Wanna Bet? Ch. 02

We had about three weeks left in the school year at that point, and I got busy. I tried simple things, but soon figured out something was off. I would try simple bets, but with the wager as something someone would not normally do unless under a bit of duress. Something like sing a song out loud at lunch, or take off their shoes in class, or equally "high-school Senior Goofing off during last weeks of school" stuff. And I had zero luck with any of it.

It was actually nearly getting my ass severely beat that helped me figure it out. I made a bet with one of the cheerleaders for the wrestling team (Shanna was her name) to do what I had written down on a piece of paper if she lost a hand of in-between. Stupid game, but I found it was the easiest to get girls to play. She played, she lost, she read the paper and she got mad.

Turns out that I fucked up and put the wrong paper down. I had a couple of "serious" papers to use once I had figured out what I had done, and this one said "strip naked and dance" instead of "Sing Achy-Breaky Heart at lunch".

Shanna's boyfriend was an All-State Wrestler in the 189 pound category. And she sicced him on my ass faster than you could say "Oh shit." He found me in the hall by the gym, a nice and isolated spot that I try to avoid due to me being a bit more on the nerd side than the jock side. He shoved me up against the wall, looked around, smiled and said "There is no one in the world that could be in anywhere near as much trouble as you right now."

And because my mouth was not connecting to my brain I blurted out "Wanna bet?"

I was looking him in the eyes and saw that little flash or spark that Ms. Roberts had when we made that bet and he froze for just a second. Then he said "Go on."

I blinked and as he tightened his grip I started talking. "Okay, I know one person in this school who would be in a LOT more trouble than me IF a nasty fact got out. I'm talking lost job, ruined career, and utter humiliation. A teacher. She fooled around with a student, and I do mean in a major way. Absolute fantasy stuff, no lies."

The guy looked at me, but he didn't pound me or tighten up anymore and after a bit he said "And?"

I gulped. "If you want me to continue, we need to set the wager. If I win, and you agree this teacher is in more potential hot water than me, then you let me go. We both tell your girlfriend you gave me some gut punches and a nasty warning and we all go on our merry ways. Trust me I will not go near her ever again. Also, since this is just between us, we keep it quiet. No one else knows, got it?"

"Okay and I win the bet?"

"You can pound me until you are done and I will take it and not say a single word."

The guy nodded and said yes. He dropped me and I pulled out my phone.

While banging the hell out of Lisa I had taken a couple of snapshots. I'm not a perv, but hell, I wanted some proof that this crazy assed day happened and so I took some shots and then hid them on my phone. I got a great shot of Lisa bent over my bed with her ass up in the air, legs and heels showing, with her looking over her shoulder with the Maid Hat on and I showed that to the jock.

He gaped for about 10 seconds and then in a loud whisper said "Oh shit, that's Ms. Roberts! She's posing like a cam model!"

I then showed him another photo that showed a guy plowing her from behind, but no head. I said "This lucky guy is a student here in school. He got Ms. Roberts high and then got her to put out like a bitch in heat. The guy had photos with his face in them, and if they got posted she would be done."

I of course left out I was the guy doing the plowing, or that she had agreed to it. I doubted the guy would believe me anyway, but I was good. He nodded and said "Okay man, you win. She is in more trouble than you if this gets out. Alright, as far as we go this is done. You took a couple of guts blows, and got the idea. Stay away from Shanna though."

"You got it." I replied and I ran like a bat out of hell.

Inside I was bouncing off the wall though. "Wanna Bet?" THAT was the phrase I had to use.

Armed with this I decided to test it again, but on someone I could get a bit more chancy with.

I could hardly wait for school to end and I nearly sprinted down the hall to Ms. Roberts's classroom. And she was there with a friend.

Ms. Roberts was pretty young like I said, just out of grad school. She had some college/grad school friends who also got into teaching and Ms. Megan Jones was one of them. Ms. Jones taught book keeping and accounting, and like Ms. Roberts had the sexy teacher look going. Ms. Jones was a solid black brunette with hair down past her shoulders and a cute pouty face. She had some curves to her too, with a nice slim waist and some nice hips and bust. She was a 34 CC in the chest and had some nice tone. She also tanned and I knew that a lot of the boys wondered if she was fully tanned all over.

"Hi Ms. Roberts, Hi Ms. Jones."

"Good day Mr. Riysom, what brings you here?" Ms. Roberts said.

"Well, I was thinking about getting a letter of recommendation from you. Me being the best of your students and all."

"Best? You are good, but you are not the best." Ms. Roberts said with a prime voice.

"Wanna bet?"

I was watching and sure enough there was a slight flash in her eyes. She froze just for moment and then said "How so?"

"I'll bet that I can score a perfect 100% on my final. If I win, you write me that letter. If I lose, I'll mow your lawn all summer long, for free."

Ms. Jones nodded and turned to Ms. Jones. Ms. Jones looked at her and then at me and said "Lisa, what did you just do? Did you actually make a bet with a student?"

"Yes."

"But why? That's seems a bit inappropriate."

"It's nothing like that." I said. "We did it once before on the Math team, helps makes things a bit more exciting."

Ms. Jones looked a bit surprised. She turned to Lisa and said "I'm surprised at you. This is not something that should be condoned. I seriously think we need to see the principle about this."

I gulped at that and then spoke up. "No need for that. Just a harmless bet. It's mostly for the fun. I think you would really enjoy it."

"I doubt that."

"Wanna Bet? You too Ms. Jones. Wanna bet?"

Both teachers' eyes gave that little flash and I drove on. I pulled out a deck of cards and began to shuffle it. "I'll bet that once you play a hand of poker with me, you will find that gambling is really fun. Addictive even, especially with me. So much so that you just have to gamble with me at least weekly, and just won't be able to say no to a bet with me, for any stake. If you win this bet of course. If I win, then you probably won't like it much and we will just call it good."

I said it that way because I was sure I could lose to these two women. But the reaction was not what expected. Megan snorted and said "Hardly a smart bet. I have no interest in that stake at all." Lisa nodded assent and I thought fast.

"Well, then let's switch it up. If I win, I'm betting you will want to try it again so you can beat me. And that will be fun, and you will find it addictive. Again especially with me. But if you win, you will lose interest and we will call it good."

Both women nodded yes and I had them sit down. I realized that in order to get someone to bet me it required that I had to wager something that meant something to me and to them. I couldn't set up a "Tails I win, heads you lose" bet. I made a mental note of that. I dealt out five cards each for some straight stud and gave a simple rundown of the rules.

I already told you about my skill with cards and I put it to work like I never had before. I started with a pair of nines. I noted that the girls both drew three each which meant normally that they were sitting on a pair each. I dealt them three cards, and then drew three. I am not a believer in luck when it comes to cards and I knew my odds of getting another pair, another three, or something else good and was figuring the odds at me losing.

That day, I was simply lucky. I drew three Kings for a full house. I had a good poker face and I said "Normally we go through a round of betting, but we already set a stake so we can go to laying the cards down right now. Unless you want to up the wager?"

Lisa shook her head no, but Megan had a thoughtful look. "How would we do it? Another favor?"

"Sure. Money is out, so what would you wager?"

"I need my lawn mowed, the person I normally hire moved away. Care to add a summer of free mowing?"

I thought for a moment. "She must have a good hand for this, or she doesn't know enough about poker to know better. But the odds of beating a full house are not good, especially with three Kings, she would have to have three aces to top that and I had discarded one in my hand. Odds in my favor.

"I will accept that. If I win, you will be my servant on every Saturday this summer."

I looked at Lisa and her eyes had opened a bit wider. She looked about ready to speak, but Megan spoke first.

"Done."

Lisa gave her an exasperated look and then looked at her cards. I decided to give her the bad news.

"Ms. Roberts, if you want to stay in, you need to add to the pot or you will fold and lose. That is the rule."

Lisa blinked and gave me a hard stare, but then growled a bit and said "Okay, I'll take your wager of free mowing for a summer. In return I'll provide you free tutoring all summer during your summer school for Calculus."

I grinned. "Hmmmmm, I think if I'm wagering the same for you, you can match Ms. Jones with her bet."

Lisa seemed to struggle and then finally looked at her hand and then sighed. "Okay, done."

"Well, I call."

Lisa laid down her hand and I nodded. "Three Jacks. Not bad."

Megan smiled. "Well, I do believe that a full house wins over that." She laid down three tens over two fives.

I grinned and laid down my hand and said "I win."

I was watching them both when I said won and I saw them both give a little shudder and they both had a small flash in their eyes. Megan looked at the deck and said "You know, that was fun. How about another hand?" Lisa nodded yes and smiled at me.

I grinned even more. "Sure. But we bet favors only. If you want to do actual money, we will have to meet up off school grounds."

They both smiled and I got to work on them hard. I pulled out every ounce of skill I had and these two girls simply got more and more excited the more they played. We stayed at school until nearly 8pm when I finally said enough and headed home.

I had a great night in terms of winning. Enthusiasm was no match for skill and if we had been doing this for money I would have been sending them home broke and with no car. But we had been doing it for favors.

Nasty favors.

I was set up for a long summer of fun. Both Lisa and Megan were now on the hook every day of the summer as my servants. I had even gotten them for this weekend, the whole weekend. And I had won Megan's house. Not as in I now owned it, but as in it was now fully available for my use for anything I wanted. Megan lived about two miles away and had a pool, big privacy fence, and lots of trees and shrubs to block views. I already had a plan laid on for Lisa to pick me up Friday night and we would head over.

I was walking on sunshine the rest of the week. I suppose I could have ensnared the head cheerleader or some other high school hottie, but I had the two of the hottest teachers in school laid on to be my servants so why would I go low?

That Friday, I left my house early and walked along a back street until Lisa pulled up and picked me up. I hopped in and said "Ready for a fun weekend?"

She looked at me and said "Just so we are clear, the "evening" doesn't start until six. We will be there by five, Ms. Jones and myself intend to use this time winning back our summer."

I smiled and said "Sure thing. I recommend you try a different game though. Poker is not your thing."

Lisa said nothing more until we got there. She parked in the garage and I didn't get out until the door was shut. Megan let us inside and she handed Lisa a glass of wine. She looked at me and said "Water over there in the sink."

I snickered and got a glass. I noted the two ladies were already at the kitchen table and had a deck of cards out. Lisa was shuffling. She looked at Megan and then said "The game is Gin, one wager only per hand."

I nodded and we got down to the game. I'll give them credit; they were better at gin by a long shot than poker. We played for an hour, and I agreed to set the stakes at one week of service per hand. But I also laid down some rules such as only the winner would get the week. That way they couldn't team up on me. After an hour, Megan had won back three weeks, and Lisa had won back two. I had won three hands, but had been mostly focused on keeping what I had. I made a mental note to be sure to pick games that I was better at.

At six on the button I laid my cards down and said "Megan, Lisa, clean up this table. Megan, bring me a drink, whiskey and soda please. Lisa, go and make sure that all the drapes and blinds are drawn."

Lisa responded with a "Yes Sir" in that sweet submissive tone from before. Megan replied with a "Yes Mr. Riysom" and I corrected her. I then told her that she also needed to walk sexy when she was my servant. She smiled and said "Yes Sir" and made my drink. Lisa reported back and I stood up.

"Lisa, Megan, take this bag and go change into your uniforms. Then come and join me in the living room."

I went in to the living room and shoved the coffee table out of the way. I pulled the pillows off the couch and noted the carpet was nice and thick. I turned the lights down and started undressing. I was down to my underwear when my servants minced in. I had snuck over to a costume shop and had gotten them matching French Maid outfits, same as before, but with a set of lace white gloves. Both girls were smiled broadly and they came in and said in unison "Sir, we are here to serve you."

I walked up to them and wrapped my arms around them and began to nuzzle their necks. They both giggled and sighed. I took Megan over to where I had the pillow propped up against the couch and said "I am going to take off my underwear and sit down. You will give me the best blow job you can. Lisa, go and bring a bottle of wine and three glasses. You will pour my wine and help me drink it as I enjoy my other servant's attentions."

Lisa gave a little curtsy and said "Yes Sir, right away Sir" and swayed off. Megan led me to the cushions, helped me out of my underwear and then knelt down in front of me. Her lace gloves gently began to rub my cock and she smiled as she eased down. After several long slow strokes, she began to lick the tip and tease my cock. Lisa rejoined us and sat next to me. After a few licks she was sucking me down while I sipped my drink and Lisa ran her fingers over my chest and through my hair.

"Sir, this will be a fun weekend. We are here to serve you and fulfill our bet to you." Lisa cooed in my ear. "So drink up and enjoy your servant's attentions." Lisa began to make out with me while Megan went to town on my cock.

I had jerked off because I wanted to last longer this time and it did help. But not much, Megan was just as good as Lisa had been and soon I spewed into her mouth and heard her gulp it down. She giggled when she was done and then swished some wine around in her mouth. "I don't want Sir to taste himself after all" she said and then eased up next to Lisa and started kissing me.

I was enjoying life but it was this evening I learned another bit about my power. My servants, even under my influence or power, still had independent thought and wills.

Lisa keep pushing drinks on me and when she didn't do it, Megan did. I was soon blitzed out of my mind and sure enough I woke the next morning with a huge hangover and no memory of the night before. I was lying in a heap of pillows on the rug and the girls were nowhere near. I looked around and noted that parts of their costumes were lying around and smelled like sex so I had obviously had a fun time.

But then I noted the card deck.

I thought that was odd and then paled just a bit. "Cards, uh oh. If we were playing cards what did I bet?" I said out loud and heard a laugh from behind me.

"You bet our freedom and lost Sir."

Lisa was standing there with Megan, both carrying trays of food. Megan smiled and nodded. "Yes Sir, that is correct. I can gladly say that after this weekend we are both free and clear of you."

Lisa and Megan swayed in and began to set up my breakfast. Both seemed really happy, not the fake happy Megan and Lisa had been before I ordered them to enjoy the sex (I vaguely remembered doing that after my fifth shot), but legit happy.

After a bit I said "As your Master I order you to tell me what happened. In full detail, leave nothing out."

Lisa replied "Sir, we planned to get you really drunk and play cards with you and win back our lives while your skills were inhibited. We succeeded. After Megan blew you, we got you to drink a lot of liquor and then we fucked each other. We put caffeine pills in your shots so you wouldn't pass out and kept you up but drunk. Then we got you to play cards with us. Poker, then Blackjack, you didn't play well and we won back all our servitude for the summer, plus we won back our dislike of gambling so we don't have any more compulsion to gamble."

I growled at that and Megan spoke up. "We won back pretty much everything and the last thing was your promise to never try and gamble with us again. We won and then you finally passed out. But we screwed up; we didn't bet the rest of this weekend. So you own us until Sunday midnight."

I looked at them and the cards. I picked up the deck and opened my mouth to tell them to sit down and get ready to play poker and found I couldn't. I just couldn't make my mouth open. After a few seconds and flushing red from Megan's and Lisa's giggling I tossed the cards behind me.

"Well, looks like you got me. What time is it?"

"Sir, it's about 1030 Saturday morning." Megan replied.

"Okay, well, I was going to give you some time Sunday to get ready for school, but that's out the window. You two are going to fuck me in every way possible until Sunday midnight. And you will love every second of it fully. You will never have as much fun as this weekend, do you understand?"

They both chorused "Yes Sir" and smiled broadly at me. I ate and then said "Let's head to the bathroom, I need a shower and you two are going to join me."

"Yes Sir." They chorused again and I walked into the bathroom.

Lucky me, it turned out that Megan had an extra large bathtub with a Jacuzzi feature. So I dimmed the lights, had my maids strip down, bring some water (still had a nasty hangover remember), and we had a nice bit of sleazy hot-tub action. I put some bubble bath in and let my hands roam free while the girls rubbed me and let me kiss, lick, and nip their tits. With a couple of orders from me they were both really into it and I brought them to orgasm each twice and I came in the tub at least three times (might have been four, hard to remember ALL the nasty details). After about two hours we eased out of the tub and we drained it.

I looked at Megan and said "You are going to remember this night forever Megan. I wonder if you will ever use this tub again after this." Megan's grin slipped a bit until I told her to remember she was having only a great time and we moved to her bedroom.

There we had a real blow out in terms of sex. I was feeling much better now and after a whole lot of playing around in the tub I was ready for some more direct sex. I shoved Lisa down on the bed and had Megan blow me until I got hard again. Then I mounted Lisa from behind. I started reaming her out doggie style with some gusto. I guess it was a hate fuck. I would get a bit tired and then remember that these two tricky bitches had gotten me drunk and then taken advantage of me and then push into it with a passion.