Tales of the Sapphire Carousel: Beyond the Bordello

Education was a lifelong journey.

That was Cheerilee's guiding philosophy, and one she tried to impart on all of her students. Learning didn't stop just because you were outside of the classroom, and learning wasn't just limited to reading books.

No, the world was filled with opportunities to expand one's knowledge of the world, to enrich the mind and broaden one's horizons. And Cheerliee tried to live that truth every day, to seek out new experiences so that she would have more to share when she taught.

Though, this was one experience she probably wouldn't be telling her students about.

Cheerliee took a deep breath as she stood at the entrance of the Sapphire Carousel. Her heart was pounding so hard it felt like it'd leap right out of her chest, and try as she might, she couldn't make herself step forward.

She shook her head, chastising herself internally. This wasn't the first time she'd ever been here— hell, this wasn't even the first time she'd been here this week. Of course, the reason for her visit was completely different from all her previous ones, but still. This wasn't some evil fortress of sin, and Cheerliee knew that very well.

"It's all in your head," she muttered to herself. "Institutionalized shame resulting from a lifetime of living under society's mores." Those words gave her just enough courage to walk forward and push open the door.

Inside, Aqua Swing waved at her. "Oh, hello Miss Cheerilee!" she said. "I didn't realize you were coming in today. Which one of the little scamps are you tutoring today?"

"I, umm..." This shouldn't have been weird. After all, Cheerilee had spoken to Aqua many times before, had literally just arranged next week's lessons with her yesterday. And yet... "I'm not here on business this time. Err, not my business. What I mean is that I'm here to hire a sex worker."

Aqua's eyes widened. "Oh!" Ever the professional, she quickly composed herself. "Right. Umm, let me lead you inside and you can see who's free right now."

"Thanks, Aqua." Cheerilee waited for Aqua to walk around the reception desk, trying to ignore the butterflies in her stomach.

Aqua noticed her distress, bless her, and patted her gently on the shoulder. "Hey, don't worry about it. You know everyone here's cool, and we're literally the last people who would judge you for doing this."

"I know that, intellectually," Cheerilee replied as they made their way towards the main area. "But it's hard to internalize."

"Well, if it helps, you're still not the most nervous client we've ever had to deal with." Aqua smiled. "At least you're probably not going to pass out the moment you see how sexy everyone is, I hope."

"No promises." Cheerilee gulped as Aqua pushed the door open. This was it.

From her previous visits, Cheerliee had learned that this entrance was used by potential clients who wanted to hire someone for the night. All the men and women who didn't have a prior appointment would wait here, dressed in their most enticing clothes as they readied themselves for any visitors.

Thus, when Cheerilee entered, she was greeted with the sight of a number of people she had come to know quite well, all posed provocatively and showing a scandalous amount of skin. Despite having spent time with most of them and thinking herself accustomed to their attractiveness, Cheerilee couldn't help but suck in a breath at the sheer beauty overwhelming her vision.

"Hey, everyone," Aqua said. "We've got a new client."

There was a ripple of surprise as the assembled employees all realized that Cheerilee was the client, which did nothing to help her feelings of self-consciousness. Fortunately, they were professionals, and as Aqua had said, had experience dealing with shy visitors. "It's lovely to see you again, Cheerilee," Shimmer said, stepping forward. "Please, feel free to take as long as you want to make your decision."

"Thanks, Shimmer," Cheerilee replied. For the first time since Luna had invited her here years ago, she allowed herself to look at her friend in a sexual light. Shimmer Glass was beautiful, with a body Cheerilee would have killed for, and a kindness that Cheerilee desperately needed right now. She would have been a good choice.

But, there was someone else in the room that made Cheerliee's heart race faster, someone that had, to her unjustified shame, fantasized about even before today. He was standing on the opposite side of the room, shirtless and showing off his muscular body as he leaned against a wall. Their eyes met, and an unspoken agreement passed between them as Cheerilee silently pleaded with him.

"I can take care of ya, if you'd like," Big Macintosh said, stepping forward.

Cheerilee nodded mutely before finding her voice again. "Y-Yes please, Big Mac."

He nodded and reached out a hand, which Cheerilee gratefully took, taking comfort in his strong, gentle grip. He led her away from the room, from the small crowd of men and women who were smiling and silently cheering her on, genuinely happy for her.

Neither of them said anything as they made their way towards one of the many bedrooms in the Sapphire. Big Mac pushed the door open, and gestured for Cheerilee to enter. "Ladies first," he said.

Cheerilee let out a nervous little giggle at that. "Thank you."

Once inside, Big Mac closed the door behind them. He turned back to face her, and Cheerilee felt her cheeks grow even warmer as her eyes roamed up and down his perfectly sculpted body, tracing the lines of his taut muscles.

"So, what happens now?" she asked, dreading and anticipating the answer.

Big Mac shrugged. "Well, Miss Cheerilee, you've got me for however long you're paying, so I should be the one asking you. Do you wanna go slow or fast?"

"I—" Cheerilee's voice caught in her throat, and she had to take another breath to calm herself. "I don't know, honestly. I've never done anything like this, and normally I'd be really excited for a new experience, but this time I'm also so nervous I can't really think straight." It sounded so pathetic to her own ears, and she burned with shame as well as embarrassment now.

"We can just talk for a spell if you need time." Big Mac sat down on the bed, and patted at the opposite side, keeping a respectful distance between them.

With a sigh, Cheerilee flopped down, lying on her back and staring at the ceiling. "This seemed like a really good idea this morning," she mumbled, picking up a pillow and hugging it to her chest. "I've been feeling really lonely lately and having... urges, but between teaching at the school and tutoring here I just haven't any time to find the right person for a relationship."

The bed was really nice, with soft, silken sheets that kissed her skin. "I mean, I could probably go to the bar and get sex if I wanted to," Cheerilee continued, running her hand back and forth along the bedding. "Even if I'm a frumpy old schoolmarm, it can't be that hard to find someone to have a one night stand with. But, I didn't really want my first time to be with some stranger. And then I remembered that I literally moonlight at a place that does this kind of thing professionally."

She chuckled dryly at that. "It seemed like the perfect solution. Just, pay someone I trust to give me the time of my life, and work out the tension that's been bugging me. But now, I'm terrified, and I don't really know why."

Big Mac stared at her, not saying a word. Still, his presence was a comfort to her, and the complete lack of judgement in his expression put her mind more at ease, let her think clearly for the first time since she'd left the schoolhouse intent on losing her virginity in this place.

"Okay, I know why," she confessed, her cheeks burning with shame. "I've studied enough sociology to know that I've been conditioned by society to think that sex is some transcendant expression of love, and that even caring this much about my first time is indicative of that conditioning. But it doesn't change the fact that I feel like I should be ashamed for winding up here, that if I was more desirable or something this wouldn't be happening. Which is dumb and wrong but sometimes all the facts in the world won't change our feelings."

Big Mac nodded, and Cheerilee knew he understood her.

"I just need to get over it," she said, determination welling up in her heart. "I came here to have a good time, and by God, I will. You are a very attractive man, and I can finally let myself think that, and I'm going to enjoy every moment of this."

Big Mac smiled, and Cheerilee felt a surge of pride as she reached out to stroke his leg with a hand.

"Thanks for listening." Her hand kept running back and forth along his muscles, and Cheerilee's anticipation grew. "I'm probably not the first person to have this problem, huh?"

"Eenope."

The familiar response made Cheerilee smirk. "Well, anyways, I'm glad you're such a good listener. I think I'm ready for the session now. So, do we just, uhh, start?"

"Eeyup." And then Big Mac's hands were on her, and Cheerilee was in heaven. "And yer not frumpy or old."

He probably said that to all the self-deprecating girls who hired him, but Cheerilee chose to lean into the fantasy of the experience, to allow herself to believe. "Oh?" she asked coyly, batting her eyelashes at him.

"Yer beautiful, Cheerilee," Big Mac replied simply. "And I'm real glad you're trusting me with your first time."

He leaned in to kiss her, and Cheerilee prepared herself for the most enjoyable lesson of her life, one that would be worth every penny she paid for it.