Espy:Tales of a Femboy chapter 4

Story by Vulpsis on SoFurry

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#4 of Espy:Tales of a Femboy

The story of Espy continues! Espy attempts to win over Max while the Girl's Club are hanging out outside!


Espy awoke with a long and satisfied yawn before sitting up from her bed qne stretching her arms. She pulled off her blankets and found that her panties soaked again. It was from another wet dream involving Max the Houndoom again. She figured it was something common for a developing girl like her and didn't worry much about it.

She got up and tossed the panties into the dirty clothes before stumbling over to the washroom and turning on the shower. She stepped inside and closed her eyes as she let the warm water wash away all that morning grogginess. Feeling refreshed and re-energized she stepped out of the shower feeling like she could take on the world.

After making sure her lilac fur was nice and dry, Espy skipped over to her dresser. Just the day before, her dresser would've been bare and empty like a desert. Now, every single square inch of the surface was covered with all sorts of cosmetics. Plastic bottles filled wit nail polish, brushes with bristles of all sizes, and even some scented oil for the fur.

Espy leaned over the dresser with a leg kicking up in the air to get a better view of the mirror. She turned her face in all directions to see which side was her best before grabbing her cherry red lipstick. She giggled as she twisted the cap off the lipstick and smiled to apply it along every inch of her puffy lips.

After that was done she blew a kiss into the mirror before grabbing the next item. She widened her eyes and traced along her bottom lashes before putting the pencil down and practicing her winking into the mirror. After that she grabbed the bottle of lotion and squirted the body fur lotion into her hand. She applied it against her cheeks and face before smearing it down across her body. A shudder went down her spine as she rubbed the oil over her body, even down in her privates.

Once she was done playing with her body she took a moment to really look at herself in the mirror.

"Is that... is that really me?" She whispered to herself. She was worried she may have messed up with the make-up but now she can barely recognize the sexy and beautiful girl in the mirror. She giggled before posing once more for the mirror. "I'm sure to win over Max now!" With a happy wag of her tail, Espy turned to the stairs and skipped out of her room. It was time to go to school, and she was looking forward to see how many heads she was going to turn.

Espy walked up to her locker and found Gerard waiting there for her as usual. When she got closer she noticed that Gerard's orange furred face had turned bright red.

"Espy? Are you wearing make up?" He asked.

"Yeah! It's my first time today. I didn't mess up anything, did I?"

"No! You look um you look nice." He stuttered. Espy giggled.

"Thank you!"

"So, what's the occasion?"

"Well the girl's club is having a meeting at Max's house and I wanted to look nice for the occasion."

"Wait, so you're coming to my house?" Gerard asked with a blink.

"Your house?" Espy repeated with a tilt of her head.

"Yeah, Max is my brother. Well... half brother obviously." He mumbled.

"Really?! Then do you know if... if he's said anything about me?" Espy asked.

"No, we don't really talk actually. He's always with his friend Hunter or his girlfriend Umbrella."

"Oh..." Espy felt despair upon hearing that name again along with the usual pang of jealousy. The school bell rang abruptly which meant class was starting soon.

"Come on, Let's go to class."

After School Ms. Rachel drove the girls out to northern part of town while Max, with Umbrella and Hunter, lead the front with Max's own car. Espy was amazed to see the immaculate lawns decorated with colorful flowers and shuddered at how large and fancy the homes were in this part of town.

Max braked at a tall barred gate that protected a particularly large home that was practically a mansion to Espy. The gates hummed to life and opened up to allow Max and his guests come in. Inside Espy saw the pumpkin patch field that Umbrella mentioned yesterday along with a bunch of other types of gardens being managed by a decrepit Ludicolo.

Once inside the group of gals were invited to the living room by Max. Espy, Leafy, Flaaffy, Umbrella and Ms. Rachel began to chat about how the pumpkin patch field could be ideal while they sat on long comfortable sofa chairs. Hunter was surprisingly polite compared to his usual rambunctious self in school. He and Max were just talking within earshot of Espy on a different sofa.

"It's pretty huge! And the shed looks like it can hold sound equipment and even a stage!" Flaaffy exclaimed.

"We can have a band play or use a stage to give awards for best costume or cutest couple!" Added Leafy.

"Let's not get ahead of ourselves girls." Ms. Rachel advised before turning her attention to Max. "So Max, is your father really willing to open up the pumpkin patch and shed for the School?" Ms. Rachel asked while clasping her green hands together.

"Of course!" A loud voice boomed from the other room.

Everyone turned their heads to the rather plump and stout Houndoom that walked in from the other room. He wore a fancy black tuxedo and was accompanied by a Gallade that acted as a butler. "Ms. Rachel! Haven't seen you since the last conference! Come, let us talk while your little club go on out and examine the patch and shed." He offered while walking up and offering an open hand to the Gardevoir.

"Oh my, if you insist Mr. Headroom!" Ms. Rachel accepted the gesture and stood up to walk along the old pudgy Houndoom and left the students on their own.

"Babe, you go outside. I have to use the washroom." Max said before planting a smooch on Umbrella's cheek. She giggled and nodded before her and the girls and Hunter got up to head on outside.

Espy fell behind the pack. Now that Max and Umbrella were separated she had to act hard and fast. She lowered a hand and closed her legs around it and pretended to jump around as if she needed to pee.

"Ah darn, I really have to go." Espy huffed.

"Just follow Max, he'll lead you to the bathroom." Leafy suggested.

"He went upstairs." Added Umbrella.

"Thanks!" Espy chimed before turning and running.

Max had just stepped out of the washroom before he jumped in shock from Espy's presence.

"Oh! Espy, you surprised me." Max said before sighing with relief.

"Hi Max!" Espy held her arms together behind her back before she stepped closer. "You know, I've been thinking about you." Espy couldn't register a definite emotion from his face. He was blushing which was a nice sign but he didn't seem happy or anything. In fact, he seemed nervous.

"You have huh? To be honest I'm surprised you joined the Girl's Club. I see you're wearing make up." He mumbled trying to steer the subject elsewhere.

"Yeah, it's thanks to you that I know what I am now." Espy reached out and grabbed Max by the hand. "Come on, let's go somewhere private!"

The two climbed up the old creaky steps that lead to the attic of the mansion like home. Espy eyed over the various antique junk and piled up boxes holding clothes, books or old tech. Max was clearly paranoid about leading Espy up here and was checking his back along the way. Espy walked up to the only source of light that was filtering through the lingering dust that hung in the air.

Finally feeling secure Max walked up to Espy and gazed outside the window that viewed Leafy and Flaaffy pointing while Ms. Rachel spoke with Max's father.

"It's a beautiful view." Max uttered.

"This is a beautiful home." Espy added before tilting her head to eye Max. He eyed her back for a brief moment but sighed.

"Listen Espy, I know what you're trying to do. But I need you to understand that I love Umbrella. What happened earlier this week didn't mean what you thought it mean."

"Then what did it mean?" She asked.

"I don't know. I've been beating myself up about it this entire week. It was actually my first time, doing that."

"So...I was your first?" She smiled as Max nodded his head.

"I was saving it for Umbrella. When we get married. I told myself that it didn't count, that it was just head and that it didn't matter because you were a-"

"But it did matter, didn't it?" Espy interrupted.

Max paused. He wasn't quite sure how to word anything right now.

"See, it was the spur of the moment. It was just a joke at first, what I said. But Hunter was actually doing it and seemed interested. I didn't want to seem like a pussy to him."

"So you did what you did because of Hunter?" Espy sounded hurt.

"No... I mean. Kinda? I'm not sure why I went through with it. I mean at the time I kinda did want to do it and like I said I thought to myself it wouldn't count. But obviously it did, I've been hurting ever since so now I want to make it clear right now that I'm not interested. If Umbrella finds out I-"

The two were then abruptly interrupted by footsteps running up the creaky stairs.

"Crap, hide!" Max whispered. Him and Espy ran behind a tall stack of boxes. Max piled a light box on the other to hide himself and Espy before the two peeked over the side. Umbrella strolled in to Espy's surprise. She thought that Umbrella was outside with the others.

"Max? Espy?" Umbrella called out. The two remained ducking behind the boxes. Max gave Espy a stern gaze and raised a finger against his lips. Espy nodded, she understood. Remain quiet.

Every step Umbrella took forward caused the old wooden floorboards to creak with a drawn out pitch. She drew closer, her looming presence making Espy's and Max's heart rate to spike off the charts. Espy could sense her approaching the boxes and almost began to panic, but then she felt Max's hand on her shoulder, his gaze as stalwart as ever.

Why did she have to fall in love with somebody already taken?

The two remained silent and felt a wave of relief when Umbrella began to walk away. Max began to relax and Espy smiled up at him until Umbrella broke the silence.

"Okay Hunter, the coast is clear." Max's eyes shot open upon hearing that.

"You sure we should be doing this up here?" Max's best friend asked.

"We've done worse. Plus nobody will come up looking for us. I told the girls that I needed to make an important phone call and to not bug me."

The two couldn't see but they could hear everything going on. Two pairs of feet walked across the wooden floorboards. Max or Espy couldn't make it out but they could hear the distinct noise of fabric rustling.

"Damn Umbrella, in Max's attic? You're getting riskier."

"You're one to talk. You're the one that sneaked into my room last night." Espy watched while Max's expression and demeanor gradually went from bad to worse. A dark finger was jammed into his maw and was nearly gnawed off while tears of betrayal began to form in the corners of his eyes. Espy wished she could help. She wanted to reach out and help him in his time of need but at the same time she didn't want to be caught.

The rustling of clothes quickly evolved into soft muffled moans while the slick gushy sounds of exchanging tongues filled their ears. Espy heard a push and Umbrella grunting when she was slammed against the wall. She could see their shadows stretching along the dimly lit walls and could make out what was happening next.

Hunter had forced Umbrella against the wall and slipped his gray hands underneath her skirt. Umbrella's legs stretched open while she looked back, her tail raised high and her ears splayed low. Her panties were then lowered to just below her ankles before Hunter lowered his pants some more. The sound was an impending realization for Max. Espy watched while he closed his eyes shut and held both his hands against the sides of his head below his horns before it started.

Espy watched the shadows. Umbrella was standing up forced against the wall while Hunter held her by her luscious hips. Soon the shadows began to rock against each other, the sounds of their crotches thapping against each other created further anguish for Max who merely attempted to rub his hands closer in a futile attempt to block out all sound.

"Jeez Umbrella you're soaking wet, does the idea of Max catching us make you excited?! "

"Sh-shut up! Fuck me harder! "

The rocking motions began to pick up. The thapping noise was quickly followed with a subtle sloshing effect with each thrust Hunter made. Umbrella's back began to curve while Hunter's hands traveled up beneath her shirt to grasp and squeeze at those breast that Espy envied so much. It wasn't long before Umbrella's tiny squeaks grew into full blown moans of pleasure.

Their shadows moved, Hunter had grabbed Umbrella by her hips and pushed against the single window that overlooked the front of the tall Gothic house. At first Umbrella tried to step aside but Hunter's gray furred hands forced her back.

"Wh-what are you doing?!" Umbrella hissed below her breath. Hunter only grinned down at her before pushing his hand against her curvy back to press her against the window.

"I found out what turned you on. It makes sense that you only wanted to fool around when Max was around..." His hands slipped beneath her silky white button shirt once more and grasped at her breast while his cock pounded against her round ass.

"I-I don't know what you-you're...Ahhh...:"

Umbrella couldn't finish her statement. Her cries began to rise with rapid succession as Max's thrusts began to speed up. He had to reach over and cover her mouth with a hand while the other wrapped around her waist. He then humped as fast as he possibly can, his hips moved like a blur while Umbrella's muffled cries matched with his humps.

Soon her fluids trailed down her bare black furred leg and moistened the dusty wooden floor where she stood. Hunter was growling with delight as he moaned and sighed, the Mightyena clearly enjoying an orgasm of his own and pushing in to rest against Umbrella.

"I knew it... the thought of getting caught or being seen is what turned you on..." Hunter finally stated with a relieved sigh before pulling back.

"You're an asshole..." She panted before lifting back up her panties.

"Heh, was I right or wrong?" He asked with a smirk while peeling off his rubber. Umbrella pounded him with a pout before softening up and standing on her tippy toes to plant a smooch on his snout. "Come on, let's go back downstairs before they find us.

Max shook his head refusing to accept what had just occurred in his own home. Espy wondered if he was trying to deny the reality of the situation. All those words about love and promises were nothing but delusional daydreams for him now. Espy reached out a hand and mimicked Max's gesture earlier by grasping his shoulder and squeezing it reassuringly. Max opened his eyes finally and revealed the heartbroken tears that accumulated inside. The salty drops dripped down onto the dry wooden floor while his lips were twisted in agonizing silence. Espy almost felt like crying from seeing his miserable expression but she merely gazed into Max with what he hoped looked like reassuring eyes and nodded.

Max nodded as well before he finally stood up.

"I deserved that..." He finally said after all that.

"No, you didn't."

"Yes... I did."

"No you didn't!" Espy repeated. "You cheated on her once, yeah. But at least you were trying to make amends! It sounds like she and Hunter were doing this for a long time already!"

"I... I can't believe it." Max fell onto his knees and buried his snout into his hands. "He's my best friend damn it, how could she?"

"I'm sorry..." Espy said trying to console him. She knelt down and rubbed a hand against his back while she held him close. "I guess it wasn't meant to be."

When Gerard came home he found Espy and Max in the kitchen. He lowered his backpack and undid his tie before waving at his brother. Max waved back but didn't seem to express any other emotion. Espy on the other hand ran up and hugged Gerard as a form of greeting.

"Hey, Girls Club?" Gerard asked Espy.

"Yeah, but they left already."

"Where's Hunter?" Gerard asked while facing Max.

"He left." Max muttered.

"That's weird. He usually sticks around longer."

"Something happened." Was all Max said.

"Well, it was nice coming over Max. But I need to head home now." Espy said to change the subject.

"Come on, I'll give you a lift." Max offered. Gerard hugged Espy before she and Max headed outside.

During the car ride the two said nothing for a long time. Espy was giving directions to her home while Max kept his attention out on the empty road the entire time.

"I see my brother has taken an interest in you." Max said, breaking the silence.

"Yeah, he asked me out like a hundred times since I find out that I was a girl."

Max skidded to a stop.

He turned and gave Espy a weird look.

"Since you found out you were a girl?" He asked.

"Yeah! I didn't know until that day you and-"

"Wait, stop. You think you're a girl?"

"Well yeah! You said it yourself remember?" Espy didn't understand where this was going. Max shook his head in disbelief before moving the car again.

"I thought you were pretending to be a girl. Like one of those femboys."

"Femboys?" Espy asked.

"Yeah, a boy that looks like a girl but isn't." Espy still didn't understand. She did but she didn't at the same time. Her entire world was crumbling. She... no he felt so right dressing up and applying make up like an actual girl. But now that facade was crumbling, fast.

"So y-you're saying that?"

"Espy. You're a boy."