Wanna Bet? Ch. 01

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A Man discovers a fun ability when gambling.
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Part 1 of the 11 part series

Updated 06/09/2023
Created 09/06/2018
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Moosetales
Moosetales
2,337 Followers

I thought I would try a Told in First Person story so I hope you like it. This one is about gambling. As always, please be polite and useful in your comments.

*****

I probably will never know how I got this power.

As I sit here enjoying Ms. Nelson's, sorry I mean Trixie's, blowjob, my mind still wanders back to senior year of high school and the time when I figured out I had this pretty neat trick. Odd I know. I mean, who thinks about anything other than a great blowjob when you are actually GETTING a great blowjob? Well, I've always been a bit odd, maybe that has something to do with my ability, or talent, or trick, or whatever you want to call it.

My name is Ted and I used to work for a large accounting firm as an accountant. Uh, let me caveat that, I worked as an accountant to support my gambling career until I got good enough at it. I've been great at math for as long as I can remember, and I can do calculations in my head in seconds that nearly everyone else needs a calculator and about thirty minutes to do. I also have a great memory, not photographic, but damn near it. When I was really young, maybe nine, I figured out these things were great in certain games, especially cards. By the time I was twelve I was unbeatable in most card games and was usually pretty damn good at all the rest.

It was my aunt who really got me started gambling. Just after I turned thirteen we had a big family reunion and my aunt played blackjack with all the cousins. She gave us each a dollar's worth of dimes and we played a dime a hand. She was only using one deck of cards so I soon had the game in my pocket. I cleaned her out and most of my cousins besides. I ended up giving everyone back their money so we all ended up with a dollar and everyone was more or less happy (except my Aunt, I kept her money and ended up five bucks ahead). After that, it was all downhill in terms of what I wanted to do.

I started watching the Texas Hold 'em tourneys, and some of the other gambling and card games on TV and rapidly figured out I was on to something. I started my own little gambling ring with the kids in school; craps, poker, blackjack, or any game they wanted to try. Nothing big or bad and I never let a kid get into debt with me or lose too much (learned that the hard way when a kid two classes ahead of me lost $20 on one hand and go so mad he beat me up and took all my money after school).

By the time I was in High School no one in school would play me for any real money, and I ended up getting into some other things like betting on sports (again nothing crazy, just a couple of bucks here and there), or the track (again, no real money, just getting the spread sheet of who was running and see how good I was when I started crunching numbers. Turns out I was really good). I was not stupid and I figured out what I was doing could get me in a big amount of trouble if I really went at it, so it was always small amounts.

Or favors.

And that was when it happened.

I was a senior, and VP of the Math Club. We had a major meet coming up and the President was down with mono. So I had to lead the team to victory, yadda yadda, you get the idea. That meant that I had to lay out some prep work with the Faculty sponsor, Ms. Roberts.

Ms. Lisa Roberts was the Trig and Calc teacher and I had taken her for Trig, Calc, and AP Math (Straight A's thank you). She was very focused and stern and not someone you would take lightly. This was a shame because she was also pretty hot. She was twenty eight at the time, had light brown hair in a bob, and a nice slender body that was in okay shape. Not an hourglass figure, but slim and trim. Her chest was okay, maybe a 32 BB cup, but it fit her body nicely. I knew some guys who took a math class just to look at her, which I thought was weird because we had some hotter teachers who taught easier subjects.

Anyway, I was in the classroom after school laying out my team build and strategy, which was more or less "I take the lead, followed by James, then Tracy, and Susan as the anchor" and not much else. I couldn't see the point of trying to figure out who might fit better in the order since all the questions were random and selected out of a bag on the spot anyway.

"Ms. Roberts, I fully get your focus on this club and how important this is to the school (yeah right, compared to football?), but I really think you are over-thinking this."

She gave me this stern look over her reading glasses (she had those half lens ones like librarians wear on a chain around her neck) and said "Mr. Riysom, I think YOU are not thinking at all. I fully appreciate your comments on this but you should not be the lead, you are much better in the middle where the odds are we will get a statistical question and have Tracy lead."

I kept from rolling my eyes. While I appreciated her recognition of my statistical ability (gambler remember?), the odds of the questions rolling out exactly like she said was so heavily against her that is was essentially (in terms of math) impossible. But she liked Tracy who was heavily into Calculus which was her favorite area to teach. We are all human and I could see that she had some blinders on in terms of favorites.

Now if she had been open about it, I probably would have gone along with it. But she was arguing with me on something I knew I was right on. I also knew I wouldn't win the argument, but the little devil in me decided to make her pay for her inability to put the blinders aside.

"Okay, fine. We will go with your set up. But it's wrong and I can prove it."

"Mr. Riysom, I think you have a bit inflated opinion of your analytical skills."

"Wanna bet?"

I had leaned over and looked her in the eye when I said it. I swear as soon as I said that I saw a very faint flash of light in her Ms. Robert's eyes. She froze for just a split second and then she blinked. She then said "What kind of bet?"

I grinned. "We have three practice runs before the contest. You have the approved test questions and we can get three random kids from detention after school to do the picking. You can judge. If my theory on how random the questions are holds true for all three practice sessions we use my method. If my method is majority we go my way. Opposite for you. Three sessions so we can't have a tie."

Ms. Roberts nodded, but I pushed on. Honestly, I have no idea why I did, but I did.

"One more thing. Let's make this interesting. If I lose I will mow your lawn for free every two weeks this summer."

Ms. Roberts actually lived only two blocks away from my house and I had actually mowed her lawn a couple of times now and then during the summer for some money.

Ms. Roberts smiled at that. "Very well, that makes it a bit more interesting. But what do you get if you win? I don't mow lawns."

I snickered. "True. Um, okay, how about you be my servant for one day?"

Ms. Roberts blinked at that. I held up my hands quickly "Nothing crazy, but in a couple of weeks my parents will be out of town and they are going to want me to clean the house and sort a bunch of stuff prior to college for donation and all of that. Having someone to be my servant for a day would be great."

I figured I may have gone too far, but after a moment Ms. Roberts nodded. "Okay, I can agree to that. One day. IF I lose."

I extended my hand and we shook on it. I didn't really give it much thought for a few days until we had our last round of practice. The contest was Friday; we had practice Monday, Tuesday, and Wednesday. Ms. Roberts got us some kids from detention and we went to it. And just like I figured I was right on the order. I don't know if some otherworld force pushed it, but the questions were literally opposite of what Ms. Roberts had thought on every one. I couldn't have picked them better if I had rigged it and mathematically the odds of that happening where, well, they were so big that I still can't believe it happened.

Ms. Roberts was true to her word though. She accepted defeat gracefully and we reordered the team. And then we won the contest running away (statistics is the way to go I'm telling you) and that really made her day.

So the next week passed pretty quietly and Friday as school let out Ms. Roberts caught me in the hall and said "I'm good to my word. But understand that it might be a bit awkward if I'm seen. I run early in the morning, so I'll be by your house at 6am sharp and won't leave until well after dark."

I nodded and said "I'll leave our garden gate open, just come on in and knock on our patio door."

I got home, said good bye to mom and dad and then unlocked the gate. We lived in a pretty safe area so I had no worries about a break in. Next morning I woke up to the smell of coffee. It was about 6:30 am so I pulled on my beat up jeans and work T-shirt and headed into the kitchen.

I blinked as I saw Ms. Lisa Roberts. She was in a pair of beat up jeans and one of those stretch t-shirts with her hair done up and was sipping coffee from our coffee maker. She looked good.

She nodded to me. "I made some coffee, I hope you don't mind. Shall we get to it?"

I nodded. She stood up and I blurted out "How about you make me breakfast first?"

I inwardly cringed as the words ran out of my mouth. Sometimes my mouth runs away from my brain and I had been thinking about saying that as a joke since she was technically my servant for the day. I braced for a chewing out and my mouth fell open when Ms. Roberts stopped and said "Oh, of course. I did bet you that I would be your servant for a full day. What would you like?"

My normally calculating brain pretty much went offline at that. I stammered a bit and then got out "You don't mind? Making me breakfast?"

"Of course not. I'm your servant for a day. I lost the bet fair and square so I have to pay up."

"I, uh, you, er, (Yeah, real quick with the words, but I'd like to see any of you idiots do better if this happened to you), right. Ahem. Okay, eggs, bacon, and some milk. Hard yoke please, and bring them to me here at the table."

"Right away Ted."

I felt that little devil in me tug at my mind and figured "Well if she's messing with me, time to test it."

"Right away Sir. I'm your Master for today, so it's Sir."

Ms. Roberts didn't even blink. "Of course Sir. My apologies."

I sat down hard and felt my cock harden. Ms. Roberts went to work with gusto and soon had a plate in front of me. She then stood by to my right rear with her hands clasped.

"Uh, you want to sit down?"

"Oh no Sir. I am waiting in case you need anything else."

I ate quickly and once I was finished Ms. Roberts took my plates to the sink and washed them. I stood up and shook my head.

"Cripes, this is nuts. Okay, time to test this little bet."

I looked at Ms. Roberts as she turned around and smiled at me. She had an expectant look on her face. I remember blinking and then shaking my head.

"Let's get to it. Come with me."

I led her to my room and I focused on sorting stuff. I would look at something, say if it was a college, keep but home, or donate and Ms. Roberts would fold it and box it. She worked hard and didn't speak much except to ask if she could use the bathroom once. With her help I was done pretty quickly, what I had figured would have been an all day job was done by just past 11am.

I looked around and nodded.

"Thank you for your help Ms. Roberts. This really went quick."

"My pleasure Sir. I am glad my efforts have met with your approval."

"Uh, why are you talking like that?"

Ms. Roberts face got a puzzled look for a moment. "Um, I'm not sure really. It just seems correct to me. The bet stated I was to be your servant for a day. I guess this is how I think servants talk so I am talking like this. Do you want me to change? You are my Master for the day, so please just command me."

I gulped at that. I remember my cock, which had been pretty solid most of the time working with Ms. Roberts close by in a tight shirt and jeans, hardening even more.

"Hang on Ted. Hang the fuck on. Don't do something you are gonna regret and that will ruin you." I thought.

Then I remembered something that sunk me and it was done.

My parents had a bit of a kink and kept some costumes around for when I was overnight at a friend's house. And I don't mean the Halloween kind either.

And God Damn it, one of them was a French Maid one. A little hat, a black lace bra with white trim, a black pair of panties with white lace trim, white lace apron, a garter belt, black silk stockings, and some six inch black slippers. It even had a feather duster.

And please, don't ask how I found out about the costumes, some things a kid never gets over and seeing his parents doing, well, you get the idea.

Now I had a vision of my Math Teacher dressed up as a real servant and damn it, what eighteen year old senior in high school wouldn't try it? I don't know, but if you ever find one let me know because I damn sure did try it.

"Ahem, Lisa, may I call you Lisa? Good. If you are going to be my servant, the proper term is maid since you are a female. And you are not dressed properly. I want you to go into my parent's room and go to their bathroom. You will shower and clean up. I will lay out clothes for you to wear on the bed. Once you are cleaned up, come out and get dressed. Once done, add makeup as needed, you will understand once you see your clothes. Then you will go to the kitchen and pour me a drink. Whiskey and soda, you will find it under the sink, and use the silver platter. Bring it to me and then I will give you further guidance."

I figured if she was messing with me this would finally fix it. Taking a shower is one thing, but when she saw the clothes that would tip her over the edge (that maid outfit was NOT meant to cover up much at all), never mind the whole alcohol for a minor thing.

I went into the living room and made sure every window was shut and blind drawn. Then I sat down on the big recliner and started flicking though channels. I can honestly say I couldn't find one that interested me and was getting a bit annoyed when I heard a "click-click" behind me and heard Lisa's voice.

"Sir, your drink as requested."

I turned around half expecting to have it tossed in my face and then get grabbed by my dad and beaten within an inch of my life. But what I got instead was something I would have never bet a cent on seeing ever in my life.

Ms. Lisa Roberts, bending forward with a silver tray holding a drink, smiling, dressed in the skimpiest maid lingerie outfit in existence. She had done up her face perfectly and had put her short hair up in a bob which fit the hair piece perfectly. Her tits were just a bit too big for the top and they pressed nicely against it. Her legs looked so smooth that I started to drool.

"Sir? Your drink?"

"Uh, yes, thank you Lisa." I took it and gulped it down in one shot. And then nearly coughed myself to death.

After getting my breath back I focused on Lisa. She was standing by with the tray with a smile on her face like this was the most normal thing on the planet. The booze went straight to my head and I smiled.

"Lisa, you are doing very well as my servant."

"Thank you sir. I am glad I that is so."

"Can you explain to me why you are so, um, accommodating? No offense intended, but as a teacher with me being your student, don't you find this a bit odd? I mean, you just served a minor alcohol and are dressed in a very inappropriate costume for a teacher. Doesn't this bother you in the slightest?"

Lisa pursed her lips for a moment. Then she shook her head. "Sir, I actually have no problem with this at all. My mind is saying I should have one, and that I should be enraged and mad at you for making me wear this outfit. But, how can I put this, it feels correct. I have this urge to obey you because I lost a bet to you and I must, I simply MUST, fulfill my obligation and honor my bet. Everything else simply isn't important."

I was sweating now and my hand was shaking slightly and it made the ice rattle in the glass. "Damn, I don't know how the hell this happened, but if there ever was a sure thing, this is it."

I held up my glass and said "Another round for me Lisa, and get one for yourself."

"Yes Sir, thank you Sir." She replied with a beaming smile and headed off to the kitchen. As she started off I said "Sway your ass Lisa, you are very sexy and I like my servants to show off how sexy they are."

Lisa looked over her shoulder and gave me a smile that would melt steel. And then she swayed the rest of the way into the kitchen with my eyes following her ass every step. She soon came out carrying the tray with two glasses. She set it down and handed me one with a wink. She reached over to get her glass and I took her by the arm.

"Sit on my lap Lisa, snuggle up."

Lisa smiled more and eased onto my lap with her drink. We clinked glasses and I sipped mine and she sipped as well. She coughed a bit and then smiled. "Sorry sir, I normally only drink wine."

My hand began to slide up and down her right leg. "No problem Lisa, take your time. Do you like this? Me running my hand on your leg?"

Lisa smiled. "It is fine Sir; if you enjoy it please continue."

That wasn't the reaction I was looking for. I thought for a minute and then decided to try something else.

"Lisa, you very much enjoy this feeling. You like having your Master enjoy looking at you and touching you. It makes you very happy and turns you on."

Lisa flushed and I noted her breath quickened a bit. She took a larger sip of her drink and smiled at me with a smile that was much warmer and less robotic if you will. "Sir, I do so enjoy your attentions. It makes me VERY happy."

Her left hand began to run up and down my chest slowly and Lisa smiled more. I smiled and then added "You are getting very turned on. You enjoy it so much that you want to give your Master a reward. I nice slow kiss."

Lisa didn't even hesitate. She leaned in and gave me a long, slow kiss that curled my toes. Her left hands circled around my neck and pulled me in close. When we broke I was gasping for air and Lisa looked ready to jump my bones.

"Lisa, we will adjourn to my bedroom. You have made me very happy and now you will have a chance to really make me happy."

"Of course Sir, it is my pleasure to serve you."

Lisa stood and took my drink. I stood and told her to lead the way. She slowly swayed down the hall to my room and then smiled over her shoulder as she opened the door. She moved to the center of my room and stopped, looking over her shoulder at me.

"Sir, I am glad my body pleases you. I insist that you do whatever you desire to me. I am your servant for today and will obey happily in order to fulfill my bet."

I moved up behind her and nuzzled her neck. I was just about as tall as she was, but the heels made it a bit of a stretch. She eased back into my embrace and sighed as I kissed her naked neck. My hands reached around in front and began to gently fondle her tits. She moaned at that and more when my right hand slipped down into her panties. She was nice and wet and even better was shaved completely. My probing fingers found her clit and I gently rubbed it.

Lisa gasped and tensed as I moved my finger around and around while kissing her neck and rubbing her now exposed left tit.

"Very nice Lisa, your body pleases me greatly. Now turn and undress your Master."

Lisa spun and eased up my T-shirt. She folded it and laid it on the floor. Then she undid my belt and then my pants. She smiled as she saw my hard cock pop out of my boxers. She didn't touch it though; she carefully took off my pants and then socks and then boxers, folding each of them.

Honestly, that was a major turn on. This woman was moving slowly and deliberately and her touches and teases were driving me up the wall. I am still surprised that looking back I didn't blow a load right then.

Moosetales
Moosetales
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