Training Sweetie

James was nervous about tonight. He could imagine so many ways it could go wrong. Somepony could probable figure out what was going on and send him to jail, easy. That’s why he had a plan he intended to tell Sweetie about.

He found Sweetie in her room reading a book on her bed laying down. He knocked on the open door then walked in. Her room was rather spacious but fairly bare. Considering it was her sisters workplace/house he supposed it made sense. It had a toy chest at the foot of her bed and a cabinet with books, a desk, and a closet, not much else, “Hey Sweetie, we need to talk before the date later tonight.”

She put down her book and looked up to him, “okay.”

“You remember when we talked about other ponies and how they might not like the idea of us dating each other?” She nodded, “Well, let me reiterate that I might get sent to jail for dating you.”

“I know. I don’t want you to go to jail.“

“Sweetie as happy as I am to hear you say that. It doesn’t change the fact that somepony could find out we’re dating when we’re going out on a date.” Sweetie looked at him blankly. He couldn’t tell if she already thought as much yet or had yet to once again connect the dots, “which means I could get sent to jail if they find out.”

“WHAT!?” She yelled hopping to her hooves, “but then, what about our date?”

“I have a plan. Do you want to hear it?” She nodded, “I think we should play a game.”

“What game?” she sat down.

“Umm,” he contemplated while scratching behind his head, “I don’t have a name for it yet, but it has a objective. We only win if we don’t get caught,” she looked at him blankly, “the objective is make other ponies believe that we’re on a date but it’s a one time date.”

“But if ponies wouldn’t like us dating then why would they be okay with us being on one date?”

“Perception Sweetie,” he said with a grin, “we’re going to sell them a story.”

She gasped and clapped her hooves together, “We’re going to need paper and pencils.”

“Huh?”

“For the story.”

“Oh, No Sweetie. I mean we’re going to act out the story. I mean, I guess you can write it down if it’ll help you remember it, but you can’t take it with you. So here’s what I was thinking-”

“Wait! Let me get a paper and pencil.”

=============================================================================

It was almost time for their date and James could hardly believe he was still going through with this. Hell, even two days ago he’d never imagine dating a filly. Those crab ponies really did a number on his psyche. He still felt like he had adrenaline running through him.

James felt awful about what he did to Sweetie. She just looked so cute. He wanted to take her, so he did, at least very briefly with his middle finger. He regretted it. He let his worst desires get the better of him.

Sweetie had treated it like her sister spit in her cup and told her to drink it. She treated it like the weird kid at school who’d eat a bug for a dollar. She clearly didn’t understand what he was really doing and why. That fact really nagged at him.

At any rate, Sweetie had been upstairs for the last thirty minutes ‘getting ready.’ His wonder of what that meant didn’t last much longer as she walked down the stairs.

“How do I look?” She asked. She had a gorgeous dark purple dress on. She also put on stuff that left him conflicted. On one hand it screamed insecure whore which apparently was a slight turn on for him. On the other hand he mostly found it funny, because she was a filly.

He resisted his urge to chuckle, “Sweetie why’d you put makeup on?”

“Because I wanted to look my best,” she answered, “it looks good right?” She said producing a small mirror and checking herself.

“Sweetie you know I like being honest with you, so let me just say you’re very beautiful without any makeup on. With that said, you do look hot with makeup.”

She blushed, “I do?”

He smiled, “Of course you do but,” he held out his hand to show that he meant what he said next, “for future reference you might want to use less makeup, and lipstick because you look hot for maybe not the best of reasons. Now you remember the game right?”

“Mhmm,” she nodded.

“Good, let's get this date started.”

They left the Carousel Boutique and headed towards their destination. The sun was just about to begin setting. They promptly ignored ponies that stared at them, well he tried to at least.

Eventually they made it to a cafe with outdoor tables. He saw it when she gave him the tour. It looked like a neat little place. It didn’t look to busy right now, with only one outdoor table occupied.

They took a outdoor table for two and James waved over a waitress. He was so nervous. This was such a bad idea. He hoped Sweetie remembered their story, “Hello I’m Daisy Bud and I’ll be your waiter. How may I help you tonight?” She looked between them both setting down some menus, her eyes lingered on the sight that was Sweetie. He couldn’t blame the mare. Sweetie looked something alright.

“You can start by getting us some water while we look at the menu please,” James said.

“Ofcourse,” she replied getting one last look at Sweetie before going elsewhere.

“...So what do you think you’ll be having?” James asked Sweetie as they both looked over their respective menus.

“I’m thinking the rose salad,” Sweetie answered looking at her own menu.

“Good choice. You know I’ve made those but can’t really eat them, sure I’ve tasted them but rose just doesn’t taste good to me, probable because I’d get sick if I tried to eat too much of it,” James said, “but I’m told those are really good. As for me I think I’ll have a pecan salad.”

“Why would you get sick if you ate roses?” She asked.

“Well I’m human, although I can eat a lot of different things, flowers usually isn’t one of them.”

“Oh,” she said thoughtfully.

Daisy returned with their glasses of water and asked what they wanted, “I’ll have the rose salad!” Sweetie answered then battered her eyes at him as he went to grab his drink, “and my date will have the pecan salad.”

“Your date huh?” Daisy asked looking to James in some way.

“Yep, he’s taking me out on a romantic date!” Sweetie answered with a smile.

He didn’t expect Sweetie to be so forward. He froze in spot with his drink halfway to him. He went ahead and drank some and put it down,, “I-I c-can explain-” She just looked at him. His throat was so dry. He got another drink of water, “i-it was a card game if I won she’d clean up her room, if I lost she’d have me do ‘something’,” he said using his fingers to make air quotes, “I thought she’d have me clean up her room, instead here we are.”

She looked at him for a moment, “So, that was a pecan salad and a rose salad?” He nodded, “one moment,” the way she said that was foreboding.

A moment later a stallion and a mare walked up to their table from inside the building, “sir,” the stallion of them said pointing to James, “I’m going to have to ask you to come with me.”

“Um,” he coughed, “what for?” James asked.

“Yeah, we’re trying to have a date!” Sweetie complained.

James felt like he was caught already. He needed to calm down and pray to god that Sweetie remembered the story. He held up his hand, “it’s okay Sweetie,” he said getting up, “lead the way,” he said gesturing for the stallion to go.

The stallion headed into the cafe and into the back. James followed and got one last look at his date. The mare was talking to Sweetie. He couldn’t help but feel this entire restaurant was a den of undercover cops or something. He really hoped Sweetie remembered the story.

He found himself in a somewhat cramped office sitting down and facing the stallion, “so what’s this about?”

“Imagine my surprise when one of my waiters comes to me talking about some stallion dating some filly,” the stallion said.

“I imagine it’s very surprising, considering your near immediate reaction.” James said figuring it’d be best to let him lead the conversation.

“Yes,” the stallion sighed, “well, I’d like to know why your dating a filly?”

“Um, well like I told umm, Daisy was her name?” the stallion smiled and nodded, “yeah like I told her I lost a card game in an effort to get her to clean her room. I thought she’d have me clean her room, instead she wanted to go on a date with me I guess, and before you ask yes she did clean her room.”

“Which card game?”

“Go fish.”

“So just a one time date then?”

“Of course, though I don’t think she knows that yet.”

“Good lad. You can do better. Now get out of my office.”

“Umm, what?” James asked, “okay then…” he said getting up, “Later.”

He left and went back to Sweetie who was yelling something at the mare. He missed what Sweetie yelled but the mare gave him a smile as she left. He sat down in his seat, “what was that about?”

Sweetie just huffed and crossed her legs, “nothing.”

He really hoped it was nothing. He had no doubt they were back there confirming if both them told the same story. The suspense was killing him. He really wanted to ask Sweetie what she told the mare, but knew better. He’d just have to wait until they either sick the guard on him or believe their story.

After what seemed like forever to him Daisy finally showed up with a genuine smile, “Sorry for the inconvenience, here’s some rolls as a apology. Did either of you want to change your order?”

“No, I think we’re good,” James replied. He felt so much relief. It either means they fell for it and Sweetie stuck with the plan, or they’re just stalling till the guard gets here. Either way, he felt a strong need to sell the idea that this was a one time date to any observers.

“Hey, this is a date! You should’ve asked me if I wanted to change my order,” Sweetie complained. It was hard to take her seriously looking like that.

“I hope you understand this never truly could be a real date Sweetie, but you’re right. I did lose the game,” he got a sip of water, “did you want to change your order?” she nodded no. “Well, you look beautiful, and I’m lucky to be going out on a date with a filly like you,” he droned in the most monotone voice he could muster.

Sweetie blushed, “really?” she questioned with a high pitch. Daisy looked at James with pity and was clearly resisting the urge to laugh, “I-I mean that’s more like it.”

James sighed again, “yeah yeah, let's get this wonderful evening over with,” he leaned over to Daisy and whispered, “could you please get our food fast, this is embarrassing.”

“What was that?” Sweetie asked suspiciously.

“Oh, um. Just making sure you get the best rose salad you’ve ever had,” James said defensively as Daisy covered up a chuckle as a cough.

“Aww, that’s so sweet,” Sweetie replied as the mare left.

“So Sweetie you like reading?” James asked, he felt fairly confident they believed their story. He saw no reason for them to not send in the local authorities right away. He just had to keep up the act. He took a good drink of his water.

“Yeah, there’s lots of interesting things to read about.”

He let out a half insane chuckle, “In this freaking world I have no doubt about that. How were we able to eat out after a small army of crab ponies invaded this town? It had not even been ten minutes since they left and everypony in town was acting like nothing had happened!” He ranted.

“It’s Ponyville.” various ponies replied back. The other tables where less empty now. He wondered how he missed them filling up.

He wasn’t sure if he wanted to know why everypony around him seemed to answer him unanimously. It either meant he’d be almost dying on a far to often bases, or ponies here just really knew how to handle things. Probable both, “right, sorry everyone,” he apologized looking around.

“I thought you were very brave to fight those crab ponies,” Sweetie said drawing his attention.

He rubbed his face and sighed, “Thank you Sweetie, but could we please talk about something else, I really really don’t want to think about that, it...” he took a quick sip of his water, “So what kinds of things do you like to read?”

“Umm, just about anything.” Sweetie answered, “I just like reading.”

“Oh, well that’s nice. I was never much of a reader myself.”

“So um,” she said shyly, “how did you become a Royal Foalsitter?”

“I,” his voice cracked, he coughed it out then he took a sip of water. He was constantly on alarm mode, how could he not be, “ahem. Well you see Celest- I mean Princess Celestia tried to get me a monthly stipend.”

“What’s that?”

“Err, you can think of it like an allowance except I didn’t have to do any chores for it,” he said with a shrug.

"Why would she do that for you?"

“You'd have to ask her. Anyways, the nobles wouldn’t have any of it and continuously rejected her attempts.”

“They did? But isn’t she the princess can’t she do what she wants?”

“Yes she is a princess and you’d think so but no. She needs approval from other ponies to get somethings done. I asked her to stop trying and that I’d just find a job. The next day she set up a meeting and proposed to anoint me as a Royal Foalsitter. I’ll admit you ponies are so cute the idea didn’t seem bad at all at the time. So I took it.”

“That’s it?”

“Well, not entirely. I was properly trained in the methods of a Royal Foalsitter. That was a harsh week let me tell you. You don’t want to know what pegasi foals are capable of without diapers.”

“What do you-” Sweetie began before staring off into the distance, “Ewww,” she yelled.

“Hey! Some ponies are trying to eat here!”

He looked around and in fact other ponies were eating their food, many of which he was pretty sure showed up a little after they ordered then again he supposes he did have those free rolls for a reason, “Um, right. Sorry everypony, again.” He found their waiter and raised his hand to draw her attention, “Is our food almost done?” he asked once she made it to them, “also could you please refill my water?”

The mare leaned up to him and whispered “one moment, please.” He thought it was odd but ignored it.

A moment later she returned with a pitcher of ice water and refilled his glass. “It just got done. I’ll go get it now,” she whispered to him again ending with a giggle.

“Okay, the food should be here any moment Sweetie,” he said rubbing his hands together trying to ignore the weird waiter as Sweetie looked at him oddly.

The mare returned a moment later and set down their salads, “Sorry for the wait, bon appetit.”

“Um, sure… they do look good. I guess,” he took a drink of water, “thanks.” He said before she left.

He took a bite, “-so where were we? Oh yeah, to make a long story short the nobles basically got into bidding wars over my services because I was The Royal Foalsitter. It was very profitable. In fact, I moved to ponyville so I could retire early.” He praised Celestia for her quick response to the nobles refusals to give him a monthly stipend. Celestia never admitted it but she must’ve known the nobles were going to basically throw money his way. They seemed sadly predictable.

“Retired? I thought that was for really old ponies?” Sweetie asked then continued eating her food.

“Not necessarily, it’s for whoever has enough bits to sustain their lifestyle up until the day they-” He stopped himself, “umm, no longer need any bits.”

“-Oh. Okay, but then why’re you wa-watching over me if you’re retired?”

“Your sister convinced me to help her out and I wasn’t really in a rush to get back home and start unpacking my things.” He answered.

“Oh,” she said sadly looking down and playing with her food. He noticed lipstick on her water cup.

“How’s your meal so far?” Daisy asked suddenly, startling James a little.

“Good,” he answered.

“Can I get either of you anything?” She asked, they nodded no and she left.

“So Sweetie, are all your friends on vacation or something?” Sweetie’s ears drooped and she said something very quietly, “what was that?”

“I said, I don’t have any friends.” She looked so sad, as she idly ate her food.

“Oh, well that- we can talk about it later, this is supposed to be a date,” he rubbed the back of his head, “I guess. So let's talk about something different... besides reading what do you like to do?”

“I like to sing,” she answered with a little bit enthusiasm.

“Do you now? Are you good at singing?”

“Rarity says I have a voice of an angel pony,” she answered a little more happily.

“Well now you got me interested, you must be really good.”

Sweetie blushed, “I don’t know.”

“Oh don’t be like that, I’m sure you’re a wonderful singer.”

She just looked away shyly, which was somehow a little bit disturbing with the makeup on. Daisy came to their table, “Could I interest either of you in desert?”

He looked at their plates and found little of their meals was left, “Sweetie you want any desert?”

She nodded no, “No. I guess you could get us the check please. I think we’re almost done.”

The waiter once again went up and whispered to him, “one moment sir,” then giggled and left. She was a creepy waiter.

“...Well, Sweetie it looks like the date is over now,” he said gesturing to waiter who was walking back with their bill.

“What!? It’s not over yet!” Sweetie complained, confusing him, as Daisy set the bill down, “it’s not true date until we kiss!”

He was shocked. Did she think because of, “Sweetie, No. I took you out to a restaurant, and we talked, that’s a-”

“NO!” Sweetie interrupted cutely, front hooves pounding the table as she stood on them, “It’s not a true date until we kiss!” Daisy covered her mouth as she gave a brief chuckle. “What’s so funny you-you hussy, I saw you whispering to him earlier. You trying to steal my stallion?” Daisy broke out laughing.

James felt like laughing to but more so in a way that would hide how nervous he was. Fortunately, his year of working with fillies and colts kicked in, “Sweetie apologise now!” He said sternly.

“What!? but she-”

“I don’t care if she’s laughing at you, don’t call anypony names unless you know they are what you call them. Now apologise.” The mare was trying to contain her laughter.

Sweetie growled and addressed the mare, “I’m sorry,” she grumbled then turned back to him, “there you happy? Now can we kiss?”

“Sweetie that’s not how dates work,” he held up a hand to preemptively stop her, “a date is meant to determine if two ponies can get along. If they find each others company enjoyable, they can kiss, but if they don’t, they find somepony else to date until they do find the one they want to kiss,” he explained, “do you understand?”

“B-But does that mean you don’t like me?” she said with a tear threatening to spill.

James honestly couldn’t tell if she was still playing the game or not. This certainly wasn’t part of any plan, “of course not Sweetie, it just means that sometimes you date somepony who you like but don’t necessarily want as your special somepony, or they don’t want to be your special somepony. Would you force somepony to do something they didn’t want to do?”

“I-no, but then why’re we on a date?”

James eyes widened at this golden opportunity, “Because,” he said rather loudly, “I lost the game and unwittingly agreed to do it, and it seemed harmless enough to me. I’m sorry if I hurt your feelings but that’s just how dating is sometimes. You can use this as a learning experience if anything.”

“S-So that’s it then?” Sweetie asked.

“Yes Sweetie it’s getting late and it’s almost time for bed,” He said paying the mare. He left the mare a low tip. He’d just realized she’d been messing with him. He was tempted to leave no tip but he’d rather not give her a reason get the guard, “Lets go,” he said to Sweetie in her cute dress.

Sweetie looked defeated, “Okay,” she said getting out of the chair and following.

They continued in silence for a little bit until the restaurant was long gone.

James was a nervous wreck. He found himself looking everywhere constantly. He couldn’t believe they actually pulled it off. He saw no ponies following them so far. He hoped Sweetie didn’t take his last couple words as truth. Sweetie was behind him with her head down, “Sweetie, I hope you know our conversation back there was for the game right?”

“It was?”

“Yes Sweetie,” he answered. Her eyes lit up and she smiled, as she ran up to his side, “but don’t think this is over just yet,” he said mischievously.

“what’s not?”

He picked her up and she squealed delightfully, he brought his mouth close to one of her cute ears, “our date," he whispered, "I still want to kiss, but not here, otherwise playing the game would’ve been pointless." He enjoyed the sight of her blushing through her makeup.

They made it back and he had to put her down, she gave a huff of disappointment. He unlocked the door and gave a quick look around everywhere. Upon spotting no ponies he held it open for her giving a slight bow. He followed behind closing then locking the door.

“So how about that kiss?” he asked as he sat down crossed legged.

She danced on her a legs a little nervous. He opened his arms to her and she timidly moved towards him. She got on her hind legs. He caught her forelegs with one arm while his other began to pat and rub at her withers. Her dress draped over his legs her tail wagged a little.

She puckered her lips and closed her eyes. He leaned in and gave her a kiss, but this time he didn’t leave. She began squirming a little and opened her eyes to find him staring at her. She blushed hotter and put some more pressure into her kiss. He did the same. Her lipstick kind of smelled like cherries.

Soon enough she disengaged and got some air, “can we-” she breathed, “can we do that again?”

He lifted her head up and brought her into another kiss. This time however he let his tongue explore her soft lips. They tasted like cherry lipstick which was kind of nice. She opened her mouth in a silent gasp and he used it to invade her mouth. He found her supple tongue and began coexing it to play with his. She seemed hesitant at first.

It wasn’t long after she began exploring his own mouth with her own tongue, “mmm,” she moaned hotly in his mouth. The things he wanted to do her right now. All he had to do was take off that dress.

He blinked and quickly left the kiss much to Sweeties disappointment.

He picked her up and set her down in front of her, “well Sweetie I could certainly do that all day. You’re a really good kisser,” he complimented causing her to blush, “but it’s getting late and I think we should stop before I- I mean I think there are somethings we need to talk about before things get too heated, and I do something I’ll regret.”

“Aww, but I liked kissing you, it-” she blushed, “made me feel all warm inside.”

He let out a suffering sigh for the fate of his right hand later tonight, “Jeez Sweetie. Way to make this hard on me. Now take a bath and brush your teeth. We’ll talk about stuff tomorrow.”

“Okay,” she said without complaint though she clearly wasn’t too happy about it.