The Age Old Question

by NinjaMare

Rating: mature
Tags: Main 6, Anon, My Little Pony: Friendship is Magic, Comedy, Rarity, Other, Sex, Twilight Sparkle, Random, Slice of Life, Human
Length: 7295

Anon is about to have his first go of having sex with pony, question is, how will it go for him? and his chosen partner?

Here is a question that all human's face if they get stranded on Equestria: would you have romantic or even sexual relations with a pony, or not? and would you ever consider pairing up with ponies? some would say no to this question, some would say yes, some might even say "Might as well, ain't no other humans to hook up with. and I rather not die alone". so let's see how Anon handles this question.

Published 2021-06-14 15:50:01 UTC
Last updated 2021-06-14 15:50:01 UTC

Do I or Not Hook Up With A Mare? [Edited]

Ponyville, a quaint little town just a few miles away from the capital city of Canterlot, and is home to the Castle of Friendship where Equestria’s fourth princess lives. Now in the past three years this town has seen its fair share of weird, crazy, and down right out of this world events take place. From Nightmare Moon’s return, to having Discord just screwing with everything, the birth of a new alicorn princess, having an ancient magic absorbing tyrant trample about. Seriously at this point the ponies of the town should just label Ponyville as the ‘Great Magnet for Weirdness’ place there is in Equestria, especially with its latest bizarre outcome.

In the Castle of Friendship all was peaceful, quiet, and rudimentarily calm and tranquil. At least for Anon that is. It’s roughly been about six months since Anon came to Equestria, not intentionally mind you, and so far things have been rather nice. The ponies are a generally nice people, ignorant and a bit childish—adults greatly so—and can be incredibly naïve and a little overly trusting, but overall nice people. And given on how ponies seem to have their entire country under their hoof, Anon guesses that’s why they are so easy going and somewhat dim in some regards.

For the first few months things were nice, but after that Anon started to wish he could go back home as Equestria was starting to lose its charm, which isn’t help by the short span of having various bad guys trying to either take over the country, or just one crazy adventure that should be in a comic book that Anon somehow gets dragged into. Really, all he wants is just to have a nice quite life which he had back on earth.

At the moment the human was currently inside the castle’s library and peacefully reading the third instalment to the Daring Doo Adventure Stories, which to him are just pony adaptations of the Indiana Jones series. But the pony elements give a few nice changes to make them at least interesting enough to keep reading them. but their still fairly predictable books. He wasn’t sure why Rainbow Dash was adamant that this series, by her, is the greatest thing ever written when there are many other book series just as good, or even better. Then again the mare is not exactly the most, book learnt pony there is—in fact Anon doubts that Rainbow Dash reads anything aside from the Daring Do series.

“Alright I am done with this book.” Anon grumbled as he closes the book and just let it slide from his hand onto the floor, while he stretches out on the long couch a moment later before just laying on the furniture like a limp noodle.

“God I didn’t think I’d miss my video games, TV, or anything from home this much.” Anon annoyedly muttered as he swung his legs off the couches arm and onto the floor while he gets into a sitting position.

“Really wish my house, and everything in it, got teleported to this damn planet along with me.” Hopping off the couch Anon then walked out of the castles library, and just started to wander around the crystal castle mostly just trying to figure out what to do. As Anon continued his aimless wandering, and his reminiscing about the way his life has been going lately, the human had passed by the other two occupants of the castle just going about their day.

Spike as per usual was just wandering around the castle cleaning every nook and cranny there is, which to Anon seemed like a tortuous task. After all, an entire castle that is nearly ten or so stories tall all has to get cleaned, by a three foot tall pudgy dragon with no help from an actual cleaning staff, or just an ordinary staff for that matter to help out. But it’s none of Anon’s concerns if the princess of friendship wants to endorse child labor, and Spike was fine with it, then who was he to question their decisions.

Then there was Starlight Glimmer who Anon calls Twilight Sparkle Mark. 1½. This mare is a pure mental case just waiting to happen since Anon has known her. after all she went as far as to distort the timeline of the entire planet to conform to her hatred on cutie marks, all because a kid she knew when she was a brat was whisked away to a fancy school, who she never bothered to write or even visit to stay in contact. Then there are the various ridiculous ‘friendship lessons’ that Twilight gives the mare, and somehow blows them out of proportion like brainwashing himself and Twilight’s friends all for the purpose to learn about them, while only doing everything she says with no objections. Anon tries to stay clear of her as much as he can, so nothing like that or other incidents like it will ever happen again.

“I think what I really need is to get my own place.” Anon said as his mind shifted from past events to more personal situations after crossing Starlight in the third lobby practicing magic.

“That way I won’t risk having Starlight go off when she has one of her moments. Or Twilight for that matter.” Speaking of said alicorn Anon stumbled upon her, and her friend Fluttershy, when he unintentionally entered the kitchen while he was just wandering.

“Hi Anon.” both mares said cheerfully to the young man.

“Hey.” Anon simply said as he strolls past them, and started to rummage through the fridge.

When Anon first came to Equestria he was really skeptical of the brightly colored ponies, but they were quick to show the young man that they are no threat to him. all except Rainbow when she threated to beat his ass back into the Everfree Forest when she thought he was some kind of monkey monster, but thankfully Twilight and the others weren’t as judgmental or hostile as the pegasus. although that doesn’t mean that they were slightly better company. The alicorn and her friends along with the town as a whole, were so welcoming to strangers and so happy-go-lucky, that Anon thought that they might be setting him up for something horrible. Fortunately that prospect never came true, but Anon now tries to avoids any party that Pinkie Pie throw. That mare just gives Anon some uncomfortable vibes.

“So Anon, have you thought about what I asked?” Anon heard Fluttershy ask him as he felt the pegasus brush up against his leg, Anon looked down towards the mare as he grabbed a bottle of soda.

“For the last time Fluttershy: I’m not interested. If you want someone to give you a good plowing, then go find some stallion.” Anon quickly retorted before taking a sip of his soda, but Fluttershy quickly respond to the human’s statement while propping herself up on her hind legs, and leaned onto Anon’s side.

“But there aren’t any single stallions in Ponyville.” the pegasus mulled as Anon felt her start to caress a hoof over his stomach, which he quickly stopped by gently pushing the mare off himself.

“Not my problem.” Anon restated as he walks around the pegasus. “Also I doubt we’d be compatible partners even if I decided to accept your offer for free sex.”

“Why’s that?” Anon heard Twilight ask before he left the kitchen entirely.

“Because I know that pony sex and human sex are two different things, and that you mares wouldn’t be able to handle anything else than a stallion and your vanilla hot nights.” With that Anon fully left the kitchen and the two mares behind, and continued to just wander around aimlessly until something finally pops into his head, or catches his attention to cure his boredom.

The young man’s aimless walking about eventually lead him to the castles main entrance, and after finishing his soda and effortlessly tossing it into a nearby trash bin the human left the castle, venturing out to the town in the search to curve his excessive free time. Now aside from Twilight and her circle of friends the rest of the ponies of Ponyville don’t really mingle with Anon, but it isn’t out of fear or xenophobia. It mostly stems from that the ponies aren’t sure how to interact with the human, and it doesn’t help that Anon is a rather reclusive individual and doesn’t bother trying to get to know any pony else. Which to Twilight and her friends means that Anon must’ve had a hard time making friends back home, which Anon had rebuked as false. He just likes his privacy and a quiet life style more than being around other people, but there is another reason why Anon prefers his solitude than being with other ponies.

“Oh Anon~.” Anon paused as the sing-song voice of a pony called out to him. looking to where the voice came from he found another member of Twilight’s circle of friends trotting over to him, with some bags floating beside her.

“Hey there Rarity.” Anon said in a polite tone. Now Rarity was a mare that Anon was generally on good terms with, mostly because she was the only pony in town that he could have a normal conversation with when he decides to mingle, as well as provide new clothes for him. If he ever needed them. But there were times when her overzealous drama queen act and complaining becomes grading, and how she can be very snooty at times. Thankfully, these moments don’t last long.

“What brings you out of the castle today dear?” the mare asked as she brushes up against the young man’s leg like a cat. Anon was not really put off by the mare’s affectionate hello, as all ponies are pretty physical with their displays of affection since they literally wear their emotions on their sleeves.

“Just trying to find something to cure my boredom mostly.” Anon said as he took a step away from the mare. “And what about you? what are you up to today?”

“Oh just shopping for a few projects, and orders that I need to get done. Nothing out of the usual.” Rarity said as she brushed a bit of her mane out of her face.

“Oh! Speaking of which, I have the new sets of clothes that you requested. There in my shop ready to be picked up, come along!” With that the mare trotted off towards her shop, with Anon following behind her.

As the two made their way to Rarity’s abode Anon just looked around indiscriminately, still trying to figure out what he should do for the day after getting his new clothes, and dropping them off back at the castle. During the walk Anon’s wandering eyes fell upon Rarity, who was trotting with a saunter in her gait which caused her fairly shaped rump to jiggle. And giving the young man a clean view of her ponut and pussy, a sight he’s been fairly used to since coming to Equestria. To Anon the sight of a mare’s genitals had at first been somewhat off putting, but after seeing them multiple times over the months and noting that they weren’t so different from a human woman’s own junk, except being a bit more plumper and darker in coloration, he wasn’t to bothered by them anymore.

Looking away from the unicorns exposed honey pot Anon spotted Carousel Boutique just ahead of him and Rarity, and in no time the pair was at the door. Entering the boutique the pair started to make their way up to Rarity’s room, where upon reaching the room Rarity trotted over to the main desk at the end of the room while Anon just stood by her bed, and watched the mare place the bags she was carrying down off to the side and then picked up the lone bag on the desk.

“Here you go Anon, four new shirts, boxers, and pants. And eight socks.”

“Thanks Rarity.” Anon said as he took the bag.

“See you later then Rare’s, I’ll let you know when I need more clothes, or need them to be repaired.” The human then turned on his heel and started to make his way out of the room, but was stopped when the unicorn spoke up.

“Anon wait!” he did so and glanced over his shoulder to look at the mare, who seemed to be blushing slightly.

“I’ve been meaning to ask you this for some time now, as I wasn’t sure if you would be open to the idea, but now…” the mare hesitated for bit before looking up to Anon as she approached him. “Would you possibly consider going on a date with me?”

“You wanna go on a date with me?” Anon questioned as he turned to face Rarity fully. “Why?” he simply asked as he looked down at the mare.

“Well I always thought that you and I had some kind of connection.” Rarity said as she stood a foot from Anon.

“Whenever we hang out with the others, either at a party, or a little get-together, you always seem to talk to me more than the others. I, assumed that means that you like me. Am I wrong in that assumption?”

“Well you’re not wrong in assuming I do like you more than the others Rarity.” Anon admitted as he rubbed the back of his neck.

“But it’s not anything romantic, it’s mostly because I know that I can have a pleasant, and calm talk with you. With Rainbow and Applejack it’s either competitions, testing to see how tough I am and all that. Pinkie just rambles and talks like she’s playing a thousand questions and says things that I just can’t keep up with. Twilight and Fluttershy are alright, they just like asking a lot of questions, some more personal than I would like.”

“Oh. I see.” Rarity says in a disappointed tone. Anon gives a small sigh as he crouches down to a kneeling position.

“But if you still want to go on a date, we still can. It’ll just be as friends.” Rarity seemed to have perked up at that notion as her tail wagged in joy. Anon always found it adorable how dog like the ponies could be when their happy.

“I’d appreciate it Anon.”

The mare then hopped up and gave Anon a hug, which Anon returned by a more simpler hug and pat on the back. after agreeing to going on a date sometime next week, Anon bid the unicorn farewell and left the boutique to take his clothes back to the castle.

After walking through the town for about five or so minutes the young man made it back to the castle, and proceeded to head to his room. along the way Anon spied Spike still hard at work, cleaning and scrubbing the castle. He also spotted Starlight still at work in practicing magic, as for Twilight Anon didn’t see her along his path towards his room, she was probably somewhere else in the castle with Fluttershy or alone somewhere. Or she probably left the castle. Either way it didn’t matter to much to the human, though that sentiment changed when Anon bumped into Twilight coming down the hall and causing her to drop a few books, some scrolls, and splatter ink from their container on the floor.

“Sorry didn’t see where I was going.” The alicorn apologized as she re-collected her stuff.

“It’s fine Twilight. But maybe you should keep your nose out of a book, at least while walking so you could see where you are going.” Anon said as he smooths out his pant legs. “But what’s got you in such a rush?”

“I was just getting ready to study a topic that I was hoping to get your assistance in.”

“My assistance in what exactly?” Anon questioned as he crossed his arms.

“I wanted to know what the difference between pony courtship and sexual activities in relation to what human courtship and sexual activities were like.”

“You, what?” Anon asked in confusion.

“Ever since you told Fluttershy that both our species are too different for intimate relationship, and that we mares could only handle intercourse with a stallion, I’ve been curious as to just how different our two races are when it comes to sexual intercourse.”

“So basically you want a sex ed lesson from me.”

“That and maybe documentation of said sex ed.”

“What do you mean by document.” The alicorns face turned a nice shade of red as Anon asked her, which caused Anon to raise an eyebrow as he eyeballed the princess. “Twilight?”

“Well, for the best results, as well as data I thought having hoof’s on experience would be the best source.” Twilight nervously explained as she wiggled in place while Anon still kept looking down at her with scrutiny.

“And pray tell, how are you going to get this ‘hooves on’ experience information.” Anon questioned with air quotation marks but the mare only blushed more heavily.

“…I was hoping that maybe, possibly, we could…” Anon just shook his head as he gives a tired sigh.

“Twilight if I said no to having sex with Fluttershy, what makes you think I would with you?”

“Well…I was…that is…because—” Anon was about to say something to end this, but it seemed Twilight had come up with a response before he could even utter a word.

“Because what if you find yourself a marefriend!” the alicorn quickly blurted out before going into one of her favorite pass times: deep and sometimes longwinded explanation.

“Think about it Anon. You don’t want to be alone for the rest of your life, what happens when a mare shows interest in you, and you do so in return? You’d want to make her happy right? and you’d also would like it if she made you happy right?”

“Right?” Anon said skeptically.

“Well forming a romantic relationship would be easy, but what about when the two of you have your, needs?” Twilight continued.

“I think the reason why you keep saying no to Fluttershy, or any mare that ask’s for a simple roll in the hay, is because you’re unsure if you can please a mare with what you know about sex.” The alicorn really wasn’t too far off the mark for Anon.

He’s had his fair share of sex back home, mostly unintentional, but here in Equestria Anon has a vague idea on how pony sex is like from what he knows of horses from Earth, as well as read a few anatomy and biology books on Pony physiology when he was bored. Plus the few times he’s stumbled upon a young couple deciding to have public outdoor sex, all of which were very awkward, but all-in-all they all seem to end the same. Stallion mounts mare from behind, and just thrust till he empties his balls into her. So it’s hard to say on how sex with a mare for him would go, especially since ponies are only half his overall size, there’s even the prospect if the techniques and tricks he knows would even work for ponies. And Twilight does have a point. Since Anon is virtually stuck in Equestria, that doesn’t mean he wants to be a single guy for the rest of his life. He may like his privacy, but being partnerless, and self-free time are to different things.

“You may have a good point there Twilight.” Anon eventually said after a beat of silence that followed after Twilight’s little improv way of explaining her reason for hooves on experience, and Anon thinking the whole thing over.

“To be honest I really was afraid that I might screw something up if me, and whatever mare I hook up with, eventually decide to have sex would go horribly wrong in a very awkward inter-species bout of sexual combat.” Anon said with a little bit of a joking tone in his voice, which did get a bashful chortle from the alicorn.

“But how will we go about this. I mean it’s not like you were just planning on having us head to your room, and just go at it blindly right?” Twilight went silent after Anon just rambled and seemed to be both astonished, and a little worried. Which prompted Anon to give the mare a quizzical look.

“I just guessed your plan, didn’t I?”

“…yes.” Twilight admitted solemnly. Anon just rubbed his face with a hand before speaking up.

“Well then, let me just drop the new clothes I got from Rarity, and I’ll meet you in your room for this ‘experiment’.”

The moment that Anon stated that he would indulge Twilight’s little experiment, the mare perked right up and started to prance in place in excitement. Which was both cute to watch, yet silly at the same time that this mare is acting like a child getting their Christmas present. After the agreement was made Twilight rushed off towards her room where she said she would get things ready, while Anon continued on to his room to drop off his clothes.

~~~~~

After Anon had dropped his clothes off in his room, he started to make his way towards Twilight’s room which was on the other side of the castle, and after a few minutes of walking through hallways and climbing a few stairways Anon reached the wing of the castle that Twilight resides in. reaching the princess’s door Anon gave it a few rhythmic knocks, but after the young man gave the door the third musical knock the doors practically shot open. And on the other side was a really excited looking Twilight Sparkle.

“Anon come on in!” the alicorn ushered as she tried to literally push Anon into the room.

“Geez Twilight calm down.” Anon said as he sidelines the mare, nearly causing her to fall forward while he walks into the room. “Your acting like a starving virgin who can’t wait to turn in their v-card.”

“Well I guess I am a little too excited for my first time.”

“Whoa wait!” Anon said as he turned to look at the alicorn with a look of surprised etched onto his face.

“Twilight you’re a virgin?” the mare then blushed as she nervously nodded her head.

“Since I never really socialized until two years ago, I never got a chance to really get to know any stallions. Even when I moved to Ponyville I was still wrapped up in my studies into the Magic of Friendship, that I still never got a chance to interact with stallions. Doesn’t help that most stallions are already spoken for.”

“What about that jelly obsessed stallion?” Anon questions.

“No he also has a partner, and she’s just as into jellies as he is.” Twilight admitted as she trotted over to the bed.

“Wow. So I guess I really am the only single guy in this town huh.” Again Twilight confirmed Anon’s assumption with a nod.

“So Anon, how do you want to do this?” Anon heard Twilight say in a slightly nervous yet excited tone.

When Anon looked at her he could see that Twilight looked like she was ready to pop a gasket because of how red hot she looked, hell, Anon could swear he’s seeing steam wafting off her. Anon approached the mare and dropped to one knee where he placed a hand on her head, causing the mare to jerk.

“Firstly you REALLY need to relax Twilight. You look like your about to pass out from heatstroke.” The mare tried to calm herself down from the heated anticipation of the evenings oncoming event.

“Sorry. It’s just I’m nervous about doing this.” Twilight stuttered as she clenched her hind legs while her tail swishes about.

“I understand that. So why don’t we try something simple before we get into the real thing, alright?” Anon suggested as he remained kneeled in front of the mare.

“Alright. But what do we do first?” the mare asked as she looked up to the human with a great deal of anticipation shimmering in her eyes.

“This will be a good way to start.”

Anon scooted in closer to Twilight and gave her cheek a gentle caress, a good old fashion loving way would be the best way to start this little tryst more so for Twilight than Anon, as the former probably has little or no experience in this field. After giving the mare a pleasant pet Anon then leaned in and gave Twilight a kiss on the lips, which the alicorn pushed into with great fever in making a sweet little kiss, into a more passionate one. Or at least the alicorn tried. Her attempt was a bit sloppy, but Anon had to give her credit in being so bold. But the interaction was short lived as the lavender pony quickly pulled away.

“I’m sorry Anon I didn’t mean to go that far, it’s just that—” the young man ceased Twilight’s pre-ramble by placing a finger on her lips.

“It’s fine Twilight. Honestly, I’m surprised that you would actually be so bold in trying to deep kiss me.” Anon said with a bit of mirth in his voice as he gives an amused look towards the mare, who just blushed even redder.

“I’ve read that it’s the best way to show a stallion that your greatly interested in courting them, and wanting to, you know, have sex.”

“Well that’s one way to get your point across.” Anon mused with a small chortle as his initial expectation of the afternoons events would go.

After the little pause in the make out session Anon stood up and guided Twilight to her bed, where the two will continue their little experiment more comfortably rather than standing, and kneeling, on the floor. Once the pair were on the bed Twilight surprised Anon by initiating the next make-out session. As they locked lips the two participants started to angle their heads so that their make-out was more comfortable, and while Anon was an old pro to make-out sessions he had to admit that kissing Twilight was certainly a new sensation for him. while her muzzle wasn’t too long in comparison to women he’s had relations with before, overall small size of her mouth was a bit unusual as it narrowed a little more than what a humans mouth would be. A few minutes more of kissing each other the pair eventually broke their lip-lock, with Twilight looking very winded while Anon looked pleasantly surprised by the experience.

“Wow.” Twilight huffed and puffed as she tried to catch her breath.

“You’re a really good kisser.”

“You’re not too bad yourself.” Anon complimented. “So, what do you wanna do next?”

“W-why are you asking me!?” Twilight said nervously as her wings and feathers ruffled.

“Well this is supposed to be Your experiment, I just got things started. Now it’s up to you on where to take it.” Anon said as he leaned back slightly giving the mare some time to think about what to do next. As the mare thought her tail lazily thumped against the bed as it swished about, and after a few moments of contemplation the alicorn looked at Anon before speaking.

“Can I see you without your clothes on?”

Anon could only chuckle at the mare’s shy request to have him strip, but the young man obliged to the mare’s request. Hopping off the bed Anon started to un-cloth himself. Not in a tantalizing striptease routine, which did cross his mind, he instead just opted to undress himself normally. Once the last bit of clothing was removed Anon turned to look at the mare who was now dawning a look that contained a sense of wonderment, curiosity, and a hit of sexual craving. Just as Anon was about to ask Twilight if she liked what she saw, the alicorn hopped off the bed and immediately started to circle around Anon slowly, and seemed to be examining every inch of his now nude body, in which case Anon simply stood and waited till Twilight was done. After all, this is the first time that any pony has seen Anon naked, hell, Anon even heard some ponies gossip about what he looked like without his clothes on, or what his groin region looked like.

“I didn’t expect you to be so muscular Anon.” Anon heard Twilight remark as he felt the pony run a hoof along his thigh up to his waist, then the side of his torso.

“I do what I can to try and stay in shape, but trust me compared to other guys I’m average on the whole, muscular body type.” Anon said as he thought back to some of the guys that he’s seen that were really ripped, unlike him with his leaner build and light muscle tone. That’s when Anon noticed that Twilight was standing in front of him and looking squarely at his dick, and again the alicorn appeared to be flustered.

“I didn’t think kissing would’ve gotten you that, excited Anon.” the young man was a bit confused by Twilight’s word, but then he recollected on a passage in the medical book that he read out of boredom, and remembered something that caused a snicker to leave him.

“It’s always like this Twilight, but it’s not because I’m slightly excited.” Anon explained as he knelt down to the mare who was looking at him still slightly flustered. “Guys like me don’t have sheaths for our manhoods like your stallions, hence why we always wear pants.”

“Oh.” Twilight said as she wiggled nervously in place. “So, how do human’s get excited. Usually kissing gets a stallion partially harden and they just get even more so as they intake a mare’s scent.”

“Seriously? That’s all it takes to get a stallion good and ready to fuck?” Anon questioned as he didn’t read anything about this. Or thought that kissing is all that it would take to get a stallion good and rigid.

“Well no. what really gets a stallion hard are the pheromones that mares give off when we’re, aroused or expecting to be intimate, it’s these pheromones that gets a stallion ready for bucking.” Twilight explained as her tail continues to wag about.

“There is another way that a mare can do to get a stallion hard, but it’s a bit more, perverted and naughty.” The mare heavily blushed as she seemed to think about this other method, Anon on the other hand was more intrigued in what this other method was.

“And what would this other way be Twilight?”

“W-well a mare would p-place their stallion on the bed, then she would…nuzzle and lick his cock.”

“That’s it?” Anon questioned in disbelief. “A little foreplay is considered perverted here?”

“Foreplay?” Twilight questioned back. “You mean humans do this naturally for sex?”

“Yeah. It helps both parties get into the right mood, in fact—” Anon quickly stood up while clutching his hands under Twilight’s forelegs and carried her to the bed, which caused the alicorn to give an adorable squeak of surprise. The young man then carefully placed Twilight on the bed on her back, while he straddles over her and seemed to really make the pony really heated as she curled her legs up over her chest, and looked at Anon with wide eyes.

“Let me show how humans do foreplay~”

Anon then attacked Twilight’s lips with another deep kiss, but this time adding a bit more passion into it, which caused the alicorn to tense up at the sudden assault. But as the kissing continued her body started to lax and loosen up, even more so when Anon starts to run a hand over her stomach, hips, thighs, anywhere he could caress her. all of which turned the mare into puddy in his grasp. Breaking the kiss Anon started to delver love kisses on Twilight, starting with her cheek, then down her neck. Twilight was panting and groaning as Anon continued to lavish the mare, even moving her forelegs so that Anon was able to kiss her collar bone before trailing down her stomach, feeling her soft and velvety coat brush against his lips and nose.

Soon enough Anon reached the pony’s lower region, where Twilight kept her legs clenched to try and hide her marehood, but the probably already glossy honeypot wasn’t Anon’s current target.

Moving in Anon placed a kiss directly between Twilight’s teats causing the mare to give a startled gasp. That gasp then shifted into moans as Anon started to play with the alicorn’s teats, first by simply groping the small b-cup sized mounds in his hands, feeling their smooth thin layer of fuzz covering them and their harden nipples. As he groped and cupped the mare’s assists Anon noted that they were nice and plump, as well a little firm. The groping and cupping then switched over to kissing, and licking, all of which was making the poor little alicorn pant and moan like a dog in heat, her moans reached a fever pitch as Anon started to playfully suck on one of her mounds.

“A-Anon!” Twilight cried out as her legs opened and then clenched tightly onto the young man’s head.

“Easy there Sparkle-butt.” Anon said to the princess as the sides of his head started to hurt a little from the pony’s clenching knees. “Don’t crush my head now.”

“Sorry Anon but, I didn’t expect you to do that.” Twilight gasped as she un-clenched her legs allowing Anon to pull his head back. “Do…do all humans do this before sex?”

“I assume so. I know I do, and my partner always seem to like it.” Anon said with a small smirk as he looked down at the mare’s lower region. “And it seems that your way more than ready.”

Twilight followed Anon’s gaze down to her lower region, but then the young man saw her eyes snap up slightly and was focusing on something else. And when Anon looked down to what she could be looking at he saw that he himself was fairly erect. Shifting his gaze up Anon watch as Twilight kept on staring at his erect shaft until she looked away, and started to turn onto her stomach then arching her hindquarters up.

“Twilight?” Anon said in a slightly baffled manner.

“Anon I’ve been waiting for this for nearly twenty minutes, please just mount me already!”

“But what about—”

Anon was cut off in mid-sentence when the lavender mare backup into him, and wedging his cock between his stomach and her damp yet steaming marehood. The mare then started to wiggle her rump impatiently while she looked at Anon over her shoulder with a very pleading look. So pushing the mare back a few just to give himself some room, Anon stood up on the bed on his knees while moving Twilight’s hindquarters down, that way both parties were at some measure of leveled field with one another. Once both of them were in position Anon angled the head of his cock at Twilight’s marehood, feeling the heat emanating from it and hearing the squelching sound it made every time it winked.

Inserting himself into the mare the first thing Anon took notice of was the tightness of Twilight’s inner walls, as they clenched and gripped at his shaft as it continued to delve into the alicorns depths. The second sensation that Anon noted of Twilight’s marehood was the heat. The hot air emanating from the mare’s puffy dark purple folds was one thing, but his dick felt like it was wrapped in very hot and slick towels dragging across his length. In terms of tightness Twilight was like any other woman, however she trumped any in terms of how hot she was on the inside. As Anon continued to insert himself into the alicorn the tip of his cock pressed up against something, most probably the mare’s cervix which means Anon isn’t going to be able to shove the last few inches into the small pony.

After Anon had inserted most of his shaft inside of Twilight, as well as getting used to her tight walls, Anon started to pull himself out of the mare who clenched her walls to prevent him from doing so. But Anon managed to pull most of himself free from the constricting tunnel and just as quickly thrusted back into the mare, and proceeded to give Twilight her first experience of sex, and from the moans that the mare was giving with each, and every thrust Anon is giving her she was thoroughly enjoying it. Twilight also seemed to like when Anon spun her onto her side, and hiked one of her hind legs up and held it firmly as he really started to thrust into the mare.

“Anon I’m getting close!” Twilight cried out which slowed Anon’s thrust down slightly.

“Already?” Anon questioned as he looked down to the flustered mare. “We’ve only been going for a few minutes.”

“I…I—” Twilight couldn’t finish her sentence as she let loose a loud moan accompanied by a grunt from Anon as he felt the alicorns vaginal walls clench hard onto his shaft, and tried to milk him of his seed while a spurt of mare juices gush from Twilight’s marehood. While the mare comes down from her orgasm Anon ceased his thrusting and waited to see what Twilight wanted to do next.

“That…was…amazing.” Twilight huffed as she leaned up slightly. “Much more then when I do it myself.”

“Well I’m glad that I could help you feel great.” Anon said as he remained inserted in the mare. “So Twilight, do you want me to finish on my end, or are you—”

“I want to keep going.” The mare said confidently as she wrapped her tail around Anon’s waist. Anon could only crack a smile as he re-gained his hold on Twilight’s raised leg, and his pose on the bed.

Anon then started to resume his thrusts into the eager alicorn, starting slow to get both him and Twilight back up to speed, but even this simple act was already making the alicorn start to moan. Not as noisily and wildly as before, but more leveled and steady. As the pair continued on into their little rump Anon decide to switch things up again, and this time flipped Twilight fully onto her back as she was during their make-out session. Once the mare was flipped Anon leaned into give Twilight another bout of passionate kisses, while he really starts to ramp up his thrusting to where the bed actually started to jostle a little.

But during their make-out session Anon was surprised when he heard Twilight start to rev up her magic, and then feeling himself being flipped onto his back while Twilight is spun on top of him, now straddling the young man as she actually starts to ride him. honestly Anon was surprised that the mare would be bold of enough to do this, or even know how to do ride cowgirl style. But Anon wasn’t just going to lie there and let himself be ridden, if this bookish bookworm was going to put effort into this, then he was to. so he grasped Twilight’s waist, and the moment that she was about to thrust back down onto him, Anon shot his hips up and meet Twilight’s thrust with his causing her to moan out even more.

“Anon are you close yet?” Twilight asked Anon in between euphoric huffs as he continues to drive up back into her.

“I’m getting close again.”

“Not quite yet, but this might help me some!”

Anon started to really pump and drive his cock deep into the alicorn, making her bounce with every pelvic slam he delivers into her, feeling the tip of his member press up against Twilight’s cervix. Causing the mare to really cry out pleasure as she just lets Anon pump into her. several seconds of these relentless thrust later and the pony couldn’t remain propped up and fell upon Anon, laying flatly on top of him which Anon took advantage of as he could now really drive into the poor mare. Who reached her second orgasm and began spraying more of her juices all over Anon’s lap, but the young man didn’t stop, he didn’t give the mare a chance to ride her high out. Anon just continued to thrust into the clenching and strangling contracting walls of the alicorns love tunnel, prolonging her orgasm, and making it help him reach his first climax sooner to give Twilight what she wants.

And with one final thrust Anon pushed as much of himself into Twilight, and felt spurt after spurt of his hot seed be ejected into the small pony who arched her back and nearly blew Anon’s ear drums out with her wailing cry of pleasure. Which was accompanied by another burst of hot sticky mare cum. Adding more to the fluidly mess the both of them were making on Twilight’s sheets. Hopefully, Twilight put up a sound proof barrier, or something otherwise the whole town would’ve heard her, heck Anon would’ve bet that ponies in Canterlot would’ve heard her. A minute later and Anon had released the last bit of his stored up cum into Twilight, who was panting heavily into Anon’s ear while he was only lightly gasping for air.

“How was that?” Anon asked as he let go of the mare’s plush and plump flanks and had his arms rest at his sides, except for his left hand which he brought up to pet Twilight on the head.

“…mo…more.” Was all Anon could hear from Twilight as she continues to lay on top of him.

“More. Please…more…” Anon managed to turn his head to the side to look at the alicorn, and saw that she was thoroughly clonked out. Snoring lightly with a faint mutter of ‘more’ sprinkled in every other snore.

“Maybe next time. But for now, let’s take a nap and rest.”

With that Anon tried to get as comfortable as he could, and soon drifted off to sleep himself. If this was going to be a regular thing, then he might continue with his sexual endeavors with Twilight. If she really does wanted more.

But as he laid there on the bed a thought came across his mind. If he was willing to have sex with a pony, would he actually want something more than just physical satisfaction? Twilight did ask him this question, and at the time Anon thought yeah it wouldn’t be nice being alone in this world for the rest of his life, but now that he really thought about it, would he actually want something more? Like a family with a mare, if possible? If so then who could he pair up with? Anon looked to the sleeping alicorn and thought about it, and who knows Twilight might be willing to give an actual relationship a chance, and not just some scientific excuse just to have free sex. But then there was Rarity, she already voiced that she felt an attraction to Anon, granted it was based on the assumption that Anon liked her more than just a friend.

“Well, however this will all go at least I know that I don’t have to feel, weird or outplace in trying to pursue a relationship with a mare.” Anon muttered as a yawn escaped his mouth as he started to drift off to sleep.

“Only one way to find out though. And hopefully, it will all go smoothly.”