This is a continuation of a piece I commissioned before of another Jessie adventure into a video game world, this time in Final Fantasy 7 Remake, posing as a resident of the Sector 7 Slums and friend of Tifa Lockhart. Think of Jessie in this case as a replacement for Johnny in FF7 Remake, including his habit of getting into trouble.

Previously, Jessie attempted to infiltrate Don Corneo's Mansion when he learned that Tifa herself was infiltrating the mansion to attempt to get information from Corneo. He realized the only way he was getting in is if he offered himself up to be one of the Don's "girls" and went through a similar quest as Cloud to doll up and feminize himself up to convince Corneo's men and Corneo himself that he was a girl and worthy of being considered. Jessie even employed the help of the same folks who helped Cloud disguise himself. Once his transformation was complete he was able to convince the guards outside to let him in, with the help of a bit of flirting and sass to seduce the men. All Jessie needed to do now was find Tifa and help her escape. However, Jessie didn't know that his friend and her friends had already left, having been tricked by Corneo and dumped into the sewers below. Jessie was caught snooping and soon found himself trapped in Corneo's dungeon as his prisoner, as shown in the pic below:

Jessie manages to free himself thanks to an overly eager goon wanting to get handsy with the distressed damsel boy. Once free, Jessie learns that Corneo was working with Shinra thinks that Tifa and her friends would likely make their way to the Shinra building to investigate. Wanting to be of help still, he catches a ride up to the upper plates and to the Shinra HQ. Having been emboldened by his new transformation, Jessie decides to continue posing as a girl and disguise himself as an office worker. Unfortunately, that required him to ambush and subdue a poor secretary he could pass off as and leaver her bound and gagged in janitor's closet. Jessie was able to make his way up to the executive offices, searching for any sign of Tifa along the way, only to run into the head of the weapons division, Miss Scarlet herself. Initially, uninterested in the young "girl" she then recognized him in report that passed by her eye regarding a potential spy. The information came from Corneo himself upon learning his new "dungeon pet" had escaped and suspected the boy was working with Avalanche. Motivated to capture any spy, regardless of affiliation, Scarlet approached the femboy and inquired about him. Jessie did his best to pass himself off as the woman whose identity he "borrowed", but quickly realized the blonde ambitious executive wasn't buying it. So, he tried to pivot to the idea that he was just borrowing her badge because he couldn't get one himself. When asked about his gender, Jessie again tried to convince Scarlet that he was a girl, but she wasn't buying it, commenting on his "flat chest" and "boyish mannerisms". Jessie did his best to still keep up appearances that he was in fact a Shinra employee, but had to confess that was in fact not a girl and was a boy in women's clothes. Scarlet pressed him on the matter, curious to understand his motivations to pass off as female. "I don't know...I thought I looked good as a girl," Jessie replied with a sheepish smile and a nervous laugh. Scarlet wasn't one to entertain anyone she felt was beneath them unless they entertained her and to Jessie's credit she was amused by him. Both in his appearance and how well he resembled a girl and his brazenness to try to sneak his way all the way up to the executive offices. Scarlet was also drawn to an aura Jessie was giving off. One of a demure, sweet, and submissive boy. Someone she could have fun subduing and tormenting. Playing along with his story, Scarlet offered to let Jessie work with her directly as "an assistant on a project she was working on". Taken aback by her question, Jessie wasn't sure how to respond except to ask her, "You want me, to work for you?" Jessie couldn't deny that Scarlet had a presence that captured his attention and his senses. She was strong, confident, and direct. She appealed to side of him he didn't want to admit he had, but was all to clear after spending time in Don Corneo's dungeon bound and gagged like helpless damsel in distress. The thought of working for such an attractive and dominant woman was too appealing to him, distracting him from his initial objective. However, the thought that being able to work directly with Scarlet would offer him opportunities to gather information and possibly sabotage Shinra from within was too promising a prospect to pass up. Being completely amateur at espionage, Jessie failed to realize that this was all coming too easy and he was likely being led into a trap, nullifying any advantage he could gain accepting her offer. It didn't help that Scarlet was a busy woman and her time was precious, prompting her to insist Jessie answer her immediately. Jessie could only respond with a "Yes", thus sealing his fate in the coming hours. Scarlet with Jessie in tow made for her office. Once they arrived, Scarlet ordered all her personnel to leave and locking the door so no one could disturb them, leaving just her and Jessie alone. "Strip," she ordered Jessie as she began emptying a personal safe of a collection of suspicious items. Jessie was confused by here request only for Scarlet to order him again, "I said STRIP! Bra, panties, and shoes only! Chop chop, boy!" Jessie startled by Scarlet's raised voice and forceful tone did as he was ordered. He felt silly taking off his clothes, which he grew to feel comfortable in, to only just the bustier top and panties he wore underneath. He had to remove his shoes to remove his stockings, but put them back on as soon as they were off. He left his clothes on the floor and held himself feeling a bit drafty in his underwear. He noticed Scarlett had placed bundles of rope and a rubber ball with leather straps attached onto a nearby table. Catching him in undress out of the corner of her eye, Scarlet then instructed Jessie to bring a chair over and place it facing the door and to stand next to facing the door as well. Jessie did as was instructed and stood still as he heard Scarlet fiddle with something behind him. He heard something flop to the ground behind him prompting him to turn his head look down on the floor. "Eyes forward, boy." Scarlet ordered him when she noticed him peeking. Jessie nervously turned his gaze back to the door, but not before seeing uncoiled lengths of rope on the floor. "Arms behind your back," the executive ordered her subordinate. Jessie reach his hands back behind him only for them to be grabbed and something wrapping around his wrists and keeping them secured together. The same was done to his elbows forcing them to touch together behind his back. Jessie quietly yelped under his breath at the feeling of his arms behind tied behind his back, bringing his mind back to when he was Corneo's captive earlier. While the restraints weren't as strict as the metal cuffs that bound his wrists and ankles before, the rope that bound his arms and now his legs were greater in number and firmer in holding him secured. Once his arms and legs were bound, Scarlet made Jessie turn around with her hands on his shoulders, forcing him to have to hop in place to pivot around to face her. The sound of his high heels clacking loudly on the floor with each hop echoed in the room. Jessie looked at her with a concerned gaze, but her gaze was one of amusement and perhaps what he would think an animal that kills for fun would make when gazing upon an unsuspecting prey. Jessie realized that with every fiber of her being, Scarlet was a predator and it was far too late that he realize that he was her prey and he was now at her mercy. Sensing his fear, Scarlet put a hand on his chin and made an attempt to calm the poor femboy, but coming off as more sinister than soothing. "Relax, boy. I'm not going to hurt you. At least not yet anyway. I'm just going to have some fun with you. And yes, this IS part of your job now and I will not accept no for an answer. Now be a good little boy and SIT," Scarlet ordered as she pointed to the chair next to him. Jessie took a few seconds to let his situation set in as well as what she said, but not wanting to anger her further Jessie reluctantly hopped again and sat down in the chair. Scarlet immediately grabbed Jessie's arms and made him drape them over the back to the chair and she began to tie him to the chair and secure him to it. Once she was finished tying him, Jessie could feel just how helpless he was now as he could barely move in the chair. But Scarlet wasn't done. She then grabbed the rubber ball with straps attached to it and leaning from behind Jessie and presented the object to him in front of his face. "Do you know what this is," she asked in a mocking tone, knowing fully well he'd already experienced  a ballgag before knowing Corneo's tastes. Jessie indeed did know what it was and gulped at the sight of it, knowing that it was most certainly going to go into his mouth and silence him. He tried to play as if he didn't by responding with a "nnm mmm" and shaking his head. "I find that unlikely. You strike me as the kind of boy whose had one of these in his mouth before and knows exactly what it is and what it's for. Now stop stalling and open your mouth, boy." Jessie at first refused, knowing that once he was gagged he would truly be helpless and unable to call for help, assuming anyone would be able to hear him nor would even care. Not wanting to waste time, Scarlet then grabbed his ponytail and yanked backwards hard. Jessie let out a cry of pain from his hair being sharply pulled. This gave Scarlet the opening to slip the ballgag into his mouth and push it in. Jessie let out a pained whine that was muffled by the gag upon being forced to receive it against his will. It was an experience unlike when a similar gag was forcing into his mouth in Corneo's dungeon. Once the gag was strapped in place nice and tight, Scarlet took a minute to admire her pretty captive. Jessie wriggled in his bondage and whimpered into his gag as the tall blonde observed her handiwork. "Good. Just as I like them. Weak and helpless." Jessie whimpered some and again attempted to struggle in his bondage but with no success. Scarlet then stepped away from Jessie's gaze behind him and proceeded to remove her dress revealing her bra, panties, and a corset underneath. She then grabbed another item from her safe and attached to herself. Jessie then saw a pink glowing object come into his gaze from the side at eye level. He noticed it was long and thick and strapped to Scarlet's pelvic region. Based on it's shape it was clear to Jessie what it was and he found himself puckering up at the thought of Scarlet using it on him. "Now that I've shown you the ropes, boy, let's see how you take DIC-tation," Scarlet said with taunting and playful tone. All Jessie could do was endure Scarlet's torments for the following hours until he passed out from exhaustion.

Thanks so much for the amazing artwork, Guilherme! So happy with how it came out! ^_^

Jessie © Me ^_^

Scarlet and Final Fantasy 7 © SquareEnix

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