Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 6 by Redrover5890 Redrover5890

What's next?

The new plan

Oh, babe,” Devon said with sympathy in her voice as she approached the man sitting on the closed toilet. “I know, I know. But we’re both still alive and together—that’s what matters.” Devon squatted in front of her husband, looking up at his covered face.

“I know, but what do we really know about this Samuel guy? I mean, you guys used to date?” Milo sat up straighter, raising his head out of his hands. “He’s clearly still in love with you.”

“Love?” Devon responded with surprise. “I don’t think so. I mean, we only dated for like a couple of months,” she said reassuringly. “You are my husband, and I love you.”

“Regardless of your feelings, he still has something there for you. I mean, you heard how he spoke to me. Clearly he hates me.”

“I mean…” Devon tried to argue with Milo, but he wasn’t wrong. Samuel did order Milo around a lot, and did it rather rudely.

“And, I mean, come on. He only created two extra identities for us—both of which are women,” Milo continued, trying to persuade his wife not to follow through with his new rival’s plan. “Why didn’t he give me a male identity? It doesn’t make sense. Unless he wanted to humiliate me to get you back.”

“But I know Samuel. He’s a go—”

“Babe, I love you, I do. But you can be way too trusting,” Milo said, leaning back. “I know guys like him—guys who will do whatever it takes to get what they want.” Milo knew guys like this because he was a guy like this. He could see doubt begin to creep into his wife’s mind. Time for the final touch. “And babe, honestly you could be right, but it also hurts that you would side with your ex over your husband’s own feelings.”

“I mean, it does seem fishy…” Devon admitted. But she also knew they didn’t have many choices. “But we don’t have a lot of options, so let’s at least hear the plan. That way we can have a dialogue. What is it your dad always said? A dialogue is all you need for a negotiation?”

It wasn’t the conclusion Milo had hoped for, but she was still on his side. So he knew he still had a chance to get out of this.

“Okay,” he said, standing up. “Let’s hear what he has to say.”

Samuel heard the bathroom door click open, drawing his team’s attention. He was impressed—and a little disappointed. Impressed that Devon had talked Milo into hearing the plan, and disappointed because he’d been hoping Milo would quit and his problem would be solved. Nonetheless, he was determined to humiliate this boy in front of his woman.

“Okay, I think we’re ready to hear more of the plan. But we haven’t agreed to anything yet,” Devon said, trying to act as mediator. “If this plan doesn’t work, we’ll need to compromise.” Milo wanted to interject and immediately reject any plan involving him in a skirt, but he knew he had to let Devon act as their spokesperson.

“Umm, okay, whatever,” Natalie said. “So for the next two weeks, we will be boarding Escape to the High Seas, an all-inclusive adults-only cruise.”

“A fucking cruise? Are you serious? This is what my tax dollars pay for?”

“Milo,” Devon pleaded.

“Yes, a cruise,” Natalie continued. “Cruises are self-contained environments—limited outliers. We know everyone, the ship crew included. It makes it easier to keep you safe and monitor the environment. Now this is the two-week Spring Break 2025 celebration—I think it’s called Mayhem in March. Anyway, I’m going undercover as Heather. She’s friends with Paris, another influencer-model type. And Samuel will be Hector Brink: investor, inventor, self-made man.”

Natalie paused, glancing at Milo, expecting more complaints, but he stayed silent.

“So, our backstory is this: Hector is with Paris. It’s your typical sugar-baby, sugar-daddy relationship. He’s paying to take Paris, her friend Monica—” Natalie pointed to herself—“and her kid sister Becks.” She subtly pointed at Milo.

Devon felt Milo clench his fists under the table—furious at being referred to as a kid, as a sister, and a sister to his wife.

“Paris and Monica were brought along for obvious reasons,” Natalie continued.

Milo sighed loudly, rolling his eyes.

“We’re to party with Hector. That’s our cover story, but it also places us in the most crowded areas on the ship—nightclubs, special events, nightlife. Becks, being more scholastic, will stay on the outside, get to know guests that way. It will also be easier to monitor them because they’ll be doing the less crowded events—relaxing things. The winery excursions, aerobics classes, movie nights.”

Milo could not believe how boring that all sounded. While Samuel partied on spring break with two hotties—one of which was his wife—Milo would be stuck doing boring stuff while dressed as a young woman. This only convinced him further that Samuel was purposefully trying to push him out and wedge himself between him and his wife.

“So everyone—that’s our plan. Thoughts?” Natalie asked after finishing the details. Devon was a little jealous of Milo’s cover story. It sounded like he’d be asked to travel and see parts of the world she always dreamed of. She was also uncomfortable pretending to be Samuel’s “sugar baby.” She found him very attractive—who wouldn’t?—but she was married to Milo, and it didn’t feel right. It also made some of the things Milo had said in the bathroom seem a little more true. She needed to help her husband.

“Hold on,” Devon said, breaking the silence. “I don’t like this.”

“Like what, Devon?” Milo asked, surprised she would interject.

“This plan. I don’t want to play some sugar baby.” Devon knew Milo’s pride wouldn’t let him act threatened, not when he was already so intimidated by Samuel. She had to protect her husband’s feelings. “I want to be Becks. And I think Milo should be Paris!”

Devon said it like a sudden revelation. To her, it was perfect. Milo would go undercover as a sugar baby—surrounded by two agents and kept very safe. He wouldn’t have to watch his wife flirt with her ex. And he would spend more time with Samuel, learning that he could be trusted. Plus, she’d get some adventure and travel she’d always wanted.

Sure, Milo would hate acting like Samuel’s sugar baby, but he could get over it. He wasn’t homophobic or anything. She’d watched him kiss another man on a dare. He’d survive.

“You want to switch identities with Milo?” Samuel asked, confused. He hadn’t expected Devon to suggest this. Why wouldn’t she want to be closer to him? Why would she want Milo closer to him? He felt blindsided.

“Yes. I think that would be best,” Devon said, squeezing Milo’s hand. Milo, still in shock, just stared at her.

“Milo, you can’t agree,” Samuel said, for the first time hoping his enemy would take his side.

“That’s a terrible fucking idea!” Milo yelled. “You want me to pretend to be a woman—with him? His sugar baby? Do you know what that means? It means he’s paying me to be his arm candy—his bimbo! You think I’m suited for that?”

Milo finally stopped to catch his breath.

“Do you think I’m suited for that?” Devon snapped back. The room went silent. Milo often mistook her kindness for naïveté. She wasn’t Ivy-League educated, but she wasn’t a bimbo. She hated that word.

“No!” Milo said quickly, trying to defend himself. “But don’t be ridiculous—you’re at least a straight woman!”

“Milo, you said you didn’t trust Samuel. Well, now you don’t have to worry. You two will be together. That’s what made you uncomfortable, right? You thought he was trying to steal me away.” The word bimbo had pushed Devon past diplomacy. “So which is it? Do you want me with Samuel, or do you want to be with Samuel?”

Milo paused, weighing his options. He sure as hell didn’t want to be with Samuel for two weeks. But he didn’t really care about Devon being with him either. And if he was honest. He thought Samuel could keep his wife safe while Milo got to flirt with some liberal girls who maybe curious or even turned on by a femme version of himself. He didn’t think his wife would cheat, she was loyal even if he wasn’t. But a femme version of himself could maybe ruin this trip for that jackass Samuel.

They couldn’t actually make him look like a woman—he was a man at his core; makeup wouldn’t hide that. He would be with Samuel. He would play the sugar baby. He would look ridiculous—a dude clearly in drag acting flirty. It would ruin Samuel’s fun. Everyone would think Samuel was gay, and he’d have to play along. Perfect.

“I’ll be with Samuel,” Milo said, a slight evil smile creeping onto his face.

No one saw Milo’s smile—except Samuel. Samuel had to think fast. Milo was playing a game. He’d already figured out what Samuel was trying to do. Milo was smarter than he’d given him credit for. Samuel assumed Milo was planning some kind of “gay chicken.” Fine. If Milo wanted to play, Samuel would play.

But there was one thing Samuel knew that Milo didn’t: they had the newest in personal-enhancement technology.

Lazarus tanks

What's next?

More fun
Want to support CHYOA?
Disable your Ad Blocker! Thanks :)