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Chapter 19
by ShimoDragon
What's next?
Advanced Meditation
After about an hour of modeling outfits and snapping photos Riley finally sat down, instinctually crossing his legs at the knee, and took a look at the pictures Isabelle had taken of him. There was the cropped cardigan and silky shorts that started it all, the outfit made him almost glow in the light filtering through the bedroom window. Isabelle had called him "angelic" as he posed for that one.
Next was a braless tube top with a pair of jean booty shorts that Isabelle told him was "probably the sexiest thing you've ever worn". After that was a deep v-neck blouse with skin tight leggings which Riley loved the feel of. He even remembered Isabelle's tip to always wear a thong with tight pants, he wouldn't be caught dead with panty lines.
The final two outfits were something special as they were the first times he'd ever actually worn a skirt before! The flowing and flowery summer dress he tried on next felt more freeing than anything he had worn in his life. He had no idea that baggy clothes could also look this cute when designed right. Simply putting on that dress had completely changed his outlook on fashion!
The last outfit was the one that the two of them decided would be Riley's perfect profile pic. A simple combination of a pink spaghetti string top, which easily showed off the edges of his lacy black bra, and a short black skirt. In the photo Riley was posed with a pout and a peace sign showing off both his glossy lips and glossy nails. A perfect mix that showed off both playfulness and empathy to the female struggle. The ladies were sure to love it.
Riley stood up again and stretched. The fluttering of the skirt on his hairless thighs was fresh and invigorating experience. Every time the delicate fabric danced across his skin it reminded him of the new and improved man that he had become. To think that he had never worn a skirt until now was a genuine travesty, what had been stopping him before?
"You were right as usual, Isa." Riley did a twirl to show off his outfit one last time. "That little photoshoot was great. Trying on cute clothes and taking pictures is way more fun than I thought it would be!"
"Another need that you didn't know you had." Isabelle nodded thoughtfully. "This is exactly why you need a boyfriend Riley, you'd never be able to understand male needs on your own if I had to help you realize how much you love wearing skirts or taking selfies."
"Gosh, you're so right Isa. I need to get a boyfriend ASAP." Riley shook his head at his own lack of self-awareness.
"Luckily for you a new social media account will definitely help with that." Isabelle smiled as she took Riley's phone and started filling out the information for a handful of new accounts across different platforms. She made sure to discretely set the gender to female for any that required it whenever Riley wasn't paying attention. All of the accounts shared the same name: GirleyRiley. "A good name is the first step to building your personal brand. GirleyRiley lets everyone know that you're here for the girls, plus it's catchy too!"
With the accounts made Isabelle had Riley make his first post. It was a collection of the photos they had taken earlier with the caption: Just cleared out my closet of any gross old clothes in celebration of the new account! Decided to take cute pics in some of the outfits that survived the purge! #photoshoot #modeling #fashion #beautiful #cute
"That'll be a good start, we can have you post some more pics everyday to really fill up your catalogue." Isabelle giggled a bit as she noticed the excitement on Riley's face. He was just as excited to take those photos as she was. "We just have one more thing to take care of today in regards to you becoming Chase's girlfriend."
"Another? But I thought we'd be done with the new accounts?" Riley tilted his head in confusion causing his silky long hair to slide along his shoulders.
"Don't worry, this last step is simple. All we're going to do is find Chase's account and follow it." Isabelle opened the search bar and quickly found the account of Chase Donovan, captain of the Goldridge Eagles. She hit the follow button and scrolled down to find Chase's most recent pictures. The very first one was a thirst trap, exactly what she was looking for. "You haven't meditated today yet, have you princess?"
"No, not yet. Why do you ask?"
"Well Riley-girl, if you are aiming to be Chase's girlfriend then you should really start focusing your meditations on him. Your goal isn't just any kind of man anymore, it's the most popular man at Goldridge College."
Riley nodded with a look of understanding as she spoke, "Yeah... that makes sense. I can't settle for just any good looking guy can I?"
Isabell leaned in to whisper encouragements into Riley's ear while she handed his phone back to him. "From now on every time you meditate you should be looking at pictures of Chase Donovan, thinking about his handsome face and strong muscles. Here, this is the perfect picture for you to start with."
Riley looked down at the post which showed Chase dripping with sweat lifting up his shirt to wipe his face and showing off his rippling abs alongside a fairly blatant bulge. Riley could already feel himself heating up just looking at it.
"But not so fast!" Isabelle stopped Riley from turning around and running straight into the bathroom. "Before you go I actually have a present for you." She reached into one of her drawers and pulled out a little pink ovular orb attached to a remote by a thin wire. "This little thing is called an egg. It's a tool to help perfect your meditation. I read online that it increases the effects exponentially so this should really help you focus in on becoming Chase's girlfriend!"
Riley eyed the device with a slight doubt but Isabelle hadn't led him astray yet, so he took it with a curt, "Thanks," and ran into the bathroom for a little privacy.
Soon after the water turned on she could still hear some of Riley's noises of pleasure, much louder than any meditation session before. She couldn't help but laugh to herself. Not only did Riley look damn near indistinguishable from a woman, he was even masturbating like a woman now! Not like he even could masturbate like a man anymore with how much his dick had shrank over the weeks and months of estrogen.
Even she was shocked at just how well her plan had been going so far, and yet there was still lots of work to be done in order to change Riley into her perfect little bimbo.
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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
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