Star's Crossed Lovers

BY : GeorgeGlass
Category: +S through Z > Star vs. The Forces of Evil
Dragon prints: 16530
Disclaimer: I do not own Star Vs. the Forces of Evil or its characters. I made no money from writing this story.

Star’s Crossed Lovers (or, Magical Princesses Make the Best Wingmen)
by George Glass

Summary: Star and Marco make a five-step plan to help each other get with their respective crushes. But there are others who want the magical princess and the karate boy for themselves—and who have plans of their own.

Spoiler alert: This story takes place after the end of Season One and contains major spoilers for “Blood Moon Ball,” “St. Olga’s Reform School for Wayward Princesses,” and “Storming the Castle,” as well as minor spoilers for other season 1 episodes.

Note #1: I started writing this story before Season Two began to air, and I fully expected that at least some of the events of season 2 would contradict what happens in the story. This proved to be the case, to such a great degree that I didn't even try to reconcile the story with season 2 canon. Thus, this story is canonical with season 1 only. Consider it an alternative version of season 2.

Note #2: If you are so kind as to leave a review, I will respond to it here:

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Chapter 1: The Plan

It was a sunny spring day, but both Star and Marco were shuffling their feet glumly as they walked home from school.

“I don’t get it,” Marco said. “I’m finally at the point where I can say hi to Jackie on a daily basis, and even speak a complete sentence or two to her, but that’s as far as I can get. I try to say more, and then I choke. How am I ever gonna get her to go out with me if I can’t even have a normal conversation with her?”

“Tell me about it,” Star groaned. “I mean, I had one phone conversation with Oskar for, like, ten seconds, but when I think about talking to him in person, I just freak out!” Then, sighing, she added, “It’s not like I have trouble talking to other people.”

“Yeah,” Marco said, “but I could see how it would be tough with Oskar. He’s a man of few words.”

They reached home. The driveway was empty, indicating that Mr. and Mrs. Diaz were both out.

“Maybe you could give me some advice?” Star asked.

Marco became lost in thought for a moment, then said, “No.”


“No,” Marco repeated as he unlocked the front door. “Advice isn’t going to cut it. For either of us. We need to take this to the next level.”

Star put her fists to her mouth in excitement.

“I love the next level!” she cried as Marco shut the door behind them. “Tell me the plan.”

“We need to become”—Marco paused dramatically—”wingmen!”

“Ooooh!” Star exclaimed. “I’ve got wings! And you’re…totally making progress on the man thing.”

“No, wingmen means that we help each other get with the people we want.”

“That sounds amazing! How do we start?”

“First,” Marco said soberly, moving to the center of the living room, “we seal our agreement with the wingman fistbump.”

Marco and Star each raised a fist. As soon as they made contact, Marco opened his hand and moved his thumb and pinky finger like flapping wings as he cawed like a crow. Star did the same, looking slightly awed.

“Wow, Marco,” Star said. “Thank you so much for including me in what’s obviously an ancient and important Earth ritual.”

“Actually, it’s just something Ferguson showed me once,” Marco replied. “And I think he made it up.”

“Well, it’s still pretty cool,” Star said. “So what’s next?”

“Next, we come up with a plan. Getting you with Oskar and me with Jackie is going to be tricky, so I figure the plan will need to have about twenty-five steps.”

“Hmm, I prefer zero steps.”

“A plan can’t have zero steps, Star.”

“Okay, one step.”

“How about eighteen?”



“Five steps, final offer,” Star insisted.

“Okay, fine, we’ll make a five-step plan. Man, you drive a hard bargain.”

“Thanks! My mom taught me.” Then, imitating her mother’s decidedly royal tone of voice, she said, “‘Star, when negotiating with trolls, never accept the first offer, no matter how many severed goblin heads they’re willing to part with.’” Marco snickered.

“Okay, so what should the first step be?” the boy asked. “If we’re only going to have five, then each one will have to be pretty big.”

“Well, since talking to them seems to be a problem, we should probably start there,” Star replied.

“Good idea,” Marco said.

From a side table drawer, he pulled out a yellow legal pad and a pen and wrote, “Step One: Engage in Conversation.”

“Kewl,” said Star. “So how does your being my wingman help me talk to Oskar?”

“I have some ideas about that. But let’s figure out the rest of the steps first. What about Step Two?”

“Asking them on a date, obviously,” Star answered eagerly.

“You don’t think that’s kind of ambitious for the second step?”

“This whole thing is ambitious. That’s why it’s awesome.”

“Yeah,” Marco agreed. “This is like the Manhattan Project of dating.”

“Manhattan Project? Was that something you had to do for school?”

“In a way,” Marco said as he finished writing “Step Two: Ask Them Out” on the legal pad. “The moon landing would probably be a better analogy, though: Fewer people got blown up. Anyway, what would Step Three be?”

“Hmm...I guess we need the first date to go awesomely so there can be future dates.”

“Awesome first date? Well, we’re shooting for the moon anyway, so we might as well make ‘awesome’ our target. But how do we know if we’ve succeeded? I mean, how do you measure awesome?”

“Everyone knows awesome when they see it,” Star insisted. “If you need to measure it, it’s not awesome.”

“I guess I can live with that,” Marco said, scribbling “Step Three: Awesome First Date” on the pad. “So I guess Step Four has to involve additional dates.”

“Works for me,” Star said.

Marco wrote “Step Four: Additional Dates” on the pad, then looked up at Star.

“Okay, we’re down to the last step. But this one has to be something definite—something that says ‘Mission Accomplished.’”

“Hmm...Happily ever after?”

“It’s good, but it’s not exactly a hard endpoint. We need a goal, so we can say ‘yes, we’ve done it,’ or ‘no, we haven’t done it.’”

“All right then, how about this: The Deed.”

“The Deed?”

“You know what I mean,” Star said, beaming with nervous excitement.

“Just in case this is another inter-dimensional misunderstanding, spell it out for me.”

Avoiding eye contact, Star said, “You know, sheathing the sword, burying the bone, riding the unicorn…”


Blushing, Star said, “Sex, Marco, I’m talking about sex.”

Marco’s eyes widened. “You remember that we’re fourteen, right?”

“On Mewni, that’s…almost old enough. I mean, my parents were only fifteen or sixteen when they first did it, and that was on their wedding night. And now I’m going to stop talking about my parents’ sex life.”

“Wait,” said Marco, “if your parents got married when they were teenagers, why did it take them so long to have you?”

“I don’t know, something about my mom’s uterus being a hostile environment for- Gah, I’m doing it again!” Star shouted.

After taking a moment to calm down, she continued, “My point is, if we’re shooting for the moon anyway, we might as well make The Deed our goal, right? Besides, endpoints don’t get any harder than that. Although you might,” she added, sniggering.

Marco took a deep breath.

“Okay,” he said, exhaling. “The Deed it is.”

Marco wrote “Step Five: The Deed” on the legal pad. Then he tore the sheet off, folded it in half, and put it in an inside pocket of his hoodie.

“You realize this plan is completely insane, right?” he said.

“Yup,” Star replied with a grin. “That’s why it’s gonna work.”


They talked for more than an hour, discussing the details of Step One: Engage in Conversation. Marco, they decided, would go first, catching Jackie at her locker in the minutes between lunch and fifth period. Then, after school, Star would talk to Oskar at his usual hangout spot in the parking lot.

“Now, I don’t claim to know a lot about Oskar,” Marco said, “but I know his type: the artistic loner.”

“Which is totally cool, but how does it help me?”

“The artistic loner isn’t usually much of a talker—unless you can get him talking about his art.”

“So, talk to him about music. Good idea.”

“Then I, as wingman, will walk by while you’re talking and say something that makes you look cool. Well, cooler.”

Star grinned hugely. Then her grin faded a bit.

“But…I’m still worried that I’m not cool enough for him.”

“First, you’re super cool. And second, Oskar won’t care how cool you are.”

“How do you know that?”

“Star, there’s two kinds of cool people in the world: the ones who work at being cool, and the ones who just are cool. Oskar’s the second kind, which means that he doesn’t need to hang out with other cool people in order to be cool himself. My point is, you don’t need to worry about coolness at all. Because he doesn’t.”

“Then maybe you shouldn’t worry about it, either,” Star said. “Because I think Jackie is the second kind of cool, too.”

“But what do I say to her?” Marco asked. “When I try to wing it—no pun intended—it always ends in me contracting either instant laryngitis or diarrhea of the mouth.”

“Ew,” Star replied. “We’ll work on your choice of metaphors later.”

“Sorry. I get that from my Grandpa Rogelio.”

“The one who’s coming to visit?”

“Yeah. Anyway, back to the Jackie question. What can I talk to her about?”

“Well, we know she likes skateboarding,” Star said. “Let’s use that.”

“Yeah, but I’m nowhere near as good at it as she is, so it’s not like I can impress her by talking about my tricks.”

“Then let’s use that,” Star replied. “Like my dad says, ‘Find a way to turn your weakness into a strength.’ Of course, he was talking about wrestling minotaurs, but, you know.”

“So how do I do that?” Marco said. “The weakness-into-strength thing, I mean, not the minotaur-wrestling thing.”

Grinning, Star replied, “I may have an idea…”


That evening, after his parents had gone to bed, Marco felt too restless to sleep. Quietly, he went across the hall and tapped on Star’s door—which promptly flew open to reveal a grinning Star.

“Hey Marco!”

“Shhh,” Marco said, putting a finger to his lips.

“Oh, the noise thing, sorry,” Star whispered. “I never have to worry about that at home—my mom’s snoring covers up pretty much everything. So what’s up?”

“I’m nervous about talking to Jackie tomorrow.”

Star ushered Marco into her room and closed the door. “C’mon,” she said, “what’s the worst that could happen?”

“She could tell me to get lost, and my heart could implode like it’s being crushed by Man-Arm. You know, with his...non-man arm,” he added lamely. “Project Wingman could go down in flames right then and there.”

“Marco,” Star replied, “you’ve got to quit thinking about how it could go wrong and start thinking about how it could go right.”

Marco looked at her for a moment, then began nodding slowly.

“Yeah,” he said. “Yeah, I need to visualize it, like when I’m breaking boards at the dojo. Good idea, Star.”

“And it wouldn’t hurt to psych yourself up a little,” Star added. “Think about how awesome it’s gonna be to date Jackie. I mean, I hear you moaning her name now and then through your door late at night. What are you thinking about when you do that?”

“Um, we need to have a talk about boundaries.”

“Yeah yeah, later. Tell me what you want to do with Jackie.”

“Okay, uh, well, I usually think about her being in my room, and we’re, like, making out on my bed.”

“Sitting up or lying down?” Star asked eagerly.

“Lying do- Oh, jeez, Star, I can’t look at you and talk about this stuff.”

“Then close your eyes and talk about it.”

Marco looked like he was about to protest. Then he sighed, closed his eyes, and went on. “We’re lying down, and, and she’s on top of me.”

“What does she feel like?”

“Soft...and warm. And her hair smells nice. And her lips...they feel really good on mine.”

“Uh-huh. Go on.”

“We kiss for a while,” Marco said, starting to loosen up. “And then I reach under her shirt and feel her up.”

“Mmmm. What do you think her boobs feel like?”

“I don’t know. I’ve never touched a girl’s boob before.”

“Oooh, you’re gonna love it. They’re really, really soft. I mean, mine are, and I’ve barely even got any,” she said, shoving her head down the neck of her dress to look at her own chest. Then, her head popping out like that of an enthusiastic turtle, she continued, “But Jackie’s look like nice little handfuls. So what happens then?”

“Well, at some point, I take off her top, and then, you know, her bra...and my own shirt, too, so we’re just in our underpants.”

“Mmm, lots of skin on skin.”

“Yeahhhh,” Marco breathed. “And then I kind of…roll her over, while we’re kissing, so now I’m on top of her, and she’s sort of, you know, spread out underneath me.”

“Atta boy.”

“And then, well, it’s like the underwear is just gone, and I’m, I’m just...easing into her….”

Suddenly, Marco opened his eyes and awkwardly dropped his hands in front of his crotch as he finished, “I think I’m gonna stop there.”

“Wow, Marco,” said Star. “You’ve got what my dad calls a healthy libido.” Stopping and catching herself, Star hissed, “Why the pegasus feathers do I keep talking about my parents?! Please forget what I just said.”

“Already done,” Marco said, actually rather grateful; the mention of King Butterfly had tamped down his erection somewhat.

“Feeling psyched up now?”

“Um, definitely. But what about you? What’s your fantasy about Oskar?”

“Well, it’s, I mean, it’s a little…uh…”

“C’mon, Star, I opened up to you just now, and it really helped.”

“It’s just…you’re going to think it’s weird.”

“Star, if I had a big problem with weird, we wouldn’t be best friends.”

“Aw, Marco,” Star said with a big smile. “Hugs!”

She grabbed the pajama-clad teen and pulled him to her. Marco’s mind suddenly flashed on the thought of Jackie’s naked body against his.

“Uh, Marco?” Star said.


“Is that your boner poking me in the leg?”

“Um...yeah. Sorry.”

“No, no, all the boneriffic talk was my idea. Besides, if you could feel how hard my nipples are right now-”

“Uh, I can, actually.”

“Oh. Wow. So...this is pretty much the most awkward hug ever.”

“Pretty much.”

“Maybe we should let go now.”

“Let’s do that.”

They disengaged, neither of them looking directly at the other as they separated. Marco managed to seat himself on Star’s narrow sofa in a way that minimized the visibility of his erection through the thin fabric of his pajama pants. Star sat down an arm’s reach away.

“Soooo,” Star said, “do you still want me to tell you about, you know, my Oskar fantasy?”


“Well…you know how he has those pointy little teeth?”

“Yeah, I’ve wondered about those. You think it’s some kind of dental appliance, or-?”

“Do you want to hear this or not?”

“Sorry. Go on.”

“So...I like to imagine that we’re at the Chillaximus Spa in the Cloud dimension. We’re wearing fluffy white towels, and we’re giving each other hot-oil massages.”

“Oooh, slippereh,” Marco said, getting into the groove of Star’s fantasy—chiefly because he couldn’t help but think about how much he would like to do such a thing with Jackie, his oiled hands sliding over her lovely naked body.

“Yeahhhh,” Star continued enthusiastically. “So, I’m lying on one of those massage tables—you know, the kind they cover with cloud-sheep skin so they’re nice and comfy…”

“Um, sure,” Marco replied, not wanting to interrupt with questions.

Star closed her eyes, seemingly envisioning the scene so as to better describe it.

“He’s massaging me, and I’m feeling all nice and relaxed as he works his way down my back...down and down and down...all the way to the edge of the towel that’s covering my butt…”

“Uh-huh…” Marco said, also closing his eyes as he wondered: What would it be like to massage Jackie that way, his fingers slowly working their way down her back, toward her tantalizing backside? How far would she let him go? To the edge of the towel? An inch beneath it? Farther? God, what would it be like to touch her beautiful, womanly ass?

“And then his hands just slide under the towel...and he starts massaging my butt…”

“Niiiiice…” said Marco, now completely swept up in imagining the feel of Jackie’s warm, soft, oil-slippery bottom-cheeks in his hands.

“And then,” Star went on, “he bends down, and he starts biting my butt.”

“Wait, what?” said Marco, jarred out of his fantasy.

“Not hard enough to break the skin or anything,” Star clarified. “Just tiny nips, with those pointy little teeth of his,” she sighed.

“Oh. I guess I could see that,” Marco said, closing his eyes again.

“So he just nips and nips, starting from the top of my butt and slowly going down, and down, and down…”

“Uh-huh,” Marco said.

“And then...when he gets all the way to the bottom...he just shoves his face in there and starts eating my-”

“Whoa!” Marco gasped, his dick suddenly painfully hard. “I think I need to go to bed now!”

Star opened her eyes. Her cheek-hearts turned a deeper shade of pink as she saw the massive tent that Marco had involuntarily pitched in his pajama bottoms and was now trying and failing to hide.

“Oooh, I’m sorry, Marco,” Star said with a half-suppressed grin as she courteously averted her eyes. “I didn’t mean to get you that psyched up.”

“Yeah, well,” Marco said, stumbling toward the door, “you, um, tell a good story.”

“Thanks! See you in the morning.”

Despite his discomfort, Marco smiled. “See you tomorrow.”

He was just taking a left out of the doorway to go to his own room when Star said, “Oh, and Marco?”

He paused. “Yeah?”

“If we do this thing right and stick to the’ll have Jackie spread out underneath you before you know it.”

“Aw, come on!” Marco cried, staggering out of the doorway so that Star wouldn’t see him grab his aching crotch.

“Sorrrryyyy!” Star sang unapologetically.

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