Why was she doing this? It had to be wrong, or something along those lines. And yet, here she was again. Jeanette had to tell herself again and again that there wasn't anything wrong. Her and Simon weren't a thing yet…
Jeanette was in the Seville's backyard. It wasn't the first time, and it was likely that it wouldn't be the last either. She crouched down, taking up a little rock as she looked to the window that lead to the boys' room. After taking aim, she threw it up, a little smile coming to her face when she heard it clink against the window.
A few second passed, and the window opened up. Theodore peeked out, glancing around before he looked down at her. "What the... Jeanette? You're back already?"
"S-Sorry Theo, but can I come up? It's… important."
"Uhhh… Sure. Room's clear. Lemme just fix the bed."
"This is the fifth time this week, Jeanette… is everything okay?" Theodore asked as he locked the bedroom door, turning back to look at the Chipette. "If you want I can ask Simon to-"
"N-No! Definitely not!" Jeanette blurted out, shaking her head as she closed the window behind herself. "Let's just h-hurry and get it over with. I… I've been thinking a lot lately."
Theodore rolled his eyes as he made his way back to his bed, plopping down on the blanket and patting the spot next to him. "Thinking about what? When you're gonna tell him how you feel?" he asked as she joined him on the bed.
"I don't know… can we skip that part? I'm all antsy and I just need this for now, okay?" Jeanette huffs, looking ahead as she grabbed at the hem of her skirt. "I-I promise, I think this is the last time anyway. Just… please. Let's do it."
"Last time…?" Theodore echoed. "Alriiiight. Get comfy!" Theodore said as he got off of the bed and lifted up his sweater, exposing himself to her as he tugged his underwear down.
Jeanette bit her lip as she watched him do so. She hadn't planned on falling for Theodore… not in a romantic way, of course, but he could turn her on for some reason. She squirmed as his underwear fell down to his ankles, soon being kicked aside.
He wasn't even that big… at least when he was soft. Jeanette knew that she liked the sight of him either way. Theodore held his sweater up to his chest, humming as his pudgy form was out on full display, shaking his hips a little so his shaft would sway.
"Your turn~" he cooed.
"R-Right." Jeanette cleared her throat, laying out on the bed as she lifted up her skirt. Why did her hands still shake when she did this…? She's done it so many times and yet she still felt nervous. She kept herself well trimmed and everything. She should be okay with this. "Can you use your hand more this time?"
"No problem!" Theodore tugged his sweater off all the way, setting it on the bed as he sits down at Jeanette's side, reaching in between her legs. First, he was rubbing around her lower belly area, his hand hovering just above her crotch as it moved through her fur.
Oh god… Jeanette closed her eyes, letting out a soft sigh of relief as soon as she was being touched. Something about the contact; the specific way Theodore did it. Jeanette, fighting through her nerves, let out a little moan as she tightened her hold on her skirt. "A-Aahhh…"
"Let it out, it's okay." Theodore encouraged, smiling down at her as he continued to rub the spot. He still thought her requests were weird, but she insisted there wasn't anything wrong with it. And he was helping out his friend. He'd never feel bad for that. "Hearing you make that noise gets me going, you know."
"I-I know." Jeanette kept her eyes closed. She could feel the blush settling on her cheeks as she lifted her hips a little. Another moan escaped her, and Theodore's hand moved lower. Everything was just so soft… She peeked up at him, sitting up a little as she parted her legs more. His fingers were tracing around her slit now, pushing down with just enough pleasure to make her body buzz with bliss. "Oh g-gosh, Theodooore…"
For someone who was mostly inexperienced, Theodore caught on pretty fast. It only took them one session for him to know just what buttons to press and when, and yet she was still trying to learn all of his spots. All she knew was to mess with his chest here and there.
Theodore snapped her out of her thoughts when his fingers curled upwards, two of them sinking right inside of her pussy and rubbing at her inner folds. And he was smiling the whole time. Jeanette squeezed her legs around his hand for a moment, moaning out loud as she humped herself against his fingers, one hand grabbing his shoulder for support.
As much as she moved around, he didn't lose focus, keeping his fingers pumping back and forth in that steady rhythm of his. He pressed down on her tunnel here and there, the action causing her to twitch in place as she gripped his shoulder even tighter, moaning his name quietly as she let herself leak on his fingers.
He always did so much for her… Even when she didn't return the favor sometimes. Jeanette's brow furrowed in thought, powering through the pleasure long enough to grab Theodore's hand and push it away, panting heavily as she looked at him. Sure enough, he looked pretty confused that she made him stop. "What? D-Did I do something wrong?" he asked. "If i-it's cuz I started curling my fingers, I'm sorry! I just thought it'd make it better!"
"W-What? No, that's not it." Jeanette grit her teeth then, sitting up in bed as she took a deep breath. "Theo, I… want you to lay on your back. I'm gonna do something for you too this time."
"Huh? Well… okay." Theodore shrugged his shoulders, but laid down on his back as requested. "What're you planning?"
"Just a little something I thought you'd like…" Jeanette mumbled under her breath. Keeping her skirt up high, she climbed on top of Theodore, facing his crotch as she lay on him. He grunted, but didn't object.
Jeanette found herself staring down his length. He was already starting to harden up! Theodore's dick pulsed as it rose, growing right in front of her while she stared. Just watching it go… she felt herself grow a little wet.
"W-Whoa… Whatcha want me to do?" He asks her, tilting his head as he stared down her slit. It only took a few sniffs before Theodore went to licking at her pussy, his hands grasping her waist firmly, holding her in place as he savored her taste. She hadn't asked him to do this before.
"Aah! Just keep doing that!" Jeanette gasped as she felt the surge of pleasure go through her body. Of course he'd be good with his tongue… She bit her lip, panting softly against his crotch as she took hold of his shaft. A guy like him shouldn't be big… she almost needed both hands to hold the whole thing! Fighting through the pleasure, she started stroking him off as usual, keeping close to the base as he liked it.
Hearing him moan in between his licks was like music. While she kept her quick and steady pace with him, he was all too eager to bury his tongue into her folds, pushing it in as deep as he could manage to.
"J-Jeanette… lick it, please…" Theodore panted, his breath warm against her soaked crotch. Was he drooling on her? Or was she just that aroused? Either way, she obliged his wish, even if she had to steel her nerves a bit first. Theodore moaned louder than usual as soon as her mouth closed around half of his cock, a shot of pre landing on her tongue as reward. His taste was sweeter than expected…
"Mmnf, hrm." Jeanette grumbled, grabbing his thighs softly for support as she started to bob her head along his shaft. Theodore's hold on her tightened, and Jeanette squeaked softly as his tongue ran up against her walls. She ended up squeezing her legs against his face, whining around his cock as she lowered her hips closer to him.
Eleanor was going to be really, REALLY lucky if he went after her.
Theodore arched up against her, giving a thrust up that caused the head of his cock to jab the back of her throat. Jeanette gagged for a moment, eyes watering a little as she closed them tight, pulling back to cough. "T-Theodore! Easy, you almost got in my throat!"
"I-I'm sorry Jeanette…"
Jeanette sighed as she tucked some of her hair behind her ear. "It's okay, just… warn me next time." She sighed, looking down at his shaft once more. If she knew he'd reach that far, she wouldn't have suggested this! She took in a deep breath and went down again, trying her best to relax her throat.
This time, when Theodore's tip neared that spot, she slowed down, only letting it touch for a quick moment before she pulled back, opting instead to suckle at the head while her hand held his base.
"Ngh! O-Oh m-maaan…" Theo was doing his best to not buck his hips anymore. But, unless he just couldn't remember, she's never used her mouth like this. Maybe she did on his chest, but never down there. It felt amazing! If he could reach, he'd be doing that himself. "I-It's too good, Jeanette, I can feel it c-comiiing…"
As he said that, Jeanette was going to lift herself off of him, but soon found that she couldn't. Theodore's arms were wrapped firmly around her hips, and he mushed his face into her crotch once more. "T-Theodore?"
"Mhhhn!" Theodore shoved his tongue inside of her again, tensing up as his shaft gave a strong throb. Then, the peak came. Theo moaned right into Jeanette's slit as warmth spread all throughout his body, his cum spurting out several times, most of it landing right on Jeanette's face while the rest either got in her hair or made it to his belly.
All the while, Jeanette had to jack him off to keep him moaning throughout his finish. She opened her mouth to catch some of his last squirts, her blush getting stronger when his spunk landed on her tongue. Sweet, salty, and just a little bitter, whatever landed on her tongue was soon swallowed down.
Theodore was left panting heavily when he eventually released Jeanette from his death grip. "Gosh, your mouth was amaziiiing…" He praised, lightly petting Jeanette's butt. "Want me to keep going?" He offered.
"N-No, let's just get to the main part. You're still hard enough for one more go." she answered, climbing off of Theodore so she could lay at his side.
As soon as he caught his breath, Theodore got off the bed, his cock still bobbing with life as he moved in between Jeanette's parted legs, carefully lifting them up until her thighs had completely squished his cock in between them. "A-Ah… You sure you don't want it inside you…?" He asked, his cheeks noticeably dark as he looked to her face. And yet, Jeanette shook her head.
"Just get going. And keep hitting that spot I told you about last time, okay?" She instructed. Jeanette gasped when Theodore did as asked, hugging her legs up against his chest as he began thrusting as fast as he could manage to. She watched as his cock disappeared between her thighs, just to peek back out every time he pushed forward. But what really had her going is how he was constantly grinding on her clit. Having that little bud assaulted nearly made her scream, but she knew better. She clamped her hand over her mouth to stay quiet, whining into her palm as she leaned up into his thrusts.
"H-Hey, lemme hear you~" Theodore cooed, giving her legs a squeeze as he continued rutting, his pre dribbling out to land on her crotch. "Your thighs always feel so gooood…" He praised her, resting his head against her leg.
Jeanette bit her hand softly so she'd stay quiet, and yet a few moans still managed to slip free. She couldn't help it! At this point, she couldn't tell if it was Theo's pre or her own juices making more of the mess, but she didn't care either way. Her orgasm was getting closer and closer, and she wasn't going to miss it for anything. "Theo… Theodooore…!"
She wanted it. Badly. As much as she loved the way he felt up against her clit, her body was screaming for more. To be filled, to be pounded into a quivering mess like those videos she saw. Her mind fought against her body's desires as she wiggled her hips. She wanted to save the main event for Simon. She wanted Theodore to ream her until she couldn't speak.
"A-Ah… Jeanette, you're so wet~" Theodore commented, looking her in the eyes as he released her legs for now, leaning down until he was holding her shoulders, sniffing her face some as he continued grinding on her cunt. Then he started licking her face, specifically the parts where his cum had landed earlier, cleaning the spots without hesitation. He'd tasted himself before, and liked it. "Mmm… Not as good as you taste~" He says, bumping his nose up against hers.
Did she dare…? What would it mean? Jeanette's mind was racing, thinking of different ways things could play out. She groaned, gritting her teeth for a moment before she grabbed Theodore's cheeks, making him look her in the eyes once again. No turning back.
"Theo… put it in me. Don't ask why, just be quick so I can cum!" The words escaped her before she could doubt herself any more. She had to have it. She just… had to.
That made Theodore look at her in confusion, but he went ahead and did it anyway, his length lining up with her entrance before he took the plunge, burrowing his way in until his tip met a barrier. He tried to go through it, but Jeanette grabbed him by the hair, tugging it as she hissed in pain.
"N-No! Don't go pass… Just keep going like thaaat…" She whined, letting herself relax in place as she rubbed through his hair.
Jeanette moaned at the top of her voice as Theodore kept to that shallow depth. She wished she could have him in her completely… but having some of him inside of her folds was good enough. She squirmed on the bed a little, letting out little whined and moans as she gripped the blankets beneath her. There it was, her climax. Closer… closer… closer… Her breathing was heavy, shaky and short as she tried to get there for dear life. She moved her hand down to her crotch, pinching and rubbing on her clit relentlessly, her moans almost turning into screams as she felt her walls clench down around Theodore, her orgasm coming with a whimper as she finally peaked, her juices squirting right on Theodore's crotch and leaving a mess while she tried in vain to push herself closer to him, keeping his tip just up against her barrier. "Ohhh g-goooood!"
Her vision faded some. Everything felt fuzzy, and she couldn't even keep her hold on Theodore. Jeanette fell flat on her back, panting heavily as she let the afterglow wash over her. What a rush…
She snapped out of it as Theodore pulled out, laying down at her side as he caught his breath as well. "G-Gosh, Jean… what made you change your mind?" He asked softly. "Did I do good?"
"Oh Theodore… you did amazingly well." She answered, looking up to the ceiling as Theodore hugged her from the side. "I think I'm going to ask Simon soon, though… S-So we're gonna have to stop our little meetings." She said, looking over to his face. However, he didn't look upset at all.
If anything, he looked happy. All smiles as he bumped his nose on hers, pulling her closer to him. He held on to her for a good while, not saying anything for minutes on end. When he finally released her, he cleared his throat and looked off to the side.
"Well… Good luck! Simon's crazy for you, so you and him can do this soon! A-And he could go past that spot and make you feel a whole lot better." He said with the same smile on his face. Then, his expression changed to one that looked like worry. "But, uh, do you think me and Eleanor have a chance…?"
Jeanette couldn't help but smile at that. "Believe me, Theodore, you may as well get with her today. She's all about you. I'll put in a good word, and don't worry, this'll just be our little secret like always." She said, turning her attention back to the ceiling.
'I won't forget it though…'