“Let’s see...” the headmistress said, as she pulled a sheet of paper from the manila envelope in her hand. “Who gets to squirt a nasty load of cum for me this week?”
I stood at attention, nervously waiting, naked and sporting a rigid boner. The other five boys standing in a line facing the headmistress were also naked, all of them with stiff erections as well. Seconds after Nurse Reynolds had used her key to remove the vile chastity device from around my genitals, my cock had swelled and stiffened in response. It was the natural reaction to having our cocks released from the restrictive cages we were forced to wear day and night. As much as I wanted to try and conceal the shameful display, I’d learned to keep my hands clasped behind my back.
This was my first year attending Loxford Academy for Boys, a boarding school designed to prep eighteen and nineteen year olds for acceptance into distinguished colleges and universities. The fall term had started just three weeks before. The other boys I shared a room with all looked mortified to some degree, but it was easy to pick out the other two lads who were new to the school. They both still wore the same expression of stunned disbelief that I did, as if not quite sure any of this could really be happening.
“This is unusual, ” the headmistress said, as she scanned the sheet of paper. “It appears as if the majority of you were actually paying attention during your classes this week.”
She was tall and slender her raven black hair pulled back into a tight bun, a pair of narrow rimmed glasses perched on the end of her sharp nose. She drummed the top of the desk she stood beside with the fingers of her free hand, as if anxious to pick up the wicked cherry wood paddle that lay just a few inches away. The paper in her hand listed the scores we’d each received on homework and exams during the week from the various classes we attended Monday through Saturday. Today was Sunday, so it was time for her to determine who would be rewarded with an orgasm and who would be punished with a spanking.
“Four of you have earned rewards this week, ” she stated, looking up at us over the rims of her glasses, “Mr. Weber, Mr. Frost, Mr. Greene, and Mr. Ross.”
Four of the boys along the line gave audible sighs of relief, but unfortunately I was not among them. As distracting as life at the school was, I struggled to keep focused in class, even though I knew the consequences of unsatisfactory grades. Anyone with an 8.5 GPA average or higher in their combined classes for the week was rewarded. Anyone with a combined GPA of 7.8 or lower was punished. I wasn’t getting rewarded, so now I just needed to find out if I was about to be viciously spanked or if I’d managed to score above 7.8.
“Mr. Thompson, ” the headmistress looked directly at the student at the far left end of the line. “Apparently you were sleeping during classes this week... again. You scored a pathetic six-point-seven, even worse than last week. Clearly standard punishments aren’t effective with you, so we’ll be trying something a bit different this evening.”
The gangly redhead stared despairingly at the floor, his eyes welling with tears, as the headmistress turned her attention to me.
“You, on the other hand, scored an eight-point-four nine, ” she said.
I was relieved to hear I’d avoided punishment, but then almost instantly felt frustrated that I’d missed my reward by such a miniscule amount.
“But since this is only your third week at Loxford, ” she continued. “I’m tempted to make an exception and round your score up to eight-point-five.” I felt elated, the previous Sunday I’d had my bottom paddled as punishment, so I’d dreaded the thought of having to go another full seven days without orgasmic relief. “However, ” she continued. “If I do allow you to cum along with your dorm mates, there will be a condition.” She gave a thin ominous smile. “Would you like to know what it is?”
I wasn’t sure I did, but I nodded anyway and muttered, “Yes Ma’am.”
“All my good boys this week are going to rub out nice big loads for me, ” she said. “The punishment for Mr. Thompson, my naughty boy for the week, is that he’ll have to kneel on the floor with his jaw open wide, as all the good boy’s squirt their nasty cum into his mouth.” Thompson’s face went pale. “Now, if you want to join the good boys today, ” she said to me. “You’re going to first have to lick each of their dirty ass holes while they ejaculate. Is that something you’re willing to do, for the chance to squirt a load of your own?”
My pulse pounded in my ears. I sensed the guys stealing glances over at me, waiting to hear my decision. My first instinct was to blurt out an adamant no, the prospect of licking a guy’s ass hole sending me into a near panic. Nothing could be worse, except for maybe having to swallow a bunch of guys’ cum. The way my tight swollen balls ached and throbbed forced me to reluctantly add a second possible option. Like being forced to endure another long week of having my cock locked in chastity, until my balls were nearly bursting with twenty-one days of unspent cum.
“Should I take your silence as a no, you don’t wish to take me up on my offer?” the headmistress asked.
I had no idea how I was going to answer until I heard the word “No!” pass my lips.
“No, I shouldn’t take your silence as a no, or no, you’re not interested in taking me up on my offer to let you be a good boy this week?” she asked.
“N-no you... you shouldn’t think my silence is a no, ” I stammered, my face flushed a bright red. “I... I want to be a good boy this week Ma’am.”
“And what are you going to do to earn such a privilege?” she pushed me.
My face and neck somehow burned even hotter with shameful embarrassment. “I’m... I’m going to lick their ass holes while they jerk off into Thompson’s mouth Ma’am.”
I’m not sure which, but one of the guys stifled a nervous snigger, probably wondering what he’d decide if given the same choice. The headmistress lifted a thin critical brow as she studied her charges, but didn’t pursue the matter. Instead she ordered poor Thompson to drop down to his knees. For a moment it looked as if he was going to dare to defy her, but then he came to his senses. Resisting the headmistress wouldn’t gain him anything. In fact, it would come with considerable cost. He’d still have to suffer the degradation of getting several loads of cum squirted down his throat. He’d just have to endure it with the addition of a freshly blistered bottom.
Once the mortified redhead was down on his knees, Alex Webber was instructed to step up before him. Alex looked embarrassed, but not nearly to the same extent as Thompson. He was also considerably aroused, as evidence by the way the head of his swollen cock throbbed just inches from his dorm mate’s upturned face.
“Nurse Reynolds, I’ll need your assistance, ” the headmistress said. “Please keep Mr. Webber’s buttocks spread wide, so his anus remains fully accessible.”
I’m not very good at guessing ages, but the headmistress had to be at least forty, while Nurse Reynolds couldn’t have been any older than twenty-two or three. She looked captivating in her starched white uniform, the front of which was stretched delightfully taut across her ample bosom. Brownish-blonde hair spilled out from beneath the white cap perched atop her head, a long strand hanging down across her left cheek, as she moved towards Webber with a smirk. A moment later she stood beside him, reaching down to grip the pale plump moons of his ass and spread them wide.
What happened next felt like a dream. It was as if I were suddenly sitting on the sidelines watching someone else, while at the same time still the someone I was watching. I knew what was happening and knew I was the one doing it, but it was easier to pretend it was all happening to a stranger. I had to, in case I ended up not being able to live with what I was willing to do just so I’d be allowed to jerk off onto some guy’s face.
Yes, I was thoroughly disgusted by first the stench of sweat and shit, and then the taste. But I’m ashamed to admit, I got used to it, at least to the point where I almost forgot about it by the time the guy who’s anus I was tonguing bucked and jerked and spewed his sticky load into Thompson’s gaping mouth. But then I received a stark reminder, when I had to get used to the unique stink rising up from between the next guy’s ass crack.
My mortification was compounded by the presence of Nurse Reynolds, leaning in so close to part a pair of pale meaty buttocks that she could clearly see my face, as she urged me to worm my warm wet tongue ever deeper into my subject’s nasty hole. I desperately craved her approval � I suspect almost all the boys at the school did as well � and dreaded the thought that she’d see me as less than a man for tonguing a guy’s ass. But it wasn’t long before I realized her main reaction was growing arousal, as she urged me to help make the guys cum as hard as possible.
And I’m certain I did. I could tell from the way they’d shudder and squirm when I first started to lick and lap across their puckered hole and how tight their anus squeezed around my inserted tongue when they stroked rivers of creamy hot spunk into Thompson’s mouth and all across his face. Nurse Reynolds leered with delight at how successful my efforts were, and as much as I hate to admit it, knowing that my mouth had provided such pleasure had caused my rigid cock to throb with aching intensity.
After Garret Greene, a strapping black lad with a sausage of a cock, finished pumping a fourth milky load of cum down Thompson’s throat, the headmistress finally pulled my face back from between the fleshy moons of his ass and allowed me to stand. She leaned close and gave a sniff them wrinkled her nose at the stench of ass emanating from my saliva smeared face.
“Was it worth it?” she asked with a smirk. “Will squirting your nasty ball-juice be a big enough reward for turning yourself into a perverted licker of boys’ buttholes?”
“I... I hope so Ma’am, ” I stammered and she laughed.
“Well, you’ve earned it, ” she said and motioned for me to take my place before Thompson’s abased form. “You did a very diligent job. You may begin, as soon as Nurse Reynolds is in position.”
Much to my shock and delight, the cute blonde knelt down behind me and reached up to part the plump moons of my ass. I shuddered at the feel of her hot breath along my exposed crack then loudly gasped, as she slid her pink tongue across my twitching anus. I wish it could have lasted forever, but when the headmistress urged me to start tugging on my turgid boner and the nurse wormed her tongue deep inside my tingling hole, nothing could have kept the flood of stored up cum in by balls from erupting from the tip of my cock in one powerful squirt after another.
I’d never ejaculated with such intensity before in my life, nor had I ever produced such a vast volume of thick slimy goo. I won’t pretend like I spurted all of it directly into Thompson’s gaping maw. A great deal splattered across his nose, cheeks, and chin. But the headmistress used her finger to make certain she scraped every last drop of the spunk adorning his face into his mouth, so he could swallow every last dribble and speck, all while ignoring his sobs of shame.
The rest of us lined up in front of Nurse Reynolds, waiting for her to wipe off our genitals with a wet cloth. She then locked our cocks back up in their chastity cages, so we could get dressed and return to our dorm room to finish up any homework we might have before Monday morning classes.
All of us were determined to improve our grades in the week ahead, otherwise next Sunday we might not be rewarded again as good boys.
END