Anonymous and His Day at the Office.

by NinjaMare

Rating: mature
Tags: Porn, Comedy, Rarity, Princess Celestia, Slice of Life, Sex, Human, Anthro, Anon, My Little Pony: Friendship is Magic, Second Person, Other
Length: 4156

Anon is about to share with us a little story that happened between him, and two very attractive students.

Anon is a simple guy, he works, he does his chores, and he helps out wherever he can. however, one pony in his life seems to trying to change his simple work and normal life, by bringing in a friend with a problem. and she knows Anon can't refuse to help a poor student in need.

-props to the artiest who made this pic: Pia-sama!
Link to their DeviantArt: https://www.deviantart.com/pia-sama.
-this story features a Rule63 Gender swap Spike, meaning you get to see Barb!
-and all character of this Clop are of age 18+

Published 2020-10-12 16:20:00 UTC
Last updated 2020-10-12 16:20:00 UTC

Anonymous What Have You Gotten Yourself Into?

Life is certainly a strange thing, as you never know what it’s going to throw your way. For me, I went from a guy who just finished college, and was ready to finally get my new apartment and a better job than at the book store. To now being in a completely different world altogether! Like I said before, life is strange.

What’s that? Who am I? Oh right introductions sorry folks, my name is Anonymous Gai…and yes…my parents named me as such. They thought it would be funny, and it was, for the other person. Not me.

You also want to know where I ended up? Well you see, I ended up in a world called Equess, on a continent called Equestira.

What’s with the horse terms? That’s the thing, you see this whole world—or at least the majority—is populated by beings called ponies. And no they’re not little earth ponies that walk on all fours, neighing and nickering. No my friends, these ponies are anthropomorphic ponies. Think a normal human, but with a very thin layer of fur covering the body, having a tail, and their faces being this weird yet cartoonishly cute equine like face. oh and they all come in a variety of colors, like one could be white with a blue mane and tail, then the next pony can be green with a red and brown stripped mane and tail. Another thing about these bipedal ponies, is that they come in three distinct types, where are unicorn, pegasi, or more redundantly, earth pony.

How long have I been here? Roughly about five months now, and I’m starting to get used to how things work here, mostly.

How did I end up here? OH! That is a story in a half! I won’t go into full detail, as it still makes my brain hurt, but sufficient to say…I have an arrest warrant on a lavender unicorn who not only brought me here, but also tried to molest me for ‘scientific research’. And it is also because of this mare that I was brought to Equestria, and as far as I’m told by the princess—and yes these ponies run on a diarchy-based system—the way to send me home is, well, it’s pretty close to impossible.

So now adays I live in the castle at the capital city of Equestria, probably the only up-side to this whole thing. Aside from that, I also have a rather good paying job, and all I have to do is be a guidance counselor to students at Canterlot’s most esteemed school for ponies. At first things didn’t go so smoothly, as these rich snobby teens were just a bunch of rich punks, sluts and skanks, and all bark and no bite. But after my first week, these kids mellowed out and started to make me out as a celebrity, since I’m a one of a kind creature, with knowledge and ideas from another world, and whose been getting really chummy with the head princess.

But enough about how I got to Equestria, and my current living arrangements. You all came here for a story, one about me and two of the school’s students. Well pull up a chair and listen closely, because this is going to be one story you’ll won’t forget. I know I sure won’t forget this day.

~~~~~

It started out as any other day of the week for my new life, me sitting in my small office at the Canterlot School of Grace, and yes someone actually named the building with that name. Ponies have an odd naming convention when it comes to anything. Anyway, I was just sitting at my desk, going over a few papers, both school and castle related. And as I was going over the materials, as well as enjoying a cup of coffee, the door to my office knocked.

“Doors open.” I said without looking away from the papers in my hand. Entering my little office was a student that’s become a frequent visitor.

The pony is named Rarity Belle, a white coated unicorn with a styled blue mane and tail with royal blue eyes. Despite coming from a very humble background, Rarity has become one of the most influential students of the academy, and all thanks to her talent in making outfits, and knowing what trends would be trends and how long they’ll last. And despite the prim and proper way she acts while around the school, or around students and teachers, is facade. Rarity is probably the biggest…slut would be the proper word, and trust me, that’s probably the polities thing I can describe her. And for some reason she never shows this side of her to nobody, except me. Either that, or she only acts like this to me, and her prim and proper show is her real self. It’s really hard to tell with this girl.

But other than that, what surprised me was that Rarity didn’t come alone. Now I know that this world has other creatures aside from the ponies, for example there also griffons who are also anthropomorphic, same with zebra’s, and strangely enough cat people.

But the other person with Rarity isn’t one of these creatures, it was actually, a dragon! Not a towering scaled monster with massive wings, and burn everything down type of dragon.

This dragon is obviously female, as her curves and body were…not really covered up by her school uniform. Granted the outfit for the girls is a short, and I mean SHORT, skirt. The shirt was fine, but its pretty thin so it emphasizes their body to much, even more so when they tie the bottom right under their chests, really showing off their cleavage. My god it’s really hard to be around these high schoolers at times.

Anyway, this female dragon was actually really cute looking, muzzle was round, her big green eyes were adorable, and the fins on her head seemed to be styled like Rarity’s mane. How the hell that actually works or happens, I will never know, but it does make her look more cute. But if you look at the rest of her body…it’s so different from the word ‘cute’. She was clearly the tallest person I’ve ever meet, she’s as tall as Princess Celestia who is close to 8.ft. Her body is lean, curvy and has a good definition of muscle. her arms and legs were more shapely than muscular, and speaking of legs—dear sun above—they were thicc! As for coloration, her scales were a nice shade of purple, while under side scales were a pale green, and her aforementioned fins or frills are green.

All in all, she was the same oddly cute and sexy as the mares of Equestria.

“Good morning Mr. Anon~” Rarity cooed as she sat on the edge of my desk, rather than one of the two chairs. Her companion on the hand just stood by the door, fidgeting with her tail, and…is she blushing?

“How are you today?” the mare asked as she leaned over to me, giving me a good look down her shirt, and the crevasses of her bosom.

“Pretty good.” I simply stated, no longer hiding my blush or the obvious enjoyment of the sight I am seeing, as she does this every time she visits. And I know for a fact that she likes it.

“So Rarity, what brings you here so early, skipping your literary class.” Rarity turned to look at the dragon girl, and ushered her to come over.

The dragon hesitated at first, but she eventually made her way over to my desk. When she was close enough, Rarity hopped off my desk and grasped her friends hand, and pretty much pressed herself against the dragon. Their chest pressing against one another as they both leaned forward just a bit.

“This is my friend from Ponyville, who was accepted into the academy just a month ago, her name is Barb Draconia Sparkle.” As Rarity introduces her friend, Barb gave a small wave and her blush seemed to have deepen slightly.

“Nice to meet you Barb. My name is Anonymous Gai, but please just call me Anon.” I said to the dragon as I stand and reach a hand out for a shake, the dragoness left Rarity’s side and took my hand. Her hand was a bit bigger than mine, and was really smoothed, like it was polished very thoroughly.

“Nice to meet you Anon.” Barb said with a very nervous voice. After we shook hands, I sat back down in my chair, and while Rarity sat on my desk again, Barb sat in one of the two chairs.

“So what brings you two here so early in the morning?” I asked the pair. Rarity, I could guess why she’s here, but since I’ve just meet Barb I can’t exactly be sure.

“Well~” Rarity said as she licks her lips. “The reason for our visit is actually for Barb.” I looked to the dragoness, but she just blushed even more and seemed to be fidgeting with her tail even more.

“Before Barb came to Grace, and I visit my hometown for the holidays, I often tell Barb of the most heartwarming, and caring counselor of the school…and all the ways he relieves my, stress.” I think I’m starting to get why these two are here, and why Barb looks so, flustered.

“So you’re basically here for your, message.” I said to the mare who just gives me a cheeky smile.

“And you brought your friend to, join?” I asked for clarification as I gesture to the dragoness.

“When Rarity learned that I was accepted to Grace, she said she could arrange a way for me to, loose my virginity.” I was about to say something, but Barb continued to speak.

“You see, I’ve never had a colt friend before, because most ponies don’t see dragons as, attractive. And mostly avoid us. But when Rarity told that there was a creature that doesn’t discriminate with species, and has had sex with a griffon transfer student, I thought that maybe…we could…”

I looked from the blushing dragon to the confident unicorn, who just gives me a knowing smile. Giving out a sigh I scooted my chair back from my desk, and gestured the dragoness to come on over, so we can get this over with.

The dragoness actually looked happy and quickly rushed over to my side of the desk, while Rarity stood up and actually sat in the other chair. As Barb reached me she immediately went into the foreplay by kissing me. Her muzzle was actually pretty soft, not as hard as you’d expect say a crocodiles snout or muzzle, and she was actually a good kisser. Either she’s a natural, or she’s had a ton of practice.

After a minute or so locking lips with one another, and feeling her long tongue coil mine, the dragoness then kneeled down in front of me and starts undoing my pants. She did hesitate a bit when she got to my boxers, but she quickly shook her hesitation away and pulled them down, letting my manhood spring up. already partially hard do to how the two girls were dressed, getting a peak at Rarity’s chest, and having a sexily cute dragon attempting to have sex with me. Barb swallowed a lump that formed in her throat, before she went about to giving me a blow job.

Her long tongue snaked out of her mouth and began to wrap around my cock, and holy hell, this was next level oral. Once she got her tongue wrapped around me, Barb lowered head and began to suck as she starts bobbing her head. her soft snout pumping into my pelvis with each bob.

“Well Barb, how does he taste? Just as I said, or better?” Rarity spoke suddenly. I looked over to her, and saw her rubbing her slit through her panties, while her other hand fondled one of her breasts. Barb stopped her bobbing before pulling herself off my dick so she could speak.

“…b-better!”

The dragoness commented before going back to assaulting my dick with her hot wet mouth, the tips of her sharp teeth ever so gently grazing the skin of my shaft. I couldn’t resist any longer, and I began to thrust into Barb’s mouth every time she lowered her head, and if the moans are of any indication, she was loving it. however I didn’t get to enjoy my thrust for to long, as the dragoness patted my thigh to get me to stop.

“What’s up?” I asked, a little disappointed that the blissful moment ended so suddenly.

“I…I want you to cum…” Barb panted as she stood up, and lifted her skirt…showing that she was going commando, her puffy dragon pussy soaking with juices with her clit winking in and out of its hood. “In here.”

I reached out and grabbed one of her hands, and pulled her towards me, where she sat on my lap. My cock wedged between her lips and my waist, and by the stars she was soaked, and the heat I could feel from her nethers. Wow!

Repositioning herself, Barb stood on her knees on my chair and gripped my shaft in her hand, where she starts to position it so that the tip was partially pressing through her folds. Once my cock was set, the dragoness slowly lowered herself, pushing more of my shaft into her depths which were hotter than any woman I’ve had sex with before. Even Rarity’s confines aren’t this burning hot. Then when I had about five or so inches left, Barb slammed the rest of me into herself as she lets out a short, yet strong sounding animalistic growl mixed with a moan.

“S-so…this is, what it f-feels like, to h-have a real dick…inside y-you.” Barb mumbled as she gyrated her hips, causing me to slosh around inside her, feeling her walls suck and clench around me.

“I can f-feel it pulsing. Dose that m-mean you, like it?” I placed my hands on the dragoness shapely hips before looking at her with a sincere look.

“Yes.” I simply said, to which Bard leaned down and started to kiss me again, that wonderfully long tongue of hers coiling around mine.

Breaking the kiss, Barb began to slowly pump herself on my shaft, which felt her burning walls try and attempt to milk me. I restrained myself from just thrusting into the poor girl, this was her first attempt at sex, so I wanted her to dictate how things progress.

“Her boobs darling~” I heard Rarity say. Turning to look at her again, I saw her now fingering herself as she plays with her nipple through her shirt. “She loves it when somepony plays with her breasts.”

Looking back to the dragoness, I focused on her bouncing breast as Barb began to pump herself faster. Reaching up I slipped my hands through her shirt, grabbing her breast, feeling hard nipples grace my palms as the dragon moaned. I began groping the supple mounds, which were at least a cup size bigger than Rarity’s C-cup, but were also softer than I thought a reptilian’s breast would be

Leaning forward slightly, I moved one of my hands to the side to reveal the perky dark purple nipple, where I licked it a few times before sucking on it. Barb moaned again, and even wrapped her arms around my head as I continue to suckle, and she continued to piston herself on my rock hard rod. Barb groaned as her hips moved faster, the heat within her increasing to an incredibly arousing degree.

“MR. ANON!” Bard growled as I heard her tail thrash against the sides of the chair, and smacking the cavity of my desk. “Cum inside me! Breed me!” she drooled on as her hips slowed down, but increased in the force of each drop they made.

“Pour your burning hot white cum inside my deepest depths, and make me—” the dragon’s voiced hitched as she slammed down on my hip, where I felt myself explode inside her as my tip was pressed against her cervix, while she roared out in pleasure as boiling fluids gushed from her. coating both our waists “…so…warm…”

Barb leaned herself back once she somewhat recovered from the excursion, pulling the breast in my mouth out as she fixed me with loving expression. Not saying a word, the dragon once again locked lips with me and pressed more into it, as her hips gyrated a bit. The feeling of mixed fluids squelching between or hips.

“Can we…do this again? Please say yes.” The dragoness begged as her tail wagged behind her. I fixed her with my most resolute expression I could muster at the time before speaking.

“Only if you keep this confidential, scrub yourself thoroughly clean once you leave this office…” I looked over to the unicorn, who was not fingering herself as vigorously as she was a moment ago. “And not as frequently as her.” the dragon gave me a quick peck before replying.

“I promise.”

Peppering me with a few more kisses, Barb eventually lifted herself off me—albeit unsteady—and wobbled over to the other chair. But before she sat down, she whipped a little bit of my cum off herself, and licked the finger clean. And judging by the shiver I saw her body gave she liked it. I then felt a pair of hands grab the sides of my head, and made me face Rarity as she went in for a deep kiss, her togue wrestling with mine as we made out.

“I hope you still have some left for me?” Rarity mused as she got herself in the same position Barb was in. “Consider it my severance pay for bringing another student for you to help.”

Without any preparation or added foreplay, Rarity’s horn ignited with magic and gripped my still hard shaft, and pretty much slammed herself down onto me. now while Rarity wasn’t as burning hot as Barb was, she was way tighter…which still puzzles me despite how many times we got at it. after only a second of steadying herself Rarity started moving her hips, clenching every time she pulls up to get me back to prime hardness, and unlike with Barb I began thrusting into the thirsty student.

“Darling.” Rarity moaned as she looks down at me while undoing her top, showing that she was once again going braless. “I have a special treat for you~”

She then used her magic to pull my head to her left breast, where I began to suck on it, rolling my tongue around on her erect nipple. But after giving a few sucks I felt something creamy touch my tongue. Holy crap, she’s lactating! I didn’t think she was even capable of that.

“Yes darling, that’s it. Drink up mama’s warm milk.” Rarity teased as she brings my left hand to her right breast, and when I felt that soft and velvety mound in my grasp, I started to grope it hard. Getting another pleased moan from the slutty student.

“Yes! That’s it, use my body to curve those desires of yours!” Rarity moaned out loud as she picked the pace up in her thrusting, which made me thrust into her more.

“Your such a naughty man aren’t you Mr. Anon, using your students like sex toys—AGH!” I pinched and bite down on the mares nipples, causing more milk to spurt out as she continued to dirty talk in how I’M using HER. when it’s the other way around.

“You love f-feeling us poor young t-teenage mares wrap around y-your cock, and feel us give w-way to your penetrating—OH STARS YES—o-our most sacred of d-depths!” If she was going to play this victims game, I might as well put some effort into it.

Removing my mouth from her tit, already missing the coconut tasting milk, and quickly standing up as I held Rarity, who actually looked shocked by my sudden action, I then angled her above my desk and after placing her down on the hard wood counter, I spun her around while still impaled onto me. Earning another moan from her. once she was in position, I started ramming into the slutty unicorn as hard as I could, getting cries of pleasure from her as I rocked her body. I could see her breasts being smooshed against my desk, and causing it to be covered in milk every time I thrusted into Rarity.

“Admitted it you little whore.” I said in a confident, bad guy voice as I leaned over her, nibbling on her left ear causing a shutter to run down her back. “You like it when I take you, make your pussy mine and mine alone.”

“Y-YES!” Rarity screamed as her hips started to thrust back into mine hips. Luckily, my office is far away so no one can hear her.

“I admit it! I love it when you bend me over, and shove your fat cock into me! It makes me feel good!” Rarity complied to my bad guy role.

“I want you to cum inside me, I want your vile semen to flow inside me!” I gave a few more powerful thrusts into the starving mare, before pulling back so much that only the head of my cock was still inside the mare.

“Then take it all, you little SLUT!” I emphasized my last word with the final thrust, pushing both me and Rarity over the edge.

Rarity’s arched back as she cried out in pleasure, milk erupting from her tits as they spray not only my desk, but my floor, carpet, and Barb. Who was also fingering and playing with herself as she watched us fuck. Coming down from her high Rarity dropped to my desk, her boobs being squashed under herself and giving one last spurt before tabbing out. As for me, I slowly pulled out of mare, who clenched her walls to try and keep me inside her, but I managed to pull myself free and collapse into my chair. And watched as my cum oozed out of Rarity’s thoroughly abused pussy.

“Well, I think that enough romping around.” I said as I wiped my forehead. Rarity weakly lifted herself off the desk and tried to stand, thankfully she didn’t fall over and began making her way towards my door. Barb followed behind, but before they left they pressed against each other and each blew a kiss in my direction.

“We’ll be back during lunch for a second round~” they both said in unison before leaving the room, their tails raised to give me a teasing glance at their swaying hips.

When my doors closed I breathed a sigh of relief that I have some breathing room. I was used to having Rarity stop by my office two times a day, one during lunch, and another during a class she didn’t care for, and get two rounds out of m before she left. However I get the feeling that now I’ll have to go four rounds twice per day, if Barb ‘forgets’ our agreement. Looking at the mess on my desk, and peering over it to see the milky mess on my floor, I know I’m going to have to clean this up, fast before another student or teacher comes in.

“You certainly been busy Anon.” I jumped out of my chair when I heard Celestia’s voice pop in out of nowhere. Recovering from the fall, I stood up and saw Celestia slowly materialize in the corner of the room.

“Celestia! Wha—when?”

“I arrived when Rarity and her friend came in, course I was invisible the whole time.” Celestia chortled as she snapped her finger, her horn igniting with magic, and my office was cleaned in a second.

“Though I must admit, I didn’t think you helped the students in this sort of manner.” I’m not sure, but I thought I saw a small sparkle of mischievousness in her eyes when she said that.

My thoughts were cut short when I was lifted into the air, placed into my chair, and saw my office be enveloped in golden light before going back to normal. I looked over to Celestia who was undoing her dress, letting it drop to the floor, revealing her outrageously curvy voluptuous figure to me, before removing her bra and panties as well as she stood before me.

“Care to give me the same treatment~” I looked up past the large white mounds that were Celestia’s mountainous cleavage, and saw a playful glee in her eyes as a small sly smirk graced her muzzle. I gulped down the lump in my throat as a thought came to me as she started to lean herself down towards me.

‘I’m fucked!’