“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’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’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’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’t try out for anything is that they wouldn’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’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’s the reality I have to deal with. I can’t do anything to change it – I’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’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’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’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’t make up for absentee parenting, but it could be a lot worse. I had to admire Heather’s outlook and acceptance of her situation.
That didn’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’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’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’m not sure what that will be but know one thing – while you are in my school, you matter. To me, you matter.” I said.
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’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’ve ever seen and I’ve seen my share. I want you to do me a favor, though.
“I’m sure Kim has told you what I did to her pussy the other day… how I ate her pussy until she couldn’t take it anymore. I’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’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’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.
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.
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.
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’s house was only a few blocks from the school and it didn’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’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’m not exactly on the local social register and I don’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’m sorry to come by like this but I need to talk. Can I come in please?” she asked.
“Of course. I’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’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’s the problem, Holly? What’s this all about?” I asked.
“Please don’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’t have, but I couldn’t find your number in the phone book,” she said.
“That’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’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’t in school?” she asked.
“Yes, James is fine.”
“James, I couldn’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’t stand it – please, please fuck me like you did them! I know I’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’s all I’ve BEEN thinking about! It’s all I’ve been dreaming about. I can’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’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’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’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’t want her to get mixed up with the wrong boy and end up getting hurt.
I could totally understand her mother’s concern. While not a parent myself, I couldn’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’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’s not too late to turn back you know,” I said.
“I’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. I looked 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’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’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’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’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’m not… not that I know of, at least.”
“That’s good to know. Frankly, I don’t like wearing the damn things – I lose a lot of the sensation and the fun by having to wear one. But I don’t know Heather and Kim’s sexual practices yet and I don’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’s time for that.. right now I know I have one girl I don’t have to wonder who she’s been with!”
“Yeah, I’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’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’ve never been undressed in front of another guy,” she confessed quietly.
“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’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.
“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’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’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’s body and apparently a woman’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’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’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’t you, my sweet?”
“Ohhh… yesss,” she moaned as she rode the hand in her crotch.
“Yes, I’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’ll bet you will enjoy them too.
“I can do things to you that you can’t even imagine… make you feel things your mind can’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.
Copyright © 2021 by Master_Jonathan
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All names, characters, businesses, places, events, and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters portrayed in this story are over sixteen (16) years of age.