First Night

Story by UmiTheUmbreon on SoFurry

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#19 of Midnight

A female teen with only a few months left of high school falls into an intimate relationship with an umbreon on the school's grounds. She has to juggle this and high school itself, all while finding herself as a person. Playing it safe is key.

This story was the first I've ever written. I've edited it a lot since the initial release but kept its original structure.

~

Existing; complete stories:

'A Night She Couldn't Resist.'

(Male midnight lycanroc x fem trainer.)

'Cassidy's Journey.'

(Male braixen x fem trainer.)

'All They Knew.'

(Male alolan ninetales x fem trainer.)

'Hidden Lifestyle.'

^ Excluding 'Midnight' and 'Hidden Lifestyle,' all three works take place in the same universe.

~

All NSFW scenes:

Chapter 6

Chapter 11

Chapter 19


Today was it, the last Friday Julie would ever be at this school again. The prior week was one of realization, that she was going to move on with her life and that she had to find out what to do with it. Julie wasn't much of a tough trainer type. She wasn't a fighter in that manner, so she had decisions to make.

Julie would think about that later, however. The graduation ceremony started at noon, and she had to get her yellow cap and gown on before she left home. It didn't help that Alyssa was texting her every ten minutes, even though Julie needed to be there in half an hour. She sighed and picked up her phone to see the message this time: 'Saved a seat for you in row 3. I know you'll take a decade trying to look good.' Julie didn't respond, but she would hurry. She was already rushing in fact. She needed her backpack today as she had to return her textbooks, so she slung it over her shoulder and headed out the door

Julie got there in an impressive twenty minutes since she walked at a brisk pace, and her legs and shoulders were tired as a result. Once she walked through the school's entrance and made it to where the ceremony was down the packed hall, Julie sat in the chair Alyssa saved her in the auditorium and set her backpack down. It took a while to get to her seat, considering the room was full.

"Ah, there she is." Alyssa spoke over the buzzing and leaned back in her seat, looking at Julie.

"I slept in a little, but I made it on time, so shish!" She grinned and stretched her legs. She was still recovering from the walk. "My mom is going to show up soon. She has to leave her job for a bit to attend."

"That's sweet; mine should be coming too."

--

The event lasted for a tedious two hours, and the auditorium was empty soon after it ended. Most of the students that attended were hanging out in the cafeteria.

"I feel liberated and a bit lost already." Julie took off her cap as she and Alyssa exited the auditorium.

"Give it some time. You'll figure everything-"

"Julie!"

Alyssa was abruptly cut off by a voice that came from down the hall. They turned around to see Mr. Willam jogging toward them with Midnight trotting at his side.

Julie's face lit up at the sight of him.

"I didn't forget about our deal. You've waited and made it to graduation day with astounding grades. Congratulations!" Mr. Willam smiled and took a step back. "He's all yours. Take care of him."

Julie looked at Midnight as he took a few steps toward her, and she could've teared up standing there. She leaned down and picked him up, holding him close to her chest. "Thank you..." Julie's tone was vulnerable.

"Goodbye now, Julie. I wish you well, and you too, Alyssa." With that, he walked back to his office.

Alyssa turned to Julie and eyed her and Midnight. "What a sight... He is pretty cute." She raised her right hand and gently patted Midnight's head. "You can go home with your boyfriend if you want. I'm gonna stay behind and check out what's going on in the cafeteria. I'll text you later tonight, though. I can return your books for you too if you'd like?"

"Sure thing, Aly. Thank you, and see you!" Julie waved her off after handing Alyssa her heavy backpack and walked out the front doors of Ecruteak High while holding Midnight. She kissed him on top of his head. "I missed you a ton. We're together for good now..."

"Bre." He looked up at Julie as she spoke and rested his cheek against her chest. He felt great comfort within her embrace.

Midnight hadn't been off of school grounds unless it was to the principal's home or in the surrounding area, so being walked by Julie through scenic routes filled with nature felt like pure freedom, even more so once they entered Goldenrod. His eyes shot around at the buildings surrounding him, especially the ones towering above. Midnight's often turned his head to eye other pokémon and trainers in the bustling environment.

"Someone's excited." Julie walked through the city toward her house while Midnight took everything in.

"We're here..." Julie grinned and unlocked her front door with the key. Her mother was still at work and would be for hours. "We'll stay in my room until tomorrow." Julie set Midnight on the floor and closed the front door. "C'mon, I'll get you something to eat in a bit." She went upstairs, and Midnight was right behind her.

It felt different being in such a new setting and with his favorite person at that.

"Not much, but it's where you'll be sleeping. You can take the bed with me if you'd like."

He would without question. Midnight hadn't been cuddled while living with the principal, and it had been impossible for Julie to at school.

Julie went back downstairs and brought him some poké chow in a bowl, which she always fed to Lilly. She wondered how or if they'd get along. Julie wouldn't have to worry about it for a while since she and Midnight would be gone soon.

--

Nine hours passed. Midnight and Julie took a long nap together. It wasn't intentional, but it happened once they lay on her bed and got under the covers. Julie was still asleep under Midnight. He was sprawled across her chest and stomach, gazing at her face while she slept.

He was interrupted once her eyes slowly opened to see two big orbs staring into hers. "Mmh... Midnight," Julie mumbled and rubbed her eyes. "What time is it?" She reached her right hand under her pillow and blindly searched for her phone. Once she had it, Julie checked. "Almost midnight. I forgot you're a night owl." She grinned up at him and slowly traced her fingers across his body's sides.

Midnight closed his eyes slightly while receiving the small massage and leaned his head down to give her neck a few soft licks. It was a thank you gesture, but he heard Julie gasp lowly as a result. He perked his ears and lifted his head.

"... It felt nice," she reassured, so he went back to giving her neck licks with his warm tongue. Julie tilted her head up to grant him more access. Her eyes were closed completely, and she softly sighed through her mouth, pleasure rushing her in subtle waves. Julie was aroused, and she now wanted Midnight more than ever. "M-Midnight..." Julie interrupted once she got his attention.

His eyes were filled with passion as he stared down at his new trainer.

"I... can't wait this out." Alyssa was right about that. She sat up slightly and felt her cheeks redden. "Do you mind relieving me?"

Midnight gave Julie a quick nod in response and sat up on the bed. He missed her in that regard as well.

"Hold on." Julie pushed the covers away and quietly got up, going to lock her bedroom door. She couldn't have another incident involving her being walked in on. It was only Lilly last time, but it could be worse this time. Her mother was home, probably asleep, but Julie couldn't risk something like that. She went back to her bed once done and sat on her knees in the center by Midnight. His rings dimly glowed, fading against the moonlight slipping in through Julie's bedroom window. Julie smirked and reached her hand down to his lower stomach. She didn't have much to do either; Midnight had gotten fairly aroused from eyeing Julie's lower body. She had on white panties, a t-shirt of the same color, and short socks, so when Julie reached what she thought would be his sheathe, it was his halfway erect member.

She kept her eyes on him while lightly tracing her fingers up and down its underside. That was when a thought came to her. He'd been inside two of her holes already, but he hadn't tried her rear. The best she could do in preparation was wet his shaft before intercourse to provide an easier slip-in. Julie lay on her stomach in front of Midnight, and he promptly parted his hind legs for whatever it was she was going to do. "Just a tease..." Julie said before leaning forward and slowly taking half of his length into her mouth. She placed her hand on his right hind leg and slowly bobbed her head on his growing member, fondling his testes a bit with her left hand.

Midnight couldn't help but lightly hump against her movement, his ears slightly twitching while savoring the warm sensation Julie's mouth gave him.

She upped her pace, licking around his shaft while taking in more of his length, feeling his cock twitch against her tongue while spurting pre. It would be hard to keep this a tease. Perhaps she wouldn't.

Midnight further spread his legs, swaying his tail and breathing quicker. He could orgasm quicker than expected if Julie kept going and didn't know how to notify her. It felt good enough that a part of him didn't want to. He felt her take in more of his shaft, his tip close to entering her throat while her soft tongue caressed his glans. "M... Mmb."

Julie shut her eyes, resisting the urge to gag while audibly sucking Midnight off. She felt him shudder, his hips bucking against her mouth. He was nearing climax, and Julie had gone too far to stop. She leaned in, taking the upper half of his cock into her throat while quietly gagging on it. "Ahk..." Her left hand held the bedsheets.

Midnight huffed, having to breathe through his mouth to cope with the pleasure. He'd cum within moments, and if Julie didn't stop, he wouldn't make her. He shut his eyes, shifting his front paws while her throat hugged his member.

She bobbed her head quicker, parting her lips and taking in the rest of his length, so most of it was encompassed by her throat. Julie gagged a few times, tensing and squeezing the sheets.

"B-Brem..." He was so close. His body was hot. Midnight twitched his ear to her gagging and the wet sounds her throat massaging his hard cock produced. He stuck out his tongue, shoving his hips forward while his legs quivered. Midnight opened his eyes and muttered his name, an orgasm that blurred his vision rushing over him.

Julie's cheeks reddened. She swallowed his thick cum, rubbing his hip while he released. Julie pulled off a moment later and wiped her mouth, looking up at him while catching her breath. "Some tease, hm?"

Midnight swallowed, breathing quickly. She'd surprised him all right, and he enjoyed it thoroughly.

"Let me just..." She grabbed both sides of her panties and slid them down and off her legs, her breathing slowed. "I think I'm ready." Julie was nervous about having him back there as it would be her first time trying anal. Julie got on her hands and knees in the middle of the bed. She would use the bit of flexibility she had to lower her upper body once Midnight mounted her. "Come on..." She grinned back at him, and once given the opportunity, Midnight stood on his hind legs for a second and precisely gripped her inner thighs with his front paws. Julie quietly sighed feeling his furry chest and warm paws against her skin. "Put it in my ass this time, hun, but... Be gentle again," she spoke in a quiet tone to be on the safe side.

Midnight had to prod around her rear cheeks, which were of perfect size to him before his erect member's tip poked her anus.

The confirmation came from her sudden gasp and the way she momentarily tensed, and now that he was ready, Julie lowered her upper body and leaned on her elbows. She slowly raised her rear for him. "G-Go ahead, I'm ready." Julie calmed herself while bracing for entry.

Midnight ensured he had a good grip on her inner thighs before slowly pushing his hips forward. Julie's saliva made it easier for him to enter her as he was already halfway inside. "U-m..." It felt much tighter and warmer than her vagina. He couldn't help but wince from the amazing sensation stemming from it.

"Ahn... K-Keep going." Julie gripped the bedsheet with her right hand. It hurt having him inside of her rear, but in a good way. She felt him slowly push the rest of his stiffened shaft into her constricting walls, and Julie couldn't help but let out a breathy moan at his length fully inside of her. She took a few moments to adjust to his size and was ready for him to start moving. "You can start thrusting now, Midnight." Julie would have to work on staying quiet from this point on.

Midnight slowly moved his hips. "Nmbre..." He shut his right eye from how tight her sphincter and walls hugged his cock each time he thrust. Her light exhales provided encouragement, so after a few more, he humped his hips against her rear faster, flattening his ears as the pleasure received from her pulsing walls became more intense.

"Ohh... Y-Yes, Midnight, such a g-good bree..." Julie's words faded into a mumble as she felt Midnight's shaft rub her walls. It was an immense mixture of pleasure and just a touch of pain.

"Mm..." Midnight thrust swiftly, audibly tapping her rear cheeks each time, which caused them and her thighs to lightly jiggle upon contact. He pushed Julie's body forward from the newly created force, spurting pre-cum into her walls. His movement was faster and wet. He couldn't get enough of her, and neither could his twitching erection. The bed lightly creaked under them, and the sounds of their session echoed throughout the room, but it wasn't loud enough to alarm Julie.

She squeezed the bedsheet with her hands, and her eyes rolled back a bit from the constant waves of ecstasy overtaking her body as Midnight pounded her roughly. "Nhn, Midnight, oh..." It was nearly impossible for her to keep quiet, and a few gasps and unsafe moans escaped her open mouth as a result.

Midnight huffed through his nose. Before he reached climax, he wanted to please his trainer more. Promptly, he leaned forward and placed his paws on the mid-section of her back. Midnight could take more control, thrusting into her tight ass rougher. He released more pre into her walls, which brought him a consistent wet and hot sensation, but the way her heated walls clenched him was taking him over the edge. "B-Breon..." he groaned with gritted teeth and short breaths, the bed creaking louder under his movement.

During Midnight's next few thrusts, his cock slipped out of her ass, poking and rubbing her thighs as he at first continued his motions. Midnight slowed when he felt cool air hit his shaft and the pleasure come to a halt. He stiffened his member and thrust upward, prodding around her cheeks before his next found her anus. Midnight pushed inside of her ass again, bringing a gasp out Julie and consuming him with the pleasure he missed. He felt at home again, closing his eyes while roughly humping her.

Julie could only hope he finished quickly. She wouldn't stop him. His cock felt too good. "Mhn... H-Harder... You're making me feel s-so good!" Julie moaned in a high-pitched and muffled tone since she'd, fortunately, buried her face into her pillow. She slightly pushed her hips back against his dominating thrusts and reached her left hand to grip her rear cheek and spread it for Midnight. It pushed his shaft deeper into her ass and brought them both enhanced pleasure.

He rested his head on her back, his eyes shut tightly, and his tongue nearly hanging out of his mouth while he pounded Julie. Midnight's hips smacked against her rear harder while he rammed his cock inside her backdoor. He grounded his hind paws into the bed, and they slightly tensed as he approached his climax.

"Ghn... He's close..." Julie stuck her rear out against his wild humping, her moans and shaky exhalations frequent. Her legs trembled, her arms tightly embracing the pillow as a way to cope with the pleasure.

His tail stiffened as he humped against her rear. Midnight couldn't hold back anymore. "Umb-breon!" A few more thrusts into Julie's tight hole and a powerful orgasm inundated him. He pressed his paws into Julie's back and felt himself zone out while shooting thick semen inside and marking her rear walls. Midnight made sure not to push his length inside too deep as not to harm her with his knot, so he kept thrusting hard while he came, increasing his pleasure significantly since her rear walls tightened and constricted his erection. Some of his release seeped out of her twitching hole and stained the bed beneath. As it faded, he slowed. They kept still for several moments to catch their breath before Midnight pulled out by unmounting Julie.

She lay on her side and attempted to catch her breath, which she managed to do in minutes. Julie felt his cum slowly run down her thigh. She'd have to shower and wash the bedding tomorrow. "You're amazing..." Julie sat up slightly and gently pulled Midnight to her chest. She draped her right arm over him and held him close. Whether or not he was a moonlight pokémon, he'd sleep the night away for certain now.

Midnight curled up and rested his tail over his hind legs, his chin on his front paws, savoring her hold. He closed his eyes, exhausted. It didn't get better than this.