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Chapter 22
by ShimoDragon
What's next?
Kiss Crazy
Riley was in the middle of yet another meditation session in the bathroom. In one hand he held his vibrating egg against his groin and in the other was his phone displaying a shirtless selfie of Chase from his social media. He tried to keep his mind on something normal like Chase's chiseled jaw or his glistening muscles, but no matter what his eyes kept going back to those lips. He wanted to feel them on his own lips, he wanted to taste them. But in the back of his mind was a nagging thought that maybe there was something wrong with that?
No, that's ridiculous! Isabelle would've told him that he was being weird when he first brought it up if that were the case. She was always looking out for him so if she talked like it was normal then that meant it had to be perfectly normal! Besides, it wasn't like he wanted to kiss Chase as his partner. He just wanted to kiss him like a girlfriend kisses their boyfriend! Not like the romantic crap couples do, no this was clearly different.
Having shook the doubt out of his mind, Riley refocused on the picture in front of him. He shifted the egg slightly to hit just the right spot. He was feeling ecstatic as his mind wandered back to Chase's lips. His breast forms heaved and his juicy thighs jiggled as he thought about what he wanted to do with those lips. With the mental image of himself and the football captain locking lips clear in his mind, Riley finished all over his hand. With meditation complete Riley felt incredibly focused, and he knew exactly what he should do next.
Riley cleaned himself up, slid his panties back on, and marched out of the bathroom straight to Isabelle who was fiddling at her computer. "Isa I can't stop thinking about it, can we pretty please practice kissing? I need to make sure I know what I'm doing when I do it with Chase!"
Isabelle had to stop herself from smirking at Riley's cute begging. She quickly composed herself and gave Riley an exasperated sigh. "If you really are that eager then I suppose I could help you practice a little. No amount of practice is going to fix the underlying issue though. Your lips are simply boring, princess, they're nowhere near full enough!"
"I know but I need this, Isa. Please, please, please!!!" Riley fell to his knees so quickly as he begged that his skirt flipped up and showed off his pretty pink panties to Isabelle.
"I already said yes, girl. Let's just get this over with." Isabelle puckered her lips and leaned towards Riley.
Riley hesitated for a moment, unsure of how he should start. After a brief moment of stillness he decided not to think too hard and just went for it. Isabelle hadn't been lying when she called his technique sloppy. Riley basically mashed his own lips in hers without any tact, it was frankly embarrassing. But try as he might, Riley couldn't get into it. Kissing Isabelle felt... weird. It felt wrong, it borderline felt gross. Isabelle was his ex, she wasn't someone he could imagine kissing, not since they had broken up.
Riley closed his eyes and tried to imagine Isabelle was someone else. One of the girls from the gym. There was a redhead that would do yoga near the windows that he could picture in his head. He imagined he was practicing kissing with her instead and... it still felt weird. He cycled through a bunch of different women in his mind, some from the gym and some famous. Every single one elicited the same response. The idea of kissing a woman just reminded him of his ex...
Isabelle's face and lips felt far too womanly for him to effectively imagine it but he decided to try and picture Chase instead. The difference was both instant and staggering. The thought of kissing Chase was just so... right! He kissed again, gentler this time and with far more passion than before. It felt amazing. He reached up to caress the side of Chase's face, to feel that powerful jawline he adored. But what he felt was the long silky hair of a woman.
Riley opened his eyes again to see Isabelle, looking thoroughly disinterested, and it was enough to nearly make him gag. The kiss broke.
"Well I suppose you finished a bit better than you started, but that was still pretty sad." Isabelle shook her head as she wiped some of Riley's lip gloss off of her face.
Riley touched his lips with a painted finger. He could've sworn he had been kissing Chase for a moment there, but it was just an illusion made from his own desires. "Y-you're right. I don't care what it takes, Isa, I need bigger lips as soon as possible!"
"Really? You seemed a little **** when I initially brought it up."
"I decided that practicing isn't going to work as well as I had hoped... It feels too wrong to kiss you, I don't like it." Riley looked down, worried he would offend Isabelle.
"That makes sense, princess." She patted Riley's head reassuringly. "While you definitely aren't ready yet, your lips were clearly made for someone like Chase. It only makes sense that a good girl like you would get excited from the thought of kissing your soon-to-be boyfriend. It's perfectly normal."
Riley breathed a sigh of relief. "I thought you might be angry at me... But you're, like, totally right. I need bigger lips so I can start kissing Chase for real!"
"You can count on me for that Riley-girl, I'll find you the best option out there!"
With that Riley left to read a new edition of his favorite makeup blog. Once he had left Isabelle turned back to her computer to look at the lip filler options she had been googling. They were pricier than she had expected and Riley's savings were starting to dry out. At this rate they wouldn't be able to afford some of the bigger things she had planned without her chipping in her own cash and that wasn't happening.
Riley was going to have to get a job. Luckily, Isabelle had already considered this and had come up with a plan just in case. She got to work putting together a new subliminal message, though this one was not for Riley.
You think this post is interesting. GirleyRiley is interesting. You think she is beautiful and sexy. You want to like her post and comment about how beautiful she looks. You want to follow her so that you can see her in more posts. GirleyRiley is very interesting. She is very sexy. You want to show just how interesting and sexy she is to all of your friends. You want more people to know about GirleyRiley.
This message would be woven into the background of all of Riley's social media posts from now on. With any luck it his account would explode in popularity. Admittedly this would be a test of Isabelle's skills as a hypnotist but she was certain that so long as she paired the message with the correct kind of content, Riley would become a star.
Who needs a real job with troublesome background checks when you've got the internet?
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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 19, 2025
by ShimoDragon
Created on Feb 1, 2018
by Dayeandknight
- 4,648 Likes
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