Unexpected valentines

by riicky83

Rating: mature
Tags: Alternate Universe, Porn, Fetish, Self Insert, Sex, Human, Sunset Shimmer, Anthro, Main 6, My Little Pony: Friendship is Magic
Length: 3440

It was my first Valentines at my new school and little did I know, the one whom I thought unpopular (me) would get lucky

Today would mark my very first Valentines at Ponyville High and as such, I'm not too familiar with how they celebrate the holiday. I'm still getting used to being one of the very few humans in the Pony school. While I'm not one to put myself down, I've never thought of myself as popular let alone lucky enough to find a special someone/pony in my life.

That'll change this day even thanks to a group of girls that have made a few plans.

Published 2020-02-14 00:10:02 UTC
Last updated 2020-02-14 00:10:02 UTC

Part 2. Ponyville High + Valentines =

"Ready for all of us?" Sunset asked as the five got closer to us.

I swallowed a lump that had formed in my throat. I slowly pulled out of Rainbow before Sunset turned me to fully face the mares. I watched them look at me with interest as they saw my now fully exposed cock, only Fluttershy had an embarrassed blush on her face but I could see that she was still interested in what she saw. I felt Rainbow's arms wrapping around me as she dropped to her knees, by this time, the mares had reached us and I felt several hands touching me, especially my dick.

"Ready?" Twilight said as her horn glowed.

Before I could respond, we were surrounded by a bright light before being teleported to the mares locker room that is connected to the swimming pool. I felt the girls slowly removing my clothes before they got me to lie on one of the benches. Looking up, I saw Pinkie sitting over my face as I felt somepony slipping my member into themself. and judging from the weak eep, I could guess that Fluttershy was the first of the new mares to fuck me. I started licking Pinkie's pie as I felt Fluttershy nervously move her hips. "mm, taste like candy floss" I thought as I savoured the taste as her curly pink pubes tickled my nose. I could hear the other girls moaning as I assumed they tended to each other, after all, there was only one of me and technically, I can only fuck one at a time.

Pinkie shifted her weight back a bit so I could see again and just in time too as I saw a patch of blonde pubes incoming.

Applejack had placed her hips over my face as her pubes and clit rubbed against Pinkies, her pussy now sat over my mouth as she wiggled her hips until my nose kinda went between her powerful flank.

Now the taste of apples was in my mouth as I lapped away at the new flavour.

"Ohh! my!".

I felt my cock going cold for a second before heat returned to it and the voice indicated that Fluttershy had swapped out with Rarity and speaking of swapping. Applejack and Pinkie moved a little so my nose was now somewhat under Applejack's pussy and my tongue could now lap away at a new flavour, Apple flavoured candy floss as I can now lick both of them.

I heard the showers being turned on in the distance.

"Don't worry partner" Applejack said between moans, "Sunset and Rainbow are just cleaning themselves up".

Once again, I felt my meat going cold before being placed inside another mare and judging from the difference in tightness, it must be Twilight this time.

"It always amazes me," Twilight said as the hint of moaning started to appear in her voice confirming that she was now riding me. "Equestrian magic works in mysterious ways when it comes to humans. logically you should be spent by now but here we are, still going strong".

I tried to think about what she was saying but with a hot pussy bouncing upon my shaft, I couldn't think.

Pinkie and Applejack stood up and allowed Rarity and Fluttershy to take their place.

Before I had a chance to taste the mares I came filling Twilight's pussy as she continued to move her hips up and down. "See?" she continued, You've just came and yet your still rock hard and ready to shoot more sperm for us". She continued to move her hips as she extended my orgasm a little.

Once I've came down from my lastest orgasm, I was finally able to lick the two new slits that were hovering above my face. One was a delicate flavour and the other was more exquisite. I couldn't even begin to describe it in any other way.

Eventually, I felt the cold air returning to my shaft before I felt two sets of tongues lapping away at my meat and one hand holding it up.

I could guess that Applejack and Pinkie were taking turns to suck me off as I hear hoofsteps fading away to the showers.

When Rarity and Fluttershy finally stood up, the mares helped me to my feet before Pinkie jumped into my arms as her pussy somehow managed to swallow up my dick unaided, her arms and legs wrapped around me as I carried her to the showers, fucking her along the way.

The hot waters slowly hit us as we walked under the showers, I watched Pinkie's hair goes from its candy floss appearance to straight-up flat from the waters. In fact, all of the girl's hairs and their tails went the same way due to the waters and it made them look hotter. Even their bodies look hotter as the waters ran down their sexy bodies.

I pressed Pinkie up against one of the walls as I started thrusted more into her.

The girls surrounded us as they either started touching themselves or each other.

I took a look over to my right to see Applejack as she was the last one who I've not screwed yet. I watched as she dug her fingers deep into both her pussy and her plothole as she blew me a kiss before licking her lips. I placed my right hand on her stomach before slowly trailing south until my hand reached hers, I replaced her hand with mine before I started fingering her with the same ferocity that she was using.

"Ohh! my suga" she moaned loudly as she opened her legs wider for me, "Just like that, more, faster".

I let Pinkie down as I slipped out of her, she looked a little disappointed but I think she knew that I wasn't finished yet. I moved over to Applejack before turning her around and bending her over against the wall. Shifting her tail to one side, I slipped my member into her snatch and started pounding her pussy hard. I watched her plot bouncing from each thrust as her fingers disappeared into her rear. I grabbed her hand and moved it from her plot before pulling out of her slit, "so you like some of that?" I said as my hands grabbed her flank before opening her plot hole. Applejack didn't answer me as I slipped myself into her anus. Applejack let out a moan indicating she like it so I didn't have to worry about holding back. I gripped her flank tightly as I screwed her plot. I wasn't gonna last long at this rate.

I pulled out of her flank before I started stroking myself, "line up and kneel in front of me girls" I said as I was getting close to busting my nut. I heard them giggle as they did what I asked them too. I jerked off in front of their faces as they cheekily stuck their tongues out of their open mouths. letting out a grunt, I finally shot my load. ropes upon ropes of cum landed on their faces, hair and their tongues. I watched the kiss each other as they cleaned my cum from their faces.

"Mm," Sunset said as she moved closer so she can touch my dick with her tongue. "Ready for more?, we have all day," she said before taking me into her mouth.

Looks like this year's Hearts and Hooves/Valentines I won't be leaving the school single as the other girls carefully lowered me to the floor as they surrounded me.

Part 1. Ponyville High + Valentines =

My name is Damian, I'm a regular human. Six foot tall, blue eyes and dark brown hair, average build you know?, just another regular person. The only thing I find special about me is that I attended a school that is mostly for anthropomorphic ponies, I'm one of a small handful of humans in this school so I don't attend certain classes without special equipment.

Wingsuits to fly like a pegasus, Unihelms to use unicorn magic or even Earth boots to use earth pony magic.

I moved to Ponyville almost a year ago due to recommendations from my previous school, it was in part a small community exchange as well as helping us to widen our knowledge and skills.

It took a while to get used to seeing all of the ponies on a regular base but after a few weeks to a month or so, it started to feel normal. Thankfully their physical structure was similar to ours, well if you exclude their skin and hair colours, tails, hooved feet as well as their wings and horns. Excluding the obvious changes, they were similar heights and builds to us so I wasn't left to look at something either half my height or double my height.

To be honest, it felt refreshing. Seeing various ponies of all three races and in such a variety of colours. By the time I was fully used to the sights, a year had nearly passed.

It was now Valentines or in Pony terms, Happy Hearts and Hooves.

Since I still felt new to the area, I didn't really have anyone special nor did I felt like anyone or anypony thought of me as their special one. To be honest, I've never really been lucky in love so I spent most of my Valentines alone. Well alone except for a few of my friends sharing their chocolates with me either due to them receiving too many or not being a huge chocolate fan.

I thought that today was going to be like any other Valentines I've previously had.

I looked around at the various couples that had formed in the hallways of the school as I walked over to my locker. I was surprised once I opened my locker, seven envelopes had been slipped inside. I picked them up as I placed my bag into the locker. I could smell perfume emanating from the envelopes especially when I opened them. These were Hearts and Hooves cards. I never had the time to analyse any ponies handwriting during my time here so without a name in the cards, I couldn't tell who they were from. "maybe it's some pony who was being thoughtful" I thought to myself as I read each card. As I heard the bell go I carefully placed the cards into my bag before heading to the first class of the day.

I did my normal for class, I sat at the back of the auditorium as I preferred the height they offered. The other students started filling the seats up as they stuck with the couples that I saw them forming earlier. I noticed two mares taking the seats next to me. An amber skinned unicorn mare with yellow and red hair to my right and a blue skinned pegasus with rainbow hair to my left. I was sat there waiting for the class to start but the teacher hadn't turned up yet. I thought the teacher was running a little late until something broke my train of thought.

A couple of hands running up and down my thighs making their way closer and closer to my crotch. The two mares that have sat next to me shifted a little on the long seat so they could move closer to me, I could feel their hot breaths on my ears as their hands made their way to my growing bulge.

"My aren't you getting excited?" the amber one said into my ear as she started to pull my zipper down.

"I can't wait to see what an actual human dick looks like let alone tastes like" the blue one said as she started undoing my pants button. "Illustrations are good and all but I much prefer to see the actual thing".

Working in tandem, they managed to pull my cock from my pants as they started slowly stroking me off.

The blue mare tucked some of her hair behind her pony ear before lowering her head to take me into her mouth.

The amber pony lowered her hand as she started caressing my balls so the other mare can have my entire shaft to suck. "Confused?" the mare said as her other hand started slipping up my shirt as she rubbed my back, "Hearts and Hooves works a little different to your Valentines at school. Here we're allowed to express our feeling more openly, see over there".

I looked to where her eyes were looking, sure enough, I could see several of the couples have started kissing each other but others have started either touching their partners or are currently engaging in sexual activities. I took in a deep breath as I felt my entire shaft being swallowed up by the blue mare before the amber mare started kissing me. I felt her tongue entering my mouth as the blue mare's tongue started wrapping around my meat. Without realising it, I had placed my left hand on the blue mare's head and my right on the amber mare's left thigh.

The blue mare was so skilled in her blowjob that I didn't even realise that she had lifted her shirt up until she moved my hand from her head and onto her bare breast.

I gave her breast a squeeze as I felt the soft yet supple flesh underneath my fingers, every so often, I ran a finger over her stiff nipple each time the back of her throat hit the tip of my dick. I felt my right hand being guided between the amber mare's legs and to my surprise, she wasn't wearing any panties. The base of my palm brushed up against her pubes as my fingers ran over her mound, slowly finding her clit and her moist slit underneath. Her pussy welcomed my fingers as they slipped inside easily. My left hand slowly left the blue mare's breast and started travelling south of her body until I reached her hips, I pulled her skirt up as my hand ran over her flank. She had on a pair of spats which made sense as she was a sporty type and I've seen her on the fields before but as I found out when my hand ran over the tight-fitting material, she had no panties on underneath. By the time my fingers made their way to her crotch and had started to rub her through her spats, I felt myself getting close to cumming.

The mares must've sensed this as the amber mare broke the kiss so she can focus on what was gonna happen next, the blue mare pulled her head up so only the head of my dick was in her mouth as the amber mare started jacking me off into the blue mare's mouth. The blue mare hungrily swallowed every drop I gave her as I held back a loud grunt as I felt my orgasm hit me, the amber mare not letting up as she carried on jacking me off into the other mares mouth until she had every last drop out of me.

The blue mare slowly sat back up before opening her mouth to show all of the cum she has acquired before swilling it around in her mouth and finally swallowing it. "Mm tasty," she said rubbing her stomach as she wiggled her flank so my fingers dug deep into her spat covered snatch. "Thick yet satisfying". She stared into my eyes for a second with a hint of lust.

I stared back until I felt the other mare taking me briefly into her mouth. My mouth opened to speak but I couldn't say anything for a second until, "Rainbow Dash?, right?" I asked as she nodded. I turned to the other mare who had just stood up. Before I could speak she had dropped her skirt and pulled her top up. I could see that she had no bra on underneath as I stared at her breasts, my eyesight slowly lowering as I saw her stomach then her red and yellow pubes before my eyes finally landed on her moist pussy. "Sunset Shimmer?, correct?" I quietly asked as she lifted one leg up before stepping over me so she was above my hips. I felt Rainbow holding my cock upright as Sunset sat down taking my member into her most private spot.

Sunset placed her hands on my shoulders as she started bouncing up and down, "I'm certain that a smart guy like you can figure out at least who gave you two of the cards you found in your locker" she said as her horn glowed. Her's and Rainbow's stomachs glowed, "Just a little contraception spell, can't run the risk of pregnancy yet now can we?".

Rainbow shuffled a little as she pulled her spats down so I could touch her directly, once she has pulled them down, she ducked under Sunset's arm and began to kiss me as she pressed her breasts against my chest.

My mind had stopped questioning myself as to what was going on as my right hand grabbed Sunset's flank, why question when I had a hand on one flank, several fingers inside one mares pussy and my cock going into another. Eagerly, I started thrusting into Sunset making my movements match hers. each time she went down, I thrusted up so I was fully hilted inside of her. Each time she raised her hips, I pulled down so only the tip of my dick was inside her. I carried on like this until I felt my second orgasm quickly approaching. I pulled her down onto my lap as I fired the first rope of cum into her pussy, as I came, I stood up as I placed the small of her back against the top of the desk. My fingers were still inside of Rainbow as I tightly clenched her flank as I kissed her, again I thrusted into Sunset, firing the second rope of cum into her. I thrusted a few more times until I've finished emptying my load into her and even then, I didn't stop moving my hips, only slowed down the movements. Slowly, I pulled out of Sunset before turning to Rainbow.

She had broken the kiss, eagerly waiting for her turn.

I moved closer to her as I bent her over the desk, crouching down I started licking her pussy after moving her tail to one side. Once I've gotten a good taste of her, I stood up and slipped myself right in before getting a good grip on her flank. Not holding back I went hard and fast and from the sounds of it, that's what Rainbow wanted. I watched her wings as they fully opened up. Her sexy blue flank looked so good underneath my hands as I slammed my hips into her.

Sunset had recovered from her orgasm as she placed her hooves onto the floor before getting up and walking around to my back, her arms wrapped around my stomach before sliding up my shirt, she kept her hips away from mine so I an continue to thrust into Rainbow. "You might be wondering why you have two mares at the same time right?" she said as she nibbled my ear, "here in Equestria we have a small herd instead of limiting ourselves to only one partner. This has several benefits, some more obvious than others. For us, this allows us to keep our friendships with each other if we all have feelings for one pony/guy. Why fight over a pony/guy when you can share him?".

As she finished her sentence, I slammed my hips into Rainbow's as I started cumming into her. "Was she serious?" I thought as my jizz left my dick and entered Rainbow's womb, "instead of one girl/mare I get a small herd of my own?".

"By the way" she continued, "To help us express ourselves, classes are cancelled for the day to help the students connect with each other and grow closer". She turned my head to the right where the doors were.

I looked over to where she has pointed me to. I saw five more mares walking over specifically towards us. Each mare had their skirts in their hands and all of them had no panties on so I could see everything down there. "Applejack?, Rarity?, Pinkie Pie?, Fluttershy? and Twilight Sparkle?" I said in disbelief.

"Ready for all of us?" Sunset asked as the five got closer to us.