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Chapter 24
by Mr Nice Guy
What's next?
Hooked on a Riley
Day One
Tyler was just killing time. A few minutes between meetings, doomscrolling through the usual trash: recycled memes, gym bros flexing in locker rooms, some girl selling crystals.
Then he saw her.
It was just a glimpse at first—pastel filter, soft lighting, glossy lips. He had scrolled passed her before he realized what he had done. He paused. Scrolled back.
There was something about her. She was pretty. No, maybe more than pretty. Beautiful? Yeah, that made sense. This girl was beautiful. She seemed so natural, so confident. Who was she?
@GirleyRiley
Her latest post was a mirror selfie. Tight strawberry-coloured crop top. Shimmery skin. A little kissy face into the phone. One hand up to fluff her hair. It was a pose he'd seen a thousand times online, young girls trying to get attention, showing off what they had, hoping to build an audience. But something about this one, this GirleyRiley, felt different. He found himself interested.
The caption was short: “Felt cute - might delete later. IDK”
Tyler didn't usually linger on influencer stuff. But she was different. Something about the way she tilted her hips. Her expression—playful, a little inviting, like she wanted him to look.
Tyler didn't know why he tapped it. He didn't even mean to tap it, really. But there he was, scrolling through her profile before he realized what he was doing.
Ten minutes passed. Then twenty. He was deep in the scroll, bouncing between reels, old posts, stories. The earliest ones felt more awkward—still hot, but less confident. Her evolution was addictive. She was getting better at it. Every post more polished. More alluring.
He followed her. Liked three posts in a row.
Then closed the app.
Day Two
He thought about her during lunch. Just popped into his mind without warning. That little half-smile she gave the camera in one of her videos. There was something so interesting about her, something he couldn't quite put his finger on.
He opened Instagram.
A new post. This time she was holding a lip gloss applicator, talking into the camera with soft focus and breathy narration: "Okay, I found the cutest shade and it tastes like cherries, you guys."
Tyler's pulse jumped. He could feel it, something he logically knew wasn't real, but he felt it nonetheless. You guys. It was like she was speaking directly to him!
He saved the reel.
He didn't even wear lip gloss. But he remembered the brand. Just in case. Tyler wanted to know what made Riley tick, and if lip gloss that tasted like cherries was the thing, then he would pay attention.
He left a comment:
"You're unreal"
She hearted it.
Day Three
She posted a reel that morning in a tight pastel workout outfit. The caption said: "Which pose is your fave?" followed by a poll.
Tyler watched it five times.
He voted.
He stared at the poll numbers like they mattered.
In the afternoon, he checked again—no new stories. Disappointed, he scrolled through her older stuff. Found a shot from two weeks ago, where she's in a bubble bath with her toes pointed at the camera. How on Earth had he missed that one?
Of course he saved it.
He shared a post with his friend, Dan.
"Yo. She's fire. Not even sure what it is exactly, but like… I can't stop watching her stuff."
Dan sent back a thumbs-up and an emoji of a pair of eyeballs.
Tyler felt oddly proud.
Day Four
Sexy.
Yes, Tyler had woken up realizing the word he hadn't been able to say before. GirleyRiley was sexy. And beautiful. It was like they were two different things. He could stare at her all day, and sometimes he worried that he'd end up doing that, and admire her beauty. But then there was this other quality, this sexiness that she brought to every post, every wink, every movement. She was concentrated sexiness. She should come with a warning label.
He stared at the selfie she'd taken that morning. She was sitting at a breakfast nook, a bowl of what looked like yogurt beside her, and a banana, dipped in yogurt, about to enter her red painted lips.
Tyler hardly noticed that she was wearing a bikini.
Who was this girl?!
He wanted to know her. Know everything about her. He checked her profile. No opportunity to become a patron for additional content, no chance to connect on a deeper level.
He'd seen it before, though. They build a following, then they pounce. He didn't mind. GirleyRiley was different. She was sexy, interesting, and he wanted to know about her. There was nothing predatory about the way she was conducting her business. When the opportunity arose, Tyler would gladly contribute.
He went back to the photo. Liked it, then shared it with all his friends.
Day Five
Nothing.
No post. No reel. No story. No update.
Weird.
He checked again later. Still nothing.
He scrolled back through older content—stuff he'd already seen. Her in those denim shorts, sipping a milkshake. Her on a bed, feet in the air, giggling at something off-camera. There was a silly one where she tried doing a "sexy" dance and ended up laughing halfway through.
He liked that one more than he expected.
He clicked through every single story highlight. Then he did it again.
It wasn't just that she was hot—he realized that now. She made him feel something. Cozy. Turned on. Curious. Like she was letting him see a private world, and only he appreciated it properly.
He refreshed the feed.
Still nothing.
His chest tightened. He needed more.
Day Six
Still no post.
He felt off. Like he was waiting for something and couldn't name it.
His feed felt emptier. The algorithm was trying to tempt him with other creators, but they just didn't click. They were too polished or too fake. No warmth. No Riley.
At work, he kept checking. Not just Insta. TikTok. Threads. Pinterest, even.
Nothing.
It didn't mean her account was dead, at least on the audience side. Despite lack of new content, GirleyRiley's followers had doubled from the day before, which had been double from the day before that. It only made sense. Tyler was pretty sure the internet had never been host to a girl as sexy as Riley was.
He went through her posts, making sure he had liked every one, making sure he had commented how beautiful she looked.
By evening, he was staring at her profile picture, wondering where she'd gone. Was she okay?
He watched an old reel again, one with her licking a popsicle and giggling. His breath hitched.
He wanted to DM her, but he didn't want to be weird.
Instead, he made a burner and sent:
"I really miss your posts. They always brighten my day."
He didn't get a reply.
Still, it felt better to say it.
Day Seven
He had dreams about her again.
This time she was in his apartment, sitting on his lap. Just looking at him. Not even touching. But smiling like she knew everything he was thinking. His alarm woke him before he could say a word.
The craving was worse now.
He saved three more old posts. He made a folder just for her.
Every time he saw her face, he got that same weird tingle. Like relief. Like being seen.
He wanted her back.
He needed her back.
Day Eight
She posted.
Finally.
It was a reel—soft music, a slow turn toward the camera.
Her lips.
They were fuller. Plumper. So glossy they looked wet. Her face looked a little different—same Riley, but elevated. Like someone upgraded her in a quiet, perfect way.
She smiled.
A slow, sultry smile that crept across her face like she knew he’d been waiting.
Caption:
"New lips, new me *kiss* thanks for being patient, babes - more soon"
Tyler watched it seven times in a row. The sound off. Then the sound on. Then in slow motion.
He stared at her lips. His throat was dry.
He commented with trembling fingers:
"Worth the wait. You're perfect."
She hearted it.
He melted.
What's next?
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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 17, 2025
by ShimoDragon
Created on Feb 1, 2018
by Dayeandknight
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