Step Sister Corruption 357

Day 210 Bet

Sarah aka Ginger

I don't know if I should feel under dressed or over dressed as my little number spoke volumes of what I was and what I wasn't.

What I was supposed to look like was Jason's 'Secretary' but my dress said everything BUT Secretary.

Recently I had agreed to be Jason's secretary which meant two things:

* One, I would be traveling with Jason again.....Yay!!!

* Two, I would be away from my family.....Booo!

I mean yes I knew that both Gabe and Kelly could take care of themselves and I really didn't have to worry about them. The real issue was being away from Samantha AND Jasmine as they were at the weird age that yes they could probably take of themselves though probably not for very long.

Like Samantha could probably take care of herself and be trusted to not destroy anything....or set the house on fire.....I hope.

And Jasmine could also probably take care of herself.....sort of but it wouldn't be very long.

Jason had told me that the girl's would more than likely be able to take care of themselves as long as there was food in the house and we should start trusting them to show us that they can take care of themselves.

Besides Gabe and Kelly were right next door if anything happened or needed to be taken care of. And the girl's both knew Gabe's and Kelly's Cell Phone numbers plus they also could call Summer or Gabe's new secretary Morgan if anything came up.

Which I know Jason was right we needed to start allowing the girl's that they could handle being alone as Jason's schedule was always busy.

So when Jason told me that we would be leaving today for a series of meetings with his investors as we would be sitting around in one location as his 'investors' were more or less ALL OVER THE WORLD, I started packing....and prepping.

I quickly started making pre-made meals for the girls and luckily was able to make enough for a week and created a variety of pre-made meals for Samantha and Jasmine. I also included some instructions on how long to cook each item.

Then I quickly started packing MY suitcase and Jason's. As Jason made a last minute change in my attire as he removed my ahem modern proper outfits for more.....let's say risqué outfits. The asshole actually took out my designer suits and replaced them with my 'suits' from my studio. Then he added some 'items' from my studio in the bag.

And here we are as I sat still semi shocked in a private jet just looking around the roomy plane sitting still unsure if I was dressed the part of Jason's secretary or not.

I was dressed in one of my zip up dresses but instead of the zipper being in the back it was in the front. The dress has nice long sleeves that go down and 'almost' cover my hands but the fabric around the sleeve is so sheer it was almost see thru and at the pit level you could 'almost' see what type of bra I was wearing, not that I was wearing one currently. The bodice, or top, part of the dress is fairly snug not being too loose or too tight so I fully zip up the dress as my girls aren't being squeezed together. The skirt, or bottom of the dress, is fairly loose so walking is fairly simple and not constricted as it flows down to a little passed mid thigh just above my knee. Then there's the belt band around the middle to close up the dress and show off my curves.

Now 'normally' this dress is something I would probably wear if I were going out and wanted to turn heads.

Definitely something I would wear on the set as I teasingly unzip slowly for my viewers.

But it was something I would definitely not wear to something say like a Parent Teacher Conference for instance. I wouldn't wear this at say an actual work place...at least not if I wanted to start rumors.

Then there was the 'added' items that Jason suggested I wear hiding UNDER the dress. Like the plug/wear I was wearing which I was surprised was actually really really comfortable....for a butt plug that is. Usually with butt plugs I have to avoid sitting flatly especially with LARGE ones as that can be extremely uncomfortable. Usually the jewel or the round part that covers the asshole can sometimes be fairly bulbous and the cushion between my asshole and the fat in my cheeks isn't enough to keep from pushing the plug deeper when sitting. And if the plug is fairly large that extra push when sitting feels like its trying to tear its way as it goes deeper. But this plug/wear the plug is angled and the bottom is this thin flat piece so when I sit there's a lot of room before something 'pushes' against it. And with it being angled like it is if it were 'pushed' it would simply slip deeper instead slip higher and ripping.

Then there's the undies attached to the plug.

And the vibrator lodged in my pussy that was already dripping from a two day edging session that Jason and I were on.

Then there was the twin clips on my nipples that had a small chain attached to them.

All these items were currently part of my edging program that Dr. Hill suggested I start undertaking.

That was my regimen.  Jason was much more lucky as his regimen only consisted of a urethral plug though that plug may be coated in some special oils to keep his dick hard for long periods of time without damaging it.

None of our respective devices didn't help our situation but it did do one thing.....or at least in my situation.  The combined items did keep me on the edge of being horny....constantly.

I looked over at Jason who seemed to be more relaxed as he went over the papers in his binder closely than I was as this was the first time being a private jet and really didn't know what to do.

We had only been in the air for maybe 30 or so minutes as I looked at the TV that showed where we are and where we were going as it showed we would be landing in Montreal in another 2 or so hours.

I looked around the confines of the private jet noting it did look nice and quaint where maybe eight people could fit in the small area but it was only us and the pilot and co pilot on the plane. Though I knew it was expensive it still felt plain....beautiful but plain none the less.

I spoke, "So remind me what we are doing?"

Jason didn't look up from his paperwork, "I told you we're going to Montreal to meet with all our investors to go over the numbers and give them their returns for the year."

I looked around, "All of which affords us to fly on a private jet?"

Jason lightly chuckled but still didn't look up from his paperwork, "More like one of the investors offered the jet to fly us there and back without having to deal with customs and what not."

He looked around the plane for a moment before looking back down at his paperwork, "Not that I'm complaining."  He smiled at me, "Besides it would be rude to say no to a Prince."

Prince?

I felt my jaw drop as I spoke in a near whisper, "Prince?"

He nodded, smiling confidently, "Yep."

I squinted at him after the initial shock had run its course, "How the fuck did you land a Prince?"

Jason shrugged, "Pure Luck I guess.  I happened to be doing my returns like we're about to do.  The Prince overheard me talking about the year's returns to one of my investors.  He beckoned me over after I was done and asked about my investments.  I kind of laid it out for him and he seemed intrigued."

I blinked at him hearing this as he continued, "After he seemed intrigued he offered to invest some money with me.  At first I told him I was pretty solid on all my current investments but he insisted that I include him in my business holdings which seemed weird.  I told him an unbelievable number and he wrote me a check on the spot."

He leaned back, "After that I was able to purchase nine more businesses and expand our portfolio twenty fold."

I blinked at him as this was the FIRST time Jason actually talked business in front of me and was actually telling me the truth.

I spoke, "How much did he write you?"

He shrugged, "Fifteen Million."

I blinked at the number before speaking, "And how much is HIS investment returning?"

He looked down at the numbers, "This year it'll return him 10.5 million."

I felt like my brain just exploded as I heard the numbers for the first time as Jason continued, "Granted he is the only one getting a LARGE check.  The rest usually range from $150,000 to about $700,000."

I looked at him, "How many businesses do WE own?"

Jason looked up and I watched him start counting as he pointed to a map that was ONLY in his head of all the locations.  He did that for about a minute or two before he finally answered, "In OUR town alone there are about 19 businesses where we're the sole owners."

I blinked and nearly shrieked, "19???"

He smiled at me, "Come on honey you didn't think OUR website was our ONLY business did you?"

I looked at him and slowly shook my head.

I knew Jason had been slowly getting investors over the years building a 'portfolio' while I was doing OUR website.  But to hear how much he had grown that 'portfolio' was mind boggling.

I looked at him, finding myself in complete awe in the man.

I looked around confirming we were the only ones in the plane as I leaned over and whispered, "How much are WE worth?"

Jason looked at me smirking, "You really want to know?"

I nodded slowly.

Jason smirked, "A LOT."

I squinted at him, "That doesn't help babe."

He chuckled, "Let's just say we're close to that third comma and leave it at that."

I blinked as he said third comma but spoke just to confirm, "Third comma?  Meaning Billion?"

He looked over at me smiling as he slowly nodded before amending, "Granted it's still far away."

He leaned back looking at me, "Granted MOST of that is tied up in land, businesses, stocks, investments, pay roll for the employees, living trust for the kids, yada yada."

I sighed as I looked at him, "OOkkk....how much are we worth WITHOUT all that?"

He shrugged, "Couple mil or so."

COUPLE OF MILLION??? OR SO???

He looked at me as I was sure my jaw was hanging, "And if you knew that you would absolutely go NUTS trying to burn down our credit card."

I squinted at Jason and spoke very carefully, "I don't know whether to rip off your pants right now OR choke the living shit out of you right now."

He chuckled, "I vote for the first option."

I smirked at him as I silently thanked my lucky stars that Jason NEVER found out about Gabe as I was suddenly very very happy I decided to rekindle my relationship with him.

I licked my lips contemplating which option would feel better at the moment as I already knew which way I was already leaning towards thanks to the devices currently residing on me.  I smirked at him, "Under ONE condition."

He nodded at me, "Shoot!"

I spoke clearly, "I want to go on a shopping spree when we get home.  And I NO LONGER want to hear about HOW MUCH money I spend."

He looked at me, "Come on babe there has to be limits or we would have never gotten to where we are."

I squinted at him, "Limits?"

He nodded, "Yeah limits."

I licked my teeth wondering if I could rip out his throat with them before going against the idea as I knew I was getting irritated.  I clicked my tongue, "Alright.  What 'limits' were you thinking?"

He looked at me, "Now that you know we're worth more than you expected.  I still want you to keep your spending down babe."

I felt my fire go up as I tilted my head, "Remind me how much you LOVE your dick?"

He looked at me for a moment before he sputtered, "I'm sorry?"

I growled, "Your dick!  How attached to it are you?"

He spoke unsure, "Uhhhh kind of attached babe."

I spoke, "Shopping Spree.  I want it."

He sighed, "Fine!!! You can have your shopping spree."

I smiled sweetly at him, "Unlimited shopping.  No more bitching period!!!"

He groaned, "Just promise me you'll keep your shopping UNDER 20K."

I smirked at him, "At EACH location, sure."

He looked up and groaned more.

I smiled as I decided to sweeten the pot as I unbuckled myself from my chair.  I got up and grabbed his paperwork out of his lap putting it in the seat next to him as I straddled him as I cooed, "Come on babe spending money ALWAYS gets me," I leaned down and huskily whispered into his ear, "wet."

The moment I said that I felt him immediately poke into me causing me to lightly chuckle.

Good I got his attention!

I pulled back and wrapped my arms around his neck leaning back slightly, smiling at him, "And I promise to not go overboard.  I just want some cute purses and maybe some cute heels to go with them."

I smiled as I watched him groan, "Come on babe you already have at least 60 'cute' purses and a closet FILLED to the brim with shoes and heels."

I smiled as I coyly smiled, "I'm not that bad."

He looked at me flatly, "I bet you if I pulled EVERY pair of shoes you have and have you wear them just one day you wouldn't have to put on the SAME pair for at least four months."

I smirked, "Are you saying I have OVER a hundred pairs of heels?"

He shook his head, "No but if we combine every pair of sneakers, flip flops, flats, boots, and everything in between I bet you have at least 100 pairs of shoes."

I smirked, "I smell a challenge."

He looked at me and spoke confidently, "Just stating the facts babe."

I looked at him, "And I'm saying I don't have a hundred pairs of footwear."

He smiled, "Want to make a bet?"

I looked at him skeptically, "Maybe.  What are your terms?"

He thought about it for a moment and smiled, "If I win....." he looked at me, "I want to fuck you in the butt."

I blinked as I hoarsely spoke, "You want to do me anally?"

He smiled, "Only if you're still a virgin back there."

I gasped, "You know I am babe."

I didn't dare mention that I almost lost it to Gabe if I didn't start going to therapy.

He smirked at me, "Good," he pulled me into him and he growled with a smile, "because I want to POP your anal cherry."

I gasped, "You wouldn't dare!"

He smiled almost wickedly as he nodded, "I want you babe...ALL OF YOU.  And that means I want your ass."

I looked at him semi shocked and suddenly really really aroused as I felt needed again by Jason as I quickly spoke, "Fine!  If I win," I smiled at him, "then I pop your anal cherry with the biggest strap on I can find."

Jason smiled confidently that instantly terrified me as he spoke the words that instantly made me sweat in fear, "Deal!"