Simon checked his phone for what felt like the millionth time that afternoon. 'Still no text.' He thought uneasily. He had turned his phone off while judging the science fair, but he had yet to receive a message from Jeanette. That wasn't in and of unusual. Both of them tended to eschew texting in favor of phone calls when apart from each other and face to face conversation when at home. In addition, neither of them felt the need to constantly affirm their relationship with meaningless interaction.
Still, after the bombshell, he had dropped on her bed this morning Simon had expected something. He had feared an angry message calling him a dirty perverted pig at the worst, though he was confident that she was interested in it, he had expected some sort of message nonetheless. The absence of knowledge made him nervous. 'Has she even opened it? What if she hates it? Is she still considering it?' These thoughts and more danced in his head.
Sighing, Simon held his head in his hands. 'It's Jeanette.' He assured himself. 'She would understand being interested in… it. Even if she doesn't actually share the interest. But she had so much on it?' Simon looked up nervously. 'That might be the problem though, that I went on her computer without her permission. Worse, I investigated a part of her she wanted nothing more than to keep secret from others. Just about the worst thing a boyfriend can do.' Frowning in disappointment at himself Simon picked up his phone and went to message Jeanette just as Alvin entered the room.
"Hey Simon, do you still need to borrow my car?" Alvin asked seeing Simon on the couch.
"Your car? Yeah, I could still use it. The bus stop is a half mile away from the museum where I'm taking Jeanette, but aren't you taking Brittany to the movies?" Simon inquired to his brother.
"I was yeah. Still might be but we'll walk if that happens. I get the feeling though there's been a change of plans and I won't need my car." Alvin said with a smirk on his face. "The catch is, I want the treehouse tonight."
Simon's eyes narrowed in suspicion. "What do you mean you want the treehouse?"
"Come on Si, do I really need to spell it out for you?" Alvin said with a slight mocking edge. "All six of us are young, going out on dates late at night, Dave and Miss Miller are both out of town…"
Simon's face turned red at Alvin's words, all the worse because he was right. "Okay, okay you made your point. Why do you think I'd want the treehouse though?"
"Because the two of you seem to end all your dates up there maybe?" Alvin asked raising his eyebrow at his brother. "I figure its more of a Jeanette thing, but you should still be able to steer her towards your bedroom I bet. And I'm sure Theodore and Eleanor will go to the girl's house because its closer and they have all the picnic stuff. So, none of us will be stepping on anyone's toes." Alvin explained.
Simon was surprised that he couldn't argue against Alvin's logic. "Why Alvin, did you actually plan this night out? I'm impressed." He mocked.
"To be perfectly frank with you Si, something happened today that I want to talk to Brittany about and I get the feeling the treehouse will give us the most privacy," Alvin said seriously, not meeting his brother's challenge. "I learned something interesting about her but I don't know… but I really shouldn't be talking about it before I talk to her. Point is, you can have my car and I get the treehouse. Deal?" Alvin asked holding up his keys.
"Deal" Simon replied catching them as Alvin tossed them to him. "Alvin, I just want you to know if you hurt Brittany then…."
"If I hurt Brittany Si, none of you will hate me more than I would hate myself. So take what you were about to say and shove it." Alvin cut him off in anger before storming towards the back door.
'Well, that was interesting.' Simon thought intrigued before suddenly overtaken by fear? 'Could Brittany have sent him the video and he saw me in It? No, no if Alvin had seen me there's no way he would have given me his car. That would be the least of my worries.' He realized. Looking back down at his phone Simon realized that he had less than an hour before he was supposed to pick up Jeanette. 'If she's gone this long without messaging me then it can almost certainly wait.' Simon decided, knowledge of his privacy that night bolstering his confidence.
Getting off the couch he began to walk towards his room. 'Still, no reason not to look my best for the exhibit.' He thought mentally choosing his outfit.
Jeanette was going crazy. She felt full in a way she had never felt before and it was not necessarily unpleasant. But every single little movement caused the toys inside her to change positions, rubbing against her spots and each other inside her.
Jeanette had spent nearly the entire afternoon cleaning her room. Later when Theodore was done with the cheesecake she had insisted on washing the dishes just to keep herself away from the enveloped key. Consciously she knew there was no reason not to use it. Simon hadn't told her not too and she was definitely horny enough to do it. But there was still something inside her that wouldn't let her use it, that seemed to scream at her that she hadn't earned it.
So instead she did her best to distract herself. She was currently having a problem selecting an outfit for her date tonight. 'A dress would be most appropriate, but which one?' She thought to herself. Brittany had insisted that Jeanette "diversify her wardrobe" a few months earlier so she had several different options. Eventually, she settled on a simple purple dress that had a loop secured around her neck tied to the back of the dress. It hugged her chest before flowing out past her waist leaving her arms and most of her back bare.
Looking at herself from every angle, Jeanette couldn't see any evidence of the belt beneath her dress, and she was reasonably confident that even if anyone did it would be mistaken for underwear. Grabbing the envelope, Jeanette walked downstairs, where she ran into Brittany who had just finished frowning at her phone. Looking up at her sister her eye's widened.
"Ooh la la, where are you and Simon going where you need to look so fancy?" Brittany asked after nodding approvingly at her sister.
"Just an event at the museum, the project we were a part of in school gave us contact with some sponsors who expressed interest in our work and… You don't really care do you?" Jeanette smiled at her sister seeing the blank look covering her face.
"Not really no," Brittany replied. "I got the gist of it; you and Simon are going to a fancy dance and I get to go in the treehouse. Alvin better have a homemade candlelit dinner up there or I'm going to be pissed." Brittany said irritably.
"The treehouse? Why does he want the treehouse?" Jeanette asked in confusion.
"I don't know, he wouldn't tell me, said we'd talk about it tonight. Given that you're wearing that though it probably is a good thing, be a shame to get such a pretty dress dirty in the treehouse." Brittany said shrugging her shoulders and gesturing to Jeanette. "Of course, for all I know Simon might rip it off you as soon as you get home." She said smirking.
'Oh, I hope so.' Jeanette thought to herself blushing. "I… I don't know what you mean." She replied.
"Oh puh-lease, you and Simon aren't as subtle as you think you are when you just 'happen' to go into the treehouse after every one of your dates." Brittany said teasing her sister. "Just so you know, Eleanor already left with Theodore for their picnic, so they won't be back for a while, chances are they will come back here so you and Simon will have the time to take the dress off properly in his room."
Opening her mouth to respond to Brittany's taunt Jeanette was cut off by a knocking at the front door.
"That's probably Simon," Brittany said looking down at her phone. "And Alvin chooses now to ask me to come to the treehouse. I guess I'm off, have fun tonight Jeanette." Brittany says walking away.
"You too!" Jeanette calls after her. Jeanette's heart was beating like a drum in her chest as she went over to the door. Opening it she was met by Simon's sharp intake of breath.
"Wow." Simon said, his mouth hanging open. Jeanette's heart soared, direct compliments on her appearance from Simon were rare. He simply preferred to compliment her mind instead. Still, it was nice to be admired.
"You like it? It isn't too much?" Jeanette asked while examining Simon's own outfit. It consisted of a simple dark blue suit with a lighter blue undershirt.
"You look great." Simon said quickly in response smiling at Jeanette before a slight lip quiver. "Ahh, is that the only thing you're wearing?" he asked with a slight catch in his voice betraying his nervousness.
Jeanette blushed fiercely at the implication behind his question. With a shaking hand, she held out the envelope to Simon. Looking down at it he sighed and began to speak slightly disappointed and rehearsed. "Look Jeanette, I only really left a letter because I thought it would make you more comfortable. I completely understand if you don't want to do it for real but…"
"it's the key Simon." Jeanette said hurriedly, her facing turning an even darker shade of red. "I never took the key out, and I've had… it, on all day." She said squirming slightly, the toys inside her rubbing against each other.
Simon's face contorted in a puzzled expression before the meaning of her words registered in his mind. "Oh. OH!" He said opened-mouthed as the realization dawned on him and he grabbed the envelope. "Let me see." He demanded as a wolfish grin broke out on his face.
Hearing Simon's commanding words Jeanette felt herself become even wetter than the low levels she had been dealing with all day. Grabbing the sides of her dress Jeanette slowly began pulling it up, revealing more and more of her legs until finally the belt was entirely revealed.
Simon dropped to one knee and felt at the belt ensuring it held firm and wasn't overly tight. He felt a surge of pride at his invention given that, to his knowledge, it was the first chipmunk chastity belt even invented. She's wearing it, she's actually wearing it and she gave me the key.' He thought wildly. Running his fingers down her crotch her soon felt the hooks of the vibrator and butt plug latched into place on the belt. A light tap on the toys caused Jeanette to let out a light moan in pleasure. 'Going to have fun with those later.' Simon thought grinning even wider.
He continued to explore his belt, ensuring that everything was in its place for several minutes until he felt a breeze blow into the house from behind him. Jeanette let out a quiet yelp as she felt the same breeze before her face returned to a deep scarlet.
'I just flashed the street for five minutes straight while Simon touched me' Jeanette thought shuddering to herself in arousal. His hands had felt so skilled and precise, as they always did, even though the belt. Simon predicted and found the pleasure paths across Jeanette's skin, tracing them all over her body and driving her mad in the process. Him doing so while she was belted almost caused her to collapse right there.
Simon stood up and looked Jeanette in the eye, his eyes nearly as wide as hers in the same realization. "You can put the dress back down now." He said before crushing her lips in a passionate kiss.
Jeanette dropped her dress and returned the kiss equally passionate. She soon felt the hardness of Simon's length beneath his pants as he slowly rubbed himself against her. "God, you're amazing Jeanette." He growled in her ear. "Its taking all of my willpower not to throw you to your knees right now, but if I do I doubt we'll ever make it to the party. Now let's go, the sooner we get there, the sooner we can leave." Simon said pulling Jeanette by her hand to Alvin's car sitting in the street.
Jeanette stumbled over her long dress, there was a reason she didn't wear them that often! But nonetheless, she followed Simon without complaint wondering what he had in store for her. On the way to the museum, Simon could barely keep his eyes on the road. 'Does she realize what she does to me?' He wondered as she looked at her smiling. Stopping at a red-light Simon sighed and turned to Jeanette. "I suppose we should cover some ground rules, shouldn't we?" Simon asked, worried about her expectations. Jeanette returned his gaze.
"Maybe… Maybe later. If we decide to keep this going. For tonight, I think I'd rather leave it up to you. I trust you Simon." Jeanette replied smiling nervously. "Just, nothing too crazy, okay?" She asked.
"Of course! I just wanted to make sure you were going to have a good time and…" Simon trailed off as Jeanette's words weighed on his mind. 'She trusts me. So much that she's wearing a chastity belt I made her and… No, stop it. You can figure that out later.' He thought to himself. "Just make sure you let me know if you're uncomfortable, at all." Simon said.
"I will. I promise." Jeanette said. They continued their way to the museum finally reaching it shortly before the event was set to begin. Simon got out and helped Jeanette out of her seat, taking her hand like a gentleman and escorting her to the entrance. They hand barely made it to the side walk before Simon pulled her aside.
"I completely forgot to test this." Simon said excitedly as he pulled out his phone.
'Test what?' Jeanette thought right before the vibrator inside her began to buzz unexpectedly causing Jeanette to moan loudly before it stopped as abruptly as it started. 'That apparently.' She thought to herself as she recovered.
Adjusting the settings Simon grinned at her. "That was a bit stronger than what will probably be usual tonight, but I thought I'd give you a little taste before we went inside." He said casually. "Try not to let anybody on to the fact that you're walking around stuffed with toys."
'Fat chance of that!' Jeanette thought to herself. She hadn't quite expected that burst of vibration, but she was getting soaked in anticipation of being teased even more. "I'll try." She said meekly, unconvinced of her own acting ability.
"You better if you want me to take that belt off when we get home." Simon said threateningly. 'I have no intention of leaving it on her of course.' He reassured himself. 'But it will be fun to watch her squirm.'
Jeanette's eyes widened at Simon's words, but she relaxed a little when she saw the amused glint in his eye as he took her arm. Deciding not to call his bluff, Jeanette let him walk her into the entrance hall of the museum.
The event wasn't anything major and didn't truly involve either of them, Simon and Jeanette had been invited after impressing a member of the museum's board who thought they would enjoy some of the exhibits. As they walked around and spoke to some of the other guests Simon would periodically cause the vibrator inside Jeanette to buzz making her suck in deep breaths or pause in mid-sentence, but no one seemed to suspect anything was off.
In between these conversations, Simon's hands would wander over Jeanette. Sliding down her back and gripping her rear, pulling her against him, massaging her shoulders, but never long enough to be considered improper. Near the end of the night, Simon and Jeanette found themselves speaking with the member of the board who had invited them.
"Mr. Seville! Miss Miller! How good to see you this evening, are you enjoying yourselves?" He asked politely.
'More than you know.' Jeanette thought to herself, as she clenched herself around the toy in her core. Making small talk with the board member soon proved to as boring as she had feared but her and Simon nodded along politely. Suddenly, a mischievous glint appeared in Simon's eyes that Jeanette more often associated with Alvin.
"Excuse me, I need to use the restroom." Simon said, interrupting the board member. Leaning over he gave Jeanette a peck on the cheek after whispering in her ear "wait here." As Simon walked away the board member continued his one-sided conversation while Jeanette wondered what Simon was planning.
She got her answer a moment later as the toy inside her began to vibrate, but not the entire toy as it had before, but rather only at the base. Jeanette managed to successfully suppress her urge to moan, easier in fact than she did before. Still confused she was startled and wasn't entirely able to suppress her yelp of surprise when the vibrating sensation began to move its way up the toy. It did so smoothly and slowly until reaching the top when it began moving equally smoothly down, Jeanette began to breathe heavier as she realized what it was supposed to mimic. The function slowly began to increase in both speed and vibration as Jeanette felt herself getting flushed.
Simon's sudden voice behind her made her jump. "Sorry, about that." He said, grinning and deliberately ignoring Jeanette's mortified expression. "Excuse me sir, didn't you tell us about that project in graduate school? I'd like to hear that story again please." Simon asked the board member.
"Certainly! I'm surprised you remember it, though it is an amusing tale I suppose." He said as he began the story in question. Jeanette remembered the story as well, it had taken him almost half an hour to tell before. 'At the rate, the vibrator is increasing I don't think I'll make it that long.' Jeanette thought to herself.
As the story wore on, the toy continued its simulated thrusting. The speed increased so that by 10 minutes in Jeanette could barely count the time in between the top vibrating and the bottom. Simon continued to pretend to listen to the story while smirking at Jeanette out of the corner of his eye. Jeanette began to sway her hips, eager for any kind of additional stimulation. Her face grew beet red and her breathing became heavy. Jeanette was lost in a world of pleasure as the toy inside her pulsed, eventually, she was brought out of her stupor by the board member.
"Miss Miller? Are you okay my dear? You look a bit faint." He asked. Simon stood slightly behind him, phone out while he adjusted the settings slightly smirking confidently at her.
"I… uh… I think… I'm just not feeling well, I'm going to go get some air." Jeanette said distractedly. Immediately Simon's smile fell away, replaced with a look of concern. Rushing out of the museum Jeanette soon felt a cool breeze on her hot skin. Walking towards the car she soon was on the side of the building and sat down on the grass against the wall and groaned in frustration as she realized Simon had turned the vibrator off. Sliding her hands up her legs she tried in vain to elicit any kind of feeling from her fingers to her core. She felt herself clench hard around the toy inside her desperate for the pleasuring she had been feeling just a minute earlier.
Simon soon excused himself after disabling the vibrator. Walking with an urgency in his step he made his way to the door. 'I shouldn't have pushed her so much.' He thought worriedly to himself. 'I was so busy making her squirm I must not have seen her trying to get my attention…' Turning around the corner he saw Jeanette sitting in the grass groaning. "Jeanette, I am so sorry. I didn't mean to…"
"Simon. Pleeeeease! Turn it back on!" Jeanette begged as she heard him. Turning to her side she looked Simon in the eyes, desperately trying to stimulate herself through the belt. "I need it, I'll do anything please just turn it back on." She moaned. Simon simply looked at her. Jeanette's dress was hiked up so far, he could clearly see the belt. Juices clearly leaked out through the sides showing just how aroused Jeanette was.
'She's absolutely loving this!' Simon thought to himself excitedly.
"What do you want Simon? A blowjob like you said earlier? Pleeeease just stick your cock in my mouth!" Jeanette begged as she closed her eyes, focusing on herself. "I'll swallow everything! Just let me Hmghf!" Jeanette let out a muffled squeaked as Simon roughly pulled her mouth around his member.
"If you insist." Simon said releasing his hold on Jeanette's head. Soon Jeanette was bobbing her head up and down on Simon's shaft. Running her tongue over the underside she lightly sucked on his tip causing him to let out a low moan of pleasure. "That's it Jeanette." Simon said, acting on instinct he was running his hand from the top of Jeanette's forehead through her hair to the back of her head, driving Jeanette wild. "That's a good girl. Take it a little deeper. Fuuuuck yes." Simon moaned as Jeanette forced herself to take more and more of him in her mouth.
All too soon Simon felt himself reaching his limit. "That's a good girl Jeanette, I'm almost there, I'm about to cum Jeanette, remember what you said and drink in all!" He said shooting his load in Jeanette's mouth. Jeanette swallowed every spurt as it shot out, slowly savoring the musky, salty taste. At last Simon was spent and Jeanette slowly licked the last of his cum from his tip.
Simon looked down at Jeanette who looked up at him. Her focus on herself had faded while she did her best to bring Simon to orgasm, but the need hadn't disappeared. Merely taken a backseat to her desire to please her lover. Simon looked up and looked around, straining his ears to hear anyone around. Satisfied that no one was nearby he looked back down to Jeanette. Taking out his phone he turned the vibrator back on with its thrusting function. However, he set the vibration settings as low as it could go and the thrusting speed as slow as possible. Jeanette began to shudder as she felt the toy begin to tease her.
"You asked me to turn it back on, you didn't ask for the same settings," Simon said smirking at his girlfriend quivering on the ground. "Now come on, we're going home," Simon said as he helped Jeanette to her feet enjoying the feeling of her pressing against him. When we get there, I am going to do my best you feel like a puddle of pleasure.' Simon thought to himself as he got in the driver's seat.
As they drove back home Jeanette was lightly humping at the air, trying anything to increase the pleasure torturing her. The toy within her still buzzed slowly. 'Is he trying to drive me crazy?' Jeanette wondered while letting out a whimper.
After what felt like hours, they made it back to Simon's house. Pulling into the driveway Simon noticed that the door to the Chipette's house was slightly ajar. Based on the sounds coming from inside he had a pretty good Idea why. Turning to Jeanette he said, "I'm going to go shut that door, I want you in my room, on my bed, as naked as you can be facing towards the wall with the door open."
Nodding weakly Jeanette began to walk towards the house, swaying with each step as she tried to control herself. Half crawling up the stairs she finally made it to Simon's room. Slowly she pulled off her dress, the feeling of it moving past her skin when combined with the buzzing device inside her was almost too much.
Soon she was on all fours facing the window, her belt still wrapped itself around her hips as she unconsciously wriggled her ass at the door behind her. Through the window, she could see Alvin and Brittany having sex in the treehouse. Though she was still too far away to see any detail, the sight nonetheless caused her imagination to run wild.
While Jeanette was lost in thought Simon entered the room and admired the view of his girlfriend's ass, swaying back and forth. Realizing she hadn't noticed him come in Simon surprised Jeanette with a firm slap to her ass. Hearing her moan in pleasure Simon grinned wolfishly. He had already removed his shirt and bent over to growl in Jeanette's ear "Keep your hands right there, I am going to take the belt off, but if you try to touch yourself, you will regret it."
When Jeanette moaned her consent, Simon stepped back. Slowly, he noisily pulled the key out of the folded envelope. Stepping forwards yet again, Simon traced the key up Jeanette's leg teasing her even more, sliding it around her hips, he drew little circles around the hidden pocket where the padlock was hidden.
Sliding it out Simon unlocked the belt and pulled it off slowly. It come off, pulling the toys out with a pop! As soon as it was off Simon was hit by the deep, musky, slightly sweet smell that emanated from Jeanette's slightly gaping hole. She dripped onto the sheets beneath her, gripping the sheets below, unknowingly extending her claws and tearing the sheets in a struggle to keep herself from touching her aching clit.
Simon was instantly harder than steel and realized that Jeanette didn't need any more teasing or foreplay. Grabbing her hips, he shoved himself in stretching her out around himself. Jeanette moaned in absolute pleasuring nearly reaching her climax from the insertion alone. Simon quickly began thrusting hard and fast. Jeanette signaled her agreement with wordless whimpers of pleasure. She had been teased all day and she was more than willing for this.
Simon for his part was feeling mad with power. 'I did this to her.' He thought in absolute desire, 'I made her want me this bad. I am going to make her mine. Give her the reward for her hard work today.' Increasing the speed of his thrusts he felt his climax coming soon. Bending over he whispered in Jeanette's ear. "Cum." Was his simple, yet firm, demand,
Jeanette's eyes rolled in her head, she opened her mouth letting out a long drawn out moan. She clenched hard around Simon's shaft milking him, desperate for his cum. Feeling Jeanette's spasms, Simon soon reached his own climax, unloading himself into Jeanette.
Both chipmunks panted with exhaustion before collapsing in Simon's bed. Laying down on his back, Jeanette soon laid her head on his chest while Simon slowly ran his hand across her head. "We need to wash the belt before we do that again," Jeanette mumbled as sleep began to take hold.
"It can just go in the washing machine," Simon said bemused, but Jeanette had already fallen asleep. Smiling, Simon closed his eyes and allowed his own exhaustion to overtake him.
AN: Wow, when I said, "A little longer" I swear I wasn't thinking "Twice as long". Still, I felt like I needed the extra thousand words or so to set up the next couple chapters, which is funny because the next few chapters (5-8) are just to set it up so I can write pointless smut instead of plotty smut. This is getting a lot more plotty than I anticipated but I like it.
I am going to try, no guarantees, but try to release at least one chapter a week.
I hope this chapter read a little smoother than the previous one. Reviews and criticisms are more than welcome and thank you for reading.