I took Holly into my office and made her sit down. Again I had a large “file” on her on my desk for her to ponder about. And I began with her just like I had the other two.
Holly was the youngest and newest member of The Bad Girls. She was also the quietest. Her biggest problem was that she so wanted to belong that she ignored what she knew was wrong just so she could fit in.
I could tell pretty quickly in talking to her that she was basically a good girl just hanging around with the wrong element. Still, that was her choice and people still get in trouble just by associating with troublemakers.
She skipped classes, smoked, and did all the things the other girls did, even if it wasn’t her idea to begin with. So she would be given the same options as the other two.
Holly’s youth and naive nature would work to my advantage. Once I told her what I was offering and what she would face if she didn’t accept my offer, she got scared.
She didn’t want to get in any more trouble than she was already in and she knew that if she didn’t graduate so she could get a good job and help out with the family finances, she would disappoint her mother terribly.
Especially when her mother learned why she hadn’t graduated. So Holly got on board the Longfellow Express right away once I convinced her that no one else needed to know about our little arrangement.
A couple of years of playing slutty schoolgirl to me in exchange for a diploma and an easier life down the road was a small price to pay in her mind.
And so with Holly’s consent secured I had talked to all three girls separately. It was time to bring them all in and finalize things. I kept Holly with me in the office and brought Kim in from the waiting room.
“Now sit down Kim but do not talk. I don’t want either of you to say a word until I tell you, got it?” Two nodded heads told me they understood. I got on the intercom to my vice principal. “Ms. Rayburn, please send Heather into my office.”
Presently Heather came in hesitantly and unsure of what was going to happen. “Sit down Heather and do not speak until I tell you to.” She obeyed, cautiously sitting on the edge of the imitation leather sofa in my office.
“Now then girls, I have had a nice little chat with all three of you and I have learned some very interesting facts about each of you. We discussed your past performance and what the future may hold for you.
“None of you knows what I said to the other two and I did that purposely – I want you to make up your own minds without coaching or direction from the others. And so with a simple yes or no answer, nothing more, Heather do you understand what we talked about?”
“And do you agree with it?”
She paused for a moment. “Yes.”
Then I turned to Kim and asked her. “Kim, do you understand what we talked about?”
“And do you agree with it?”
Her answer was quicker in coming. “Yes.”
Finally, I turned to Holly.
“Holly, do you understand what we talked about?”
“And do you agree with it?”
She answered right away. “Yes.”
“Good. I am glad to see that all three of you are using your heads for a change. Now, this arrangement is between the four of us and ONLY the four of us. If word gets out from anyone one of you, the whole deal is off for all of you understand?
“I won’t even bother to ask who it was that said something. So it would behoove you not to speak about this to or around anyone else outside this room.
“Now I am sure you all have questions and concerns – this is a rather unusual and unique situation. And I will be happy to answer any questions you have. But let me assure you I am no monster. I am not going to hurt you or do anything that will cause you any lasting physical or mental harm.
“In fact, I am hoping that you will find this experience quite enjoyable once you get past the initial anxiety and see just what being with me means.
“I think you will find sex with me much different and much more satisfying than your current boyfriends. I have the experience and knowledge of what makes a woman happy that these high school boys just haven’t got.”
Just then Holly raised her hand. “Yes Holly, what is it?”
“Um, I was just wondering… when would this… start?”
“Well, today is Wednesday so it’s a bit late to get started this week. I was thinking we would begin our new arrangement starting next week. I will call one of you girls in on Monday, one on Wednesday, and one on Friday of next week to give you your first ‘lesson’.
“Why don’t we start with you, Holly, on Monday. Kim, you will come to see me on Wednesday. And Heather, you are my Friday girl. The following week we will rotate one position and Heather will be my Monday girl, Holly will be my Wednesday girl, and Kim my Friday girl, and so on.
“Each of you will come to the office after school so we can have some privacy. If anyone should ask why you are here you just tell them that I am helping you with your schoolwork. Tell your parents that you are staying after school on your designated day for some tutoring help. I will take each of you home after we have finished,” I said.
I let the girls go back to their classes with notes from me so they wouldn’t be marked as tardy. The girls had the rest of the week and the weekend to think about and wonder what the next week would hold for them. I’m sure there were sleepless nights and vivid, erotic dreams for all three girls… I know I sure had some sweet dreams!
The next week would prove to be an interesting and exciting one. I had three lovely young ladies who, because of their mischief-making and defiance, would now learn that sometimes there are consequences to their actions and that defiance brings about punishment.
I drove to the school Monday morning looking forward to this day more than most. Like with most people, Monday mornings usually brought extra work and hassles that accumulated over the weekend.
But I got through the flurry of emails, phone messages, and paperwork easier this Monday because I had something to look forward to after school. Once I was caught up from the Monday morning rush, things slowed down to a pace that was more agreeable to me.
I had some paperwork to do – requisition forms to sign, the typical bureaucratic nonsense that a manager would have to do. But it made the afternoon go by and before long I heard the bell ending the school day. At last!
I knew that Holly would be arriving soon so in preparation for her I cleared off my desk of any paperwork as well as all the desk accessories I had there. I put my desk lamp up on top of the filing cabinet where it wouldn’t get broke and made sure the curtains on the windows were drawn.
It was probably twenty minutes or so after the final bell when I heard a soft knock on my door.
“Come in,” I said. I watched as the door slowly opened and a face peeked around the edge. It was Holly. “Come in, Holly.”
She slowly opened the door and came in… cautious as a rabbit in a den of wolves.
“Please close the door and lock it. We don’t want to be interrupted,” I said. Holly’s eyes got wide and she hesitated. I don’t think she liked the idea of being locked in here with me!
“Holly, I said close and lock the door, please. Come on, we don’t have all night,” I repeated.
She closed the door and I heard it click. But when she turned the lock the click must have sounded like thunder to her because I saw her jump with a start. She drew a deep breath and turned to face me. I was still sitting behind my desk as she approached. She came up to the desk on the opposite side of me and stood there.
“I-I’m here like you wanted, Mr. Longfellow,” she said quietly.
“Indeed you are,” I said. “I am glad to see you want to hold up your end of our arrangement. That is good – your reliability will go a long way in making this easier for both of us.”
As I talked I walked around the desk towards her but instead of walking up to face her, I moved around behind her. She stood perfectly still although I could see her trembling from halfway across the room.
I came up behind her and put my hands on her upper arms just under her armpits. She jumped when I first touched her.
“Relax, Holly, it’s all right. I am not going to make you do anything you do not want to do. I will ask you to do things, yes, but it will be your decision whether to actually do them, understand?” I said calmly and quietly in a reassuring tone.
“Y-Yes Sir,” she said, “But what will happen if I don’t?”
“Well, Holly, I am going to trust that you want to cooperate. I am willing to help you, but you have to meet me halfway. It wouldn’t be right to just write you out a diploma right here and now when other kids have worked hard and put in the effort to get one. I think I am being very generous in giving you another chance. Don’t you think you should give back something in return?”
“Good girl. Now, why don’t you start by getting more comfortable? Take off your top,” I said.
Holly was wearing a very soft red sweater-like top with white trim. The top was cut high enough that there was about four inches of her skin showing between her top and the skirt she wore.
With shaky hands, she began unbuttoning the front of her top. When she reached the last button, I reached around her and took her hands in mine. Together we pulled her top open and I slipped it down off her shoulders. I took the top and folded it in half placing it carefully on the sofa.
“Good. Now let get you out of that skirt as well, shall we?” I said.
Holly’s skirt was white with a red stripe close to the bottom. It was somewhere between a mini-skirt and a knee-length skirt, high enough that you could see her legs between the hem of the skirt and the tops of her over-the-knee white stockings. It was a very sexy little outfit but just tame enough that she wouldn’t get arrested for indecent exposure!
She reached behind her and unclipped the fastener holding the skirt around her waist and once undone, she let the skirt fall to the floor around her ankles. She stepped out of it squatting down ladylike to pick it up.
I took the garment from her and put it with her top just as carefully. I turned and Holly had turned around to look at me now. She looked stunning in her red bra and panties, white stockings, and red high-heel pumps.
“You look very pretty, Holly. I can see why the boys here at school act so silly around you.” I said.
“Thank you, Mr. Longfellow.”
“Holly, you can call me James when we are alone together like this. During school and around other teachers and students, I’m Mr. Longfellow, but when we are alone I’m James, all right?”
She smiled a little. “All right… James.”
I took a couple of steps towards her and took the young girl in my arms. With her five-foot-three-inch height and her five-inch heels, she was close enough to my own six-foot height to make kissing her easy and I didn’t feel like I was kissing a teen-aged girl.
Tentatively at first, Holly quickly warmed up to my kiss, melting in my arms and softly moaning as she felt my tongue push past her lips and find her tongue.
She had been kissed by boys in the past but just as I had said, she was with a man now and I knew a few things about kissing a woman! Her arms, which had at first hung limply at her sides, now raised up to wrap around my neck as she pulled me deeper into the kiss.
My hands, by contrast, moved slowly up her sides to her ribcage and ultimately forward to her tits. Holly may have been a young eighteen years old, but she had a body that wouldn’t quit! I especially admired her tits – a full 32C!
Holly sucked in a breath as I first touched her tits, but then moaned it back out as I began softly caressing the clad mounds. I ran my fingertips lightly along the edges of her bra along the sides and down the front V, teasing her and exciting her with a light, almost imperceptible touch.
As my fingers played over Holly’s young tits, her excitement grew and before long her kisses had taken a more urgent manner. She was kissing me like she was devouring me, hungrily sucking on my tongue and crushing her lips to mine. She was thoroughly enjoying her first real kiss!
I felt her passion and I surreptitiously placed one leg between hers, pressing up against her crotch. It was the perfect move done at the perfect time.
Holly stiffened at first but then feeling me pressing against her hungry young pussy and throbbing clit made her begin grinding against the leg almost humping it.
Holly was controlled by her own lustful desire now, helpless to do anything to escape. Her imagination over the past few days had dreamt up all manner of scenarios… things I might do to her. She wanted to see if my promise to show her things that the boys in the school couldn’t was true or not.
Holly did not have a lot of experience with boys yet. Actually, she was still a virgin, although she’d had a few makeout sessions where she let the boys get to second base and she even let one guy play with her over her panties once. But no one had gotten in her panties yet.
I broke our kiss, leaving Holly gasping for breath and shaking again – this time in desire instead of fear. I reached up to her bra and as she watched I unfastened the clip hold the front together. I slowly parted the cups, revealing her very unteen-like tits, her large, rosy areolas, and the hard stiff nipples in the center.
“You have an amazing set of tits Holly, for someone your age,” I said.
“Yeah, all the Adams women are full-chested. I started developing early and by the time I was in fifth grade, I looked more like a woman than any of the other girls. It drove the boys crazy!” she said blushing at his comment.
“I’m sure it still does my dear,” I said. Holly smiled as she looked up at me.
I smiled in return and then leaned down to take one of the hard nipples into my mouth. I licked the fleshy nub and then blew air across it, the sensation causing it to harden even more almost to the point of hurting.
“Oh, God…” she moaned as she felt my mouth close over her aching nipple.
I started licking, sucking, and occasionally lightly biting the sensitive nipple, teasing and arousing her even more. Holly ran her fingers through my hair, mewling and cooing her exquisite pleasure as I brought her along slowly, building on every layer of sweet pleasure I had already laid down.
After a few minutes of devouring her tender young tit, I switched over to the other nipple to give it the same delicious treatment. But as I did, my hand moved down to begin rubbing her pussy through her panties. I could tell by her fragrance that she was quite aroused now – her scent filled my nostrils and it excited me as I played her like a fine musical instrument.
Holly was moaning and swaying side to side as her mind started to unravel. Her eyes closed, not wanting anything to interrupt this ride. Her head went back and her long blonde hair fell over her back like a waterfall.
I could feel her panties developing a wet spot as I continued to rub them. I hooked a finger on one leg hole and my thumb in the other, gathering the front of her panties into a thin rope, which I then began sawing in between her thick puffy lips and drawing over her erect little clit. Her moaning increased both in volume and intensity.
“Oh please, James… please…”
I knew that we didn’t have much time – certainly not as much time as I would have liked to have spent on this delectable young thing. I needed to press on and show her that my talk earlier was not bragging, but stating the facts. I was a good lover – I’d had many women in my past tell me so.
And I wanted this girl to experience what I knew I could do to her. She may have had boys fumbling and bumbling around her in the past, but she was up against a man now… a man with skills and techniques she couldn’t even imagine!
I stood up and turned her to face the desk. I pushed her forward, bending her at the waist and laying her face and chest on the desk.
“Wait! W-What are you going to do?” she asked, panicking a bit.
“Just lay on the desk and relax, Holly. I am only going to rid you of these panties for now. I told you I would tell you what I’m going to do and you can choose to stop it if you wish.”
Holly remembered what I had said about meeting me halfway and how I said it wouldn’t be fair for me to just hand her a diploma when other kids had to work for it. She knew that she had gotten herself into this mess and now this looked like the only way she had to get out of it.
As she lay over the desk thinking about her situation, my hands began roaming over the backs of her legs, the insides of her thighs, and brushing against her pussy. It made her moan, feeling incredible… and I had called her a good girl… I knew she wanted to be a good girl for me, she wanted to please me.
“Um… okay, I guess it’s all right if you take off my panties,” she said after a brief hesitation.
I reached up and took the waistband of her wet red panties and began pulling them down over her tight young ass. As I pulled the sopping panties further down, the cool room air hit her overheated pussy and she gasped.
“You are very wet, Holly, are you enjoying this?” I asked. She couldn’t see it, but I had a wide smile on his face.
“Yes…” she replied, the longing moan in her voice apparent. I finished pulling her panties down and she lifted her feet so I could remove them.
With the young teen stripped of everything save her stockings and heels now and bent suggestively over his desk, I knelt down behind her. I grabbed both firm, tight asscheeks and pulled them wide apart, exposing her crinkled asshole and her wet, pink pussy.
“Mr. Longfellow! What are you doing?” she asked, startled at this new move.
She quickly found out as I pushed my face between her spread cheeks and licked at the wet pink pussy I had uncovered.
“OH, GOD! OH, James!” she squealed. She tried to stand up, but I swatted her ass sharply.
“Now lay back down on that desk and don’t get up until I tell you to!” I said sternly. Holly laid back down quickly wondering what I was planning for her. But her concerns quickly faded as I resumed eating her sweet honeypot from the back.
I licked and lapped at her sweet hole and then, as if that wasn’t pleasurable enough, I licked my way up her perineum to lick at her tight puckered anus as well! Holly was beside herself. She writhed and moaned and whimpered as I ate her pussy and ass, back and forth, keeping her mind flooded with mixed messages from down below.
“Oh God, James! Oh, yes! Ooh right there! Oh, OH, God! Ohhh…!”
Holly may not have known what was happening to her, but her pussy knew what to do and her juices began flowing in abundance in response to my tongue. I greedily lapped them up almost as fast as she produced them and my tongue, furiously working to capture them all, only made her squirm and wriggle more.
Then I pulled another trick out of my bag. Using one side of my face to hold one of her asscheeks in place, I took my now free hand and used my thumb to rub across her exposed and erect little clit.
This lit Holly up like a streetlamp!
“Oh Fuck, James! Oh, God! I’m gonna cum! I’m gonna CUUUMMM!” she screamed. And just as the words passed her lips she did, pouring her juices out in a torrent that I had no hope in stemming. Her sweet honey poured out of her, soaking my pants and shirt and running down her legs to get her stockings wet as well.
Finally, her orgasm passed and she lay there on my desk panting and flushed red with effort. Her pussy was still dripping as I stood up. I watched her as she rested on the desk while I got undressed. I was down to my boxers when she finally raised her head and looked at me.
“A-Are you going to… fuck me?” she asked, wide-eyed.
“Well, that was the general idea here Holly,” I said.
“Mr. Longfellow there’s something I need to tell you… I’m a virgin. I’ve never been with a man before!” she said.
“A virgin? Really? I just figured running with girls like Heather and Kim you would have been with boys before. You’ve never…” I asked, shocked at this news.
“No. Heather and Kim don’t know that I’m a virgin – if they knew I was still a virgin, they probably wouldn’t have anything to do with me. But I’ve only made out with boys and I let one special guy rub me down there under my skirt but over my panties.
“The only thing that has ever been inside me is my fingers and the doctor’s instruments when I have a checkup. No one has ever even eaten my pussy like you just did… which was amazing.”
“So this was your first orgasm?” I asked.
“Yes… at least the first one I didn’t give myself!” she said, blushing bright red.
“Well, I appreciate you telling me… before we got too far into this,” I said.
“Does this mean that the deal is off for me? You know, since I’m…” she asked.
“No dear, it just means I will have to think about this and see how we can work your particular situation. I know that you need to graduate and help your mother. I want you to graduate too. I will figure something out. Have you ever given a boy a blow job?”
“No, I’ve just jerked him a little. I’ve never even seen a guy cum before,” she confessed, looking down sadly.
“I see. Well, this is a lot to consider, and we should probably stop where we are. I’m glad that I was able to give you the first real orgasm you ever had – that’s quite a privilege for me. I’ve never been anyone’s first orgasm before” I said.
“I’m sorry Mr. Longfellow. I know you had me come here for sex and I’m sorry I couldn’t do it. I really hope you can figure out something… I want to graduate. I need to graduate,” she said.
“I will see what I can come up with for you, Holly. Meanwhile, you get dressed and I’ll take you home.”
The ride home was quiet. Holly didn’t know what to say and I didn’t want to make her feel any worse than she did. She gave me directions to her house but that was the extent of our conversation. That is until we were a couple of blocks from her house.
“Wait, James,” she said, “Could you please pull into this parking lot for a minute?”
“Sure, why?” I asked. I pulled into the parking lot and stopped the car.
“Mr. Longfellow, I want to thank you for the chance to make up for all that I’ve done and to graduate. I know we had a deal… an arrangement, and I’m sorry that I couldn’t do what you expected today. But you were very sweet and very nice about it.
“You already proved you are more ‘man’ than any boy I ever dated. Most boys would have gotten mad that I didn’t have sex with them and dumped me. But you were different and I really appreciate that.”
Then Holly leaned over and kissed me passionately, letting me know just how much she appreciated my understanding.
Copyright © 2021 by Master_Jonathan
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