Disable your Ad Blocker! Thanks :)
Chapter 35
by
Mr Nice Guy
What's next?
The Best Date Ever
Chase had no idea how to dress for a date with someone like her.
He'd changed shirts three times, fixed his hair twice, and stared at himself in the mirror long enough to start doubting everything. Never before had he second guessed himself over whether or not a girl would like him. He was Chase Donovan! Unstoppable Chick Magnet! But now that he was parked outside Riley's house, Chase found himself gripping the steering wheel like it might run away if he let go.
He could do this. He just had to stay cool. Calm. Normal.
Then Riley stepped out the front door and Chase's brain stopped working.
She was radiant.
A micro-skirt in shiny, bubblegum pink barely covered the tops of her thighs. Her top—if it could be called that—was a skin-tight black crop with a heart-shaped cutout that revealed more than it concealed. Platform heels clicked confidently down the walk, and her purse was a glittery clutch with a fluffy pink puff on the zipper. Her lips were glossy, her eyes winged with glittery liner, and her smile...
God.
She looked like a pop star disguised as a pin-up girl disguised as a wet dream.
Chase scrambled out to open the door for her.
"You clean up nice," she said, sliding into the passenger seat. Her perfume hit him instantly—something sweet and dizzying and impossible to ignore.
"You look..." He trailed off. He couldn't find a word big enough. "Wow."
She giggled, reaching across to squeeze his arm. "You're such a sweetie, Chase.”
Dinner was at a trendy downtown spot Riley had picked—somewhere with soft lighting, loud music, and lots of places to be seen. Heads turned the moment they walked in. Chase wasn't used to that kind of attention. But with Riley on his arm, it suddenly made sense.
They hadn't even gotten their drinks when the first girl came over. Then another. Then two more.
"Oh my God, it’s really you!"
"GirleyRiley! Can I get a selfie?!"
"You’re, like, my aesthetic inspo every day."
Riley smiled and posed like it was second nature—blew kisses, twirled her hair, scribbled her signature on napkins with the pink glitter pen from her purse.
Chase just watched, stunned and awestruck.
When the table finally cleared, Riley slid a little closer. "Sorry about all that," she whispered. "Didn't think we'd get swarmed."
Chase shook his head, grinning. "No—it was cool. I mean, you're kind of famous."
"Famous? I don't know about that," she whispered, running her hand lightly up his thigh, "But I do know that you make me feel like a normal girl.”
His breath caught. He cleared his throat.
"So... cheerleading," he said, reaching for the conversation like a lifeline. "You were amazing. Like—really amazing. I’ve never seen anyone move like that. You were just... so confident."
"Oh, I was nervous, but I'd been practicing," she said, leaning in. "And I always perform better when I know people are watching."
Chase swallowed.
They talked for a while longer—about school, classes, football, tryouts—but everything blurred around the edges. All he could focus on was Riley. The way she bit her lip when she laughed. The way her hand kept touching his.
The theater was dark and blessedly quiet. Chase had picked a movie he didn't care about—something dramatic with subtitles—on purpose. He just wanted to sit next to her. Maybe hold her hand.
He hadn't expected how hard it would be to focus.
Riley was not only the sexiest girl he'd ever met, but she wasn't holding back. Every chance she could get she was complimenting him, getting close to him, touching him. Sitting down, her thigh immediately brushed up against his. Her perfume was everywhere. Her fingers trailed over his arm, then down... slowly.
"You seem tense," she whispered in his ear.
Chase's heart stopped.
"This should help," she added. "Think of it as meditation."
Her hand slipped into his lap, resting there for a moment, light and confident. Her fingers began to outline Chase's growing erection, an affectionate touch that only encouraged it to continue its growth. And then she slid her hand up toward his stomach, then back down, slipping beneath his waistband.
He didn't move. Couldn't. Heat surged through him, and he sat frozen, overwhelmed by sensation, by the knowledge that this was happening. His pulse pounded in his ears as Riley's delicate fingers wrapped themselves around Chase's cock, then began to gently slide up and down.
He tried not to gasp. He tried not to moan. His head leaned back on his seat as pleasure began to build and Riley began to pick up speed. Glad that the theatre was mostly empty, Chase found himself lost in a fantasy come to life, getting a handjob from not only the most amazing girl in the world, but also the girl who most of the internet would give a testicle to go on a date with.
And then he came. Shaking with an overwhelming amount of arousal, Chase emptied himself into his pants, filling Riley's hand. She encouraged him, allowing herself to become soiled with his eruption, thanking him when he was done. Closing his eyes, Riley's hand in his pants, Chase decided that this was the best date he'd ever been on. By the time they left, he couldn't even remember the name of the movie.
When Chase pulled up in front of Riley's house, he killed the engine but made no move to get out. The air between them was thick now—electric, charged. Chase was fairly certain that he was starting to fall head-over-heels in love with Riley, but was aware at how quickly he had come to that conclusion. The last thing he wanted to do was scare her off.
The drive back had been filled with soft laughter and flirty glances, but now that they were parked, the silence turned heavier. Expectant.
Riley unbuckled her seatbelt and turned toward him, one knee tucked up onto the seat, the hem of her barely-there skirt rising even higher. The glow from the dashboard lit her in soft hues—highlighting the shimmer on her collarbones, the glossy curve of her lips, the way her lashes framed her eyes like delicate lace.
"Thanks for tonight," she said softly, genuine gratitude in her voice.
Chase swallowed, his throat dry, unable to process that _she _was thanking him. Wasn't he the one whose pants were soiled? "No, thank you."
Then she reached out and touched his face—just a brush of fingers across his cheek, feather-light. Her eyes flicked down to his lips, then back up. She leaned in slowly, as though giving him time to stop her. He wouldn't have stopped her if the world ended.
Their mouths met.
It started sweet, tentative—just lips brushing. A taste. A test.
Then Riley exhaled shakily against his mouth and kissed him harder.
Chase's hand found her waist and pulled her close, fingers gripping the warm curve of her hip through the thin fabric. Riley tilted her head, deepening the kiss with a low, satisfied whimper that made Chase's head spin. Her lips were soft and slick and warm, and her hand was pressed lightly against his chest like she needed to steady herself.
She moaned softly into the kiss, letting it pour out of her, and Chase followed suit. All the months of obsession, of secret fantasies and whispered wants. Riley tasted better than he'd imagined. Felt better. Everything inside him fluttered, lit up, melted.
When they finally pulled apart, Chase's breath was ragged, his pupils wide.
"I've been wanting to do that," he said, his voice low, like a confession, "for so long."
Riley smiled—eyes shining, lips pink and kiss-swollen. "Me too. So bad."
She leaned forward and gave him one last peck—quick, teasing—then opened the door and stepped out, her skirt flipping up just slightly in the breeze.
"Text me when you get home?" she called over her shoulder.
Chase nodded like he'd forgotten how to speak. "Yeah. Definitely."
She blew him a kiss and disappeared into the house, leaving behind the scent of perfume and the imprint of her lips still tingling on his.
Chase sat there a moment longer, staring at the door, heart thundering.
He was beyond falling. He had fallen. Deep.
And he didn't want to stop.
What's next?
Disable your Ad Blocker! Thanks :)
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
- 5,860 Likes
- 2,189,497 Views
- 931 Favorites
- 620 Bookmarks
- 384 Chapters
- 73 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments