This prompt would be central to a character named Max (open to suggestions) who suddenly finds himself in an embarrassing, humiliating, emasculating moment, and people’s reactions to it.

“Come on, get it on” Henry shouted slightly fed up. “Isn’t the dress and cat ears enough?” Max questioned. “I mean, I only came last in fantasy, do I really need to be punished this badly” Max complained. “Maybe, but this is a frat league, so you have to do something that’s even more humiliating than usual” Henry added in creatively. “Do you need my help with it?” Henry asked, smirking and holding the butt plug in his hand. “Do you honestly think I’d let you-“ max finished, pausing as he realized the only other option would be to do it himself. “Yes” Max said weakly, humiliated. He sat down on the bed, bringing the panties down his legs and proceeded to spread his legs out in a rather compromising position. “Nice panties, pink is definitely your colour” Henry joked back staring at him. “Here I go” he said with a shy grin, and with nifty hands he shoved it in. “Oahhh” Max seemed to groan. “Let me help you out one last time” Henry said as he delicately brought the panties up Max’s legs, then prepared the magnetic attachment for the cat tail. “My suffering is only just beginning” max mumbled after thinking about leaving the house like that. Max stood up, letting the skirt of the dress fall back down, and then awkwardly walked down the stairs to the door. His thick wavy mullet almost made him look like a girl, if not for his masculine build and muscles.He wasn’t entirely sure if this was more or less humiliating than the original idea to wear a pink maid costume with his hair tied up in pink bows. He sighed after looking down at himself, and slowly left the house. Today would be a long day. He had to get dinner with his girlfriend today, and he also had to get to his lectures. He’d arrived at the lecture hall after taking a series of side streets to avoid being seen and for the most part it had worked to his benefit. A couple passersby had managed to catch a glance, but nobody was bold enough to say anything directly to him. This class however would be different. He found a comfortable enough chair and awkwardly sat with his legs crossed pulling the dress down as much as possible. It would be even more embarrassing for his classmates to see his panties. A couple of students rolled in, sitting down and a couple specifically came to sit by him. “Nice dress, Max” remarked Tom one of his classmates. “I see you’re dressing up as the frat mascot” said Brayden, a member of one of the other frats. A couple of pictures were taken, and he tried his best to avoid getting caught. This was going to be a long day.

Thank you for reading the prompt. I’m new to dirty story writing so I’m grateful for any feedback that can be provided.

This prompt would be mostly central to Max a frat boy who’s come last in his fraternity’s fantasy football league. As punishment, he’s forced to dress up fully like a femboy maid and has to spend the entire day dressed up. With this prompt I thought it would be fun to deal in max’s emotions and what he goes through.