’t a Nazi.
 
 \+.+/
 
 “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.