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Chapter 3
For almost an hour, Santa waited for Will to arrive at his rooming house. He'd been so excited when the boy had texted him! He'd even put his Santa suit back on after an early shift at the mall, just for the boy's enjoyment, but it was an effort that Santa now bitterly resented. His annoyance and disappointment had built as the minutes passed, and had finally curdled into a deep fury.
Had the boy not contacted him? Had the boy not said he needed to see him? Had the boy not pleaded a little, even? He had, he had, and he had! And then the boy had chickened out. What other explanation could there be? The boy had gotten Santa worked up only to leave him high and dry, and incredibly angry. The boy was a prick tease!
Santa pulled off his itchy red hat and tossed it across his shabby little rented room. He unlaced his black boots and pulled them off, then threw them, too, for good measure. They crashed against the opposite wall with a loud, satisfying thud. Santa rose and began unbuttoning the heavy, furry top part of his suit, the coat. He walked to the window as he unbottoned, to adjust the flimsy old curtains, and that's when he noticed the car below, the familiar car. Santa stared at it for a moment in amazement. He could just see the outline of a curly headed young man in the front seat.
A voice roared inside Santa's head: WHAT THE FUCK?
He couldn't believe it He couldn't explain it. But it was, maybe, a stroke of luck?
Santa got his phone.
"I can see you down there, young man," he texted.
Moments later, the simple reply from Billy: "I'm scared."
"Nothing to be scared about," Santa wrote.
"Can you come and get me?" Billy wrote. "I'm afraid to go in alone."
Once again, Santa's mind was asking itself, What the fuck?
Was the boy really that timid? Santa knew he was inexperienced, but he couldn't even go inside a house and knock on a door? What a little weakling. What a little pussy.
"Yes," he wrote back. "Be there in a couple of minutes."
He dressed as quickly as he could, but it was an effort, and Santa was not pleased to be the one making the effort. He was even less pleased when he ran into a woman in the hallway of the rooming house, who wanted a picture with him in his Santa suit.
"Fuck off, lady," Santa said, as he brushed past her.
Behind him, the woman gasped in surprise, but Santa paid no attention. Down the stairs he went, out the door, and there was young Billy in his car, cute and trembling like a cold puppy.
"Ho, ho, ho, Billy," Santa said, in a voice thick with false joviality. "Merry Christmas!"
Almost instantly, Billy felt better. Santa was so big and red and fuzzy, and so jolly. His boner flexed in his shorts. He hopped out of his car and would have given Santa a big hug had Santa not abruptly turned and started walking away before he had the chance. Billy followed, a meek, pale little bundle of nerves with a small but fierce erection, faithfully following Santa as if he was a blazing beacon of light. Up the stairs, up, up and away, and into Santa's small, untidy room. Santa slammed the door behind the boy, and then carefully locked it.
"Well, Billy?" Santa said. "What do you have to say for yourself?"
Billy's eyes grew wide. In his excitement, he couldn't think of a response. It didn't register with him that Santa's own eyes were narrow and hard, that the man's tone of voice had gone flinty.
"Well?" Santa repeated.
"I'm sorry I was late," Billy said.
Santa shook his head.
"But you weren't late, were you, Billy?" Santa said. "Tell the truth."
"I just couldn't get out of the car," Billy said. "I was too scared."
"You're scared of a lot of things, aren't you, boy?" Santa said.
Billy's sweet face, lit with joy, suddenly sensed something was wrong. He bowed his head.
"Yes," he admited. "Everyone used to call me a fraidy cat."
"I see," said Santa. "And what are you afraid of now, young man?"
"That you're mad at me," said Billy, his voice quavering.
"And do you think I have reason to be mad at you?"
"Yes," Billy whimpered.
"I agree," said Santa. "Why do you still have your clothes on, Billy? Remove them at once."
Billy's eyes widened again. Things were moving more quickly than the last time he'd met Santa. Things seemed somehow different. He hesitated to fulfill Santa's request.
"Billy, I told you to take your clothes off," Santa said. "When I tell you to do something, I want you to do it right away. Do you understand?"
"Yes," Billy said.
He pulled off his shoes and socks, pulled off his shirt, undbuttoned his pants and slid them off, but he stopped short of pulling off his white briefs, as he had the first time he'd been with Santa.
"Keep going," Santa growled. "I already know how small your penis is, so there is nothing to hide."
It was like a slap in the face, the directeness, the almost casual manner in which Santa referred to the biggest source of Billy's anxiety and fear. It was like a slap in the face, the disdainful tone of Santa's voice.
But Billy obeyed, quickly this time, shucking his shorts, then standing in all of his naked beauty in front of Santa. He did not try to hide himself with his hands. As Santa said, there was really no point, because Santa had seen it before.
The boy's penis was pink and very erect, rising upward at a sharp angle from his tidy little bush, but not stretching beyond it, though it was so rigid that it was almost parallel to his body.
Suddenly, Santa started laughing. Billy's face colored quickly, flushed with humiliation.
"That's a real small dick, isn't it, Billy?"
Billy started to quiver. His eyes dropped miserably to the floor again.
The older man strode forward, and he grabbed Billy by the chin.
"Look at me, boy," he growled.
The effort was painful, looking into Santa's cold eyes, but Billy obeyed. He thought he might faint.
"I said, 'that's a reall small dick, isn't it?'"
"Yes, Sir," Billy said.
"The smallest dick I've ever seen in my life," Santa said.
"Yes, Sir," Billy repeated.
"I want to hear you say it, Billy. Say 'I have a very small penis.'"
"I have a very small penis." Billy said.
Tears welled up in Billy's eyes, heavy tears that couldn't help but fall.
"Why yes you do, Billy!" Santa said. "How does it feel to say it?"
"It hurts," Billy said.
"Yet it's the truth, isn't it?"
"Yes."
"Have you ever measured it?" Santa asked.
A look of pure panic came to Billy's eyes.
"No!" he cried. "Please, stop!"
"You don't say no to me, Billy," Santa warned. "Not ever."
Billy couldn't reply. He could barely see though his tears.
"Quit your blubbering!" Santa said. "Go over to that dresser beside my bed and open the top drawer."
Billy obeyed, but on shaky legs. His terror had begun to turn numb, and his mind felt sluggish. When he opened the drawer he saw a bible and a pad of notebook paper. Nothing too frightening after all, but he had to wonder what a bible was doing in Santa's drawer. He didn't know that he wanted to find out.
But the bible wasn't what Santa was after, nor the notebook. Following Santa's orders, Billy lifted them and then saw what Santa wanted, underneath.
"NO!" Billy said. "Please, no, Santa."
"Bring it to me, young man," Santa said.
Billy picked up the ruler that had been hidden beneath the bible. He brought it to Santa. Despite his mortification, or maybe because of it, he still had a strong erection. Even more than that, a pearly little thread held a tiny bead of pre-ejaculate suspended from the tip of Billy's hard penis, and the bead was slowly growing in size.
"Just for kicks," Santa said, "how big do you think it is, Billy?"
"I don't know," Billy said, in the coolest voice he could muster.
"Bullshit!" Santa laughed. "You've never measured yourself before?"
"No!" Billy said, emphatically.
"Then how big would you guess it is?"
"I honestly don't know," Billy said.
"You lie, Billy," Santa said.
"It's four inches!" Billy squealed. "Okay? Can we drop this now? Please?"
"No, we cannot, Billy," Santa said. "And I don't like your tone."
"I'm sorry," Billy said.
"Good boy," Santa said. "Now come here."
Billy moved close to Santa, and then felt the man's large index finger and thumb come down like pincers over his penis. They moved slowly over his raging length, what there was of it, and the bead of precum, suspended for so long, came loose and went flying.
"Are you ready, Billy?" Santa said.
Billy was too upset to reply, so Santa repeated himself in a harsher voice. Billy finally nodded.
"Now stand still," Santa said.
The cold ruler came to rest on top of Billy's drooling penis. Santa moved it down, so that the end was flush with the base of the boy's pubic bone.
"That's not the right way," Billy whined. "It's supposed to be from the side!"
Santa chuckled, and kept right on doing what he was doing. He pressed his thumbnail down hard on the place where the tip of Billy's erection maxed out against the ruler, making a distinct mark in the soft wood. Billy's penis, released from Santa's grip, issued a fresh new bead to replace the one that had fallen.
"Care to look at the truth, Billy?" Santa said.
"I told you I already know," Billy said, in a snitty voice.
Santa just chuckled. He raised the ruler, handed it to Billy, and told the boy to look for the mark.
Billy looked and looked, but he didn't see anything near the four inch mark.
"I can't see the line," he said.
"Well I had no problem seeing it," Santa chuckled.
He snatched the ruler away from Billy, then held it close to the boy's eyes.
Billy looked and looked, and then his eyes widened in shock.
"No way," he said, with a hysterical edge to his voice. "That's not right."
"It is, Billy," Santa said. "You have a smaller penis than you thought."
"No way," Billy repeated.
"The wood don't lie, young man," Santa said. "Tell me what it says."
"It says my penis is three inches, but that can't be right," Billy said.
"Wrong!" Santa boomed, in anger at Billy's evasions. "Your penis is not even three inches long, and that is the whole truth and nothing but the truth."
"No!" Billy screeched. "It can't be!"
"But it is, Billy, it is," Santa said. "You have to accept it, and accept that you will always be a boy, never a man."
The pretty young face crumpled in on itself, tears welling up heavily again. He began to quiver.
"How big is your penis, Billy?" Santa said.
His voice was ominous. Not a peep came from the boy's pouty lips, but his fallen face told Santa that he was struggling to accept this new, harsher reality.
"Say it, Billy," Santa said.
"My penis is tiny," Billy crushed voice said.
"How tiny?"
"Not even three inches. Just under."
"You have a micropenis, don't you, Billy?"
"Yes."
"You're not a man, are you, Billy?"
"No."
"You'll never be man, will you?"
"No."
"It's shameful and wrong for a boy like you to masturbate such a tiny, worthless penis, isn't it, Billy?"
"Yes."
"And did you masturbate, Billy? After I told you that you were no longer allowed to do so?"
"No," Billy said, but his voice was too sharp, and it betrayed him.
"Billy," Santa said. "I want the truth now. Did you masturbate?"
"No!" Billy screeched. "Not really!"
"What does 'not really' mean? Did you or didn't you?"
"It wasn't really masturbating. I didn't touch myself?"
"Did you cause your little penis to have an orgasm, Billy? Without your wife?"
"Just with the shower spray! It wasn't masturbating!"
"Yes it was!" Santa shouted. "It doesn't matter how you did it! In fact, the shower thing makes it worse!"
Santa snapped the ruler in half to emphasize his fury.
"I'm sorry," Billy whined. "I didn't mean to!"
"You're not sorry and you did mean to!"
Billy started to cry. He knew it was wrong when he did it, when he gave in to temptation, and he knew it was even worse to make excuses about it. Santa didn't deserve that.
"I've been a bad boy," Billy said. "I'm sorry for arguing."
"But sorry's not going to cut it, is it, Billy?"
"No."
Billy hung his head. He felt ashamed of himself. His little penis was still hard, despite the mortifying truths Santa had dropped on him only moments earlier. His little penis was so hard that it hurt.
"I want you to go back to the nightstand and open the second drawer, Billy. You may choose your punishement, but choose wisely, young man."
Billy obeyed. The open drawer revealed two paddles. A large, shiny one made of polished wood, with several holes cut out of the business end, and a smaller black paddle that looked like it was made of plastic or rubber. Billy picked this one up, and shook it a couple of times, noting that the end was flexible. Though smaller, something about that paddle made Billy nervous. Maybe it was the black color. He didn't know. He picked up the larger wood paddle and brought it to Santa.
"Wise choice, Billy," said Santa. "Now get on Santa's bed, please. On your hands and knees, with your bottom sticking out, facing me."
Billy made an attempt to follow Santa's orders, but his mind was confused.
"No, Billy!" Santa said. "With your bottom facing me, not your face."
Billy turned himself around on the soft bed with some difficulty.
"Yes, that's better," Santa said.
With quick strides, Santa moved to where the boy was presenting his bottom. For a boy so lean, Billy had quite a plump little rear end. It was snowy and pale, and completely hairless. A pair of small pink testicles were stationed just below Billy's bottom, tight to his body, held that way by the extreme angle of Billy's little erection, which was nearly flat to his belly and pulled everything up with it. Just those little pink orbs showed, so dainty and sweet, yet so utterly insignificant. Blink and you missed them entirely.
"You have really small balls, Billy," Santa said. "Did you know that?"
"Yes, sir," Billy said.
"The smallest I have ever seen."
"Yes, sir."
"Tell me, Billy."
"I have very small balls," Billy said.
"To match your tiny penis," Santa added.
"To match my tiny penis," Billy echoed.
"Say it all together now, Billy," Santa said.
"I have very small balls and a tiny penis," Billy said.
"Good boy!"
Santa's red rocket had firmed up quickly beneath his fluffy, scarlet suit. He leaned over and wrapped his arms around Billy's middle, dragging the boy closer to the edge of the bed, so his bottom was almost clear of it. Santa grabbed the paddle. Santa leaned down, not too far because of the tallish bed, and grabbed Billy's penis. His thumb, as thick as its quarry, found the top of the penis, right above the head, and then his index finger found the tender spot on the underside of the small organ, just below Billy's tiny circumcision scar. Santa pinched. Billy squirmed.
"We don't want another accident like last time, do we, Billy?" Santa said.
"No, sir."
Santa kept the pressure up until Billy's penis wilted into a small, pale noodle. Then he raised the paddle high above his head. When it came down it connected with such force that the boy's whole body reverberated, and the sound echoed off the walls. Billy's body, shocked by the pain, which was much worse than anything it had experienced during the first spanking, convulsed involuntarily, but Santa took hold of Billy's pink little marbles and prevented him from scooting away.
"Calm yourself, boy," Santa warned. "We're just getting started."
"Yes, sir," Billy said, but his voice broke into a sob half way between the two words.
Santa surveyed his handiwork, pleased with himself and with the boy's reaction. The rows of holes in the paddle showed a clean white where it had landed on Billy's tender flesh, pale circles surrounded by blazing, fiery scarlet.
The second blow was even stronger, louder. Billy began to whimper, and by the third blow he was bawling uncontrollably. He had wanted to be strong, he had wanted to show a good account of himself through self discipline, but it was impossible under such force, under such pain. The worst of it was that Santa was taking his time, striking only when the fancy seemed to move him. Billy never quite knew when the paddle would hit him again. It was unnerving. It was terrifying. And the blows were growing more fierce.
The fourth one nearly took young Billy's breath away. He screamed into the empty air. Santa held him firmly by his balls, which had gone numb. The seconds ticked away, and then another blow struck, followed quickly this time by another, a double whammy of cacophonous noise and pain. Billy's body went into fits, but he could not escape Santa's insidious fingers, wrapped so tightly around his balls, though his body did move here and there. But never far enough to escape the paddle.
Five. That was five, Billy thought. Maybe it was over? A moment later, the paddle hit its mark again, and Billy howled. His bottom was no longer thrust upward but rather hunched under Billy's body as much as possible, as if that would protect him. Another reverberating connection between wood and tender flesh filled the room. Billy's lungs were sore from screaming.
"Silence, boy!" Santa said. "You are only making it worse for yourself."
And indeed it was true. Billy's screams and attempts to escape only made Santa angrier, only increased his determination to beat the boy's buttocks all the harder. His fat cock was raging.
"That's better," Santa said.
A silence ensued, a stillness. Billy didn't dare to hope that it was over. There was no hope. None at all. The paddle found his ass again.
"Please!" he shouted.
"Silence!" Santa responded.
The paddle hit him again with great force. Billy wondered if it was tearing his skin, turning the flesh underneath to hamburger. It felt worse than anything Billy could ever imagine. Until the next shattering blow struck, forcing him to reevaluate his opinion, quickly followed by another, even fiercer, connection, and then another. Billy was clawing the sheets of Santa's bed, trying to escape. It was too much. Way too much.
"Calm down, Billy," Santa said.
His voice was now soothing. Billy relaxed, came out of his panic for a moment. Tears were still streaming down his face.
"That's better," Santa said.
"Yes, sir," Billy said.
"That is ten, Billy," Santa said. "How many more do you think you deserve?"
"I don't know," Billy said, in a quavering voice.
"Wrong answer!"
The paddle stuck again, hard. Billy clawed at the sheets, his fingers grasping for purchase, quite uselessly. His mind was telling his body to move forward, away from the paddle, and he couldn't think past this impulse, couldn't understand that moving toward it, backward, would push him off the edge of the bed and away from Santa's easy reach.
Another loud crack came, then the searing pain. His bottom felt like it was an inferno, felt like it was literally roasted. The blows came quicker now, but no less easy. Tearing across the already mortified flesh, reaching every square inch of his buttocks, sending them blazing again and again, leaving him howling and convulsing with tears and pain.
"That's twenty, Billy," Santa said. "How many more do you think you deserve?"
"One, Santa!" Billy shouted.
"Let's make it two," Santa said.
Billy steeled himself for the second to the last blow. He expected the worst. Yet when the paddle fell, it was no more painful that the previous blows. Perhaps he had gotten used to it? Perhaps he would be okay, after all? Only one more, and it was over. He cried in anticipated relief.
Santa raised the paddle far above his head. It sat there, poised, for quite a while, and then came down like lightning. All of Santa's frustration, all of his considerable anger, built over a lifetime, came down with that paddle and slammed with incredible force against Billy's trembling little rear end. The power of it knocked Billy's plump cheeks forward, indeed knocked his whole body forward on the bed. He screamed at the top of his lungs and the tears poured down his cheeks.
Santa tossed the paddle aside, and admired his work. Those lovely, pale, innocent looking buttocks the boy arrived with didn't look so innocent anymore. They were beyond red, almost a purple shade, the color of the stains made by almost ripe mulberries, fallen prematurely, and they trembled and quivered. The boy was still wracked with convulsive sobs, quite pitiful to hear, quite pitiful to see, but not for Santa. Santa was still roaringly hard and Santa was ready to roll.
"Enough with that, Billy!" he said. "It was only twenty two swats."
"Swats?" Billy said.
"Yes, swats," Santa said. "Now turn around. I want your ass pointed the other way now, not too far from the headboard."
Billy complied. His mind was numb, and he could offer no resistance to Santa now. His penis, also numb, along with his balls, remained soft.
Santa made his was to the bed carrying a large tube of what Billy presumed to be lotion. He suddenly stiffened, because he knew that it would hurt if Santa touched him there, even if it was just gently, for a massage. The larger man set pillows upright against the headboard, then settled himself onto the bed so that part of his upper body was supported by them.
"Come, Billy," Santa said. "Move backward."
Billy obeyed. Santa's hands felt up Billy's butt, and the boy winced.
"Santa would like you to please him, Billy," Santa said. "Can you do that?"
"Yes, sir," Billy said, in a hoarse, worn out voice.
"Good boy!" Santa said. "I think you know what to do."
Indeed Billy did. He gently pulled Santa's long coat out of the way. He zeroed in on the spot that Santa wanted pleased. It was big and stiff beneath the plush red fabric, and Billy felt it up thoroughly.
"You may take it out, Billy," Santa said.
Billy struggled to find a zipper in the furry fabric, couldn't figure out that it was concealed beneath a little flap of material. Impatient, Santa shoved Billy aside and unzipped it himself.
"Pull it out, Billy," Santa said. "There you go."
The fat penis emerged under Billy's guidance, almost a red as Santa's suit. Billy gripped it gently and began to stroke it. He had a sudden yen to pull out Santa's balls, for they hadn't made an appearance during their last encounter, but Billy didn't dare risk displeasing Santa. Santa grunted as Billy stroked him.
"Good boy," he said.
A noise like a particularly wet fart startled Billy, but he kept stroking Santa, like a good boy should. Santa had squeezed a large dollop of lubricant into one of his palms.
"Move your butt a little closer," Santa said.
Enraptured with Santa's fat cock, and intent on playing with it, Billy obeyed, even though he was apprehensive about his bottom. Something about Santa's penis comforted him and made everything else seem unimportant.
Santa dipped two fingers into the lubricant, just a light amount, then placed the tips of them near Billy's tiny pink anus. The cool, liquid feeling made Billy shiver. His tears had dried, and he was in the moment, sensitive to each new feeling. The fingers moved gently but eagerly in a circular motion, and the gel soon warmed up. The repetitive motion left a feeling that was soothing, even relaxing.
"Go ahead and put it in your mouth, Billy," Santa instructed. "Get it nice and wet."
A shiver ran down Billy's spine, not from cold this time. He put his lovely face next to Santa's erection, his warm breath stirring the rock hard organ into even greater fullness. Billy kissed it at the tip, then kissed it all over, like it was a cherished toy, like it was a stuffed animal. His tongue shot out, the narrow tip touching the tip of Santa's penis, then sliding down the shaft, then up again, back to the head. Billy opened his mouth and lowered it delicately onto Santa's pole.
"Mmmmf," Santa grunted.
The warm mouth slowly engulfed Santa's length, began bobbing up and down on it, the textured tongue pressed firmly against Santa's flesh with each movement. Santa had forgotten how quickly the boy had learned, how talented his mouth had become in such a very short amount of time. Yet the mouth was not wild with desperation. It seemed to savor Santa's penis just for its own sake, expecting no reward, at least not yet. Billy settled into an easy rhthym on Santa's cock, teasing it and further stirring Santa's ardor.
The first fat finger took the plunge, invading the boy's tiny pink hole. Fully lubricated, it moved in and out of Billy's tight channel at the same easy pace with which Billy sucked Santa's cock. Santa's other hand reached down, and found that the boy's penis had returned to full, leaking erection.
"You're not to have an orgasm, Billy," Santa said. "Do you understand?"
Billy muffled voice vibrated affirmatively around Santa's penis.
"Do you need Santa's help? I want a real answer this time."
Reluctantly, Billy pulled his mouth off of the cherished penis, but not for long.
"Yes, sir," Billy said.
And then he quickly engulfed Santa again.
Santa once again took Billy's delicate little erection into his hand, moved it until his fingers were in position, then squeezed until the head Billy's tiny penis was once again clasped between index and thumb, but more gently this time, with just enough pressure to prevent an unwanted ejaculation. The slick, burrowing finger of the other hand resumed its work in Billy's hole, plunging deeper and faster than before as the speed of Billy's sucking increased.
Another finger plunged, eliciting a muffled gasp from Billy and a convulsion from his tiny penis. As before, Santa started gently, but was soon burrowing both fingers with gusto up the taut channel, taut, but slowly relaxing, slowly becoming more pliable. Billy's mouth was sucking madly at Santa's big pole.
"Slow down, boy," he said. "Nice and steady does it."
It was an effort, but Billy obeyed. He didn't want to think about what he was doing, because it felt so good to be lost in it all, to fall into the natural rhythm, the rhythm that brought the reward that Billy was eagerly anticipating. It didn't matter that his own penis was blocked from orgasm. Billy wasn't thinking about that at all. What came to his mind when he thought at all was a desire to do his best to pleasure the penis in his mouth, to accept the thick fingers driving into his rear, and to make Santa happy any way he could.
"Stop," Santa said, suddenly.
Billy didn't want to, but he obeyed. He lifted his head delicately off of Santa's erection. The fingers were withdrawn, and then punged back in again, cold this time, covered in fresh lubricant.
"Come, Billy," Santa said. "It is time."
Billy crawled over to Santa, looked into his eyes. They were much gentler than earlier, soft, even. Billy wanted to kiss him, and the idea surprised him.
Another wet farting noise deposited another huge glob of lubricant into Santa's palm. He rubbed this over his raging erection, pulled Billy over his body until the boy was straddling him. Such a lovely, lovely boy, so gentle and sweet, Santa was thinking.
Billy's eyes were a deeper color than usual, the lids heavy. He knew what was coming. He should have been scared or at least nervous, but there was nothing, only a feeling of well being, of intense desire.
Santa pushed the boy's body down a bit, down until the plump little bottom touched his big cock. Whatever pain the boy still felt from his rough paddling earlier seemed to have faded, or perhaps had been subsumed by desire. Santa reached down, moved his cock so that it was nestled in the warm valley between Billy's buttocks. He guided the tip to the entrance, not so tiny as before, but hot and velvety.
"Pull your legs to your sides, Billy, and hunch down," Santa said. "Like you're doing squats in a work out."
Santa held himself steady at Billy's entrance, and felt the soft, wet flesh press down hard against him, but he could not break through.
"Lift up a bit and then try again," Santa urged. "Keep trying until you feel me slip inside."
Billy did as ordered, pressing down harder this time, but his anus did not stretch to admit the thick erection, and the pressure against this most tender of places was painful. Painful and frustrating, too, for it seemed to Billy that it should have been easy. He hunched up a bit and then bore down once again, but Santa still couldn't break through, and the pain was getting worse. The pain felt like the most unpleasant stretching imaginable, even though Santa's cock had not penetrated. It was a useless pain, a pain without reward, but it was pain nevertheless, and a pretty strong pain at that. Billy's erection had wilted completely, a miserable, helpless little button, like the sad cap of a small, half buried mushroom.
"Wait a minute, Billy," Santa said.
A huge glob of lube was squirted into Santa's hand this time, all that remained in the tube. Santa spread some on his cock, slapped the rest between Billy's cheeks, creating a gooey mess that completely swamped and covered the hole and all around it. He pulled Billy into position again, lined his cock up with the resistant hole.
"Try again," Santa said.
Billy didn't hesitate. His plunged himself down, and Santa's cock breached the more pliable outer ring of Billy's anus. The boy gasped. Santa lunged, forcing his thick cock upward and busting through the second, vice-like ring, burying himself halfway inside the now hollering youngster.
Billy tried to lift himself up and away, but Santa's hands came down fast, grabbing the boy's hips at the place where they met his bent legs, and their iron grip held the struggling boy firmly in place.
"Just relax now," Santa said. "The first time is always rough."
"It hurts!" Billy screeched. "Oh god it hurts!"
"Of course it does, Billy!" Santa said, in a cheerful voice. "Your boy pussy is trying to adjust to a man's cock inside of it for the first time. It's natural!"
Even through the screaming pain, Billy was struck by Santa's words. His boy pussy? He had a pussy? His anus was a pussy? He squirmed on Santa's lap, thinking of these things. The searing, stabbing pain subsided a bit, but the stretched feeling was almost as bad, and Billy couldn't shake it. It felt like his insides were going to burst.
"You ready for me, boy?" Santa said.
Billy wasn't but he drew in a sharp breath, gritted his teeth, and nodded. Santa's pushed the boy's hips down, not sharply, but with unrelenting pressure, and then Santa slammed up into him. He did this repeatedly until his cock was fully buried inside of the whimpering boy.
The furry pants were uncomfortable against Billy's bottom, too hot and itchy, and he could feel Santa's wirey pubic hairs against his delicate pink testicles. He knew he was impaled to the hilt. He felt completely, incredibly full in a way he could never have imagined. Yet the discomfort was bearable, after those few rough penetrations, after the shock of brutal deflowering. And, somehow, Billy still wanted to please Santa. What Santa had done was necessary. Billy believed it was true.
"Ready for more?" Santa asked.
Billy nodded. He began to gyrate his buttocks, feeling the cock within him shift ever so slightly with his movements. The pain was still there, yet there was something else, something small inside him, that felt good.
"Up and down, Billy," Santa said. "Go gentle if you need to."
Billy did as Santa instructed, clearing off an inch or so, then sitting back down again. He repeated himself, then fell into a gentle rhythm, slower than the rhythm of when he'd sucked Santa's cock. It felt okay. Sore, but okay, and Santa was smiling encouragement at him, which helped tremendously.
"Such a sweet, sweet boy pussy," Santa purred. "So soft but so tight."
Emboldened, Billy increased his pace, began allowing more of Santa's turgid member to escape his pussy before pushing down and taking it inside again.
"That's it Billy!" Santa said. "You're doing great!"
Down below, Santa gazed at Billy's soft penis. It was still like a little mushroom cap, but it was leaking. Once, when Billy almost lost his footing and slammed down roughly onto Santa's cock, the little button penis burped out a sticky white wad. It drooled down Billy's small testicles like lava, and Santa wiped it away before it had a chance to fall on his suit.
"Open your mouth, Billy," he said.
The boy did so immediately, and licked the small glob of his own seed from Santa's finger.
"Good boy," Santa said.
The feeling got better and better as Billy adjusted, as he learned to pleasure the thick cock with his bottom hole. Santa could feel his balls tightening, could feel his cock getting that tiny bit harder. He was ready.
"Faster, now, Billy," Santa said. "Try pulling off almost all the way and pushing all the way back down."
The difference was immediate. The boy was fully impaling himself, as instructed, grunting and emitting pre-ejaculate every time his tidy little bottom hit home. The boy was as fast a learner at taking cock up his ass as he was at taking it in his mouth.
The boy groaned. Another gob of white fluid burped out of his penis, too thick and chunky to be mere pre-cum. Still soft and buttonlike was the penis, yet suddenly, as if by time elapsed photography, the button grew plump and began to rapidly distend. A river of precum drooled from the tip, wending its way down the tight, hairless nutsack. Santa brushed it off, with two fingers this time, and offered them to Billy's mouth, to be licked dry.
Like a little pink rocket, Billy's penis bounced stiffly now in rhythm to his plunging movements. The chunky ejaculate became ever more copious, and it flowed quickly now as the boy approached climax. He was on the edge, right on the edge, and it was almost unbearable, that intense feeling of tension down there. In a flash, Billy's right hand met his tiny penis, and in another instant he might have fired off his load, but that instant was cut short by Santa, whose own hand shot out and seized Billy's dainty testicles, crushing them in a vicelike grip.
"No, Billy!" Santa thundered. "You are never, ever allowed to touch yourself there! You are never, ever allowed to masturbate without permission! Do you understand?"
The grip tightened around Billy's balls.
"Do you understand?" Santa shouted.
"Yes, sir!" Billy said.
"I'm very, very disappointed in you!"
"I'm sorry, sir," Billy said.
The boy squirmed. His balls were in extreme pain, and his penis shriveled back into a button. Santa's rampant cock was still firmly lodged up his backside.
Santa relaxed his grip on the boy's balls, but not all the way. He wasn't about to give Billy another chance to masturbate. He wasn't even going to give him a chance to get an erection again.
"Now resume what you were doing," Santa said, in a calmer voice, "before we were so rudely interrupted."
The pain spurred Billy on. Up and down he chugged, like a butter churn on top of Santa. Billy lifted himself almost completely off of the thick cock before slamming his bottom down again, fully engulfing the needy organ. It worked. Santa was soon breathing deeply again, and his voice dropped into low, growly tone.
"That's good," he said. "Oh yeah, Billy, keep that up."
Billy did, and went even faster, even harder, until Santa's cock felt like sandpaper, stinging his tender insides. Yet despite that pain, and despite the deeper pain in his testicles, Billy continued to emit pre-ejaculate from his soft penis. It kept flowing out in chunky white globs, lots of it, the load that would have been ejected forcefully in pulsating orgasm now merely oozing out. It coated the side of Santa's wrist, and he brought it up for Billy to lick away. The boy did so without protest, then plunged himself with renewed vigor onto Santa's thick erection.
Over and over, faster and faster, Billy's body moved like a machine whose sole purpose was engulfing the fat cock. Santa began to grunt with each downward slide, then the grunts turned to moans, and finally into bellows when Billy accomplished his mission and triggered that fat old cock into roaring orgasm. It spit fiercely deep into the tight, grasping channel, annointing Billy's tender inner flesh with a male's seed for the very first time.
Santa released his grip, but ordered Billy to stay still while his cock deflated. Even so, the flesh oozed around him and caused Santa to shudder. His belly quaked uncontrollably each time this happened, and his softening penis issued fresh little bursts of seed.
Before it could soften completely, Santa gripped his cock and ordered Billy to rise up. He quickly wiped himself clean, so as not to soil his Santa suit, and then tucked himself safely away. Billy, back on his hands and knees, waited to be told what to do next.
"Lay on your belly," Santa said
Billy did so with trepidation, fearing another spanking, a spanking he didn't think he could take after the severity of the earlier one, but Santa did not reach for his paddle. Instead, he addressed the younger man, really a boy, in a gentle but firm voice.
"Do you understand why you were not allowed to have an orgasm today, Billy?"
"Yes, sir," Billy said.
"Why?"
"Because I masturbated without permission."
"That is correct, Billy. You did it twice, didn't you?"
"Yes, sir."
"It is extremely important for boys like you not to ever touch or masturbate there penises. Extremely important."
"Yes, sir."
"You must always get permission. From a man. Sex with your wife is different. But you, as a sexual submissive, must always obey her, in the absence of a real man to obey."
"Sexual submissive?"
"Yes, Billy. That is what you are."
Billy did not respond. Santa did not like it.
"Do you disagree with that, Billy?"
A long pause. A still silence.
"Billy?"
"Yes, sir," the boy finally said. "I am a sexual submissive. I am not allowed to masturbate unless given permission."
"Good boy, Billy. You have my number if you wish to meet again. Don't be so afraid the next time."
"Do you live here?" Billy asked.
Santa laughed loudly.
"Of course not, young man!" he said. "Santa lives at the North Pole!"
"But really, are you going to be around after Christmas is over?"
"I'm afraid not, Billy. I will be gone until Christmas next year."
Billy frowned.
"Why did you want me to lay on my belly? Am I getting another spanking?"
Santa chuckled.
"No, Billy, not today," Santa said. "I didn't want you to leak all over the place. Santa filled you up real good."
Santa got up. He walked over to the pile of Billy's clothes, picked up the sparkling white briefs, and returned.
"Legs together now, Billy," Santa said.
Awkwardly, for it was no easy task with Billy laying on his belly, Santa pulled the boy's briefs up his legs. When they reached the boy's bottom, Billy gave a shreik.
"Ouch!"
"Quiet, now," Santa said.
Santa pulled the briefs over Billy's blazing bottom. The boy turned over, sat up, moved off of the bed and dressed. Before he left, he looked at Santa for a long time.
"Thank you," he said.
"You're welcome, boy. Text me if you want to meet again."
A very, very careful walk saw Billy to his car. He winced when he sat, squirmed and shifted until the pain at his bottom, and indeed in his bottom, was almost bearable, then drove away. He felt free. Free from fear, free from anxiety, free and blissfully empty. It was a light, warm feeling. It was a feeling of peace that Billy had seldom known, not since he was a child. He knew it wouldn't last.
Aprehension began to build as Will neared his apartment building. What would he tell Angela this time? A glance at his watch caused a palpatation. Seven o'clock. That was much, much later than he'd ever come home from Saturday basketball. That was much later than he could easily explain away. He felt heavy again, going up the elevator, heavy drawing out his keys and opening the door.
Angela was waiting for him. Angela looked a little angry.
"We were worried about you," she said.
It didn't feel sincere. Not to him, not to her. She wasn't worried, she merely was curious.
"Where's Henry?" he said.
"Sleeping," she said. "He exhausted himself with fussing."
"I'm sorry."
"Where were you?"
"At the gym," Will said.
"And?" she said.
An idea formed in Will's mind.
"Oh, I went and got coffee with this guy we used to know. Jimmy Engels' older brother, up from the city. I didn't realize it had gotten so late."
"Ah," she said. "What's his name?"
"John," Will said.
"Interesting," she replied. "A guy name John stopped by earlier. Big, tall guy. Wanted to know if you were okay. Said you were acting strange and ran out on him at the gym."
Will turned white as a ghost. He knew he was busted. He was about to say something, but Angela had already turned and walked away.