The 1000+ Year Old Virgin

Much to Discord’s chagrin, Rainbow remembered the entire game of Truth or Dare. At least, she remembered swearing to get Discord laid. She apparently didn’t remember passing out on top of him and being carried home. When he told her about her throwing up, she was somewhat embarrassed, but quickly moved past it.

“Seriously though, I meant what I said,” she told him. “I’m your wingpony, I’m here for you!”

“I appreciate the offer, I can tell it comes from a place of sincerity, but it isn’t necessary,” Discord replied. “I am quite happily single. I know how much romance and intimacy means to ponies, but I don't need it.”

“You said that about friendship too, you know.”

He grimaced but was unable to argue with that. “Okay, let's say I humor you. Who would you even attempt to pair me up with?”

“I'm not sure yet, I need to know what kind of standards you have.”

“Standards.” Discord sank onto his couch. Rainbow was so committed to this that she had actually come to visit him in his dimension, which was such a thoughtful gesture that he was reluctant to actually make her leave. “So, like what traits I would look for in a potential partner?”

“Yeah, exactly! Heights? Mane colors? Intelligence? If you were to date someone, or even just sleep with them, what would they be like?”

“Hmm, let me think.” Discord stroked his beard and Rainbow waited patiently on the other end of the couch. After several moments, he said, “Understanding, trustworthy, a good listener, kind, intelligent, adventurous, optimistic, and funny!”

“You just described... a lot of ponies I know. We might need to narrow things down. Would you consider any of that to be, I don't know... more important? Like, is there anything that's a complete necessity?”

“Definitely understanding, you know what I was like in my past and I would want to be with somepony who won't hold a grudge against me for that. Who has taken the time to understand why I did what I did and sympathize. Obviously I don't expect total forgiveness if they don't want to give it, but it'd be nice to have some sympathy. That's all.”

“Ooh, yeah, I totally getcha.” Rainbow nodded. “Well, there's plenty of ponies out there who like you and know that you've changed for the better. Got anything else that's a must?”

“They need to have a sense of humor! I'm a very funny guy and I simply don't think I could handle being with somepony I can't get to laugh! There's nothing wrong with being a stoic of course but I wouldn't want to be with one.”

“Sense of humor, hm... oh, you know who's got a great sense of humor? Pinkie!”

Discord smirked. “Oh yes, I took a liking to her the moment I met her, I simply adore her optimism and jokes.”

“Soo, what do you say?” Rainbow sidled over closer to him, nudging his side. “Why not ask out Pinkie?”

“I don't know, I've never thought about her that way, would she even be interested?”

“She might. Who knows, she's unpredictable. But I think you and her could have a good time together, and who knows, it might even turn into something more!”

“And you'd be fine with us, er... dating? I've heard how awkward friend groups can get when two of them start dating.”

Rainbow shrugged. “Come on, we wouldn't let something like that ruin our friendship. If you and Pinkie hit it off I'll be happy for you, and I'm sure the others will be too! So, you're interested in hooking up with Pinkie?”

Discord sighed and got up, starting to pace. “I don't know. I still don't have much interest in this whole... sex thing. I've never had any desire to try it. Then again, like you said I wasn't interested in friendship either at first but then I found out how wonderful it was and now I wouldn't want to go without it. Do you...” He fiddled with his claws and gave Rainbow a curious look. “Do you think Pinkie would even be attracted to me?”

“Hah, probably! She likes funny guys like you, I'm sure if you asked her to mess around she'd be happy to! Pinkie is very sex positive and she'd probably sleep with anyone who asks. You have a good chance, don't worry.”

“You seem... rather familiar with Pinkie's sex life,” Discord replied with a suspicious look.

Rainbow chuckled, blushing slightly and pawing at the couch cushion with a hoof. “We've been friends for a long time, we can talk to each other about anything. And the topic has simply... come up a few times, that's all.”

“Have you slept with her?”

“Hey, this isn't about me, we're talking about you. Hooking up with Pinkie, yay or nay?”

Discord sat back down as he thought about it, then said, “You know what? Why not. If she's up for it, I'm willing to give it a try.”

“Alright! Think you can handle asking her by yourself, or do you want me there for emotional support?”

Discord snorted. “I think I can handle propositioning her on my own. Though, um... how does one go about asking, exactly? I get the feeling outright saying, 'Can we have sex?' would be rude.”

“Yeah, at the very least you wouldn't want to ask somepony that in public. No, a better way to ask would be to get her by herself, bring up the Truth or Dare game, and how the topic of your virginity came up. Kinda test the water, see what she thinks about that. Maybe you could make fun of me a little bit for trying to get you laid, but don't be too mean, okay?”

“Pft. Got it.”

“Then just casually say it got you curious about things and you want to try sleeping with somepony, and would she possibly be interested?”

“And that's not too forward?”

“Don't worry, she'll be fine with it. After that, if she says yes, then there you go! Have fun!”

“Sounds simple enough. Very well, I'll go talk to Pinkie.” Discord stood, and Rainbow hopped up too.

“Alright, but before you go, one little tip. She's really kinky so ya know, be prepared for that.”

“Kinky? Hm. Kinky Pinkie. Kinky Pie!”

Rainbow groaned. “Yeah, she hasn't made that joke a million times...” She flew behind him and began pushing him, wings going full speed yet only managing to move him like an inch. But that didn't stop her from trying. “Okay, let's not waste any time, I want you to have a good time and then I want a full report on how good it was!”

Discord snapped his fingers, teleporting them to Sugarcube Corner. Then he took a step to the side and watched her fly past him. She shouted with alarm and quickly flapped backward, managing to stop just before she hit the wall.

“Good morning, Rainbow!” Pinkie called from the counter. “And good morning, Discord!”

“Good morning, my lovely pink friend!” Discord said cheerfully, going over to greet her. “How are you doing?”

“Great! That was some party last night, huh?”

“Indeed, I'm surprised you didn't take today off.”

“I thought about it, but I just love selling my treats so much, I couldn't stay away. Things are kinda slow today, though.” Pinkie gestured to the empty store.

“Ah, that's too bad.”

Rainbow hovered over to Discord and whispered in his ear, “I'm gonna head out. But good luck!”

He nodded and she left, and Pinkie tilted her head curiously. “So, what's up with you?”

“Nothing much. I was just hanging out with Rainbow, making sure she's okay after yesterday, haha. But she's right as rain, as you can see.”

“That's good! Yeah, she drinks way too much, I think she's picking up some bad habits from the Wonderbolts. Something about the military being full of alcoholics? Anyway.” Pinkie twirled around some of the lollipops in a nearby jar. “I'm not even hungover, the secret is to stay hydrated and make sure you eat something, you shouldn't drink on an empty stomach!”

“You're so right. Speaking of the party, remember that little conversation that came up toward the end of Truth or Dare?”

“About you being a thousand plus year old virgin?”

“Yes, that's the one.”

“Sure do! I wonder why Rainbow fixated on that so much, it's nopony's business if you are or aren't a virgin, it doesn't really matter.”

“Right? Rainbow can be so pushy, she actually came to my house this morning to keep talking to me about it, can you believe that?”

“Haha, yeah, she's pretty stubborn.”

“But I have to admit, it kind of got me thinking that maybe I should try sleeping with somepony.”

“If that's what you wanna do, then go for it! It really is fun!”

“Oh, I am going for it.” Discord rested his hands on the counter and leaned forward, swaying his hips slightly. “Would you be interested in showing me the ropes?”

“Would I... oh!” She blushed, pressing a hoof to her chest. “Why, Discord, you want to mess around with me?”

“Well, sure! Who better for my first time than a sweet, fun-loving mare like yourself?”

“Aw, you big flirt.” She waved her hoof, grinning. “Well I'm always up for helping out my friends, so yeah! I'll sleep with you! Aw, this is just so cute, that out of anypony you could have come to, you come to me.”

“Well, if I'm being honest, Rainbow put me up to it. I said I would want somepony with a sense of humor and you were the first person she thought of. And I've always liked you, I mean even back when I first met you and wasn't exactly a good guy, well...” Discord chuckled and ruffled his mane. “I admired your personality, how you were always smiling, and... yes.”

Pinkie beamed. “I'm happy to hear that! I gotta finish up my shift, but how about you meet me back here at 3 PM and we can get to it?”

“Sounds good, I'll see you then.” Discord headed out, sighing with relief. That went well. Now he just had to wait until 3 PM and-

“Discord!” Rainbow tackled him from the sky, and taken by surprise, it sent him sprawling.

“I didn't order this rainbow-colored missile,” he said indignantly, pushing his face out of the dirt and spitting.

“Oops, sorry, I didn't think that'd actually knock you over.” Rainbow helped him up and grasped his paw. “So, how'd it go?”

“She said yes, so I guess it went well,” Discord replied, pulling his paw back and making a show of wiping himself off.

“Okay, I get it, sorry.” She awkwardly helped brush blades of grass off him. “But that's great! Am I a great wingpony or what?”

“Define great.” Discord walked past her. “Can you leave me alone about my sexual status now?”

“No way, dude, not yet! I can't just let you go in blind! Pinkie's got loads of experience and you've got none, I need to give you some advice.”

Discord sighed, rubbing his face. “I can't imagine it's that complicated.”

“Not really, but still. Come on, let the Dash teach you everything you need to know.”

Discord scowled, but he supposed he had nothing better to do. So he let the overenthusiastic pegasus drag him off, already planning out how he was going to get her back for all this.

“Okay, so what do you actually know about having sex?” Rainbow asked.

Across the table from her, Discord rolled his eyes and took a sip of tea. Eh, not as good as Fluttershy's but it'll do. “Honestly, you're acting as if I'm a foal. I completely understand how sex works, it's pretty simple. Sexual reproduction in ponies involves the male penetrating the female and moving inside her until the stimulation causes ejaculation, at which point his sperm is able to potentially fertilize one of her eggs, and in the case of fertilization, after around eleven months she will give birth to a foal, though in rare cases twins are born. Though of course any gender can have sex with each other and how that happens depends on the respective genitals involved. Now would you like me to go into detail on cellular meiosis and the step by step process of a zygote turning into a foal or you satisfied with my knowledge?”

Rainbow's face turned red. “Uh, well, you clearly know a lot about it from a... biology standpoint.”

“Yes, I've read several biology books and learned about the reproductive systems of countless different creatures. I could also tell you about the circulatory system, respiratory system, nervous system-”

“Okay, I get it, you're an egghead. But while knowing the physical stuff is good, there's more to it. You gotta listen to what your partner wants, move with a good rhythm, really pay attention to their body. Don't be afraid to nibble their ears, dirty talk to them, stroke their thighs... let them know you're enjoying it and that'll make it even better for them.”

Discord summoned a notebook with a snap of his fingers and started writing in it. “Mhm, nibbling, talk dirty, thighs...”

“Pinkie likes kisses,” Rainbow mused. “So if you're comfortable doing it, you should kiss her.”

“Kisses... okay, admit it, you've fucked Pinkie haven't you?”

Rainbow stared, then laughed and looked away. “Haha, no, what makes you think that?”

“I can tell you're lying, every time you lie your second to last primary feathers twitch.”

She sighed and looked back at him. “Okay, fine, I have slept with Pinkie.”

“See, was that so hard? Also, your feathers don't twitch, I just said that to get you to confess.”

“You're a dick.”

“Thank you. What else do I need to know, oh guru of lovemaking?”

“Really you should just kinda go with your instincts, but don't forget about foreplay! Spend some time really getting to know your partner, find out what makes them tick, get them turned on and desperate for you. Try going down on her, she'll love that.”

“Going down on her?”

“Oral.”

“Ah.” Just how many sexual euphemisms did ponies have? Discord felt like he needed a dictionary to keep track of all these terms.

Rainbow smirked. “With that tongue of yours I'm sure she'll love it. Just try not to bite her, that fang probably wouldn't feel too good.”

Discord idly rubbed his fang. “Hmph. Noted.” He finished off his tea and gestured between them. “Is this normal? Like. Do pony friends usually talk about how to get each other off?”

“You'd be surprised. Alcohol helps, true, but when you're comfortable enough with somepony you can talk sex completely sober!”

“I see. Okay, well, I appreciate your advice and I'll certainly let you know how things go.”

“Cool.” Rainbow stood. “Well, I guess I should get ready for my drill practice with the Wonderbolts.”

“Oh, I should leave you to it.” Discord passed his cup over to her and stood too. “Have fun, and make sure you do your warm up and cool down stretches!”

“Haha, of course. See ya later.”

Discord teleported from her house. A few hours of relaxation and then he can go meet up with Pinkie. He really hoped it lived up to the hype, otherwise he was going to have some serious words for a certain pushy blue pegasus.