The Dirty Headmaster

by Cassandra Dee

  I shook my head, smiling. Because yes, I was lucky to be with the headmaster. My friends were right. He was an insanely good therapist, treating my problems with insight and empathy. Bex, Nicole and Sami didn’t even suspect the truth. The thought maybe I had a small crush on him, but nothing more. Nothing that crossed the lines.

  Boy, were my buddies wrong.

  Because Thorn and I crossed the lines all the time.

  We’d burst through every and any boundary.

  There was the physical. I gave my body to him each and every session, bending over and letting him do anything he wanted.

  Whips, chains and dildos?

  Please, that was for beginners. We were at an advanced level now.

  But even more, I’ve let Thorn take my heart. The alpha believes in me. He supports me, telling me to reach for the stars. He wants me to succeed and it’s not just words. It’s the risk he assumes on my behalf.

  He’ll let me use his A/V equipment.

  He’ll give me unfettered access to his laptop.

  He wants me to use his cabin, even when he’s not there, uncaring of who knows or who figures out our dirty secret.

  So yes, any man who’s willing to take on this kind of danger is worth it in my book.

  The only problem?

  Maybe it’s all dreams.

  Maybe I’m just a naïve teen, mooning about the man who gave me my first taste of hard, huge dick.

  Maybe I’m in love with a Dom who makes all his submissives feel like they’re over the moon.

  So the reality of our situation sliced through my imagination like a thief in the night.

  Thorn and I would never have anything more than just plain old fucking. It was insanely good, making my insides go loose. But my heart ached as well, the truth so unbearable.

  So I swallowed heavily, trying to look normal.

  “Gotta go, ladies. It’s time. I’ll see you when I get back.”

  And with that, I was out the door. As usual, my feet almost ran to Thorn’s cabin, heart racing, dying to see him once more. Even worse, my pussy throbbed for the feel of Thorn’s thick cock. My need for him was primal, taking over all my senses.

  And the moment I was in front of the cabin, hesitation flew out the window. There was no knocking. Instead, my hand pushed open the big wooden door, locking it securely once I was inside. Where was my man?

  The room was slightly dim, the only light coming from a small, bedside lamp. A warm glow emanated from the shade, highlighting the huge form.

  Because Thorn stood in front of his bed, his face hidden by shadows. I ran and virtually attacked that big form, missing the feel of his hands on me, his touch and his mouth sucking on mine, his tongue roaming my curves.

  And evidently, the alpha felt the same. Because our mouths collided in a fiery bonfire of lust and passion. Our seven day wait had been long and painful, and the need burst like an inferno, turning us into animals.

  Thorn ripped my jumpsuit open with a ruthless gesture, and sure enough, I was bare underneath, creamy curves already heaving, pink slit wet. The big man loved it, face growing harsh, those blue eyes searing over my white flesh.

  “You’re beautiful, baby girl,” he rasped before lowering his head to bite at my skin. “So gorgeous.”

  And it was on then. Because Thorn didn’t do a warm-up this night. Instead, after laving my breasts and passing one hand between my legs, the big man straightened.

  “You’re wet,” he grunted, taking in that shiny palm. “Fucking soaked.”

  “Yes Master,” I panted needily, more juice gushing between my legs. “All for you, Master.”

  And those blue eyes gleamed once again before the big man strode to the wooden toy boy, pulling something out. The flogger trembled in his hand, each leather strand a tentacle of searing, delicious pain.

  My skin bloomed even though he hadn’t touched me yet.

  “Bend over,” was his growled command.

  And slowly, my creamy curves obeyed. I leaned over in the middle of the cabin until my fingers touched the wooden floor, every inch of my sweet body exposed for his gaze.

  And CRACK!

  It happened.

  A muffled scream escaped my lips, a searing flash of heat and pain lancing across my butt.

  “Oh!” was my cry. “Oh oh!”

  But Thorn didn’t wait. Another sharp crack rang out in the room, the flogger’s leather strips doing their work.

  “OH!” I screamed this time, unable to hold it in. “Oh oh!”

  But Thorn wasn’t done. This time, there was a special surprise because as my thighs tightened, bracing for a third lash, instead something was rammed into my butt.

  My eyes widened and then closed with pleasure, the shock overwhelming. Oh god, oh god! My poor anus! And yet, the headmaster had done his job.

  Because last time, he’d told me to prepare, handing me a big butt plug after our hot session. I’d stared disbelieving, the black rubber at least three inches long and two inches thick.

  “What?” was my gasp, turning wide eyes to the big man. “What am I supposed to do with this?”

  His blue eyes flared even though that bronzed body lay still, humming with release.

  “Put it in yourself before you go to bed, sweetheart,” he rumbled, “Work it into that tiny asshole and things will be easier from here on out.”

  I gaped. Sure, we’d done anal but still. Sleeping with this monster in my butt? What what?

  The alpha smiled lazily again, even as his intense gaze swept my creamy curves.

  “That’s right sweetheart,” he growled. “Next week we’ll be doing some real wrong things back there, and it’ll be easier if you get yourself stretched out. So do it, baby. Stretch out that bottom, otherwise you’re not going to like what comes next.”

  And I’d obeyed. With a trembling hand, I’d locked myself into the restroom late at night, staring at the giant black toy. Oh my god, oh my god. Was I really doing this? Was I really going to ram a giant plug up my anus in preparation for our next hot session?

  But I had to. Thorn had given his orders, and I always obey. So unzipping my jumpsuit, slowly I put one foot on the toilet seat, pulling my g-string to the side and baring my bottom hole.

  Oh god, oh god!

  This was so wrong!

  What kind of slut have I become, pushing a big black toy into my bottom because a man told me to?

  But it was so good too. Closing my eyes, I dreamed of Thorn, that massive, commanding body, his dick dripping with lust before it slammed in home. And slowly, my anus opened a bit, admitting the head of the plug.

  But it was real hard work. I screwed and screwed, trying to get my bottom to loosen, thinking nasty thoughts of Thorn and everything he was going to do to me. I willed my anus to relax, begging my rectal muscles to soften.

  But I couldn’t get it in. And shit, but Nicole almost busted me. My buddy rapped on the door, voice still sleepy even as my butthole twitched from surprise.

  “Minnie! You’ve been in there for hours!” she whined.

  I froze before my voice rang out, pleading.

  “My stomach’s hurting real bad, Nic! Just give me ten!”

  She shuffled away with a grunt, the springs of her bed creaking once more. Good. I’d bought myself some time.

  And closing my eyes, dreaming of Thorn, I did it. My anus relaxed and with a pop and a little squeal, it was in. oh god. I had a big black toy up my bottom, and it felt really good. A little uncomfortable, but it was something I had to live with if I wanted to do hard anal with Thorn.

  I flushed the toilet noisily before coming out, pretending to grip my stomach.

  “I’m done! I’m done!” was my fake moan. “At least for now.”

  Nicole levered herself off the bed, shooting me a dirty look.

  “Gross,” was her flat reply before slamming the bathroom door in my face.

  I grinned in the dark, climbing into the bunk bed. Because my roomie didn’t suspect in the leas
t, and now I had this huge monster in my butt, stretching and pulling, making me squirm in my narrow twin. Oh god, how was I going to fall asleep? How was I going to get any rest with this dirty dildo up my back hole?

  But now it was time for resolution.

  “Get on the bed,” he growled, eyes menacing, that big form hard and muscular. “Hands and knees, ass up, face down.”

  Obediently, I crawled on the bed and in a flash, I was tied to the four poster, every inch of me bare and naked, ready for him to use. Oh god, oh god. My pussy pulsed, clit standing up, begging for his touch. And even more, my anus winked at the big man, dying for it.

  He laughed, watching my brown hole closely.

  “What a slut,” was his grunt. “What a little whore.”

  And I moaned, pressing my face into the mattress with shame. But it was more than that. I was his slut, his little whore to use any way he saw fit.

  “Yes,” I whispered into the sheets, face growing red while wiggling my bottom. “Yes, use my body.”

  And with that, Thorn grinned.

  “Tell me, Minnie, how do you want me today?” he growled languidly, almost like we were having afternoon tea. “How do you want it, pretty baby?”

  And I couldn’t stop the words. I’d been dreaming of this moment non-stop for the last seven days. I’d been aching for him, anticipating this session as my pulse beat heavily, racing to the stars.

  “I want your cock ramming into my pussy hard and fast while your mouth swallows my tits,” I cried. “I want you doing me from behind, my hands against the wall while you fuck me without mercy in my ass. I want you to just fuck me, Thorn, in all the ways that you can think of.”

  His eyes grew darker with desire and lust. The alpha was fully naked in front of me now, his cock hard and stiff, thick and long and inviting. And with no hesitation, he moved close and stuffed my mouth with that huge fuckrod.

  I squealed. I gasped. But there was no mercy.

  “Unnph!” was my helpless moan as the his hot cum hit my tongue. “Ummph!” I gulped like a slut, reveling in the delicious man juice even as my pussy pulsed down below.

  And like a good girl, I began sucking and swallowing like mad. Because this is where I belong. Whipped. Chained to the bed with a big cock choking me. My cheeks bulging as I swallowed hungrily, loving the hard, hot snake in my throat.

  But Thorn gives as good as he gets. Because the alpha leaned over my curvy butt and softly stroked my pussy, ensuring the folds were wet. And then it happened. With his cock down my throat, he thrust a toy into my pussy.

  What?

  Where did he get it?

  Ah!

  I screamed, eyes going wide, voice muffled as my cunt was invaded by something huge, cold and metallic.

  Oh god, oh god!

  It was so wrong, pussy stretched and so fucking full as he pounded away.

  Thorn groaned then, eyes falling closed even as that he stuffed my pussy with the toy.

  “Fuck, your mouth sucks even harder when you’re getting drilled. That’s right, sweetheart, keep going,” he panted.

  Oh shit, I was so close.

  I was ready to burst right there, cheeks filled with cock, pussy filled with that enormous toy.

  But then he pulled out at the last minute, chest and abs tight, fuckpole gleaming with my saliva.

  “Naw, not yet sweetheart,” came that harsh, masculine growl. “Not yet. Did you stretch this pretty anus like I told you too?”

  I gasped, panting and so desperate. I wanted him bad, but there was nothing to do but reply.

  “Yes, Master,” was my obedient mewl. “Yes, I did. I inserted the butt plug every night before falling asleep like you commanded.”

  Those blue eyes gleamed.

  “Good,” he rasped. “Because you’re going to see what preparation does.”

  And Thorn released me from my chains then. I lay on my back, curves heaving, wetness still pooling between my thighs. But the alpha was quick. He reached into the toy box once more, this time coming out with a spreader. It was a two-foot long metal bar that locked on my ankles, forcing my feet apart.

  I’d never felt so vulnerable. Here I was on my back, totally nude, knees and ankles lifted into the air and pried apart with this metal implement. Thorn showed no mercy.

  He pulled me at the edge of the bed and then rammed his dick into my pussy, filling me up with his length and fucking me relentlessly. The surprise was incredible as my walls pulsed around him.

  “Oh god!” was my helpless scream, cunt creaming heavily around his dick. “Oh god, yes!”

  But then the big man did something real nasty and unexpected. He pulled out of my pussy, pushed my knees back so that I rolled up further, and shoved that big dick into my ass.

  “Unnnh!” I screamed, eyes wide, anus rammed so hard. “Unnnh!”

  “That’s right,” the Master growled, eyes like fire as he pounded into my butt. “Good girls take dick in their anuses. Good girls get themselves ready for Daddy’s big dick in their bottoms.”

  And oh shit, but it went overboard then. Thorn rotated between fucking my pussy and ass, doing a few strokes in one before pulling out to shove into the other. He panted, sweat beading on his brow and chest, pummeling hard in both holes as my insides creamed heavily.

  “Oh god,” was my helpless moan, feet spread apart, holes welcoming the hard thrusts. “Oh god.”

  And it happened then. After a few minutes of hard fucking, Thorn’s big dick buried in my behind, the alpha seized my eyes with his, holding me tight.

  “Come for me, Minnie,” was that rough growl.

  And I did.

  With a scream, a clench, and then a wave of incredible spasms, I exploded around that enormous cock in my bottom, milking him tight.

  “Oh Thorn!” were my helpless wails. “Oh Master.”

  And the alpha came apart as well. With a heave, a grunt, and one last deep thrust, the big man exploded into my behind, spurting his man seed into my bottom.

  “Fuck,” he rasped, big hands gripping me tight as that cum gun unloaded, shooting on target. “Fuck fuck fuck.”

  But the Dom is always in charge. Because even mid-spurt, the man took control and pulled back, big cock glistening as it withdrew from my anus. And then in the next second, he was buried deep in my pussy, giving my other hole a dose of that hot seed.

  “Oh!” I cried, pussy and anus clamping in tandem. “Yes yes yes!”

  And that’s how my man filled both my sweet spots. I pulsed, I cried out, and tears literally fell down my cheeks as the headmaster owned my all, filling me with spurt after delicious spurt.

  “Yes,” I moaned again, the cream overflowing, trailing between our bodies, the mark of his love.

  And slowly, we descended from heaven, trembling bodies spent, breath slowing into deep heaves instead of desperate pants. He removed the cuffs from my ankles and I fell down limply, totally flustered. My eyes closed for a moment as that hot cum bubbled inside, leaking. And I loved it. I absolutely loved it.

  But the alpha wasn’t done yet. Because he moved then, sitting up beside me. Languidly, I traced my finger to my anus and stirred a bit, coating it with hot cum. My digit raised to Thorn’s lips, an offering.

  He sucked it, blue eyes bright as they caught mine.

  But then the big man popped off, grinning like a devil.

  “I just spurted my seed onto your ass, sweetheart. And it tasted fucking good, honey, so I’m gonna get it straight from the source.”

  “What?” I asked, breathless.

  “I’m gonna taste it straight from your ass,” he growled, blue eyes intense. “You ready for that?”

  My eyes widened.

  “I’m sorry?” was my breathless whimper. “What?”

  But Thorn moved in a flash.

  Because the big man reached into the toy box once more, and pulled out a set of chains. Oh yeah, I love chains now. They don’t scare me one bit, the clinking, heavy metal strands making my pulse race, my p
ussy pound.

  And with rough hands, he pulled me up and fastened the chains on my hands before dragging me to the middle of the room. There was a hook there. What? Had the hook been there last week? I’d never noticed it before.

  But in one swift movement, it was done. The chains were fastened to the hook on the ceiling, and I stood in the middle of the room, hands over my head, dangling on tippytoes. My creamy curves swayed, cunt and ass dripping with his seed.

  “You’re beautiful,” he growled, eyes roving over every inch of skin. “Absolutely gorgeous.”

  And then the big man got on his knees in back of me.

  “Spread,” was his curt command. “As wide as you can go.”

  It was hard because I was on my toes, arms almost dragged from their sockets. But I tried my best, and then, oh god. His mouth pressed onto my anus, lapping the white and drinking the cream pie. Oh god. It was so disgusting and yet so good too. Too good even. As his tongue stroked my dirty spot, ripples formed in my stomach again, the waves of sensation relentless and unyielding.

  My toes curled as my boobies trembled, and that was it. I fell apart as Thorn lapped at my bottom and cunt, drinking the juices mixed in with his sperm. He pushed his tongue in deep, feeling my sweet hot anal walls clamp down on his mouth.

  “Oh Master,” I screamed helplessly, dangling from the chains as his mouth swept between my legs. “Master yes!”

  And after it was all over, Thorn rose before me. The man was a god, body bronzed and perfect, enormous with every muscle rippling. Even worse, his mouth and chin were smeared with our release, that virile semen bubbly and white, straight from my ass. And the big man just doesn’t stop. Because grasping my chin with a firm hand, the alpha kissed me hard, transferring the dirty snowball to my lips. I swallowed, savoring the heavenly brew, the mixed release of our pleasure.

  “You like it, don’t you?” the alpha growled, eyes blazing as he watched me swallow. “You love it.”

  I nodded, panting heavily, unable to deny the truth.

  “Yes Master. That was amazing. Thank you Master.”

  And nodding with satisfaction, Thorn released me from the chains. Each gesture was gentle, the man catching me as I collapsed, all the blood drained from my limbs. Oh god, oh god. Lovingly, my master carried my limp form to his big king-size, laying me reverently on the soft mattress.