Espy: Tales of a Femboy

Story by Vulpsis on SoFurry

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#1 of Espy:Tales of a Femboy

Espy is forced to go to school while wearing a schoolgirl's outfit due to his grandma's mistake. After being mocked and tormented by his classmates he goes to the washroom and finds himself cornered by a couple upperclass men...


"You look like such a pretty girl Espy!"

"awww look at the sissy!"

"Sorry Espy, you can't sit here. Boys only!" Espy's pink face was blushing a vivid red. He held his school text books against his chest while he passed his peers whom were already in class. This was the first day of high school and Espy was wearing the girl's uniform instead. His classmates all wore jeering faces while laughing at his outfit. it was obvious that Espy wasn't having a good day at school, it was his first day living with his grandmother and already things were hectic. His grandmother didn't have the greatest sight so when she went to buy his school uniform for the year she accidentally bought him a girl's uniform. Now he was stuck wearing a girl's skirt and white uniform shirt, it wasn't even the right skirt since his tail popped up with the skirt lifting it a tad bit. His panties would expose themselves if he forget to keep his tail between his legs.

"It's just for one day..." he said to himself. He wanted to stay home but his grandmother would not hear it. She said she'd go buy him the right uniform but he still had to go to school.

"It'll build character! Besides a young Espeon like you would look cute in anything!" she said. The moment he sat down a Luxio turned around in his seat and flashed a smile while raising his eyebrows in a flirtatious manner.

"So... Wanna go out to the movies... Baby?" the class was in an uproar. The smallest joke, regardless if it was funny or not, made the class laugh in unison. The noise of the class even reached the emptying halls prompting unrelated students and staff to peak in to see what the hubbub was about. This all went on until their teacher, a scruffy Hypno, walked in.

"Alright class... Settle down. Espy... What in Arceus' name are you wearing?" The class snickered once more while Hypno himself had to turn around to hide and stifle his own laughter.

Class went on as usual. Nobody made any noise or jokes for the first hour during History. It was a double period so Espy was relieved, he was sure they were over it... Until a crumpled piece of balled up paper came flying and flicked his ear. Espy flinched, scared at the moment since he was deep in his thoughts until he realized the paper landed on his desk. He grumbled before unfolding the paper.

A cute girl like you should go on a date with me! - Gerard.

Espy looked over and saw his classmate Gérard, a Growlithe, along with his pal a Poochyena. Gérard made kissy faces which made Espy blush and grimace. He simply ripped the paper in half... He wished this day would be over.

Midway through class Espy had another predicament. He really needed to pee. He had been holding it in to avoid running into anybody else but now he couldn't hold on much longer. He raised his hand to get his teacher's attention while he read out loud the history of anthropology and evolution.

"yes... Espy?" he asked, his eyes focused on him while his reading glasses slid down the bridge of his long yellow nose.

"Teacher... I really need to use the washroom..."

"Lunch is in half an hour. If you can hold it until then..."

"Teacher... I can't..." He whined while twisting his legs in agony to hold back the floodgates. Hypno rolled his eyes before raising a finger and using psychic to hover the hall pass to Espy.

"Be quick"

"Make sure you use the lady's room!~" One of the boys teased. Blushing, The Espeon quickly ran off.

When he reached the boy's room he nearly fainted. There a white sign hung *Out of Service. Please go to Basement* however the basement was 4 floors down and he knew he wasn't going to make it. Cursing, he slowly walked up to the lady's room.

"Maybe they won't notice..." The Espeon said to himself. "Maybe it's empty...and nobody would come in..." he shook his head though. "C'mon let's just run to the basement...it's embarrassing enough to be wearing this outfit!" But then a small squirt of pee trickled out and he knew he didn't have time. Slowly he opened the door and quickly scanned the porcelain white room to see if it was empty. The coast was clear and he ran into one of the stalls. He didn't have time to close it, he just lifted his skirt and lowered his panties. He sighed as the warm stream of urine hit the toilet, the satisfying sound of piss hitting water filled his ears and made Espy smilled, feeling content and relieved.

The stream didn't even finish when the door slammed open. Espy panicked and accidentally dropped his skirt down trying to close the stall door behind him.

"Oh no!" He cried out in frustration while his ears perked up and pick up the sound of two older boys stumbling in while laughing.

"Dude, Casino would never check here!"

"Shut up dude! Someone's here!" The stall door swung slowly open and gained momentum, exposing Espy, his private and piss soaked panties.

"The fuck? Why are you dressed as a girl?" asked a Mightyena.

"And why are you in the girl's washroom?" added the Houndoom. The two wore the khakis and white dress shirt that was required but they also had the senior emblem designed in front of the pocket.

"I I uhm..." Tears began to well up in his embarrassed eyes. "I'm sorry!" Was all he shouted before lifting up his wet panties. He was about to rush out until the Mightyena stretched his arm and blocked his path.

"What's the hurry, sweetie? We won't tell anyone who you really are... Hunter?" the two were now smirking while Espy can feel their pervy eyes detailing his every feature. hunter, the Mightyena, went over and locked the bathroom door.

"No... Please..." Espy muttered while the mightyena forced himself into the stall with Espy.

"Turn her around already, Max. I wanna see that fine ass again!" Espy squeaked when Max the Houndoom grabbed him by the wrists and pulled him out of the stall while turning Espy around.

"You're a sophomore... Right sweetie? That means today you should have been learning about the history of evolution... Interesting subject..." Espy tried to fight back and pull away from the two... But Hunter quickly swooped in and held his legs down.

"H-Hey! Let me go!" Espy shouted. He tried to kick the Mightyena away but Max covered his mouth and shushed him, his muzzle rubbing closely against the Espeon's pointing ears before giving them a hot, wet lick. Espeon shuddered from the ticklish sensation, his little body quivering in their grasp from both fear and embarrassment.

"See... Thousands of years ago a bunch of us were still walking on four legs. We also could breathe fire, shoot water and were capable of harnessing more potent psychic power... Today we can merely cough soot and can only lift small objects... But some of our more feral instincts lingered as well... " Espy didn't know what the point of this lecture was. He wriggled in place when Max began to run his hand underneath Espy's shirt and run up along his back... Right above his tail.

"uwaaah... Stop that!" He said, his voice muffled by the Houndoom's hand. Espy's rear began to raise up from feeling Max's firm hand rub and tickle a sensitive spot that made Espy move on his own. Espy didn't understand what was going on, he felt like a marionette being controlled by the skillful strings that Max possessed.

"For instance... Some of us like me and Hunter there are descendants of canines... But you came from the Eeveelution line... You have traits of dogs, bunnies and... Cats." Espy's panties began to tighten, his pink face had a crimson red streak across his face while he practically bent forward and was leaning over for them now. Hunter finally let go of his legs only to lower his stained panties. (What's going on... why am I getting excited?) Espy though to himself. His legs were free now, he should be to kick them and run away... but his legs felt like rubber noodles. Hunter's hand ran up across the pink soft fur that his exposed leg possessed which only made Espy quiver and shake in anticipation. (Why do I... like this?) Espy wondered.

"SHE had an accident, Max" Hunter said while adding emphasis on the word 'she'. "We should really clean her up..." He added while his hand traveled to caress Espy's plump rear. Espy squeaked, his tail wagging for a moment. (Maybe... I am a girl...) He thought to himself. He didn't know what girls had underneath, he was still innocent in that regard. He lived a sheltered life before his parents passed away and nowhe lived with a possibly senile grandma.

"I know how to make pussy purr... And your little boy pussy is going to be purring for me from now on..."

Espy tried to cry out help but no one heand him yell. His screams echoed loudly in the washroom but the tightly sealed door muffled his pleas that only made it to empty halls. Espy's back bent forward while Max continued to rub at that sensitive spot. His finger was lubed up with the hand soap the dispensers pumped out. Max grew annoyed by Espy's yells and jammed a hand against his mouth to shut him up. Hunter took the moment of silence to step out and switch the out of order sign before closing and locking the door.

"okay dude, we're still good. " Hunter informed his partner.

"okay, good..." Espy muffled something against Maxs hand before Max pulled his head back, forcing Espy to stand up with his back still curving from feeling those nerves being rubbed. "Alright... Found it..." He muttered. Espy didn't know what he meant until his body suddenly shot up. His ass clamped up around Max's finger which curled up inside his flesh. "I'm about to show you just how much of a girl you really are!" Espy moaned and gasped while Max's finger began to rub along a ticklish area inside his ass. Espy's penis began to swell up and rise from the lowered panties. Hunter mocked him, Espy beginning to tear up from feeling so lewd and exposed to the two. Max's black finger slicked in and out, the perverted noise of the slippery soap slicking inside his narrow tunnel echoing and playing back in Espy's large ears again and again.

"Bend her over dude, I'm getting hot!" Max only snickered, his finger creating slicky noises while massaging Espy's prostate. He lifted up the hand that covered Espy's mouth and pushed his back to bend over the femboy all the way. Espy's ears flayed back when his cold, wet nose picked up an unfamiliar scent. Hunter had unbuckled his belt and pulled out his great red shaft. Espy stared in wide eyed surprise, he had never seen another boy's private like this... and the way it pulsed and throbbed with life made Espy curious. Why was Hunter's private so much bigger? Why did it swell in the bottom as well? His pondering was interruped though when Hunter's hand grabbed the back of Espy's head, pulling him closer to the throbbing flesh. Espy wanted to pull away... Or at least he thought he wanted to... But something about that musky scent made him curious. The potent stench gagged him at first but soon he felt intoxicated by the thick bitter scent. The scent felt like a heavy gas that coursed through his body, his legs wobbled some more while his head grew cloudy. (He's so big...) His eyelids grew heavy, his rear raised higher while his back curved some more. Hunter ruffled his head affectionately while looking down on him with a mischievous smile.

"You like that smell... Don't you sweetie?"

"Even further proof that you're a little faggy sissy girl..." Espy felt that familiar sensation of wanting to pee... but this time it was different. It was constant and every time Max's finger bumped and proddd against that sensitive spot deep within Espy felt the urge spike. But he now felt a different urge... he wanted to feel that throbbing flesh. He wanted to feel it inside his pussy... his boy pussy. His lips twisted with uncertainty before he gave into the instincts that heavy musk drew out andreached out with a delicate and fragile hand to feel that mightyena member.

So hard... So warm... He just wanted to taste it... His saliva was building up now... He had to..

Espy's small pink tongue dragged along the shaft while his hands reached out to pull down his pants and expose his furry grey orbs.

"You like how that tastes... Don't you... You little sissy?" It was salty, bitter and strong but Espy loved it... or at least he thought he did. The stench threw him in a foggy state, it felt like his mind was lost in thick misma and the only guide were these two men. Espy noddedhis head and looked up at Hunter with innocent watery eyes. "you're so fucking cute..." He growled. Hunter pulled back his cock and raised Espy by the chin. The Mightyena's face was blushing as well before he leaned and pressed his lips against Espy's. Espy was utterly shocked, his eyes widened once more before the fell halfway, his mind and body clogged by the male's masculine scent. Espy's hands pressed against the Mightyena's chest as Espy stood on his tippy toes to kiss back, Hunter's tongue was noticably larger and overpowered Espy's. It coiled and trapped the bitter tasting tongue and tasted every inch inside of him. (He's kissing me... and I'm kissing back...) Espy thought. When they broke their kiss Hunter gently guided the femboy down who obliged and went back to grabbing and kissing his dick as well. (How do I know what to do?) Espy thought to himself as he began to suckle the tip and cradle the balls. (Are these my real instincts? I am a girl...)

"Damn it... Now I can't hold it in... " Max pulled out his soapy finger before unzipping his pants. He pulled them down along with his underwear before gripping at Espy's sides. " You're about to lose your girly virginity... "

Espy's body rocked back and forth. His panties remained lowered and clug between his knees while his skirt hung in the air, swaying with each thrust made and blocked the view of his little pink member that leaked with pre. His hands gripped around Hunter's legs while his mouth wrapped tightly around the mightyena's member. At the other side Max's strong hands gripped around his hips and pulled him back repeatedly while his canine member Perpetrated the sissy boy again and again.

"Such a fucking tight pussy we found..." Max grunted while a hand rubbed up along the area above Espy's tail. Espy whimpered, his ass reflexively raising as high as possible while he slobbered all over Hunter's dick. Every thrust Max made filled Espy with a hot burning warmth. He felt the slimy tip pound against that spot and bringing out a foreign pleasure that made him squeak and moan involuntarily... it just felt too good.

"Look at her... She loves cock so much! What a nasty little girl we found..." The thapping sound of Max pounding his ass defended his ears. Each thrust stretched his little boy pussy out and made him writhe and moan in its. Hunter's cock felt so warm and say in his mouth and the creamy seed that oozed out was like an earned reward. Max's cock felt hot by comparison and rubbed along and pounced every little ticklish nerve that made Espy's little cock twitch and swell with excitement. For the longest this kept up, Espy occasionally gagged when he took too much of Hunter inside him, but he wanted to take it all in. He tightened his grip on Hunter's legs and went forward, his cold wet nose burying in the light grey fur that mightyena are well known for while Max's thrusts made it seem like Hunter was fucking his throat as well.

"Dude.. I'm about to cum..." Hunter grumbled. Espy's pointy ears twitched while his lithe tongue swirled around the tip. Wanting to make him feel good Espy began to bob his head faster, his mouth sucking and slurping harder.

"She wants her milk... Give her plenty to drink!"

"shit... She's too much... I'm gonna..." Hunter surprised Espy when he pulled out but Espy soon figured out why. Ropes of viscous white cum shot against his face, a squirting accidentally blinding one of Espy's innocent eyes while rh the test coated his pink furry face. Max saw this in the mirror and felt that climactic urge build up rapidly. He pulled Espy in close and pounded his boy pussy rapidly, Espy's cries now rising higher in pitch. Espy stood up, unable to stifle his voice when Hunter raised his finger and shushed him only for Max to pull him in close and muffle those girly cries with his own kiss. Nothing surprised Espy now and he kissed back, loving that spicy hot sensation of a houndoom's tongue overpowering him and tasting his mouth. Max didn't seem to mind that Hunter's taste linger... or maybe he loved it even more because of that. Espy didn't know, his body was too hot and bothered to think. He felt Max's hands slip underneath the shirt and rub along Espy's slim and soft furry pink chest while he fucked him hard and faster. Finally he gave one last powerful thrust before he emptied his hot cum right into the sissy boy's ass. Espy cried out, his pussy feeling so good as the warm milk coated his ass and face...

Max pulled out and admired the cream pie he just made. Espy fell onto the floor, the skirt covering nothing while his cum soaked ass and face was fully displayed.

"You should really wash up... Can't go to class smelling like dick you know..." Max reached down and offered a hand to the fallen Espy. For the first time Espy smiled and was about to reach out until an abrupt knocking noise startled the three.

"Espy?! Are you in there? What's taking you so long?"

"shit, it's Mr. Gnosis!" Max whispered before scrambling to the window. He jumped out of his pants and underwear before slipping the pants back on and holding onto his underwear in hand.

"That Hypno?!" Hunter asked while he helped Max climb out and reach a tree branch nearby.

"Yeah... Hey! Girly boy! Don't tell him what happened! Wash up! here! " Max threw the underwear at Espy before helping Hunter out the window as well. Espy struggled to get up, his rear still aching from the pounding he received. He reached the sinks as fast as he can and began to wash and scrub his face with soap and water. He heard keys clanging while Mr. Gnosis complained about the number of keys. Without much thought he threw away the pee stained panties in the nearest trash can and quickly slipped on the underwear before the door swung open. There Mr. Gnosis looked directly at Espy who froze on the spot. Fear, guilt and shame quickly swelled up at once.

"Espy?! What's wrong?" Espy said nothing. He felt the first wave of fresh air blow into the bathroom from both the opened door and window. That was when his head finally cleared up and he realized what happened. Tears began to well up while Espy's head hung in shame. He felt dirty now, used, and most of all scared.

"I-I'm sorry... T-Teacher..."

"Espy! It's alright! I understand you just wanted to hid-" Mr. Gnosis paused when he stepped in and noticed the panties in the garbage can. His eyes then trailed down and saw a thin yet evident trail of white fluid. And to top it all off the stench in the washroom didn't smell like a bathroom... no it was a scent that Mr. Gnosis was familiar with.

"oh... Espy.." He reached out and hugged the espeon who only sobbed against his chest...