On The Block Ch. 03 Pt. 01

Before his 18th birthday celebrations, Cal would have thought it beneath his dignity to so much as suck the man's cock – he had never bothered learning his name! – but as the tutor entered the study-room, Cal knew with absolute certainty that he would do whatever it took to get the man's dick up his pussy. He wouldn't even need to use the subtle tactics which had worked so well with his friends.

As the tutor entered and closed the door to the study, Cal tossed the man a jar of fuck-grease. In the time it took the tutor to read the label on the jar, Cal got naked and lay on his back on the couch which was conveniently placed near his desk.

"Um, young sir, I, uh, I don't think your honorable father would approve of this..." the tutor stammered, his eyes busy taking in the smooth, leanly muscular planes of Cal's invitingly displayed body.

Casting an entirely approving glance at the large bulge which appeared at the tutor's crotch, Cal tugged at his hardening boydick and drawled, "My honorable father isn't here – I am. So I'm the only one you need to worry about pleasing. Refuse me, and I'll get you fired; give me what I want, and I might even convince my father to give you a pay rise."

A man didn't get to be a Mathematics teacher without being able to think logically – the tutor pulled his shirt and trousers off, and approached the couch. "Very well, sir," dipping two fingers in the slippery gel, he scooped some out, "How would you like to have me, then?"

Bending his knees and spreading his legs, Cal said, "Like this, as hard and deep as you can go!"

The tutor, who had been about to push his grease-laden fingers up his own asshole, paused in momentary confusion at this unexpected order. But his swelling fuckspear rose higher in the air, filling in and stretching outwards as he realized that he wasn't expected to suffer the humiliation of getting shafted by Cal's rich-boy's 5 inch prick, but rather, he was actually being blackmailed into screwing one of the hottest, most seductively forbidden butts he'd ever seen. It was like being forced at knife-point to eat a sumptuous feast.

What remained of his rational mind made the tutor go back to the door and lock it – if he'd been caught bottoming for the kid, he would only have been fired; if he were caught topping that sweet rich-boy ass, he'd be horse-whipped at the least!

Turning back to the object of his lust, the tutor scooped out a generous amount of lube and ran his greasy fingers up and down his rampant bullcock, getting a good coating of lube all over the vein-etched tubesteak. Coming to the foot of the couch, he looked at the offered boypussy and dropped the jar of grease, choosing instead to take a taste of the depths he was about to plunder.

Cal's eyes widened in shock as he saw the man bend down, and the wet, slippery feeling as the tip of the tutor's tongue tickled and titillated his twitching tunnel, tapping and tripping along his outer rim before plunging deep into his hungry, spasming chute.

"Whahhhhhh...?" MOAN! "What d'you think y'r...?" sigh, "Uhhhh! Oh, fuck, yeah!" Cal's hand unconsciously stroked his straining dick, rubbing his free-flowing precum onto the throbbing shaft as he was introduced to a new type of anal delight. "Don't stop! Ohhh, don't stoooooop!"

"Mmmmm!" was the only verbal reply, but the tutor's mobile tongue and lips continued to stroke and suck Cal's sensitive opening, probing deeply and with every sign of lusty enjoyment.

Cal didn't know how long it was before the sloppy rimming, combined with his masturbating hand, made him cum. The pleasure made it seem like no time at all had passed, but the friction-soreness in his palm made it clear that several minutes at least had gone by.

Several minutes during which the tutor's cock had actually grown longer and thicker! Cal's eyes, which had narrowed with pleasure as his cock finished spurting on his flat belly, nearly popped out of his head as the tutor rose up on his knees, revealing his fully engorged 9 inch buttfucker.

"D-d-don't f'get t' grease that thin' s'more!" Cal panted, still out of breath from his orgasm, worry about the size of the bullcock he was about to take in surfacing briefly through the deep puddle of lusty pleasure he was wallowing in. The jar was quickly retrieved, and the tutor's cock was given another coating of the slippery gel before he pressed the broad mushroom head against Cal's spit-slick, twitching butthole.

"Take a deep breath, boy – here it comes!" the tutor gritted his teeth and started to press, exerting a gently but steady pressure to slowly push the broad head through Cal's tight asslips.

"Oh, hell, yeah!" the tutor moaned as the glans went all the way in. Pausing a moment to enjoy the burning-hot grip of Cal's internal muscles, the tutor went to work thrusting the rest of his hard shaft into Cal's wet, massaging rectum.

"Ohh, yeeeeessss!" Cal hissed as the tutor's cockhead brushed against his prostate. One of his friends was a student of Medicine, and after their gang-fuck he had gone out of his way to explain that Cal's many cum-spurting orgasms were an involuntary result of friction against his prostate, rather than an expression of enjoyment – this was his way of excusing one of their social standing seeming to get off on getting fucked. 'Yeah, whatever – so long as it gets lots and lots more friction!' he had thought to himself at the time.

"Fuck! You got an even tighter cunt than my little brother's!" the tutor groaned as he pumped his hips, thrusting his thick shaft back and forth in Cal's clutching tunnel.

"So it's true, then? Peasants really do fuck family members?" Cal felt an extra thrill, thinking once again of his Daddy's studpole, which his memory assured him was even bigger and thicker than the one currently rubbing against his asswalls so deliciously.

"Who you calling a peasant, fuckboy?" the tutor growled, pulling back until only the throbbing mushroom head was still in Cal's gripping asshole before shoving the whole fuckpole back to the root, "I'm a freeman, same as you and your old man – just not as well-off!"

"Yeah, sure, whatever... Hey, what're you doing?" Cal cried out as the tutor pulled all the way out and sat back on his heels.

Gripping his copiously dripping studcock tightly, he gave Cal an evil leer as he began beating himself off. "Now, now, li'l pussy! Here I am, not only giving you all this here big ol' mandick, I also complimented your hot little fuckhole! And instead of saying 'thank you' like a good little fuckpiece, you go and insult me! Maybe I should save this here load for my little brother, after all?" he said, hefting his large, hair balls, heavy with their large cumload.

"No!" Cal shouted, pushing himself up on his elbows, desperate for more hard pounding pleasure, "I'm sorry, sir! I'm so very, very sorry, sir! It won't happen again, sir! Please, just put it back inside me, sir! I need it sooooo bad, SIR!" the last word came out as a cry of joy as the tutor thrust back into Cal's ass, his entire throbbing 9 inches gouging in with one hard shove, balls slapping against Cal's asscheecks. "Ooooooh, that hurts soooooo goooood!"

It was a struggle to keep his movements slow and gentle – so the tutor didn't even bother trying, slamming his bulldick to the hilt with every forward thrust, heaving back and forth with all the power of his muscular ass and thighs while Cal called out encouragement and bucked up to meet his slamming in-thrusts.

"Alright, now, reach up and pull my tits!" the tutor grunted, arching his back and presenting his chest. Cal's only reaction was a puzzled look, so he added, "My nipples, cuntboy! Grab those little pink suckers and twist!"

Raking his fingers through the tutor's thick chest hair, Cal found the hard little nubs and pinched as hard as he could. His eyes widened with surprise as he felt the tutor's bullcock swell further, the large manmeat filling his asstunnel even more.

"Yeah, that's it, bitchpuppy! Hurt 'em good, and Daddy'll fill your sweet pussy with what it needs – lots of hot studcum!"

It was definitely the use of the "D" word that made Cal's balls pull up tight and his cum shoot in thick ribbons along his chest and stomach – but the swelling, stroking mandick flooding his rectum with spunk certainly helped.

The tutor shoved his swollen swollen cock as hard as he could, the emptying a pint of mancum into the furthest depth of the moaning boy beneath him. Still inflamed with lust, he pulled his still-cumming horsecock out of Cal and crawled up the boy's torso to press his spurting cockhead against the boy's lips, "Open up, slut."

Cal's couldn't quite focus his eyes as he looked up at the man looming over him. But him mouth was well trained, and even though he had never attempted sucking anything as big, he pressed his lips against the spongy head and sucked the burning hot, cum-spurting mushroom into his panting mouth.

After the tutor's orgasm subsided the man backed up, pulling his dick out of Cal's mouth as he sat down on the couch near Cal's cum-leaking ass. His fuckrod lost some of its rigidity, but was still swollen and upright, and he knew that it wouldn't take much to bring it back to full boyfucking erection. Looking at the glazed look on his student's face, the tutor decided to push his luck. "Now, was that enough, or does your hot little pussy want some more?"

Cal pushed himself up on his elbows, surprise written all over his pretty face. "You can do it again?" His friends always had new hard-ons within two or three minutes of cumming, but he distinctly remembered that his Daddy and the other older men at his 18th birthday party had taken at least half an hour to get hard again after an orgasm.

"Hah! Do you know how I got into the University? I fucked my way in, just like every other scholarship boy there! I worked my way through all ten members of the entrance committee – and most of them weren't any more interested in my ass than you are."

"Wow!" Cal's world-view rocked as he thought about this. As the son of a prosperous merchant, he'd met several of the committee members at various occasions, and he couldn't imagine a single one of those dignified, staid-looking gentlemen taking a cock up the ass any more than he could imagine walking on the moon.

"So, if you're interested, you can show it by lapping me back into shape," the tutor said, recalling Cal's attention to the present – and to a future which could involve him getting dicked again if he got a move-on.

Kneeling on the carpeted floor between the tutor's thighs, Cal went to work. The tutor's fuckpole had a flavor Cal had never tasted before – since he'd never tasted ass before – and he found it surprisingly exciting, rather than distasteful. 'This cock's bred my butt!' he thought as he tongued along the twitching column of flesh, licking cum and other musky streaks off in long swipes, swallowing every mouthful without hesitation or reservation. Some of the slippery semi-liquid had dripped down to the tutor's balls, and he made sure to thoroughly lap those pendulous orbs as well, stirring up their contents in anticipation. 'These nuts emptied out into my boycunt!'

It only took little more than a minute to "lap him back into shape", but both of them were enjoying Cal's cleaning so much that the tutor allowed him to continue for some time, letting Cal run his tongue along every inch of his engorged cock and balls over and over again, before tapping the boy on the head by grabbing his throbbing member and pushing it down, hard, twice. A drop of precum fell off the reddened glans just as Cal looked up, the clear fluid mixing with the sweat already covering the boy's cheeks and the spit running down his chin.

"Time to get back the main even," the tutor gently reminded Cal by waving his swollen bulldick from side to side.

"Oh, yeah," Cal answered, a little dazed from oxygen deprivation, since there was very little fresh air around the tutor's sweaty, hairy groin. Groping around the floor, he managed to pick up the lube jar after a few fumbling tries, and scooped out a generous amount to rub onto the fleshy pillar. Rubbing the remaining grease on his hand around his sore assring, he let the tutor pick him up by his armpits and pull Cal into his lap.

Other than a muted hiss of discomfort, Cal made no protest as the cockhead was inserted back inside his buttring, and he immediately pushed down with all his weight to feed all that swollen manmeat to his gluttonous glutinous, feeding his hungry boycunt in one quick plunge.

Shifting his hold to the sides of Cal's chest, the tutor helped the horny boy bounce up and down his throbbing horsecock, once again not bothering to try and prolong their sexual gymnastics by keeping things slow and gentle – this kid was gagging for a hard fuck, and he was more than willing to take out all his class-frustrations by pounding Cal's pussy to a happy pulp.

"Hoooooh, shit! Big! Ugggh! Hard! Gimme! Ahhhh!" Cal grunted deliriously, fireworks going off behind his closed eyelids as he shunted up and down as fast as his thigh muscles could push him, his prostate on fire from the volcanic heat of his tutor's engorged fuckpole.

"Yeah! Fuck! Take it!" the tutor's balls felt like they were about to burst, his hairy sac full and tight against the base of his plugging, plunging bullcock.

Cal shifted his angle slightly, making his throbbing, precum drooling boydick rub against the tutor's kinky belly-hair. "Ooooooh, that's it! Here it CUMS!" The perfect combination of friction on his pecker and prostate sent Cal skyrocketing into his climax, thick globs of boycum shooting up the tutor's chest, one spurt smacking the underside of his chin, spatters ricocheting to land on Cal's sweaty, heaving chest. "FUCK! HARD! COCK! IN! ME!"

It was a good thing no one was in any of the nearby rooms – or the garden outside the study's window – or they would certainly have come running as Cal screamed out his pleasure. The tutor's orgasmic cries were swallowed up in the noise, just as his spurting cum was swallowed deep inside Cal's bucking body.

Cal slumped against his tutor's sticky torso, not caring that his drying cum was rubbing into his hair as he half-lay exhausted against the bigger man. The tutor's twitching studcock, still buried to the hilt inside his cum-sloppy ass, was the only thing keeping the boy from falling off the man's lap onto the floor in a boneless, sated heap.

The tutor himself was sitting back in the couch, basking in the post-cumming quiet while he caught his breath. Coming out of a light doze, his brain kicked in for the first time since he'd thought to lock the study door. The tutor looked down at the sticky, sweaty mess sitting on his thighs. "I don't suppose you've got a towel handy, do you?"

"Huh?" Cal was dozing, feeling wonderfully drained and wanting nothing more than a nap – preferably while the tutor's horsedick stayed exactly where it was, so it could keep him stretched and service him some more when he woke up. His dazed mind couldn't understand how a towel fit into this seductive scenario.

"We need to get cleaned up, kid," the tutor said, imagining the trouble he could get into if someone caught his young, rich student with a cum-oozing ass. "If anyone sees all that spunk leaking out of you, we'll both be in deep shit."

Cal's first thought was that he could simply lick it up like he'd done after their first fuck – but then he realized they were talking about his ass, not the tutor's crotch. Which made him think of what the tutor had done before, "How about you clean me up?" he suggested, leaning back a little to look his tutor in the eye. "After all, you made the mess," he winced as he pulled up one leg and unplugged the tutor's softening fuckrod, carefully shifting his weight and slowly lay back on his back on the couch with both knees bent and pressed to his sticky chest, "It's only fair that you clean it up."

"All right – but you'd better clean me up, too," the tutor said, quickly moving to a push-up position with his head between Cal's legs and his own horsecock and balls dangling in Cal's face.

Cal decided that being inside his slick butthole definitely made a man's dick taste better – the musky tang gave it an added piquancy that went straight to his balls, making him moan with pleasure as he lapped at the drying cum matting the tutor's shaft and pubic hair.

And the tutor's tongue felt even better than before in Cal's ass – his raw asschannel felt even more sensitive as the nimble muscle pushed its way deep inside his well-fucked pussy.

By the time one of the servants knocked on the door to inform his young master that dinner was being served, Cal had been thoroughly serviced six times, followed by a leisurely mutual tongue-bath. It was just as well that the lesson time was over – even Cal's talented tongue couldn't get a fresh hard-on out of his exhausted tutor, and Cal's own body was starting to feel the strain of all the unaccustomed activity.

The next morning Cal was feeling too sore to do more than jack off, carefully clenching his still raw-feeling assring as he shot cum over his tight fist, before rising and eating his breakfast.

That day's lesson was Law – the land's various taxes, what purpose they served, which ones could be avoided with careful bookkeeping and so on. Cal hadn't actually progressed beyond the basics yet, but he wasn't expected to do all that for himself anyway – his father had an accountant for the purpose, and when the time came Cal would do the same. But it was important to know these things, to avoid being cheated.

The tutor for this subject was middle-aged – older than the Mathematics tutor, but not as decrepit as the History tutor – his brown hair was slightly threaded with silver, and crow's-feet crinkled the corners of his blue eyes and lined his forehead.

As they waded through the various laws, with all their subtexts and possible loopholes, Cal thought to himself that if the previous day's "lesson" hadn't left him quite so sore, he might have tried seducing this man as well. 'Something to think about in the future,' Cal thought, and tried to focus his attention on the texts they were reading and not the faint throb he felt in his swollen anal-ring.

At dinner Cal and his father met for the first time in a few days – sometimes they took every evening meal together, but lately Daddy had been working long hours and taking his meals at his dockside office. Even now, Daddy was only able to stay long enough to eat and make light conversation with his only son before setting off for a late meeting with one of his shipmasters.

All through the meal Cal found himself staring at Daddy's lips – imagining them pressed up against his own; Daddy's hands – picturing them stroking his body, his young cock; the V of chest hair visible through the front of Daddy's shirt – would the hair be soft, or rough like the Math tutor's? Were his nipples as pink?

Cal shifted on his sore buttocks several times as his cock twitched and drooled inside his breeches, imagining the various activities and positions the two of them could get up to. Their positions at the table hid the evidence of his desire, just as it kept his naughty eyes from seeking Daddy's crotch directly, but his mind's eye clearly supplied the memory of Daddy's hard fuckrod to help fuel his fantasies. 'Screw the pain – I've gotta get some more cock in me soon,' he decided, taking a sip of his wine to disguise his desire-flushed face.

That night, Cal took a detour on his way to his room, sneaking into the kitchen pantry to grab a pair of cucumbers as masturbation aids. They worked well enough – he was relaxed enough to go to sleep after the third time he fucked himself to orgasm on a slippery vegetable – but they weren't nearly as pleasurable as the real thing.