The Headmaster's Office 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I tried stroking downwards, but I had to release all of the pressure because of the friction. I reached for the gel again, but he stopped me and moved my hand all the way down to the base. "Start there and try again," he advised.

This time when I stroked back towards the tip, the skin came with me, sliding over the hardness beneath like silk sheets over steel. It was amazing! All of the bumps and contours were beneath the skin and I could feel them running across my palm, yet my hand stayed in contact with the same handful of skin. This was so not like a dildo.

He reached down for my other hand and cupped it around his balls. "Remember how I said 'anything goes'? Well, not there it doesn't. Gently does it with those guys." I didn't think he meant 'do nothing', but I wasn't exactly sure what I should do with them. Rub them? Juggle them? I gave them a gentle squeeze and he nodded. Right choice! Good one, Belinda!

I leaned forward and licked around his knob as I stroked, relishing the taste of the salty pre-cum that I milked from the tip. I opened wide and took the head into my mouth, running my tongue around the ridge of his knob and wondering if I should be doing anything else. He was looking down at me, enjoying watching me explore, but I could tell that I wasn't progressing him along.

I moved him deeper into my mouth, my jaws yawning around his thick shaft. I nearly had him in the back of my throat when he stopped me, holding my head still with his hands.

"No. Felatio is not about swallowing," he instructed. "There's nothing sexy about a girl gagging on a dick. Don't try and take it all at once, just get a mouthful and alternate pressure, suction and movement."

Oh, was he in for a surprise. Another game the girls play is Deep Throat. By now, you probably think all dorm girls are sluts, but most of us are technical virgins; we just love to explore our own sexuality. Deep Throat is not a complex game: you spray a blob of whipped cream onto the shaft of a dildo and then try to lick it off ... but the tip mustn't leave your mouth. The further away you put the cream, the further into your mouth the dildo goes.

I lost badly on my first few goes and nearly blew chunks all over the bed, but I practiced controlling my gag reflex and now it's practically non-existent. My personal best using -- you guessed it -- Long John Silver the famous double-ended donger is 13 inches straight down my throat. I held it there for 5 seconds licking off the cream and brought it all back out in one smooth action.

I did appreciate Mr Gallows' fellatio lesion -- I was very much a beginner -- but boy was I going to teach him a lesson too.

I took the suggested mouthful and applied pressure with my tongue, then sucking hard I pulled him all the way out except for the knob and sucked him back in again. That seemed to work. He was running his fingers through my hair and I could feel him shaking a little. I wrapped one hand around the base of his cock and gently massaged his balls with the other, all the while sucking and releasing, stroking him in and out of my mouth.

I could hear his breathing quicken and he tightened his hold on my head. The muscles of his legs were standing out and I could tell he was trying to prolong his orgasm. Here we go! I let go of his shaft and reached behind with one hand to grab his buttocks. Then, before he could stop me, I took a deep breath, moved his knob to the back of my throat and swallowed, pulling him towards me. All nine inches slid cleanly through my lips and down my throat, helped along by the natural downward curve of his cock.

With my mouth now pressed hard against his groin, I snaked out my tongue and bringing his balls closer with the hand cupping them, I licked them mercilessly while I swallowed, closing my throat down hard over his bulging knob.

"Oh Holy Christ," he yelled. His hands locked on my head, pressing even harder into me as I felt his balls contract beneath my fingers and tongue. Then with one gigantic throb, he unloaded down my throat. I could feel the cum streaming though the underside of his cock down the length of my tongue as what felt like a gallon emptied straight into my stomach without even having to swallow.

I pushed away, inch after gorgeous inch sliding out between my lips. The tip cleared my throat and I inhaled deeply though my nose as the final five inches slid across my tongue leaving a trail of cream that tasted nothing like what we use in the dorm. I kept the end between my lips, sucking deeply and milking the final drops as the last spasms pulsed though his balls.

When he was empty, I lay back in the chair and smiled up at him standing between my open knees, gaping at me with a stunned expression. I rubbed my wanton slit and beckoned to him: "Now put it in here," I demanded.

Chapter 5 (Mf/Bigcock/First Time/Creampie)

His shock turned to confusion. "It doesn't work like that," he said. Then his face darkened in concern. "Have you never been with a man?"

I shook my head, "Uh uh."

"Oh my God! But you're not a virgin, I know that from lunchtime," he said with genuine concern. "Belinda, you need to give it time. I can't just make it pop back up again."

I looked down at his cock, which was now softening and drooping. How could I not know this? I felt a little embarrassed and every bit as deflated as he looked. I wanted that magnificent cock in my pussy and now I couldn't even jam it in with a shoe-horn. Would I never get the fucking I so richly deserved?

My disappointment must have showed on my face. "It's going to be all right" he soothed me. "Give me twenty minutes, thirty tops." He lifted me effortlessly onto the low credenza beside his desk so that we were standing face to face again. "We just need something else to amuse us while we wait," he said gently kissing my pouting lips.

Reassured, I open my mouth to kiss him back, tilting my head to the side. His rough five o'clock shadow scraped against my cheek. Ouch! Beard burn! Not on my watch, mister!

"You just nominated yourself for my twenty minutes of amusement, Sir," I said with a smile, reaching for the shaving gel and a fresh razor.

"Whoa! No way!" he held me at bay. Tomorrow's a school day and I can't come to work looking like Freddy Krueger!" Seeing my frown at a 1980's pop-culture reference (I had to Google it -- a rare miss for me -- I love the classics), he explained, "Hideous scarring. Bad look."

"Bullshit," I retorted. "Feel my legs and tell me I don't know how to shave. Besides: fair's fair. You shaved me!"

He face started to soften as he ran his hands down my taut thighs and smooth calves, then back up again, moving on to mould my tiny round bottom, narrow waist and heavy breasts.

"I don't shave my tits and arse," I said flatly. "You're stalling," giving him a forceful stare that I never thought I could muster for any member of the faculty, let alone the Headmaster.

"You're right" he sighed, moving close to kiss me softly. "Trust is very important, especially for us. You trust me, don't you?"

I looked down between us. "Given the damage you could do with that thing, and where I'm planning to put it when I get some wood back into it, I'd say I'm marginally ahead on trust points, wouldn't you?"

"You make a strong argument. Do you do Debate?" I ignored this and pumped some more gel into my hands then massaged it into his stubble. Despite my confident insistence, I could see that his face had a lot more angles and contours than my legs, so I started slowly on what seemed like an easy bit: his sideburns and cheeks.

He had both hands on the rise of my hips where they narrow in to my slim waist and was closely watching my bobbing breasts as I worked on his beard. I was just moving on to his chin when I felt a light touch on my bottom, right in the middle where my thighs meet and distractingly close to my vagina. It was his penis, semi-erect and bobbing up and down between my open legs. With each strong flex, it stood up straight, and almost at its full nine inches again, it was long enough for the tip to scrape the underside of my bottom while I was standing on the credenza. Hmm, he was ahead of schedule, I'll take that as a compliment. I paused for a moment and then continued shaving. The touch came again in the same place, twice this time with a couple of seconds between. His mouth was still but he was smiling with his eyes. I looked threateningly back at him.

"That's very distracting," I admonished, brandishing the razor. "If you don't find something else to do with it while I finish this, you could get cut."

"He reached down and grabbed his stiffening manhood. Bending slightly for clearance, he pulled it forwards and nestled the tip just inside the moist lips of my vagina. As he straightened up again, his cockhead pressed insistently at my entrance without pushing inside.

My resolve started to melt away and I nearly surrendered the little role-reversal game we had been playing, wanting desperately to just unlock my knees and impale myself on his gigantic cock. He moved his hands back onto my hips and looked into my eyes questioningly. I recognised this as another gambit in the game, testing my resolve to delayed gratification, which was swiftly running out.

I steeled myself again and took up my assumed role. "Really?" I cocked one blonde eyebrow. "I have a razor to your throat and you're going to leave 'It' there?"

"Yep," he grinned merrily, flexing his shaft and making the knob bulge, opening my pussy by an imperceptible margin.

"Yes, Ma'am," I growled back at him, tightening my pelvic floor. My inner lips closed tightly over his cockhead and squeezed until it slid back from whence it came.

He gasped with the friction and pressure and then croaked "Yes, Ma'am."

My legs felt like jelly but I wasn't going to let him see how close I was to giving it away. I moved in until my nose was directly in front of his and my nipples brushed his chest. "Yes, Ma'am, what?" I hissed.

He straightened his shoulders and looked at me seriously. "Yes, Ma'am. I am going to leave my cock in your vagina. Just for the moment Ma'am, until you can find a better use for it."

I giggled, breaking the mock tension. "Very well," I smiled and went back to work with the razor. Each time I stopped to clean the blade and it was safely away from his face, he would flex his cock, to which I would respond by bearing down on my pelvic wall, crushing it in retaliation. With each exchange, he gradually reattained his full length and hardness, and with veins bulging, he opened me up and pressed into me bit by tiny bit.

By the time I finished shaving his face, his entire knob was inside me and technically, I suppose, we were fucking. My heart was racing because the time had finally arrived, the moment I had dreamed of ever since the disaster with Brad, my first cock. I didn't know what to do next, but since I had gone through so much to remove his stubble I kissed him, gently at first and then more insistently as I moved into his embrace, wrapping my arms around his neck and crushing my breasts into his heavily muscled chest.

He broke our kiss and breathed into my ear, "Quid pro quo, Belinda. Do you trust me not to hurt you?"

"Yes. Yes." I gasped, struggling for breath. "Just please be gentle." I was frightened now and a few tears were welling in my eyes. It was as though I could feel the gravitational pull of his cock, the inch inside me, and the eight below that. The base of his massive rod was so far away; I imagined it driving up into me, knowing it would reach nearly to my ribs, but also knowing that was impossible.

Holding tight he stepped back, pulling my feet off the credenza. I locked my arms and legs around him in panic, his cockhead still inside me. "Christ, what are doing?" I cried. "Don't let me fall!" I was sobbing openly now and pressing my face into his neck.

"Shhhh." He soothed. "Trust me. I promise I won't hurt you." I stopped sobbing but the tears were still coming as I clung to him. He arranged his massive hands around my ribs -- thumbs just beneath my breasts -- and lifted me a little. "I've got you," he said gently. "Now let go slowly and I will hold you. I promise."

I unlocked my ankles from behind is back and allowed my legs to drop either side his cock. I felt him take up the extra weight with his hands. Sniffing back the last of the tears, I pulled my head back and looked up into his solemn eyes. "Go ahead," ne nodded. "Let yourself go."

I opened my arms, releasing him as he took my full weight in his hands. I thought it would hurt, but it was actually really snug and comfortable -- kind of like being suspended in a skydiving harness.

I was now hanging in mid-air nearly a foot and half off the floor, the first of nine inches of iron hard cock pushing into my desperate vagina ... and utterly helpless to do anything about it.

I wiped the tears from my cheeks and craned my neck forward to kiss him again, but he held me tantalizingly out of reach. I smiled; it's going to be like that, is it? Okay, so you're in charge again. What now?

Ever so slowly, he braced his elbows at his midriff and raised me up until the tip of his cock almost slipped out, but still held in the entrance, enveloped by my open lips. Without pause, he lowered me down again, giving just the one inch back. Repeating these tiny movements, he started to build up the tempo, using my body to perform micro bicep curls. In spite of my desperation for more of him, I felt a baking heat building inside my sex.

On the next downward stroke, he dropped me three inches instead of just one. The feeling was like a micro-orgasm! His cock, cool on the surface from exposure to the air, hit the molten core of my womanhood like ice meeting fire. It set off ripples of contraction down my vaginal walls, clamping onto his rigid member with involuntarily spasms. He drew a gasping breath and quickly lifted me up, holding still with just the tip of his erection inside me and straining with the effort to suppress his mounting orgasm.

"You okay," I asked.

"I will be," he answered through clenched teeth. "My God, I've never felt anything so hot ... or so tight!" he marvelled. "I almost have to push you down onto me."

"I can't help it," I said. "I'm just a small package." Reaching down to grip his shaft nestled between my thighs I leaned in to whisper in his ear, "And this is a 'good thing'. You know what they do in small packages, right"

Getting his rhythm back, he lowered and lifted my body, fucking me slowly with just the tip again, but giving me a little extra with every few strokes. Once we were both used to the pressure and friction he maintained that depth -- about three inches -- for a dozen slow, delectable strokes. Oh Christ! Every nerve ending in my body was tingling! I threw my head back and moaned with pleasure, my breasts thrust out before his downturned face.

I pleaded with him, "Please, Sir, I want some more." I didn't realise the literary reference at the time -- it was completely accidental -- but he laughed, breaking the tension.

"Dickens!" he cried happily. "And Oliver Twist not even on our reading list. Well done, Belinda." Then he looked at me with a sparkle, "Do you have any other quotes pursuant to the situation? Something from Led Zeppelin, perhaps."

Sprung! My initial reaction was panic; we were in trouble for singing about the Headmaster. Then reality kicked in and I remembered that the Headmaster had me suspended in mid-air, impaled on the first third of his nine-inch cock.

"But how...?" I began, blinking with confusion.

"The senior girls' dorm is directly above the staff lounge," he explained. "I was in there grabbing a few hours' sleep after I stayed late to prepare for the final assembly last year."

A little chagrined, I started singing in my light, musical soprano, watching for his reaction. "Hangman, hangman, upon your face a smile. Pray tell me that I'm free to ride, ride for many mile."

Then he joined in. "Your brother brought me silver. Your sister warmed my soul. But now I laugh and pull so hard and see you swinging on the Gallows Pole."

We laughed together. "Literature classics, rock 'n' roll," he said. "Any more surprises?"

We had both been teetering on the edge of orgasm and I recognised this for what it was: a way to prolong the pleasure that neither of us wanted to end. But I was also close to my breaking point with tears of frustration and need welling in my eyes. I sung again, softly and in tune at first. "I want it all, I want it all," and then building up to a husky growl that I hoped was reminiscent of Freddie Mercury, "I want it all, and I want it now!"

He shot back, "You can't handle it all," in an eerie Jack Nicholson impersonation.

It was too much for me and the tears came again. I embraced him and buried my face in his neck. Whispering to mask the emotion in my voice I told him, "I know I can't. I want all of you and I know I can't have it. But I want you deep inside me, as deep as you can go, and I don't want to stop again. Please."

"Shhhh," he soothed. "That's what I want too. Loosen your arms." I let go and he continued to bear my weight effortlessly in his hands. "Tell me when I get there," he said, lowering me oh-so-deliciously-slowly onto his cock, pausing as spasms of pure pleasure rippled through my sex.

"More," I panted. "A little more ..." Then as he touched against my cervix, "Right there! I can take a little more, but you'll have to stretch me." He had about six inches inside me now and started gently probing in and out at my depths, working against the resistance. There was a little pain, but mostly it was just an intense pleasure of fullness that I have never experienced with a dildo. I felt down at our nexus with my hand and realised with disappointment that there was still almost two inches to go, but I was full and the pain was starting to override the pleasure.

"Stop" I breathed. "I can't ... just finish me. I can't take any more though."

At my command, he raised me up almost to the point of exit and swept me breathlessly back down, seven inches of iron plunging straight up into my core. Again and again, pleasure exploding in my vagina with the glorious friction and never once passing the point of pain where I had stopped him earlier.

This time I felt the orgasm begin in my thighs, spilling from my loins down my legs, up into my tummy and the depths of my vagina, all spinning and burning together in a ball of naked flame. Then with the speed of a gasoline fire, that ball of energy ripped through my body, expelling a scream of lust and desire from my lungs.

My body lost all control; my back arched and my legs clamped together like a vice over the base of his cock. The entire nine inches now trapped in my flesh so completely that it felt as though it was all inside me.

Now thrumming like a teakettle as my climax convulsed out of control, I held him, helpless to move in the grip of my vagina and crushing thighs, just as he held me helpless in his powerful hands. His body rocked back, muscles bursting from his arms, chest and shoulders as his own orgasm followed mine. I felt his cock yield a little to my pressure as his climax commenced and then a moment later it bucked and throbbed and jetted load after load of cum deep inside me, filling me with pressure until I thought I would burst before it washed back over his cock and poured down my thighs.

That release triggered a second orgasm. Screaming again with the unbearable pleasure, I hooked my heels behind his buttocks and pulled in with all my strength, forcing his manhood deeper inside to fill the space created by his explosive stream. With the exquisite pain of his pulsing knob driving into me, a third crescendo rocked my body, this time my own gushing ejaculation mixed with his and washed over his balls, now pressed achingly against my incandescent labia.