The first day of the last year on my job. [M/F][Age diff][Student/Headmaster]

This is my first post here. Apologies if its kinda long. happy for any feed back.

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Sacred Heart is the one of the best private schools in the city and I have been Headmaster for about 5 years, since I was 40. We have our share of troublemakers and it falls to me to hand out the discipline for both boys and girls. But, only for those that have really become a problem. Normally, its the fringe knuckleheads that just want to be seen as the toughs in a school of softies. I hadn’t had a girl come in, since…well ever, now that I think about it. I guess you could say I was extra surprised when I looked up from my desk and saw Lena standing there with a red demerit slip.

Lena was a senior, and had been at SHS since I got here, but she pretty much kept to herself. Mostly quiet, but popular. She was the type that had a varied group of friends. Jocks from her Field Hockey team, geeks from the academic decathlon team, and the top of the class with the academic crowd. Looking at her, it struck me how pretty she was. Reddish brown hair, sparkly Green eyes, and soft pale skin. She was taller than most of the girls, and even some of the boys. She had been blessed with an amazing body. This year, you could see she had become a healthy young woman. She had killer legs, and curves that wouldn’t quit. But her absolute best asset, was a spectacular set of amazing tits. They sat on the top of her uniform straining at her blouse, and the white material stretched to contain them. I found myself staring at her, with my mouth a bit open, mesmerized.

“Uh, Mr. C?” she said, snapping me out of my trance. “I was told I needed to come see you.” The red demerit is for when she has been sent to the office for the 5th time. “What seems to be the problem, Lena?” I asked her, motioning her to have a seat. As she moved to sit down, I noticed that here School-girl skirt was extremely short. Just barely down passed her pubic area. Her white socks, were pulled up to her knees, and there was about a foot of bare thigh showing. “Well, Sister Catherine just doesn’t like me. She keeps being nit-picky about everything.” She pouted a bit, took a deep breath and I couldn’t help but follow her chest rise and fall. She continued “I don’t get how she thinks she can write me up about my skirt, when its the exact length it has been since last year. She says I am distracting the class. Its not my fault those stupid boys only have sex on the brain!” She sat huffing waiting for me to respond.

I held out my hand and asked for the demerit slip. I was happy to have to read, and not look at her. Sure enough, Sister Catherine had talked to her several times in the past month, and 3 times it was for Skirt too short, and once for making “googly eyes” with another student. One of the boys on the Football team. “Well, Lena” I said. “It seems that she has you pegged as a trouble maker. Looks like she has your skirt as too short” “But, its not!” she snapped. “Watch your tone, young lady! I am not one of your friends, nor one of the other teachers!” “yes, sir” she said softly. “I’m sorry. Its just not fair. These are the same skirts I had last year, and when I measure them, they are within the rules.” Her voice was soft and had a pleading tone. I could tell this might be trouble for me.

The school dress code on skirt length was 4 inches (or less) from the floor, when kneeling, and absolutely no undergarments should be visible. “Well, lets get to the bottom of this” I said, as I dug in my desk for a ruler. “Please kneel in front of my desk” She got up, and took her knees, with her hands on my desk. I stood and walked around, and I could see it was way short. From the back, I could see the the curves of her ass cheeks, covered in a tight boy short panties. They were a solid emerald green, and they matched the plaid in her skirt. I bent over and held the ruler on the floor and we both looked at the measurement, and it was a hair over 8inches. Double the allowed length. “oh wow…” she said softly. “ I swear these are the same from last year. I guess I grew more than I realized” “Yes” I started “you are becoming a very tall young woman” Before I realized it, she popped to her feet. “Wait a minute!” she nearly shouted again. I gave her a look, and she mouthed the word “sorry” silently.

“When I was sitting, my skirt rides up, I think my butt is too big.” She smiled as she tugged her skirt down, and smoothed it out. She knelt in front of me again, and said “ Measure again, please, Sir.” A dangerous smile crawled across her face. I bent over and held the ruler and sure enough, it was 4.25 in.

“Well that’s close” she said. Lena tugged her skirt some more, and she then hit the mark. “See! I told you!!” I couldn’t help but smile. “I guess you are right. But, what about this making faces at boys trying to get their attention?” “Ugh, as if! That’s not true, I don’t want their attention. I can’t help it if they stare at me. I was telling him to stop and she wrote us both up.” I went back to my seat, and motioned her to get up.

“Well you need to be more careful how you interact with them.” I told her. “You are a very beautiful, and you don’t want them to get the wrong ideas. I will let it go this time, but you are a senior. You need to be setting a better example for the other girls.” “Yes, Sir. I will. I promise.” I took her slip and put “2 days after school detention” then handed it back to her. She groaned and gave me a look. “I gotta give you something. Now, you can stay here til lunch. Then you can go back to your classes. I’ll arrange it so that you can do detention, here in the office. And, when you got to Sister Catherine’s class, make sure you smooth your skirt down, and be on your best behavior.” Luckily, it was just a beat, then the lunch bell rang. She got up to leave said “I guess that’s ok. Thanks for not making a big deal about this” and went on her way. I let the admins know she would be back after school to serve her detention in their area.

The rest of the day passed without incident, and when the dismissal bell rang, I walked out to the hall to say good-bye to everyone. Within minutes, the halls were empty and I noticed Lena walking our way. We both waved, and I quickly went into my office. I wanted to avoid her, and I had plenty of reports to work though. After a bit, a knock startled me out of the papers, and Lena was opening the door as I looked up. “Sir, do you mind if I sit in here? They all left the office, and the janitor creeps me out.” Without thinking I motioned her in, and she turned and closed the door behind her. She sat down and I buried my nose in the reports, again.

“Mr. C?” “Yes, Lena?” “I was lying earlier when I said I didn’t want the boys’ attention. I like it when they look at me. I can feel their eyes staring at me when I walk the hall ways. It makes me feel all tingly inside. Like a light switch goes off.” I gulped and shifted in my seat, as my cock decided to wake up and listen to this. She went on, “I am also confused. When they look at me, I can feel my face flush, and my nipples start to get hard. But, earlier today, when you were looking at me, I felt all the same things. But then, I also felt achy. I never feel achy with them.” I stared at her and she leaned forward. “I noticed I get achy when I am around you” “What do you mean?” I quietly asked. “You know.” she whispered softly, and pointed to her skirt. “Down there” even quieter. “My pussy. It gets achy every time you are around me.” She rested her massive tits on my desk and continued. “That’s why I pulled up my skirt in her class. I wanted to see if it would happened again. And it did, it ached as soon as I came in here earlier.” I was dumbfounded and I just gave her a blank look. “And now that I am in here again, its aching so much. I can feel it getting hot. Maybe there is something wrong with me?”

I knew I was done for.“No, not at all. Look at me, there is nothing wrong with you at all. You are just becoming more and more of a woman.” I knew this was borderline, but I justified it. Telling myself that she had turned 18 at the beginning of the school year. I continued. “A woman needs a man to take care of her. Not a boy. Would you like for me to help you?” “Can you help with the achyness? It drives me crazy.” “Well, I think I should take a look, I may know what to do.” I held my hand out and walked her to my side of the desk. I moved the papers away, and I pushed my laptop over to the side. She stood against it, and I ran my hands up her legs, pressing them apart. I could feel the heat coming from between them. In one swift motion, I pulled her panties down, and patted the desk for her to sit.

She sat down and I lifted her feet, up to the desk, and she placed them on the top. Her skirt covered her, but just barely. “Well let me see…It’s ok. I am a professional. We will go slow. And if you ever want to stop, you just say so.” “Yes, Sir.” she said, as she let he knees fall open and lifted her skirt all the way. This exposed me to the most sexy, pouty little virgin pussy. She was wet, and her pussy was glistening. Her hair was trimmed close, nice and neat. It was perfect. “I heard you were an expert.” she said quietly. “Tell me what seems to be the issue” I got close to her, while my hands held her thighs. In the activity, I noticed the buttons on her blouse had come open, and I was staring down at the softest cleavage ever. “It starts to throb, and pulse. I get wet and frothy. Its, I dunno, achy.” “Let’s take a look then.”

I bent down, and inspected this magnificent pussy. I wanted to dive right in, and lap it all up. “I see what you mean. Its very pink and puffy. Have you been touching yourself?” Only when I can’t take it anymore, I know I am not supposed to, but I can’t help it” Slowly, I moved my hands closer her to he pussy. “That’s ok, you can do it, if you don’t have anyone to help you. You mind if I touch you?” She shook her head quietly, and said “Yes, you can.” Softly, I placed my hand on her mound, with my thumbs resting on each side. “I can show you a few things to do, or I can do certain things for you. But it would have to be our secret. Can you keep a secret, Lena?” “Yes! Of course I can Mr. C, anything for you!”

I let my fingers knead the softness on each side of her. I move my hands slightly above, palms down, and slide them down in a soft massage. Each time getting closer and closer to her clit. I repeat the motion, this time stopping with my thumbs gently opening up her flower. I rub each labia between thumb and forefinger, and she moans quietly. I move up again, this time pinching her clit between my two fingers and rub back and forth. “Oh my god, that feels so good. don’t stop that” Her breathing starts to quicken, and I lean forward and kiss her cleavage, so soft and heavy. I steal a kiss from her, my fingers still dancing on her clit. “Would you kiss me down there?” she whispers in my ear, almost begging. I kiss my way down, and kiss her breast again, I pull up her shirt and kiss her soft belly. Then I place my nose between her legs. I take a deep breath in, its intoxicating. I know I have to taste her.

Gently, I lick her on the sides again, and my tongue follows the same path my fingers did. She is moaning the whole time, and she practically yelps when I find her clit. It is straining against the hood, and its a solid a BB. “Oh YES!! Mr. C, don’t stop! Please…” He voice trails off, as her breath escapes her. She I feel her hands on my shoulders, and they pull me toward her. My hands take a thigh in each one, and my thumbs press them wide open. “Oh, my, I am so wet” she gasps. My face is fully buried in her mound, and I am lapping up all that flows. “There you go, let it all out” I work my way back to her clit, and her hands jump to my hair. Grabbing handfuls, I flatten my tongue against her button, and she grinds herself into me. She has lost all control. And is pulling me, and grinding against me harder, and harder. “YES, YES” she yells and then loudly screams. Her hands mashing my face into her in a violent press. I can feel her legs trembling as she comes down from her high. Violently she pushes me away and has the most excited face. Her mouth turning into a smile.

“OH, Mr. C! That. Was. The. Best!!” God I want to taste you now! I want to feel you inside of me!!”

I push back, trying to contain her eagerness, and catch my breath at the same time. Taking in a deep breath, and grabbing her hands from my belt, I stop her. “Time is up. You should get going. Remember you have another detention tomorrow! I have so many things I need to teach you. Same time tomorrow” She got up, hugged me, and went to leave. She waved good-bye, as I showed her her panties, and brought them to my nose to breathe in. I quickly shoved them in my pocket, and she walked out.

Source: reddit.com/r/Erotica/comments/gd2q2b/the_first_day_of_the_last_year_on_my_job_mfage