While most teachers, students and other school staff were enjoying the last day before classes started, I, teacher Philip Caan, was waiting in my classroom to speak with a student I had met at the end of last term. Harper Stone was a seventeen-year-old soon to be senior who, as of the end of last term, was a shy, slightly awkward girl with a lot of issues fitting in with her peers. I met with her and her parents at the end of the previous school year and promised them I would speak with Harper and help her connect better with her fellow students, starting with a little meeting the day before school to strategize on things we could work on throughout the year. However, helping Harper fit in better would likely be difficult.
Harper was a friendly girl when I met her, but she was really shy and had a hard time looking people in the face. In addition, I’m sure you know how cruel high schoolers can be when it comes to one’s personal appearance. Harper was 5 foot 3 with milky white skin, long red hair, and she tended to always keep herself covered completely, save for her hands and head. I’m not advocating that my students dress sluttily, obviously, but there’s no doubt that her shyness, her desire to dress modestly, and her lack of a noticeable ass or breasts, were more than enough for the school’s mean girls to notice and pick on her. I wasn’t sure how much I could help her out, but anything was worth a try.
I was working on a lesson plan for the first week of classes when Ms. Cooper, the head janitor who had to come in to let Harper and I into the building when no one else was here, knocked on my door.
“Hey, Phil. That student, Ms. Stone, is here, so I’m going to leave and you can close the doors behind you on the way out. They’ll lock automatically. See you tomorrow.”
“Thanks, Marnie, and thanks again for coming in to let us into the building. See you tomorrow!”
With a wave of her hand, Marnie left and I stood to accept Ms. Stone into my classroom. Little did I know Harper Stone had gone through one hell of a transformation over the summer.
“Hi, Mr. Caan!” an overly jubilant Harper said as she practically skipped into the room.
Gone were the loose-fitting shirts, baggy pants and flowing sweaters that used to make up her wardrobe. All her previous clothing had been replaced by an extremely low-cut, spaghetti strap cream-colored tank top made of almost see-thru material, and very tight blue jeans. In fact, the tank top was so low-cut at the chest that I could see nearly half of the cups of the crimson red bra she was wearing underneath the top. I had to try REALLY hard to keep myself from staring at her chest.
“Hi, Harper, thanks for coming to see me before school starts. Please, have a seat.”
Harper continued to beam as she walked past me and sat down at the desk in front of mine. The teen’s clothing style and mannerisms were not the only things that changed over the summer; Harper had also put her fiery red hair into a set of pigtail braids, started wearing makeup like blush and a light bubble gum pink lip gloss, and it looked like the comment I made earlier about her breasts and ass were now null and void. As she walked over to the desk I could she just how much her ass was straining against the fabric of her blue jeans, and while I didn’t mention it earlier, her breasts had gone from being practically non-existent to something that had to have been at least a large B or a small C.
At first, I tried to keep my composure and prevent my dick from appearing visible in my pants, but eventually I gave up and rushed behind my desk to hide the growing erection that was becoming increasingly harder every second. I moved quickly to my desk and sat down.
“Well, Harper, I see you’ve changed a bit over the summer. You certainly seem a lot happier and… outgoing since I last met with you,” I managed to awkwardly spit out.
“Yeah, SO much has changed since last year. My friend, Becky, showed me this website that has a lot of tips on things like clothing, makeup,” she giggled nervously, “boys. It’s been so helpful. Plus, it doesn’t hurt that these finally arrived.” She used a finger to circle her breasts and I had no choice but to visibly gulp and tighten my grip on the arms of my chair.
“Well, there’s a lot of other ways to connect with your fellow students than simply, uh, biology, so to speak. I am glad however that you seem a lot more confident and happy than you did when I last met with you. In fact, it almost seems like you don’t even need to meet with me anymore during the year.”
The statement wasn’t exactly true. I didn’t want Harper to think she needed to use her body and revealing clothing to fit in, but, more importantly, I really needed to get her out of here so I could bust a nut and relieve the pressure in my groin that was almost causing me physical pain.
“Actually, there is something really important that I could still use your help with.”
“Sure, whatever I can do to help make your last year as good as possible.” ‘Please let it be something quick and easy,’ I prayed. I couldn’t take looking at this hot teenage girl any longer.
Harper smiled wickedly and slowly walked over to my desk and leaned on it with both hands as she stared straight at me.
“You see, I’ve had a little experience with boys over the summer, but they’re just boys, and when I go into my senior year, and finally on to college, I want to make sure that I’m ready for all the men I meet.” She walked around the side of my desk and started to gently rub my shoulder. “I think you can teach me how to be ready, Mr. Caan.” Her hand migrated to my chest and began to rub there instead.
“Harper, this is really inappropriate. I’m twelve years older than you, and more importantly, I’m your teacher.” Predictably, this didn’t work.
“That’s just it, Mr. Caan. Not only are you so much more experienced than any of the boys I’ve been with, but you’ve been the friendliest teacher to me ever since I moved to this school. Even before we had that meeting to discuss helping me fit in, you always said hello to me in the halls, you helped tutor me in math in grade ten, and you told off those nasty popular girls when they kept harassing me. You’re the nicest teacher at this school, and I want you to teach me how to fuck better.”
Her hand moved from my chest, down my stomach to my pants. The erection that had previously been covered up by my desk was no longer a secret. In fact, not only was it no longer a secret, but Harper began slowly stroking it through my pants.
“Well, I can tell that at least your dick is interested in helping teach me something, and it’s bigger than all the boys I’ve been with too!”
I couldn’t help but feel encouraged by that, whether it was true or merely an attempt to butter me up to get me to go along with her little plan, it didn’t matter.
“For a man it’s pretty average, but when it’s teased by a really pretty girl like yourself, it gets particularly big and hard.” What was I doing? Was I actually contemplating going through with this?
“In that case, maybe I should stop teasing it and give it what it wants.”
Harper spun my chair to face her and she proceeded to undo my belt, the button on my pants, followed by the zipper, and after pulling my underwear down, she exposed my painfully erect cock to the open air.
“Average, huh? I don’t think so.”
She started slowly stroking my bare cock with one hand as she leaned in to kiss me. Her lips tasted like bubble gum thanks to the lips gloss she was wearing, and they were as soft as one could ever imagine lips would be. It was only three seconds before her tongue made its way into my mouth and began swirling around my own. It was like heaven, but it only lasted for about half a minute before Harper decided to break the kiss and up the ante.
“Let me show you something else I learned to do with my tongue over the summer.”
She stopped stroking me and knelt on the floor in front of me. Once she was in place, Harper grabbed the base of my cock with her right hand and slowly licked the underside of my shaft from the base to the tip. Because of the sensitivity of the underside of my cock, I let out an audible moan. When she finished making a full lick, she closed her eyes, moved her mouth over my cock and proceeded to slowly swallow it all the way down to the base. I moaned ever more intensely as I felt warmth engulf my cock and the tip get gently squeezed by the back of Harper’s throat. After a second to let the feeling linger, she began to move her mouth up and down me as she gently moaned around my cock.
I still had to question if this was a dream. Was the shy, reserved teen from last term actually now not only hot, but also going down on me in my classroom? Frankly, I didn’t care; whether it was real or not, the feeling was more than real enough for me.
“Yeah sweetie, that’s perfect. You’re a really promising student.” This prompted her to look up at me and smile around the dick lodged in between her lips.
Gradually Harper picked up speed and began moving her mouth up and down my shaft faster and faster until she was going full-bore on my dick. Occasionally, she deep-throated me, and due to all the spit that she generated, she would remove me from her mouth to slurp up all the saliva and pre-cum that was sliding down my cock.
“Ugh! That feels good, Harper, really good! You’re gonna fit in really well with all the boys this year.”
“Really, Mr. Caan, you think so?”
“I know so. Now get back to work, you might be graded on this,” I sarcastically jabbed.
“Yes sir!” Harper enthusiastically cheered before going back to work on my cock, this time harder and faster than before. It’s amazing what teenagers can do with a little encouragement and some firm direction.
At some point, without me noticing, Harper had undone her pants and slipped her left hand into her panties, which were the same crimson red as her bra, and began to touch herself. Speaking of her bra, it was time for it to go.
“Why don’t you stand up, honey?” I said as I began to stand and help Harper to her feet. We kissed again, me not giving a damn about how her mouth had previously been sucking my cock, I just wanted to taste and feel her luscious lips again.
“Here, let me help you with that.”
I helped Harper take her tank top off as she undid her bra and both fell to the floor. Her tits were magnificent; even in tone with the rest of her milky skin, her areolas pink and puffy like a teenager’s should be, and her nipples standing full and erect, anticipating more excitement.
“You know, I really should take a break. I wouldn’t want to drain myself before our little lesson has concluded. Besides, I believe in rewarding my students for their progress. Take off the rest of your clothing and hop on my desk.”
Harper smiled eagerly and did what I told her. Meanwhile, I removed my clothing and threw them on the floor along with Harper’s. She perched herself on top of my desk and spread her legs wide open, revealing a clean-shaven pussy, save for a small tuft of red hair just above where her pussy ended. I wasn’t fast enough, apparently, because she licked her fingers and began pleasuring herself without me. I realized I better hurry up, so I quickly knelt in front of her and started licking her pussy up and down to get it wet all over.
A gentle moan escaped Harper’s lips as I licked up and down her pussy, but when I began vigorously flicking my tongue at her clit, her moans started to get louder and louder, making me thankful that no one else was in the building today.
“Oh my GOD Mr. Caan! None of the boys I’ve been with have ever been this good at eating my pussy.”
I didn’t stop to acknowledge her praise, though, as the secret was to keep the pleasure going and drive them crazier and crazier. The ‘stop and slow down’ approach might work on men trying to keep from blowing their loads before getting to the real sex, but for women, the key was to just keep going. It was easier, at least in my experience, for a woman to cum multiple times as opposed to a man, so there was no need to keep things slow and easy when it came to eating Harper’s pussy.
“Oh shit, oh shit, oh shit! Oh, fuck that feels so good!” Harper’s breath had become fast and ragged and she squirmed around so much I had to grab her hips to keep her still enough so that I could keep my tongue focused on her clit.
“Aaahhhh! I’m gonna cum, I’m gonna cum!”
I could taste some of Harper’s juices escape her pussy and make it to my mouth, but I didn’t stop when she climaxed.
“Mr. Caan, I’ve come already. You can stop-, you can staaahhh, oh FUCK!”
I just kept licking and I even put two fingers in her pussy as well and started thrusting them in and out really fast.
“Oh my God, I can’t take it anymore. PLEASE!” Nope. “AAAAHHHH! I’m cumming again!” And she did just that.
After licking up some more of Harper’s sweet pussy juices, I finally withdrew my face from her crotch and looked down to see what I had done. A pool of saliva and pussy fluid had collected at the edge of my desk and began to drip down the front of it. Meanwhile, sprawled across my desk was the redheaded vixen, her head lying off the back, arms stretched out and still gripping the sides of it with her legs stretched wide open. She just laid there and fought desperately to catch her breath.
Eventually, she sat up and spoke, “Is that play of ‘My Cousin’s Back from the War’ still happening this week.”
Why would she ask such a random question after getting tongue fucked the way she had?
“Yeah.”
“And has the bedroom set been built on the auditorium stage with the bed and everything?”
“Yes, it is, but why do you ca-”
“Let’s go to the auditorium, there’s something I want to do.”
She started walking off so quickly that I had to jog momentarily to catch up with her. Neither of us even bothered to put any clothes back on.
‘What the hell is she doing?’
I caught up to Harper who had just opened the doors to the school’s auditorium and started to stride confidently up to the main stage where the set of an apartment was built for the school’s opening week play. The set contained spaces like a kitchen, a living room, and a bedroom, complete with a real bed. As she stood on the stage looking down at me, I asked her again what she was doing.
“Don’t you think it would be so cool if we fucked on the bed that they’re going to use during the school play? When we watch the play, we can think back to all the fun stuff we did on it!”
“That does sound amazing, Harper, but unless you’re hiding a condom on you somewhere, I don’t have one with me and I’m not about to risk getting you pregnant.”
She just laughed at me.
“I’m adventurous, Mr. Caan, not stupid. I’m on the pill, don’t worry!”
I think I’m falling in love with this girl.
I climbed up the stage and started kissing Harper again. The thought of doing such a forbidden thing on the school stage the day before it was going to be filled with hundreds of people was intense! We let our lips leave each other and walked over to the bed hand in hand.
“Now, let’s see how well you fuck, Ms. Stone. We’ll start with something easy.”
I laid on the bed and motioned for her to join me. The teen climbed on top of me, one knee to either side of my hips as she slowly lowered herself on my cock.
“Ohhhhhh,” she gently moaned as my cock filled her pussy. She was almost able to fit me inside of her all the way, but I could feel resistance as I reached the shrinking back of her pussy. “Ohhhhhh, no boy has ever made it all the way back. This is going to feel great.”
Harper began to slowly lift herself up and down my shaft and I helped her by moving her hips up and down. At first, she did an alright job herself, but I wanted her to go faster, so I began to gently add more force to how fast I moved her hips and how much power I put into my thrusts. This also had the added effect of causing her breasts to bounce up and down, and once in a while, I moved a hand from one of her hips to one of her breasts and squeezed them roughly.
“Uhhh, uhhh, uhhh, oh fuck! Oh, fuck that feels good!” Her breaths bounced faster and faster, and as I began to more forcefully jerk my hips and press my cock into the back of her pussy, her moans and loud breaths started to be interspersed with grunts. “Ugh, ugh, ugh, so… deep… so deeeeeep, UGH!”
The speed kept building until we were going at it with all the power and passion we could muster, and the auditorium filled with the pleasurable screams and dirty language of a wild seventeen-year-old hottie getting nasty with her favorite teacher on the set of the school’s opening play.
“FUCK, FUCK, FUCK, FUCK, FUCK, FUCK!” Harper belted out. Occasionally the FUCKs were replaced by the odd SHIT, or OH GOD for variety.
It was time to try a new position though, and I told Harper to get on all fours on the bed while I scooted up to her and entered her pussy from behind. There was no need to start off slow and gentle; we had already been going at it pretty hard when she was on top of me. The difference though, was that I had more control now. While Harper could move herself back and forth slightly, I was in charge of how quickly and deeply I wanted to ram my cock into her pussy, and I wasn’t holding back at all this time.
“YES! Oh God, yes, please fuck meeeeeee!”
“Good girl, you’re my favorite student, Ms. Stone.”
I grabbed both of her pigtail braids and wrapped them around my hands as I pulled her hair back. I could see a few tears trail down her cheeks, but given the begging and passionate screaming that she was doing, I was clearly hurting her in a way she found pleasurable.
“AAAAHHHHH! I’m gonna cum again!” And she did.
After a few minutes of doggy style, I decided there was enough stamina left in me for one more position, not to mention I didn’t think Harper could take much more. If I pushed her too much, she might stop this whole thing before I got the chance to cum myself.
I pulled out of her and instead of trying to direct her, given how much ecstasy she was in, I gently positioned her at the edge of the bed with myself in front of her and raised her left leg over my right shoulder and entered her again. Using my left thumb, I also vigorously rubbed her clit just above where my cock was pumping in and out of her pussy to give her even more pleasure.
I loved this position, and apparently, so did Harper, although I’m pretty sure that any position would be loved by her as long as my cock kept pounding her pussy. I guess the two of us would need to arrange for more lessons together.
“Yeah, you like our little lesson, don’t you, Ms. Stone.”
“Yes, yes I like it a lot, Mr. Caan,” she responded in a ragged, out-of-breath voice.
“Do you want to have more lessons like this?”
“Yes! Oh God please, teach me mo – teach me mo… OH FUCK TEACH ME MORE!”
Harper’s begging pushed me over the top, and with a series of loud grunts I spewed stream after stream of cum into her blazing hot pussy. I slowly slid myself in and out of her a few more times while our breathing began to return to normal. Finally, I pulled out of her all the way and some of the cum I shot into Harper’s pussy began to slowly trickle out of her. She reached down and rubbed the cum into her pussy before taking her fingers out and licking them clean.
Harper was a good girl when it came to sex indeed, but I was certain that I could teach her a few more tricks to make her even better. After using one of the washcloths from the kitchen part of set to clean up our mess as good as we could, we went back to my classroom and got dressed.
“That was pretty good, Harper, but I think there is still a LOT more I can teach you. So, I want you to come see me every Friday at the end of the day, but if you need any… help, in between Fridays, here’s my home number and address if you need to come see me.”
Her smile was so bright it could light up a dark room.
“Thanks, Mr. Caan, you’re the best teacher ever.”
She gave me a bear hug and kissed me hard again. I grabbed her ass and squeezed her cheeks with both hands. ‘Next time,’ I thought to myself.
We exited the school and I waved to her dad as Harper got into his car and they drove off. I walked to my car, got in, and started the engine. ‘I have a really good feeling about this year.’
AUTHOR’S NOTE: Please comment with your likes, dislikes, ideas for improvement and anything else that comes to mind. With your help I can make better stories for YOU! I hope you enjoyed it!
