Michael's Internet Challenge

by Tasty Little Pop Tart

Copyright© 2019 by Tasty Little Pop Tart

Erotica Sex Story: Michael lets David talk him into the latest Internet challenge. It is for young boys, specifically 14-year-olds, like Michael. Completing the challenge means getting paid $1000, or more. Failing is unthinkable. Failing means having your entire challenge released to the Internet unedited, with your identity intact. The challenge is to take a Rambone all the way into your rectum while doggie on your friend's bed, naked. Will Michael do it?

Caution: This Erotica Sex Story contains strong sexual content, including mt/mt   Reluctant   Gay   Heterosexual   Anal Sex   Exhibitionism   First   Sex Toys   Voyeurism   .

“Oh, my God,” he moaned. “It’s so big!”

Writhing, Michael twisted his hips, adjusted the curve of his spine, drew his knees closer together and then spread them farther apart. Nothing helped. The monster up his ass had his breathing labored, his heart pounding against his rib cage. “Fuck, David! Why’d I let you talk me into this?”

Laughing, David patted his shoulder. “Relax. I told you you’d like it. And you’re done now.”

Michael gazed up at him, disbelieving. “It doesn’t feel done! The thing is bigger than a beer can! It’s 3” wide! Do you know what my asshole feels like, right now?”

David stifled a snort. 8” of immense dildo stuck into the air from his classmates rear end. The shaft was actually 2-1/2” thick where it passed through Michael’s asshole. 6” of shaft filled his engorged rectum.

“This doesn’t mean I’m queer!” he protested. “You remember that!”

David nodded sagely. “Of course, you’re not, Michael. Shit,” he muttered, realizing he’d used Michael’s name again. So much editing to do. Michael blurting his name in pain a minute ago. Giving his full name to the fucking camera earlier. Jesus.

“Fucking Internet challenges!” Michael muttered.

The crazy challenge had spread like wildfire. Restricted to 14 year boys--specifically boys within a week of their last birthday--the challenge set the participants height and weight, his grade-point average, his eye and hair color, and how big his penis was, fully erect. The boy attempted the challenge nude, in his best friend’s bedroom after school on a Tuesday afternoon. The dildo dimensions were set at 2-1/2” diameter, with a 14” long shaft. The brand could only be Rambone, the model number D346543. The price online: $79.90.

“Jesus Effing Christ,” Michael moaned.

Michael was tiny: 5’2” tall, and 102 lbs soaking wet from the shower. His eyes were baby blue, his wispy hair blonde. His complexion was Scandinavian, cheekbones prominently high. He’d bore freckles galore in the summer. He been an honor roll student forever. He fit the challenge parameters like a latex glove. Thank God the huge Rambone was polypropylene.

“Holy fucking shit!” he complained.

The whole thing was filmed. The challenge allowed editing to obscure faces, remove identifying marks, blank the use of names, and alter easily identified voices. David had suggested the challenge a week ago; Michael reacted violently.

“Are you crazy? Put a fucking dildo up my ass? A fucking Rambone!” he clarified stridently. “I’m not gay!”

David had snickered. “No one’s saying you are. It’s just you fit the challenge parameters like they were written for you, Michael. Specifically. And you turn 14 this weekend!”

“Hell no! Not another word, or you can stick our fucking friendship up your ass!”

Nothing further was said until Michael turned 14 on Saturday. David gave Michael two presents: one everyone saw, the other only Michael laid eyes on.

“Are you fucking insane? Get that thing outta my house, David!”

David walked over and closed the blinds. No one would see this beforehand but Michael. He grinned as Michael fumed, red-faced and humiliated. “Someone from Blake should try it.”

“You try it, dammit! I told you no!”

David laughed. He fit the parameters like OJ’s famous glove. He stood 5’9” and weighed 162 lbs. Michael excelled academically; David at sports. David had a cock 7-1/2” long, though Michael didn’t specifically acknowledge that fact. He’d only ever seen David erect by accident, and always at great embarrassment to himself. It embarrassed him more that David thought nothing of Michael seeing his erection. Michael barely tipped 4” on his best day.

Sunday, Michael told him no again. Monday, David didn’t ask, though Michael remained red faced and fretful all day. Tuesday morning, he preemptively said no on the bus, admitting in frustration that it was this afternoon, or never.

David laughed. “How in the hell would anyone know? It’s not like you hold up your driver’s license to prove your age, which you don’t even have, Michael.”

Michael looked ready to melt. “You’re supposed to show your student ID. Blank out your name and picture and where you go to school and all that.”

David canted his head. “How do you know that?”

Michael blushed a furious red. “Because I went online to look last night. I got...”

“Curious?” David suggested.

Michael’s face only got redder. “No!” he hissed. “Yes. I just wanted to see.”

David eyed him patiently.

“If I do this, no one can ever know!”

“Of course not,” David agreed.

“It has to be today.”


“I’m gonna show my Blake ID to prove I’m 14 and 3 days.”

“OK,” David said again, eyebrows furrowed.

“What?” Now Michael looked ready to explode. He was certainly the color for it, brick red.

“It’s just that...”

“What!” Michael insisted furiously. “Now you don’t want me to?”

David shook his head. “I’m not sure I want to share that with anyone else, is all.”

Michael blinked at him, slack-jawed. “Oh. OK. Does that mean... ?”

“I don’t know what it means,” David admitted uncomfortably. “I gotta get to class.”

No more was said until David opened his front door at 3:15 p.m., and ushered Michael inside. “We have 3 hours to do this. Mom gets home at 6:15.”

“What about Jen?”

David shook his head. “I probably won’t see her until 8 o’clock. She works part time at the mall.”

Michael knew that, had forgotten in his extreme anxiety. “Jesus. I don’t want to do this, David. I’m scared,” he added at David’s sideways glance. “This doesn’t mean I’m queer,” he insisted, though both suspected the truth of that claim. “Not everyone who wanders, is lost,” he misquoted. He’d read that on a bumper sticker just that afternoon. David nodded.

“You want something to eat? A Diet Coke?”

Michael existed on Diet Coke. He vehemently shook his head. “Let’s go upstairs. Right now, before I chicken out. Im gonna...” Words choked off, he grabbed the banister and started the climb to David’s bedroom on the 2nd floor. He looked ready to do what his voice had failed to express. David followed him up.

Dropping his backpack on the floor, Michael immediately went to the window and closed the blinds. David turned on the lights. His backpack joined Michael’s on the floor. “Michael, you don’t have to do this.”

“Where’s the Rambone? I hope you got it hidden crazy well.”

“Of course, I do,” David said. “It’s in Jen’s closet.” He laughed at Michael’s bug-eyed reaction. “It’s in my closet, dude. I’ll get it.”

“No!” Michael blurted. “The rules say no one but the contestant can touch the thing before you ... you... ?”

David watched him blush that furious brick red. “It’s on the shelf on the right side, hidden behind the X-Box carton.”

Trembling visibly, Michael went in the closet and stretched onto his tiptoes to reach the shelf. “You have to film this,” he said, remembering.

David pulled out his IPhone and turned it to landscape mode. Grinning, his expression rightly a grimace, Michael again stretched up to retrieve the Rambone. He paused, blinking.

“What about lubricant?”

David laughed at his agitated expression. “Behind the box. I bought it the same time as the--” He broke off as Michael’s expression turned horrified. This was becoming real to him. David, also.

“No one will ever know it’s you, Michael.”

“I’ll know!” Michael objected, a little hysterical-looking. His voice was two octaves higher than normal.

“We’ll work on it together after school. On my MacBook.”

“Fuck we will!” Michael screeched in his soprano voice. “I’m never looking at that thing! At myself in it! With that thing up my behind!”

David thought Michael might throw up. “Easy, Michael. You don’t have to do this, you really don’t.”

“Will you stop saying that! Of course I have to do this! I’m the perfect challenge contestant! You said so yourself! Now, will you please start over and let me get on with this shit? We’re running out of time!”

David started again, filming Michael walk into the closet and stretch onto his tippy toes. “Hi. I’m Michael Collins. I’m 14 years and 3 days old, and I’m taking the Rambone challenge with my friend David. This is his closest, and this is the Rambone he bought.” Michael displayed the 14” long monster. “He bought this to make it all possible...” He held up the large tube of KY Personal Lubricant. “ ... because we all know how well this thing fits my 14-year-old asshole and rectum. I’ll be using a lot of this during the challenge, I think. Oh, look ... he bought 2 tubes.” He brandished the 2nd with a strained grin. “How thoughtful!”

David stopped filming.

“What?” Michael demanded hotly.

David tapped his toes and waited patiently.

“I’m a little stressed out! Can you blame me? Fuck!” he exploded, hurling the dildo at David. “This was your idea, David! Don’t make fun of me, asshole!”

Fuming, he turned his back and hunched his shoulders. David didn’t mention how much like a girl he’d looked throwing the dildo. How much he looked and sounded like a girl now. He wondered how Michael would look out of his clothes. He hadn’t really considered that yet ... or his possible reaction.

They began again. This time Michael did better, keeping to the proscribed introduction, remaining under control. He looked by equal measure excited, anxiety-ridden, aghast, and humiliated. He knew within minutes he’d be naked on David’s bed, inserting a monster cock up his ass. Down, in truth, as he’d be extreme doggie, ass high in the air, spine deeply bowed, chest flat to the mattress. David handled the actual insertion. Michael took it like a porn star, hands pulling his cheeks apart. This aspect frightened him most: looking inescapably queer, inviting it into his rectum. Part of the Rambone challenge, inescapable.

Michael carried dildo and lubricant out to the camera. “Model number D346543. Price online: $79.90. 2-1/2” thick, 14” long, exactly as prescribed. I don’t think they care about this.” He fingered the tubes of KY lubricant. “I’m glad you got ‘em, though.” He cleared his throat, blushing all over again. “Here’s my school ID.” He fished the card from his back pocket and held it for David to film. “I’m a freshman at William H. Blake High School. You can see by the date...” He pointed it out at the bottom. “I turned 14 three days ago, on Saturday. I’m 5’2” tall...”

David listened as Michael ran down the list of qualifications. He grinned as, brick-red, Michael confessed to his 4” shortcoming in the erection department, and his correspondingly miniature peanuts. “Hey!” he objected furiously. “I’m a tiny little guy! What do you expect!”

David couldn’t help laughing. He stopped filming as Michael fumed. “Calm down. We’ll edit it out. You’re doing just fine, Michael.”

“Fuck. Let’s get this over with.”

Placing the dildo and KY on David’s nightstand, he introduced the bed. “David’s bed. This is where I’ll take the challenge this afternoon.” He looked ready to self-immolate. “I--” He cleared his throat. His voice cracked as he continued. “I guess I’ll take off my clothes now. Then I’ll get on David’s bed in doggie position--” He stared at David plaintively, looking on the verge of tears.

“Go on,” David advised softly.

“ ... and...” He cleared his throat loudly again. “And David will put the dildo up my behind, while I hold my cheeks apart to make it easier to penetrate me. I understand it will hurt--” He stamped his foot girlishly and balled his fists, bared his teeth in a grimace.


David kept filming. This part had to be stated. “Just say it and get it over with, Michael. It’ll be fine. You know we’ll make it in.”

“I don’t know that! And if I don’t, everyone in the world will see my face, and watch me fail the challenge! Those are the rules, David! Every single student at Blake will see me attempt this!”

David kept filming. “Calm down. Rules mean nothing if you get through this successfully, which you will. Easy as pie, Michael. I promise you.”

“You promise?” Michael pleaded. He sounded exactly like David’s sister.

“I promise I will successfully insert the Rambone up your ass. All the way in. Far as it will go into your rectum. What happens after that... ?” He shrugged. “You only have to fill your rectum to complete the challenge, Michael.”

Michael looked like Mt. Pinatubo probably did a second pre-eruption. He might feint any moment, David thought. He gulped. Then he nodded. “Still filming?”

“Still filming,” David concurred. “Have to have this. Have to.”

Michael sighed. “OK.” He deliberately addressed the camera. “Per the challenge rules ... if I unsuccessfully attempt the challenge, all footage of me will be released in an unedited version onto the Internet, for everyone to see. I hereby agree to this condition, and continue with the challenge.” He shuddered violently, head to foot. “Do it,” he said gruffly. “Get it over with.”

David opened the Rambone Challenge App, linked Michael’s intro video, and entered the special acceptance code. The Challenge committee now had control of his iPhone. From this point on, Michael was at the mercy of his anatomy.

“I can’t believe I’m doing this.”

David mounted his iPhone to a flexible mini-tripod and set it down to record. He’d use Michael’s iPhone for closeup shots. Live action shots. Reaction shots of Michael’s face, as needed. It required a second acceptance code. Michael entered it, tight-lipped. “I don’t believe I’m doing this,” he muttered disgustedly.

David’s camera recorded continuously. It recorded now, and couldn’t be stopped without killing the phone. The phone would never turn on again. Michael’s phone could be used at will, but the camera fed direct to the Internet via the app. Michael was live right now.

“This doesn’t mean I’m queer. I’m doing it for the money.”

Participants pocketed a minimum $1000.00 for completing the challenge. Whatever happened next, earned the participant more. Michael could theoretically pocket $10,000.00 if he ... Michael didn’t want to think about that. He’d never even discussed it with David. He supposed that would come next. Fucking Internet challenges.

“I guess it’s time to take off my clothes.”

David raised Michael’s phone and pressed the Video button.

“I’m gonna take off my shirt now.” He unbuttoned his shirt and removed it to reveal his slender, surprisingly feminine chest. His nipples and areola were girlishly pink. David tried not to eye them.

“Challenge rules state that I have to narrate everything I do. So, I’m taking off my shoes now.” He toed each and kicked them away. Frowning, David eyed the oddly feminine design of the Skechers. “I’m taking off my socks now,” which he did, and dropped atop his shoes. He hesitated, stress obviously building toward panic. “You sure my camera’s filming? I don’t want to do this again, David.”

David eyed the ringed red square and nodded. “My camera is recording, regardless.”

“Can you check it?” Michael asked anxiously.

David watched him fidget as he checked his iPhone. Michael nodded in thanks. He took a deep breath.

“OK, now for my pants.” He unzipped and removed them with difficulty.

Don’t fall down, David thought. At least you wore boxers, he thought. Michael stood apprehensively in his underwear. A few seconds from now, he’d be naked and live-streamed to some pervert’s website. Fucking Internet challenges.

Michael took a deep breath and fingered his waistband. Should he chicken out, or pull a major blunder like forgetting to narrate his moves, everything to this point would go live. His classmates would know he’d signed up to do the Rambone Challenge. Everything depended on Michael staying in check, suppressing his panic at having sex with a dildo completely nude. David silently prayed.

“OK. I’m taking my underwear off now, and I’ll turn around to prove myself completely nude.” He did, twirling awkwardly in place. Even disjointed, his movements looked decidedly feminine. David shifted uncomfortably, aware of his stiffening boner. Michael naked turned him on.

Michael shivered and erupted in goose flesh. He rubbed his biceps convulsively. No one could miss his intense state of sexual arousal. His manhood pointed like a miniature spike. David had never seen him erect before. He stared at his friend in fascination. Pitifully small, but fascinating, despite that.

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