The Bet 36

So, I get into trouble in school. What kid doesn't? I'm 18, about to graduate, so what's the big deal. How am I gonna learn if I don't make mistakes?

Well, at least argument works on Daddy...

I got caught after school today in one of the storage rooms with two of the guys from the football team. They literally had their pants down. I was jerking off the one and sucking off the other. I lost a bet and had to pay up, right? Well, one of the custodians came in and caught us. He didn't wait for an explanation or an offer to do the same for him. He just dragged us all down to the principal's office.

"Shit!" I was thinking. I don't need this kind of trouble. I may be a trouble-maker, but I do have plans to go to college. My grades are good and I don't usually get into that much trouble.

So, down to the office we go. The guys were almost crapping their pants. Not that any man would give them a hard time about what they were receiving...I do have to say that I am worth looking at. I had my shirt unbuttoned and my bra pushed up over my 36Cs as I was squatting on the floor with one dick in my mouth and another in my left hand. My uniform skirt was riding up, obviously, so my red, lace thong (definitely not part of the uniform) and the wet spot barely covering my pussy was exposed. I'm sure the custodian got an eyeful. *wink*

We were all decently covered while the custodian (whose name I totally forgot) went in to see Mr. Baines, the principal. The office was empty at this point. It was already after 4 and even the after-school clubs and sports were winding down for the day. I couldn't imagine sitting there with the secretaries staring at me. I'd be labeled the slut and the boys I was with would get nothing more than a smirk...they're football players, after all. This sort of behavior is expected from them, right?

I did feel kinda bad, though. They had both been really excited and neither of them were finished when we were so rudely interrupted.

So, after a couple of minutes, Mr. Baines sticks his head out of his door. He looked at all three of us slowly, in that calculated way that teachers just know is going to make any student squirm. Well, he called both knuckleheads in first and left me sitting out there, alone. And the custodian never came out.

In this day and age when everyone is so worried about appearances, I did wonder why they would take the guys in first and leave me alone in the lobby, waiting to be seen and punished by myself. There should be someone else in the office on my side, right? I'm a girl and I could always claim sexual harassment. But I knew I never would do that. Like I said, I'm a trouble maker and I'm always looking for a new adventure. I was curious to see how this was all going to pan out.

After about five minutes, the football players come out, looking as if they had been castrated, cut from the team, or sent to Siberia. They barely looked at me as they grabbed their bags and ran out.

"Well, that's one bet I probably won't have to pay in full," I thought.

Mr. Baines came to the door and told me that it was my turn to step into his office.

I have to admit, I was a little nervous. I worried that he would call my mom. Both of my parents take an interest in my life, but Daddy was going to be much easier to handle in this situation. I knew that for a fact.

So I walked in and was told to sit down. It was one of those cheap, vinyl-covered institutional chairs with metal arms that can be found in any school office or break-room. It was a little cold, too, because my skirt rode up a bit in the back as I sat. I tried to look as innocent as possible, in my little school uniform, buttoned-up white blouse (never mind the red of my bra showing through the light fabric), sensible saddle shoes, and white socks.

"So, Delaney, tell me what happened? Did they force you?" asked Mr. Baines. There was something in the way he looked when he asked that made me think for a second before I answered. I could have taken the "poor, innocent, girl" who was taken advantage of...but somehow I knew Mr. Baines wouldn't buy it. I opted to tell the truth.

"I lost a bet," I said. "I always pay my bets. I'm not a tease."

I looked him straight in the eye as I said this, and I opened my legs slightly. I knew that would make my skirt rise up a little bit, and frankly, I wanted my pussy to breathe. I was wet and horny and this little interview could go one of two ways. Either way, I needed a little air.

I was aware of the custodian little off to the side and a little behind me. He was staring me down and taking in every word. Maybe he was regretting not giving me a chance to pay him off. Served him right. He saw what he could have had.

"So," said Mr. Baines, "you are perfectly aware of what you were doing?"

"Absolutely," I said. "I was aware and I was enjoying myself." With this, I threw a leg over the arm of my chair. This caused the skirt to ride up and show the tiniest hint of red lace. I leaned back in my seat and smiled. What was he going to do? He was either going to yell at me, threaten to call home, and give out some sort of punishment, or he was going to demand a blowjob himself. It wasn't much of a gamble...I was pretty sure I would get off with a warning and a demand for at least a handjob. Maybe I was a little too sure of myself, though. I didn't expect what came next.

"Stand up and come over here," barked Mr. Baines.

Just his tone of voice surprised me, and I jumped to my feet and did exactly what I was told.

"You are aware that we have certain rules at this institution and that those rules are put in place for a reason, don't you Delaney?"

"Yes," I said.

"YOU WILL ANSWER WITH A 'YES SIR' OR A 'YES MR. BAINES' WHEN I ASK YOU A QUESTION!" he yelled. There was actually a vein sticking out of his temple. I have to admit, I was scared.

"Yes, Mr. Baines," I stammered, very softly.

"YES WHAT?" he yelled again.

"Yes, Mr. Baines," I said with more certainty this time. I really had no idea where this was going. I do think that the custodian was smirking and I'll be willing to bet that he had one hell of a hardon at that point, though.

"That's better," Mr. Baines said. "You will lift your skirt up, bare your ass, and lean over my lap."

I was stunned. What did he want me to do? I just stood there, frozen.

"YOU WILL NOT HESITATE WHEN I TELL YOU TO DO SOMETHING! YOU WILL DO IT!"

I just jumped. I had never been ordered around like this. I don't think anyone had ever even raised a voice to me before. I didn't think, but just did as I was told.

I raised my skirt, showing my red, lace thong, and I bent over Mr. Baines' lap. It was not comfortable being there. I had to brace myself with my hands.

His right arm came down over my back and locked me in place while he placed his left hand softly on my ass. He began to caress it.

"Certain girls have to be taught a lesson," he said, almost soothingly. "You can't just wantonly give out what every man wants to take. You have to be more selective with your favors. Otherwise people will know that you're nothing but a slut. Nothing but a filthy WHORE!"

With that, he raised his hand up and brought it down with a hard SMACK right on my right ass cheek.

"OUCH!" I yelped. And I probably jumped. He lightly caressed the spot he had just hit, but he continued to hold me down with the other arm. I couldn't get up. I couldn't move. But, I have to admit, I didn't want to move.

"I know you want to be a good girl," he continued.

SMACK

"I know you want to do what's right"

SMACK

"You just need help learning how to be that good girl."

SMACK

"I know you are a little slut, but you have to be careful who sees that."

SMACK

"Be happy it was Bill here who caught you and not Mrs. O'Keefe or one of the other secretaries." He was right about that. Those old biddies would make my last few weeks before graduation a living hell...and it wouldn't matter if they called my mother or not. She would just hear about it through the gossip grapevine.

SMACK

And so the lecture continued a little while longer. He called me a whore, a slut, a bitch, a tease and told me that what he was doing was only for my own good. He said he didn't get any pleasure out of my punishment, but I knew better. I could feel him get hard while I was sprawled on his lap like that.

I liked what he was doing and I wanted to take it further, so I spread my legs as far as they could go and I began rubbing my now-drenched pussy into his leg. I'm sure my wetness soaked his pants. He didn't stop spanking me and I didn't stop rubbing for a little while.

Eventually, when his arm got tired and when my ass was probably as red as my panties, Mr. Baines did stop and he helped me stand up and gain my balance. He had me hold up my skirt and keep my back to Bill the custodian so that he could evaluate the redness for Mr. Baines.

Still, Bill said nothing, but he must have nodded his approval. Mr. Baines smiled and told me to face Bill. There he was. He was still sitting on the side cabinet, hadn't moved, except to unzip his pants and pull out his hard cock. He was rubbing the shaft up and down in a regular, slow rhythm. I was mesmerized by the site.

I heard a zipper behind me and realized that Mr. Baines was probably setting himself up the same way Bill had.

"Well," I thought to myself, "I started out with boys and I'm going to end up with men. Not a bad way to end the school day."

"Take off your shirt and skirt," Mr. Baines said. I listened. I was beginning to really enjoy his idea of punishment. And all the time I was undressing, I kept my eyes on Bill rubbing his hard cock.

"Go to the other side of the desk and turn around slowly. We want to look at you," said Mr. Baines.

So I did as I was told. I walked around and stood in the middle of the floor, between the desk and the vinyl chair and the coffee table and couch on the other side of it. It wasn't a big office, but there was still plenty of room. I began to turn clockwise. When I had made one full rotation, Mr. Baines told me to take off my bra. All I had on were my thong, knee socks and saddle shoes. I had kept my hair down that day, so it was skimming just past my shoulders. It was auburn brown and framed my face in a pretty way.

I knew the two men in front of me were enjoying the site just by the way they were both stroking their rock hard dicks. Bill was breathing a bit heavy, but he hadn't changed his rhythm. Mr. Baines was also moving slow, but I had a feeling he at least was going to do more than beat off just looking at me.

"Take off your thong then go sit on the couch, facing me, and play with your clit," said Mr. Baines, still in that soothing voice.

I followed his orders. I sat on the couch, half crouching on it, spread my legs, and fingered myself. It felt good and I was dripping. My ass was a bit sore from my spanking, but the cold vinyl of the couch made it feel a little better.

To give the men a better view and to just be more comfortable, I put my feet up on the coffee table and spread my legs a bit more. I was now matching stride with the two men who were jerking off in front of me. I was looking at Mr. Baines, directly in his eyes. I don't think either of us blinked. We just masterbated. The only sound in the room was the slight rustle of their hands on their shafts and the moist sound that my pussy was making as I ran my fingers in and out of my snatch, up and down on my clit, and even into my puckered asshole.

I didn't know whether Mr. Baines was eventually going to fuck me or if he just wanted to get off while watching me. Either way, it felt too good to stop and I was really hoping he wouldn't break the spell he cast with his eyes.

I began to writhe on that couch. My breathing was coming in shorter gasps. I was trying to keep quiet, though I don't know why. Mr. Baines' earlier yelling and then the spanking he gave me were quite loud. Anyone who was around in the hall would have to have heard everything. Still, I was starting to buck onto my hand while trying to stay quiet.

"I'm going to cum," I managed to gasp.

"Good," said Mr. Baines.

I was bucking now. I couldn't have slowed down or stopped if I wanted to. Stroking myself while these two men watched was too much for me. There was only one other person who ever made me do this for him, and he was going to hear about this when I got home. If I didn't get a good fucking in this office, I knew I wouldn't have to wait long once I told Daddy the story. He loved hearing about the boys and men I fucked and sucked. He spanked me too when he thought I had been a slut. Too bad I didn't know that the principal of my school, Mr. Baines, liked little girls earlier. My four years of high school would have been more enjoyable.

I came hard, right there on the vinyl couch in that office. I couldn't hold it in anymore and I moaned so loud I could probably have been heard on the football field. Just thinking of being watched, thinking of my Daddy's excitement later on...just forced that orgasm out of me.

When I was finished and I opened my eyes, Mr. Baines was in front of me. His pants and shoes were gone, and he was unbuttoning his shirt. His cock was still rock hard and pointing right at me. My feet were still propped up on the coffee table and Bill the custodian was still jerking off where he sat, eyes glued to us.

"Suck it," Mr. Baines demanded.

I did as I was told. I ran my tongue over the shaft to get it wet, and then I took him as far as I could into my mouth. As I pumped up and down, I ran my tongue along the head and in the hole. Mr. Baines rocked in and out of my mouth, making his thrusts harder and faster.

"You're a good little cocksucker," he said. "This is part of your punishment. You're going to suck my cock until I tell you to stop, you little slut."

He pulled my hair and dragged my head down so that the tip of his cock hit the back of my throat, making me gag.

"Mmmm. Suck it, bitch!"

I wrapped my arms around his waist, clutching his ass with my fingers, and pushing my fingernails into his flesh. He kept pumping, in and out, enjoying the sounds I made as I gagged. He called me names, told me how much he enjoyed fucking my face, and that this was only the beginning. I would have to serve detention the same way, every day, after school, for the next two weeks. I would have to suck his cock and the cocks of anyone else who was in the office.

"Except for Bill's," Mr. Baines said. "Bill just watches."

The prospect of detention this way made me suck harder. I wanted him to cum. I wanted to swallow everything he could force down my throat. But he suddenly stopped before that could happen.

"Turn around, on your knees, slut," he ordered.

At this, Bill came down from his perch, pants around his ankles and cock still in his hand. He just came closer to get a better view of the show.

I was facing the couch, on my hands and knees, ass in the air, when Mr. Baines rammed his dick into my pussy. I was dripping and his cock was still slippery from me sucking it. He rammed in and out, smacking my ass while he pumped, riding me like some wild animal. I came again, hard, on his cock. All the while he was calling me names, telling me what a cock-sucking whore I was, teaching me a lesson about who deserves me as their slut.

But just like when I was sucking on his dick, he stopped abruptly, and pulled out. Was he going to jack off on me?

I didn't have to wait long to find out what was going to happen next. He fingered my pussy, and then shoved his lubed-up digits into my asshole.

"Every slut loves to be ass-fucked," said Mr. Baines, as he rammed his rod into my tight little hole.

Now I really screamed. I'd been fucked in the ass plenty of times, but never so roughly. I was loving it, but it hurt. I began to rock back into him, meeting every thrust with one of my own. I knew he was close. Even Bill, standing above us, was beginning to show signs that he might cum soon.

Both men were grunting and pumping hard – Mr. Baines in and out of my ass and Bill in and out of his hand.

When he exploded, I could feel Mr. Baines' cum in me, all warm, filling up my ass. That feeling always makes me cum, and this time was no exception. I had been meeting him, every hard thrust with one of my own. He collapsed on top of me when he was finished, while I was still cumming...and Bill was done soon after that. He shot his load onto my back, getting some in my hair and some on Mr. Baines.

We stayed like that for what must have been several minutes. We were all trying to catch our breath, panting hard.

Bill moved first. He pulled a roll of paper towels out from under the table where the coffee pot was and proceeded to wipe of Mr. Baines and then me. When he was finished he began to dress while Mr. Baines and I pulled apart.

While Mr. Baines too began to dress, I stood there, still in my socks and shoes, waiting to hear what would happen next. Mr. Baines looked at me, smiled, and told me I was a good slut and that detention was done for the day.

"I expect you back here at 4 tomorrow," he said with a warning look.

I looked down, clasped my hands in front of me, and said, "Yes Mr. Baines."

"You may get dressed and go." And I was dismissed.

As I walked to the student parking lot toward my car, I could feel myself getting wet again. I knew I was late getting home. I knew my mother would be out and that Daddy would be mad at me. I couldn't wait to tell him about how I had gotten into trouble at school and I wondered what he would think about my detention!