Disable your Ad Blocker! Thanks :)
Chapter 17
by ShimoDragon
What's next?
Boyfriends and Girlfriends
Riley had a bright and cheery smile as he practically skipped over to Isabelle, who was lounging at her usual spot on the mats. "Oh my god, Isa! You were totally right! It all worked perfectly!"
Isabelle jumped a little as she looked up from her phone. She had been distracted by some research she was doing on how to further feminize Riley so he had surprised her. "R-Riley! What are you doing back so soon?"
"I did everything you told me to Isa and it worked even better than I imagined! I was a little nervous at first but Chase seems like a really friendly guy. I even gave him my number and he said he'd text me later!"
"That's amazing princess!" Isabelle once again used her nickname for him as she pulled him in for a hug. "Tell me all about this Chase. What's he like?"
"Well at first I picked him because he was easily the biggest guy in the whole gym. I figured a big guy like him would have big needs, and that understanding bigger needs would make me seem even sexier. But as we talked he was actually really nice."
"A big guy, huh? Knowing you, you probably checked out how big he was down there too, didn't you?" She pointed downwards to emphasize her meaning.
Riley brought his hand up to his glossy lips and giggled, "You caught me~ I didn't get a super clear look but he definitely had a lot going on in his shorts! Anyways, I pretended to not know how to use the leg press machine so he could show me how and he was loving it like you said he would. After that I complimented him on how strong and muscular he was and he actually complimented me back! He said that I looked great!"
"It's like I told you babygirl, you're sweet like honey. Since you've been following my tips everyone is noticing the new you, and they all like what they see." Isabelle smiled as she reinforced Riley's pride in his new appearance.
"I should know by now that you're never wrong Isa, but I can hardly believe the world of difference all of you help has made." Riley looked down at his smooth, shapely legs and stacked chest with a soft sigh. "Oh! I almost forgot the best part! Chase goes to the same college that I'm attending next semester, he's actually the captain of the Goldridge Eagles! With us going to the same school I'll have even more chances to see him and understand his needs. I know he's the first guy I've talked to today but I really think he's a good pick... What do you think? Does Chase sound right for me?"
Isabelle's eyes went wide with excitement. "Right? Princess, I think he sounds perfect! Chase is exactly the kind of guy you're looking for. He would make the perfect boyfriend!"
Even in Riley's brainwashed state that word sent off tiny alarm bells in his brain, "B-boyfriend??? What are you talking about Isa? Don't tease me like that!"
"Oh that's right, I forgot that you are so out of the loop with pop culture. You've got such a modern physique now and your fashion is so in style that I forgot you still aren't caught up with the current lingo." She shook her head as though she were explaining the most obvious thing in the world. "Words and their meanings change with the times Riley-girl. Nobody uses the word boyfriend to refer to their partners anymore. A boyfriend is what you've been looking for this whole time! You want to get close to a man so that you can understand his needs and take care of them, in other words a boy who is your close friend!"
Riley's face went blank for only a moment as his brain absorbed this new information before taking it on as gospel, "Oh my god, that was, like, so embarrassing... I totally thought you meant something else." His mind turned back to Chase and he imagined his face while the word boyfriend echoed through his head. It made things a lot easier to have a word to put to his goal now. Chase would make for a great boyfriend.
"Don't worry about it doll, that's what I'm here for. To clue you in on what you don't know and steer you in the right direction. Which leads me to my next lesson!" Isabelle threw up her finger as though she were a professor with a pointer. "You say that Chase is the captain of the football team, yes?"
"That's what he told me, apparently they even call him the star player. You should've seen how burly he looked! I'd be shocked if anyone else on his team even came close." Riley's painted cheeks flushed slightly as he thought back to Chase's sculpted body.
"In that case he'll be even better as your boyfriend than we thought! As one of the most popular guys on campus Chase is bound to know the most popular girls. Once you're actually ready to be in a relationship it would be great for you if someone like Chase were to show you off to these girls. Therefore we have a new goal for you, angel. You want to become Chase's most special friend, someone he wants everyone else to know about. A friend that he introduces to girls. Do you see what I'm getting at?"
Riley's madeup face scrunched into a cute pout as he thought. "I don't get it Isa, just tell me please!"
"Oh don't be silly Riley. Obviously, what you want to do- No, what you need to do is become Chase's girlfriend!" Isabelle had to hide the wickedness from her smile as she watched Riley take in her every word. "It's pretty much every average Joe's dream to be the girlfriend of a popular man, but most of the time they'll only ever pick other popular people. Luckily for you, you're on the fast track to becoming one of the popular ones. Believe me when I tell you that you'll be a girlfriend in no time!"
"Do you really think so? You really think I can be a girlfriend?" Riley asked innocently, with wide eyes framed by beautiful eyelashes and radiant eyeshadow.
"Oh princess, I don't think it. I know it."
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
- Tags
- Hypnosis, Misunderstanding, Crossdress, Halloween, Bet, Dare, Crossdressing, hormones, feminization, sissy, housewife, Stepford, Stepford wife, hucow, Maid, Fetish, Femdom, Thigh-highs, mistaken identity, mind control, manipulation, Accidental, Mr Handy, Vault, Fallout, Magical Crossdressing, Leather, Princess, Secretary, Fantasy, pokemon, Mindcontrol
Updated on Jun 20, 2025
by Mr Nice Guy
Created on Feb 1, 2018
by Dayeandknight
- 4,661 Likes
- 1,586,955 Views
- 846 Favorites
- 511 Bookmarks
- 333 Chapters
- 40 Chapters Deep
- All Comments
- Chapter Comments