The Bad Girls Club, 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.

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?”

“Yes, Sir.”

She unbuckled my belt and unfastened my pants, sliding them down my legs and holding them as I stepped out of them. Then she dutifully picked them up, folding them neatly and setting them on a nearby chair.

She turned back to see a very prominent bulge in my boxers. I like to wear the boxer-brief style of underwear because they are snugger and keep the boys more controlled and not flopping around like plain boxers.


And as Heather was now finding out for herself, I can make quite an “impression” in them when I’m feeling playful! 

I could see by the expression on Heather’s face that she was quite engrossed and curious as to what was making such a prominent lump in my shorts. She sat there staring at it for the longest time as if trying to figure it out.

“Take off my boxers and you can get a better look.” My words startled her from her trance and she looked up at me. Then she looked back at my shorts and began to pull them down slowly… almost as if she wanted to see what was under them, but afraid as well.

“Oh, Mr. Longfellow! Oh, my God, are you kidding me? That’s the biggest cock I have ever seen!”

I could believe that too… Heather and the other girls were used to the young boys here in high school and hadn’t been with real men before. I was their first adult experience. So the cocks that they’d had before couldn’t compare to what I was offering them.

Additionally, I suppose I was larger than the average man so that added to the shock value Heather and the other girls had when they first saw me. 


The size of my cock notwithstanding, she was here for a purpose, and time was slipping away to get it done.

“Okay Heather, let’s see what kind of cocksucker you really are. I’ve heard a lot about your ability to suck a cock, but those are high school cocks, not a man’s cock. Let see how you do when the cocks come a little bigger!”

She looked up at me for a moment and when she realized I was serious and not just making an empty threat, she wrapped one small hand around the base of my cock, her red manicured fingernails contrasting nicely with the pale flesh of my shaft.

I intentionally didn’t give her any further directions or guidance on sucking my cock – I wanted to see what she knew all on her own. Once I saw her technique on sucking a cock, I would know what to add to or modify to suit my own likes and needs.

I wasn’t expecting a whole lot from her. Frankly, seventeen-year-old boys don’t really know a good blow job if they get one, and any girl with her mouth around their cock is a porn queen to them!

But Heather was going to surprise me with her skills. The girl knew her way around a cock! 


“I am quite impressed, Heather. I was expecting an average school girl’s feeble attempt at cocksucking…. like it was her first time. But you seem to know what you are doing – you must have some experience in this field!”

She popped me out of her mouth. “My older brother’s girlfriend showed me how to suck a cock. She even gave me a dildo to practice with. And my brother’s college friends come by from time to time and want me to blow them.” Then she took me back in her mouth and continued working on my appreciative cock.

It was nice to see that some of Heather’s educational opportunities sank in. She may not be a big fan of English Literature, but she was certainly fluent in another language!

As her tongue lolled around the head of my cock and her mouth bobbed up and down the shaft, no interpretations were necessary. The meaning was clear enough… she was really trying hard to win that whore position!

While Heather’s blowjob skills would need some work, she had the basics down and I did have to give her credit for her enthusiasm. I let her work on my cock, guiding her in the rate and rhythm that worked best for me.

I was already as hard as steel, so she didn’t have to worry about that. I didn’t let her know, but I had been looking forward to having her in my office almost as much as she looked forward to coming!


After a few minutes of sucking, I pulled her off me and stood her on her feet. I took her by the arm and pulled her over to my desk, bending her over the top and spreading her legs wide.

She turned back to look at me. “W-what are you going to do?”

“Why, I’m going to do just what I called you into my office to do, my dear. I’m going to fuck you until you can’t walk. If you can leave this room under your own power, even crawling, we aren’t done fucking!”

I slowly caressed her upturned ass as I spoke, getting perilously close to her pussy as my hand moved over her soft flesh.

Heather’s eyes got wide as I continued telling her what she was in for.

“I’m going to fuck you until you can’t imagine fucking anyone else. Then you will be my whore and mine alone, understand? Once I have shown you what I can do, all these immature young schoolboys will fade from your thoughts and memories and I will own you – mind and body.”


As if to emphasize my words, my fingers suddenly plunged into her wet slit, sliding easily into her. Heather gasped in shock and tried to stand up, but I pushed her gently back onto the desk and began slowly pumping my fingers in and out, wriggling them around to add fuel to her fire.

“Ohhh God, Mr. Longfellow…” she moaned as she ground her ass back against my fingers, humping my hand and wanting me even deeper inside her drooling slit.

I watched as her hands gripped the opposite edge of my desk so tightly her fingers turned white. I knew she was enjoying what I was doing and I knew she would enjoy the next step even more.

I continued to fingerfuck Heather as her passions consumed her and her need to cum got more desperate. Soon she was nearly dancing as her ass gyrated and humped back at me. She begged and pleaded for me to make her cum almost sobbing her need was so great. 

With the rubbing I had done previously and my fingerfucking her now, her pussy was sopping wet and her juices ran down her legs like she was in the gym showers.

I knew there was no question she was lubricated enough for even my large cock. And so it was time to properly introduce her to it.


Still fingerfucking her, I moved closer between her spread and trembling legs. I took my cock in my free hand and as quick as I removed my fingers from her soaked slit, I plunged my cock into it.

Full-length and in one smooth motion – fast enough to tear a gasp from her lips, but not so fast I couldn’t stop if I went too deep. I knew she wasn’t used to anyone my size so I wasn’t sure if I would bottom out in the young girl’s pussy.

Fortunately, she was able to take me all the way in without discomfort except that she was being stretched more than she’d been opened before.

“OH GOD, MR. LONGFELLOW!” she cried out as her pussy struggled to accept the cock now opening it wide. I didn’t give her a chance to get used to me before I began pumping in and out of the tight wet hole.

She wanted to be my whore and I was going to show her what the job required. With her laying on top of my desk and her legs pinned to the sides by my own body, she couldn’t struggle much and had to lay there taking whatever I wanted to give her. 

I had promised her I would fuck her till she couldn’t even crawl away and I was determined to do just that. I was going to ruin this pretty little thing for any schoolboy at Franklin Heights and make her want no one else but me.


I was going to show her a world of carnal delights she hadn’t even imagined existed. Oh, I had plans for this one… plans for all three of these promiscuous princesses! 

To show my little schoolgirl slut that I was serious and that she was in the big leagues now, I didn’t hold back very much. I knew I couldn’t go totally all out on her – I didn’t want to hurt her and I wanted to use her a lot more so I had to be a little bit reserved… she was still just a teen girl.

But I also wanted her to know that we weren’t going to be “making love” or be a dreamy, romantic, Harlequin Romance couple either. She was to be my whore – a tool I used to relieve my sexual frustrations and fantasies. I didn’t want or need to get tangled up in a romantic relationship.

I knew that in two years these girls would be graduating if they played their cards right and then they would be gone. I also knew that until then I had to keep what we were doing on the down-low.

The last thing I needed was a teen girl with a broken heart and shattered dreams of happily ever after spreading the word of my sexual exploits with them!

And so, with these ideals and goals in mind, I plowed into Heather’s tight, and very wet pussy with all the force and power that I thought she could handle.


And it turned out she was able to handle more than I had initially given her credit for! As I thrust into her, she grunted out her approval of what I was doing but she also asked for more!

“Oh, yeah! Fuck me, Mr. Longfellow! Fuck your dirty whore! Harder! Fuck me harder! I want it all! Use my slutty whore pussy! Use me for your pleasure! Yes! Oh God, yes!”

Where a girl her age learns to talk like a back alley street whore I don’t know, but then I didn’t question her on it, either. I simply gave her what she wanted and fucked her all the harder for it. 

I reached forward and grabbed a huge handful of her blonde tresses (all three girls had long blonde hair which made great fuck handles!). I pulled her back and up by her hair driving my cock deeper into her at the same time.

Her very admirable 32D tits stuck out invitingly from her ribcage so my other hand took advantage of them. I wrapped my arm around her and began to pinch and tug at the sensitive fleshy nub. The hand that had been in her hair then moved down to her pale blonde bush.

She had trimmed it, I learned, in anticipation of our visit after learning what I had done to her cohort Kim. I think she was hoping to receive something similar today when she met me.


Instead, I reached down and began rubbing her clit back and forth in short, rapid strokes as I fucked her. The technique worked like throwing a lit road flare into a pile of dry, dead leaves.

“OH MY GOD! OH, MR. LONGFELLOW, I’M CUUMMMINNGGG!” she screamed. And as quick as that she did just what she said.

Her pussy gushed like flushing a urinal in the men’s restroom as she poured herself out onto the floor and down her legs. Thankfully both of us were undressed or our clothes would have been drenched by her forceful expulsion.

It was a good thing I had her securely in my arms at that moment because I felt her knees give way and instantly I had her full weight as her legs became unable to bear her weight.

I kept rubbing her pussy as I laid her back down on the desktop and continued fucking her through her orgasm.

As her orgasm finally began to subside, my pace slowed down to long, luxurious strokes letting her feel every nuance of my cock.


She moaned pitifully as I withdrew, probably thinking I was done and getting ready to leave like all her previous boyfriends. But then she gasped as I pushed back in to open her tunnel wide again.

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Copyright © 2021 by Master_Jonathan
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Updated: September 11, 2021 — 3:45 pm
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