Ryan's Dilemma

by Matt2670

Copyright© 2019 by Matt2670

Erotica Sex Story: 16 year old Ryan is on his hands and knees, naked at 1:34 in the morning. His outraged asshole wants to know why the head of a Dick Rambone has it stretched almost to breaking, with 13" of shaft to follow. Not that Ryan is mad-anxious to know what 14" of cock thick as a beer can feels like inside him. Boys will do unusual things, however, if offered enough money.

Caution: This Erotica Sex Story contains strong sexual content, including mt/mt   Consensual   Reluctant   Gay   Heterosexual   Humor   Anal Sex   First   Masturbation   Sex Toys   Size   .

Dedicated to my favorite author, Angie E, also known on SOL as Tasty Little Pop Tart

Saturday, February 9, 2019, 1:34 am

This was fucking crazy, he thought. Panting, and trembling with adrenaline/testosterone shock, Ryan looked back over his shoulder and shook his head. He could not believe he’d impaled his bottom on a fucking Dick Rambone dildo. This was just crazy.

It was 1:34 am, according to the alarm clock on his nightstand. He’d turned the clock to face him before offering his asshole to the dildo. The head was inside him, gripped tightly by his disbelieving sphincter. He was the asshole, he thought.

Reaching out, he fumbled the bottle of Heineken, and then swigged a big mouthful. He’d ensconced the bottle in one of his dad’s ridiculous beer bottle sleeves. It kept the bottle surprisingly cold. He downed another big gulp.

He was alone, the condo his until Sunday afternoon. Mom, Dad, Hillary, Olivia, and Hannah had gone to visit Grandma Constance in Columbus. He had a cache of bodacious dope with plenty of papers, and a case of Heineken in the fridge. Mom told him he could drink 3 beers a night and not be in trouble. Ryan was 16 years old. His birthday was two weekends ago.

“This is fucking crazy,” he mouthed. “What kinda 16 year old boy fucks a dildo with his ass?”

A crazy, horny one, he thought.

Though naked and partly mounted to a huge black phallus, Ryan didn’t consider himself queer. He’d never sucked a cock, never had one up his ass, nor kissed a boy. True, he wore his sister’s underwear and outfits on occasion, but what 16-year-old didn’t do that? He watched videos at night of boys getting their butts fucked and gobbling big cocks, but that only meant he made his own path through the woods, rather than follow everyone else. He was independent, not queer.

He’d smoked 2 joints and downed 4 beers. He didn’t care if his mother ragged on his ass on Sunday. He intended to have a really fun weekend.

“Are you okay?” Connor asked.

Ryan sighed. “You sure we’ll get paid for this, dude?”

Connor stopped recording. “He already gave us $1500. He paid for the dildos and both these cameras. He paid for the Heineken we got in the refrigerator, and the ounce of dope on the bed over there.” Both looked at the stash longingly. “He promised $3000 for this video, sight unseen, dude.”

Ryan grumbled something unintelligible.

“He also said we could walk away from this if we wanted to, no broken bones.”

Ryan chuckled disgustedly.

It bothered him having a fierce hard-on with a giant cock in his ass. The idea of sliding back on the huge black shaft until it disappeared completely inside him made his balls ache inside his shriveled scrotum. What possessed him to sign up for this?

Ryan stood 5’7” tall and weighed 125 lbs. He was physically developed from years of playing sports. He was cute, with stylishly shaggy blonde hair, and blue eyes. He’d been naked before Connor only once, only slightly pushing the boundaries of their non-sexual relationship. They beat off together in the afternoon sometimes after school watching porn, and had even stroked each other’s cocks in mutual masturbation. Sometimes they even made each other ejaculate by mutual agreement. On the face of it, neither boy considered this queer behavior. Regardless, events of his birthday colored everything a darker shade of red.

Ryan said: “Has it occurred to you, we aren’t normally adjusted, 16 year old boys, Connor?”

“Whaddya mean?”

Flustered, Ryan gazed at him in irritation. “Dude ... I’m naked. I have a cock up my ass. If I get it all the way inside me, and fuck the damned thing like the guy wants me too, we get to split $3000. If I give you a blowjob while I’m doing it... ?”

Connor winced. “I thought that was out.” He cocked his head. “I thought you said no sex, Ryan.”

“He joked about paying me to fuck a dog, Connor. He joked he’d pay me $10,000 for that privilege.” His face grew red. “It wasn’t entirely a joke, either. Just like me gobbling your cock while I fuck the dildo, wasn’t a joke. Just like his saying I’d look good with your cock up my ass, Connor.” He flinched and cut his eyes away a moment.

“The fact he even suggests stuff like that means he doesn’t see me as a normal 16 year old boy, either.” He shook his head slowly. “I’m only 16 and 14 days old, Connor. I’m not normal. I’m a fucking pervert.”

Connor sat the camera on Ryan’s desk. “I gotta tell you something dude...”

“What?” Ryan said.

“Seeing you like that, even though we talked about this a hundred fucking times...” He unsteadily shook his head. “I don’t think I’m normal, either, Ryan.”

Ryan gazed at him warily. “I’m not sucking your cock, Connor. You can forget that, right now.” He shifted uncomfortably on the huge head in his asshole. He wondered why he kept it in his ass, anyway. It was perverted.

“I didn’t expect it to turn me on like this,” Connor said, “but it does.”

The guy with the money and a penchant for 16-year-old’s had contacted Connor a month ago. Connor was 2 months older than Ryan, and was instructed not to engage Ryan in the scheme until he turned 16. That happened on Saturday afternoon, January 26th, two weeks ago.

“Dude, we gotta talk,” Connor had said.

Ryan was intent on disabling a maneuvering Iranian tank. “About what?” he said.

“Someone hacked your computer, dude.”

That got Ryan’s attention. He paused the program, running on his brand new Xbox One.


Connor lowered his voice almost to a whisper. “I saw the videos you downloaded of the middle school kids.” He looked unexpectedly disturbed. “Dude, that stuff’s patently illegal. Where did you find it, anyway?”

Ryan was red-faced, scared and embarrassed. He never thought to lie about it, though. Instead, he jolted upright and stumbled across the room to his bedroom door and locked it. Looking back, he gulped loudly and croaked: “What guy are you talking about? When did I get hacked? Why are you looking at shit off my computer for, asshole?”

Connor had expected the flare of rage. “He also showed me the history from your browser, dude...” He grinned salaciously. “Dude, you like seeing boys get fucked and sucking cock an awful lot, don’t you?” He held up his hand. “It’s okay. I’m cool with that stuff. What I don’t understand is your interest in boys and dogs.”

Ryan flushed bright red and looked away. For the past 6 months he’d watched and occasionally downloaded illegal videos of boys and dogs having sex. He’d discovered a series of videos featuring the same twin brothers, his age, having sex with each other, other boys, and numerous big dogs. The twins were blonde, blue-eyed, tall and slender with embarrassingly fetching cocks and delicate testicles. Watching them 69 and take each other up the ass drove him nuts with craving. Many other videos were worse, indescribable on these pages.

“I’m being blackmailed? I got no money!” he protested, panic-stricken. “I’m only 16!” His eyes suddenly bulged, and his complexion turned dangerously sallow. “He’s not blackmailing me for sex, is he?” Fright nearly made him hyperventilate. “Jesus, Connor! What am I gonna do if he wants sex?”

Connor shook his head. “He’s rich and famous and not interested in getting his cover blown.” He held up his hand. “He sent me something to give you.”


Connor dug a flash drive from his front pocket. Ryan balked as though it might be a miniaturized nuclear weapon ... or a dog collar he’d wear the rest of his life. He backed against the door, shaking his head.

“It’s nothing to get in a panic over, dude.”

Terrified, Ryan shook his head.

“It’s just some dude riding a really big dildo with his asshole.”

Ryan flinched in embarrassment. He’d watched a series of videos on xHamster exactly like that last weekend. Watching the queer fuck a black dildo 14” long on his hands and knees made him apoplectic. He’d exploded three times watching the videos.

“‘Riding my Rambone,’ “ Connor recited. “The guy said to tell you that. It’s what he wants you to do on video for him. He said he’d pay you to do it, Ryan.”

Ryan gawped, appalled.

“He said he’d pay you do other things too.” He grinned rather sheepishly. “You don’t want to know all the details, believe me.”

Ryan shifted restlessly on his hands and knees. It bothered him so much more to be naked with a humiliating boner in full view of his friend, than being attached to the fat black dildo. “I don’t know how anyone does this,” he complained. “It’s fucking impossible.”

He unwillingly glanced at his friend’s strained crotch. Connor was bigger than him, 7” to Ryan’s 6”, and noticeably thicker. Connor had what Ryan considered an intimidating cock: thickly veined, bruised looking when erect, the head small, lending it a menacing appearance ... designed for rape. Ryan had uncomfortably imagined it in his mouth and rectum many times. His feelings for Connor sometimes scared him.

“Do you want me to suck you, Connor?”

Startled, Connor blinked rapidly and backed a step against the corner of Ryan’s desk. “Do you want to?”

“Do you want me too?”

Connor stared at his friend’s exasperated expression. “Well, yeah ... I’ve always wanted you to, Ryan.” He flushed with embarrassment. “I don’t particularly want to have you do it now, though.” He flushed deeper. “Not when you’re all messed up on weed and alcohol and have a cock up your ass like that.”

“It’s not up my ass!” Ryan complained stridently. “I’m only holding it with my asshole, dammit!”

The ridiculous distinction made both boys blush deeper red.

“How’d we get into this fucking mess?” Ryan complained. “Turn the camera back on and let’s make some money, dude!”

His rectum could not possibly hold the entire dildo. Overall, including the vital suction cup on the end, the phallus measured 16-1/2”. The shaft was 13-1/2” long, and 2-3/8” wide at head and base. His rectum bottomed out at approximately 7” depth (according to Google, anyway), which left 6-1/2” unaccounted for. He knew in order to ride the entire length, the head needed to bull past the 90 degree bend into his sigmoid colon. He knew it could be done; the question was, did $3000 cover the torture involved?

Make that $1500, he reminded himself irritability. Connor got the other half.

He speared his friend with a look.

“What?” Connor objected.

“Nothing,” Ryan muttered, shifting restlessly again.

At least his asshole had grown used to the massive head stretching it wide open; he guessed a monster hemorrhoid was in his near future. Why did he talk himself into this, anyway? He squirmed uncomfortably on the head, feeling ludicrously girlish and queer.

“Do you think I’m queer for doing this?” he asked.

Connor winced at his pleading expression. “I think you know the value of $1500, dude, and the additional money to be made from this guy.”

The words failed to quell Ryan’s embarrassment. “Would you do this for $1500?” he asked petulantly.

Connor lowered the camera. “I’m not being asked to, Ryan. The guy likes you, not me.”

“That doesn’t answer the question!” Ryan shot back. He already knew the answer, which only made his humiliation worse. “I have to be queer to even consider wrapping my asshole around this fucking pig!” He gave a resentful thrust backward onto the head, which only brought a grimace and a hiss of pain.

“Fuck!” He lowered his head, shook it angrily, grinding his teeth. “This is so messed up!”

Connor replaced the camera on the desk. “We should ask for more dough.”

“Ya think!” Ryan spat. The head was an inch deeper in him now, which only heightened his embarrassment and fueled his anger. Why had Moneybags chosen him? Why had he idiotically said yes? How had Moneybags zeroed in on his hapless victim?

Why did he like watching boys have sex?

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