Compensatory session with the headmaster


A short novel by anonymous.


“That was too close, that time, son.” 
The hands steadied on Bobby’s shoulders as the naked teen gripped his balls to fight back the pending orgasm once again. For the better part of an hour now, he had been edging for the pleasure of the headmaster, and the kinky story he was caught up in was too good, almost too real, not to shoot his load. The kid was excited with the older man’s sexually charged narrative about life at the all-boys school. Earlier that morning, Bobby was caught in bed nakedly dry-humping against one of the students in the younger grades. He couldn’t have resisted the boy’s advances and was intrigued at the seductive skills of the young teenager who had climbed in through his dorm room window and directly into his bed. 


Headmaster was now weaving and even more erotic version of the innocent experimentation as he coaxed a confession from Bobby and embellished the tale of two naked boys who simply had a case of the morning hornies. Secluded in this private office, Bobby felt his dick once again lurching as he stopped to prevent cum from spurting all over his nudity. As he wantonly displayed himself sexually on the leather couch where so many fresh-faced boys in suits had sat with their parents for entry interviews, Bobby understood how good the headmaster was at engaging each boy in conversation. Now, Bobby was experiencing an intimacy with the soft seductive tones and suggestive words that once again had almost urged him to the brink of orgasm. 

“Think of some of your classmates you see naked in the showers, Bobby. I’m sure you notice their cocks and thought that many of them might be in naked play with others. Well, I can assure you that I’ve had those boys right here with me just as naked and horny as you are, and they tell me fantasies about sucking your cock, Bobby. Can you imagine those twins from fifth form you’ve been perving? Kneeling in the showers, dick-kissing your penis between their sucking lips, licking and tonguing the pleasure spot just underneath and behind your swollen dick head? Would you like to have them show you how much they love cock-sucking the older boys just so they can taste their sperm? Now, cum for me, young man. Shoot your hot juices as you voice your forbidden pleasures about your classmates.”

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  1. “That was too close, that time, son.” The hands steadied on Bobby’s shoulders as the naked teen gripped his balls to fight back the pending orgasm once again. For the better part of an hour now, he had been edging for the pleasure of the headmaster, and the kinky story he was caught up in was too good, almost too real, not to shoot his load. The kid was excited with the older man’s sexually charged narrative about life at the all-boys school. Earlier that morning, Bobby was caught in bed nakedly dry-humping against one of the students in the younger grades. He couldn’t have resisted the boy’s advances and was intrigued at the seductive skills of the young teenager who had climbed in through his dorm room window and directly into his bed.

    Headmaster was now weaving and even more erotic version of the innocent experimentation as he coaxed a confession from Bobby and embellished the tale of two naked boys who simply had a case of the morning hornies. Secluded in this private office, Bobby felt his dick once again lurching as he stopped to prevent cum from spurting all over his nudity. As he wantonly displayed himself sexually on the leather couch where so many fresh-faced boys in suits had sat with their parents for entry interviews, Bobby understood how good the headmaster was at engaging each boy in conversation. Now, Bobby was experiencing an intimacy with the soft seductive tones and suggestive words that once again had almost urged him to the brink of orgasm.

    “Think of some of your classmates you see naked in the showers, Bobby. I’m sure you notice their cocks and thought that many of them might be in naked play with others. Well, I can assure you that I’ve had those boys right here with me just as naked and horny as you are, and they tell me fantasies about sucking your cock, Bobby. Can you imagine those twins from fifth form you’ve been perving? Kneeling in the showers, dick-kissing your penis between their sucking lips, licking and tonguing the pleasure spot just underneath and behind your swollen dick head? Would you like to have them show you how much they love cock-sucking the older boys just so they can taste their sperm? Now, cum for me, young man. Shoot your hot juices as you voice your forbidden pleasures about your classmates.”

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