The Headmaster And The Pupil

The characters in this story are consenting adults. St. Ann's School exists in the imagination of two creative lovers. If you enjoyed reading these characters as much as I enjoyed writing them, please leave suggestions for what you'd like to see them up to next!

*****

-The Headmaster-

"WHAT am I going to do with you, Miss Connolly?"

I sighed heavily as I pushed my chair away from the desk, dropping Sister Catherine's latest write up of Megan Connolly in exasperation. She was one of the most difficult students to deal with at this school. Bright enough, B+'s and A-'s across the board, admired by her peers and truly a sweet girl. The very same one who baked Sister Brigid cookies and brought flowers when her cat died. But, even at 18, she just could not put up with even slightly strict authority figures, as her latest snarky remarks to Sister Catherine, one of our older school instructors, showed. And having met Mr. and Mrs. Connolly, I could see why they sent Megan off to join us every year.

"I could probably charge them double tuition and they'd pay it in a heartbeat," I said aloud, to no one in particular.

I decided to take a walk to clear my head, or maybe find some inspiration as to how to deal with Megan. I walked out into the beautiful Indian summer afternoon, wandering the sprawling campus. Whether by accident or by design, my legs carried me into a small grove in the wooded area at the western edge of the grounds, a beautiful, sleepy, secluded spot I would come to to escape from my office. I doubted most people at St. Ann's even knew about this place, and I was perfectly happy to keep it that way.

When I got close to the grove, I heard an unusual rustling sound. Concerned it might be some kind of animal, I slowed down and crept gently toward the clearing. What I saw made my jaw drop.

-The Pupil-

God, I was so wet. I pawed my left breast as my other hand ran quick, gentle rings on my clit. I needed to get off so badly, yet I was happy to take my time. Not very often I could draw out a masturbation session like this in the dormitory. I'd been to the brink three times now, backing off the precipice each time. Nothing felt quite as good as releasing all that tension after edging myself like this. Sometimes I'd even see how long I could hold out before losing control. My personal best was 15. I shrugged off my blouse and dropped my bra to the ground, giving myself unfettered access to my medium-large, tear drop boobs. I decided to cool myself down some, and stopped rubbing my clit and gave attention to each breast. Four times to the brink of orgasm now, I thought I'd settle in and see if I could break that record. That changed quickly.

"MISS CONNOLLY!"

My eyes flew open as I sat bolt upright, frantically trying to cover my exposed breasts with one arm as I pulled my skirt back down over my groin. Headmaster Duncan stepped into the clearing.

"Just what do you think you're doing??" He asked angrily.

"I-I-I...n-nothing Headmast-"

"Save it. Do you think this is conduct benefitting a St. Ann's lady? I come here to figure out how to deal with your latest back talk and THIS is what I find?

I felt my skin burning hot and tried to stammer out a response.

"Quiet. You know you have to be punished, yes?"

I nodded sheepishly and looked down.

"Stand up, Megan." I looked back up, eyes bulging.

"Stand UP. Don't make me ask again."

I stood up, using my arms to cover my breasts.

"Please," the headmaster said bitingly, "don't feign modesty with me now. What I just saw was anything but modest.

The headmaster's tone was commanding, I wasn't about to argue. I dropped my arms to my sides, averting my eyes.

-The Headmaster-

My eyes drank in her young, lithe body as she stood there trembling slightly. Long, honey blonde hair framed a classically beautiful face, with big blue eyes and the faintest dusting of freckles. She gnawed her big, pouty lower lip and she stared intently into the dirt. Her big, full, pert breasts stood proud on her slim frame. Short, fat, succulent pink nipples capped off each one. Her long torso had a taut, firm belly that led to the low waist of her "regulation" uniform skirt, sitting askew on her hips.

"What were you just doing, Miss Connolly?"

"T-touching myself, Sir."

I nodded. "Sins of the flesh are tempting, at your age. Why were you touching yourself? You're a bad liar Megan, so don't try to pull anything past me."

Her eyes drifted off into memory. "I was with Bobby Riordan, sir."

"And?" I asked sternly.

"We...kissed."

"You're a bad liar Megan, that includes not telling the whole truth."

"He touched my breasts sir." After a beat she added, "Under my bra."

"And what else?"

"He...he wanted to touch me, under my skirt sir. But I stopped him, honest."

"He tried to touch your pussy." The word seemed an electric shock to her. "Let me hear you say it."

"He tried to touch my...pussy."

"Better. It's good to know you have a modicum of self control. Take off your skirt Ms. Connolly."

She froze.

"Take off your skirt Megan, you won't like it if I do it for you."

That hurried her right along. She wiggled her skirt down to the ground and stood in her simple pink lace cheeky style shorts. They were noticeably darker in front.

"Those too. Be quick about it."

Automatically she reached for her waistband before freezing there, seeming to only realize what she was doing at that moment. I closed in on her and touched her for the first time. Getting right up in front of her, I grabbed the hair at the base of her head and held her face close to mine.

"Listen to me. This is how this goes, I tell you to do something, and you do it. You do it quickly, and with a smile on your face. Do you understand?"

-The Pupil-

I nodded quickly as I looked into Headmaster Duncan's smoky eyes. He released my hair and stepped away.

"Now," he said crisply. "Let's try this again. Take off your panties."

This time I followed obediently, lowering my panties to the ground, trying my best to keep my knees tight together as I stepped out of them. When I stood up I felt his eyes snap to the neatly groomed little nest of dark blonde hair on my mound. He circled me slowly, dragging his gaze up and down the length of my body as he spoke, not seeming to mind if I responded or not to his musings.

"Now I've always felt that sins of the flesh should be paid for and purged through the flesh. Don't you agree? It's very important that we control our urges, and not give in to our...more base sides. I'm going to show you what happens to sluts. Should straighten you right out."

I jolted at being called a slut. Headmaster Duncan seemed amused.

"Oooh, not fond of that name are you? Well what would you call it? Letting boys touch those breasts, and enjoying it so much you have to come outside and touch your pussy?"

Again, I took to long to respond, and he stepped quickly around in front of me, grabbed under my chin and forced me to look at him.

"What would you call yourself, Megan?"

"A...a slut, sir."

"Quite right," he said cheerily. "Now as I was saying, of the flesh and through the flesh. You were very aroused, weren't you, my little slut?"

"I am - was, sir." I was shocked at the Freudian slip, but more shocked to realize that it was completely true. If I was wet before, I was positively dripping now.

The Headmaster

I smiled a wolf's grin as she confirmed what I suspected. She was loving this, even if she was timid about it. I circled her again and unfastened my belt. She tensed at the sound of the clasp. Seeing this, I gently touched her shoulder and said "Don't worry dear, I understand."

My hand slid down her arm as I quickly fashioned my belt into two loops to hold her wrists. I secured them both tightly behind her back. Gripping her by the neck, I guided her over to the flat rock on the edge of the clearing. It was just below her waist level, and I pushed her roughly on to it, bending her at the waist. My fingertips traced the curve of her back delicately, finally reaching her plump, firm ass. Without giving her an opportunity to realize what was coming, I smacked her ass. Hard.

She yelped and tried to squirm away. Reacting quickly, I made sure she knew how this was going to happen.

"Ah-ah-ah Miss Connolly," I said as I pressed down on her back, keeping her pinned to the rock. "If you want to prove that you're a good girl, you're going to stay there and take this." Noticing a bright pink hand print on her beautiful porcelain skin, I gently rubbed it as I continued. "You will stay put, keep your ass up for me, and you'll thank me for the spanks." I pushed her feet a little further apart as I prepped for the next spank.

*THWACK* Her ass jiggled deliciously on the impact

"Thank you Sir."

"Mmmm yes you are a quick learner. Excellent."

*THWACK*

"Ohhh yes thank you Sir!"

*THWACK*

On and on I went, giving each beautiful orb of her ass 15 hard smacks, turning each a violent pink. By the end, she was arching her back and pressing her ass to the sky, squirming delightfully. It was almost as if her ass was inviting each strike. When I noticed the sheen of arousal down the inside of her thighs, it was obvious that's exactly what was happening.

-The Pupil-

It didn't make any sense. Each smack of my bottom hurt, burned, and stung like crazy. Every one got worse...and yet... It felt good. Actually, it felt...incredible. Absolutely fucking incredible. Every touch burned through my skin like fire. My nipples cried so desperately for attention that it bordered on painful. The heat and the moisture coming from between my legs was unlike anything I'd ever felt.

After gently rubbing my stinging cheeks, Headmaster Duncan yanked me up and spun me around to face him. I cried out as he suddenly pinched both of my nipples and pulled them away from my breasts. The sensations were overwhelming, and I arched my back to press my breasts closer to his hands. When he asked me his next question, my eyes flew wide and snapped to his.

"Have you ever touched a cock? Remember not to lie to me Miss Connolly."

Sheepishly I nodded.

"Did you suck Bobby's dick?"

"N..no Sir. I rubbed it until he...until he came on me."

"Good girl for being honest."

The headmaster gently guided me to my knees on the soft grass of the clearing.

"Let's see what those pretty lips can do Megan," he said, as he unfastened his trousers. I gasped when his hardness came free.

It was...big. Longish, thick, with a bulbous purple head, he looked as hard as I was wet. He stepped close and laid his length along my cheek. It was heavy, warm, and throbbing. His hand tenderly held my head, and his desire possessed me. I nuzzled his hard cock against my soft cheek a few times, eliciting a breathy sigh from Headmaster Duncan.

Instinct and burning arousal took over next. I lapped the bottom of his shaft a few times, and felt his enjoyment on my tongue. Taking the cue, I slowly, gently dragged a limp tongue and bottom lip up the whole underside of his cock. As I enveloped the head in my moist lips, I tried to remember everything I heard about blowjobs, everything I had seen the few times I saw dirty videos on the internet. When I tickled that spot just under his head, the headmaster positively growled.

-The Headmaster-

My legs nearly crumbled from beneath me when she finally took my head in her mouth. When she fluttered the tip of her tongue on my frenulum, I had to steady myself with one hand on her shoulder.

"Ffffffuck," I rumbled, as I twined my fingers in her long hair. Megan's mouth was incredible. Her big, pouty, moist lips took me in tenderly, passionately, hungrily. She sucked my cock exploratorily, but not timidly. The way she was attuned to my pleasure belied her inexperience with the act. She swept those lips up and down my length, swirling her velvet tongue in circles around my head.

"Are you sure you haven't done this before?" I managed to grunt out.

A muffled "mmmphhhmmmm" shook its way from her mouth to my dick, making my knees tremble yet again. She bobbed her pretty blonde head up and down my throbbing cock, working her tongue around my shaft. Every delicate suck of my electrified head brought me closer and closer to the edge. This dirty little schoolgirl had me more worked up than I had ever been.

I grabbed a fistful of her hair, and Megan immediately responded to my urgency. Seeing her masturbating, the spanking and her response to it, her beautiful, supple young body, and having my cock be the first one she'd ever sucked all conspired against me being able to savor it for too long. She sucked with more intensity, tightening her velvet lips and tongue and around me, sliding my cock in out of my mouth faster and faster.

"Ugh fuck, Megan," I grunted out through clenched teeth. "You love sucking my cock don't you, you little slut?"

She nodded and hummed a moan that pushed me past the brink. I felt my cock tense up, my balls rise, and finally after a few more sucks, I cried out as my orgasm erupted through my body. She kept sucking as I came, keeping my body wracked with ripples of pleasure. I felt two, then three, and four big spurts of cum as I drained into her mouth. She handled the first two without flinching, but couldn't handle the volume of the third and fourth. My cum dribbled out of her patient mouth, past her still active lips, and down onto her chin. I slid myself out of her mouth, a little too sensitive for her eager ministrations, as the last of my orgasm fell onto her heaving, flushed bosom.

Drained and exhausted, I eased myself to the ground in front of Megan.

-The Pupil-

I knelt there, covered in cum and sweat, with a slightly tired mouth, in awe of what I had just done. It was incredible to have the Headmaster so consumed by what I was doing to him, for him. To be so desired. Apparently I hadn't distracted him as much as I had distracted myself, however. His firm hand on my sticky chin startled me out of my reverie.

"Did you swallow?"

Headmaster Duncan's thick cum sat heavily on my tongue. I hadn't even realized that my mouth was still full, in my state of awe. I shook my head.

"Show me," he said, gently squeezing my face. I quickly obliged, showing him my coated tongue.

"Mmmmm good girl. Now swallow it all for me." Gulping down his thick, salty cum, I showed the Headmaster my empty mouth. The glistening mixture of saliva and cum on his softening cock caught my eye. He was...softer than he was while in my mouth, but he wasn't entirely limp, either. In fact, it looked as though he was twitching back to hardness. When my eyes fixed on his cock, it didn't escape his notice.

"You liked that, didn't you, you little slut? Everything...you liked it all. Having someone see you touch yourself, the spanking, sucking me off. You're a horny little bitch, aren't you?"

He was right. I had never been so desperate for an orgasm in my life. My body wasn't shy about it either. My cheeks and neck were flushed bright pink, my nipples were engorged, a deep pink color, demanding attention, and my pussy was swollen and drizzling arousal. Subconsciously my thighs had spread themselves as wide as they could while still keeping me kneeling. The headmaster's eyes didn't fail to notice this.

He smirked and shook his head at me. "I know what you want next."

I trembled at the words. Of course he knew what I wanted.

-The Headmaster-

"I'm going to fuck you, Megan."

"Please, sir," she whispered.

I locked my gaze on hers. "What do you want? Say it louder."

"I...I want you to fuck me Sir. I want it so badly."

"Mmm you need my cock don't you my pet?"

This seemed to put her over the edge, she crawled to me, positively pleading.

"Oh yes Headmaster. I need your cock, I need your cock inside me. Please Sir."

I smiled and adjusted my belt that was binding her wrists, placing them in front of her now. I nudged her shoulders, indicating to her she should lie back on the soft grass. Kneeling between her legs, I knew I needed a little more recovery time before I could give this little minx a proper fucking. Luckily, I had just the thing in mind.

Leaning forward, I kissed her flushed neck as I palmed one of her immaculate breasts. Megan stretched her bound hands up over her head, arching her back to press her firm, hot, sensitive flesh hard into my hand. Venturing down with my lips, I traced a swerving path from the ticklish underside of her right tit, as my hand squeezed her left. In quick succession, I pulled one nipple with my teeth and pinched her other. Megan yelped, giggled, then cooed as she settled back comfortably into the grass, pressing her gorgeous boobs back up at me. Repeating the process a few more times, I had her driving her hips upward at me. I simply had to taste her.

-The Pupil-

The Headmaster kissed his way down the right side of my torso, lingering on my hip bone. Goosebumps rose in anticipation of his lips. I was an earthquake waiting to happen. My hips twitched uncontrollably as he got closer to my desperate pussy. He kissed down to and through my little landing strip, and I moaned loudly, welcoming the glorious next kiss.

It didn't come. His tongue dragged gently up my inner thigh.

A loud, husky, impatient "fuuuuuuuuuuuuck," rumbled out of my throat. I had never seen this side of myself. My hips writhed as I murmured desperate pleas. No boy had ever done this to me before, but I knew that I needed it more than anything. When his moist tongue dragged its way up the length of my wet slit, my breath caught in my throat.

The firm, slow pressure of his tongue on my slickness was delicious. My brain was a web of lightning bolts, my core tensed up so much it almost hurt, and my legs wrapped themselves around his strong shoulders, pulling him deeper into me. There was no stopping this. I was completely out of control of my body, utterly entranced by the Headmaster's tongue. And I fucking loved it.

"Ah...ohhhh god...fuckfuck yes," I moaned and I stammered as the dam broke. I pawed each of my tits as I bucked my hips up at the headmaster. My body went totally rigid and I fell silent for an instant, until the crashes of my orgasm took over. I curled my toes as the tension in my muscles broke and uncontrollable tremors rippled through my body. I couldn't stop myself from screaming out as the climax wracked my body. It felt like it went on forever.

Until I felt a gentle, insistent pressure at my electrified opening.

-The Headmaster-

I couldn't hold back any longer. I couldn't let her have the time to recover. I was going to give her another orgasm, and I'd be damned if I wasn't going along for the ride this time. As Megan slipped into the tail end of her climax, I repositioned and pressed my aching cock at her slit. She regained some of her senses and stared up at me, nodding slightly. I slowly slid myself into her still twitching pussy. She threw her head back and groaned as I filled her with my girth.

"Oh my god, your cock feels so good Sir," she purred as pressed all of myself into her, settling there briefly. Her pussy was molten, electric, squeezing me like the world depended on it. As I started gently thrusting, she winced a little, before moaning her approval. She'd never been stretched like this before, but she was so ready for it.

I started thrusting more steadily now, and her hips rose and fell to blend our rhythms into one. She whimpered urgently as her strong legs wrapped around my waist.

"Fuck, Megan, you hot little slut. You love my cock, don't you?"

"God yes, you feel so good in my tight little pussy. I'm gonna come again"

Hearing this, I sat up, grabbed under both of her legs and pulled her closer to me, picking up my pace and intensity. Her hands flew to her gorgeous tits, massaging them as she groaned louder. Holding onto her hips, I pulled our sizzling cores together in slow, hard strokes.