Return to Bowser's Castle (Princess Jessie)

Commission by

A follow up to this piece:

Having managed to escape the digitalscape that he was held captive and tormented in, Jessie once again now finds himself in the world of video games and once again wearing the princess outfit he was forced to wear before and in the familiar stone walls of Bowser's castle. Jessie was dumbfounded and nervous as he was not only wearing the now infamous outfit that he can only associate with his imprisonment and captivity, but was also behind enemy lines and deep within his tormentor's domain. Even worse, the castle seemed to be different than he remembered. While the style was familiar, the halls and layout were alien to him. Jessie spent his time as Bowser's captive (willing and unwilling) in various rooms and having to traverse the building to reach those rooms and various other parts and often in full bondage either being carried or having to hop in high heels with few cases he was allowed to walk with his leg's either free or shackled, but the rest of him securely tied and gagged. Jessie did his best to try and navigate his way around the castle to find an exit or at least one that didn't require jumping from a window 100 feet up and not over lava or jagged rocks. Many times, Jessie had to hide to avoid detection by Bowser's minions, the various Koopas, Goombas, and other residents of the castle. Jessie felt like he was making progress when he had to duck into a room to keep from being seen by a couple of patrolling Koopas and without seeing if the room was safe. While he waited in the dark and spooky room for the patrol to pass by, a presence revealed itself to be in the room with Jessie. A stalking Boo let out a haunting cry that startled Jessie. He pounced out of the room the to evade whatever it was that made the noise, having forgot what Boos sound like, and revealed himself to the patrolling Koopas. Jessie frantically ran as fast as he could in his cumbersome dress and high heels that he was not allowed to remove away from the Koopas, however he was not a fast runner as it was and having to run in heels only made his attempt at evasion only slower. The Koopas were also more clever than Jessie remembered as one tucked themselves back into it's shell while the other one grabbed the shell and hurled it at Jessie. The shell passed right underneath Jessie, taking his feet out from under him and causing him to fall flat on his butt onto the tile floor. Jessie cried out in pain rubbing his butt from the stinging impact. He couldn't pay any more attention to it however as the Koopas had closed the gap on him and now surrounded him. Jessie darted his vision to find something to bail him out. A weapon, an object to throw at his pursuers, a door or window to jump through. Unfortunately, for him there was nothing for Jessie grab or leap to to save himself as the Koopas jumped him. After a brief tussle the Koopas had Jessie subdued and carried into a nearby room to properly make the pretty femboy their captive. Somehow they produced ropes and scarves and proceeded to tie up and gag the poor pretty boy. Jessie struggled and fought as best he could, but he wasn't much of a fighter and was weaker than his assailants. They were easily able to secure him tight with ropes to keep him under control and stuff and cover his mouth with scarves to silence his cries and pleas to be let go. Now all Jessie could to was wriggle in his bonds and whine and whimper into his gag. It was happening all over again. Jessie was being forced to become a helpless captive and damsel in distress all dolled up as a pretty princess and once again to be tormented by the King of Koopas, Bowser. Jessie was filled with both a sense of dread and excitement. Jessie truly didn't want to return to this fate, knowing fully well what being held captive in bondage 24/7 did to him last time. He feared becoming a willing captive and aiding Bowser in his nefarious plans again and becoming his doting and loving Queen once more. Once again however, he felt the swell and comfort and arousal come over him as his naturally submissive instincts began to take over, turning his genuinely fearful and frustrated cries for help and struggles to free himself into weak and pathetic wriggling followed by pleasured and eager muffled moans. He greatest fear of returning to this place and this fate was now becoming his greatest fear of desiring to remain in captivity and to please his master in any way he desired. He also feared that fear would vanish and all semblance of his non-submissive self would be permanently exorcised from him and he would forever willingly remain bound, gagged, and helpless in service to his monstrous master.

Many thanks to for this fantastic artwork! I'm so happy with how this came out. I just love these pieces of Princess Jessie being subdued and/or tormented by these dastardly Koopa minions. ^_^

Art by