Why Sassy Saddles

Outside the workshop, there was the beginnings of a beautiful spring morning. The sun had just started to make its presence known in the east. Any sign of last night's storm had all but vanished, leaving only a few wispy clouds surviving. A pony Anon was not familiar with trotted passed the street outside the yard. She had a cart full of goods. Up early he suspected, to prepare for the Thursday flower market.

The scene was tranquil, and he admired it as he closed the doors on the workshop. The dew hung on everything, and the air was cold and crisp. Anon tried his hardest to suppress a yawn but one managed to force its way onto his face. He guessed he was pretty tired. It would not inhibit him from finishing the job though. Anon would push through. He also wanted to ask the mare in front of him out to a party.

He knew though that when the time came, he would chicken out. He was never any good at stuff like this. Going with her was really just keeping the fantasy alive. He knew that if he really had the balls to do it, he would just do it now.

Alas he wouldn't, and the pony in front of him seemed impatient to get going. She had seen Anon yawning and was probably concerned for his state of mind.

“Come on let's go!” Anon said in an overly active and joyous voice, poorly compensating for the previous display of fatigue. It wouldn't have even fooled a 5 year old.

Anon and Sassy set off. He went out of the archway and up the street towards the centre of town. A comfortable silence fell between them. Unbeknownst to each other, they both had a lot to think about.

Anon had a crush. The first one in a long time. Sassy saddles was slender and undeniably beautiful, and yet had a modest grace and technical skill, which was not often possessed by one with such beauty. She seemed to like him as well, although he couldn’t tell if there was anything romantic. Doubts started to creep into his mind. Perfectly logical ones at that. Of course she’d never like him. He was a different species! He probably looked grotesque and strange to her. She also hadn't shown any interest in him. No more than someone becoming new friends would anyway. A twinge of guilt flushed over him. Anon had been perving on her whist she had been asleep. Although the sight was oh so hot, he had regretted it the minute he walked away. ‘Was that something a respectful guy would do’? Of course it wasn't. It would be a secret he’d have to live with forever. The image was seared into his mind and would probably resurface in a fair few fap sessions in the future. Maybe he was just the scum of the earth, and had no chance with Sassy because of it.

Sassy meanwhile was lost in her own train of thought. How could she dream about such depraved things. Interspecies relationships were not particularly frowned upon in Equestria, just very uncommon. She wondered what it was about Anon that made her feel this way. She certainly liked his form, and his strength and imposing size definitely got her hot.

She suspected she knew the answer to that question, but didn't want to admit it, pushing the thought to the back of her mind. Hopefully it would stay there. She thought of other reasons she liked him. More noble reasons. He had shown himself to be kind and thoughtful, and he was also extremely dexterous with his hands.

Sassy shook her head. ‘No! noble reasons get your mind out of the gutter’ she scolded herself. He was brave and above all, she trusted him.

Her thoughts faltered. Who was she kidding. She didn't know anything about the human. She had known him less than 24 hours. She didn't really know what he was actually like. ‘He might enjoy kicking puppies in his spare time for all I know’ she thought. It occurred to her that he was right next to her still, and she could probably find out some more about him with some casual conversation. Now she only had to think of something to ask.

“So Anon, where do you live?” She asked.

The question came out much more awkwardly than she had anticipated. There's nothing weird about asking where someone lived was there? Anon seemed to have been jolted out of his thoughts. Sassy just took it as further confirmation that he was extremely tired, and Anon was perfectly willing to let her believe that.

“I live on the Far West Way. A couple of miles from here,” he said casually.

“I think I know the place. Can't say I go there very often though.” Sassy replied.

She remembered the place being pleasant enough, she just had no reason to go there. It was out of the way; in fact it was the opposite direction to the one they were currently walking. It made sense really. She would definitely have noticed and remembered the human if she'd seen him passing on the street before. Sassy was very aware that the growing flow of morning work ponies would stare at and subtly take steps to avoid the man. It made her feel angry and a bit sorry for Anon, maybe because she suspected she would have done the same thing had she never spoken to him.

“Does this ever make you feel sad?” Sassy said

“Does what ever make me feel sad?” He answered with another question, not sure what she was on about.

Sassy gestured around. “The ponies. They’re wary of you”. She said. “They avoid you. Don't you want to fit in?”

Anon knew exactly what Sassy meant, but truth be told it didn't really bother him. He had never met a pony who was outright disrespectful, and the opinion of random strangers did not matter to him in the slightest.

“Not at all. It doesn't make me sad. My friends treat me normally, and I don't care what the average town pony thinks. Ponies I know, like you for example, are the only ones whose opinions I care about.” Anon said. “Plus, how exactly am I going to change to fit in more. Grow a tail? Shrink a bit?”

“Okay, okay, I get it! you don't care. You only value the opinions of ponies who know you. Like me,” she said gleefully, unaware how obvious the reason for her happiness was. Lucky for her though, Anon was oblivious to such things. To him, she just seemed naturally upbeat.

“So, you are attending this fashion show tomorrow. What will it be like?” He inquired.

“Well for me, very stressful. I'll be handling all of Rarity’s portfolio. Not that it's not good fun of course, I’ll just be very busy.”

“Oh okay.” He said. “Does that mean you'll be relaxing over the weekend?”

The question through off Sassy's composure. She was completely free over the weekend. She would be lounging around, eating ice cream, and reading a book. She couldn't tell him that though. He would think she was lazy, anti-social, or had no friends. She had to think of something quickly!

“No,” she said. “I have lots to do over the weekend. I'm going out with some old friends that are visiting Canterlot.” she said, a bit aggressively, her British accent punctuating each word.

‘Well there goes that plan’ Anon thought. It made sense that a successful mare like her would be busy on the weekend.

“Oh right,” he said, try not to sound rejected. Anon reached his hand down and felt his back pocket. The invitation had most definitely been crumpled by the sewing machine. The weight made it hang abnormally low, bouncing rhythmically against his rear. Anon has to accept it really was just a pipe dream.

“You doing anything?” Sassy inquired.

“No, it's just a quiet weekend for me,” he said. The words hurt. He could imagine himself in the workshop, sitting in silence. He loved his work; it was just… lonely. Anon thought he was fine being alone. Yesterday he woke up perfectly happy with his life. He didn't have a care in the world, but now though, he wanted more. He saw potential. A glimmer of hope that his life could be fuller, happier, but it was just a fantasy which had run away with him, and could never be.

Anon decided he needed something to cheer him up. He couldn't let his hopeless mood show around Sassy, and the best way he could think of to achieve this was to improve his mood.

“Hey, shall we stop quickly for some breakfast?” Anon said, a passable amount of cheer in his voice.

Sassy looked unsure. Time was ticking on.

“I don't know Anon. Rarity really needs us to return,” she said.

“Well we'll just get something to go then,” he suggested. That way it wouldn't cost them any time.

“Yes, I guess we could then. I am pretty hungry.” Sassy mused.

Just then a large cream coloured building appeared over the horizon. The shop had a large wooden sign out front, and an outdoor seating area. The place was obviously popular, it was swarming with ponies. ‘Ahh, Donut Joes,’ he thought. The ideal restaurant for any fic set in Canterlot.

“This seems like a good place,” Anon said.

He directed Sassy towards the shop. She hung slightly behind him as they entered through the large glass doors. The shop was packed, good job they were just taking food to go. He walked up to the counter. A large stallion stood behind it. He looked busy, but seemingly enjoying himself.

“What can I get you?” Anon asked Sassy.

“I'll have the chocolate and cream eclair please.” She stated.

“And I'll go for the caramel donut,” Anon said.

The stallion, who had been listening to both of them, immediately opened the display and pulled out two of the sweet pastries. He wrapped them in waxed paper, and then brought them over to the register.

“That'll be four bits,” he said.

Anon reached into his pocket and found four bits to pay the pony. Sassy didn't show any expression on her face. She didn't do anything in fact. It was impossible for Anon to tell what she was thinking. He thought she might have protested the action, but she just stayed motionless. He was relieved actually. He didn't mind paying for someone who was respectable, and good company.

Anon left the shop and unwrapped the donut, taking the first bite as he continued on the final leg of the journey. Sassy held her food in her golden aura, taking a bite from the end of the eclair. She was enjoying it a bit too much. She didn't normally allow herself to have such sweet things, but she’d indulge herself just this once. Anon bought it for her after all, and she couldn't turn it down, that would be rude.

They both finished the delectable treats just as they came into view of the Canterlot carousel.

“Mmmm, that was delicious, thank you Anon.” Sassy said gratefully.

“No problem.” Anon replied, looking down at her. He stifled a giggle at what he saw. Sassy had cream all around her mouth and was totally oblivious to it. They were right outside the entrance to the shop, and she couldn't go in looking like that.

“Ha, you've got some cream on your face!” He said.

“Oh, do I?” She said in an unusually shy tone for her. She stared down at the end of her nose, going slightly cross eyed, before unsuccessfully trying to lick it off. The sight was incredibly adorable.

“Come here I'll help you with that,” Anon said, seeing that she couldn't get it.

He bent down and got close to her. He got his hand under his t-shirt and used it to wipe away the misplaced food. Sassy would have found it disgusting, but she had been craving the intoxicating smell of the human ever since last night. She subtly breathed in whist he wiped her mouth. His natural odour was more than enough to overpower all the dirt on the garment, at least in her mind.

“That's better,” he said. “We couldn't give Rarity any clues that we had stopped for a bit could we.”

Sassy nodded, a little bit of pink had formed on her cheeks.

Anon pushed through the doors and into the boutique. Initially he saw many ponies in the shop, but quickly realised they were all mannequins, and the room was devoid of life. Sassy trotted past him and called for Rarity. A reply came from the adjacent room. Both of them followed the sound through the doorway into Rarity’s workroom. The room was full of different fabrics and half finished garments. Some might even call it messy. Anon liked it though. It reminded him of his own workspace, and showed that real design work was going on.

His eyes fell upon a pony sitting on a stool over by the window. She had an urgent and purposeful look about her, but she honestly looked more put together then Sassy had described.

“Good morning,” she said, getting off her stool and waltzing over to him.

“I was beginning to worry that something had gone wrong.” Her attention was directed towards Sassy Saddles, and looked surprised when she also noticed Anon in the room.

“You must be the repair man,” she said politely but in a purely professional tone.

“I'm Rarity. The owner of this boutique. I believe you have something of mine.” She gestured to his heavy bag.

Anon dismounted the bag from his back, opened it and lifted the box out.

“Where would you like this put ma’am,” he said. Elements from his teenage job as a waiter coming back to him. Sassy coughed and spoke up. She was not impressed by how rude Rarity was being to her new friend.

“Rarity, this is Anon. He’s the craftsman that pony told you about. He's frankly saved our flanks after your mistake.”

It was unclear whether Rarity had realised that Sassy was disgraced by her rudeness. But from then on, Rarity started treat him like more of a sentient creature, so he guessed the message must have gotten through, at least subconsciously.

“Would you like it unpacked,” Anon asked Rarity.

“Yes, please,” Rarity said. “Over on the desk by the window.”

He moved the box and unpacked it. Rarity crowded around him, looking the box up and down, before looking him up and down.

“I'm sorry darling, but I must ask. What exactly are you?”

She was intrigued all of a sudden about him. She had gone on adventures to many strange lands, and seen many strange things, but had never seen his species before.

“I am a human,” Anon said. “I am the only one of my kind. Turns out though that we are very culturally similar to ponies, so I've chosen to live here now.”

“Oh, I'm sorry to hear that.” Rarity said.

“Oh no, we're not extinct, I just got transported here from a different universe.” Anon replied in a nonchalant fashion.

“That's good to hear.”

“Yes, it's good to know they are still out there somewhere,” he pondered as he finished setting up the machine. Rarity watched with fascination, at how precisely and intricately he set up the machine. They had a dexterity which she had not seen from a creature without magic before.

“Wow you really know how to use your appendages don't you.” Rarity cooed at him.

“I wonder what else they would be good at?” Rarity drew up closer to Anon, a strange little smirk on her face.

“Well they certainly are useful. I can't imagine how I'd get anything done with hooves instead of hands.” he said, not really paying attention. He had finished the set up and was now longing for his bed.

“Maybe you could show me what else they are useful for later,” Rarity flirted.

“That's quite enough!” Sassy half shouted from behind the other two. She had been unusually quiet over the last few moments and Anon turned around to see that the mare had a deep scowl on her face.

“I'm sure Anon is tired and wants to go home.” She said in a more composed manner.

There was a short silence before Rarity picked the conversation back up.

“Oh, yes of course. The poor dear must be exhausted. Let's get you on your way.”

She got up and beckoned him towards the exit of the room. Anon stood fast though. There was still some unfinished business he needed to address.

“Um, excuse me Rarity,” he said as politely as possible. “I believe I'm due payment for my work.”

Rarity chuckled slightly. “Yes, I almost forgot! Go and wait out in the lobby and I'll get it for you.”

‘You did forget. Not almost’, he thought as he walked out of the lobby, happy that at least it was the right direction towards his bed. Unlike Anon, Rarity was switched on and alert. As soon as he passed through the doorway, a blue aura emanated from her horn. A pale blue magical sheet hung itself across the doorway, quickly becoming transparent as the spell was completed. His footsteps quickly fell silent as the sound proofing spell took effect.

Rarity swung round and started pacing around Sassy saddles. There was a devious grin on her face.

“Well well, that got you in a bit of a tizz didn't it darling. Rarity said with a silky sweet voice. “Did somepony get a bit jealous?”

“What! what are you trying to say?!” The blue mare retorted.

“You were certainly keen to put a stop to my polite and perfectly harmless conversation with Anon.”

“I think you might have a little bit of a crush do you not?” Rarity flicked her tail, and clipped Sassy on the end of her nose to punctuate her sentence. Sassy retorted back and blinked a few times. The flick didn't hurt, but it stunned her a bit. A deep red blush was forming on her face and was impossible to hide. Sassy knew the game was up.

“Okay maybe I do have a little bit of a crush.” She said sheepishly. She looked down at the floor. Her face burned with embarrassment as she tried to work out how Rarity knew. That mare really was the most socially aware pony in Equestria.

“How long did it take you to work it out?” Sassy said. She felt awkward and still couldn’t make eye contact.

“Soon as you walked in darling. You were walking so close to him you were practically leaning on his leg.” Rarity replied cheerfully. “I mean, I couldn't be sure, but my suspicions were aroused…”

‘Wow, was it really that obvious?’ Sassy thought. What if Anon knew? She would never live it down. He’d think she was a freak. It would be so humiliating.

‘No that's stupid’, she thought. Anon doesn't know, he's not psychic like Rarity is. She worked on her breathing and regaining her composure. Then she noticed something odd. It was quite literally staring her in the face. Rarity was sat across the room from her, looking at her with the biggest smile she had ever seen plastered across her face. Sassy really didn’t like where this was going.

“Why are you smiling?” Sassy questioned. “Don't you think I'm weird?”

“What? no, I think this is amazing!” Rarity replied. She clopped her hooves together in giddy excitement. Rarity really wanted to play matchmaker. It was sort of a hobby of hers, and this was just the opportunity she was hoping for. A friend with a silly schoolgirl crush just begging to be turned into something more.

“But he's a human! What will ponies think when they find out I like him? They'll think it's perverse. Oh Celestia, what will my parents think!” Sassy had begun to run away with herself.

“Interspecies relationships aren’t that uncommon dear, it's perfectly normal. I'm sure everypony would be happy for you,” Rarity reassured. She secretly admitted to herself that this was going to be a challenge, but that was good, she enjoyed a challenge.

“I hope you're right Rarity,” Sassy lamented. “Even so it's still just a dream. I've only known him a day! How the hell am I going to get him to like me?”

Sassy had realised how far out of our comfort zone she was. The mare had a hard time even liking new acquaintances platonically. Now all of a sudden, she had a stupid infectious crush on one. She had never felt this way before, and prided herself on being level-headed and stoic. That house of cards though, came crumbling down when it came to romance. She was a rookie, inexperienced and unsure. She needed a mentor, she thought. And she instantly knew who that could be. Sassy was staring right at her. Who in Equestria would give better advice than Rarity on dating and romance?

“Rarity, could you help me? I need your advice on how to do this,” Sassy said humbly.

She didn't often let the vulnerable side of her show, and admitting she wasn't good as something and needed help was extremely foreign to her. Rarity suddenly became very serious. She always knew when there was a need to be serious, and this was one of those times.

“Well you're speaking to the right pony for dating advice dear. What would you like to know?”

Rarity couldn't believe that Sassy was so timid when it came to romance, she was normally so confident and in control with other areas of her life. Being so unsure was most unlike her.

Sassy thought for a second before replying. “How do I get him to like me?”

Rarity snorted a little bit. “Darling, you can't get someone to like you. It’s his choice whether he likes you or not. In fact, he's probably already made it.” Rarity sat into a dog like sitting position as she carefully pondered her next words.

“What you can do, is be a mare he would want to like. I know you're that already, but there are some more things you can do. The first is looks, but you already look great, so let's focus on the second thing. Your attitude.” She wanted to say confidence, but it wasn't quite the correct term. She knew it was more nuanced than that, and wasn't going to dumb it down for her friend. It was possible to be overconfident, being aggressive and argumentative. It was a trap she could see Sassy easily falling into, so she had to explain this correctly.

All Stallions want a mare who is happy. Kindness and loyalty are all part of it, but a thirst for new experiences, and a playful outlook on life are just as important. Even being a little bit seductive helps. Rarity gave her a wink, demonstrating perfectly the playful attitude she was talking about. The concept was abstract, but Rarity thought she managed to do it justice.

Sassy pondered what Rarity had said. She thought it was good advice, and something she had thought about before. Being too serious or too nervous could indeed spoil her chances. Something was still bugging her though. Anon was not like other ponies, in fact he was not a pony. What if he liked other things in a partner, or just didn't date like ponies do.

“Rarity, you mentioned looks were the most important thing to a stallion, and whilst I’m flattered that you think I look great, what if he just isn't into ponies?” Rarity frowned and looked Sassy straight in the eye.

“Unfortunately, there's nothing you can do if that's the case. You just have to go and find that out.” It was an ugly truth, but Rarity thought it best to be said. There is no point sugar coating. Sassy meanwhile was pondering a question. One she probably should have asked to begin with.

“Okay, how do I find out if he likes me?” Sassy asked.

Rarity grew a sly grin.

“Why don't you just ask him darling?” she chimed.

Sassy's blush was renewed by that statement. There is no way she could ask a guy out! Besides, don't stallions find mares asking them out a bit weird?

“Seriously though Rarity, how do I find out if he likes me without it being so embarrassing. I mean what if he is weirded out, or disgusted.” Sassy asked in an authoritative tone.

Rarity knew exactly how to answer this question, being the seasoned seductress she was. She was delighted to pass some of her wisdom on to a friend in need.

“You need plausible deniability darling!” Rarity set in a sophisticated manner.

“What's that?” Sassy questioned. “I don't understand.”

“It means you don't have to ask him out in a way that could be embarrassing. Just put yourself in a situation where if he likes you, he'll do the asking. If not, he doesn't make any moves, and there's no embarrassment for anyone.”

Sassy look puzzled. “I'm sorry I still don't get it.”

Rarity tried to think of an example. There had to be an easier way to explain this.

“You know when you're at the end of a night out, and you're walking back with a guy you're interested in. Things may or may not be taking a lewd turn. You arrive outside the stallion’s house and he says, ‘hey do you want to come in for a coffee?’ No, of course you don't. Who the hell wants coffee at 3 am? What he is saying is, do you want things to continue? Without any humiliation for anybody. He's giving you and himself plausible deniability. So you can accept or decline without judgement. He can find out if you're interested, without saying ‘Hey! Wanna bang?’ I mean, even if you did it would be awkward right? You'd have to admit to it then and there, and you couldn’t back out of it if you changed your mind.” Rarity drew in breath as he finished what had become a bit of a rant. Putting nuanced interactions into words seem to be more difficult then she had previously thought.

Sassy was not familiar with the situation Rarity was describing. She was always too busy with work to go on many nights out, but she understood the concept Rarity was describing. It seemed a bit dishonest to her, but she couldn’t deny that Anon would have to make moves on her for this to work. Not the other way round.

“OK, I think I get it. It's more or less flirting right?” Sassy questioned.

“Yes,” Rarity replied. “But for more serious conversations.”

“I think we've kept him waiting long enough don't you. He'll be wondering what's taking so long. Go and get him!”

With an impressive display of magic, Rarity picked Sassy up and chucked her at the door. She slid through it, silently shattering the magical sound barrier, the pieces of which instantly disappeared into nothingness. Sassy Saddles slid to a halt in the lobby. Her legs splayed like a new-born giraffe, as she tried to keep her balance. She cursed Rarity for the unnecessary physicality, but quickly realised Anon was going to be nearby, so she put her efforts into composing herself as quickly as she could.

She looked around the room though, and found that he was not anywhere to be seen. She feared that five minutes may have been too long, and he had gotten annoyed and gone home. Then however, she heard a familiar sound coming from the opposite side of the room. She walked over to a chaise lounge facing away from her, and looked over the tall back. Anon was curled up fast asleep, snoring gently, the look of bliss on his face from resting for the first time in over 24 hours.