BONUS: Speed Dating Extended Edition

Granny Smith hobbled over to your table on her walker. You silently prayed to whatever higher power may have been listening that she was just coming over for a friendly chat.

"Well, hello there, handsome," she said, flirtatiously smiling. Whatever higher power had been listening to you is a fucking dick.

"Hey, Granny Smith," you replied awkwardly. You sent out one last prayer to that dickhead deity that Granny was just being overly friendly. "What brings you out, tonight?"

"Well, I heard you were puttin' yerself on the market," she said, closing the distance between you, every single joint in her withered, old body creaking louder than every rusty door hinge in every universe. "And I figured I would be remiss if I didn't try fer a shot at ya."

"You don't think I'm a bit too young for you?"

"Oh, pish posh," Granny replied, waving a hoof, dismissively. "I've never had an issue with May-December relationships. Shoot, just ask Thunderlane and that strange Doctor feller about me, and they'll tell you many great tales about our nights o' passion. They've even told quite a few o' their friends about me, and they've come to sample some o' my pie, to see if it's just as good as they were told."

Granny Smith, Ponyville's favorite grandmother, whom you had spent many afternoons in her company, drinking lemonade and eating some of the best chocolate chip cookies you had ever tasted, was a very popular and active GILF. You really didn't know what to think about this. You briefly pondered what it would feel like if she took those dentures out and went to town. The thought made you shiver, but you didn't know if it was from revulsion or excitement.

"I-I'll consider it," you stammered, trying to politely end this conversation.

Granny Smith smiled, rising from the table. "Don't take too long, now," she said, turning towards the door. "I got me quite the waiting list of kind gentlecolts lookin' to spend some time with me, but you get front o' the line privileges whenever you want.

"G-good to know," you said, waving good-bye to the sexually active senior.

You could never look at Thunderlane or Doctor Whooves the same way, again, and you didn't know how many other stallions shared that distinction.

...

"I, uh, didn't know there were any other draconequuses, besides Discord," you said, staring incredulously at the female Spirit of Chaos seated across from you. You had to admit, there was something quite appealing about the way she looked, like a sexy, mismatched snake.

"Oh, please," said an all too familiar male voice. "Did you think he just appeared out of nowhere? He had to have been born from some lovely mother."

"Discord," you growled. "I know that's you."

"Discord?" the draconequus feigned innocence. "What are you talking about? My name is Eris, and I'm clearly a very sexy woman."

"Discord," you repeated, growing slightly angry. "I might have fallen for this, if you had bothered to change your voice."

"Oh, fine," the Spirit of Chaos sighed, crossing his (her?) arms in defeat. "If the voice is a problem, I can change it."

"Go," you said, pinching the bridge of your nose. "Just go." A snap and a poof later, and the seat across from you was empty. You turned to Lyra. "I thought I told you to tell all the guys to go home."

"Well, I did," Lyra replied, defensively. "But when I said that, he just poofed himself into a girl's body, so i figured it would be okay."

"God dammit, Lyra..." you muttered.

...

Rarity's mom, Cookie Crumbles sat across from you, smiling.

"Uh, aren't you married?" you asked, apprehensively.

"Oh, don't you worry about that," the MILF replied, one of her hind legs slowly making its way up your calf. "My husband and I are in a- oh, how do you say it? Open relationship. He gets to sleep with whatever mares he likes and I get to do the same with stallions," she said, her hoof now making its way dangerously close to your crotch. "So, I heard you had one of my magazines?" she whispered, moving close enough to you that her lips nearly touched your own.

"I HAVE TO GO TO THE BATHROOM!" you shouted, blushing, and quickly dashing to the nearest restroom.

...

"I mutht thay," Twist said, sitting down at your table. "I find the prothpect of dating an older thtallion quite ekthiting."

"No," you said, bluntly. "Just no."

Tears began to form in the young filly's eyes, before she took off at a gallop, loudly crying.

Great, now you felt like a complete asshole for making a child cry.

...

For the love of God, please, shut the hell up, you thought for what felt like the twentieth time in five minutes. Trixie had joined you at your table and immediately started droning on about how she was clearly the most perfect mare in all of Equestria, so you should obviously date her. Honestly, the only reason you hadn't told her to go away was because you didn't think she was even listening.

You looked over at Lyra and Bon Bon, silently pleading for help. "I'm going to go get Starlight," Bon Bon said, understanding exactly what you were trying to convey.

"Thank you," you mouthed to her, while Trixie continued to ramble about her expectations of you in the bedroom.

...

"So, uh," you began, unsure of whether or not what you were about to ask was rude. "Are you a mare or a stallion?"

The changeling across from you looked back at you through half-lidded eyes, a small smirk etched across its face. "Baby, I can be whatever you want."

For the first time tonight, one of your dates wasn't a hard "no" and was a definite "maybe".

...

Luna was back, this time visibly drunk, with half a bottle of rum clenched so tightly in her magic that cracks were beginning to form in the bottle's neck. Her sister, Princess Celestia, was also present, comfortingly holding her distraught baby sister and stroking her mane, while intensely glaring at you.

"B'why?!" Luna slurred and sobbed, chugging down three more gulps of liquor, as she continued to add to the sizeable puddle of tears on the table. "Minawgudinuff?"

"I-I'm sorry..." you stammered, trying to figure out what Luna was trying to tell you.

Celestia continued to glare at you. "I should send you to the moon for what you have done to my sister."

Author's Note

Randomly thought of Granny Smith being a total silver fox and thought it would be funny to include it in the speed dating segment. That quickly spiraled out into this. May do more, if inspiration strikes.