This is a story I previously published here years ago under a different username, holes. I have decided to re-publish a revised version.
This is a work of pure fantasy. If you do not enjoy stories of non-consent / reluctance, please do not read.
All characters are 18 years old or older.
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I drove into the parking lot and took a deep breath as I prepared to get out of the car, apprehensive but excited about my first day at my new job. It was my first day at Bonita Girls' School, where I would be Head Disciplinarian, a position I'd been accepted for at the end of the previous school year. I was particularly looking forward to seeing the principal, Miss Lawson again; she was beautiful, voluptuous, with long dark hair, and for my interview she wore a low-cut top that showed off her ample cleavage. I remember I had trouble not staring, and I swear a couple of times she caught me, and smiled knowingly. Despite the distraction, I must have interviewed well as I was offered the job a few days later.
Just the thought of her had made my cock grow and stiffen, and for a moment I contemplated rubbing one out now in my car so I wouldn't be so distracted for the rest of the day. A glance at my watch, however, revealed I didn't really have time.
I stepped out of the car and walked across the parking lot and through the grand entrance to the school. The corridor was deserted as I made my way towards Miss Lawson's office along the marble floor. As I prepared to knock on her door, I hoped my hard-on had dissipated enough so as not to be visible through my pants.
"Come in," Miss Lawson said, and I opened the door and entered her office. I was thrilled to see she looked just as hot as I'd remembered, again wearing another top with a plunging neckline, and again I could hardly take my eyes away from her heaving breasts.
"Good morning Mr. Johnson. How are you?" she asked.
"Fine thanks. And you?"
"Very well thank you. Please take a seat," she said, ushering me toward the chair opposite her desk. "Did you enjoy your welcome to the school this morning?"
"My welcome? I'm not sure what you mean." I replied, sitting down.
"There wasn't a girl at the entrance this morning to welcome you to the school when you arrived?"
"No..." I said, intrigued by what she was referring to.
"I do apologize. This simply won't do. Excuse me a moment" she said, and pressed the red button next to the microphone on her desk.
"Will Olivia Preston report to my office at once" she said sternly into the microphone. By now I was even more intrigued about what was going on.
"Olivia was supposed to welcome you to the school this morning. She'll be here in just a moment."
"Oh...OK," I replied. There was supposed to be a girl welcoming me to the school when I arrived? What did that mean, exactly?
While waiting for Olivia, we made smalltalk about how we'd spent our respective summers. She told me she'd spent most of the time on the beach, and my head was immediately filled with visions of her in a bikini, rubbing sun tan lotion all over her exposed body. My hard-on started to return and I shifted uncomfortably in my seat.
Less than a minute later, Olivia arrived. She was gorgeous - about 5'5," with shoulder length blonde hair, brown eyes, full lips, and while her breasts were not the biggest they looked very pert under her shirt. She was wearing a ridiculously short skirt which must have barely covered her panties, and they showed off her smooth, tanned legs. I wondered how a skirt that short could be considered part of the school uniform, and I had to stop myself from staring at her legs. By now, my cock was fully hard again and I worried the bulge would show through my pants.
"Olivia, our new Head Disciplinarian, Mr. Johnson, tells me you weren't there to welcome him at 7:30 this morning as we had planned?" Miss Lawson enquired.
"Oh my God, I'm so sorry, I thought it was 8:30!"
"I'm very disappointed in you, Olivia. It was a very simple instruction to be there at 7:30"
"But I'm sure you said 8:30, miss, because..."
"Are you arguing with me?" Miss Lawson said, now raising her voice.
"No miss," Olivia replied meekly.
"Good. Now get over there and give him the welcoming we talked about"
Olivia nodded and walked over to me, smiled and then dropped to her knees. I couldn't be sure what exactly was going on here, but I think I had a good idea. Olivia paused and looked back at Miss Lawson, who nodded her approval back.
Why was she on her knees right next to me? I was sure Olivia would be able to see the bulge in my pants, as my cock felt like it was going to burst out.
"Hi, I'm Olivia, I'm here to welcome you to the school," she said, on her knees and with her hands now on my thighs.
"Hi Olivia," I replied, my heart racing and my cock throbbing with anticipation.
"I'm so sorry I wasn't there to greet you earlier," Olivia said, looking up at me with her big blue eyes and an anxious look on her face, as she reached over and unbuckled my belt. I couldn't believe this was happening.
"That's...that's OK" I replied. Olivia was now unzipping my pants as my ever hardening cock urged to break free.
"Olivia is a senior here," Miss Lawson said. "In fact, she just turned 18 yesterday."
"Thank you for being so understanding," Olivia said as she reached inside my pants, then inside my boxers and deftly wrapped her soft, warm hand around my throbbing member. I was so excited I was afraid I might climax right away. I looked up at Miss Lawson and she smiled back at me. Olivia took my cock in her hand and began to stroke it slowly and gently for about ten seconds.
"I hope this will make up for it," Olivia said as she lowered her mouth onto my cock. Her tongue swirled around my cockhead and she licked up the precum oozing from the tip. The feeling was unbelievable as this hot blonde teenage girl engulfed my cock with her warm, wet mouth. I still couldn't believe it was happening, and for a moment actually considered it might be a dream, but the pleasure coursing through my veins from the amazing blowjob I was receiving from this talented cocksucker was so great and so intense that I realized it had to be real.
"I hope that does make up for Olivia being late this morning, otherwise she'll need to be punished," Miss Lawson said.
I couldn't respond, and shut my eyes and enjoyed Olivia sensuously sucking my throbbing member.
"Will you have to punish me?" Olivia asked about ten seconds later, lifting her mouth off my cock for the first time. A string of drool linked her mouth to my cock as she looked up at me with those innocent, puppy dog eyes.
"No, it's OK" I replied, putting my hand on her head and guiding her back towards my cock, pushing it past her lips and back into her mouth.
"Nonsense," Miss Lawson said. "She's been a very bad girl and needs to be punished immediately,"
"No really..." I pleaded as Olivia went to town on my cock, sucking it like crazy and taking it so deep into her mouth.
"Don't worry, I have a feeling you'll like what I have in mind," Miss Lawson said, rising from her seat. She walked round to my side of the desk, and put her hands in Olivia's hair and slowly lifted her head from my crotch.
"I want you to teach this naughty girl a lesson," she said as she pushed Olivia onto her hands and knees, her ass closest to me. Her skirt was so short I could now see her panties, and didn't have to wait much longer to see a lot more. Miss Lawson pushed up Olivia's skirt and pulled down her panties to reveal her snatch. From where I was sitting she looked completely shaved and it was so inviting I couldn't wait to see what Miss Lawson had in store for us.
"Do you want me to spank her?" I asked, assuming that was Miss Lawson's intention.
"Spank her? I think we're way past that," Miss Lawson replied. "Mr. Johnson, I want you to fuck some sense into this girl!"
Olivia looked back at me, pleading with her eyes, and I felt sympathy for this girl who seconds earlier had been giving me an amazing blowjob. But I looked at Miss Lawson and I could tell from her expression that she would be very disappointed if she didn't do as she asked; I was Head Disciplinarian after all. And if this was Miss Lawson's idea of discipline, I felt I was going to be very happy working here. I got down on my knees right behind Olivia and held her ass with my left hand as I guided my cock towards her pussy with my right hand, the head of my cock touching her snatch, my precum mingling with her pussy juices. I couldn't hold back any longer. Olivia gasped as I suddenly thrust my entire cock past her pussy lips and deep inside her her hot, juicy snatch. I couldn't believe how tight and wet she was, and before I knew it, I forgot myself and was really going at it, pounding Olivia's tight teenage fuckhole. Since she was dripping wet, I figured Olivia must have wanted it so I no longer had any reservations about fucking the hell out of her. Olivia moaned and gasped as I filled her to the brim with my member, and it often felt as if the head of my cock reached the very deepest part of her snatch. I relentlessly thrust my cock in and out of her for about a minute before Miss Lawson said something.
"Olivia, which hole is he fucking you in?" she asked.
"My...pussy...oh fuck" she moaned.
"Perhaps I didn't make myself clear," Miss Lawson said, and I paused fucking Olivia to look up at her. "Olivia's been a very bad girl and needs to be punished appropriately. I want you to put your big, hard cock in her tight little asshole"
"Her..." I couldn't even finish the sentence.
"Not my asshole, please!" Olivia pleaded.
"How dare you talk back to me! I was going to ask him to be gentle with you but it's clear you need a more severe punishment." She turned to me and said, "I want you to ravage her asshole"
"Please no!" Olivia begged, but I was horny as hell and eager to both please Miss Lawson and take this opportunity.
"You heard what Miss Lawson said. You've been a bad girl and need to be punished," I said, hardly able to believe the words coming out of my mouth. My heart raced with anticipation, and I slowly pulled my cock out of her, a trail of precum and pussy juices linking my cockhead to her pussy. I put my hands on her perfectly pert ass cheeks and gently spread them, revealing her little starfish, and I practically drooled at the thought of penetrating it in a few seconds. First, I slid my cock between her ass cheeks as if I were lining it up, causing Olivia to gasp. Now I was ready, whether Olivia liked it or not, and gently prodded her asshole with the head of my cock.
"Oh my God...oh fuck," Olivia moaned as I slowly pushed my cockhead past her sphincter and inside her, stretching her asshole. Her hole was incredibly tight, fitting so snugly around the head of my cock that I wondered if I'd be able to push the rest of it inside her. Her ass was even hotter than her pussy, and already my cock was throbbing. The feeling was so good and intense I would have been happy to keep it there, but no way was I going to pass up this opportunity. My cock was dripping wet with Olivia's pussy juices and I used that as lubrication, very slowly pushing my cock inside her incredibly tight hole. Olivia's groans grew louder the deeper I pushed inside her.
