After School

Story by 5_paws on SoFurry

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This one took me wayyyy longer than expected and coincidentally turned out wayyyyy longer than expected as well.

I actually like femboys/traps very, very much, but I don't think I have ever written a proper crossdressing trap story. Well, now I have, and it is a long one!

At first, I had some trouble on what species to make the MC, but luckily I have been exposed to a surprisingly large amount of femboy donkey art in the last few months, and being I've never written about a donkey character, I thought a slender, young donkeyboy would do just fine.

As mentioned above, this story stretched out way beyond what I first thought for this. I actually suffered a bit of writer's block and general laziness when writing this piece, initially wanting this to come out on Friday, but having to push it back to now, since it wasn't done in time. One of those projects I really enjoyed writing the first half of, and then, when it got stretched out too long, I began to resent the text a little bit, really just having to push through the last 4000 words, luckily getting a few strokes of inspiration in the middle. This also proved to have its own difficulties, for example, I wanted the other four characters to remain anonymous/without names for thematic reasons, and because the story went on to become so long, it felt like I was just repeating nouns and pronouns for the characters way too much than I was comfortable with.

But then, during the chiseling and cleaning process, I actually found myself to be quite happy with the end result. Certainly not perfect, but I swear if I spent any more time working on this, I would just start nitpicking and be even more unhappy with it in the end.

Anyway, here it is, please enjoy! 9400 words of heart-pounding crossdressing furry femboy action!

(Also to clarify since we are talking about high-schoolers here, all characters ARE 18 and/or above)

Also, also, Yay! I made myself an icon. Wow!


The late afternoon sun was casting long shadows into the empty school corridor, along which Sam was gradually moving towards the geology classroom. The shoes of the shy donkey beat a steady rhythm against the school's concrete floor, the dull clap of the silicon soles echoing in the third-floor corridor. Sam actually quite enjoyed going around the school like this, the bustling buzz of the early afternoon replaced with silence and tranquility as most of the students had already left the building. It was as if the entire building itself had been wrapped in an aura of equanimity after the busy day.

Quietly humming the tune of his favorite TV-show, Sam soon reached the door marked with "D-1" or better known as the geology classroom. The reason why the long-eared equine wanted to go into the classroom after school, was to retrieve his phone, which he had forgotten inside the desk he was using two periods ago. Sam hadn't actually even noticed it to be missing, until the geology teacher ms. Rocks had bumped into him in the hallway afterwards and said that she had his phone in her desk drawer back in D-1. She had said she would leave the classroom door unlocked for Sam, as long as the young donkey locked up after retrieving his phone.

Taking the final steps before the classroom door, Sam set his hand on the door handle and heard the resounding click when he turned it downwards in its socket. The metal door with a clouded glass window opened and Sam stepped inside the familiar classroom.

The D-1 was on one of the outer walls of the school, and the same, orange sunlight which had lighted the hallways on Sam's way there, also lit up this classroom. Sam could see small dust particles gently floating in the air, made visible by the rays of light seeping in from the large windows. It was kind of beautiful. Sam sighed, admiring the view for a while, before turning to his right to go and head for the teacher's desk.

Just then, the grey equine realized that he was not the only person inside the classroom. On the far right corner in the front of the classroom, there were four characters, lazing about over one of the many desks of the room. Judging by their long and colorful hairdos, slender limbs, and different style of uniform, all four of them were female. Also judging by their uniforms, they were all third-years just like the recently entered equine. Sam immediately got four pairs of glowing eyes facing towards him as he took a few careful steps into the classroom.

Not quite categorized in the 'popular' caste of the high school, Sam had relatively little experience and even less confidence in interacting with girls. Suddenly faced with not one, not two, not three, but four females, all alone inside an otherwise empty classroom, Sam quickly got super nervous, swiftly averting his gaze from the group staring at him. Probably noticing that he was not a teacher, the four went back to conversing with one another, not paying much further attention to the sole donkey at the other end of the classroom. Looking like he had just avoided a direct confrontation, Sam sighed quietly and started heading for the teacher's desk, making sure to walk a few desk rows away from the group of girls.

Even though it seemed that none of the four were paying particular attention to Sam, the donkey could still swear he could feel at least one pair of eyes following his every move as he finally reached the big desk in front of the blackboard. Still averting his eyes from the four females, Sam began rummaging through the drawers, looking for his smartphone. He managed to get lucky with the second drawer, finding his phone on top of a stack of last year's geography tests, which for some reason were left there.

Having achieved his goal, it was now time for Sam to make a quick getaway and head home for the day. But as he was stepping away from the desk, the young male's curiosity got the best of him, and he took a glance towards the females on his left, almost instantly locking eyes with one of them who seemed to have been the one staring at him for a while. She was a cat with long blonde hair, purple eyeshadow, and turquoise lipstick decorating her fair muzzle. Her eyes had a mysterious gleam in them, and she smirked slyly as he saw Sam looking at her.

Before the mesmerized Sam could look away, the cat suddenly grabbed one of her friends on the shirt collar, pulling the surprised snow leopard in for a passionate kiss. Sam gasped, stopping in his tracks upon witnessing the impromptu girl-on-girl makeout unfolding just a few feet away from him. The other female looked surprised and slightly annoyed at first, but after brief eye contact with her cat partner, she also seemed to notice Sam, and consequently put more effort into making out with her friend. From where he was standing, Sam easily heard the sounds of their sloppy kisses, as well as the occasional moans dripping from their wrestling lips.

Then just like that, it happened.

It was a completely natural reaction from a teenage male. The front of Sam's pants bulged up as his equine member got erect within seconds of seeing the two girls make out in front of him. The surprised donkey didn't even realize it himself, just standing still in the middle of the classroom with a tent in his trousers. The tongue-wrestling felines soon separated their lips, leaving a strand of saliva between their mouths, which glistened in the afternoon sunlight.

"Hahaha! Sproing~!" One of the other two girls, a turquoise-haired Shiba-Inu soon giggled, pointing towards Sam.

The dumbfounded equine looked down and noticed the sizeable tent he was pitching. Getting all flustered and blushing madly, Sam covered his front with haste, but there was no doubt all of the four females had seen the erection. Sure enough, the rest three were also snickering amongst themselves while looking at Sam.

"Must be a virgin!"

The other three continued their mindless giggling, but the blonde cat only had a mischievous smile on her face as she gave Sam and his crotch an intense stare. The cat quickly leaned over to the Shiba-Inu, whispering something in her ear which made her stop giggling, and the same, mischievous smile spread on her face as well, and she gave the cat a short nod in response. The blond feline then tapped her two other friends on the shoulder, whispering something to both of them, and soon, all four females were looking at Sam, smiling as if up to no good.

The cat got up from her chair, her three friends following suit, getting up from their respective seating on the adjacent desks. Sam looked at them all nervously as the turquoise-haired canine walked to the other end of the classroom, closed the door, and Sam was sure he heard the clicking of the lock as well. The timid equine swallowed hard setting his eyes on the three others: a cat, a bunny, and a snow leopard, who carefully approached the lone donkey.

Now only one row of desks away, Sam took a step back, still covering his front with his hands, as the blonde feline inched her way ever closer to her target. In the end, she made a leap, planting her hind paws just a foot away from Sam's hooves. "Hey there!" She said, her voice dripping with honey as she smiled, tilted her head, and blinked her big, colorful eyes at flustered Sam. The cat leaned in closer, her eyes traveling all over the perplexed equine's still body. From his slightly upper angle, Sam could see just the faintest glimpse of her bra as she leaned towards him.

"So..." She said, retracting her face from around Sam's chest. "Are you really a virgin?"

Sam blushed and tried to look around himself for any openings, but noticed that he was quickly surrounded on all sides by the cat's three friends. Pressing his lips shut, Sam tried to look past all of them and just stared at the wall as he began to sweat under the growing pressure the females asserted to him.

"Ahem, let me rephrase myself a bit. Have you ever FUCKED a PUSSY with your COCK..?" The cat asked again, and Sam swallowed, still avoiding looking into her eyes.

"Hmmm... I'll take that as a yes then..." She giggled, facing her eyes down from Sam's blushing face, and down onto the donkey's crotch.

"Perfect... Virgins are my favorite, you know?"

The cat swiftly leaned in to plant a small kiss onto Sam's lips, and the donkey's ears shot straight up in surprise. The sudden kiss momentarily threw Sam off-guard and he loosened his defense around his groin and the observant feline was quick to take advantage of that fact. Before Sam could recover from the kiss, she pushed her paw down Sam's pants, curling her slender fingers around the base of Sam's thick donkey member.

"Goodness! I knew all equines were packing but I never thought it would actually be this BIG..." She whispered, now pressing her body against Sam, who was frozen still, as it was the first time anyone other than him touched his cock. The cat quietly slid her other paw down Sam's pants as well, now grabbing the equine shaft with both, slowly starting to rub Sam's member within the school uniform trousers. Sam gasped, tensing up his body as the sensation of a stranger touching his cock quickly sent sparks of pleasure up his spine, his erection reacting strongly to getting rubbed.

"Mmm~ How are my paws? Breathtaking..?" The feline whispered, carefully rubbing Sam's hidden erection while smiling impishly. Sam was unable to reply. The grey equine soon winced and lowered his ears as the feline callously moved her paws just over Sam's sensitive tip. The other three females looked on with great interest as their assumed leader jerked off the awkward donkey in the middle of the classroom.

It didn't take too long before the cat's paws started to feel a bit too good for Sam, and his equine body shivered as pleasure coursed through it with every stroke of his cock. Sam was about to cum, and the pleasure building up in his body made him lose sight of anything else around him, even from the feline leaning against him slipping her right foot behind Sam's legs. The mischievous feline quickly yanked her hands away from inside the flustered donkey's pants and pushed Sam backward, tripping him with her own, well-positioned hind paw. Sam lost his balance and tripped, only barely managing to cushion some of the fall onto the floor with his hands.

Now suddenly laying down on the floor, Sam watched mesmerized as the cat slowly trailed her paws up her skirt and delicately took off her purple panties, tossing them to the nearby desk as she stood astride Sam, just above the donkey's crotch. The skirt of the female uniform was still covering her nether regions, but the allure of the exposed genitals had just been increased tenfold by her removing her underwear. She quickly dropped down on Sam's lap, grinding her bare rump against the big bulge on the front of the laying donkey's uniform. Sam twitched, feeling the shapely feline behind rubbing against his bulge.

"Ok, Mr. Virgin! How about we make a deal? Just keep this big and throbbing cock of yours hard for me, and I'll help you lose that virginity 'kay?" She said with a wide smile while flicking her striped tail from side to side, sitting on Sam's crotch.

Was she actually serious? Could this really be a chance for Sam to take a proper step into adulthood, here, in after-hours school? The whole situation was a bit weird, but the young male couldn't help but feel at least somewhat excited when a beautiful female approached him aggressively like this. Sam carefully nodded his head.

The cat smiled and blinked her big and colorful eyes. "...Of course you will..."

"Then, how about you show me yours, and I'll show you mine, okay?"

The dazzling feline moved a bit backward on top of Sam, getting herself just below the equine's waistline. Sam's breathing and heartbeat both grew in pace, as the blonde cat swiftly unbuckled the belt binding Sam's trousers and she started pulling down the bottom of her school uniform. Sam looked the expression on the cat's face lighten up as each inch she tugged down the pants, more of Sam's shaft was revealed to her hungry eyes. Just a little less than an inch lower, and the sizable equine erection sprung upwards from inside Sam's pants, and the female cat let out an exaggerated, elated gasp.

"What a catch..." She muttered, then dragging her soft backside back over to where it was before, more on top of Sam's stomach. Sam shivered as the exposed milky fur of her butt touched his member directly. Planting her buttocks on Sam, with the donkey's raging erection just outside her crease, the feline now grabbed the front of her skirt, giving Sam a sly wink.

Sam subconsciously stopped breathing as he watched the bland piece of pleated fabric slowly getting raised by the delicate feline paws of its owner. She lifted up her skirt more and more until Sam finally saw her... dick?! Indeed, there was a decent-sized, uncut and erect cat cock peeking at Sam, just underneath the uniform skirt. Sam's horny teenage brain overloaded and his expression froze to show the emotions of shock and disbelief.

Seeing the confusion and shock on Sam's face, the, now presumably male, cat burst out laughing, his slender figure trembling on Sam's lap. The others started to laugh as well, not at all trying to hide how amused they were by the donkey's reaction.

"Disappointed?" The cat asked, rubbing his rump onto Sam's cock, planting his paws on top of Sam's chest. "It seems we got you good. You see, we are all boys here."

Sam took a quick look around shifting his gaze from the Shiba to the bunny and snow leopard, who each held up their own skirts, showing the dumbfounded donkey unmistakeable bulges on their girly underwear.

"I hope you don't judge our little... hobby... And you know... the offer still stands."

Right now, Sam was all kinds of confused. They were all actually male. Credit where credit is due, they all looked extremely cute for being boys, and besides their maybe a bit 'lacking' chest, they could very easily pass for being females. This was clearly something they had put some effort into. In fact, their appearances were still convincing enough to fool Sam's erection, and the boner the donkey had churned up before refused to go down even now when the jig was up.

The cat quietly raised his hips and grabbed a hold of Sam's cock with his right paw, guiding the tip into his warm and fuzzy feline furrow. "So is that a yes...?" He asked, rubbing the sensitive tip all over the length of his cat crease, enjoying Sam's flustered reaction. "You sure? Last chance to back out." He said, pressing the tip of Sam's equine cock to his soft, outer anal ring, which twitched upon meeting with the hard cockhead. Sam's mouth was half open, as he tried to come up with words to speak with, but not a sound escaped his lips.

"Too late!"

The cat voiced a surprised meow, as he put his weight on Sam's member, burying the lengthy equine meatpole between his cheeks. Sam was rendered completely speechless as the insides of the blonde cat's rump wrapped his shaft in their tight, velvety grip. It all happened so fast, the young donkey barely had time to register the penetration act before his hips already met with the creamy feline backside on his lap.

"Mmmhhhhh~" The cross-dressing cat mewled out, wiggling his ass for a while to get a better seating on his flustered steed. "How do you like my ass, Mr. virgin? It's not like you would know, but I can tell you it is much more ~Mhn~ ...pleasurable... and tight than a pussy." The crafty feline giggled, dragging his cheeks back and forth on Sam's lap, moving the equine shaft around inside his colon. "Is it good?"

Even if he was able to talk from all his panting, Sam couldn't have refuted any of the feline's words, at least if he were to be entirely truthful. The soft tailhole around his cock felt insanely good, and for sure way better than any of the times Sam had masturbated. The pleasure was so overwhelming that Sam had to lay completely still, afraid he would cum if he made even one wrong move.

Seeing the confusion, bliss, and desperation in Sam's expression, the cat again giggled to himself, rubbing his rear against the laying donkey. "That good huh? Then aren't you in for a real treat, because I haven't even started yet!"

A careful moan slipped out from between Sam's lips as the slender feline on top of him moved his lower body, raising his fuzzy hips and sliding the throbbing donkeypole out of his tight tailhole. The cat emitted a soft purr as he lowered himself back onto Sam's member and another jolt of pleasure ran up the dormant equine's spine. Looking down on his own body, Sam saw how his shaft disappeared under the pleated skirt, re-emerging at steady intervals as the cat riding him moved up and down along Sam's member.

The blonde feline swiftly changed his rhythm after a short while, now slamming his ass down on Sam with more force and speed, again leaving his equine partner completely breathless. He started wildly bounce on top of Sam, repeatedly swallowing the throbbing donkeycock with his back door, his erection bulging out the front of his uniform skirt. Meanwhile, the cat's insides squirmed around Sam's length, rubbing and stroking the big cock from all sides, milking it as if hungry for the virgin equine's cum. Sam did quite a bit of squirming himself, as he was rapidly approaching his limit and was unsure of if he should let the cat know, that he was soon going to spew his seed inside him.

As expected, Sam didn't last very long in the fangs of the experienced feline, and less than a minute from starting he could already feel his shaft getting ready to unload into the other male's hole. He voiced a somewhat helpless whimper as the pleasure took over his lower body, his testicles contracting and shaft throbbing when the donkey finally reached his orgasm.

"Mmmmmmmmhhh~" The cat on top of Sam purred, slamming his hips down one final time to completely swallow the equine erection in his bumhole as the donkey seed began filling up his rectal cavity. "You virgins always cum so fast..." He muttered as Sam's cock pumped the last few ropes inside the feline's rump, concluding their male on male classroom mating.

The cat didn't waste any time basking in the nonexistent afterglow and quickly stood up from Sam's lap, a streak of cum immediately starting to trail down his left thigh. "Not that bad for your first time..." The feline said, whisking his blonde hair around a bit before stepping away from Sam's crotch. Supporting his upper body with his elbows, Sam now watched as the feline took a few steps to get closer to the laying equine's head, the erection behind his skirt easily visible from the low angle Sam was in.

Once next to Sam's head, the feline promptly crouched down on the classroom floor, bringing his bulging skirt just a few inches away from the long-eared equine's face. Sam looked up and saw the big and colorful eyes of the cat inspecting him from above. Despite full-well knowing, he was a male, and ignoring the fact they had just had sex less than a minute ago, Sam blushed lightly from the feline's curious gaze.

"Now that I get a better look at you, you're kinda cute." The cat said, grinning and tilting his head while resting his chin on his paws. "How about you try cross-dressing as well?"

Sam blushed to an even deeper shade of red, momentarily imagining himself wearing the girls' school uniform, before turning his face away from the smiling cat. It was not like the young donkey was particularly against it, but still cross-dressing in front of four other people he didn't even know the names of was a bit too much for him. Yet, upon looking for an escape route from his surroundings with a quick glance, it dawned on him that he was still completely surrounded by the other males in the room.

"It will be fun! Just relax and let us take care of you..." The cat whispered, and the other males started to close in on the donkey.

...

It all happened so fast, Sam only remembered bits and pieces of the hectic five or so minutes that followed. First, they had taken Sam up from the floor and stripped him naked of his male uniform. After admiring Sam's nude body and having giggled enough for the male donkey's shy reaction, they had dug out a pair of pink lace underwear from one of their bags and Sam hadn't resisted as they put the girly underwear on him. The matching bra they brought fit him just fine, but the panties were what caused the most concern for the embarrassed equine. The size was way too small and barely covered anything neither front nor back, only just managing to contain Sam's testicles, while leaving his semi-erect donkeydong hanging outside completely unrestrained. They had again giggled some more and taken some pictures, saying that it was fine and that Sam looked super cute with just the underwear on. Next up, they had dug up a redundant uniform one of them had, a girl's uniform of course. Again, it had been a bit too small, but they had managed to squeeze the confused donkey in it anyway. Then it was all nothing but a dash of makeup on Sam's face and they were done.

"OMG, that's so cute!" The snow leopard giggled, gently flicking the half-erect equine shaft visible from under Sam's skirt with his index finger.

"And now for the final touches..." The cat grabbed a couple of pink bow ties, attaching one to Sam's left ear and putting the other two onto his tail. "Perfect!"

The cat quickly took a picture of Sam with his phone, showing the blushing crossdressing newbie the results of all their effort. Sam was completely blown away by how cute he looked, at first not quite believing it was really him on the pixels of the smartphone screen. He had to take more than a few looks of himself before being convinced it wasn't just some convenient filter on the feline's phone.

"Cute, right?"

Sam carefully nodded his head, still feeling a bit embarrassed by this whole thing. The cat smiled.

"Nothing gets me as hard as cute boys like you crossdressing..." He sighed, his skirt twitching slightly between his legs. "Now we're all ready to start shooting!"

"What?" Sam's ears perked up as the cat dug out a proper video-camera from his bag, setting it on one of the nearby desks, pointing towards Sam.

"Just something small to commemorate the occasion. We were actually going to have a shoot anyway before you dropped in. Seeing how you're now here and already looking so cute, you might as well join us." The cat explained, carefully observing the mixed reaction from the cross-dressed donkey. "Are you perhaps uncomfortable with shooting a video with us?"

Sam quietly nodded his head, not knowing whether he should say something.

"Well, that's ok. That just means we got to persuade you then! Boys!"

Sam didn't have time to react and the Shiba and the snow-leopard quickly grabbed the donkey by the shoulders, forcibly seating him on top of a nearby desk. Despite looking so cute, they were surprisingly strong. As the two held the scared donkey in place, the dark-haired bunny walked closer, stopping just before Sam's legs at the edge of the desk. "Persuade him away, boys!"

Sam was beyond surprised when the dog and the leopard at his sides quickly leaned closer towards him, planting both their lips onto Sam's mouth, starting a wild three-way kiss between the three. They were pretty forceful with their advances, each of them pushing their tongues into Sam's maw and licking the insides of Sam's mouth with their craft tongues. All of Sam's will to resist melted away in a heartbeat, and he completely surrendered to the saliva-filled barrage of passionate and sloppy kisses he received from the two males next to him.

Meanwhile, the third of the males had crouched down between Sam's legs, which he promptly tore apart with the donkey putting up little resistance thanks to the oral assault over at his mouth. Pushing his leporid head under Sam's skirt, the bunny easily found what he was looking for, the tip of Sam's semi-stiffy directly in front of his face. Sam almost jumped on the desk upon feeling something wet on his tip, the male between his legs starting to kiss and lick the sensitive tip of Sam's donkeypole, producing sounds more lewd than the last as he went down on it.

"Keep persuading him boys, I'll start rolling!" Sam heard the cat say, but he was too powerless to voice any grievances. Plus his mouth was fully occupied by the Shiba-Inu and the leopard who continued their furious flurry of kisses.

"Hi guys, it's me again! Back with another cute video for you all today!" The cat started speaking like an overly enthusiastic PawTuber.

"Today, we have a special guest!" The cat continued, now bringing the camera closer to the other four, who were entangled to one another on the desk. "Isn't he cute? I don't know about you guys, but he gets me soooooo~ hard!" The feline now faced the camera downwards, lifting up his skirt to reveal his feline boner to the view. "This is actually his first time cross-dressing, so please leave a comment telling him he's cute down below!" He then brought the camera closer to take a close-up shot of Sam's saliva-covered muzzle, who the other two were still going to town on with their tongues.

"Ok, guys! I think that's enough persuasion!" The cat clapped his paws after setting down the camera and the bunny, Shiba, and leopard immediately stopped their tongues. The three then stepped away, leaving Sam alone in the middle of the shot, and Sam abashedly looked at the camera.

"Why don't you do a little spin for the camera?" The cat said, drawing a circle into the air with his fingers.

Blushing and trying to hold his skirt down over his erection, Sam stood up and did a hasty spin, showing the camera his outfit from all sides. "And now the underwear..."

Turning even redder, Sam slowly raised the top of his uniform, flashing the pink bra to the camera and the Shiba let out a flirtatious whistle. With his whole body shivering from embarrassment, Sam then lifted up his skirt, revealing his erect equine member which the pink underwear was too small to contain.

"You see that you guys?" The cat said, zooming in closer on Sam's cock. "That's what we're going to get to play with today." He giggled. "Who's first!"

The brown bunny was the fastest to raise his hand and was given the OK by his feline friend. He quickly took the stage before Sam, doing a twirl and also showing off his underwear for today. They were yellow and frilly.

The leporine male then moved over to the desk in front of the one Sam had been sitting on and stuck out his behind towards the timid donkey. He then quickly flipped the skirt over on top of his back, giving Sam a perfect view of his ass with just the yellow panties covering anything of the round, hazel cheeks. Lastly, the bunny reached back, slowly pulling down his underwear, now showing Sam his bare backside. His furry scrotum was also visible, a healthy-looking sack with a cute pair of testicles peeking at the donkey from below his cheeks. Sam's erection, wet with the bunny's saliva was twitching only a few inches away from the cute creature's furry furrow, where he obviously wanted the thick donkeydick.

"Awww... Looks like our newbie is a little shy, the cat said, quickly walking behind Sam, who nervously looked around himself. "Let's give him a little nudge, shall we?" Immediately upon saying that, the mischievous feline shoved Sam from behind, pushing him towards the bunny leaning against the desk in front. Momentarily losing his balance, Sam flailed his arms around for a brief second, falling forwards, slamming his palms on the same desk the bunny was leaning on, the tip of Sam's cock gently grazing the small, fluffy tail of the creature under him. "There you go!"

Sam accidentally glanced towards the camera, blushing and turning his face away from the imposing dark lens which recorded his every move. The shy donkey soon got something better to think about, when he felt a soft paw wrapping around the base of his shaft. Looking down, Sam saw that it was the bunny, who was reaching back with his left paw, taking a good hold of Sam's cock and now tugging it towards himself. "Someone's eager!" His blonde cat comrade commented, now moving closer to Sam behind his back.

The timid equine almost yelped out loud as he felt the feline grabbing his ass from behind, and pushing it forwards onto the bunny. Sam didn't actually have to do anything as the two worked together, the bunny guiding Sam's member onto his own hole, and the cat pushing Sam's hips from behind, sticking the equine erection inside the leporine's winking orifice.

Lubricated only with his partner's saliva, Sam's tip penetrated the tight tailhole of the young hare, making the slightly smaller creature groan in pleasure, as he got his colon filled with a grade A butt battering ram, a-la donkey. Just as with the cat, strong pleasure began immediately surging through Sam's loins, and the timid equine could feel his body heat up as a result of claiming his second ass of today.

Sam was almost surprised as his balls touched with the other male's and the cat now let go of his skirt-covered buttocks, leaving the two mid-penetration males to themselves, at least for now. "Well? How does it feel?" The cat asked, directing his question towards the animal with his ass wrapped around the big donkey meat.

"Mh~ He's certainly big... Still feels a bit like a virgin cock though..." The bunny answered, and Sam was sure he was grinning ear-to-ear, even though the donkey could not see his partner's face.

"Alright, you heard him!" The cat announced. "You need to shut him up! Show him that you don't fuck like a virgin!"

Awfully flustered by the sudden pressure, Sam looked down at the buck below him, feeling the bunnyhole contracting around his erect member. Twitching his long ears nervously, Sam gently pulled his hips back, and carefully slammed them against the rabbit-rump in front of him. "I know his ass isn't quite on-par with mine, but I'm sure you can do better than that." The cat mockingly said, gently spanking Sam's rear.

Again, the grey equine retracted his hips, this time, slamming his cock back into the rabbithole more aggressively. Sam himself gasped in surprise at how good it felt, and the bunny anus seemed to agree, tightening along the entire length of the equine shaft. "Feels good, doesn't it?" The cat whispered right by Sam's left ear, almost making the shy equine jump out of surprise. "Just do it even harder this time, and I'll promise it will feel even better."

With the growing lust boosting his confidence, Sam wound his hips back yet again, smashing his crotch onto the bunnybutt with almost full force, his equine testicles audibly slapping against the hare's. His partner now also reacted, his ears momentarily perking up and pointing towards the roof, soon falling limp again as the shock subsided. "Again!" Sam did as he was told, repeating the motion of his hips, feeding his rod to the tight boyhole in front, shivering with pleasure as the other male tightened around his cock. "Again!"

But Sam didn't need to be told what to do from that point on, as the equine's reproductive instincts kicked in and he started properly fucking the hole offered to him. Sam quickly forgot about the fact that he was having sex with another male, and just went full-send on the bunny ass in front of him. The small, lewd sound from their lovemaking slowly started filling up the quiet classroom, the three others enthusiastically watching on from the sides as Sam hammered his cock down their friend's hole.

The Shiba and the leopard soon decided they were bored to just watch, and started making out, swapping sloppy kisses with one another in the background as Sam pounded the crossdressing bunny. Each of their erections already poking out from underneath their skirts, they promptly grabbed each others' cocks and started stroking while exchanging saliva between their locked lips.

"Aww~ I'm feeling totally left out here you guys..." The cat said, pouting towards the camera. "That's ok... I guess I'll just be having fun by myself then!" The feline raised his voice, slapping both his paws onto Sam's skirted backside.

Sam twitched from the other male's touch but was unable to stop his shaking hips from pounding away at the bunnybutt. He could feel the cat's paws groping his cheeks from above the skirt, as the feline explored Sam's ass in a rather rough manner. It took him no time at all, to slide his paws under the skirt and start groping and fondling Sam's bare bottom, his claws making rounds on the soft boymounds, playing with the lining of his pink underwear, and running up and down Sam's pink-cloth-covered crease. It actually didn't feel that bad, and besides, Sam was getting close to busting a nut in the bunny's rear, that his regard to other things happening to, and around him, was very minimal at the moment.

He was a bit surprised however when he felt the feline's fingers grabbing onto the sides of his skirt, and pulling the navy-blue legwear down in a flash, exposing Sam's buttocks for the whole world to see. Sam was even more surprised, when the cat promptly buried his face into Sam's donkeyrump, pressing his nose into the panty-covered furrow and moving his muzzle around in the crease. Sam could feel the feline's breath through the thin fabric, the flow of air tickling his covered tailhole, and sending shivers throughout his lower body. After a short session of rear-side motorboating, the cat retracted his smiling face from Sam, now licking his lips with his eyes still fixated on the pink panties on donkey's moving hips.

Now, it wasn't that big of a surprise when the feline expectedly pulled down Sam's underwear, removing the thin cotton contraption from covering the equine's cheeks. If he wasn't pistoning his cock into a tight bunny tailhole, Sam would've probably been very worried as the blonde cat now spread out Sam's ass, getting a good and proper look at the equine's twitching pucker hidden between his cheeks.

The cat stood up and Sam could faintly hear another piece of clothing hitting the floor, and the donkey also had a pretty good hunch of what it was. Indeed, the cat had removed his own skirt, the uncut cat-erection now fully visible to the camera, to which the feline eagerly presented his member, playing with his foreskin and winking at the lens playfully. After the brief introduction, if you could call it that, the cat crouched down over to his bag and dug out something Sam wasn't quite able to see. But it soon became clear to him, what the feline had picked up, as something cold and slimy dripped into his exposed crease.

"The most important thing for cute boy love is proper lubrication!" The feline chimed, spreading the cold lube all over Sam's hole, even sticking his index finger up and inside Sam's virgin tailhole. Sam flinched as the furry feeler entered his shitter, but breeding the bunny was still the highest priority for his lust-filled brain, and he didn't stop or slow down his hips. The cat pushed his slender finger all the way in with one go, eagerly exploring the untouched insides of the moaning equine, pushing and poking the squishy anal walls of Sam's hole. To be completely honest, the strange new stimulation to his unused backdoor actually pushed the already close-to-orgasm donkey even more towards his limit and Sam didn't know, how much longer he could hold back from nutting inside the smaller male.

Giggling to himself, the feline promptly removed his finger from Sam's tailhole, causing the crossdressing donkey to flinch again as his rectum was allowed to contract to its normal size. "Such a cute little hole~!"

The anticipation of getting his ass penetrated by the cat, combined with the steady stream of pleasure provided by the plump bunnytush wrapped around his cock was proving to be too much for Sam, and the panting donkey was ready to blow his load at any given second now. The tip of the feline cock now firmly pressed up against his entrance, Sam thrust his shaft as deep into the bunny's fun-tunnel as he could, at the same time feeling his lubed up orifice getting stretched out by the cat's hard and warm malehood. Sam tensed up his entire body, vividly sensing how a decently-sized cock slowly slid its way inside his ass, as his own shaft throbbed in the tight grip of another male's tailhole.

Sam's heavy testes twitched, quickly contracting towards the grey equine's body and Sam couldn't help but neigh loudly in a donkey-like fashion as he achieved climax, sandwiched between a cat and a bunny. A strong and fierce pleasure shook the young donkey down to his very core as he ousted his hot load inside the bottoming bunny's rectal tunnel. Rope after rope, his cock spewed out cum, filling up the other male's stuffed tailhole to the brim with seed, the excess leaking out and dripping down onto the classroom floor.

It seemed that all the while Sam had been having a rectal romp with the bunny, his partner had been jerking himself off unbeknownst to the donkey, and now achieved his own climax just after Sam, eliciting a rather lewd moan as he stroked himself to completion while getting his hole filled with cum. "Fuck..." Sam heard the bunny groan as the bred animal carefully wiggled his behind, sloshing the donkey's load around inside.

Behind Sam, the cat purred, his raw, uncut member now fully within the tight grip of Sam's virgin donkeyhole, which didn't quite know what to do with the foreign object between its walls. The cock itself wasn't that big, but for Sam, who had never really had anything up his butt before, it felt pretty big regardless. The young donkey could feel every twitch and throb of the feline cock in his colon, the uncomfortable feeling of the unnatural anus-stretching slowly subsiding as his ass gradually adjusted to the object inside it.

The cat sighed, looking greatly satisfied as he ran his paws along the curve of Sam's back, all the way up to the equine's shoulders and back onto the springy, grey buttocks down where his cock resided at the moment. "You two came already? Such a shame..." He muttered, a hint of sarcasm in his high-pitched voice as he spread out Sam's cheeks down below, to get a better look at where he was connected with the male equine.

"Imagine..." He continued with what almost sounded like a whisper. "...Losing your virginity, and anal-virginity on the same day... What a lucky donkey you are..."

The mischievous feline carefully moved his cock within Sam's fun tunnel, the surprised donkey straightening out his back and perking up his long ears as a sharp sensation ran up his spine. "Mmm~ You felt that didn't you..?" The cat muttered, again, whisking his long blonde hair over his shoulder and continuing to move his dick inside Sam's squirming tailhole. "Fuck, you're tight..." He groaned under his breath.

Now focusing all his attention on the ongoing assault on the nerve-endings on his back-door, Sam barely even noticed the brunette leporine retracting his hips underneath the donkey. Only the audible splash of his seed escaping the bunny's hole hitting the floor, and the sudden coldness on his shaft giving away that the first male had pulled out Sam's cock from his hole. But the young donkey was left with almost no time to even process the events by his groin as a sharp sensation quickly reminded him of what was going on by his hole. "Do you like it?" The cat whispered, leaning his torso closer to Sam, running his mischievous paws up the shirt of Sam's female uniform, grabbing the male donkey's chest from behind as he ground his hips together with Sam's. Sam wanted to moan, but only a feverish gasp dropped off his lips. "Trust me..." The cat purred into Sam's ear. "...It's about to get even better~"

The young, brown-furred hare just managed to seat himself on one of the desks, as the cat suddenly shoved Sam forwards, bending the young donkey over, almost to the same position Sam had been fucking the first male. Surprised, Sam glanced up at the face of the buck he had been fucking, gazing up from between the equally surprised leporine's legs while his cat friend took a proper grip on Sam's hips and tail.

There was a thump and Sam was seeing stars for a while, the strong sensations of mixed pain and pleasure getting carried out from his rectal area, and rapidly spreading throughout the donkey's slender figure. By the second thump, Sam moaned loudly as the feline cock in his colon got pushed even deeper inside his virgin ass, digging its way through the resistance of Sam's anal mucosa. "Ahh~ That's the stuff!" The cat groaned, his tone momentarily slipping to a more masculine one, before he corrected himself to his usual, more high-pitched, and girly tone. "Nothing like..." The cat thumped his hips against Sam's ass. "A good... " Another one Sam's equine moans echoed in the classroom. "Virgin..." The cat gave a semi-harsh spank to Sam's left buttcheek while tugging on the limp donkeytail. "...Ass!"

Sam quickly had to support himself against the desk with his hands when the feline conducting rectal exploration on his hole got serious, starting to pound the whimpering donkey from behind at a pace of a rutting dog. Despite his cute outer appearance and somewhat delicate manners, the blonde feline was anything but gentle with Sam, hammering his cock in and out of Sam's hole frenetically, fucking, well... like a real male.

On the receiving end of the fierce thrusts and aggressive pounding, Sam had the weirdest semi-chub of his life, his body still not properly decided on whether the donkey truly liked this or not, but for sure it was slowly getting there. Having been quite tense at the time of the penetration, the steady rhythm getting beat to his backside by the cat as well as the gradually growing amount of pleasure radiating from his packed colon, helped Sam relax a bit more, which in turn helped produce more pleasure as the feline member explored the depths of Sam's rump. And it truly was a matter of time before on one of the jabs, the tip of the feline funstick found the young donkey's g-spot, and Sam couldn't help but moan from the strong pleasure from the stimulation of his previously-untouched prostate.

The brunette bunny sitting in front of Sam grinned while looking down at Sam's red and ecstatic face. The smiling leporine soon laid back on the desk, resting on his elbows while looking at his friend fucking the blushing donkey. "Damn, you made a real mess down here didn't you?" The bunny suddenly said, laying on his back over the desk and craning his head to look down at the splattered semen all over his backside. "Well, you might as well help cleaning it up."

The coffee-colored leporine raised his legs up towards the roof, grabbing the back of Sam's head with his paws, and pulling the surprised equine's muzzle directly onto his cum-smeared hole. The hare's hazel nutsack now resting on top of Sam's face, Sam looked up at the male in confusion as the smell of his own semen filled his nostrils. "Clean up!"

Easily deducting he was not in much of a position to argue, the shy equine cracked open his lips and the salty taste of cum immediately flooded his mouth. It didn't actually taste all that unpleasant, also given that Sam had other things to think about, the most prominent one being the feline cock shoved down his cramping hole. Opening his jaws a bit wider Sam slowly pushed out his equine tongue, catching a good wad of cum onto it from the bunny's crease, retracting it inside his mouth, and swallowing the salty liquid along with his saliva. Sam stuck out his tongue for a second time, now taking a longer, and a stronger lick of the leporine furrow, his rough, long equine tongue making contact with the hare's anus as it scooped up more cum.

Sam noticed his partner twitch and gave the exposed rabbithole another lick, exerting even more force around the leporine's hole, now hearing the bunny moan as a result of his tongue-movements. Now sporting a full-on erection, lust creeping back up at the back of his mind, and curious to hear what other kind of moans the hare could make, Sam just decided to go for it.

Pushing his tongue up against the soft ring of the bunny's anus, Sam easily overcame the frail resistance of the leporine hole, thrusting his tongue directly inside the long-eared animal. "Wwh-wh-whooaAaaAA!" The bunny moaned, his legs and ears twitching as Sam started licking the insides of his hole. "Didn't even have to tell him... The kid's a fucking natural at eating ass!" The young buck chuckled, pushing Sam's face deeper into his crease, greatly enjoying the grey equine's rectum-cleaning-service. "Fucking clean the insides of my hole!"

Seeing the donkey give special attention to their friends, the Shiba-Inu and the snow leopard soon came over as well, both positioning themselves on each side of Sam, pointing their erect dicks at the helpless equine. His head dizzy from swallowing so much semen, Sam didn't put up any resistance and just lazily grabbed both of their cocks and started stroking. Both of them were about the same size, slightly smaller than Sam, cut and leaking pre, their owners quietly moaning as Sam jerked them off while getting fucked from behind. The bunny also began jerking himself off as the young donkey continued giving him the tongue-treatment.

Servicing all four males at once, Sam was steadily working his way towards his third orgasm. His equine dong had again been erected, and it swung up and down below his abdomen at a pace dictated by the feline behind him. Sam was already very close, especially considering how his rock-hard erection itself hadn't received any sort of stimulation whatsoever, the rapid prostate smashing being the main cause for the young equine's arousal. Speaking of which, the feline humping Sam's hips had decided to pick up the pace, working his cock into the loosening donkeyhole at a rapid pace, the throbbing of his feline shaft indicating that he neither was that far off from cumming into Sam.

Was it from being tired from cumming twice already, or eating out another male's tailhole while stroking two dicks, while getting railed in his own buttpipe, but Sam strangely found himself craving for the other males' cum. Being a day of many firsts for the young donkey, he also wanted to feel cum rushing into his hole for the first time, as well as maybe getting a proper facial from the two gentlemen whose cocks he jerked just a jew inches from the face he had buried in the fourth male's ass. This lust, this pleasure, it was all so addicting, and Sam didn't know why.

"Ok, here it goes!" The cat muttered under his heavy breath, launching into a final frenzy of thrusts, humping Sam's butt with all he could muster.

Sam moaned in the brunette bunny's crease, feeling the feline cock throbbing between his walls as if the shaft was getting bigger. "F-Fuck, I'm close too..." The fapping hare grunted, shoving Sam's face deeper between his cheeks while stroking his cock faster and faster. It went without saying, that the other two were not far off, each of their bodies twitching and jerking, restless moans escaping their gaping mouths as Sam's hands worked them closer and closer to climax.

'Here it comes!' Sam thought, not quite knowing if he should feel horny, or scared as he closed his eyes at the brink of his own orgasm.

"Meooow!" Echoed inside the classroom.

Breathing out a wavering sigh, the cat dug his surprisingly sharp claws into Sam's cheeks, finally ejaculating inside his ex-virgin partner. Sam's whole body shuddered as the pressure inside his colon changed, most of the empty space in his tight rump getting occupied by the sticky, hot liquid as he experienced his first-ever anal creampie.

Sam hastily retracted his mouth from the masturbating bunny's hole gasping for air as the unfamiliar warmth of the feline's seed spread throughout his loins. The squirming donkey didn't even get a chance to moan properly, as now, something warm and sticky splattered onto his face. Mouth still agape to breathe, Sam watched up in front of him, where the bunny held his orgasming cock with both paws, shooting thick ropes of cum into the air, which went on to land directly onto Sam's flabbergasted muzzle. And before the leporine was even done cumming, Sam felt another splash of cum coming from his left, now being the snow-leopard's turn to cum, his semen splattering onto Sam's cheek and mouth, one particularly fiercely shot rope managing to stick itself to the donkey's ear. Already expecting it, Sam turned his face towards his right, receiving almost point-blank cumshot directly over his nostrils, getting long streaks of cum shot all over his muzzle by the Shiba who moaned erotically as he came.

Receiving three loads on his face at once, as well as one up his shitter, all of Sam's senses were easily overwhelmed, and the young equine came onto the classroom floor, the seed jetting from the tip of his cock reaching a good three feet in front of him. This orgasm was different from the other two and it felt even more amazing than either of those, Sam's equine shaft throbbing enthusiastically between his legs, hoping that it would have something more to fire off for such a mind-blowing orgasm.

The classroom, which was quite noisy just a moment ago, suddenly became quiet, the only audible sounds in the open room being those of all the five young males breathing, as their breaths began to settle in the aftermath of their in-school-group-loving. A happy-sounding tune played itself through the intercom, echoing around the entire school and classroom. It was the five o'clock bell. The school building was about to be locked for the night.

"Oh shit! We need to hurry! The janitor starts locking the classrooms from the third floor." The cat hissed, being rather uncourteous with his pullout from Sam's stuffed hole.

Sam was still in a complete daze, now sitting on the floor, blinking his eyes, cum splattered all over his head, and some more leaking out from his backdoor. He sluggishly followed with his eyes as the other males quickly took out wipes from one of their bags, quickly cleaning their softening dicks and wiping off any cum that had splattered onto the floor. Sam also noted the cat turning off the video camera and quickly stuffing it inside his back before helping the other three with the cleanup.

"Fuck! FUCK! We should've brought condoms!" The cat growled, wiping up a big puddle of Sam's donkeyseed from the floor.

"Well, it was your idea to seduce the new guy, genius!" The Shiba snapped back at the feline with a rather masculine tone, the cat responding by showing the canine his middle finger.

Sam flinched as a bunch of wipes were suddenly dropped down onto his muzzle. Picking the white cloth pieces, Sam watched up at the bunny who stood next to him. "You better start cleaning up, unless you want to get caught." He said, handing Sam the pink panties from the floor. Snapping back to reality, Sam immediately began wiping his face with the wipes, using one or two to clean up his shaft and tailhole, swiftly slipping on the feminine underwear just as the other males were finished with their cleanup.

"And now..." The leopard muttered, taking out a can of air-freshener from his bag and spraying the strong scented chemical a bit all over the classroom, covering up the pungent smell of cum currently residing in the area. Just as the spotted feline put the cap back on the aerosol can and stuffed it in his bag, the classroom door was opened and a middle aged bulldog janitor stepped into the room.

"Ah! It's you again! What have I told you about hanging out in classes after school!? Get out of here before I rat you to the principal." He said with a grim expression.

"Lol, soz! Won't happen again!" The cat said with a wink, grabbing Sam by the hand and leading the entire group out of the classroom.

The sun was starting to set, casting its orange rays into the hallway along which Sam walked with the four crossdressers, of who he didn't even know the names of, and with who he had just had sex inside the school. None of the group spoke a word as they walked and there was some awkward tension between Sam and the rest, which persisted all the way to the school gates, where they were to part ways.

As the group split, the cat grabbed Sam by the shoulder, looking directly into the flustered equine's eyes. "What just happened in there doesn't reach the teachers, ok? We'd all be in whole lotta trouble if this got out." He said with what Sam assumed was his normal voice, which admittedly still was pretty feminine. The donkey quietly nodded his head.

"Excellent!" The cat said with a smile. "We should totally hang out again someday. Add me on Tailster #CDSlut_Feline21." The feline winked before turning on his heels. "Oh, and you can keep that outfit by the way. It suits you well..." He said facing away from Sam. "Well, later then!" And just like that, the cheery blonde feline was gone.

Still in his female uniform, Sam immediately dug out his phone from his bag, opening Tailster and searching for CDSlut_Feline21. "This profile is marked as NSWF. Are you sure you want to proceed?" Was soon plastered on his screen.

Deciding it would not be the best to view the profile out in the street, Sam locked his screen and stuffed the phone back into his bag. A gentle breeze tickled Sam's exposed thighs under the skirt and the young equine suddenly felt a lot more exposed than usual, which he kind was with wearing only the skirt and panties underneath. Already hoping to switch back to his casual clothes, Sam started walking towards his house.

After a few minutes of walking, the deep-in-thought equine twitched and muttered: "Ah...! I forgot to ask about the video..."