The cafe was a short trot away, and while it didn’t seem to take long in Sky’s eyes, Rainy would have sworn the journey took forever. While Sky walked ahead of her and told her some story that she paid no attention to, Rainy was transfixed by those two large, heavy orbs nestled between his hindlegs. They playfully bounced around in rhythm with his trotting and made Rainy’s mind wander to filthy but oh so fun places. Sky’s tail, which hid this beautiful sight from Rainy frequently, was swishing back and forth every few seconds, accompanied by an increased enthusiasm in his voice. Apparently the story he was telling her was exciting.

As they approached the cafe, Sky briskly turned around and made a grand sweeping gesture directed behind him.

“And with that we have reached our destination. So, where would you like to sit?” His grin faltered for a second when he noticed that she had spaced out again, but she quickly regained her composure and he forgot about it just as fast.

“Ummmm...anywhere is fine, as long as there is a good view” she said as she surveyed the cafe. It was a quaint place with multiple tables set up outside and a few ponies milling about searching for the optimal table to take up residence.

“Well,” he said motioning to a table toward the building where the cafe operated out of and where you could place a to-go order. “I always sit there when I can, is that table alright?”

With a quick glance at the table in question, Rainy gave a nod and started heading toward it.
As she took the lead, Sky happily got up and trotted behind her briefly. She was a really cute mare, not a very athletic build, but she still maintained a healthy and attractive figure. Her flanks had a curve to them that made Sky wish he had the courage to ask her out. It took all the willpower he could muster to simply get this far, but his good-hearted nature made this situation easier to handle.

As his eyes wandered across her plot he thought he saw a sliver of wet fur between her thighs, but surely it was just a few errant hairs or a trick of the light. Regardless of its cause, that mental image brought a stirring to his loins. Picking up the pace and coming alongside Rainy, Sky asked her if she had eaten here before. The purpose of his question being more to distract himself rather than actually ascertaining that knowledge.

She glanced over at him and said, “Not that I can remember, but it looks like a nice enough place” then took her seat at the table across from him.

Calling it a seat was a bit of an overstatement. Really they just sat around the table in the short trimmed grass that had a few patches missing here and there from hungry customers who were made to wait a bit too long.

On each table there was a nice pale yellow tablecloth with a vase sitting on top with sunflowers in it. Rainy took note of the establishment's name, “Sun-kissed Café” which was emblazoned in bright yellow letters above the threshold to the building. Each letter elegantly stylized and the dot on the I being a replica of our sun goddess’ cutie mark. It really was a nice place, as long as you were a fan of Celestia, but then again, who wasn't?

“So have you been here many times before?” Rainy asked with a pleasant smile.

“Oh, loads of times. Back when I was in school, my mom would take me here every Sunday. It was a little tradition of ours, and the food was good and reasonably priced. We haven't eaten here together in a few years though…” Trailing off, Sky looked sad for a moment, but quickly brought his smile back and looked at the mare across from him. “All things have to end sometime, I enjoyed it while it lasted.”

“Your mother sounds like a nice pony” Rainy said while hailing down a waiter.

“She is. Nicest pony I've ever met,” he said. “Present company excluded of course,” he added quickly before looked away with an awkward laugh.

Rainy’s wings fluttered lightly and she fixed him with a challenging stare. “Oh, is that so? You hardly know me. All you know is that I'm beautiful, aloof, and willing to accept free food.”

“I never said you were beautiful!”

“I thought you thought I was pretty,” she said with a little pout while feigning being hurt. “I guess I'm just an ugly mare you took pity on. And here I thought you liked me.” Her onslaught of teasing was having the desired effect.

“W-well I meant to say...that is...I do think you are pretty, but─”

“But I'm not your type, I understand,” she said, cutting him off with a slight smirk.

“No!” He said a bit too loudly, drawing the attention of multiple other guests. “Sorry,” he said to those around them before directing his attention back to her.

“Hello and welc- oh hey there Sky!” A chipper pale blue unicorn in an apron and levitating a clipboard and a few menus said as she approached. “Who's your friend?” She added with a wiggle of her eyebrows.

“H-hey Moonbeam. Uhh....R-rainy Day, meet Moonbeam. Moonbeam meet Rainy Day.” he glanced away from the waitress, avoiding eye contact at all costs. He nervously started counting the petals on the sunflower.

“You know Sky? He said he used to come here all the time” Rainy said, enjoying how cutely nervous Sky was being.

“Oh I know him very well. He has been coming here for a long time, and we dated briefly, but we work better as just friends.” She projected a genuine smile as Sky, who sheepishly returned one. “Wow, he must really like you, he's usually not this nervous. Well, I'll leave you be. I'm sure Sky is just dying to be alone with you again.” She grinned at him playfully, knowing that she was only serving to make a hard situation for him even harder.

As Moonbeam trotted away, Rainy cast a predatory glance at Sky who was too busy counting to notice. “So you do like me. Ha! I knew it. But should I give you a chance after calling me ugly?”

“I never called you ugly! I just─”

“Calm down. I'm only teasing.” she said with a giggle. “ So, how did you and Moony over there become an item?”

“I wouldn't say we were an item. We kinda just tried it out. We both hadn't been with anypony before and we trusted each other.” he retold, glancing back at the direction Moonbeam left. “She's really nice and a wonderful pony, but we are better being friends.”

“That's a nice story and all, but that doesn't really answer my question. There has to be more of a reason than just trust and being lonely. Come on, you can tell me. I bet I already know what it was,” she finished teasingly while she rubbed her hoof in little circles on the table.

“I don't think you do...it's, kinda personal,” he said, blushing and praying that the food would arrive soon.

“Mmmmmm, I bet it's very personal. I'd love to find out w─”

“Here we are,” Moonbeam interrupted, having returned with their meals. “A daffodil salad with extra extra ranch for the handsome stallion, and a daffodil salad with a sane amount of dressing for his lovely date.”

“She's not my date!” He said defensively with a betraying blush. “I mean, kinda...I'm just trying to be nice and─”

“Oh I think you are very nice.” Rainy interrupted, giving him a hungry look. “And other than calling me ugly, you have been a perfect gentlecolt.”

“But...I didn't...aughh!” A head slamming to a table could be heard all around the cafe as Sky gave up being right.

Moonbeam giggled and gently told Rainy to enjoy her meal before turning around and trotting to another table to take somepony’s order. Rainy glanced at her flanks as she walked away. She could certainly understand why Sky had wanted to rut that. She had full, attractive, and needy lips hidden behind her silky tail. Had Rainy been into mares she would have gotten very worked up thinking about them.

Finally, Sky raised his head and started eating his ranch soup quietly while Rainy ignored him. He gave a quiet sigh and cast his eyes into his plate.

“What's wrong?”

“Huhh…” Sky looked up to see Rainy looking slightly worried, her head cocked to the side and ears lowered.

“Is something wrong?” She asked genuinely.

Letting out a much louder sigh than before, Sky muttered something and went back to eating. Rainy couldn't hear what he said, so she got up and slowly made her way over to him, sitting down and draping a wing over his back. “I'm sorry I teased you so much. I often forget that some ponies don't take it well.”

As soon as he felt her pinions brush against his back he tensed up, but after a second or two he managed to relax, enjoying the softness of her feathers. “It's not so much that. I'm just tired of messing up. It seems like no matter how hard I try, I fuck up any chance with a nice mare I get.” He lamented as he stared at his half finished bowl of food.

Frowning, she hugged him closer. “I don't think you messed anything up. I think you have done great. Just look at what you managed to get before,” she said directing his attention to Moonbeam who was deftly balancing three plates on her back. “She's a real catch, but it's not your fault that you are better as friends.”

“It is my fault...like I said. I always fuck something up,” he said while running his hoof along the edge of his bowl dourly.

“Listen mopey, I think you have done an amazing job today. How about we go to your house so we can have a nice private conversation. We can talk some things out and get to know each other better. How does that sound.” Giving him a kind and warm smile, she really hoped he would say yes.

Author's Note

So Rainy Day's cutie mark is a watering can shaped like a cloud what has 3 raindrops coming out of it's spout. Sorry I can't draw, so in the story image she is a dirty blank flank.