The fading light of the summer day settled gently through the open upstairs bedroom window. It was a warm evening, but not sticky with humidity. Nathan was at his desk absentmindedly fondling himself while watching something on his laptop. He had the house to himself, as the rest of his family had gone to see a movie that did not interest him.

Before he realized it, Nathan was fully hard and stroking himself.

After reaching under his waistband for better access to his growing need, Natan redirected his browser to a site more adult in nature. The sex cam website loaded and once he had navigated to the side of the site with men, his precum started flowing. He watched a few guys show off, usually older and hairy, but he found himself wanting something different.

Nathan decided to click the ‘Start your Cam’ button on the top of the site. He had excitedly signed up once he was old enough but always got too nervous to go live. Tonight was going to be the night. He closed his window and blinds, angled his webcam down away from his face, and clicked the broadcast button. 

A little chat window came up to the side of his video feed and Nathan watched messages pop in. He suggestively played with his bulge and spoke to the guys in his chatroom. The attention was getting him excited. It wasn’t long before the messages telling him to get naked convinced him to take it all off for the guys watching his show. 

“You guys want me to do what? Take my shorts off,” he teased, tugging down the waistband of his shorts. He chuckled at the responses and then stood up pushing his chair back. Nathan slid the shorts down slightly, exposing the top of his pubic mound and his closely trimmed bush.

“Is this what you all want?” he continued to taunt the viewers, inching his shorts lower and lower. The base of his cock was showing and he gave a little dance toward the camera. His computer chimed which caught Nathan by surprise. He shuffled closer to his monitor, trying to keep his shorts up while he investigated the notification. Someone watching the show had sent a tip! Had he left that feature on? He felt ice in his veins realizing he wasn’t just showing off but showing off for money.

“Oh hey, sorry I didn’t mean for this to be that kind of show–” Nathan started but then a few more came in. All of them with messages encouraging him to strip and to ‘show hole.’

Nathan wasn’t sure what to do, but he let his little head do the thinking for him. He dropped his shorts and twisted his hips in a way that swung his circumcised cock in a circle. The messages started to fly by on the screen, he could barely read them before they had scrolled past. He remembered someone had sent him money to see his ass, so he turned around and showed off the slightly fuzzy peach. Nathan shook his ass toward the camera. Bending over his chair he spread his cheeks to show off his tight hole. He heard a few more alerts and decided to turn back around. The viewers had gotten pretty suggestive asking him questions and giving directions.

“Alright, guys I’m gonna sit back down so I can see what you’re all saying,” Nathan said, sitting and stroking his cock in full view of a chatroom full of horny guys. He decided to field a few questions while jerking.

“Yeah, I am eighteen.”

“No, I’m not a virgin.”

“Well I haven’t been fucked yet, but I want to try it.”

“I guess I’m vers, It’s all pretty new to me. But I have topped someone!”

“No, I’m not lying...actually it just happened earlier today.”

“Yeah, I can tell you guys about it.”

“No, he was older than me.”

At this point, Nathan had his left leg up on the arm of his chair, one hand stroking his cock and the other teasing his hole. Guys were asking him to do all sorts of naughty things in the chat. One of the men was persistent in asking him to find some kind of toy to put in his ass. Nathan liked the idea of being told what to do, especially with all these different men vying for his attention.

“Ok PrinceDon, let me grab a toy,” he got up and walked over to his dresser to get the vibrator and lube he hid under his socks. It was supposed to be a gag gift from a classmate for his 18th birthday, but the orgasms he got from it were no joke. He got back into his chair and put his feet up on the desk so he could get a better angle to show and tell. He rubbed the tip of the dildo against his puckering pink hole and taunted the chat.

“Is this what you want?” he teased. “This toy probing my boyhole?”

A very large tip popped up on his screen from PrinceDon. Nathan was floored by the value and aroused by the message.

“For $100 shove that toy deep in your boy pussy and tell all of us horny men about the guy you fucked today.”

Nathan felt dirty and hot and wanted nothing more than to do what he was told. He grabbed the lube bottle, squeezed a big dollop of clear jelly onto the dildo, and rubbed it along the length with a finger. Once the toy and his finger were nice and slick Nathan placed the toy on his desktop and slid that finger into his hole.

“Oh fuck guys,” he moaned as his first and second knuckle slid into his entrance. He pushed it deep inside and twisted his finger to get the lube deep inside him. 

“Yeah, you guys like that?” Nathan cajoled the chat room as he slid the finger in and out of his hole. He pulled his index finger out of his asshole and lined up his middle finger to slide in alongside it. This stretched his sphincter and he groaned low in his chest at the expansion. Normally this was a tight squeeze for him but the arousal at the guys virtually egging him on and paying him to perform sex acts must have awoken a submissive side in him. He knew he could easily fit a third finger in but decided to give the guys, and specifically PrinceDon, what they wanted.

“Alright guys, I think I’m ready,” He moaned as he extracted his fingers from his winking asshole. He grabbed the toy with his other hand and aimed at his hole. The tapered head easily slid into him and he let out a higher-pitched moan as it penetrated him. He shuddered and paused with the toy about halfway inside him. He wasn’t even watching the chat room anymore, just enamored with the pleasure he was giving himself.

“Ohh that feels good,” his eyes rolled before he remembered the other half of the instructions. “Right, I’m supposed to tell you guys about my first time. Sorry…I got dickstracted.”

“You guys probably won't believe this but, the guy I hooked up with was a teacher of mine… No, I’m not lying. I had to go by my old school to drop off some stuff and I ooohh,” Nathan paused in the recounting as he slid the pink plastic penis fully inside of himself. 

“Fuucck,” he moaned, eyes closed as the flared base pressed against his opened hole. “I had to drop off some stuff and I ran into him, uhhh, like knocked, huh…him over,” Nathan moaned around the story he was trying to tell while gently sliding the toy in and out of his ass.

“I noticed he was hard and I waaaas tooo. I was embarrassed but then we encountered each other again in th-the bathroom later. He offered to help me relieve my stress and took me into the teacher’s lounge.”

Nathan opened his eyes a little to see messages flying by in the chat window. 

“Fuck that hole boi” - DomDaddy4Bois

“Ride it” - BiCuriousCuck

“SHOW FEET” - Footluvr

“Then what happened?” - PrinceDon

“look at this boy slut” - chsr4chsr

Nathan’s cock twitched in response to the dirty messages and the thought of these men watching him fuck himself with a dildo. His cock was dripping precum and twitching without him touching it. He felt the familiar feeling of his balls drawing up tight to his shaft and slowed the pace of his self fucking, he had the rest of the story to tell.

“So he took me into the teachers' lounge and put me on a desk and sucked me off. UGH, normally uh I don’t cum that quickly, but when I tell you guys I had been dreaming about this man for the past two years. And his mouth and tongue were like magic. He fingered me a little and then sucked my soul through my cock, I basically passed out after.”

At this point, Nathan decided to free his hands. He lifted his feet off the desk and slid the toy out of his hole. He squatted over his chair and placed the dildo beneath his ass and lowered himself onto it. He slowly rode the toy.

“After that, I woke up in his lap and decided to return the favor. Hh-he taught me how to suck his cock, it was fat and eight inches long. He had a bunch of foreskin. I was gagging on it but he coached me through how to please a guy without choking. I tried to finger him like he did me but then he put his ass in my face and I had to taste it.”

“Before I knew what I was doing I was fucking my teacher,” Nathan continued the tale to his virtual audience. “I was balls deep in his big hairy ass. I didn’t even put on a condom. Ughhh, his hole was hot and soft and it let me in so easily. He was loving it and begging for my young cock up his old teacher ass.”

Nathan’s self-control had slipped and he was bouncing on the dildo. He huffed and groaned, fighting the urge to touch himself, something told him he had to ride the load out of his cock. His balance temporarily slipped and the switch of the vibrator caught on the seat of his chair and the toy began to buzz inside of him. Nathan swore and moaned high as the vibrations tickled and teased him from within.

“Fuck, oh fuck guys I turned it on,” Nathan moaned to the chat room full of men. His hard cock was bouncing up and down flopping against his slight belly and the seat of the chair, sending strings of precum flying. He squatted down on the toy fully and kept it there. His cock was electric and tingling. The memory of his first fuck is at the forefront of his mind. 

“I was ready to cum again and I tried to warn him because I was riding him raw. But he wouldn’t let me pull out. He used his legs to hold me inside him. He begged to shoot my load in his hole. I bread my teacher for my first fuck.” 

The satin vice of his teacher’s fuckhole, twitching and gripping him. The memory of his teacher forcing him to breed sent Nathan over the edge. He heard the man’s voice in his mind, “Keep it in! Please shoot your hot load inside me, boy. Breed your teacher's big ass.” 

Nathan shouted in pleasure and slammed down fully on the toy as his cock erupted a hot load of cum. He sent ropes forward and he knew he should aim but couldn’t help himself. The orgasm took hold of his senses, he bounced, swore, and shot cum. He heard more tip notifications come in and that sent another shudder down his spine which hit his buzzing prostate and pushed another volley of cum from his teen cock.

As Nathan rode the orgasm of his life he felt the ground under him shake. It took a moment to register that this shaking wasn’t the earth-shattering orgasm he was having but instead, the garage door opening as his family arrived home. His eyes snapped open as the pleasure evaporated.

He jumped up off the toy in haste and lost his balance. He knocked down the chair and fell backward, sprawling out on the floor of his room. He shoved the chair out of the way and scrambled up to his laptop to shut down the cam show. He noticed a rope of cum had coated the keyboard but didn’t have time to fix that. He mashed the power button until the screen turned off. 

Nathan snatched up a towel from the floor, wiped what he could, and then sprinted off toward the shower. 

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Peter Donaldson was having a quite pleasant evening in the study of his suburban home. He was lounging back in his softest robe and comfy slippers. He had a snifter of Whisky in one hand and his cock in the other. His large computer monitor showed a studly boy bouncing on a pink vibrator. The boy was amateurish but Peter was enthralled by his performance and the raunchy story he told. 

He placed the snifter down, picked up the cigar from the ashtray, took a pull of thick sweet smoke, and blew it at his monitor. Tugging at his pierced nipples Peter teased himself while the boy recounted his story. He swapped the cigar back for the whisky and brought it to his lips.

“Fuck, oh fuck guys I turned it on,” the boy cried out over the cam show. Peter gripped his cock tight and took a sip, letting the peaty liquid languish on his tongue for several moments before he swallowed. 

“He used his legs to hold me inside him. He begged to shoot my load in his hole. I bred my teacher for my first fuck.”

That sordid detail abruptly ended Peter’s edging session as his cock shot a thick rope of cum up onto the nest of gray fur on his chest. He panted and groaned cumming to the teenage boy on his screen. As the waves of pleasure subsided Peter took a finger and scooped some cum off his chest and into his mouth. He saw the boy was still going, riding the toy and cumming. He wanted to thank the boy for his wonderful performance and sent in another sizable tip. 

He grabbed the soft cloth from the side of his desk and began to mop up the thick load from his hairy body. The cam show was still going and Peter heard a thud and some cursing, he looked back to the monitor and saw the camera footage was empty. The webcam focused on the wall in the background and Peter saw a Kelly green pennant flag with white lettering that read Bear Valley High School. 

Flabbergasted Peter pressed a key to maximize the video to double-check that it was his school’s flag on the wall he saw. As he read the flag for the fourth time the face of Nathan Anders blocked his view. He smiled in recognition in the brief moment before the web feed went offline. Well, the boy had a lovely body, he thought, and would go far as an adult performer. A thought nagged at the back of his mind. 

“Wait, which teacher?”

Peter slammed down the whisky glass splashing some of it onto his desk as he reached for his cellphone. He tapped on the screen to call his recent contacts and put the phone to his ear. It rang just once and then it was picked up.

“Jameson?” he grunted into the microphone.

“This is he,” came the voice on the other end of the line.

“I’ll need today’s security footage on my desk first thing in the morning,” Peter demanded. His tone crept into anger.

“Yes Principal Donaldson,” Jameson replied. “I’ll start on it now sir.”