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Chapter 44
by
Mr Nice Guy
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I’ve Been Practicing
The sun warmed Riley’s skin as he stretched across the beach blanket, his long legs angled just so, toes wiggling slightly as they peeked out from his strappy sandals. His microkini felt snug and confident, tied tight against his new curves. He was still a little giddy—no, electric—just from watching Chase watch him.
The day was perfect. Warm sand, soft breeze, the gentle murmur of waves. And Chase, sitting beside him, drinking him in with those big arms folded across his chest and his shirt left half-open like some kind of movie star on vacation.
Riley loved everything about it. Not only was he able to have a lovely beach day with the man who he hoped to make his boyfriend, but he was getting to learn more and more about Chase’s needs. Like touch, for example. Who would have guessed that Chase didn’t just want to be touched by Riley, but he seemed to have the need to touch Riley back. When he’d helped Riley out with his sunscreen, it had been obvious that the big man was getting as much out of the gesture as Riley was.
Riley made note of this, and planned on capitalizing on it in the near future.
Fans had started showing up not long after they'd settled in. A pair of girls in sun hats squealed when they recognized him, asking for selfies and hugs. Then came a tanned boy with heart-shaped sunglasses and a bashful smile. He asked for an autograph. Riley signed his towel with a flourish, then leaned in and gave the boy a big kiss on the cheek. His gloss left a little red mark.
The boy looked dazed as he stumbled away, giggling.
Riley blushed and pulled out his compact mirror from his tote. With practiced ease, he retouched his lips—another layer of cherry-pink gloss—and gently powdered his cheeks. Chase was watching, of course. Riley smiled into the mirror. Good. Let him watch.
"You really like that kind of attention?" Chase asked, shading his eyes with his hand. His voice was half-curious, half-something-else.
Riley shrugged, snapping the compact shut. "It’s nice. Pays the bills. Makes me feel connected. But I only care what one person thinks, really."
That made Chase blink.
He leaned in. “Hey... can I ask something? Why’d you get the surgery? I mean—” He waved vaguely toward Riley’s face. “Wasn’t that scary?”
Riley’s heart fluttered. “Scary? Not really. Not when you know exactly who you’re doing it for.”
Chase blinked. “Wait… what do you mean?”
"I had someone in mind the whole time," Riley said softly, tracing a finger along the edge of his sunglasses. “Someone I wanted to impress. Someone I wanted to be perfect for. You don’t get scared when you’re goal-oriented, Chase.”
He turned his head slowly, locking eyes with him.
“Do you like it?” Riley asked. “Because if there’s anything you don’t like, I could always... tweak it. I want to be exactly your type. I’d change anything, if it meant making you happy.”
There was a pause—heavy, golden, and trembling.
Then, mercifully, the sharp jingle of a nearby ice cream truck broke the silence.
Riley gasped, clutching Chase’s arm. “Ohmygod, Chase! Ice cream! Can we get some?! Please?”
She was serious.
Chase stared at her, his heart pounding as her words repeated in his head.
"I’d change anything, if it meant making you happy."
What the hell was he supposed to do with that? This wasn’t just flirtation. This was full-on devotion. She—GirleyRiley, the most-watched girl on the internet, the literal fantasy of half the male population—was offering herself up to him like some kind of wish-granting goddess.
And she was still so cheerful. So sweet. She squeezed his arm and bounced on the balls of her feet, practically glowing.
Chase blinked, trying to get his blood to move somewhere besides his groin. “Yeah. Ice cream sounds good.”
They trudged across the sand together, Riley, already reading the menu posted on the side of the vendor, chatting about how she hadn’t had a coconut popsicle since she was a kid. Her hips swayed, the red triangles of her bikini barely holding their territory. Chase gritted his teeth.
The truck wasn’t crowded. A couple kids were off to the side with dripping cones. He stepped up and ordered a chocolate cone for himself. Riley followed up with a coconut popsicle, her eyes bright.
They walked to a shady dune nearby and sat down on a towel together. Chase licked his cone slowly, trying to keep his eyes focused on anything except—
Riley knelt beside him, unwrapped her popsicle, and took a long, teasing lick up the side.
Then another. Her eyes fluttered half-closed, as if she were savoring something deeper than just the flavor. She swirled her tongue around the tip, then slid it into her mouth, lips tightening with a soft pop as she pulled it out again. Then in. Then out.
Chase froze.
Her pink tongue peeked out again, trailing up the melting shaft. A drop of coconut-white liquid beaded at the tip and she caught it delicately, her lips wrapping around the top like she was trying to keep it from dripping.
But it dripped anyway.
A glossy streak of white rolled over her bottom lip, down her chin, and landed right between her breasts—just above where her bikini top barely clung.
She giggled, catching the mess with her fingertip and sucking it off with a little murmur of satisfaction.
"Oops," she whispered, licking her lips clean.
Chase’s hand clenched around his cone. And that’s when the tenting in his swim trunks started. There was no stopping it. Not with her sucking and slurping so innocently on that thing like it was—
Riley’s eyes dropped to his lap.
She blinked. Then smiled—slow and knowing—and leaned closer.
“Hey…” she whispered. “Um... d’you want to take care of that?” She nodded toward the public changing rooms just a few yards away, her fingers brushing his forearm. “I could help. If you want.”
Chase’s mouth went dry.
Then Riley added, barely above a whisper, “I’ve been practicing.”
He stood up on autopilot. Riley followed, her popsicle still in hand, swinging gently at her side as they made their way toward the shaded changing stalls.
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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
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
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