Note: This story was dynamically reformatted for online reading convenience. >The Bad Girls Club by Master Jonathan Copyright(C) 2021 by Master Jonathan Chapter 5 -Oh God, Mr. Longfellow! Oh, please let me be your fuck whore! Please, I -(TM)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 -(TM)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 -(TM) 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 -(TM)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 -(TM)s obvious that you are no virgin and I -(TM)m fairly certain you are at least familiar with the concept of a blowjob, although I haven -(TM)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 -(TM)t want to get their dicks dirty or something. I don -(TM)t know. I have put things up my ass to see how it felt -" carrots and a small cucumber once -" but I -(TM)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 -(TM)t that about right? Don -(TM)t the girls do what you say even though it -(TM)s wrong, just to be part of your little group? - -Yeah, but I don -(TM)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 -(TM)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 -(TM)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 -(TM)t have to do this ... I will be good, I swear! Please don -(TM)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 -(TM)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 -(TM)s get through this with no more whining or backtalk shall we? - Heather seemed to know not to press the issue anymore. She -(TM)d already begged and pleaded and found it did no good -" she didn -(TM)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 -(TM)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 -(TM)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 -(TM)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 -(TM)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 -(TM)t spank me anymore, Sir! - -Heather, if I have to remove those panties, I can -(TM)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 -(TM)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 -(TM)t know what to make of this new sensation -" she wasn -(TM)t sure what she had felt. It wasn -(TM)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 -(TM)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 -(TM)t ready for that just yet. She wasn -(TM)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 -(TM)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 -(TM)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 -(TM)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 -(TM)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 -(TM)m feeling playful! I could see by the expression on Heather -(TM)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 -(TM)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 -(TM)t been with real men before. I was their first adult experience. So the pubescent cocks that they -(TM)d had before couldn -(TM)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 -(TM)s see what kind of cocksucker you really are. I -(TM)ve heard a lot about your ability to suck a cock, but those are young boy cocks, not a man -(TM)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 -(TM)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 -(TM)t expecting a whole lot from her. Frankly, seventeen-year-old boys don -(TM)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 -(TM)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 -(TM)s girlfriend showed me how to suck a cock. She even gave me a dildo to practice with. And my brother -(TM)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 -(TM)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 -(TM)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 -(TM)t have to worry about that. I didn -(TM)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 -(TM)m going to do just what I called you into my office to do, my dear. I -(TM)m going to fuck you until you can -(TM)t walk. If you can leave this room under your own power, even crawling, we aren -(TM)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 -(TM)s eyes got wide as I continued telling her what she was in for. -I -(TM)m going to fuck you until you can -(TM)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 -(TM)t stop if I went too deep. I knew she wasn -(TM)t used to anyone my size so I wasn -(TM)t sure if I would bottom out in the young girl -(TM)s pussy. Fortunately, she was able to take me all the way in without discomfort except that she was being stretched more than she -(TM)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 -(TM)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 -(TM)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 -(TM)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 -(TM)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 -(TM)t hold back very much. I knew I couldn -(TM)t go totally all out on her -" I didn -(TM)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 young girl. But I also wanted her to know that we weren -(TM)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 -(TM)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 young 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 -(TM)s young, 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 young girl her age learns to talk like a back alley street whore I don -(TM)t know, but then I didn -(TM)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 fuckhandles!). 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 -(TM)M CUUMMMINNGGG! - she screamed. And as quick as that she did just what she said. Her young pussy gushed like flushing a urinal in the men -(TM)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. Chapter 6 -When are your parents expecting you to be home? - I asked when I saw that Heather had regained her breath and the ability to talk in full sentences again. -My parents don -(TM)t care when I come home or even if I come home, - she said. I took note of the sad tone in her voice and stopped fucking her to turn her around. -What do you mean, Heather? - I asked. -My parents don -(TM)t care what I do. They are more concerned with their own lives and being socialites and the life of the party to care about what I am doing. Hell, most of the time I hardly see them except when we have a rare dinner together or something. I don -(TM)t think I have had either of my parents come to my school unless I was in trouble in years! No school functions, no parent-teacher conferences. One of the reasons I don -(TM)t try out for anything is that they wouldn -(TM)t come to them anyway. So why bother? -I pretty much take care of myself. Right now, they are getting ready to go out to one of the clubs they frequent and socialize with their friends and drink. Then Mom will get all liquored up and Dad will have to bring her home and put her to bed. He -(TM)ll probably not be in much better condition, himself. Tomorrow, everyone will have to walk on eggshells because they will both be hungover so bad that dropping a cotton ball will make too much noise! -So I usually find someplace else to be -" either visiting a friend or something. Sometimes I go to the park or the elementary school and just sit on the swings until I think it might be safe to go home. Or I will go to the mall and hang out there for most of the day. - -I had no idea... - -It -(TM)s the reality I have to deal with. I can -(TM)t do anything to change it -" I -(TM)m just glad that we are well-off and I have money to buy myself something to eat or go to the movies or whatever when I want to. Some kids like me don -(TM)t have that luxury. Some kids live on the street without any kind of support. Those are the ones I feel sorry for. Yeah, I may not have Mr. and Mrs. Brady as parents, but at least I don -(TM)t go hungry too much. - I had to agree with her there. I had worked in other schools where kids were less fortunate than Heather. There were kids in this school that didn -(TM)t have what Heather had. Kids with single parents either a mother or a father. Kids who lived in fear because their parents had drug or alcohol problems or were abusive. Having money certainly didn -(TM)t make up for absentee parenting, but it could be a lot worse. I had to admire Heather -(TM)s outlook and acceptance of her situation. That didn -(TM)t mean, however, that I had to accept it. And I determined that if things worked out with our arrangement like I hoped they would, that Heather wouldn -(TM)t have to hang out at the mall or the elementary playground just to pass the time until her parents saw fit to be parents. I had a good-sized house and on the weekends I didn -(TM)t have much going on. It would be nice to spend the day with this sexy thing, giving us a lot more time for play than we can get after school. I would play things cool for a while, but I had hopes that Heather would come to trust me enough to be able to spend time at home with me while her parents were too busy in their own lives to be part of hers. By the time I had absorbed what Heather had told me about her home life and I had formulated a rough plan on how I was going to help her, she was ready to continue the task at hand. Still standing in front of me, although with her head hung in embarrassment of her parents and her living conditions at home, I hooked a finger under her chin and lifted her face. -Heather I am sorry that you have these problems. No kid should have neglectful or abusive parents. Parents should be who you can go to for help not who you have to hide from or avoid. But I am going to try to find a way that I can help. I -(TM)m not sure what that will be but know one thing -" while you are in my school, you matter. To me, you matter. - And to prove my words, I gave her a long, deep, powerful kiss. That kiss pretty much ended any further troubles I would have from her. She kissed me as if she needed me. It wasn -(TM)t a matter anymore that she was horny or that she wanted to be my playtoy. She needed me. She needed someone to show her what it meant to be truly cared about. To be valued, and to be treated as if she was a person instead of an inconvenient nuisance. We kissed like that for a few moments, letting our tongues play together as Heather tried to devour me with her hungry mouth. When she finally had to come up for air, gasping at the power of our kissing, I pushed her back a bit. -Are you ready to continue? - I asked her. She just smiled broadly and hopped up onto my desk, laying back and spread her legs wide in invitation. I moved forward between those long lean legs and looked down at her wet and waiting fuckhole. -You have such a pretty little pussy, Heather. One of the prettiest I -(TM)ve ever seen and I -(TM)ve seen my share. I want you to do me a favor, though. I -(TM)m sure Kim has told you what I did to her pussy the other day ... how I ate her pussy until she couldn -(TM)t take it anymore. I -(TM)m sure she told you how much I love eating a nice juicy peach and yours looks every bit as delicious. But you are my whore now, so I want you to shave that blond bush for me. By our next meeting, I want to see you naked as the day you were born down there. And if you come to me bare, I will show you just what Kim was talking about, okay? - -Yes Sir! - she said enthusiastically. -Good girl. Now spread those lips wide so I have something to aim this cock at! - Heather giggled and reached down with both hands and pulled her pussy lips apart, giving me plenty of wet pink pussy to -aim at -. I pushed the head of my cock slowly into her, watching as she opened to accept it, and then watched as I slowly sank into the velvety interior. -Ohhh Gaaawd... - she moaned, feeling my cock stretch her insides again. I don -(TM)t know how it is for the women I have fucked, but for me, the initial entry, that first opening of her flower with my cock, is one of life -(TM)s greatest pleasures. I just love that pushing into her feeling almost more than when I am balls deep inside her. And I love watching the expression on her face when she finally realizes what she is up against too. That wide-eyed wonder mixed with the I-hope-I-can-take-all-of-it uncertainty just fascinates me. Heather and I continued to fuck hard and fast for another hour. I made her cum two more times before it was my turn. When I was ready I dragged her off the desk and onto the floor on her knees. She dutifully opened her mouth to accept my load and I told her I wanted her to hold it in her mouth until I gave her permission to swallow it. Then I unloaded a massive load into that sweet mouth filling it to overflowing and watching the cum spill over and run down her chin to splatter on her nubile young tits. It was quite a sight and I thoroughly enjoyed it. Then when I was finally spent, she showed me what she had saved and then swallowed it straight away. She then took me back in her mouth sucking me as if she wanted to turn me inside out to get the last precious drops of me. She squeegeed me squeaky clean with her mouth then sat back on her heels with a great smile. I pulled her to her feet and into my arms. Holding her close, she laid her head on my chest and purred softly. I was glad she had enjoyed herself -" it would make the rest of our times together something to look forward to and something she would want to work hard for as well. Even though we both had a good time, I always kept in my mind that this was an arrangement designed to get her to work harder in school so she could graduate. You should probably go to the bathroom and get cleaned up Heather so I can take you home, - I told her after a few moments of bliss. -Yes, Sir. - After looking up and down the hallway to make sure there was no one there, she trotted across the hall to the bathroom and got herself dressed and cleaned up. I got dressed in my office while she was gone and when she got back we went to my car and headed for her house. Heather -(TM)s house was only a few blocks from the school and it didn -(TM)t take too long to get there. As I pulled into her driveway, she turned to me. -Mr. Longfellow, thank you for such a good time, and thank you for what you said. It means a lot that you care about me -" not many people at school do. I really do want to be your schoolgirl whore and I will do the best I can to earn and keep that. And I promise that I will try harder to get along with my teachers and do my schoolwork too. - -Well, if you do, Heather I can promise you many more such meetings in the future and maybe even some weekend tutoring! - I said. -Ooh, that sounds like fun! - Heather said. She leaned over and kissed my cheek. -Thank you again ... for everything. - The next day was Saturday, the weekend, a time for me to forget about school and the problems of being the principal and running the place. I didn -(TM)t have anything special planned -" I rarely do. Instead, I just relish the peace and quiet of a lazy day at home and catching up on some laundry and other household chores I have put off doing during the week. This Saturday would prove to be a little different, though. It was just after lunch and I had put a load of dirty clothes in the washing machine and was getting ready to take a cup of coffee out to the deck and enjoy reading my newspaper when the doorbell rang. I thought at first it was one of the neighbors wanting to borrow something or some salesman trying to get me to buy the latest whatchamacallit. My doorbell rarely rings -" I -(TM)m not exactly on the local social register and I don -(TM)t regularly donate to all the causes and programs out there so when my doorbell rang it surprised me. Curious, I went to the door and opened it. To my great surprise, Holly was standing on my front porch! -Holly! What are you doing here? And on a Saturday? - I asked when the shock of seeing one of my kids from school at my front door. -I -(TM)m sorry to come by like this but I need to talk. Can I come in please? - she asked. -Of course. I -(TM)m sorry, come on in. - I held the door open for her and she stepped inside. Once I closed the door I turned back to her. -I was about to make myself a cup of coffee, would you like something to drink? - -I wouldn -(TM)t mind a soda if you have one. If not, water would be fine, - she said. Holly followed me into the dining room and sat at the table while I went to get our drinks. I found a soda in the refrigerator and made my coffee. I handed her the soda and sat down at the table next to her. -Now what -(TM)s the problem, Holly? What -(TM)s this all about? - I asked. -Please don -(TM)t be mad at me Mr. Longfellow, but I snuck into the office the other day and looked up your address in the school directory. I know I shouldn -(TM)t have, but I couldn -(TM)t find your number in the phone book, - she said. -That -(TM)s because I am not listed there. I get too many calls from parents and teachers mad at me for one thing or another or wanting to talk work when I am supposed to be home enjoying my time away from school. - I said. -Yeah, I -(TM)m sorry to bother you on a Saturday but as I said, this is very important. - -What is Holly? What is so important? - -James -" can I call you James since we aren -(TM)t in school? - she asked. -Yes, James is fine. - -James, I couldn -(TM)t wait until our next time together. Kim told me what you did to her when she saw you Wednesday and Heather told me today how you fucked her yesterday. James, I can -(TM)t stand it -" please, please fuck me like you did them! I know I -(TM)m a virgin, but I want you to take my cherry. I want you to be my first. Please! - she said. Well, you could have knocked me over with a feather! But I could see by the pleading expression on her face she was serious! I took her hands in mine. -Are you sure about this, Holly? Have you thought it over good and long? - I asked. -Oh, James, it -(TM)s all I -(TM)ve BEEN thinking about! It -(TM)s all I -(TM)ve been dreaming about. I can -(TM)t get the idea out of my head. Listening to what Kim said you did to her was bad enough, but then Heather and Kim and I talked on the phone last night after you finished with her and well, I couldn -(TM)t stand it anymore! Please, James, I want to feel what they felt! I want to scream out and I want to cum on your cock. I want you to make a woman out of me and I want you to fuck me till I can -(TM)t walk too! Please, James! Oh God, please take me to that place too! - I looked at Holly closely. I could see the need in her face as plainly as if she wore a Fuck Me t-shirt. I could also see her eyes, those soft, pale blue eyes, were wet with tears. It had taken a lot for her to come here today and bare her soul to beg me to fuck her. I didn -(TM)t know her home situation all that well, but I had a feeling her mother was not the type to let her go out dating just any boy she liked. After all, she was eighteen years old, a junior in high school, and still a virgin! Her mother was obviously quite strict about her dating and maybe doesn -(TM)t want her to get mixed up with the wrong boy and end up getting hurt. I could totally understand her mother -(TM)s concern. While not a parent myself, I couldn -(TM)t help but form an attachment to the kids at school. I was their principal and authority figure sure, but I was also their friend and I made sure that I was never too busy to listen to their problems no matter how big or small. I may not always be in a position to help them with the problem, but I could always listen and offer advice if I had it. And even though I was supposed to be impartial and treat them all equally, it was only natural that I develop some favorites -" and Holly was certainly in that category. I thought about my next move for a couple of moments. The decision was clear -" I had to help Holly. I had already brought her into this even though it was her choice whether to go along with my idea or not. And now she was sitting in front of me, ready and wanting to be a full-fledged member of The Bad Girls and my little -harem - of honeys. My concern wasn -(TM)t if I should help her, it was how I should help her. Finally, I stood up and walked around the table to stand in front of her. Without a word, I held out my hand and she looked up at me and smiled sweetly, placing her small delicate hand in mine. I pulled her to her feet and we walked hand in hand back to my bedroom. My bedroom is at the back of the house down a long hallway and directly across from the master bathroom. When we got to the bedroom door I stopped once more and turned to her. -Are you sure about this Holly? It -(TM)s not too late to turn back you know, - I said. -I -(TM)m sure James. I want this. More than anything, I want this. Please, - she said, looking up at me. I opened the door and we stepped inside. I walked her over to my bedside and I sat down on the edge of the bed pulling my visitor in front of me. Looking her straight in the eyes so she would know I want an honest straightforward answer, I asked her -Now before we get into anything I know you are a virgin but what about birth control? Are you on the pill and have you been taking it regularly even though you haven -(TM)t had sex? - -Yes, James. I have been on the pill since I was sixteen years old. My mom buys them for me and insists that I take them every day. She says she had me when she was too young and not ready for the responsibility of raising a child alone. She doesn -(TM)t want me to have to go through what she went through, and she knows how persuasive boys can be to a teenage girl. She also says she doesn -(TM)t want to raise any more kids. So she makes sure that I take my birth control pill every morning at breakfast. - -She sounds like a very smart woman. Well, as far as I -(TM)m concerned, I am clean -" no STDs or anything to worry about. I am very careful and even more so, now that I have three little playtoys to concern myself with. So far, with both Kim and Heather, I have only cum in their mouths or on them. I have not cum in them. I asked them both before we did anything if they were on the pill and they told me they were. The next time I go to the store, I want to get some condoms just for added protection, but I need to find out if any of you girls are allergic to latex. - -Well, I -(TM)m not ... not that I know of, at least. - -That -(TM)s good to know. Frankly, I don -(TM)t like wearing the damn things -" I lose a lot of the sensation and the fun by having to wear one. But I don -(TM)t know Heather and Kim -(TM)s sexual practices yet and I don -(TM)t want to be spreading whatever they might catch from the guys they hang with. I do want them to start being exclusive to me so I can protect all of you girls from getting anything that might be passed around. But there -(TM)s time for that ... right now I know I have one girl I don -(TM)t have to wonder who she -(TM)s been with! - -Yeah, I -(TM)m fresh as the morning dew! - she said with a giggle. -A temporary condition, I assure you, - I said. Holly let out a small moan at my words. Holly stood there in front of me looking like every man -(TM)s dream girl. With her shoulder-length blonde hair put in pigtails today, her short-sleeve front-tie crop-top, way too short Daisy-dukes, and her chunky heel sandals, she looked sexy and ready to play. She stood there biting her bottom lip as I reached up to the front tie of her top and began slowly undoing the knot. -I-I -(TM)ve never been undressed in front of another guy, - she confessed quietly. -Never? - -Mm-mm, - she said, shaking her head. -The two boys I let do anything she played with me over my clothes. - -Well this is even more of an honor then, - I said with a smile. She returned my smile but cautiously, still worried about what I would think. I got the knot untied and peeled the garment apart. Then I realized why I could see the faint outline of her dark aerola and the bumps caused by her hard nipples -" Holly was not wearing a bra under the semi-sheer crop top! She really had come to play! -Very nice, - I said. Relieved, Holly let out the breath she -(TM)d been holding. I peeled the top the rest of the way off of her letting it fall to the floor behind her. Then I reached up and cupped the firm, full tits in my hands, using my thumbs to rub over and play with the hard crinkled nipples. Holly must have enjoyed this because her eyes closed and she mewled softly as her hands came up to cover mine. -You like my hands on you, Holly? - I asked her. It was a moot point, I knew, but I wanted her to acknowledge it herself. -Oh yess... - -You have a very lovely pair of tits, my dear. I noticed them the first time I saw you. And every time you come to see me in my office. - -You really like them, James? - I didn -(TM)t answer her in words. Instead, I took my hands off her tits and reached behind her ass to pull her closer to me. Then I put my mouth over one hard nipple and sucked it into my mouth trapping it with my teeth lightly while my tongue went to work caressing the meaty morsel. -Ohh God, James... - she moaned, her hands moving up the hold my head and running her fingers through my hair. My own hands went to work squeezing and mauling her tight ass cheeks. She began wriggling her ass as I grabbed large handfuls of her rump and playfully swatted it, the latter causing her to gasp as my hand landed, but then she pushed back for another. I spent several long minutes feasting on Holly -(TM)s tender tits, much to our mutual satisfaction. I alternated back and forth several times to make sure no one went ignored or neglected, either. When I had (temporarily, I assure you) had my fill, I moved on to other delights yet unexplored. Holly may have been younger than most of the women I usually dated and a good deal younger than some, but she was every bit a woman, with a woman -(TM)s body and apparently a woman -(TM)s sexual appetite. Holly knew what she wanted and I was fortunate to be the target of that desire. She was very well proportioned with nice curves in all the right places. She was a beautiful woman and I couldn -(TM)t help but feel my cock twitch, knowing what wonders I was about to partake in. I moved from her tits to working on ridding her of those short Daisy-dukes. Basically, she had taken a pair of old blue jeans and cut the legs off right at crotch level cutting off and sewing up the pockets so they didn -(TM)t show underneath. She had purposely -feathered - the edges of the cut-off legs a bit to serve as trim. I unbuttoned her jeans and zipped down the zipper. I pulled apart the front of her jeans and she wriggled her hips as the garment slipped over her hips and ass. I slid them down her long legs then held her hand as she stepped out of them. Now dressed only in her panties and her shoes, Holly stood there with her hands behind her back looking for my reaction. I looked up and down the eager, nubile form in front of me. I studied it for some time -" not only to take in all its nuances but also to increase her suspense in what I might find. After what had to be an agonizing wait for her, I gave her my results. I reached between her legs and began rubbing her pussy through her panties. -You are a very lovely girl Holly and you have a hot, sexy, amazing body. I am so glad you decided to go along with my plan, I would hate to see you not be able to graduate but also I can see we are going to have a lot of fun in the meantime. I can make the next couple of years at school easier on you academically and certainly a lot more fun. You like having fun don -(TM)t you, my sweet? - -Ohhh ... yesss, - she moaned as she rode the hand in her crotch. -Yes, I -(TM)m sure you do. Sweet, sexy girls like you just love to be touched to be played with. And I know all sorts of games we can play. I am going to enjoy our times together, and I -(TM)ll bet you will enjoy them too. I can do things to you that you can -(TM)t even imagine ... make you feel things your mind can -(TM)t even grasp yet. Would you like me to show you some of them, Holly? - -Oh God, please! Please show me! Please, James, I want you so much! - she whimpered as I sawed back and forth harder now. I moved my thumb up to concentrate rubbing her clit as her panties got more and more soaked. Chapter 7 -You made the right decision coming to me to be your first, Holly. If you -(TM)d gone to one of the other boys at school, they wouldn -(TM)t have appreciated what they were being given ... they would have just taken your cherry in their own bumbling, amateurish way and been done with you, breaking your heart and leaving you crying. But I am not like that. I want to protect you and keep you safe and happy. I know the gift you are about to give me. I appreciate you for the beautiful, wonderful creature you are. And I won -(TM)t just use you and cast you aside, my sweet young beauty. - -Ohhh Jaaamesss... - she said, her knees getting weak both at my words and my actions. -No, my dear, when I am through with you today, I will own you. I will be all you want and all you need. I will take care of you, princess, and I want you to be mine and mine alone. I do not like to share my toys and will not share you. Will you be mine alone, Holly, my sweet? Will you pledge yourself to me alone for as long as we are together? - -Oh, Yes! Yes, James! Oh, I want to belong to you! Oh, please make me your girl! Please! I want to be yours and only yours! Please! - she cried. I stood up and took Holly in my arms. I still continued to play with her pussy, but at the same time, I kissed her. When she kissed me back it was no ordinary kiss. This kiss had true meaning behind it. I have been kissed enough to know the difference between a -thank you - kiss, a -goodnight - kiss, and a kiss that means -I have feelings for you -. This kiss wasn -(TM)t any one of those. This was an -I give myself to you wholly and completely -" I surrender to you - kind of kiss. The kind that makes you know the other party is yours totally. An ownership kiss. Holly was telling me in no uncertain terms that she was mine for the taking. Well, such a gift should not go unclaimed. I turned us both around and gently set her on my bed, laying her back. She automatically spread her legs wide and held her arms out to me, inviting me to partake of the feast before me. But rather than just rush into the act itself as any schoolboy would, I wanted to show her she was something to be savored and enjoyed ... a banquet, not a brunch! So instead, I knelt down on the floor between her spread legs and inhaled her sweet, musky perfume deeply. I licked the large wet spot on her panties to get my first taste of her honey. Then I reached up and began slipping her soiled and soaked panties from her hips and uncovering the treasure that lay beneath. I slid her panties down her legs until they came off and I brought them to my nose to inhale her scent again. She watched me smell her this time and it made her whimper with need. -I will be keeping these as a memento of today -" the day I took possession of you. And whenever you come over you will see them and know you belong to me. - I said. -Really James? You are really gonna keep my panties? Oh God, that is so hot! I -(TM)m glad I wore my good ones then! - she said. I hung the soiled panties on the corner bedpost and turned back to her. She lay there watching my every move and I got closer to her steaming hole, spreading the lips and peeking into the wet pink heaven inside... -OH GOD JAMES! - she squealed as I fastened my mouth over her leaking pussy. My tongue wasted no time in plunging into those dripping pink depths and began its search for every pearl of sweetness it could find. Holly had gotten a brief introduction to what I could do with my mouth the last time when she came to my office that previous Monday. I was sure she remembered the way it made her feel too -" it was probably part of the reason she was here now. But this time I didn -(TM)t have to rush and I didn -(TM)t have to worry about someone coming in and catching us. So I was able to pull out all the stops and show her what I could do! Needless to say, she was completely overwhelmed by the sensations coming from her virgin pussy. Instinctively, Holly reached down to push me away just as she would if I had started tickling her. But I wasn -(TM)t tickling her, I was devouring her. And she wasn -(TM)t going to get rid of me so easily. She writhed and squirmed, thrashing her head around and clawing at the bedsheets. To look at her, you would think she was either possessed or going through some sort of seizure. But I knew what was wrong with her, and I was going to make sure she got the proper -cure - for it! I have always been kind of proud of my cunnilingus skills. I -(TM)m certainly no professional pussy-eater, but I -(TM)ve never had a woman complain that I didn -(TM)t get her off or that she wasn -(TM)t happy with how I ate her. I love the smell, taste, and feel of a woman -(TM)s pussy and I have had a lot of really good times nestled between a happy woman -(TM)s thighs. Now I was nestled between Holly -(TM)s thighs showing her what I had learned. And she was quite impressed with my skills judging from the gasps, cries, and squeals she let out. I knelt there between those pale, creamy thighs happily munching away at her sweet, juicy peach for several minutes, in no particular hurry to stop. I was enjoying driving this young virginal woman to heights of pleasure she had never experienced before. Suddenly, but not unexpectedly, I heard that special sound I had been aiming for. The joyous sound of a woman at her end. -OH FUCK, JAMES! OH GOD, I -(TM)M CUMMING! I -(TM)M CUUUMMMINNGGG! - she screamed. She slammed my head into her crotch and clamped her legs together as if she was trying to snap my head off my shoulders. I was prepared for her as she clamped down on my head I quickly shoved two fingers up inside her curling them around her pubic bone and rapidly fingerfucked her -" adding one more level to her distress and causing her to squeal again in surprise. Holly offered up her juices in abundance ... I don -(TM)t think even she realized how hard she could cum given the proper motivation! Although in reality it only took her a few moments to finish, I -(TM)m sure it felt much, much longer to her. But at last, the spasms and contortions faded and she lay panting and leaking her juices onto my bed. I sat on the bed next to her as she recovered watching her and stroking her sweat-dampened hair. She opened her eyes to see me next to her and smiled weakly. -T-That was ... amazing! - she whispered. -Shhh ... just rest, honey. That was only the beginning. Just an appetizer -" we haven -(TM)t even gotten to the main course yet! - I said, smiling. -Well, I hope the main course is as tasty as the appetizer was! I -(TM)m starving! - she said, continuing with the food references. -Better get in the middle of the bed then, we wouldn -(TM)t want you falling out of bed at a crucial moment! - I said. She moved into the middle of the bed and scooted up a little higher as well. She lay there on the bed watching as I got undressed now. She had yet to see me naked since all we got a chance to do Monday was for me to eat her pussy and make her cum once. So I was curious how she would react when she saw what I brought to the party. And I was sure she had been told I was -huge - by Heather and Kim but huge is a relative term. I wanted her to see what she was up against for herself. I took off my shirt and my pants and stopped at my boxers. I was already fully hard from playing with and eating her so I was quite -prominent - already. I saw her eyes get big just looking at the lump in my shorts! I moved closer to the bed so she could get a better look. I dropped my boxers slowly letting her see an inch at a time. At first, she saw the head of my cock and she was fascinated, staring at the purplish mushroom cap. -Have you ever seen a guy -(TM)s cock before? - -No. I mean I might have seen my father -(TM)s when I was very little. But he left when I was only a year old, and I haven -(TM)t seen any other guys, - she said quietly. -Well, there -(TM)s nothing to be ashamed about Holly. In fact, I think it -(TM)s wonderful that you have saved yourself like this. Most girls your age act as if their virginity is something they need to get rid of as soon as possible -" like a cold or something. They go with the first guy who shows any kind of attention to them and gets that annoying virginity thing out of the way. But that -(TM)s not the way to approach your first time and I am pleased that you have held onto yours. I am also quite honored you want me to be the one you give it to. It is a special thing to be given such a treasure and I want you to know how important this is -" to both of us. - I said. -Thank you, - she said, blushing from the compliment. I finished removing my boxers and Holly looked at my cock with wide-eyed wonder. -Oh my God James! - she gasped. -Heather and Kim said you were enormous, but I had no idea! I don -(TM)t think that thing is going to fit in me! - -Relax, Holly sweetheart, It will fit. Pussies are remarkable things -" they stretch to amazing sizes. Remember babies come out of there and if a baby -(TM)s head and shoulders can come out of that hole, then I can certainly fit in it! - I smiled. -I never thought of it like that. But I -(TM)ve never had anyone -" or anything as big as you in there. - -Don -(TM)t worry sweetheart. I know you are a virgin and I will take it nice and slow and tell you everything I -(TM)m going to do before I do it so you will know what to expect. You trust me, don -(TM)t you? - -Yes, I trust you, James. Thank you for taking it slow with me. - -Of course honey ... I want this to be as special for you as it is for me. I want you to enjoy this -" after all, I do want to do this again, you know! - I said, smiling. With that I climbed into bed and moved into position over her she looked up and I saw the anxiety and uncertainty in her eyes. This was a very big step for her and I would have to treat her like the delicate flower she was. I lowered my mouth to hers and kissed her again. -Now, just relax sweetheart and let me do all the work, you just lie back and enjoy this okay? - She nodded her head. I reached down and took hold of my hard cock. -First I have to lube up my cock a little. You are plenty wet already but I want to make sure I am ready, - I explained. I began rubbing the head of my cock up and down between her slick lips, coating the head with her juices. -How do you like that Holly? - -It feels nice. Thank you for explaining things to me, James. It makes me feel better when I know what you are going to do. - I smiled at her again and rubbed my cock up and down her wet slit until I was sure it was properly lubed then I lowered my hips a bit and ran the length of my shaft between her lips to coat it as well. This caused Holly to moan a bit feeling the velvety skin with its veined surface running up and down her virgin pussy. -Ohh James, that feels really good... - -Oh, it -(TM)s going to get much better here in a bit my dear, - I assured her. After three or four passes, I was satisfied I was ready to go. I drew my hips back until my cock was at her pussy entrance. -Okay, honey, I -(TM)m ready to go. Are you ready? - -Y-yes ... I think so... - she said. I don -(TM)t know whether she was trying to convince me or convince herself of the fact, though. -All right then here we go, nice and slow... - I started to push into her very gently, only a bit at a time. At first, she didn -(TM)t seem to mind it but when my cockhead began spreading her opening I could sense the change in her. -Oh, James! Oh, I feel it! I feel you spreading me ... opening me! - -Yes, just let it happen, sweetheart, you can do it. Just relax and let your pussy accept me, - I coaxed her. By now my cockhead was really opening her and she was beginning to doubt her abilities -Oh God Oh you are so big! Oh, I don -(TM)t know if I can do this! - She began to gather big handfuls of the sheets in her fist and clench them tightly. She wasn -(TM)t trying to move away, but I could feel her moving around under me trying to find a position that would allow me to get in easier. Suddenly there was a pop and she gasped -What was that? - -Take it easy honey, that was just my cockhead slipping into you. I -(TM)ll wait here a second or two to let you get used to me inside you before I proceed. - -I -(TM)m sorry I -(TM)m such a baby about this James, but... - -Shhh, - I told her. -It -(TM)s perfectly all right. This is the first time you -(TM)ve done this and you don -(TM)t know what -(TM)s going on. I understand perfectly. Your mom probably hasn -(TM)t even had -~the talk -(TM) with you has she? - -No, Mom doesn -(TM)t want me to be around boys so she doesn -(TM)t feel she needs to have -~the talk -(TM) about sex with me. I don -(TM)t have anyone to tell me what -(TM)s going on, what I should and shouldn -(TM)t do or feel ... it -(TM)s all very strange. - -I -(TM)m sure it is, Holly. But you don -(TM)t have to worry with me, sweetheart. I will explain things as we go and I will take it as slow or as fast as you need to. I want you to enjoy and understand what is happening. I want you to have fun with this because sex should be enjoyable. It shouldn -(TM)t be scary or confusing. I don -(TM)t have any children myself, I -(TM)ve never been married. But if I did, I would want to talk with them about all this so they knew what was happening to them. - -I appreciate you taking your time with me, James. I -(TM)ll bet you would be a wonderful father. I wish you were my father. You kind of are you know, being principal at school -" you are like all of the kids -(TM) fathers in a way. And for those of us who don -(TM)t have fathers, you are the next closest thing. - -Well thank you, Holly. And yes, I do think of you and all the kids at school as my kids in a way. I want to protect you and keep you from getting into trouble. I want to look out for all of you and if you have a problem, I want to try to help if I can. Now, are you ready to continue? - -Yes. - Holly prepared herself for more, spreading her legs wide and pulling her knees up to give me more access. I began pushing again and my cock slipped another inch or so into her. -Ohh Jaaames ... Ohh, you are stretching me so wide! This feels incredible... - A bit further and I felt her hymen and I stopped. -What did you stop for? Is something wrong? - she asked, raising her head off the pillow. -No, nothing is wrong. I -(TM)ve reached your hymen. It -(TM)s a thin membrane covering your vagina. You -(TM)d call it your cherry. I need to get through it to go further. Now, this might hurt a bit, I won -(TM)t kid you. But once it -(TM)s done, the pain will go away and you will be ... a woman. Are you ready? - Holly grabbed a pillow to bite into and held it close then she nodded. But I had a better idea. I took the pillow from her and set it aside then I laid down on top of her and she put her arms around my neck. -This is such an intimate and important step for you. It should be shared intimately. - I explained. She smiled gratefully. I held her tight and whispered in her ear. -Are you ready? - I felt her head nod and she gripped me in readiness. I thrust my hips forward and I heard her whimper and squeeze my neck tightly. I felt her hymen tear and I moved forward into a place where no one had ever gone before. -I -(TM)m sorry, - I said, holding myself still for a moment. Then I moved forward and pushed deeper into her. I knew it hurt, but I knew that soon the pain would fade to be replaced by a pleasure she had never known. She held me tightly for a couple of minutes but, as I knew it would, the pain began to lessen and her whimpers slowly turned into something more pleasurable. -Ohh, James! Oh God, I feel you moving inside me! Ohh, I feel so full and yet it feels so good! - -I knew you would like it once we got past your cherry. Do you want me to go deeper now? - -Deeper? You can go deeper than this? - she asked incredulously. -Yes, honey, I can go deeper. You have about half of me in you right now. - -HALF? You are only halfway in? Oh God! - she gasped. I chuckled a bit at her reaction. -Well, a little over half maybe but yeah, I still have a ways to go before I -(TM)m fully inside you. - -Oh, God! I -(TM)m already so full... - -Do you want me to stop here, then? - I asked. I don -(TM)t think Holly wanted me to think she was afraid or -chickening out - as the kids put it. So she summoned up her bravery and said. -No, I want to go on. I want to see if I can take it all. I know Heather and Kim took all of you and I want to be able to also. - It was a pride thing -" she wanted to be able to compete with the other girls, fearing I might like them more if they could do more for me. She had to be able to match their abilities even though this was her first time. It was the same with boys. No one wants to be thought of as a wimp or a scaredy-cat, or a weakling. School reputations are on the line here. So I completely understood. -All right then we will keep going. But you let me know if it starts to hurt too much, - I said. I knew she would push herself probably a bit too much this first time, showing me she could handle it, so I kept a watchful eye on her reactions, and the first sign of wincing or pain I would stop. The pain from breaking her hymen had faded by now so that made it easier to judge her tolerance. I pushed in deeper and she moaned as she felt me stretching her wider and further than she -(TM)d ever been stretched before. Holly arched her back as she cried out with unbridled passion. -Yes! Oh God, yes, James! Oh God, it feels so incredibly wonderful! Oh, push deeper! Deeper! I want all of you! I want all of that enormous cock! Ohhh, Yesss! - I will admit she felt pretty damned good herself. I had only been privileged to take one other girl -(TM)s cherry, back when I was with my first girlfriend. She and I were both virgins and neither of us had a clue what we were doing, to be honest -" only sheer animal instinct told us what to do. But we managed, somehow, to enter the world of adulthood on that old blanket on the beach. She moved away with her family after that summer but I never forgot her or how she felt around my young eager and inexperienced cock. Now many years and many women later I was reliving those wonderful days again with Holly. She was every bit as tight as I remembered and I hoped she was enjoying her first time as much as I did back then. I pushed in once again but this time I felt resistance and I knew I had reached the bottom of the young girl -(TM)s well. Correction -" the young woman -(TM)s well, because Holly was most certainly a woman now. Feeling the tip of my cock touch her cervix made me look down and I noticed my cock was almost completely enveloped in Holly -(TM)s tight pussy. Only about an inch remained outside -" a pretty respectable feat for her first-ever cock. -That -(TM)s it, Holly. You have all of my cock, honey. I didn -(TM)t want to tell her there was still more of me to go, so I chose my words carefully. I didn -(TM)t want her to feel bad for not taking me completely in. -I have all of you? Really? Oh, this feels amazing! God, I am so stretched ... so full! - she said. I stayed buried deep inside her and holding her for a few moments until I felt her pussy loosen a little, getting used to my size. She was still tight as a vise, but at least once I started moving inside her she could enjoy it without much discomfort. After a bit, I felt it was safe to start moving in and out and get on with the actual fucking. I raised up so I could see her face, -Are you ready to really fuck now? I mean that IS what you came to see me for right? - Holly giggled, -Yes James I want you to fuck me. I want you to fuck me like you fucked Heather and Kim. I want to feel the way they say they felt when you fucked them. Make me feel like that. Please make me feel like that James. - I started slowly, drawing back until only the head of my cock was left inside and then pushing forward equally slowly. She needed to become familiar with the sensations she would be feeling when we fucked and I wanted to make sure she was ready for me. She moaned as I pushed back into her and her moans increased in pitch and volume as I went deeper. But after a couple of strokes, she knew what to expect and she settled into what was going on. I began to move faster, and soon I was in a regular steady rhythm. Holly was moaning and crying out as my thrusts got slowly harder and more forceful. She seemed to be thoroughly enjoying herself and it encouraged me to feel free to fuck her like she wanted -"like an experienced and very horny woman! I pushed deep into her once more and held myself there I grabbed her by the hair and pulled her head up to look at me. -Okay slut, now that you have been broken to the saddle, so to speak, are you ready to be ridden like a real horse? Are you ready to be fucked like a woman and see what Heather and Kim were raving about? - -Oh Please, James! Please fuck me like you fucked Heather and Kim! I want to feel that way! I want to feel what it -(TM)s like to be fucked good and hard. They told me how wonderful it was and I want that too! Please, please fuck me! - She practically sobbed as she spoke. -All right then, but you -(TM)d better hang on to something -" it -(TM)s going to get kind of wild here in a second, - I warned her. I watched as she grabbed up a couple of handfuls of bedsheets and got herself ready. I drew my cock back and then I let go. I slammed into her at full speed and full power. Instantly I drew back before she could even gasp a response and slammed into her again. I fucked her hard, fast, and deep without giving her a chance to catch a breath or rest. -OHMYGOD! Oh, Fuck! Oh! Oh! Oh! - she cried out when she was finally able to get enough breath to make sounds. She couldn -(TM)t do much else except hang on and ride it out like a bronc rider in the rodeo. Only this ride lasted a lot longer than eight seconds! I pounded the young girl -(TM)s tender cunt like I wanted to punch a hole in her. If she wanted to be my slut she would have to get used to being ridden and ridden hard. I didn -(TM)t want to hurt her but I wasn -(TM)t taking it very easy on her either. She was a woman now and she would have to learn to fuck like a woman. This was going to be part of her education she couldn -(TM)t get in the classroom. I knew that in just a couple short years, she would be leaving high school and leaving me behind. I wanted her ready for whoever might take over my job as her main fuck partner. Chapter 8 I -(TM)m not sure how long I kept up the abuse on this young pussy but she took everything I gave her and wanted more. I remember thinking that I was going to really enjoy the next couple of years of tapping this little fuckslut and I wondered if her pussy felt this amazing what would it feel like to take her anal cherry as well. I also had not seen her oral skills, although I assumed since she -(TM)d never seen a cock before, they were practically non-existent. We -(TM)d have to work on those as well. Yes, there was much to do to bring this girl out from her sheltered and overprotective cocoon, but we had time and she was definitely excited and inspired to learn all she could about how to please a man from me. Just as my thoughts were looking into future plans and goals for Holly, she made the announcement that we had both been waiting for. -Oh God, James ... I -(TM)m going to cum ... I -(TM)m ... I -(TM)m... -OH FUCK, I -(TM)M CUUUMMINNG! - I leaned down and lay on top of her. I wanted her to feel my weight and I wanted this moment between us to be close and intimate. This was the first time she had ever cum with a man inside her and I wanted to personalize it for her. She wrapped her arms around my neck and buried her face in my neck. She gripped me tightly as I felt her womb fill with her warm fluids, leaking out around my still pistoning cock. She spasmed and convulsed as her orgasm ravaged her body and yet she still hung on. I held her and rocked her a bit as I moved inside her talking to her and encouraging her to let it all out. After a few moments, she pulled her head from my shoulder. Her eyes were wet. -Thank you, Mr. Longfellow. Thank you, James, for making me a woman. Thank you for being so sweet and so gentle. You have made this very special and I will always remember this time with you. - Then she kissed me tenderly on the cheek. -Oh, I think we can do better than a kiss on the cheek, don -(TM)t you. After all, you are a woman now! - I said with a smile and we kissed the way a man and a woman do when they have shared something special. I rolled off her and lay beside her holding her and letting her bask in her newfound womanhood. -So Holly, how did you get here anyway? I didn -(TM)t see a car out front when I answered the door. Is your mom or a friend coming to pick you up? - -No, I walked here. My mom is busy working ... she doesn -(TM)t even know I came over here. - -You walked here? Holly that must be two or three miles! - -Only if you stay on the roads. But I cut through a couple of alleys, through a vacant lot, and took another shortcut so it wasn -(TM)t as far as that. - -Well, I can -(TM)t make you walk home after what we did. I will take you home. Your mother won -(TM)t be home for a while right? - -No, not for several more hours. She -(TM)s pulling a double shift tonight at the diner. She won -(TM)t be home till around 11:30 pm tonight. -They were shorthanded tonight so Mom wanted to pick up some extra cash. That -(TM)s why I came over today -" it -(TM)s the perfect chance for us to have some time together. More time than we get after school. - -I see. Well if your mother won -(TM)t be home till later, that -(TM)s plenty of time. You -(TM)ll even have time to take a shower and get all cleaned up before your mom gets home. - -Thank you, James. But I don -(TM)t have to go home right now, do I? I mean, you haven -(TM)t ... um... - -No honey, you don -(TM)t have to go yet. Actually, I wasn -(TM)t doing anything very important today anyway. Just catching up on some housework and laundry mostly, - I said. -Oh, I can do that! Let me help you, James. That -(TM)s sort of my job ... I do odd cleaning jobs to help out with the bills. -When someone needs help with their housework or grocery shopping or something I come over to give them a hand with the odd jobs that they just don -(TM)t have time to get to, - she said. -Oh? And what do you charge for these services? - I asked, a thought brewing in my mind. -Well, it depends. Usually, we work out a figure between us that we both agree on. Sometimes it -(TM)s a one-time deal, sometimes it -(TM)s a scheduled thing every week or two, - she said. -So does your -~Girl Friday -(TM) business keep you very busy? - I asked. -Not really. It comes in spurts sometimes -" I -(TM)ll have two or three people who need my help one week and then nothing the next. It -(TM)s not real steady work, unfortunately. But I usually make a couple hundred a month on average I guess. Anything helps mom says, - she said. Then she raised up on one elbow. -Why are you asking about what I do, James? - she asked, looking intently at me. -Well, I was just thinking that with my work at school, I come home and I am usually too tired to deal with much more than popping something in the microwave for dinner. -So I let this place go until the weekend, then I spend Saturday and Sunday getting it picked back up and everything done for the next week. -I -(TM)m thinking a -~Girl Friday -(TM) might be just what I need to help out around here myself. Know anyone who might be interested in the job? - -Oh James, really - Are you serious -" you want me to help you around the house here? Yes, oh yes, I would love that! - she said, hugging me so tightly I could barely breathe. -Okay, okay, Now this would only be on Saturdays but every week. Is that okay with you? - I asked. -Yes, that -(TM)s perfect. Most of my other jobs are during the week anyway, so that will be fine! - -Okay, now I will need someone to do the laundry and clean. I will pick things up, but I need someone to vacuum, dust, mop, and clean the bathrooms and kitchen. I have a dishwasher so the dishes will be easy -" they may even be done by the time you get here. - -That sounds easy enough. I can do all of that, no problem, - she said. -Okay, how much would a -~Girl Friday -(TM) cost on a weekly basis for something like that? - I asked. Holly paused for a moment. I don -(TM)t think she wanted to quote too high a price for fear I would back out. But she also didn -(TM)t want to be gypped or cheated either. -Well, if I -(TM)m only working on Saturdays, how does ... um... $200.00 a month sound? Is that too much? - -I -(TM)ll tell you what. I know how this house gets by the time Saturday rolls around. I will give you $100.00 a week if you will show up every Saturday to clean. And if I need you any other time, I will give you $100.00 for that day as well, - -A hundred a week? Really? Oh, James, you are a wonderful man! Yes, yes I will be here every Saturday ready to go to work! Oh, this is going to help so much! How can I ever thank you, you dear sweet man! - she said, tears running down her cheeks. -Well, I know of one way... - I said, getting back on top of her. She held her arms open for me and spread her legs ready to start up again. -James, there is one other thing I wanted to talk to you about today. It -(TM)s about what I said about you being like a father to all of us kids at school, - she started. -Yeah, I remember what you said. Why? - -Well, you know I don -(TM)t have a father and what you said about taking care of us, of me, really made me think. I hope you won -(TM)t think I -(TM)m weird or anything, but now that I will be coming over every Saturday, would it be okay if I ... um ... called you ... Daddy? - -Daddy, huh? I think I can live with that. If I can call you babygirl ... deal? - I said. -I would love to be your babygirl, Daddy. - The smile on her face spoke volumes. -Good. Because slut doesn -(TM)t really fit with you. Heather and Kim, yes. But you are too sweet and innocent to be a slut. At least for now. And I don -(TM)t want you to -~grow up -(TM) too fast! - -I promise, Daddy. I will be your babygirl for as long as you want me to be, - she said smiling coyly. With our -business - concluded, we got back to the reason she came over here today to begin with. I took hold of my cock and began rubbing the tip around her pussy lips again. This time it wasn -(TM)t so much lubricating it as it was getting her arousal up again. Which didn -(TM)t take much since she had already cum once and was still not fully recovered from it. Playing in her pussy and rubbing my cock against her still sensitive clit got her fire rekindled in short order! Holly made have been very new to the sex scene, but her pussy was an old hand at it. Within only a few strokes she was wet enough that lubrication was no longer an issue, and a few more strokes had her pussy drooling like a hound dog watching a steak cook! -Oh please Daddy, please don -(TM)t tease me. Put that beautiful cock in me and fuck your babygirl good and hard! Please, Daddy, I want to be a good girl for you. Please fuck me! Please! - Now don -(TM)t misunderstand me and don -(TM)t think I -(TM)m some kind of sexual pervert or anything, but when Holly called me Daddy and told me to fuck his babygirl, it made my cock harder than I can remember it ever being! I pulled my hips back so that the tip of my cock rested at her entrance. Then I looked up into that beautiful little girl -(TM)s face, those soft blue eyes and that perfect mouth. I moved forward watching those eyes get bigger, those perfect lips get further apart and that little face with its surprised and astonished look on it as I opened her pussy tunnel once again. It was almost as if she -(TM)d forgotten how wide I made her only moments ago and now that I was moving back into that newly opened country she was reminded that she was not with a boy anymore. She began to quietly plead with me like a little girl who wanted a new toy. -Please, Daddy, please fuck me. Daddy, please fuck your babygirl, please, please, please Daddy. Oh, your cock feels so good, fuck your little girl with that big fat cock please! - I sank my cock slowly into her until I had touched the bottom once again. But this time I didn -(TM)t wait for her to get used to me. I just went to fucking her. I raised up off her bracing myself up with my arms so she could breathe without me on her chest. She placed her hands on my chest and wrapped her legs around my waist. I began fucking her hard and deep with a medium speed so she could feel me move inside her she began squirming and writhing almost immediately as the sensation of my cock sliding in and out quickly drove her to distraction. I watched fascinated as her young full tits bounced up and down with the impact I was making on her pussy. Part of me wanted to reach down and grab one of those tender tits and use it like I was using her pussy but I thought better of it. She was still getting used to fucking, I didn -(TM)t want to add too much sensory overload to her just yet. There would be time to break her in right. For now, I wanted her to enjoy what I was doing to her. And she was enjoying it. I could tell from the way she moaned, the way she flailed her long blonde hair in a tornado around her head, and the way her body reacted to my every move. I could sense that she was getting close to another orgasm already and I too had just about reached my end. -Okay Holly, I -(TM)m about to cum. How do you want to do this? - I asked her. -Do you want me to pull out and shoot it onto your tits or your belly or do you want me to cum in your mouth so you can taste it? - I asked. With this being her first time taking a man -(TM)s cum I wanted to give her a choice. After this, I would determine where I came on her. -Please cum inside me, Daddy! I want to feel you cum inside me. I -(TM)m on the pill, so don -(TM)t worry about that. But I want my first time to feel your cum in my belly, Please cum inside me! - she implored me. I couldn -(TM)t resist those soft pleading eyes. -Okay, but I want you to cum with me, babygirl. I want you to cum with Daddy. Are you ready? - -Yes, Daddy I -(TM)m ready. - Okay then, I said and I pushed deeper than ever and held myself there as I exploded inside Holly -(TM)s pussy. The first jets hit far back on her pussy walls and triggered her own orgasm. She pulled me down onto her tightly and held me as her dam broke -OHH FUUCK DAAADDEEE! - she screamed clutching me as she flooded her pussy with her juices. Our juices mixed together in her washing machine cunt before leaking out around my cock and running down the crack of her ass to add to the cum stains already on the sheets. It would be a tough call as to who enjoyed the sex more her or me but we both collapsed after cumming, breathing hard and totally satisfied. Holly recovered first and she moved to put her head on my chest playing with my chest hair and purring like a happy kitten. I reached up to stroke her long blonde hair and she looked at me smiling. -Thank you Daddy for making me a woman today. I do want to be your good girl, but I also want to be a big girl for you. I like being called babygirl very much, but I like being a big girl for you here in bed. I want to learn how to please you, Daddy, how to make you feel good, and how to make you happy. Do you understand what I mean? - -Yes, babygirl, I understand what you are trying to say. And I will help you learn all you can about sex and how to please a man. I will show you what I like and how I like it. But I will also show you things that you will need to learn. -I know you have never tried blowjobs or anal sex -" we will be doing both in the future. I will show you many things that I -(TM)m sure you will enjoy. - -I am looking forward to that, Daddy. I am looking forward to every Saturday I spend with you. - -As am I, my dear, - I said. And as I lay there with Holly in my arms, I thought about how things had worked out for me. I have three beautiful girls who I can have sex with any time I want. I have Holly as my babygirl, Kim as my slut, and Heather who has already let me know that she is up for anything I want to do sexually. Yep, I was looking forward to the next couple of years at Franklin Heights Alternative School! That next Monday I went to school looking forward to the end of the day. I was supposed to have Heather as my Monday meeting but during the day Holly came to see me for a moment between classes. -Here is the list of cleaning supplies I use and where I use them, - she said. I had told her Saturday before I dropped her off at home to make a list of what she used and I would have them at home waiting for her when she came to clean the house. I looked over the list and it didn -(TM)t seem too bad -" most of it I already used anyway but there was a couple of new items. -Okay Holly I will make sure I get to the store for these things before Saturday, - I said, folding the paper and putting it in my pocket. -I told Mom about my new client and what you will be paying me. Mom cried just like I did. You are such a wonderful man, Mr. Longfellow, for helping us out like this. Mom said to tell you thank you... - then she moved closer and whispered, -but I -(TM)d rather show you! - I smiled and assured her she will get the chance to thank me Saturday. She smiled then hurried off to her class before she was late. And so it went for the next three weeks. I rotated the days that I saw the girls and Holly came over every Saturday to clean. And yes, when she took her -lunch break - I made sure her -appetite - was fulfilled! Then one Monday I was in my office doing some paperwork when the intercom on my desk buzzed. -Mr. Longfellow, Sir there are three ladies here to see you. - Miss Blakely said over the intercom. -Send them in please. - Then the door opened and Holly, Heather, and Kim came in. -To what do I owe this pleasure? - I asked, fearing trouble. -Don -(TM)t worry Mr. Longfellow, we aren -(TM)t in trouble. It -(TM)s just we would like to ask you something. -We have been talking amongst ourselves about you and this arrangement that we have and ... well if you aren -(TM)t doing anything this weekend, we -(TM)d all three like to come over and make a party out of it, - Holly explained. -Yeah, This way you could have all three of us at once. Kim and I have already played together a few times and Holly says she wants to learn what being with a girl is like too. So we thought we could all get together and play with you and each other, - Heather added. -So all three of you would like to come over and have sex with me together, is that right? - I asked. -Yeah, would you like to have three hot girls to entertain you and do anything your heart desires? - Kim asked with a playful grin. -Girls, I don -(TM)t know any red-blooded man that could say no to such a proposition! Of course, you can come over! - I said. -Oh good! - the girls said, clapping and giggling. They left my office, headed for their next classes and I sat at my desk daydreaming about the coming weekend and trying to figure out all the delicious possibilities! It was going to be a wild, sexy weekend to be sure!