Under "Her" Skirt

by Blobskin

Rating: mature
Tags: Human, Anthro, Romance, Drama, Original Character, Porn, My Little Pony: Friendship is Magic, Fetish, Sex
Length: 13968

A 4 cm tall human can't get enough of Vanilla's teasing skirts. Until he learns "she" is hiding a certain kink under there.

Chet is only 4 cm tall in a world of towering anthro ponies and Cadence thinks he's lonely. So she sets him up with a nice maid named Vanilla to take care of him. They get along really well, Chet finds her incredibly attractive, and he can't get enough of her teasing skirts. The relationship quickly heats up and one thing leads to another... and Chet learns this "mare" has one kink in particular that might destroy the relationship. One hiding right underneath that enticing skirt...

Contains: anthro ponies, micro human, M/m, trap, femboy, upskirt, cock and balls

Published 2022-04-24 23:20:01 UTC
Last updated 2022-11-03 23:25:25 UTC

Adult Conversations

Version: 3

"Chet Bowman, I know how to make you happy!" Princess Mi Amore Cadenza announced.

The human, Chet, stared in the anthropomorphic pony's direction. So did Twilight. They were in the middle of their daily Earth-Equuis discussion when the pink mare had burst into the conference room and simply... yelled.

"Uh," the human mumbled. "Thanks Princess Cadenza, I guess. But, um, I'm already happy?" The man wasn't sure what the proper response to this kind of intrusion was.

The pink pony almost floated as she made her way to the second couch that sat across from the one Twilight currently occupied. She then flopped into the cushions before leaning forward and looming over Chet. The tiny human was a little less than four centimeters tall and currently seated on a stack of bits on the table in the middle of the room. When they had been trying to make the man an appropriately sized chair he had suggested something more practical. A bit was wider around than most chairs back home to his small stature, but they could be stacked to any height, making them modular. So four or five bits gave Chet a chair about a centimeter high which was perfect for him. The surface was kind of hard, however Chet refused to complain.

"Don't lie to me Little Mister," Cadenza warned. Chet couldn't tell if the pony woman was being serious or playful.

"I am happy," he argued, gesturing to himself.

Twilight took off her glasses, uncrossed her legs, and set aside her clipboard. "Chet is unhappy?" she asked.

The Princess of Love pounced on the question. "Obviously Twilight. Haven't you noticed?"

Twilight looked shocked. "But we've been working so hard."

"It is unfortunate Twilight, but your best work isn't always enough," the older alicorn said with a sagely nod and a raised finger.

Chet groaned. The pony people often did this. Talk over him like he wasn't even there. "Excuse me, I think I am the only expert in the room who can say for certain whether 'Chet' is happy or not. And, according to my incredible insightful powers, he is."

Cadence turned on him in an instant. "Do you have a job?"

Chet blinked up at the mare. "No," he admitted.

"Are you going to school?"

Chet was confused. What was with the weird interrogation all of the sudden? "Twilight has been teaching me about the world."

"Do you have any hobbies or friends?" the alicorn continued.

"Twilight is my friend," Chet scoffed.

Twilight smiled a little at that, but Cadence didn't. Her expression actually seemed to harden. "What about hobbies? What do you do for fun?"

"Twilight finds me some nice books."

"Do you have a marefriend? A girl in your life?"

Chet felt like that was kind of personal. "No. What is this, a quiz about my life?"

Cadence was quiet for a moment. Then she gave her deadly serious conclusion. "Chet, you live in a cage. A cage you only leave to talk to Twilight and to read books. You are clearly miserable and you don't even know it."

"D-don't tell me how to live my life. It's fine." Chet's words were weak. It was embarrassing to have someone judge him like that.

Twilight's ears pinned and she raised a hand to her muzzle. "When you put it like that, I guess it is obvious. How could anypony be happy in those circumstances."

Cadence nodded solemnly. "Fortunately, I know the cure. And it is an easy one. Chet needs a marefriend."

Now the human blushed. "You are not about to set me up on a bunch of blind dates."

"No no no," the pink princess shook her head. "Your situation is far too special for such a chaotic method. Your mare will need to meet very specific qualifications."

Chet grumbled. "I meant I don't want you deciding who it is I... date. Look, if I wanted a girlfriend, I'd go out there and look. But I don't want a girlfriend. I'm fine with where things are right now. Okay? When the time comes for me to go dating, I'll be the one to decide... that stuff." Chet crossed his arms to give a sense of finality to his words.

Twilight sighed. "Chet, Cadence is the Princess of Love. She is an expert on emotions and relationships. You can trust that she knows what she's doing and can help you."

Chet faced Twilight, his closest friend in this world of giants. "I don't need her help because there isn't a problem here for her to solve."

"Really?" Cadenza challenged, crossing her own arms.

Chet was a bit intimidated. Hard not to be when a furry person that large semi-threatens you. "Yes. I'm fine."

Cadenza raised a brow. "You are happy? Completely? The fact that you'll never see your old friends, family, or lovers again hasn't affected you in the least?"

Chet winced. "I didn't say that."

"Do you really think just burying yourself in the history and culture of Equestria will be enough to escape the past you lost?"

Twilight's ears perked at that, but she didn't add anything.

Chet sighed quietly to himself. He felt defeated. Exposed in some way. Was that what he was really doing? "My old life is gone. I'm just trying to make a new one. To do that I need to know about this world, you know?"

Cadenza's eyes narrowed. "And what possibilities do you see for your new life so far?"

Chet bit his lip and eventually gave a helpless shrug. "I don't know."

When Cadence spoke again her voice was much softer. "Mr. Bowman, you are small and you are helpless. You cannot build a life for yourself. You will always be dependent on another from this world. That's why you feel so lost. You need a pony to take care of you. Until now your well-being has been guaranteed by the crown and by Twilight, but that help does not come with the kind of emotional support you really need. It's been six months Mr. Bowman, it's time to try a different approach. Please let me help you."

Chet looked at his feet. "I don't see how getting a girlfriend is supposed to... do anything." Was that even an argument?

Cadence snorted in amusement. "You'd be amazed what wounds of the heart can be healed by simply having another so close to you. A proper lover is very different from a friend."

Twilight rubbed her chin in thought at that. She had been studying the magic of friendship for some time, but Cadence had been studying the magic of love for even longer. She was intrigued.

Chet wasn't ready to surrender yet. "I don't want you forcing some girl on me."

"And I won't," the pink pony said firmly.

Chet glared at Cadenza for a moment. Then he deflated and scratched his neck. "What do you want from me?"

"I want you to accept a mare into your life. To develop a relationship that is deeper than the one you share with Twilight and especially the crown itself."

Chet was quiet for a long time as he stared at the floor. Well, the tabletop beneath his feet. Did Cadence have a point? Was he miserable? Would dating help? Sounded more like he should find a therapist. But he wasn't sad! Was he in denial? Using Twilight as a distraction from everything he'd lost since coming to Equestria? Now that Cadence was pointing it out, Chet wasn't sure he knew how to feel anymore. Maybe he really wasn't happy. He was NOT sad! No, he was just empty. Drained. Hollow. Chet didn't like this feeling. Had it always been there? He didn't want to feel this. He also didn't want to be one of those idiots who refused help simply to defend a meaningless pride.

Chet took a very deep breath. He looked up at Princess Cadence waiting patiently for his response. "Alright. We'll... try it your way."

Cadenza's face lit up with a bright grin and she clapped excitedly. "You won't regret this Mr. Bowman. I promise you'll be happier than ever before once my work is done!"

"Yeah yeah," Chet mumbled half-heartedly, "my life is going to change forever." Perhaps he could escape this by simply turning down every mare Cadence tried to hook him up with. "So what are you going to do?"

Cadence coughed into a fist and cleared her throat. "First I need to create your personality and preference profile."

Chet blinked up at the large equine woman. "What?"

The princess giggled. "I need to cast a spell on you to determine what kind of mare is right for you."

"Whoa whoa whoa," Chet objected quickly. "You are not about to go casting that on me. I don't want you reading my mind. That is private stuff."

Twilight chose then to play the guilt card. "Please Chet, trust Cadence. Her spell won't hurt you. It's just to scan you and she'll only use it to find you a compatible match."

Chet and Twilight stared at each other for a few seconds. Twilight had never led him astray and he liked her. He trusted Twilight and she was asking him to extend that trust to Cadence. "Fine..." the man eventually relented.

After a short pause Cadenza's horn began to glow blue and a matching glow surrounded Chet. He half-expected to feel something poking around his head, but the only sensation he got was a tingle over his skin like he'd run into a spider web. Next thing Chet knew it was over and the Princess of Love had her eyes closed and a look of complete focus. The man took that time to brush his arms and chest to get rid of the lingering feeling of being scanned. Meanwhile, Twilight watched Cadence as she... did something.

"So... are we done here?" Chet asked after a minute or two had past.

"Hm," Cadence muttered as she came out of her trance with a small jerk. "Oh, yes. The spell was a success. Now I just need to find a match. Don't worry little Bowman, it won't be long until you have a mate who you can pour out your heart to." With that the pink pony stood and left the room.

Chet wasn't sure what to make of the events that had just taken place. He'd been confronted, surrendered, and now coming soon he was going to have a date. It was all very abrupt and confusing. He turned to Twilight and merely shrugged.

She giggled at that. "Yes, today has been very... different. Where did we even leave off?"

"We're going to keep going like none of that just happened?"

"Do you want to stop for today?" Twilight asked with a tilt of her head.

Chet sighed. "I think I need to lay down. That was way too much... stuff."

Twilight smiled sympathetically. "Yes, I can imagine. Let's end early today."

The days came and went. Chet almost forgot the Princess of Love was off somewhere trying to find him a girlfriend. In the meantime he and Twilight continued to meet every day to share stories and explanations about their respective worlds. However, the tone of their discussions was darker. Neither of them was as lively as before. It could have been due to the revelations Cadence had exposed. Or it could have been that the two of them were running out of things to talk about. Honestly, Chet had gone over every ounce of human history he remembered, described what he understood about as many religions as he was capable of, and even begun defining various memes and slang terms. Despite how big and complicated a world is, there was a limit and Chet feared they might be getting close after so many months of endless sharing. What would they do when there was nothing left to say?

Then Princess Mi Amore Cadenza came bursting into the room in the middle of their latest discussion.

"She is here!" the pink pony woman announced. "I have found Chet a mare!"

Accompanying the alicorn was a short pony in a maid outfit. A black and white frilly dress complete with a little bow tie enclosed her cream colored fur. She had a golden mane that was tied back and she glanced shyly into the room from behind the taller and more energetic princess. Chet and the maid's eyes met.

Twilight sat up in her seat. "That's great news. It's only been two weeks."

Cadenza pranced into the room with the maid a few steps behind her. "Yes it was fortunate that one of the castle staff turned out to be almost a perfect match!"

"Almost perfect?" Chet repeated.

"Don't be so quick to judge," Cadenza scolded him. "Vanilla Wipe is nervous enough about this meeting. You should be nice."

Chet opened his mouth to refute her in some way but hesitated. He didn't want to hurt this random mare's feelings. "I'll try to be nice, but I'm still not sure about this whole thing."

"That's why she's here!" Cadenza gushed. "To introduce you two." The alicorn grabbed the poor mare's arm and pulled her in front of the second couch where she pushed her down into the seat.

The maid was quick to tuck in her skirt and squeeze her knees together, obviously not wanting little Chet on the center table to see her panties. That would have been extremely awkward. Though the almost peek convinced the man to give the mare a once over. Her uniform didn't come with a hat or gloves, but she did have long sleeves and a pair of tall white stockings that extended to just above her knees. Additionally, Chet couldn't help noticing that the mare had no breasts. She was flat as a board. However, while the puffy skirt made it difficult to be sure, she may have made up for it by having a fair amount of bubble butt.

Chet didn't want to admit it, but he thought she was cute.

"Now Chet," Cadence began, "this here is Vanilla Wipe. She works in the castle as a maid. Vanilla Wipe, this is the stallion I was telling you about. His name is Chet and he's nervous about this arrangement too. He just has a more aggressive way of expressing it."

"Hey!" Chet protested. "I'm not nervous. It's just that I don't want to do this." He immediately regretted saying that. The maid's ears pinned. He had already hurt her feelings.

"Chet," Cadenza said harshly, making the man flinch. "I believe you agreed to at least give this a chance."

The human sighed and rubbed his neck as he stalled for time. "I... guess I did. It's just weird."

"Because you are making it weird," Cadence stated simply. "All you have to do is talk to each other. Believe me, the two of you will be dating before the day is over."

There was a moment of silence as the potential couple eyed each other and the room's other inhabitants. There was an awkward shuffle as the two tried to get more comfortable. Then an agreement between them was reached without the need for words. Though it was Vanilla who found the courage to say it aloud.

"Excuse me Princess--err--princesses," she corrected. "Can me and Chet... have some time... alone? Please?"

Cadence and Twilight blinked. Then they giggled while excusing themselves from the room and tossing out cliché advice. Then it was just the two of them. Vanilla Wipe, a small mare in a maid uniform. Chet Bowman, a human who was shorter than a pony's thumb. Neither of them spoke for a while. Then Chet couldn't stand it anymore. He stood from the stack of bits he used as a seat and cleared his throat.

"So... Princess Cadence told you about me?"

Vanilla nodded shyly. "Yes. She warned me about your... height. So I knew you weren't a... normal stallion before I agreed to this."

"So she, like, interviewed you?"

"Yes."

"What do you think?" Chet asked while holding out his arms for her to inspect.

Vanilla leaned forward and ran her eyes over his tiny body. "You're cute."

Chet's arms fell back to his sides. "You... really want to try... this?"

Vanilla tilted her head. "You don't?"

Chet bit his lip. "You're actually interested in being with someone... like me?"

The mare frowned in disappointment and brushed at her skirt, smoothing the wrinkles. "You don't want to even try?"

Chet shook his head. "It's not that I don't want to, it's that I don't... see how."

Vanilla looked confused. "We talk, get to know each other, then spend time together. Seems pretty straight forward."

Chet laughed. "Yeah, if we just wanted to be friends. But we're supposed to be... lovers."

"Yes," Vanilla nodded, still unsure where he was going. "That's what Princess Cadenza was hoping for."

Chet realized the mare didn't get what he was vaguely referring to. He'd have to be far less subtle. The man started to pace on the table while massaging his head. "How do I say this?"

"Say what?"

Chet stopped and turned to the mare. He clapped his hands once and gestured to her. "You are an adult, right?"

Vanilla raised a brow. "Yes."

Chet nodded uncomfortably. "So, let's have a real adult conversation. No beating around the bush. No games. No dodging the truth."

Vanilla sat straighter, while also discretely tugging the hem of her skirt which had pulled upward with the motion. "I can do that."

"What is the goal of lovers? The ultimate point of dating?"

Vanilla looked up in thought for a moment. "Happiness?"

Chet snorted. "You got that from Cadence. And no. The goal of lovers is... sex."

Vanilla blushed, but didn't say anything to that.

"The point of dating and all that is ultimately sex. The stick in the hole dance. It is the final expression of love. Now tell me, how are we supposed to do that?" Chet punctuated his question by holding out his arms again and pointing to himself.

Vanilla winced. "I... I'm not sure I should say it."

Chet sighed, dropping his arms once more. "I know what you're thinking. I considered it myself. The only way I could... have sex... in this world is if I went cave diving." Chet paused for a moment then added a bit more darkly, "you'd have to shove me up your vagina."

Vanilla's blush returned even brighter than before and she squirmed in her seat. "Yes, that's what... I was thinking too."

"It's okay," Chet reassured her. "I'm not grossed out or anything. It's just... I don't know if I want to do that and I'm sure you don't want to do that either."

Vanilla continued to squirm. "Actually..."

Chet's mouth hung open. "Wait, you want to..."

Vanilla cleared her throat and gripped the fabric covering her thighs. "Cadence asked me about... that sort of thing. So I've been thinking about it and... I'm... okay with it. If you are."

Chet stared. For a while neither of them had anything to say. They simply sat there. Then the man spoke up.

"Alright. I think what we need to do is decide what we each want -- expect -- from this relationship. Does that sound like a good idea?"

Vanilla hummed agreement. "I once heard somepony say that the key to a strong relationship is good communication."

Chet nodded. "Right. So I guess I'll start." Chet took a few seconds to organize his thoughts. "I don't want to be treated like a pet. I don't want to be babied or for you to act like I'm super delicate. I want... to be included in things. I don't want you to be afraid of hurting me. I also want to know... that I'm enough."

"Enough?" Vanilla couldn't help it. The phrase confused her.

Chet swallowed. "Vanilla. I'm small. I... can't hug you. I can't pet you. I can't even properly kiss you. I'm... small. I'm going to be little more than... your living sex toy. I... I guess I just don't want you to see me like that. I... I'm afraid that I won't be seen as a proper boyfriend. Or husband I guess. I don't want you to get bored with me and start seeing other men. I don't want you to cheat on me!"

Vanilla was clearly surprised. "I would never."

The man cleared his throat and turned away from her, embarrassed by his own outburst. "So my... conditions aren't a problem for you?"

The mare slumped in her seat a bit and brushed the surface of her dress. "I have no complaints. You want me to love you as a stallion, not to be afraid of hurting you, to include you in activities, and to be loyal. Is that right?" At his nod she continued. "I accept."

"What about you? What do you want from this relationship?" Chet asked quickly.

"Me?" Vanilla tensed, gripping her skirt a little tighter than before and pressing her knees together a little harder.

"Yeah," Chet said. "What do you want from me?"

The maid wrinkled her face in thought as her eyes bore into the backs of her hands in her lap. "What do I want?"

Chet waited, feeling somewhat better about where this was going. Though he was also anxious. What was Vanilla going to demand?

After a minute of being quiet she spoke. "I always wanted a stallion who was smaller than me." She glanced at Chet and smiled. "I've always wanted a stallion I could tease and... dominate. A little man who would let me get away with constantly pointing out how I was bigger than them. Though I never thought I'd find a boy shorter than me," she admitted. "But most importantly," she went on, suddenly serious, "I want a man who is open to experimentation."

"What do you mean by 'experimentation'?"

"I..." Vanilla grew bashful and curled into herself. "I have a lot of... kinks. I want a stallion who is willing to... try... lots of things." Her eyes latched onto Chet with a hopeful twinkle.

Chet made a silent "oh" as understanding hit him. He could be Vanilla's perfect match. He was smaller than her, it would be easy for her to "dominate" him -- whatever that meant exactly -- and among her kinks must have been something about using her partner as a sex toy. Chet was a dream come true.

The human felt himself sweating under the intensity of her gaze. He wiped his forehead. "I'm not sure about those," he admitted. The life immediately began to drain from Vanilla's face. "But that's just because I don't understand!" he said quickly. "I'm not sure how to feel about you wanting to tease me and I don't know what you mean by 'dominating' me."

Vanilla regained some of her optimism at his wish for clarification and was eager to explain. "I just want to... loom over you. To have you always looking up at me. I want to feel... powerful. Like I'm big. Your entire world." She was blushing again. "And I just want to joke about your height a little bit. Is that too much?"

Chet chuckled at her desires. "No that's alright I guess. We'll just have to see what you've got. As to looming over me... sure. Why not?" Vanilla began to smile with relief. "But about the kinks thing..." Vanilla frowned. "I don't know. What kind of... what kind of things did you want to try?"

Vanilla began to fidget. Her fingers played with the edges of her skirt and she couldn't force herself to look at the man on the table. "Well, other than shoving you in my pussy, what about... my butt?"

Chet wiped some sweat off his brow. This was getting a little hotter than he expected for a first meeting. "I... guess I'm okay with that."

"Using you as a sponge in the bath?" Vanilla continued with a bit more confidence.

Chet rolled his eyes. "As long as you don't drown me."

"Sucking on you?" she asked with a smile.

"I was kind of hoping you would," Chet replied with a bit of sass.

Vanilla responded by clasping her hands together in front of her and getting slightly excited. "And having you massage my hooves?"

Chet waved his hands as though trying to hold back some of her overflowing energy. "Whoa there, I guess I'm a little more open than I thought."

Vanilla giggled as she sat back and relaxed. "I hope so. I've got a lot of ideas how to play with you."

Chet actually laughed. "So, getting back to the point, what did you want in this relationship again?"

It took the maid a moment to remember what she had said originally. "I want a stallion who is smaller than me, who I can tease and dominate, and who is open to lots of kinks."

"I accept," Chet announced with a nod.

Vanilla practically melted into the couch. Chet fell back onto the pile of bits. That was intense. Chet felt like they had both accomplished something today. Had they actually agreed to be lovers? He didn't even know her!

Chet coughed loudly, causing Vanilla's ears to perk. "We uh... need to schedule a first date."

The mare looked confused for a second before her eyes widened in panic. "Oh my gosh, you're right! We don't know anything about each other! We've got to go someplace to eat and share all our silly stories and hobbies. All we did was agree to... what did we even just do?"

Chet shrugged. "I don't know. Maybe we skipped a step. So I guess we need to back up and start over?"

Vanilla smoothed the crinkles in her skirt for a moment. "No, not start over. I think that was a good place to begin. Now that we have the finale figured out we just need to get there. This is going to be a weird relationship huh?"

The two of them giggled.

"I'm not sure it ever had a chance of being normal," Chet thought aloud.

Author's Note

I wonder how many people will ignore or somehow miss the "subtle warnings" about what's coming. I'd prefer if people simply left their downvote as soon as they're done reading the description and got on with their lives rather than following the story, getting intrigued and interested, then slapped in the face with the "surprise". I do not want to read those stupid whiny complaints. Though I have considered writing a second alternate ending where the "surprise" doesn't happen and everything is as it appears. Though that would kind of ruin the drama and suspense of the reveal that is intended. But I've got to consider that some people are just here for the sex anyway.

Lastly, I have absolutely no idea how to pronounce Chet. It came up when using a random name generator and I was like "that's good enough". Couldn't use Anon for a serious story like this after all.

Grinding Gears

Version: 2

Of all the things they talked about they missed the most crucial detail.

How Chet was going to get to their date.

The tiny man could only blush in embarrassment at their... his oversight as a castle guard carried him.

It wasn't unusual. The hand of a guard was his typical form of transportation. To his meetings with Twilight, if he wanted another tour of the castle, whenever he felt the need to visit the library, whatever. Chet had even been assigned his own guard rotation. He had four guards who changed out every six hours. Why not three guards every eight hours he wasn't sure, but he assumed Celestia knew what she was doing when she made the arrangement. This guard was named... Something Cry. To be fair, they were a very professional bunch who took the job super seriously. Probably why Chet felt so comfortable being carried by them. It was easy to forget they were even there. That they were really people and not merely part of the background or a vehicle.

Chet and Vanilla's date was going to be a simple thing. Just lunch at a private table in the cafeteria. Couldn't get much more plain than that. Though the man was flustered that he had to show up with a guard escort, he also felt a bit special. How many others had a bodyguard with them just to go to the lunchroom?

Silly thoughts were about the only way he could keep a lid on how nervous he was. And the fact Chet was nervous made him even more nervous. It was proof he actually wanted this date to go well. What did that mean? All this time blowing off the very idea of ever being in a relationship again and yet he suddenly latched onto the first chance at one he was offered? It was strange. Suspicious even. Was Cadenza's understanding of people that accurate? Was her magic that strong? Twilight had explained how Celestia could move the sun, Luna could move the moon, and described many of the amazing things she herself had done. It always left Chet thinking Cadenza was the weakest Princess. After all, she was the Princess of Feelings.

Chet was starting to reconsider the abilities of the pink alicorn now that he was experiencing them himself.

The human rubbed his temple as his escort approached the doors of the cafeteria. The constant clicking of armor and hooves on the tile floor below made for great white noise as his mind worked. Chet's transport stopped in front of the entrance and used his free hand to push the barrier aside. The man felt a small shiver go up his spine. There were a lot of ponies here. Granted, it was a large room and it was far from packed, it was still more ponies than the human was used to being around. His eyes took in the various occupants as his guard moved him to a secluded corner. There were soldiers who had ditched their helmets and breast plates gathered at one of the larger tables chatting loudly and gesturing wildly. There were servants still in their uniforms at another table quietly enjoying their meals while engaged in polite conversation. And there were a few ponies wearing suits casually debating something or other. What really struck Chet though was the style of the lunchroom itself. It was like a restaurant but with far more tables and booths.

This was the cafeteria? Chet had never been here before. There had never been a reason for him to come here. Now he was intimidated. How could he have a good time with Vanilla if he was constantly eyeing the room's other towering inhabitants? The man was already predicting a disaster.

Cry carried him to a booth farthest from anyone else and gently lowered his hand to the table. Chet had made sure to come a bit early for no particular reason other than to avoid some possible delay. Like if he and his escort had randomly run into Twilight on the way here and stopped to gossip for a moment. By coming a bit early they would have had the time to deal with that and anything else that might have come up. Was he being overly paranoid? As Chet stepped off the giant hand he groaned in frustration and smoothed the wrinkles in his plain clothes.

"Something wrong?" Cry asked, his voice gruff.

"Huh?!" Chet yelped in surprise and looked back over his shoulder. "Oh. No. Just... I'm thinking too much."

The stallion lifted his hand away and stood tall. Cry was a unicorn with gray fur and he sure struck an intimidating figure in that golden plate. Doubly so being the only guard in the room still fully armored and with his arms crossed behind his back. "You want some advice?"

Chet sighed. He must have looked pretty worried if even his stoic escort was trying to help. They never spoke unless he said something first. "Please."

"Relax."

Chet blinked. "That's it?"

Cry nodded once. "That's it. This is not a test, there are no right answers. You came here to have a good time. So have fun."

Chet was quiet for a moment. Then he chuckled. "That's actually some pretty good advice."

Cry smiled and puffed out his chest. "Glad I could help."

Chet stayed where he was as the armored pony moved to the side to guard the table. Then the human regarded the surface he was on. He hummed in thought. What could he use as a seat? The napkins might work, but he would need quite the stack and he didn't want to waste them. A piece of silverware? Not nearly thick enough. Chet strolled across the table towards the wall where there was a bottle of ketchup and a bottle of mustard. He scratched his head. Should have brought some bits. That always worked. Chet was starting to feel very unprepared. Hadn't figured out transportation and now he hadn't thought about seating. What else had he overlooked?

Shrugging helplessly, Chet simply sat on the table. He could have tried striking up a conversation with Cry, but Chet wasn't sure what to talk to him about. Chet had been on dates before so he had some experience to pull from. Back home. When he was in the same height category as his date. How was this going to work? The human covered his face anxiously. He had to relax. He was asking too many questions. Relax. Just go with the flow. As Twilight had said, all he had to do was trust Cadenza's matchmaking powers. So he watched the activity in the room and waited for Vanilla. It was a frustratingly boring few minutes.

Vanilla snuck into the room like a mouse. Chet had to hold back a snort of laughter at the sight. She was wearing a hot pink blouse and an azure blue pleated skirt. The mare was practically a glowing beacon for attention. The bizarre clash of outfit and behavior eased some of the tension in his mind greatly. At least he wasn't the only one nervous about this date.

It took Vanilla only an instant to spot Cry in his armor across the room. At that she froze for a moment, seemingly afraid to approach. When she did it was with hunched shoulders and a lowered head. Like she was trying to appear small and nonthreatening. Now Chet was starting to feel like a jerk for finding her fear amusing. The mare navigated the simple obstacle course that was the cafeteria and paused in front of the armored stallion. With the two of them standing right there Chet finally realized just how short the mare was. Cry might have been a hair above average height, yet he was at least two heads taller than Vanilla. Perhaps more.

"Miss," Cry said as a form of greeting.

"Sir," Vanilla replied, struggling to make eye contact.

Chet was tempted to hurry along the awkward silence that followed.

"I'll be leaving him in your care. It is your job to keep him safe now. Understood?" The stallion was serious. As usual.

Vanilla nodded. "Of course, sir. I won't let anything happen to him."

"Good. I'll be waiting outside until you two are done. Enjoy your date." Vanilla was left blushing at his words as Cry made his way for the door and disappeared.

Chet briefly wondered why Cry didn't go spend time with the other guards here in the lunchroom, but his thoughts were quickly pulled away as Vanilla made those last two steps that put her in front of the table. Her skirt hung below the table's edge, but the various overlapping cuts of fabric waved teasingly. The human was momentarily hypnotized. Then Vanilla snapped him out of it.

The mare hummed thoughtfully before greeting him with a single word. "Hi."

Chet responded in kind. "Hi."

"May I have this seat?" she asked while pointing at one side of the booth. Good, she hadn't noticed him staring.

Chet rolled his eyes dramatically. "Make yourself comfortable. I haven't been waiting long."

Vanilla stepped to the side and moved to slip into the seat. She bent forward and her skirt fluttered. The table wobbled under Chet, but he barely noticed. Finally the pale mare was planted on the padded bench. She took a second to fix her clothes and folded her hands on the table opposite where Chet sat.

"I'm not late, am I?" Vanilla asked with a hint of worry.

"Oh no," Chet assured her. "Me and Cry just got here early. I've never been in the lunchroom before is all."

The mare tilted her head in obvious curiosity. "Why not?"

"The danger, I guess."

"Danger?" Vanilla glanced around the room.

Chet snorted. "Vanilla," her eyes snapped back to him, "I'm small and this is a busy place. It would be easy for there to be an accident."

"Oh," her ears dropped. "Maybe we shouldn't have come here then."

"Nah," the man waved a hand dismissively. "Twilight and the guards are always overly worried about me. Going the extra mile to make sure I'm safe and all."

"Somepony has to," she asserted. "You're not scared of... something happening?"

Chet bit his lip as he hesitated to respond. "I... was at first. Like, really scared. You're all so... big. But I have yet to meet a pony who wanted to hurt me. When every giant you encounter is obsessed with making you comfortable and feel safe, it doesn't take long to forget fear." He paused after his explanation for a moment before laughing. "Wow, that sounded pretty deep."

Vanilla chuckled with him. "Yes it did."

They lapsed into silence after that. The mare played with her fingers while he shifted his legs so they wouldn't fall asleep. This was the worst part of any date: actually starting a conversation. Chet found his mind scrambling for a topic. Of course! This was strike three. He should have considered this too. Once they got something going they'd be fine, but he had had a whole day to plan for this. Maybe he should just ask her to get them something to eat. He could come up with something while they ate and maybe some of the stress would be eased with a full belly.

"What was it like?" Vanilla asked suddenly.

"What like?"

"Coming here, to our world?"

Chet scratched his neck. "Confusing."

"What happened? Or is it, like, a government secret?"

Chet snorted. "It's no secret. At least, no one told me to keep my mouth shut," he said with a shrug. "I can try explaining it to you, but it's a bit complicated and I don't really understand it all myself."

"Please do," Vanilla pressed, leaning forward with interest. "There's been a lot of gossip about you since that day. But it's all over the place."

He shrugged again. "Alright, I'll try. Twilight told me that all realities exist in these massive bubbles and float around in this huge place called the Void. Like a bubble bath, these spheres drift and occasionally bump into each other. Normally these bubbles are just supposed to bounce off each other because each world is surrounded by a powerful barrier, a wall that keeps everything inside. But sometimes when these worlds smack into each other their walls can fuse together for a moment, causing worlds to be connected."

"Wow," Vanilla mumbled. She was clearly mesmerized by his sad description. "So our world and yours fused together?"

Chet nodded. "Only for a moment. Only long enough for a small exchange of stuff."

The mare blinked. "You came to our world, do you mean somepony was taken to yours?"

"I hope not!" Chet gushed. "That would have been insane. I can only imagine the chaos if a random giant pony just appeared somewhere. Can you imagine if a pony the size of a skyscraper just dropped into Canterlot?"

Vanilla put a hand to her muzzle and held back a laugh. "Yes, that would have been bad."

"I'm pretty sure the exchange was just some grass from Equus going to Earth while me and part of the hotel where I worked came to yours."

Her ears shot up. "Part of the hotel? What? I never heard anything about this. Weren't you the only thing that came through?"

Chet shook his head. "It was me and a little bit of the building I was in. And it was a weird experience, I can tell you that. I had just put some paperwork away in the office and was going back to the front desk when there was this crackling sound. Like electricity going nuts. Then everything shook and the lights went out. There was this sense of being stretched, like someone was pulling on my arms and legs. Then... I was in Equestria. Well, I was in the ruins of a part of the hotel. Outside that was this field of grass where every blade was as tall and thick as I was. That freaked me out. I hid there until Twilight came to investigate and found me."

Vanilla didn't say anything for a moment. She just stared at her hands on the table. "That must have been scary."

Chet cleared his throat uncomfortably. "It was. But Twilight said I was impossibly lucky. The exchange could have taken place literally anywhere in the entire universe. I could have ended up on the moon or somewhere out in deep space. Showing up in an empty field? Very lucky. Impossibly lucky."

"But... you were taken from everything," the mare pointed out somberly. "Can you ever go home?"

Chet licked his lips. "The same impossible circumstances that got me here would have to be repeated. Though talented mages like Twilight can sense when and where the world touches happen, there is no way to reach them before they're over. They only last a fraction of a second. Then the two worlds separate. So... I'm never going home."

She stared at him. "That's very sad."

The man chuckled darkly. "I guess. I would have liked to say goodbye at least. Maybe patch up some of the messes I made too."

"What do you mean?" Vanilla urged.

"Eh," Chet rubbed his head. "I know it's cliche, but I was a lot like other people. I'd done a pretty good job of screwing up my life. My relationship with my dad was... gone. Mom at least kept in touch, if only barely. Most of my friends from high school had moved on. So I was basically alone in the world. Just me and the hotel. I guess the only dream I had by the end was that I could impress my boss enough that he'd put me in charge when he retired. I wonder what happened when giant grass suddenly replaced the main lobby." Though Chet had intended that last bit to be a joke, to lighten the mood, Vanilla didn't laugh.

"You and your dad," she began seriously, "what happened?"

This date was a disaster. What had Twilight's big advice been? What had Cry just told him a second ago? Have fun. Keep the conversation positive. Try to talk about happy things.

Yet what were they doing? Talking about how terrible Chet's situation before and after being ripped from his world was. However, Chet lacked the charisma needed to make a fluent transition off the current dark path they were on. He wasn't sure what to do but go with the flow and hope the conversation turned more cheerful soon. Very soon.

"My dad... just had bigger plans for me," the man sighed. "He wanted me to be better than he was. He wanted me to graduate from high school with honors, go to an expensive university, then get a well-paying job and become someone important. But I failed at step one. I never made it through high school. I just... couldn't understand the lessons. I... was too stupid for school."

Vanilla opened her mouth to say something, but stopped. She closed her mouth with a click. She looked down at her lap. Her fingers tightened into fists. "Did your dad... get mad?"

Chet sighed again. "Well... sort of. He wasn't the kind of man to yell or anything. It was just the constant look of... disappointment. Every time I came home with another low score he'd give me this look. He'd ask me why I wasn't taking school seriously and why I wasn't trying harder. He kept pushing me. It was me who yelled at him. I kept trying to tell him... something. I don't know," Chet grumbled and threw his hands up in frustration. "I was an only child. My mom had suffered complications during her second pregnancy and that was the end of the family plans. I was the only child they were ever going to get. So dad dumped all his expectations on me. Then I had to go and ruin that by getting interested in the hotel."

"What's so interesting about a hotel?" Vanilla queried with a confused squint.

"There was this hotel in town, an old family run place, but the kids didn't want to take it over for their old man. So there was just this one grandfather, a friend of my dad's, left to keep it going. A few times my dad took me with him there when he wanted to chat with Arthur. Arthur was the guy who owned the hotel. I remember running down the hallways while they just... talked. It was a fun place. When I got a little older I'd take my bike their and help the old guy out. With permission from my dad I kind of became Arthur's assistant. I'd help him clean rooms, I changed light-bulbs, I even helped paint the outside when it started to fade too much. It... became more important to me than school."

Chet caught a ghost of a smile forming on Vanilla's muzzle. "Your dad didn't understand, did he?"

Chet looked down at the tabletop he was sitting on. He stared at his empty hands. "No. He didn't. He and Arthur stopped being friends when Arthur made my job official."

"Did you drop out of school?" Vanilla asked quietly. Expectantly.

The human nodded. "Yup. I was going to fail anyway. There was no point. So I just stopped going. My dad... that was the first time he yelled at me. At least the first time that I can remember."

Vanilla took a moment to tuck a strand of hair behind her ear. "So you started working at the hotel. Was it fun?"

Chet laughed. "I'm not sure fun is the right word. I enjoyed it though. People didn't walk in and see an idiot. They walked in and asked for a room. A service I knew how to provide. It wasn't a quiz. They weren't testing me. It was so much easier than school and it was a legitimate job. My dad just didn't care for it though. That was the hard part. He was never proud of me and I destroyed his friendship with Arthur. Now I've gone and disappeared from the universe. Some son I turned out to be."

The mare looked pained. "I don't think that's fair. You chased your dream is all. And you didn't choose to get dragged to Equus."

Chet shook his head. "I don't know. Maybe I could have tried harder to explain. Make him see the hotel was important to me and that it was a legitimate job. I don't know. I just feel like I could have tried harder."

"That must be tough," Vanilla commented sadly.

Chet couldn't help it. The question popped out of him before he could think better of it. The man wanted to know. "What about you and your dad? How does he feel about you working as a maid in the castle?"

Vanilla's eyes went so wide he thought they might fall out of her head. Then she looked away. "I... don't know if he even knows."

Chet was lost by that. "How can your dad not know you work here? This is a pretty prestigious place."

The mare squirmed uncomfortably, obviously not liking being the target of these kinds of questions. "Me and my family don't talk. I haven't spoken or written to them in three years now."

Again, Chet couldn't help himself. "Why?"

Vanilla didn't say anything for a while. Just when Chet was starting to think he should hard shove this date in a direction that wasn't an interrogation, she found the courage to answer.

"I... don't actually know much about my dad." Vanilla sighed and hugged herself. Chet could hear her legs moving under the table. "He had something to do with the nobles. An assistant or an administrator? I never found out. But he retired early and bought a ranch out in the country. He raised me and my older brother to be tough and hard working. He gave us each a choice. We could join the military or work the ranch. I didn't like either."

Chet felt a sense of horror creeping up his spine. "Did... he beat you?"

Vanilla's gaze snapped to him. "No. Well... he shoved me a few times. He held me against a bookshelf once and yelled at me. He told me that if I wasn't strong the world would chew me up and spit me out. I think he saw it as 'tough love'. My older brother agreed with him. Only my mom thought my dreams were worth something."

Chet was disgusted. And he had had the nerve to think his own upbringing was rough. At least the mess could be called his own fault. "What did you want to be Vanilla?"

She smiled, but there was something broken in her expression. "An actress. My parents took me into the city several times when I was young. We went to various places, but I always loved the theater. The actors, the stories, the songs. It was... fun. Then they'd drag me home and put me to work. I always looked forward to those trips though."

Chet glanced around the room as he thought. Vanilla wanted to be an actress, then what was she doing working as a maid? Something must have gone wrong. Did he... did he dare ask her to relive that?

Chet stood up, which made Vanilla watch him curiously. "This hasn't been a very fun date."

She looked thoughtful for a moment. "Oh," was all she could say.

"Vanilla, I'm not going to lie. I'm really curious about your... past. But we're supposed to be on a date so maybe we should talk about something more upbeat."

She rubbed her arms a few times like she was cold. He heard her hooves tap against the floor below. "You told me about your life, shouldn't I do the same?"

"Well," Chet mumbled while scratching his head and ruffling his hair. "Yeah, I guess. But dates are supposed to be fun. Are we having fun?"

"I thought dates were about bonding?"

The man pursed his lips at that. "Are... are we bonding?"

"I thought so."

Chet scoffed. "I never understood that idea. Bonding over... pain. You're supposed to bond over things you enjoy."

Vanilla looked away. "I... do want to talk about it though."

Chet blanched. "You want to talk about that terrible stuff?"

"I never told anypony before. It feels... good," Vanilla asserted. "And Cadenza said I should."

"I thought you said you never told anyone. How can Cadence tell you anything about it?"

Vanilla glanced at the ceiling. "Cadence explained to me the best way to make this relationship work. She used a weird analogy that went something like..." the mare droned off for a moment as she struggled to remember what she had been told. "Princess Cadenza said that the two of us are gears and that we fit almost perfectly together. However, my gear has two teeth that don't fit with yours and your gear has a tooth that doesn't fit mine. If we can deal with those three bad teeth we will become inseparable."

"Sounds like a dentist joke," Chet mumbled.

"The first bad tooth on my gear... is my past," Vanilla finished, ignoring his interjection. "I want us to be... a thing. So... I have to talk about it. I think."

"I... I want this to work too," Chet added. It was now he also realized that, while he had come to this date with no real plan, Vanilla had been almost entirely prepared. From the very start she had intended for them to talk about this.

Vanilla smiled a little at that. "So... did you want to know more?"

"Not if it hurts you."

"I... don't think it will."

Chet was very curious. His life at the hotel was one constantly collecting gossip. It was natural for him to want all the juicy details. But he was trying to hold that back. This wasn't a happy story he was poking into. He licked his lips nervously. "You... you wanted to be an actress, right?"

"Mhm," she hummed confirmation.

"Did you run away from home?"

"Yes," she said simply. "My brother was getting more and more aggressive. Trying to force me to do more chores. My dad was yelling all the time. He didn't like anything I did. How I dressed, how I walked, anything. So I took some money and fled to Canterlot."

"Did anyone come after you?"

Vanilla shook her head, her mane flopping back and forth. "I haven't been arrested yet."

Chet sat back down, getting more comfortable for this. "That's good. So why didn't you go to the theaters, start working on your portfolio and all that?"

Vanilla sighed. "I tried. But that's not how the theater works." She glared down at her lap. "Funny, I loved the plays so much but I didn't learn anything about how they worked before running away. You see Chet, to get an acting job at even the cheapest theaters you need an acting degree. They won't even talk to you if you don't have one. But guess what you need to attend an acting school?"

Chet swallowed back the dread. "Money," he guessed.

"And connections. The exact connections my father had." Vanilla scowled. "In order to achieve my dream I needed my father's help. But I wasn't about to go back. I had already begged him before, his mind was never going to change. So I was trapped in Canterlot, there was no way to pursue my dream, and the money I had was running out. I was sure I would have no choice but to crawl back home. I wasn't sure what else I could do. Then I got a job in the castle." The mare's face brightened a little. Not much, but a little.

"A lucky break? Do you like being a maid?"

Vanilla seemed to think about that for a while. She tapped the table with a finger. "I don't know," she eventually admitted. "It's kind of a weird place to be."

"What do you mean?"

"Being a maid isn't exactly a respectable job. Few ponies appreciate it. However, I'm working in the castle for royalty," she gushed with a hint of pride. "Being near the Princesses is an honor. There are a lot of ponies who just might do anything for a chance to see royalty every day."

Chet sighed with relief. The tense part seemed to be over. Hopefully it would be smooth sailing from here. "So you do like it."

She shrugged. "At first it was scary. But after watching Princess Celestia walk by a few dozen times the novelty starts to wear off. The job is just a job now. Doesn't really feel that special anymore. I still want to be an actress."

"You work for the Princesses, you should have enough money."

Vanilla frowned. "Acting lessons are very expensive and I still don't have the connections to even get in the door. I... I've almost given up honestly."

That was a hammer through the glass window that was their date. So much for a fun time. This was truly a disaster. How was he supposed to comfort her after that? Chet scrambled for something he could say, but drew a complete blank.

"I'm sorry," the man said pathetically.

Vanilla shook her head. "It's okay. Dreams change." The way her eyes were locked on him and seemed to brighten gave Chet an idea what she meant. He felt himself starting to sweat under that gaze.

"We REALLY need to talk about something happy now."

"Alright. What should we talk about?"

Chet groaned in frustration. "I don't know. Here I wanted this to be all cheerful and romantic. But all we did was... share horror stories."

Vanilla's ears fell. "I'm sorry. I just thought we had to do that."

"Because of Princess Cadenza?"

"I trust her."

Chet chewed his lip for a moment. "Are we closer now?"

"I... I think so. We're a lot alike." Vanilla rubbed an arm.

The man considered that. "I guess we are. We both had dads that didn't understand."

"We both lost our dreams," Vanilla said with a wistful look.

"We both have new dreams now." God that was the cheesiest thing Chet had ever said.

Vanilla giggled. "Now that is romantic."

Chet blushed with embarrassment and turned away from her. "Yeah... well... I'm hungry!" he suddenly announced.

"I am too," the mare glanced at her stomach as though abruptly realizing the same thing. "Do you want me to get you something specific?"

Chet shrugged. "Just don't get me any flowers. I can't eat flowers."

"Okay," she nodded and shuffled out of the booth.

As the towering equine made her way across the room to where the food was, Chet watched. Her tail swayed, her hips rocked, her skirt flapped. The man stared at her bubble butt as she walked away.

"Three teeth that don't fit," Chet muttered. "One was her past, that leaves two more. Was my bad tooth my past or my height? No, she wanted a man who was smaller than her. Oh well, we'll figure it out on the next date."

Author's Note

Three drafts and two tone shifts later created this final piece. I'm honestly not sure how to feel about it myself. I always knew I wanted both characters to have semi-tragic backstories and I knew I wanted them to share their stories during the first date, but when I wrote that first draft I immediately felt like I'd made a huge mistake. Because date + tragedy = bad? It didn't feel right. So I wrote a second completely opposite draft where they just sat and chatted for a while. It. Was. Boring! So I went back and tried "backstory date" again. The first time I had done it more like speeches. Each of them just described what happened in two or three long paragraphs. When looking at that a second time I realized that was the problem. Normal people do not talk like that. We interrupt each other. We ask questions. We comment. Once I had them breakup each other's stories it read much better. But there was still the oddity that this was supposed to be a date, why was it so dark? So I tried to lean into that strangeness. Make it feel unusual to the characters too. Not sure how well that worked.

The hardest part of this story is the "twist". It's the kind of thing there is no way to do without ambushing the audience. But if I just tell everyone in advance, it's not much of a twist. It felt like an unwinnable position to be in. How do you tell an erotic story where the big surprise is the mare actually being a stallion without pissing off a large portion of your audience when the reveal is made? So I just spoiled it with the title and the description and felt like a bit of a failure. Then this chapter naturally created something I really liked. A double-story effect.

From Chet's perspective Vanilla's story is a tragedy. Her father wasn't interested in raising a daughter and tried to force her to act like a stallion. However, we as the reader know the one key detail Vanilla didn't share with him. At one time we can understand both Chet's opinion of the story and what likely really happened. A father who didn't understand why his son was so feminine. Who thought he could "work" the submissive nature out of him. Vanilla's father isn't necessarily a bad man, though it is easy to interpret that he was given the vague details, he might have just been a very traditional masculine male who didn't know how to deal with his son. More of a failed father than a bad father. If the difference matters.

I liked that effect. The two layered stories we as the reader can pull out of this at the same time. Made me feel like the decision to reveal the ending twist wasn't simply giving up. It let me do this instead. I may not be entirely proud of how the date itself turned out, but I'm definitely proud of the double-story effect going on.

How To Love

Version: 1

"What the hell Cadence!?" Chet barked as soon as the pink alicorn sat down.

For her part, the Princess looked more confused than offended. "I beg your pardon?" she asked while professionally folding her hands in her lap.

They were in the conference room where Chet and Twilight normally talked, though the purple pony was not present for this meeting. The man had asked to speak to Cadence as soon as his date with Vanilla was over. However, the Princess of Love had been busy with other matters and couldn't take time to see him for two days. His mood had not improved as a result of the delay.

Chet steamed for a moment then crossed his arms. "My date with Vanilla," he hissed. Princess Cadenza raised a brow expectantly, waiting for him to elaborate. Only when she was sure he had no intention to expand on that did she speak.

"I don't understand, according to Vanilla it went well. So why are you upset?"

Chet huffed. Then the man aggressively ran a hand through his hair. "You talked to her before our date," he accused.

"Yes," the pink pony admitted coolly. "She wanted advice."

"Why didn't I get any advice!?" Chet yelled.

"You didn't ask," Cadence replied matter-of-factly.

Chet glared at the towering mare for several seconds. Neither of them spoke. A clock in the corner ticked. The man sighed and fell back on the pile of bits he used as a chair. He rubbed his face. The alicorn regarded him with concern.

"What's wrong Mr. Bowman?" she asked tenderly, leaning forward.

The human shook his head before meeting her eyes. "I felt so... ambushed. She had it all figured out and I didn't have a clue what I was doing."

"Oh Chet," the Princess cooed, using his first name. "Dates aren't about preparation, they're about honesty. That's all I told her she needed. To be truthful about who she is."

The man massaged his forehead and looked down. "I wasn't ready for that. I should have been. But I wasn't."

"You weren't ready to be honest?" He could hear the disapproval in her voice.

"No," Chet said quickly and waved a hand. "Just... I wasn't ready for such a... serious discussion. I thought it'd be... more relaxed," Chet admitted with a shrug.

Cadence took a moment to consider her next words. "Do you want advice?"

He chuckled sadly. "Yes please."

"Why?"

Chet stared up in confusion. That was the last response he expected. "Because I don't want to screw this up," he explained bluntly.

Princess Cadenza smiled. "So you acknowledge that you want to love Vanilla?"

Chet narrowed his eyes in thought. "Yeah?"

"Good. You've made excellent progress."

"Huh?" he honked. "What do you mean?"

"Have you already forgotten our first meeting? You were quite set against this whole arrangement," Cadence chuckled.

Chet scratched the back of his head and looked away with a blush. "Well she's a nice mare. Understanding and... all that mushy stuff." He faced Cadence again with a tight expression. "And I don't want to hurt her. So I need to do this right. Okay?"

The alicorn hummed approval. "What did you learn from your first date with Vanilla?"

Chet rolled his eyes. She couldn't simply tell him what to do. She just had to be all mysterious. "Vanilla told me about her family and how she came to work at the castle."

Princess Cadenza shook her head. "No Chet. You're focusing on the surface level. Dig deeper. What did you learn about your relationship?"

Chet slumped in his seat. That was a lot tougher. "I don't know. That Vanilla is shy in public spaces? So we shouldn't do things with a lot of other ponies around?"

The mare giggled. "That's a little better."

The man grumbled. "Are you going to help me or not?"

Cadence cleared her throat. "Of course. You seem to be terribly ignorant about relationships, so you need all the help you can get."

Chet huffed. "Yeah yeah."

The pink alicorn sat straighter, a lot like Twilight did before entering lecture mode. "It is my belief that the biggest obstacle for you and Vanilla will be your ability to view each other as individuals. You because Vanilla is so much bigger and is going to have all the physical power. And Vanilla because you are so small and easy to... bully."

The man nodded. "That... makes sense."

"If the two of you are going to form a lasting bond you first need to appreciate that the other is a person with their own history. As Twilight might say, 'each pony is a story being meticulously written page by page, day by day'. There are two main reasons relationships fail, Mr. Bowman." She held up two fingers. "Money and control. For you and Vanilla, money won't be much of an issue. But control will decide if you two are truly compatible."

"Control?" Chet mumbled.

"Tell me, Mr. Bowman, which of you will decide where you go out to eat?"

"Uh, both of us?" It seemed like a completely normal answer.

"What if you can't agree? Then what? Who gets to make the final say?"

Chet bit his lip. "I don't know."

"Wouldn't Vanilla be the ultimate authority? She will be the one carrying you. Will your opinion even matter in the first place?" Cadence challenged with a raised brow and a slight tilt of her head.

The man grimaced. "She wouldn't do that."

"Why not?"

"Because..." Chet's words faded with uncertainty. He had no counter argument.

"She has to see you as a person with thoughts and feelings. If this relationship is finalized, you will be put into her custody. You'll be living together. Then you will be entirely at her mercy, won't you? You'll have to rely on her kindness and understanding. Yes?"

Chet swallowed nervously, but didn't say anything. It was a curt reminder of how vulnerable his small size made him. But would Vanilla really take advantage of that? She seemed so nice.

Cadence nodded somberly. "Control is a problem for even conventional couples. When disagreements arise, many ponies fall into the trap of failing to recognize their partner as just that, an equal. 'My stallion' or 'my mare' sound like romantic phrases, but they can easily lead to a dangerous mindset. It can make one believe and act like another is their property and therefor under their control. The ability to compromise is lost. If a couple has no means of dealing with a stalemate, the relationship might shatter then and there."

"I see," Chet acknowledge while scratching his head. Cadence really was an expert.

The princess sighed. "That is my biggest concern for you and Vanilla. Ultimately, she will get what she wants if the two of you ever get into a fight. Before you two can form a lasting relationship, she will have to prove she knows when to submit to your desires and you will have to learn to trust her."

Chet winced at that. "So what do we do?"

"Build trust, Mr. Bowman. The next step is integration and trust."

"What does that mean? How?" the man threw his hands up.

Cadence sighed again. "You need to prove to yourselves, and each other, that it is possible to be a couple. You need to spend time together that is not strictly talking."

"An activity," Chet translated.

"Correct. Now you need to do something fun. Something that requires cooperation would be best."

"Like what?"

"The best way would be to let Vanilla hold you."

Chet blinked. "What would that do?"

"Prove that you trust her with your life."

"Would... holding me really be that significant?"

Cadence froze, her expression shocked. "You are not afraid of being held by a stranger?"

"Not... really?" Chet answered uncertainly, remembering what he'd told Vanilla during their date about being surrounded by giants who were all eager to help him. The Princess detected his hesitation however and narrowed her eyes skeptically.

"Mr. Bowman, you are not afraid of being held? Of being helpless? Really?"

Chet squirmed. "Well... at first I was. Not so much anymore. I think I got used to it."

Cadence snorted. "You may be human, but you are so like a typical stallion."

"Hey," the man grumbled.

The Princess shook her head and cleared her throat with a cough. "The ponies who always carry you are your guards, correct?"

"Yeah. They escort me wherever," Chet confirmed with a shrug.

"When is the last time a pony other than your guards held you?"

Chet took a moment to think. "I don't know. Twilight held me a bunch at first. Then there were some of the science ponies. That... was uncomfortable," he mumbled as he searched through his memories. Who was the last non-guard to hold him? Twilight?

"I've never held you," Princess Cadenza added smoothly. "Would it be alright if I picked you up now?"

In that moment, Chet was suddenly very aware of how large the alicorn was. His attention was dragged to the angle of his neck and how far back he had to tilt his head just to make eye contact. His brain made him realize how blurry she was despite filling up so much of his vision, further emphasizing her sheer enormity. He was but a speck, an ant, gazing up at a mountain of pink fur and flesh. A thing closer to a goddess. Even waving her hand created a whooshing sound Chet could hear. Her voice was powerful enough that if she was too close he could feel his very bones vibrate. The man suddenly felt afraid.

"No," Chet said with a shiver.

Cadence tilted her head curiously. "Are you alright Mr. Bowman?"

"I'm... fine," he said dismissively and rubbed his arm.

"I've never gotten to hold you, why won't you let me?" she asked in a leading tone. "Did I do something wrong?"

Chet swallowed. He could feel himself sweating. His mind was filled with thoughts of what she could do to him. He knew she'd never hurt him, but...

"Princess Cadence."

"Yes?"

"You made your point. I... I'm afraid of letting you hold me."

Cadenza's ears pinned and she sounded genuinely hurt. "I understand, Mr. Bowman. And I expected as much."

She scooted back in her seat and the two of them were silent as Chet calmed down. After a minute the Princess began to explain what Chet was just starting to realize.

"You feel comfortable with your guards because of familiarity. You don't just consciously know they will keep you safe, you subconsciously know they will keep you safe. It's experience. You were terrified every time they held you in the beginning, weren't you?"

Chet only nodded. She was right. He couldn't deny it. All it took to prove it was her asking if she could hold him. It was disturbing how easily she could see through him.

"I've never carried you before and we haven't spent a lot of time together either. To be held is to put yourself completely at the mercy of another. It requires a tremendous amount of trust. You never noticed how proud your guards are to have earned that from you, did you?"

Chet perked up at that. "Wait, what?"

Cadence smiled. "Your guards take an immense amount of pride in your trust. Whenever they carry you... they feel powerful. And an overwhelming sense of responsibility. They volunteered for the position you know and they enjoy it a great deal. They're very protective of you."

Chet felt his jaw drop at that. "I thought ferrying me around was annoying. Something no one wanted to do."

The Princess chuckled. "The very idea of holding an entire person who is so small, delicate, vulnerable..." her voice and eyes drifted. "It's hard to explain the feeling. I have no doubt Vanilla feels the same way I and many others do about it."

Chet blushed but he wasn't sure why. "You... really want to hold me? Is it really that special?"

Cadence looked away and blushed herself. "Yes. There's just something about the thought of it."

Another silence, this one much more awkward. Again it was Princess Cadenza that eventually ended it.

"That's why you should let Vanilla hold you. It's a sign of trust and I'm certain she wants to."

Chet rubbed his hands together and breathed. "So we should do something fun and... I should let her hold me."

"That's my advice Mr. Bowman," the Princess nodded.

He licked his lips. "Okay. We'll have to arrange another date. A happy one this time."

"Yes. That sounds like a good plan," Cadence smiled.

Chet eyed her for a moment and his mind turned. Now that he thought about it, she had done a lot for him and he had done literally nothing for her. "Princess Cadenza?"

"Hmm?"

"Thanks for the advice. You've been a big help with... all this stuff."

She grinned. "Your welcome Chet. It was my pleasure."

"Will it work out?" he blurted. Even he was surprised by his own question.

For a moment her eyes widened and she stared at him. Then Cadence lowered her head, tapped her chin, and her brows creased in concentration. For some reason the action made Chet uneasy. "I won't lie to you Mr. Bowman. Your relationship is unique and it will require determination and effort to make it work. Both of you will have difficult decisions to make. Though Vanilla has already at least partially accepted one of the realities living with you will require."

Size. Cadence was talking about size. Vanilla had already accepted the strains that dealing with Chet's height would put on her. The man nodded. "Yeah, I knew it wasn't going to be simple. But I think I've come to terms with dating a giant."

Cadence looked conflicted. Doubtful. She didn't believe him. And why should she? He'd lied to her and even himself about his fears of being carried. "Mr. Bowman. There is... one great obstacle that you will have to face before your relationship can truly solidify. At best I can offer advice and encouragement, but ultimately it is up to you. Do you love Vanilla or not? Who is she to you? What does your relationship mean?"

The questions hurt a bit. Chet felt like he'd been slapped. That she'd basically called him out as a liar. Which she partially had, though Chet also had to admit to himself that he had sort of lied. It made him feel guilty. He wasn't a bad guy. He didn't want to be anyway.

Chet's shoulders slumped. "I know I don't really love Vanilla, not yet that is. You can't really love someone you don't know that well. But I want to. And if I want it then I can make it happen." He blushed as soon as he said that. How embarrassing.

Cadence giggled. "I should apologize. You seem to know more about relationships then I thought. However, you should be careful about deciding to love her before you know for certain who she is. That could backfire terribly if she turns out to be... undesirable," the Princess warned darkly.

An ominous shiver went up Chet's spine. Cadence obviously wasn't trying to tell him to dump Vanilla. It was a general warning. He was sort of getting ahead of himself. He couldn't simply decide to love someone and get the reasons for it after the fact. That made no sense. He had to get the reasons first and love would form naturally from there. Then the man considered how Vanilla and him had first met and how they had gotten this far.

Chet chuckled. "Our relationship is going to be completely artificial at this rate."

Princess Cadenza quirked a brow. "Just because something is artificial does not mean it can't be precious or beautiful."

Chet hummed at that. "Maybe. But you're instructing both me and Vanilla how best to... manipulate each other into love. Isn't that kind of... I don't know, fake?"

The pink alicorn considered that for a while. She closed her eyes and thought. "Perhaps," she eventually agreed. "However, art is not natural. It requires a painter to decide where each color will go, to orchestrate the lines, to decide the final shape. Yet we don't see art as being 'fake' or wrong."

Chet shrugged. "I guess. I just meant that this is all pretty weird is all."

Cadence smiled playfully. "You are a minuscule alien from another reality. Weird is your life from now on."

He snorted and rolled his eyes. "Too soon."

Princess Cadenza coughed and sat straighter. "Well, is there anything else you need from me while I'm here?"

Chet thought for a second, then decided to satisfy one minor curiosity. "How much have you and Vanilla talked?"

The mare glanced up and tilted her head. "We talked when I first detected her as a possible match, before your date, and after your date. Though our discussions were certainly longer than any I've had with you."

That peaked Chet's curiosity. "And I thought I needed help with this dating thing. She really needed that much coaching?"

The Princess hesitated. "I... do not believe it would be appropriate to reveal Vanilla's... insecurities. Her perspective of your relationship is... very interesting."

"Should I be worried?" he asked a bit nervously.

"I do not believe so," she replied quickly. "In fact I think it might even be important for you two to discuss some of the points she made to me."

"Like what?"

Cadence blushed. "I believe she was actually quoting you. 'The ultimate point of dating is sex.'"

Chet's eyes widened and he blushed too. "Oh," he whispered. "Vanilla was quoting me alright."

"You are not entirely wrong," the Princess sighed and looked away. "However, to be more accurate, the true purpose of marriage and love is children."

"Which requires sex," Chet added a bit sarcastically, hoping to soften the awkwardness he dreaded might be coming.

The Princess pouted. "Yes, to put it bluntly. Sex does tend to make children. However, you cannot."

The man blinked. "What?"

Cadence met his eyes, the mood dropping in an instant. "Chet, you will never have offspring. You can never have children. You are the first, only, and last human on the entire planet. And there is zero chance you are genetically compatible with us ponies. So any mare who chooses to marry you is doomed to either childlessness or adoption. I believe you once told Twilight that adoption is not particularly rare on Earth? Well it is exceptionally rare here on Equus. Not unheard of, but still."

Chet winced. "I see. I never considered that." He really hadn't. Sex was great and all, but what about family? Chet had given up on that himself, but what about his potential wife? Marrying him would be a dead end.

The pink alicorn smiled tenderly. "Don't worry Chet, that's one of the advantages of my matchmaking spell. Vanilla was never interested in children. That trait is but one that makes you two compatible. She isn't interested in having foals and you can't have them anyway."

Chet leaned back in his seat. "That's a relief."

Cadence watched him for a moment. "However, that leads to a question. The two of you can never have kids, so why are you a couple?"

The man itched his temple with a finger. "Fun?"

The Princess chuckled sadly. "I suppose 'fun' is fine. But I would have suggested companionship or the ability to share your struggles."

Chet snorted. "Maybe I'm just shallow."

"If you are, so is Vanilla."

Chet shook his head. "Was that a joke? It sounds like a recipe for disaster."

Cadence looked away, but he saw a small smile on her muzzle. "It depends. If the two of you can be happy together, that's enough." Then she faced him again, her expression now stern. "Fair warning Chet, keep in mind what it is you are looking for in a mate. Before you make any rash decisions, consider why you're making them. Okay? Promise me you'll think before doing anything reckless."

Chet threw his hands up in defeat. There Cadence went again, worrying about him. Maybe she was right to. "I won't do anything stupid Cadence. You don't have to worry about me."

She hit him with a mild scowl. "You'll get over any mistake you make," the pink mare grumbled. "It's Vanilla I'm worried about. Don't... don't hurt her if things go wrong."

Chet stared at Cadence for some time. How could she think he would intentionally do something to hurt Vanilla? He almost felt insulted. However, she'd been right about him so much already, her latest warning actually made Chet pause. If Vanilla turned out really not to be the one for him, would he know how to turn her down gently? Without crushing her spirit? She clearly wanted them to be a thing. If Vanilla rejected him in the end, Chet had Cadence to find him another mare and he could try again, but what did Vanilla have to rely on? What was her backup plan?

Chet swallowed. "I'll... try not to break her heart. I promise."

The Princess didn't respond for at least a minute. When she did it was a simple, "okay."

And that was it. Cadence returned to her duties and Chet was carried back to his room. Though he had a new appreciation for the hand he sat in and the guard it belonged to. He had a lot to think about. Mostly what form his next date with Vanilla should take. They had to do something, an activity, that required them to work together. They had to practice trust. His mind also buzzed with Cadenza's warning. He really wondered if this relationship would work out, if they were trying to force something that wasn't meant to be, and how much he hoped that wasn't the case. Was he getting ahead of himself and rushing into a disaster? If he was it was the Princess's fault. She had assured both of them that they were "nearly" perfect for each other.