Note: This story uses characters from a story I wrote years ago called “The Babysitter Who Knew Too Little.” Check it out to get backstory!

Brandon woke with a start, body jerking violently against the damp sheets. He felt the familiar tension and bolted from bed, shedding pajamas and briefs as he went. He made it to his bathroom just in time to ejaculate into the sink, biting his lip to stifle the involuntary moans of satisfaction.

As think strings of semen spilled across the porcelain, he arched his body and threw his head back. He steadied himself by pressing one hand on the mirror, leaving a handprint. With his other hand, he gripped his pulsating penis, several fingers reaching back to probe his scrotum and his index finger occasionally rubbing across the swollen head, sending spasms of pleasure through his body.

Spent, he leaned against the counter, panting and shaking. After a minute, he rose and cleaned up, washing the remnants of his semen down the drain. He returned to his bedroom and retrieved his sky blue briefs. They fit snuggly, and he reveled in the pressure against his now flaccid penis.

In just his underwear, he crawled back into bed and stared up at the shadowy ceiling. Absently, he played with the line of new hair that stretched from his navel to his dense patch of pubes. Despite the calm he felt, Brandon was troubled. The dreams were getting more vivid and leaving him more and more frustrated.

He dreamed of older boys stretched out across beds – rows of boys bound and gagged with their supple bottoms bared, waiting to be spanked. Though long, tousled hair, they stared at them with scared, pleading eyes. Their sweat-slick bodies trembled with fear as he approached, testing the weight of whatever implement his dream had conjured up (sometimes a paddle, sometimes a belt, sometimes something outlandish like a tennis racket).

Usually such fantasies would satisfy him, but the glaring lack of a real counterpart to the exciting dreams was beginning to wear on him. The problem had started five years before when he and his friend Trevor had taken their sadistic babysitter down a few pegs by entrapping and spanking him. It had been a thrilling experience for Brandon. He could still recall with clarity Wesley Parker's bouncy ass as it grew hotter and hotter. It had been a surreal weekend, and the older boy's ass had been etched in his memory, down to the circle of boy-fuzz surrounding the pink hole. Of course, he still often got out the photographic evidence of Wesley's downfall when his parents had gone to the bed and the house of dark and silent. With a flashlight under the covers, he had jerked off countless times with the photos spread out before him.

When he and Trevor had ganged up on Wesley, it had been revenge for his mistreatment of the kids he babysat. They had handcuffed him to a desk, cut away his boxers, and beat his ass black and blue. Wesley had spent the entire weekend naked, serving every whim of the younger boys, and frequently finding himself bent over with his bare ass being chastised. After the weekend, Wesley had cleaned up his act, and Brandon had kept his word by not releasing the photographs or spanking the teenager again.

However, the opportunity had left Brandon with a need to spank. Trevor had sensed this and submitted to Brandon's desire for the last three years. Truth be told, Trevor had turned into a bit of a misogynist, asking to be punished and pouting when Brandon refused. But Brandon was not completely satisfied; he needed the spankee to be humiliated, helpless, unwilling. Trevor's spanking sessions never neared the intensity of Wesley's nightmare weekend. Brandon's love for his friend kept him from really letting go and unleashing the pain he yearned to.

For a long time, Brandon only dreamed of spanking Wesley. But this had given way to fantasies of lower the pants of other guys in his life and beating them.

Wesley's punishment had been warranted, and he didn't have anyone to mete out punishment to. However, at sixteen his morals were slipping and taking a backseat to desire. He needed to spank someone older and helpless, even if they didn't deserve it. With plans swirling in his head, Brandon drifted off to sleep.

Thirteen days (an almost as many late night orgasms) later, Brandon explained his new plan to Trevor with barely contained excitement. He could feel his penis swell and his entire pubic region tingle as he went through the steps.

He was sitting on his bed with his notebook in his lap, and Trevor were sitting cross-legged on the rug.

When he was twelve, Trevor had fallen in love with surfing, and his body was now lean and compact. His skin was lightly tanned which accentuated the generous freckling over the bridge of his nose and on his shoulders. His hair was sun-bleached, except for the tip which he had started dyeing bright blue. Brandon suddenly realized just how cute his friend was when Trevor cocked his head like a quizzical dog.

His brow furrowed in contemplation. “I think that will work,” he finally replied. He broke into a smile, showing off his braces. Brandon felt another stirring in his pants.

Martin Burnett climbed out of the pool, shaking the water from his auburn hair. He grabbed a towel and dried off then loosely tied it around his waist. He stretched and soaked in the warmth of the sun. With a smile and picked up his book and settled into a deckchair.

Never one for partying, he generally spent spring break at his room, catching up on reading and eating as much home cooking as possible. He had done the family bonding thing for most of the week, but now his parents had departed for few days to scout out sites for the television show they worked for.

The house was left to him and his brother who spent most of his time down at the beach. Martin liked the solitude and the leisurely way the time had passed. He had hung out with Cassie and Nathaniel all morning, playing around on the beach and boardwalk. Then had read and swam to his heart's content. Trevor had been scarce, spending time with his friend Brandon.

Brandon. The kid had certainly grown up well. He was still too lanky, but his body was filling out. Already, there were the beginnings of muscles across his torso. He kept his black hair longish and stylistically untidy. And that ass... here Martin shook his head and stopping thinking of his brother's friend.

The only thing about Brandon that unsettled the college student was his eyes. They were a deep chocolate brown and had a glint to them. It was a glint Martin had observed in the eyes of the more obsessive professors in the science department – people who spent too much time with their test tubes and Bunsen burners.

Martin's thoughts went back to his book. It was a thriller about scientists hubristically playing God and unleashing a terrifying zombie virus. Just as he became completely immersed in the plight of the lone scientist who had warned his colleagues of their mistake and his attractive female assistant, Trevor's voice shattered the scene.

“Hey!” Trevor shouted, coming out of the house in nothing but cargo shorts and a necklace. “Come play my new game with us,” he demanded. Martin glanced back to see Brandon come out after Trevor.

“Sure,” he replied.

Martin woke up sharply to a horrible smell. The last thing he remembered he was playing a video game with his brother and drinking a soda Brandon had gotten for him. He jerked his head and tried to get up. He couldn't move; this was perplexing. He yanked, but his body stayed in place. Slowly a terror rose in his chest. He realized that he was naked except for his underwear and lying face down on his bed. He was also gagged with a piece of cloth. He looked over to see his brother and Brandon grinning at him.

“Hi, Martin!” Brandon said. “You can't get out, I promise you. I know you haven't done anything wrong, but we're going to have some fun anyway. I'm not going to lie: this is going to hurt you a lot more than it does me.”

Martin's eyes bugged out.

Trevor grinned with open delight, bouncing on the balls of his feet with anticipation. He loved his brother, but sometimes hating living in Martin's shadow. His older brother was better at everything – with the exception of surfing which failed to impress his parents. He was going to enjoy this immensely.

Brandon also grinned as his eyes met Trevor's. He hooked his fingers into the waistband of Martin's white boxer-briefs. The nineteen-year-old squirmed, twisting his body the little the ropes permitted. His muffled sounds changed tone – something like a frustrated helplessness. It was just what Brandon wanted to hear, and he slowly worked the underwear down. They caught on the head of Martin's penis, and Brandon played with them at this point, allowing the elastic to move up and down the thickening shaft as he stared at the top half of Martin's bottom.

With his fingers still hooked into the waistband, he pulled back, stretching the underwear taunt over Martin's irritated penis and leaving the entirely of his bottom open to be viewed by the two sixteen-year-olds.

Martin wasn't athletic but did work out some. However, his body was much softer and curvy than Wesley's or Trevor's. Brandon knew he was going to relish the experience of spanking such a different bottom.

Martin's bottom was broad and plump. Unlike Wesley's muscular butt, Martin's was shapelier. The cheeks rose up in tow dimpled mounds, almost like separate entities. They were both covered in goosebumps and light, downy fuzz. Brandon stared, mesmerized as his victim again twisted, unknowingly moving his bottom in a way that made his tormentor drool.

Brandon was beside himself. He couldn't have asked for a better target. Martin's ass looked almost childish in its fullness. Near his legs the cheeks naturally separated a bit, showing a glimpse of the sparse hair in the crack.

After a few minutes of staring and teasing Martin's penis with pressure, Brandon let go of the underwear. It snapped back into place, leaving a pink band across Martin's ass. The bound boy yelped into his gag.

“Let's get started,” Brandon said. “Would you like to do the honors?”

“Definitely,” Trevor replied. The eagerly grabbed his brother's underwear. But instead of pulling it down, he yanked the up. Martin moaned as his penis was caught in an uncomfortable position. He could feel the fabric strain against his privates and up his crack. Both cheeks were bared and pulled apart by the white fabric wedged between them.

Trevor grabbed a length of dangling rope, entwined it in the two leg holes, and tied it to the rope securing his brother's arms in place. Almost reverently, Brandon palmed the two cheeks, running his hands all over them, resting them in his hands, digging his fingers into the deep creases where they met the legs. Martin again moaned as Brandon started massaging his bottom, grabbing handfuls of flesh and rubbing.

Without speaking, Brandon reached into his bag and brought on a red ping pong paddle. It was the same paddle he had used on Wesley and later on Trevor. Martin looked back with frightened eyes as Brandon lined the paddle up with his right cheek. Brandon lightly bounced the paddle against the cheek. Then he pulled back and brought the paddle down.

Smack

The crack of paddle against butt filled the room, followed by Martin's startled scream. Brandon and Trevor watched as color flooded into the white ass, a perfect oval of pink in the middle of the cheek. The plump flesh was still jiggling slightly.

Elated, Brandon closed his eyes and drew in a deep breath. His penis strained against his briefs. He brought the paddle up again and down on the other cheek.

Smack

“I'd forgotten how much fun this is,” Brandon said as Trevor leaned over and unabashedly felt Martin's ass.

He laughed, “It's already warm! Let's get busy.”

Martin couldn't believe this exchange. Trevor was right – already tingling pain was settling on the surface of his bottom. He mentally cursed himself. How could he have fallen into such a trap?

His thoughts were interrupted by series of smacks that brought tears to his eyes. His face was bright red with shame and shock. He wiggled, trying to evade the horrible paddle but to no avail. He was stuck.

Smack Smack Smack Smack, Smack, Smack, Smack

Brandon gleefully paddled away. Martin's ass trembled but always bounced back as if yearning for more punishment. He loved the sound of beat flesh. He loved the control and power. He loved studying the patterns of color on flesh. The middles of the cheeks were already pink with ruddy patches at the apex. He alternated cheeks – spanking first the right then the left – and working the paddle up and down them. He didn't let any part of them rest for long.

Smack Smack Smack Smack, Smack, Smack, Smack

After five minutes of continuous beating, Brandon stopped and set the paddle aside. The edges of the red skin was laced with slightly swelled flesh where the edge of the paddle and dug deep. Martin's back was slick with sweat, and a sweaty, earthy odor was coming from his crack.

Smack Smack Smack Smack, Smack, Smack, Smack

Brandon started in on the ass with his hand. He loved the feel of the flesh give under his hand, and the heat that seemed to greet and lead his hand in for the kill. When his hand was red and tingly, he stopped. “You're turn,” he said to Trevor.

He stepped back as Trevor picked up the discarded paddle and grinned evilly. In no time, the room was again full of smacks and muffled moans. Brandon watched his friend merrily found a rhythm. As he watched, he ran his hand down into his jeans and rubbed his penis through his underwear. There was already a damp spot.

Smack Smack Smack Smack, Smack, Smack, Smack

Trevor relished the feel of the paddle popping against his brother's ass. His approach was different. He concentrated a number of spanks in one area, working the flesh into a shade of crimson. He only tormented one cheek at a time, gripping the other one and pulling it out of the way. Under his hand, he could feel his brother frantically clench and shake.

Smack Smack Smack Smack, Smack, Smack, Smack

Martin was now openly weeping. He couldn't help it. He buried his face in the comforter on the bed and wetted it with tears and snot. He bit helplessly at the gag, but it wouldn't budge. He had lost count of time. As he trembled, the wedgie became more and more uncomfortable, chafing his privates and crack. Then it stopped. He held his breath, not daring to look up.

Trevor and Brandon were talking casually, but he didn't register what they were saying. He could only concentrate on the intense pain in his bottom. It radiated through his whole body.

Brandon was busy gearing up for Phase 2. He pulled out a pair of scissors and grabbed the wedge of underwear. He pulled the sweaty fabric out of Martin's crack. Martin moaned as the fabric seemed to rip at his flesh.

Meanwhile, Trevor had retrieved his digital camera and was lining up a shot that was sure to help his friend through countless nights.

“And now the unveiling,” Brandon said as he slid the underwear between the scissor blades. Several snips and camera flashes later, Martin's last piece of clothing was in tatters. Brandon continued cutting until all the pieces of the garment were scattered on the floor. Trevor dutifully chronicled his brother's humiliation.

“Now the fun really begins,” Brandon said with a grin. He held up two hairbrushes.

“Oh yeah!” Trevor exclaimed, taking one of the brushes.

“Okay, the contest is simple. The reddest cheek wins,” Brandon explained to Martin's horror. After a countdown, Trevor and Brandon started smacking the ass in earnest.

Smack Smack Smack Smack, Smack, Smack, Smack

Laughing and teasing, the two boys painted the older boy's ass a deep brick red. In places it was almost purple.

“Come on, you can do better!”

“Let a real spanker show you how it's done!”

“My grandmother spanks harder than you do!”

Smack Smack Smack Smack, Smack, Smack, Smack

Martin was close to breaking. His nerves were shot. Questions fleeted across the pain. What would they do with the pictures? How much longer? Would this ever stop?

Smack Smack Smack Smack, Smack, Smack, Smack

Brandon watched as Trevor attacked the vulnerable “sit-spot” of his cheek. Flesh bounced and redden as beads of sweat flew in all directions. Suddenly, he was overwhelmed by longing and stopped spanking. Trevor looked at him. Before he could stop, he leaned over and kissed his friend. After a startled moment, Trevor pulled away.

“I'm not... I mean... I...” he stammered.

“Oh, I mean I'm not either... I just... Let's start again,” Brandon answered.

Unfortunately for Martin, he received the brunt of their embarrassment as both blushing boys covered by intently focusing on his punishment. The hairbrushes fell fast and furious, bouncing and tormenting the teenager's ass.

Smack Smack Smack Smack, Smack, Smack, Smack

Then suddenly the hairbrushes stopped. Martin looked up. His sweaty hair hung in his bloodshot eyes. Though the hair, he saw Brandon's grinning face. “Okay, here's the deal. We have one more phase to go. I'm going to let you go, but if you try to get away, those pictures of your fat ass being beat will get emailed to everyone you know,” he explained. “You will submit to the last phase willingly, okay?”

Martin was paralyzed with fear. Those pictures couldn't get out, but his ass felt like hamburger. He could withstand anymore, but he had no choice. He slowly nodded. As his bonds were cut, he burst into tears again. The humiliation was too much. He slumped on the bed as he felt his gag being loosened.

“Please, guy!” Martin cried through his sniffles. “No, more. I can't... I c... c... can't handle...” his voice trailed off into deep sobbing.

Brandon slapped his bottom hard. “None of your whining,” he said. “Now I want you to get down on your knees and kneel down with your head on the ground.

“I can't... You can't!” Martin screamed, his raspy voice cracking. He ran for the door.

“Pictures!” Brandon yelled. Martin stopped.

He turned around, cupping his hands over his privates. He looked ridiculous standing naked in front of two younger boys. He slumped his shoulder and slowly got down on his knees. With one more pleading look (which was met with sneers), he bent his head to the ground.

His entire ass was spread out to the boy's attention. This revealed the pure white skin previously hidden in the crack. As the boys stared, Martin's hole clenched and unclenched as if in anticipation. Martin's hole was a baby pink and surround by wispy hair. Brandon had a sudden desire to dart his tongue over it, but he had already had too much discomfort today with his impromptu kiss.

Brandon reached into his bag and pulled out one more item – a wooden spoon. He and Trevor got on their knees on either side of the weeping teenager. Without speaking, he smacked the head of the spoon right down on the sensitive hole.

Martin screamed in pain. Snot bubbled out of his nose and tears poured down his chapped face. Trevor put an arm around his brother's waist, holding him in place as Brandon worked the spoon up and down the crack, reddening the skin to match the rest of the punished ass.

Despite the earlier discomfort, he smiled lovingly at Brandon's handiwork. Martin writhed in his hold, but he kept the teen in place. He looked at his handsome friend who was elated as he tormented the puckered slit.

Finally, Martin seemed entirely spent, and Brandon stopped. They had spent almost an hour blistering the plump ass. Trevor and Brandon rose, leaving Martin sobbing on the floor, his ass still thrust in the air.

“We'll be in my room,” Trevor said. “Go there after you get cleaned up.”

With one more smack each, they left the room. Martin unsteadily got to his feet. Hundreds of thoughts clamored in his head, but he couldn't focus on anything but his bottom.

The punished flesh seemed to pulsate with pain. His butt cheeks must have swollen; when he attempted to walk, they slide against each other, intensifying the throbbing. Slowly, he made his way to his bed and laid down on his stomach, fighting back tears.