What Happens at Disney World Stays at Disney World - Cover

What Happens at Disney World Stays at Disney World

Copyright© 2025 by Cumming Up

Chapter 1

Fiction Sex Story: Chapter 1 - Justin thought he was doomed to spend his vacation at Disney World stuck with his family and riding kiddie rides. Instead, he spent the week living out fantasies most men only dream of.

Caution: This Fiction Sex Story contains strong sexual content, including mt/ft   mt/Fa   Mult   Teenagers   Consensual   Heterosexual   Fiction   Harem   First   Pregnancy  

“And if you look ahead, you can see the entrance!” The bus driver said over the loudspeaker. A bunch of kids cheered. I groaned. There it was, in big cursive letters: Walt Disney World. The home of Mickey Mouse. Somebody kill me.

“Oh come on Justin, it’ll be fun!” My little sister Ella said with a big grin on her face. I couldn’t blame her for being excited; this place was made for eight-year-olds like her, and I was excited to go when I was her age. But now I was fifteen, and there wasn’t much for someone my age to do. I was gonna spend the week stuck with my family, only doing stuff that Ella was able to do. I couldn’t wait for the week to be over. I kept my nose buried in my phone browsing Instagram until we reached the resort. That didn’t really make me feel better, because all I saw was pictures of my friends having fun, while I was stuck at kidland.

Finally, we reached the Contemporary Resort where we were staying, and made it to our room. Ella hurried into the bathroom to change into her “Disney clothes”. As she did that, my dad sat down next to me on the bed. “Look, Justin,” he started, “we know this isn’t really your cup of tea. So we’ve decided that you can go on your own this week.”

I looked up in surprise. “Really?”

“Really,” he said. “We’ll still want to see you for some meals and things, but we’ll let you do your own thing so you’re not stuck on kiddie rides all week. Sound good?”

“Works for me!” I said, suddenly in a much better mood. It still wasn’t the best situation in the world, since there wasn’t much for a teen to do here, but at least I could stay in the hotel room or something if I got bored. Ella came out of the bathroom wearing a Disney t-shirt, and she and my parents left to go to the Magic Kingdom. I browsed Instagram for awhile longer, then decided I’d try to have some fun of my own. I left the room and headed over to the Tower of Terror.

It was peak time, which meant the wait was almost an hour. I browsed Facebook as the line inched forward, until, close to the end of the line, I was interrupted. “Hey, are you with anyone?” said a voice. I looked up to see a girl about my age. I shook my head no. “None of my teammates would join me,” she said, “and this is a pretty scary ride. Would you mind if I rode with you?”

There was no way I was going to say no to this bombshell. Her blonde hair was in a ponytail, tied up with a white bow. Her clothes had to be three sizes too small; they looked like they were meant for a girl who was 4’9”, not what I guessed to be 5’9”. Her light blue t-shirt fit her like spandex and exposed her flat stomach. Her white soffe shorts were so short and tight they looked more like boyshorts, and could barely contain her perfect round ass, let alone her long tan legs. “Sure!” I said.

I silently kicked myself for sounding too enthusiastic, but she didn’t seem to notice. “Thanks!” she said. “I’m Courtney.”

“I’m Justin,” I introduced myself. “So you’re here with your team?”

Courtney nodded. “Well, squad, actually,” she said. “We’re the cheer squad for Browning Academy.” She pointed to her shirt, where the words “BA Cheer” were stretched tight by her very healthy chest (and judging by the points on the B and A, there was no bra underneath). “We’re here for the high school cheerleading championships,” she told me. “You’d think that with 15 other girls on the squad, I could find one that would go on this ride with me! Good thing I have you,” she said with a wink and a giggle. I was starting to really like this girl.

A moment later it was our turn to ride, and we sat down in the old-looking elevator. “I’m probably going to scream a lot,” she told me.

“Don’t worry about it, I probably will too!” I said. The elevator doors closed and we started to climb upwards while a creepy Twilight Zone introduction played. About halfway through the introduction the lights went out, and Courtney grabbed my hand. She didn’t let go for the entire ride. My mind was split, half-focused on the ride (it’s impossible to not be focused on a ride that makes you free-fall through the air), and half-focused on this gorgeous girl on my arm. Sadly, the ride was all too short, but luckily for me, Courtney never let go of my hand, even as we got up to leave. “That was fun!” she said as we walked out of the ride. “My teammates are at the Magic Kingdom, wanna go with me?”

“Sounds fun!” I said. At that point, I would’ve agreed to commit a murder with her. We boarded a bus to go to the Magic Kingdom, still holding hands the entire time. Courtney told me that she was 17, a senior, and the captain of the cheer squad. Her squad was one of the best in the country, and they made it to the championships here every year. The squad was staying at the Contemporary Resort like I was. I told her I was 15, a sophomore, and I played wide receiver on my high school’s varsity football team. “I was gonna say, you look like a football player,” she said, smiling. I was used to hearing that, being 6’2” and muscular, but hearing her say it was something else.

The bus stopped at the Magic Kingdom and we got off. “Hey, I’ve got an idea, let’s go ride the Haunted Mansion!” Courtney said as she pulled me by the hand. The Haunted Mansion seemed a little kiddish for my tastes, and I thought the point of coming to the Magic Kingdom was to meet up with her teammates, but I wasn’t about to say no to her.

There wasn’t a line for the ride, so we went right ahead into the elevator that brought us down to the carts. In the elevator was an introductory monologue kind of like the one in Tower of Terror, and toward the end the lights went out. As soon as they did, I felt Courtney put her lips on mine and wrap her arms around my neck. She was far more experienced than the other girls I’d kissed, and I enjoyed her skilled use of tongue for about ten seconds until she quickly broke it off, right before the lights came back on. She grabbed my hand again and led me through the door into the cart area, and we stepped onto the moving walkway before sitting down into our cart, which was concave and came up around the sides.

As soon as the ride started, Courtney was on me, rubbing her hand on my shorts and running her tongue up and down my neck. “Don’t worry,” she said to me, “no one can see us.” I looked around, and sure enough, I could barely see anything, let alone anyone else. “I have a question,” she said as kept rubbing me. “Have you ever fucked a girl?” I shook my head no. I’d gotten head from a few girls before, but never sex. She reached into the waistband of her shorts and pulled out a condom. “Do you want to?” she asked me. I tried to keep my cool, but I’m pretty sure I nodded like a bobblehead doll. She smiled. “Good.” She pulled down my shorts, springing my cock free, and I saw her eyes go wide. I wasn’t surprised; the girls that had given me head all had the same reaction. I was about nine inches hard, and pretty thick. “Holy shit,” she whispered to herself, “this is gonna feel fucking amazing.” She threw the condom out of the cart. “I need to feel this thing raw,” she said. I was stunned. “Don’t worry,” she said, “I’m on the pill.” Actually, what stunned me was that a girl like her needed to feel me without a condom, but it was good to know there wouldn’t be a surprise in nine months.

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