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For awhile since I created Princess Jessie as an inspiration from 's Systems of Entertainment, I've wanted to try and create a scene where Jessie and Samus get to interact with each other similar to how he was introduced into some fanart drawn by Heart herself:

I was able to get something like that but depicting a later event where Samus is recaptured and joins a still captive Jessie who is started to develop loyalty to his captor in a bit of Stockholme's Syndrome, artwork courtesy of
This piece is a slight retelling of the original concept for the Princess Jessie origin where both he and Samus find themselves as helpless captives of Bowser and after their first meeting together, they're left by themselves to "get to know each other better". Now, I'm sure a couple of bound and gagged damsels can have some fun "conversations" together to pass the time, but Samus wasn't all that interested in small talk and was itching to get herself free. It took a bit of time to get Jessie to understand that she wanted him to help her escape, but once he realized what she wanted, Jessie used his knowledge of rope bondage and escape artistry to free himself. Once he was loose he began to untie Samus, who was a bit flustered that Jessie didn't try to untie her first while also being tied up himself (perhaps in some desire to be the one to free the both of them and look a bit heroic in front of her weaker ally) and that she was now at the whim of a smaller and weaker person. Being rescued by a man, let alone a feminine one probably didn't make her feel any less useless at the moment as up until that point she was so secured all she could do was struggle and whine into her gag. It was a sense of desperation and helplessness she hadn't felt in a long time and it was certainly a new form of helplessness she'd never experienced before. She was determined to get some payback on Bowser later once she'd gotten out of this world or at least could get back into her powersuit. For now she was going to have to rely on this femboy to assist her. As for Jessie, he was just enamored to be in the presence of his favorite character and one of his first video game crushes. Being able to play damsel in distress with her was already a dream come true as was being able to play hero for her, if ever so briefly. He kind of hoped maybe something might develop between them later on, but now wasn't the time for flirtations. It was time for a daring escape!