Wanna Bet? Ch. 06

Yawn. I'm tired but I always have trouble falling asleep on a jet. I'm flying in a chartered private Lear Jet with my smoozer, head of security, and the Countess. They met me at the airport at 4am after I dropped off Trixie for an after-hours party and now we are headed towards Vegas for a very large backroom game with some big players. Jessica will be coming later, so the Countess will be the official woman for the first part of game. My smoozer is briefing me on a couple of exclusive parties I'm invited to and the head of security is bringing me an update on a couple of items. My intel section will brief me at my Vegas suite. I actually have a quarter of a floor of a major casino on the strip as my personal apartment (won it from the owner in a special bet).

Of course, the fact that they are all naked and playing with me and each other might also be a reason I'm not sleeping. My head of security is a redhead named Diana who used to be a cop and her story is a fun one.

But that's a story for later.

You want to know what the fuck happened with me and Dr. M. J. Stannoer. The bitch that beat me in a game of poker when I tried to enthrall her and then used me like a sex pet. Well, I guess like wasn't the word. I WAS her pet.

For a while.

I woke up the next morning with a simple "Wake up my pets." I struggled to my feet as I was still shackled and the doc was standing there in a silk bathrobe. She sat down and spread her legs. She smiled and said "Please me pet. Do your best."

I did and she was very happy. I mean eyes glassy and voice dopey happy for a while. She then unbound us and had us clean up and then dress. Then Amy made her breakfast, and I helped her dress. Just stood there going "Yes Milady. You look wonderful Milady. Certainly Milady." Freaken pissed me off.

But there was no helping it. She had me.

After she was dressed and did some official work, she had me go next door and bring Jessica over. I did and then I had to command Jessica to strip down like we did, and then she and Amy gave the doc a wonderful threesome while I had to stand there and beat off. Then she let us go and we flew back to the U with some guidance.

That next two weeks were busy for us. The doc had me in her office every day. It was easy for her to get some time off for me from some classes and she simply fixed a couple of my math classes and gave me a passing credit so I had more free time to practice her system and on the fly modifications.

I can't really explain everything about the system but it is essentially a living system that changes literally every hand of a game. Hard to master, extremely hard. Also hard to catch. But the doc was a tough teacher and she did not take kindly to slacking off.

She put my women to work doing research and scouting games and players. Nina was already a great play-tester and the doc kept her on that. Jessica and Amber did research on games, casinos, and so on. I practiced my ass off. To her credit, the doc was good to her bet and she made me a monster player on any card game, dice game, or wheel game.

The doc did not care one bit about sports, or horses, or dogs. We had some arguments about that as I stated that we needed to be hit the whole thing while the doc's system was only on game gambling. It was the lack of money that convinced her that we needed to play the track, that and the connections to other games. She was a lot bolder than I was at the time, and I had to warn her that cleaning out a game every night was going to get us banned and kill the golden goose, so she had to throttle back after a week.

But damn what a couple of weeks.

We had no sex or fooling around while she worked the system for the first week. We did a 48 hour play test on every type of game we could think of that first weekend. Not even a sexy dress was allowed. The next week she sent me out and I came back loaded.

I cleaned out the backroom at the track to a tune of $87K. I completely broke that asshole that set me up and got all of this shit started. That was fun, but I could tell I pissed off some folks. But everyone has "a really good night" occasionally so they let it slide. But I could tell I would not be coming back if I did that again.

I then hit the underground games, four in all. I cleaned each one out and netting just over $100K and that included a game that had a pretty seedy reputation that I had avoided until then. The doc actually had me escorted by some off duty campus cops on that one (probably a good thing, I was followed back to the frat house).

It was telling the doc that we needed to not be so over the top that I figured out her first weakness. She had no empathy for humans. None. The concept of emotions and being knowledgeable about how humans feel was alien to her. Her world was numbers only and you could understand it pretty quickly once you got to know her.

It took Jessica, Nina, Amber, and me nearly two hours to convince her to not do a repeat performance of our first week. The idea that we could be banned for being too good simply didn't compute with her, and the idea that we needed to actually lose some in order to keep seats at tables really threw her through a loop. But we did finally get through to her that we would be out of options if she didn't listen to us and she finally did.

That actually led to the second weakness I figured out. Well, really it was part of the same thing. How can I put this? The doc honestly didn't think of other humans as "human". They were resources. I think the only other humans that she actually understood as human beings were people like her. Other wicked smart people who could stun a whole room into silence with their brains. Anyone not on that level was beneath her and the idea that she should treat them as real people? Yeah, never crossed her mind. Not once.

And that was a BIG mistake.

I'm not an asshole. I know, I know, I have enthralled dozens of people in my lifetime. I have completely remade some people, like Jessica, Amber, and Nina to name a few. I have turned some people into complete bimbos or morons, or turned some "good" people into very "bad" people. Yeah, I'm not on the short list to sainthood.

But here is the thing. Call it caution or call it empathy, when I change up a person I make sure one of the bets always includes LIKING the change. Enjoying being arm candy, enjoying gambling, enjoying living the high-roller jet set life (honestly, how hard of change is THAT one?), the point is that I rarely leave someone changed, but knowing they have been changed and still having the same damn mindset.

Seriously, why would I do that?

I had found out about my teachers having free will and how they got out from under me. I always made sure that my thralls didn't want to get out from under me. Maybe not fully loyal all the time, but I made sure they never hated me for the change. Even Trixie loves what she is and does and that was a forced changed in a major way that turned someone into something they NEVER wanted to be. Even if I gave her a choice of going back to her old self, she loves the new her so much she doesn't want to.

The good doc though? That thought never once crossed her mind. She never gave me any orders to adjust my mindset and she could have. She never ordered me to do any of that to my women, hell; she went out of her way to repeatedly remind them that they were now HER women. Even Amy, who had been kind of her submissive pet until I got her, was treated that way.

I picked up on it fast. As in about one day fast. My first order to everyone was to keep it quiet. I didn't want the doc to know she had a whole group of thralls who were not happy under her rule. Then I started getting everyone to gather info on the doc. Habits, work, and since we were now on the inside it was a lot easier.

But it wasn't until that second weekend, the one after I had cleaned out nearly every game in town that I found her next weakness, and that turned out to be the key. Well, one of them anyway.

Friday after my game the doc had me, Amy, Nina, Amber, and Jessica over to her place near campus. She was proud of her pets (she actually called us that), and said we would get a nice reward tomorrow evening. She then gave us directions to a large house outside the city on a very private lot and instructions to all be there at 6pm sharp. And be sure to park around back.

We showed up and entered in the back door. There in kitchen was the doctor.

Wow.

She was dressed in this Venetian Latex and Lace chemise with long latex thigh boots with six inch heels, black opera gloves, that riding crop and a large lace mask in her hand. She pointed to the table that had several piles of clothes on it.

"My pets, tonight we are celebrating. Well, I am celebrating, and since you have been sooooooo good for your Lady you will have some fun too. You will all change into your uniforms, and then you will prepare my house for the entertainment this evening. Change and then I will give you more orders."

"Yes Milady." We all chorused and started changing. She made us fold our clothes neatly like we were little kids and we got dressed. That didn't take long. Every one of the girls had a very skimpy French Maid costume, even skimpier than the ones I had my teachers wear. And me? The doc had me wear one of those Chippendale's waiter get ups; you know the type; tight black leather pants and shoes, black bow tie, no shirt. My bow tie was attached to a collar as well.

I could tell everyone was pretty pissed by this. I know I was. Voice in my head kept going "You lost the bet, you owe her so pay up" and I did, but I had some serious anger and resentment going on internally.

The doc smiled as we finished and she handed each of us a mask and told us to put it on. We did and she really smiled at that. "Oh wonderful. A whole staff of pets! Now my pets, tonight we are celebrating my success. I enslaved your master because he didn't think things through and now I have a full-proof way of making money. Enough money I can finally enjoy my life as I should. A superior woman like me should not have to work so hard to simply have a decent life."

The doc led us into a room and had me stand there holding her wine decanter. I had to pour her wine for her. She laughed at me and said "Cupbearer was a very important position in the old world. You should feel honored." Then she pointed at Nina and Amy. "You two, you will now perform for me. You will enjoy each other's bodies for my pleasure."

Amy bowed her head, but Nina looked at me. The doc snapped her crop against her thigh and said in a cold voice "You obey ME. I own your master so I own you!" I gave Nina a very slight nod and she bowed her head and said "Yes Milady." I made a note of that. Even though I had told her the doc was the boss now, she still considered me to be in charge. That might have to do with the debt obligation as regardless of my orders, she still owed me.

I wondered if that might be something transferable. If that was the case, things could get pretty interesting. That is if I could get out from under the doc's thumb.

Meanwhile I got to watch Amy and Nina. They started with some nice gentle kissing and caressing. Nina was the smarter one and also in my opinion the more outgoing and aggressive of the two and that was from even before my bets had changed her mentality. It wasn't the case now. Maybe it was due to the fact that Nina was reluctant and had not been under the doc's influence like Amy had, but Amy certainly took the lead.

Amy let her hands start to caress Nina's tits through the very sheer silk fabric and I could see Nina flushing and her breath quickening. Nina tried to raise her hands but Amy gently pushed them down and kissed her deeply on the lips. She then moved down the neck and began to trace a fingernail down Nina's cleavage while her other hand looped around her neck and pulled her in close. Amy slowly turned Nina around and nuzzled her neck from behind and let her other hand play with Nina's nipples.

Amy gave a quick tug and Nina's tits popped free. Nina's breath caught at the quick motion and then she sucked a deep breath as Nina's fingers eased down her belly and under her panties. I could see Amy's fingers exploring while Nina's eyes got bigger. Amy giggled after a bit and nibbled on Nina's ear.

The doc chimed in. "Nina, this is why I chose Amy for my partner. You are always trying to be in charge. I understand it given your background, but sometimes pet, you must let go. Let go now, let Amy take full charge and stop trying to think."

Nina gave me another look and the doc smacked her crop down hard. "ENOUGH! I own you! Not this worthless boytoy! Amy! Strap on!"

Amy stopped working her fingers and nodded. Nina was swaying on her legs a bit (Amy's fingers can do some great work) as Amy left the room. The doc had Nina fixed with a nasty stare and I gulped as Amy came back in wearing a rather large black strap on. Nina's eyes got big, but she had figured out not to look my direction.

Amy smiled sadly at Nina. "Sorry Nina. Now please bend over."

Nina looked at the doc this time and slowly bent over and grabbed her ankles. Amy faced the doc and with a fairly neutral expression positioned herself behind Nina. Doc nodded and Amy eased the strap on into Nina.

Nina gasped and sucked her breath as Amy pushed it all the way in and then moaned as it eased out. Amy did it slowly and without a good rhythm and I could tell it was frustrating Nina a lot. The doc smirked and said "Yes, that is it. Punish the pet, just like I did to you that first night."

Amy nodded and kept at it. Nina grunted and tried to get into a better pace, but Amy kept messing with her. Nina got really frustrated but could only grunt and look at the doc with pleading eyes. Finally after about ten minutes of this the doc nodded and Amy fell into a steady beat. Nina reacted quickly and was soon panting as Amy gave it to her.

I was watching, but careful to make sure that I kept the doc's wine glass filled as she sipped and smiled at the show. After a bit she said "Nina, I want to hear you beg."

Nina clamped her eyes shut hard and nodded. She began to beg. "Please, fuck me harder! Please, pound me faster Amy! Come on! Please! Make me cum!" Nina whined out. I couldn't tell if she was faking it or not, but it was pretty convincing. Nina soon began to gasp and twitch.

Amy was sweating heavily now and appeared to be nearly out of breath. She looked pretty hot actually, her skin was slick with sweat and her hair was matted. She looked at the doc with a look that said "Please let me end this" and the doc laughed.

"Very well pet. Finish her."

With that Amy leaned over onto Nina's back and shoved the dildo all the way in and Nina's eyes bugged. She let out a gurgling gasp and then her whole body convulsed. Amy began to shudder too and then they both cried out together. Nina eyes rolled up and she fell to her knees and Amy tumbled down on her. They both lay there gasping for air and the doc clapped.

"Well done Amy. I see you remember what I taught you. Nina, I am not done with you yet. Stand and go over to the archway. Teddy, chain her."

"Yes Milady." We chorused. Nina had a dejected look as she went over and stood still. I looked at the archway that led into the dining room and saw it had two eyebolts bolted into the walls up near the top. On a chair next to the archway were two manacles and chains. I looked at Nina who simply presented her arms. I chained her and the doc walked up.

She was carrying a cat-o-nine tails and slapped it in her hand. Nina twitched at that and the doc laughed. "You need to learn you place pet. You belong to ME now. Count the lashes."

SMACK!

Nina yelped, but was able to get out a startled "ONE!"

The doc smiled and gave her another one.

SMACK!

"TWO!"

The bitch started talking to Nina like I wasn't even there. "Learn your place pet. You are mine forever now. Teddy will play with you and win and I will remake you into a bimbo maid. Or maybe a flower child who runs around barefoot in my yard keeping my flowers. Or maybe a simple secretary. You will never use your mind again when I am done with you. You. Will. Be. Mine."

All the while she whipped Nina and Nina counted out the lashes. The doc stopped at twenty and Nina was crying and sagging in her chains. The doc turned on her heel and strutted back into the living room and finished her wine.

I rushed up and then noticed it was empty. "Milady, I must refill the wine." I said bracing for a wack to the nuts. But she was putting a cigarette into one of those long holders. She merely nodded and lit it. She took a deep puff and said "Go, quickly."

I hurried to the kitchen and started looking for the wine. I found what I thought was the bottle but it was unlabeled and empty. I started digging around quickly and found a case of bottles like it in the pantry. I pulled one out and started to refill the decanter when I noted something. At the bottom of the label was a small print that said "Non-Alcoholic".

I thought for a moment. That was a bit odd. Why the hell would the doc be drinking non-alcoholic wine? I always thought the taste was ass for that stuff. I made a note that this might be worth some looking into and then hurried back.

I got back and walked in on quite a show. Nina was hanging in her chains still; Amy was behind the doc fanning her. The doc had her legs spread and Amber was down between them licking away. Jessica was standing there legs spread and naked except for her heels and stockings. Her eyes seemed to be very glassy and the doc held up her glass.

I poured and the doc gave me instructions. "Teddy, you will, oh how lovely pet, just like that, lay on the floor. MMMMmmmmmm, ssssssss, nice Amber. You will eat out Jessica while she blows you. Make her cum and make her scream. If you can that is. She seemed a bit resistant so I gave her some medicine to relax her."

I looked over and saw a needle. I barely kept my face smooth at that and simply said "Yes Milady."

That fucking bitch was going to get it, so help me.

I lay down and Jessica lowered her pussy down onto my face. Her breathing was slow and relaxed and her eyes were glassy and completely empty of any thought. I gave her pussy a nice slow lick and didn't even get a twitch. "Uh oh. I wonder what the doc has in mind for me if I don't get her howling?" I thought.

Then I felt my cock get enveloped by Jessica's lips and felt her tongue swirl around it. It felt great, but there was no passion in it. It was, well, robotic if you can believe it. And a regular pace. I could have set a clock to Jessica's blowjob. Up, down, up slow with a swirl, down with a hum, off and lick up, lick down, repeat.

I'm not going to complain, a blowjob from Jessica is always nice, even when drugged into a mindless robot. But I was working overtime on her clit. I started by my usually successful snake lick where I tease the clit with short little licks and touches with my tongue. That usually gets them hot and wet.

Not this time though. Jessica just kept right on sucking away and I couldn't feel any flushing, heat, or even hear her breath catch. I moved on into speed and began to work the clit back and forth and up and down at a quickening pace. That got a bit of reaction in that Jessica's pussy started to moisten up and I felt her pulse quicken slightly.

I pulled her ass down onto my face a bit and then decided to try adding some fingers. I eased my index finger into her pussy while I worked her clit and her kegal muscles tightened down nicely as I pulled my finger out. I also heard her breath catch just a bit. I eased my fingers back into her and then out in a nice steady rhythm and I could feel her pulse start to quicken and her breath speed up.