Princesses in Peril

Another entry into the story of Princess Jessie, this time with the art drawn up by the great who does not apologize for her greatness.
Since seeing her art work, I've wanted to get a commission from her and having recently started supporting her through Patreon, I took the opportunity to hire her.
I was currently thinking about the evolving story idea I had thought up of Jessie taking Samus's place in the plot of 's old Systems of Entertainment idea where Samus Aran found herself in the role of damsel in distress instead of hero, taking Princess Peach's place as Bowser's captive. In my version, Jessie finds his way into the video game world just in time to rescue Samus, but instead of escaping with her, offers to take her place as a diversion while she escaped and tried to find a way to foil whatever plot Bowser had cooked up. Secretly it was also a chance to play damsel in distress for real in one of his favorite games and as one of his favorite roles. Eventually, he would be discovered to not be the real Samus and would find himself a true captive in his own right as Bowser kept him under strict restraint and in his company at all times. Bowser didn't need to just keep him safe and out of sight like Samus needed to be. Bowser could keep Jessie in full view and do with the pretty boy as he wished. At first he tormented Jessie and treated him like a trophy. Kept bound and gagged at all times and wearing either the princess dress he originally wore or some variation of it, often a more scantily clad/skimpier version of it. This was all to demoralize and humiliate Jessie, but Bowser was surprised that it had the opposite effect on him. Jessie seemed to be enjoying his captivity more than he thought he would and when granted the chance to speak, offered to be a willing captive. This was a bit new to the King of Koopa's as he always had to force Princess Peach to be his captive (even though my own personal theory suggests otherwise ).  He liked the idea though and gave Jessie a chance. Jessie proved to be not only entertaining, but useful as he would sometimes give Bowser advice and it was more often than not very helpful. This prompted Bowser to make Jessie a co-ruler given his way with not only Bowser's subjects, but his kids too. They all seemed to regard Jessie as a surrogate mother, more so than they ever considered Peach in that role. Bowser even found himself liking Jessie on a more intimate level and considered even making the pretty boy his queen, so to speak.
For now the two are partners and have conspired together in ruling the Mushroom Kingdom. But first they needed to recapture a potential threat in Samus Aran. With Jessie's knowledge of the game world and the character, Bowser's forces managed to capture a still Powersuitless and Princessified Samus. Jessie also thought it would be a good idea for him to keep an eye on Samus and possibly sabotage any attempts to escape she might make by having him back in his role as captive and kept bound and gagged with Samus. Upon her return to Bowser's castle, again as a prinsoner, Samus's attire was changed to something more flattering (or embarrassing depending on your point of view) and put her in heavier bondage than she was before. Upon being carried into what she thought would be her own private cell, she saw Jessie, wearing something similarly skimpy and bound and gagged in heavy restraints like her. Jessie played up being the helpless damsel which Samus ate up, immediately showing great concern for her initial rescuer. She couldn't ask him or even get a coherent response with the both of them heavily gagged, but she could only assume Bowser had been doing unspeakable things to him. It angered her as well concerned her for what might she might find herself subjected to as well. The Koopa minions left the two for a bit to get reacquainted, as best they could only being able to "mmmph" their speech. It wouldn't be long before Bowser arrived to greet his new guest again and also help play up Jessie as his captive and keep Samus's trust in him in tact. He taunted the two quite a bit, even threatening physical harm and torture on them. Samus was more scared for her feminine male ally than for herself. Even though she imagined he had endure  some amount of torture and torment by Bowser, she still saw him as a bit of a marshmallow and had likely only endure it because he had no other choice. Still she respected him for not breaking. If only she knew...
To play things up a bit more Bowser decided to have Jessie taken to his dungeon for "interrogation", leaving Samus alone and under guard to worry about Jessie and their situation. Bowser also thought it might serve to convince Samus to not make any attempts to escape as Jessie could suffer the consequences more than she would. Jessie did his best to keep from smiling or looking like he was enjoying himself (except when Samus wasn't looking at him) and did a great job convincing everyone he was truly a damsel in distress and being held captive against his will when Bowser carried him away. Once they were far enough away from Samus that she wouldn't hear them, the two laughed it up a bit enjoying the performance they just put on for the bounty hunter turned damsel in distress. At first Bowser was going to just keep Jessie in his room for a couple hours before bringing him back to his and Samus's cell, but Jessie insisted they keep it as real as possible and that Bowser should torture him anyway. "This deal is getting better all the time," thought Bowser to himself.

So, I was inspired to have this pic drawn up towards the very end of the story since I was planning to ask Heart to draw up the other installments in future Benefactor sessions (IE sketch and chat where she draws up a request from her higher tier supporters). I imagined at this point Bowser was used to Jessie's kinky ideas and would be inspired to keep Jessie dressed in something provocative for his captivity and opted to have Samus wear something similar. Since Samus's dress is more or less fused to her through the game's "rules", it made sense that if both of them were to wear something different that it would be in a similar color scheme and design to their dresses. So, I imagined them in lingerie/fetish attire in the same colors and designs of their dresses to accent their captivity a bit more as something more akin to bondage slaves. Of course, they had to have those awesome shoes Heart designed for the dresses. Afterall, what better design for a shoe than one the captive can't kick off because it's bound to their feet? Armbinders were a must and D4phnaie came up with the idea for the frogtie straps. As for the gags, I thought panels would be good as they could do a good job of gagging the pair and showing off their own personal emblems like how I imagined Samus would put her own logo on Jessie gag initially. Instead, this time they have their own logos on their own gags. Given they have similar appearances, this a good way to tell them apart.

So many "thank yous" to for drawing this and for doing such a wonderful job with my idea. I truly adore it and love it! ^_^
And many "thank yous" as well to for the inspiration for this story and letting me play around in her original idea.



Jessie © Me ^_^

Samus Aran and Bowser © Nintendo

Princess Samus and Systems of Entertainment concept by

Art by