Chapter 5

“Oh God, Mr. Longfellow! Oh, please let me be your fuck whore! Please, I’ll do anything you want, be anything you want me to be! I promise! Please, please let me be your whore. Show me what to do and I’ll do it! I will be a good whore for you ... I will make you feel so good! Please!”

She seemed very sincere about it and I was impressed with her enthusiasm!

“Be careful about throwing that word ‘anything’ around too liberally, my pretty – anything covers a lot of ground!” I cautioned her.

“I mean it, Mr. Longfellow. Yes, I do have a reputation around here for being wild in bed, I suppose, but it’s only because I love sex – any kind of sex. Ever since my first kiss, I knew I wanted to be with boys. I have kissed and had sex with girls a couple of times and it was nice, but I love cocks and what a guy can do to me and for me. So when I say I will do anything, I do mean it. I want to be your whore, Mr. Longfellow, and I will do whatever it takes to be a good whore for you.”

“I see. Well, it’s obvious that you are no virgin and I’m fairly certain you are at least familiar with the concept of a blowjob, although I haven’t given you a chance yet to show me your skills. What I am less certain of is your experience with anal sex. Any whore of mine will have to offer up all three of her holes to me whenever I want to use them. So have you ever been assfucked, Heather?”

“No, I asked a couple of the guys I was dating if they would take my anal cherry, but neither of them wanted to – they didn’t want to get their dicks dirty or something. I don’t know. I have put things up my ass to see how it felt – carrots and a small cucumber once – but I’ve never had a cock up there. Are you going to fuck me up the ass, Mr. Longfellow?”

“Maybe eventually, if you work out as a good whore. But before we get into any of that, I think a good spanking will reset your mind to be more open to my authority.” I opened the drawer of my desk and pulled out a short wooden paddle shaped like a ping pong paddle only thicker and heavier.

“A SPANKING! Oh, please, Mr. Longfellow! Please, not a spanking! Please!”

“Now now, Heather, you know you have been to my office many times. Last year you almost had your own seat here. And this year you are starting right back up with the same regularity.”

“Yes, but neither of the other girls got a spanking!”

“Are you not older than the other two? And from what I have been told by the faculty and other students, you seem to be the ringleader of The Bad Girls Club, isn’t that about right? Don’t the girls do what you say even though it’s wrong, just to be part of your little group?”

“Yeah, but I don’t make them do it. They do it on their own.”

“To be part of the Bad Girls. But as the leader, and the oldest, you should know what you three do is wrong. So you are more or less responsible. If I told you it was okay to cut class and go to the mall and you got caught, would you not tell the security officer I said it was okay?”

“Yeah, I suppose...”

“And that would make me responsible.” Heather knew she had lost this argument and just stood there not saying anything.

I took her silence as acquiescence and moved over to the leather sofa, taking the paddle with me. I sat in the middle of the sofa leaving plenty of room on either side of me. “Come over here Heather,” I said, patting my lap.

“Please, Mr. Longfellow! Please, I’ll be good! I promise! Please, Sir!”

“Heather, the sooner we get this over with, the sooner we can start retraining you into the good little whore we both want you to be. Now come on girl, we don’t have all day!”

She slowly approached me, trying to stall for as much time as she could and hoping I would tire or change my mind. I would do neither.

When she got within reach, I quickly snatched her by the arm, and in the blink of an eye, I had her laying prone over my legs, her hips directly over mine, and her panty-clad ass in full view.

“Please, Mr. Longfellow, Please! You don’t have to do this ... I will be good, I swear! Please don’t spank me! Please!”

“Quiet young lady! You entered into this agreement of your own free will without even knowing the other two of your cohorts did. No one forced you to agree to this. You also knew, going in, that you would be doing things that may not be agreeable to you. And it’s not like this spanking is completely undeserved. In fact, you can consider yourself lucky I am even taking the time to spank you. By all rights, I should have thrown the three of you out of my school right from the start! Now be still and let’s get through this with no more whining or backtalk shall we?”

Heather seemed to know not to press the issue anymore. She’d already begged and pleaded and found it did no good – she didn’t want to exacerbate the situation by pissing me off! She lay still over my lap, waiting for the inevitable.

“Now although this is far from the first time we have met over your disobedience, this is the first time that I have brought spanking into it. So I’m not going to be too severe on you this time. Additionally, I may want to use you afterward, and having you more concerned about your flaming ass than the fire in your tight little pussy would not make for a good time for either of us.

“So I am going to start by warming up this errant ass with my hand to get your cheeks a pleasant rosy pink before I bring in the paddle and get down to the business of spanking you.”

Heather let out a small, pathetic whimper at my words. The hand that had been gently caressing her panty-covered ass now raised high above it. I could feel Heather tense up as she waited for that hand to fall on her backside. But I paused and held her in suspense. I waited until she started to relax, thinking perhaps I’d had a change of heart. Just as she was about to turn around and look to see if I was going to spank her or not, I answered her question.

SMACK! I gave her a good solid swat to her ass on the right cheek in the thickest part of the cheek.

“OH!” Heather yelped, squirming to try to lessen the effect of the blow. Instinctively, she put her hand behind her to protect her tender ass. I simply took the arm and moved it up to the small of her back, using it to hold her in place.

SMACK! Another swat to her other cheek. Once again Heather squirmed, a little more vigorously this time.

Then I stepped things up a little and instead of giving her individual swats, I strung together a series of swats covering both cheeks and alternating between them. I didn’t allow for any rest or break between until I had finished ten solid swats. By the time I had administered the ten swats, she was rolling back and forth on my lap, her ass stinging from the effect of my hand.

“Please, Mr. Longfellow! Please, I’ll be good! Please! No more, please!”

“Oh, but that was just the first part, Heather. Now stand up and pull those panties off. This next part will be a bare-ass spanking!”

“Please Mr. Longfellow! I learned my lesson, I swear! Please don’t spank me anymore, Sir!”

“Heather, if I have to remove those panties, I can’t guarantee that you will be able to wear them anymore! Now be a good whore and remove your panties.”

She stood up and reluctantly took off her panties. I pulled her back down on my lap and rubbed her ass a bit. It had taken on a slight pinking, but I knew I could do better.

Without any warning, I started back up, giving her six good swats on her bare ass. Heather screeched as the sting hit her and she struggled on my lap. But she was no match for me. I had her arm behind her back, her legs flailing helplessly against the sofa, and her ass presented to me perfectly.

But then I threw in something she hadn’t anticipated. After the six swats, I rubbed her flaming ass, letting my fingers “accidentally” trail down between her legs. I rubbed her pussy as I caressed her ass and she responded almost without thinking. Her mind was focused on her searing ass when all of a sudden pleasure found its way to her brain!

At first, she didn’t know what to make of this new sensation – she wasn’t sure what she had felt. It wasn’t the burning of her ass but what was it? Then it dawned on her and she gave a little moan.

“Mr. Longfellow...”

“You like that do you? I can tell you do, Heather, your pussy is getting wet!”

“Oooh yesss...”

She opened her legs wider to let me play more easily. I rubbed her dampening pussy without going in, just fingering her lips and rubbing her slit and the little button of her clit. Her hips raised up to meet my fingers thrusting her ass in the air and welcoming my hand between her legs. That was my cue.

SMACK! SMACK! I gave her two more quick swats on her ass. Heather squealed in surprise and pain and slammed her ass back down on my lap. I smiled to myself, then began rubbing her ass again. This time Heather was more hesitant to get into my fingering her, but persistence and a horny pussy won out and after a minute or two, she was back enjoying my play. I pulled my hand away for a second and she instantly went back to spanking mode ... but I didn’t spank her this time. Instead, I went back to playing with her pussy and clit and she responded quickly.

As she cooed and moaned and whimpered her delight in what I was doing, her hips began grinding and she pushed back against my hand. I knew what she wanted me to do; she wanted me to push all the way into her and fingerfuck her. She was very horny and aroused and she wanted me to make her cum.

But I wasn’t ready for that just yet. She wasn’t ready yet. I wanted her desperate to cum. I wanted her so desperate to cum she was nearly in tears. I wanted her to beg and plead and promise me the moon. I wanted her to think she would die if I didn’t give her an orgasm!

“Somebody must be pretty horny, judging by the way you are squirming and wriggling on my lap! Are you horny, whore?”

“Y-yes, sir.”

I smiled as Heather tried very hard to maintain her composure. I knew that she was struggling to keep from showing just how badly she wanted to cum. And I almost admired her willpower. But willpower alone would not save her from my tormenting. Despite her valiant efforts, I wanted her to crumble. I wanted her willpower to fail her. I wanted her to come to me for relief ... and I was going to make sure she did!

“Yes, you must be very horny ... your tight little whore pussy is leaking like a sieve! I’ll bet you have been going crazy listening to what Kim and Holly have told you about their visits ... and wondering if I was going to do the same to you! Would you like me to show you what I did for Kim?”

“Please, Sir! Please, I am horny ... I am your horny little whore! Please show me what you did to Kim! Please!”

“I may as well, you’ve soaked my pants clear through with your slobbering pussy!” I stood her on her feet then stood myself. She looked at the mess she made of my slacks and then noticed the large bulge where she had just been laying over my lap.

“Can I ... can I see it?”

“If you kneel on the floor like a good slut, I will let you see it.”

Heather instantly dropped to her knees in front of me, waiting for whatever was next. She didn’t have to wait long. I kicked off my slip-on shoes “Now take off my pants, but only my pants, understand?”