Chapter 15
by Mr Nice Guy
What's next?
Sweet Like Honey
The car glided down the road, the late morning sun catching on Riley's freshly painted face as he scrolled idly through his phone, reading makeup tips on fashion sites. Beside him, Isabelle could hardly keep her eyes on the road for how often she glanced over, grinning.
"Riley," she said, almost breathless with pride, "you look so pretty today."
He turned to her, beaming. "You think so? I tried the layering technique I saw in that copper-glow tutorial. And the fox-eye thing with the liner." He paused. "I hope you don't mind," his feminine voice sounding meek, "but I used your stuff. I didn't have any of my own."
Isabelle laughed, delighted. "You nailed it. Your eyes look huge, and that lip gloss—ugh, you could kill a man with that pout. Seriously, angel, you look gorgeous." She reached over and squeezed his soft, smooth knee. "And don't worry about using my makeup. We can go shopping and get you your own, but as long as you look as gorgeous as you do today, I don't mind sharing."
Riley gave a little giggle, high and clear, before biting his bottom lip. "Thanks! It felt really natural today. I can't believe I never tried it before."
Isabelle's heartbeat began to gallop. This was perfect. Not only did he look radiant, but he was loving every second of it. Tank top knotted at his waist, pink gym shorts snug across his thighs, a shimmer to his cheeks and a soft curl to his lashes—her ex-boyfriend Riley looked like a slutty fitness influencer prepping for a soft glam shoot.
"You know what I love most?" Isabelle said, glancing at him again. "How much you trust me. You always take my advice, and look at you now—glowing."
"Of course I trust you," Riley said with a warm shrug. "You've been helping me so much. Like, actually getting results. I feel like I've got a much better chance with women now that you've shown me what I've been screwing up. And I think they're starting to notice."
"Oh, I know they are," Isabelle said with a wink. "That's exactly what I wanted to talk about, girl. You're doing so well, and soon women are going to start wanting to go out with you. But I don't think you're ready for that."
"What do you mean?" Riley asked with a pout.
"Well, you don't want your next relationship to just end up like ours did, do you, baby-doll?" Isabelle asked, leading him to the conclusion she wanted him to make.
She watched as he thought it through, a concentration line appearing between his eyebrows.
"No," he answered her, "I think I screwed that up pretty badly."
"Exactly. Riley-girl, you're not bad, but you've got some bad instincts when it comes to women," Isabelle said, allowing her voice to seem tired, like she was explaining the most obvious thing in the world. "So what happens if you meet a lady who wants to go on a date with you? You'll probably just screw it up again."
"But what should I do? Isabelle, you have to help me!"
"I’ve noticed something at the gym," Isabelle said casually, as if she hadn't heard him. "You’ve been doing great showing off your body—flashing those abs, stretching in those adorable little shorts, making sure to bend over and show off for the ladies. But I've also seen your eyes wandering. Especially to certain... areas of the guys."
Riley blushed faintly but nodded. "I mean... yeah. It's hard not to notice. Have you seen their crotches?! Some of them are really packing!"
Isabelle laughed. "Oh my god, right? I totally get it. Sometimes I swear those sweatpants are just daring you to stare."
He laughed too, the awkward tension melting. "I knew you'd understand."
"Of course. And here's the thing: women love a man who understands men. Not in a 'locker room' way—more like a 'needs' way. Men have needs, and they usually aren't aware of them. You, for instance, weren't aware of your need for makeup for, well, your entire life. It took you this long to figure that out!"
"Oh my God!" Riley squeaked, "You're, like, totally right!"
"Most guys are terrible at communicating what they need. Women are stuck guessing. It's like feeling around in the dark. But a guy who really gets what men need? Even men who aren't him? That's sexy. That's rare."
Riley looked thoughtful. "So… you're saying I should, like, get to know myself?"
"That's never going to work, babygirl," she explained, "You're just not self-aware enough. You've come a long way, but that'll take forever for you to figure out. No, you need help. You need another man in your life, someone who you can understand their needs. That'll be key to you understanding your own."
Riley seemed confused for a moment, mulling over Isabelle's suggestion, but after a few minutes of silence, his eyes lit up.
"I can't believe I never saw it before," he breathed, "There are men all over the place. What a wasted opportunity."
Isabelle nodded, turning down the road to the gym. "Absolutely. You're already great at drawing attention. Just take that same energy—confidence, playfulness—and redirect it. If you catch someone looking, hold the gaze. Give them a little wink, maybe a smile."
He giggled again, instinctively touching the gloss on his lips. "It's so hard making male friends. You think that would actually work?"
"You already are, sweet thing. Just don't overthink it. You're sweet like honey, and trust me—everyone wants a taste."
Riley's stomach fluttered, excitement swirling with nerves. "And then if it works? Like, if a guy wants to get to know me better? Won't I screw that up like I did with us?"
"Not a chance. If you want to get a man to like you, make it about him. Compliment them. Ask them to explain things to you, they love doing that. That's the quickest way to find out his needs, and when you find them, take care of them. Whatever they are."
He beamed, cheeks flushed with the praise. "Okay. I'll try. I mean… it sounds like a bit of effort, but if it works, I guess it'll be worth it."
"That's the spirit," Isabelle said as she pulled into the parking lot. She reached over and squeezed his hand. "You're doing amazing, Riley. Seriously."
As he stepped out of the car and adjusted the waistband of his shorts, Riley felt a fresh rush of confidence. The shimmer on his eyelids caught the sunlight. His lips gleamed like candy. And somewhere deep in his heart, he believed more than ever:
He was a transformed man, modern, available. He couldn't wait for the women at the gym to see the new him. And he couldn't wait for the men to see him either. They won't know what hit them.
What's next?
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
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