Chapter 21
by Mr Nice Guy
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Kiss Curious
The gym always smelled like sweat and steel and something sweet Riley could never quite place, a cold smell that reminded him of electricity. It didn't matter. Riley didn't come to the gym for the smells. It was the sights that he cared about.
Riley was on the hip thrust machine, half-listening to a beauty podcast about skincare innovations. Isabelle had told him that he needed to make sure that his ass was an _ass_et, so he always made sure to focus on it when he was working out. Sure, he worked on the other parts of his body, but for him, every day was booty day.
And then Riley saw him. Chase. It was as if the star quarterback had some kind of gravitational pull. As soon as the big man walked into the gym, Riley's eyes would find him—muscles tight under a moisture-wicking tank, confident look on his face as he moved to an empty machine, shorts loose, but not so baggy that they didn't give something for Riley to look at. He was lifting today. Heavy. His arms flexed with each rep, veins standing out like cables under bronze skin.
And Riley watched. No, he didn't watch. He drank Chase in.
His gaze flicked down, of course—he always looked there, even when he told himself not to. The thick outline pressing against Chase's gym shorts was obscene in the best way, bold and heavy. Riley couldn’t stop staring. Was it always this big? This... detailed? He could trace the shape with his eyes—thick shaft, heavy tip, the faintest sway as Chase moved. What would it feel like against his cheek? His lips? He swallowed hard, startled by how vivid the thought was. Would it be warm? Would it throb? Would it taste like sweat and salt, or would it have its own unique flavour palette? He tore his eyes away, face flushed, thighs pressed tight together as heat rolled through him like static. These were all questions he meditated on daily, but it was special when he was actually seeing it.
But today… today was different. Today, for a while at least, Riley was able to lift his eyes again. Slowly. Along Chase's torso, up his neck, over his sharp jaw—and landed on his lips.
They were plush. Slightly parted with effort, a little glossy with sweat. They looked soft. Strong. Like they could kiss and bite all at once.
Kiss.
The word dropped into Riley's head like a stone in water. A ripple followed. Kissing is a way of being close. You want to learn Chase's needs.
He shook his head, trying to focus on his reps. But it didn't help. The thought swirled now, stubborn. Not just the lips. The act. What would Chase's mouth feel like against his? What did he taste like? Would he be gentle? Would he hold Riley's waist, or maybe the back of his neck?
It felt ridiculous to think about. But also… not ridiculous. Not at all. Wouldn't kissing Chase just be a conduit to understanding the big man's needs? And that was, after all, one of his goals. Besides, Riley wasn't sure where he'd heard it, but kissing was just something girlfriends do for their boyfriends. And if he had his way, soon he and Chase would be exactly that. His chest fluttered with nervous warmth.
When he finally climbed off the machine, Riley wiped his brow, adjusted the band of his leggings, made sure his breast forms were on full display, and headed toward the weight section.
Straight toward his target.
"Hey," he said, breathier than he meant to be, but satisfied at how it sounded.
Chase looked up mid-set and grinned. "Hey, Riley-girl. Looking good today."
Riley flushed. "Thanks. You're, like, wow. I mean, seriously. How much is that?"
Chase sat up, flexing casually. "This? Nothing too big. Just warming up."
Riley giggled and tilted his head. "You're always so strong. I was watching you do that angled barbell thingy the other day. What's the difference between that and like… a regular curl?"
He knew the difference. Of course he did. But still, he leaned forward just a bit, arms clasped in front of him, hanging on Chase's every word.
Chase beamed. "Okay, so the angle hits your brachialis more. It's a deeper cut under the bicep. Here—feel."
Chase extended his arm, flexed it. Riley reached out, fingers brushing muscle, and nodded seriously. "Wow… yeah. That's… incredible. You're smart and strong!"
Chase laughed softly, eyes lingering a bit too long. "You're cute."
That one little word lingered in Riley's ears all the way home.
They were back in the apartment, post-shower, when Riley sat cross-legged on the bed in one of his oversized crop tees, panties, and thigh-high socks. Isabelle was scrolling through her phone nearby.
He fiddled with the edge of his sock for a minute before speaking.
"Do you think..." He trailed off. "Do you think it would be a good idea if I... learned how to kiss?"
Isabelle raised an eyebrow, not looking up. "Learned?"
"Yeah, like… practiced. I think I might be bad at it. I just keep thinking about it, and… I don't know. It seems kind of important."
She set her phone down slowly and turned toward him, smiling with that practiced blend of affection and control.
"Oh, sweetie-girl. You've been thinking about that football player again, huh?"
He nodded.
"I get it. He is amazing, but honestly, you're not ready for someone like him," she said gently.
Riley's face fell. "Why not?"
"Well..." Isabelle leaned forward, brushing his hair back from his forehead. "You remember when we dated? You weren't... great at it. Not just your technique—though, let's be honest, that was a little sloppy—but your lips are kind of boring."
Riley blinked. "My lips?" He thought about all the effort he'd taken to paint them beautifully that morning, touching them up whenever he needed to. Had it all been for nothing?
"It's just that they're flat. Thin. Just... plain. And women—and guys like Chase too—aren't into men with boring faces. Look at any teen magazine. You think it's a coincidence every boy they swoon over has full, kissable lips?" She tilted her head. "The bigger the better."
He stared down at his hands, fidgeting.
"But," she added, brushing her fingers under his chin, lifting his face again, "if you want to be more kissable, I could look into some solutions for you. I've actually been meaning to talk to you about it. We could explore some options. Just enhancements, at first. You don’t have to decide right now."
Riley bit his bottom lip—not full enough—and nodded. "Okay. Yeah. If you think it'll help. I just want to... I want to be ready. You know. For when he wants to kiss me."
Isabelle kissed his forehead. "That's my good girl."
He didn't even flinch at the word. Why would he? He was a good girl. Isabelle had told him so.
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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
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- 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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