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Chapter 43 by ShimoDragon
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Beach Date
Chase sat in his car outside of Riley's place once again. He was nervous about seeing her again. He had thrown on an unbuttoned Hawaiian shirt to go with his swim trunks, worrying the whole time that she might think he looked lame. He didn't know fashion too well, not like she did. Part of him wanted to go back home and rethink his clothes one more time, but the part of him that missed her was much stronger. He wanted to see her again, to be with her.
To touch her.
As that thought went through his mind Riley walked out the door. His heart stopped. She was angelic. She wore a short sundress that was cinched at the waist and fluttered around her upper thighs along with a pair of strappy heeled sandals and a tote bag. His eyes were quickly drawn away from her outfit though, as they came to settle on her face.
She had told him that she was getting work done but seeing it now was something else entirely. She was still Riley but it was like her femininity had been cranked up past 100. She had been beautiful before but now she was outright stunning! She locked eyes with him as she walked up with her rolling hips and smiled. He smiled back as he shifted awkwardly in his seat. Chase was already getting hard just from looking at her.
He was so dumbstruck by her beauty that he forgot to get out of the car to let her in. Thankfully, Riley didn't seem to mind as she let herself into the passenger seat. "Chase! It's so good to see you! Well? How do you like the new me?"
She framed her face in her hands while Chase stammered slack jawed. "Y-you look totally... just totally unbelievable."
"You're so sweet Chase." Riley giggled and leaned in to give him a light kiss on the cheek. "S-sorry, was that too forward?"
Chase's head was spinning but he shook his head. "N-no. That was... nice."
He turned to her and gently grabbed the back of her neck, to pull her in for another kiss. Deeper and passionate. She moaned softly into his lips as she reached to caress his cheek. Chase wasn't sure how long they sat there kissing, but eventually they broke apart.
"I missed you Chase." She spoke with a smile that could melt ice.
"I missed you too Riley."
The pair arrived at the beach after a short drive. They only made simple small talk along the way but just being next to Riley made Chase happy. The beach itself wasn't very busy. Summer was ending so most people weren't interested in going to the beach, but it was still plenty warm for those who wanted to get one last trip in. Riley had told Chase that she hadn't gone all summer so he knew he had to take her.
They both stepped out of the car and started walking out onto the sand. Chase had brought a couple of beach chairs which he quickly unfolded before turning to Riley.
"This spot looks as goo-" His voice caught in his throat at the sight of her. She was pulling off her dress, in the middle of the beach no less!
Riley spotted Chase's shock and giggled. "I'm wearing a swimsuit underneath, silly! No need for you to panic."
Chase's shock didn't go away when he saw the swimsuit though. In fact, it got even worse! There Riley stood in the tiniest microkini he had even seen. Just two tiny red triangles to cover her chest and a third for her groin all held up by nothing but delicate string. Chase had spent a lot of time imagining the finer details of Riley's body but this left little to the imagination.
"W-wow. You're- woah." Chase struggled to form a coherent thought while he tried his best not to stare at Riley's boobs.
The tiny strips of fabric she wore over them did nothing to restrain their movement as she replied. "Thanks, you're looking pretty good yourself. But enough of the flattery, I need to ask you a favor."
"Anything! Erm- I mean, what do you need?"
"Well, I haven't had a chance to put on any sunscreen yet. I was busy getting ready all morning..." She leaned in to whisper in his ear. "Could you... rub it in for me?"
A tantalizing shiver ran down Chase's spine at her words. "Y-yeah! I can do that for you."
She handed a bottle to him and laid down on one of the beach chairs. "Let's do my back first."
For a moment Chase was frozen. The girl of his dreams was laid out before him like a piece of art and all he could do was marvel. Her perfectly round ass covered by nothing more than a couple strings and her huge tits spilling out the sides of her top as she lay down. She was the sexiest thing he had ever seen.
Shaking his growing arousal from his mind, Chase squeezed a lob of sunscreen into his hands and rubbed them together. When he had been hoping to touch Riley earlier he never imagined this might happen. After one last moment of hesitation he began to apply the sunscreen.
He started at her shoulders, working in the lotion as thoroughly as he could. He slowly moved down her back as he went. He couldn't believe how small her waist felt underneath his hands. She squirmed a little as he dragged his fingers along her sides.
After the waist was her... butt. Chase audibly swallowed as he prepared himself. He squeezed another dose of lotion into his hands and started kneading it into Riley's dump truck of a backside. She tensed up a little at his touch and he swore he heard her whimper out a moan but she did nothing to stop him. So he continued.
He made sure to lather up every inch of her sizable ass before moving further down to her legs. He could feel the toned muscle just beneath the layer of supple and jiggly skin as he caressed her thighs. Eventually he finished off with her calves and the job was done.
And suddenly, the date returned to normal as though that wasn't one of the most erotic experiences Chase had even taken part in. Riley chatted with him about her plans for future social media content, about brand deals that were being offered in her DMs. She never talked about herself for too long though, she always brought the conversation back to Chase eventually. She would ask about how things were with the football team, or where Chase liked to go out to eat implying that she wanted him to take her at some point.
After a while Riley flipped over onto her back. "Time to switch sides, I'm gonna have such a killer tan after today! Wanna help me apply again?"
Chase's eyes went a bit wide at that, realizing if he did her front he would definitely end up groping her chest while he rubbed in the sunscreen.
Riley seemed to come to the same realization, because she hastily withdrew the offer as she blushed. "J-just kidding! You're a lot easier to tease than you look Chase, o-obviously I was joking just now..."
He couldn't tell for sure, but it seemed like Riley was a little disappointed as she applied her sunscreen herself...
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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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