Disable your Ad Blocker! Thanks :)
Chapter 48 by ShimoDragon
What's next?
A Girlfriend's Responsibility
Isabelle watched as Riley poured himself a glass of water, still squeezed into the nurse costume with the zipper halfway down. He had told her that he had spent his stream roleplaying as a caregiver for his audience and that had started to form an idea in her head.
"You know, Riley, maybe you should start thinking about this caregiver angle a little more literally." She paused to take a sip of her tea. "Don't get me wrong, you're learning some great stuff during your streams but you have yet to consider Chase's most basic and universal needs."
Riley's ears perked up at this and he turned to rush over to Isabelle, almost causing his boobs to pop out of the slutty dress. "What needs?! If I'm missing something you have to tell me Isa!"
Isabelle kept her tone cool even though she was immensely pleased by how eager Riley was. "If you're going to take care of his needs, be his caregiver, then shouldn't you learn how to cook and clean? Food is the most basic need there is."
"Of course!" Riley lightly slapped his forehead. "People eat everyday! If I can start to help him with that then that would make me an even better girlfriend! Besides, the ladies will love a man that can coo-"
"Riley!" Isabelle interrupted him. "We've talked about this, you can't be calling yourself a man anymore!"
Riley raised a perfectly manicured hand to his perfectly glossy lips. "Oh shoot! That was an accident Isa, I swear I didn't mean to."
"It doesn't matter if you don't mean to, sweetie. Do you know what people are going to think if they hear you call yourself a man while Chase Donovan is your boyfriend?" She waited long enough to let the question hang in the air but continued before Riley could respond. "They're going to think that you don't respect him, that you think he's some kind of joke. And if his girlfriend doesn't respect him then why would anyone else? He'd become a laughing stock!"
"WHAT?! No, I respect Chase! I wouldn't want anyone to treat him like that!"
"Then you have to commit to this change, princess. It's your responsibility as Chase's girlfriend. From now on you are not a man, or a boy, or a guy, or even a dude! If you slip up again it could cause serious damage to your relationship with Chase!"
"I won't slip up again! I promise!" Riley's brow furrowed a bit after making his serious statement. "But... what should I call myself?"
"I would've thought that part would be obvious." Isabelle shook her head like she was explaining basic addition. "You're a girlfriend Riley, so you should call yourself a girl for short!"
A look of understanding washed over Riley's face. "That makes sooooo much sense! I can't believe I didn't realize it sooner, what would I do without you Isa?"
"You know I'm here to help, princess. Now, how about you go do a little bit of dusting while I find some recipes for you to practice?" She typed a quick search into her computer. "I've already got a good starting point here: 5 Easy Recipes to Impress Your Man With. Sounds perfect for you!"
"That sounds great Isa, thank you so much! Once I know how to cook, a girl like me will be totally irresistible! I'll go get ready!" Riley hurried off with his ass threatening to bounce out of his dress' tiny skirt with each step.
Isabelle smiled as he left. Another important step taken in Riley's transformation. It was still a long way off but eventually she'd get Riley to the point where he'd forget he was ever a man in the first place.
What's next?
Disable your Ad Blocker! Thanks :)
Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
- 5,860 Likes
- 2,189,724 Views
- 932 Favorites
- 621 Bookmarks
- 384 Chapters
- 73 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments