Isabelle & Simon Ch. 11

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Isabelle & Simon, The New Beginning Has Arrived!
2.8k words
4.68
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Part 11 of the 11 part series

Updated 06/15/2023
Created 05/30/2021
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AN: Hope you enjoy the chapter; I know it's been literally forever since chapter 10 was released but I'm lazy and just super busy irl. As promised though, I won't ever abandon the series or leave it unfinished even if it takes me a while to write.

Disclaimer: Isabelle & Simon are BOTH over 18! Any & all characters involved in sexual situations at any time or point in the story are over the legal age of 18!

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I wake up to the feel of Isabelle's exquisite body against mine. Her butt is pressed against me, and my dick is lodged firmly between her amazing ass, I struggle internally for a few moments before reminding myself that there are more important things planned for today.

I carefully and successfully extract myself without waking Isabelle up. Heading into the bathroom I take a quick shower; I wash my hair remembering to use conditioner and wait the full 5 minutes before washing it out. After I'm done showering, brushing my teeth etc. I pull my phone out and check that the plans I have laid out will go off without a hitch.

I'd booked tickets for ice-skating, a hobby that we both loved and used to do a lot when we were younger. I also had reservations at Izzy's favourite restaurant, an Italian place called Milano's; we loved the pizza there. It wasn't a super fancy place or anything but I knew Izzy would prefer this to anything else. The final thing I had planned was a hot air balloon ride, which doesn't sound like the craziest thing ever but Isabelle had been wanting to go on one since we were like 5 years old. I was terrified of heights though and had never obliged her request, so I'd be taking the plunge finally in order to propose to her while we were a couple hundred or thousand meters off the ground. My biggest fear now was dropping the ring, that would be really bad.

After checking that all the bookings were sorted I went back to wake Izzy up. I walked in and instead of waking her straight away, I sat down and watched the rise and fall of her chest as she slowly breathed. There is nothing more relaxing, more soothing and more beautiful than watching Isabelle sleep. It is something that leaves me at peace, my heart aching with how much I love her. Eventually I do have to shake myself out of my reverie and shake her awake or the days plan would start running late.

Izzy gets up with a grumble, which turns into a smile upon seeing me. She gives me a quick hug but refrains from kissing me and instead hurries into the bathroom. The next hour passes in a flash as I wait eagerly for Izzy to emerge. The door eventually opens and Izzy saunters out naked and oozing sexiness. My poor dick gets so hard, so fast that it feels like it's punctured a hole in my jeans. Izzy winks at me before disappearing into the hallway and into her room to change.

She emerges half an hour later in a simple black jeans and game of thrones t-shirt with Cersei and Jamie Lannister plastered across the front of it, along with a pair of her favourite sneakers.

Izzy was trying to kill me I swear, I wanted to grab her, bend her over and fuck the living daylights out of her, I was so horny. I could picture myself pounding into her, going so deep I reach parts of her I never knew existed, and so hard that we leave a dent in the wall. I calm myself and my raging erection down with the thought of mum and dad seeing that dent or even worse, walking in on that scene, and the resulting cluster fuck my life would then become. With Cersei and Jamie Lannister now fresh in my mind I was picturing little Izzy's and Simon's running around the house. Which brought a tear to my eye which I quickly wiped away.

Izzy comes over to me and smiles before leaning forwards and kissing me quickly. It's just a quick kiss as we are in the hallway and mum or dad could walk in at any moment.

"So what's the plan for today Si?" Izzy asks with a smile.

"Well I thought we could go out and have some fun, do some things we haven't done in a while."

Izzy's smile grows wider, and she is about to ask what it was I had planned but I silence her with a kiss, a wink and a smile.

"Come on let's go out, Breakfast awaits and then a day of fun."

Izzy giggles and I grab her hand before heading downstairs. Mum and dad are still in their room, so we leave a note for them on the fridge to let them know we've gone out and won't be back till evening.

We head out and get into the car, Izzy flips through the radio stations as I drive us over to RocoMamas for breakfast. When we arrive I can see Izzy's eyes light up as the memories of us coming here for Cheesy Nachos during high school every week surfaces. I smile at the look plastered across her face as I drag her inside, we sit down and when the waiter comes by, I order 2 plates of Cheesy Nachos for us along with coffee for Izzy and a white-hot chocolate for myself. We spend breakfast reminiscing over our childhood and bringing up old memories. After we are done I pay for the food and we make our way back out to the car.

"That was so fun Si, what's next?"

Izzy is positively beaming and she looks like an angel with a wide, happy, carefree smile on her face and the look of joy shining out her eyes.

"Wait and see Izzy" I reply with a grin.

She pouts and as I start the car up and turn out onto the road, she unbuckles her seatbelt and bends over and unbuckles my seatbelt. My belt and jeans follow quickly as she yanks my pants down and frees my penis from the constraints of my boxers.

She stares at it for a second her eyes slowly glazing over as she licks her lips. She bends down and slowly envelops my dick with her glorious mouth. The feeling is heavenly, and Izzy proceeds to run her luscious lips up and down my shaft causing new sensations with every movement. Her tongue flicking out to lick here and there to tease my rock-hard cock, as if I wasn't ready to burst already from her attentions. She slowly builds up her pace, my dick disappearing into the depths of her mouth with every cycle. She starts to alternate her speed and angle causing new sensations with every movement. She pulls herself off completely, leans over and kisses me before continuing her worship of my cock. As we go over a bump, Izzy is coming down on my cock and I end up buried in her throat. She gags but recovers and continues to slurp away at my cock. The feeling of her throat muscles around my dick massaging it cause me to lose control and my eyes briefly roll back as I pump wave after wave of cum down Izzy's throat and straight into her belly.

Isabelle pulls herself off me and coughs a few times before recovering.

"That was amazing baby brother, wow!"

I'm focused on driving straight after my momentary loss of control had left me veering into oncoming traffic. I'm still recovering from the strength of that orgasm, while trying to keep us on the road.

"That was amazing Izzy, wow, just wow!" I say after reassuring myself that I wasn't about to lose control of the car.

Isabelle smiles and hums to herself, a pleased smirk plastered across her face, while I drive us to our next destination. We arrive at the ice-rink, and they scan the QR code on my phone before giving us our skates and letting us in. Izzy looks around taking it all in, this is the first time we've been to the ice-rink since Isabelle started acting like a bitch towards me.

We take our shoes off and put our skates on before Isabelle grabs my hand and leads me onto the ice. She was always a talented skater and it's immediately apparent that she has lost none of her old skill. She leads me across the ice, as graceful and beautiful as a swan in flight. We glide back and forth across the ice either holding hands or wrapped up in one another's arms. The 2 hours fly by in no time and soon we are called off the ice to collect our shoes and put them on. After we are done Isabelle turns to me, kisses me on the cheek and sinks into my arms as I wrap her in the loving, protective embrace of my arms.

"Thank you so much Simon, that was amazing bro. I love you so much."

"I love you to Isabelle, you're my whole world now baby."

Isabelle rests her head against my chest and we stand there in one another's embrace until Izzy finally lifts her head ready to go.

We head over to Milano's next for lunch, I order a pineapple pizza for us to share along with a strawberry milkshake each. We spend the next hour just enjoying one another's company, eating our pizza, drinking our milkshakes and talking about whatever comes to mind. We finally finish our lunch and I pay the bill, before we make our way back to the car. We set off for our final destination, the hot air balloon place.

The drive there takes about half an hour as it's located pretty far out in a large open field. Izzy grows more and more excited the closer we get as she has obviously realized where we are heading, she looks over at me a couple of times but doesn't say anything. When we arrive I show the guy working there our tickets and he assigns us a guide who takes us over to the hot air balloon we would be taking up. He goes through all the safety details before finally waving us on and letting out the rope. At first I'm a bit afraid as my phobia of heights kicks in but after a while I remind myself that it's just me and my beautiful sister here with an amazing view and a nice strong rope attached to the ground from our balloon, which allows me to finally enjoy the view.

"I can't believe we're up here Si." Izzy says out of the blue.

"I know you've always wanted to try it Izzy so here we are."

"I love you so much Simon, Thank you for today!"

"I love you sis."

I reach into my back pocket and take out the box with the ring in it. Isabelle can't see what I have in my hand but when I go down on one knee in front of her I can see realization strike her. I open the box and with the ring now in plain view I ask her.

"Isabelle Rhea Rosales, Will you marry me and make me the happiest brother alive. I love you and I can't picture my life without you."

I had planned out a much longer speech I'm pretty sure, which included a whole bunch of how even if the world thought it was wrong, they were the ones who were wrong as there was nothing truer then our love along with a whole bunch of reassurances as to how we would make it all work. But that all slipped my mind in the moment as I waited for Isabelle's answer.

I'm pulled out of my internal thoughts when I hear Isabelle sob. I'm about to get up to see if she is alright when she starts nodding her head vigorously, with tears falling down her cheeks.

"I love you Simon, Of course I'll marry you! I can't picture my life without you in it every step of the way."

I place the ring on her finger and stand up, I wrap my arms around her and pull her close before kissing her the forehead, then kissing her eyes, her cheeks and finally her lips.

Before I know it she is clawing desperately at my clothes as we end up on the floor of the hot air balloon. My shirt disappears in record time as Isabelle swiftly strips me naked, with a insatiable hunger burning in her eyes as she looks at me. Her clothes quickly follow mine and her glorious body is exposed to my eyes. I grab her breasts in my hands and squeeze them as Isabelle positions herself above me. She is so soaked her juices are leaking onto me and she panting like she's in heat. She mounts me and as she slides down my cock the sigh of relief which escapes her lips nearly causes me to explode right then and there. She starts sliding up and down on my cock, faster and harder until she is riding me like there's no tomorrow. Her breasts are bouncing up and down as I alternate between squeezing them and gripping her thighs for an extra second to keep her impaled on my dick a second or two longer. She shows no signs of tiring though she does start alternating her angle and speed to keep me guessing. Each time she slides back down my shaft I feel like I'm in heaven. Her pussy feels like it was made for me, with how perfectly we fit together, and I know I'm not going to hold out for much longer.

"Izzy I'm going to cum baby. I can't hold out any longer."

"Good, Put a baby in my belly little brother." Izzy gasps out as she continues to ride me.

I explode my dick buried inside of her as I count her insides with liberal amounts of sperm.

Izzy has slowed down finally, but she hasn't come yet and I'm still rock hard even after just filling my sister up.

I push her down and get on top of her before sliding myself back into her welcoming depths. I thrust in and out of her and she begin's holding her breaths, then releasing them in small whimpers as her orgasm draws closer. I roll my hips a little as I thrust, trying to increase the sensation for her of my dick sliding into her tight canal. One of my hands moves up to massage her breast, and she lets out a loud moan.

"So close, baby. I'm so close." She whispers, nearly to herself.

I could feel my own orgasm building again as I take in the erotic vision below me. She was the loveliest and most exquisite creature I'd ever seen and seeing her losing herself in ecstasy was something that had always rattled me to my core. It felt magnified tenfold by this moment, our bodies joined together as one.

"That's it, beautiful. Cum for me Isabelle." I say as I feel the walls of her pussy clenching hard against me. She lets out a loud cry, her quivering thighs gripping my hips as tightly as she could. Isabelle bucks hard against me, her chest heaving and forcing out a series of loud cries as wave after wave of her orgasm slam through her body. My own body propelled towards my own orgasm in response to her cries and I groan out her name as my cock releases a jet of semen into her body, triggering a second orgasm from deep within her. She shakes violently beneath me as my dick continues to erupt, bathing her walls with my cum.

I look over at my watch and see our hour is nearly up. We clean each other up as best we can before the rope starts to pull us back down to earth. We thank the guy who helped us and head back to the car and drive home. We are both tired out from our hour-long fuck session in the sky and I can tell from Izzy's dreamy gaze that she wants nothing more then to snuggle up against me and fall asleep in my arms. When we reach home Isabelle heads inside to clean herself up while I check the car for any stains as Isabelle is still walking around pumped fill of my cum. I head inside and see that Mum and dad are still away so we change into our night clothes and head to my room where we lie together, Isabelle within my arms, her cute butt pressed against my dick.

I love my big sister and she loves me back, I had proposed and she had said yes, our life together was just starting and I couldn't wait to spend the rest of my life making Isabelle the happiest, most loved woman on the planet.

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PrinceLukePrinceLukeabout 1 year agoAuthor

@ScottishTexan You aren't tripping, The story is set in the USA more or less but you are also right about some of the observations you've made. I have referenced my home country of SA here and there with things like the cricket mention, RocoMamas etc. It is purely just a nod to SA and shouldn't be taken literally in the context of the story. I honestly didn't think anyone not from SA would even notice so very glad to see you have and even cared enough to comment about it. To round things off, Story is in the USA, I just like to leave little nods to home here and there.

ScottishTexanScottishTexanabout 1 year ago

Maybe I have my wires crossed, but at one point you placed the story in a choice of the USA, UK, or Canada 🤔 by having Simon shopping for jewelry at a store named Jared's. But now you have placed him firmly on the African continent by having breakfast at RocoMamas. Does Jared's Jewelry have locations in South Africa? I couldn't find information confirming that premise. I know that you mentioned cricket between South Africa and Australia before. I suppose I've made some mistake assuming that there’s a continuity error here when there probably isn't. I remember reading in the comments that the troubles in South Africa were impacting your writing. But I never made any assumptions that you set the story close to home as you wrote it. 4/5

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