How Far Would You Go?

Drool soaked Michael’s chin and shined the dick sliding in and out of his mouth.  Ackles’s hands held his head immobile, fucking his face with slow, steady strokes.  Welling’s monster dick pumped in and out of Michael’s ass at the same pace.  Michael’s jeans pooled around his ankles and he could only hold onto the arm of the couch, the hundred-dollar bill crumpled under his hand, as both ends were filled simultaneously.

He hadn’t expected to end up the whore of the night when Welling and Ackles had shown up at his trailer with cases of cold bottled beer in both their hands.  He’d finished filming another ridiculously stupid scene and had been killing time until his flight back to LA.  They’d appeared a couple hours before he had to leave, with matching grins and gleams in their eyes, wanting to celebrate wrapping the worst episode of the season so far. 

“Why do people watch this show?” Ackles was sprawled beside Michael, his thumb hooked in his belt loop.  The couch butted against the back wall of the trailer and a large gap stretched between it and the desk where a table once stood.  Several empty beer bottles gathered at their feet.  “There’s no logic behind any of the episodes.  People can’t jet off to foreign countries on a whim.”

Welling was straddling the desk chair, a beer dangling from his fingers.  “The audience doesn’t expect us to be a smart show, just a pretty one.”  He flashed a Colgate smile.  “And we’re very pretty.”

Michael opened another beer.  His head was buzzing lightly from the alcohol, but at least he’d be relaxed for the flight.  “Pretty won’t put money in our pockets in the future and neither will shilling crap.”

“We don’t get paid enough now to shill this crap,” Ackles said, sipping from his own beer.  “I don’t know how you guys put up with it for so long.”

“Everyday is like playing a never-ending game of ‘How Far Will You Go?’” Welling said. 

“Playing what?” Ackles said.  The wind whipped against the trailer outside.   Michael got up to lock the door, so it wouldn’t blow open.

“You know, what’s the least amount of money it’ll take for you to do something nasty,” Welling said.  “Like, I’d eat a dog biscuit for free, but dog shit would cost a grand.”

“A thousand?” Michael laughed and dropped back onto the couch.  He lit a cigarette.  “I’d do it for a hundred.”

“I’d probably do it for a hundred, too,” Ackles said.  He smirked at Welling.  “Wuss.”

“I’d lick up vomit for a hundred,” Welling said.

“Yours or someone else’s?”


“Gross.”  Ackles chuckled and drank more beer.  “I’d, um— I’d drink piss for a hundred.”

“We’re already drinking piss,” Michael said, holding up his beer bottle.  Welling and Ackles laughed.  Michael smirked.  “I got one.  I’d fondle a dog for a hundred.”

“You are so nasty,” Welling said, pointing at Michael in emphasis.  He paused to drink his beer, and then asked with a grin, “Male or female?”

Michael waggled his brows.  “Either.”

“I’d fondle someone who looked like a dog for a hundred,” Ackles tried to one-up.  He put his empty bottle on the floor with the others.  “Male or female.”

“Dude, if it led to sex, I’d do that for free.”  Michael took a drag off his cigarette and reached for an ashtray.  “I’d always have sex for free.”

Ackles picked up the challenge.  “What about a fatty?”


“A hooker with crabs.”

“Give me a condom and I’ll fuck her up the ass.”

“Bet you wouldn’t do a guy for free,” Welling said smugly.

Michael shrugged, blasé.  “If I’m doing the fucking.”

“And what if you were the one being fucked?”

“Are you offering Welling?” Michael said with a lascivious wink.

Welling smirked.  “If I was?”

“I’d definitely charge you,” Michael joked.  “You make more money than me.”

“Would you charge me, too?” Ackles said, bumping his knee against Michael’s.

Michael took a final drag off his cigarette and chased it with the rest of his beer.  He made a face at the bottle, his head swimming slightly.  “I’d charge you for making me drink this crap beer, first.”

“A hundred bucks.”

“What?”  Michael stabbed out his cigarette.

“A hundred bucks, to let me and Welling fuck you.”

Michael snorted.  “Yeah, right.”

Ackles pulled his wallet from his back pocket and took out a hundred dollar bill.  He held it out to Michael with a daring smile.  “How far will you go, Rosenbaum?”

Michael took the bluff.  He snatched the hundred from Ackles as he stood.  He Luthor-swished around the side of the couch, rucked up his t-shirt, bent over the arm, and stuck out his ass.  “Who wants to be sloppy seconds?”

Ackles exchanged a look with Welling that Michael couldn’t read and rolled up to his knees on the couch.  Michael lifted his chin and batted his lashes at Ackles.  He heard the clink Welling’s beer bottle on the desk as he blew Ackles a fawning kiss.

Ackles smirked down at Michael and his hands moved to his button-fly.  Michael arched his eyebrow tauntingly, wondering how far Ackles could get before wussing out.  He nearly jumped when he felt a touch on his waist, but dropped easily into his role of ham and wiggled his ass at Welling.  “Come on, big boy,” he said in a throaty falsetto.  “Give it to me, baby.”

The buttons on Ackles’s jeans opened with a flick of his wrist and he pulled out his dick.  Michael smiled, disguising the tension that ratcheted suddenly inside him.  Ackles was hard.

Welling’s hands circled Michael’s waist and worked the snap and zipper of his jeans.  Michael clutched the arm of the couch, the hundred dollar bill crumpled beneath his hand, as Welling drew his jeans down.  He stiffened when he was unmistakably groped.  “Welling?”

Welling embraced Michael from behind, and what felt like an iron rod covered by denim rubbed against Michael’s bare ass.  “God, Michael,” Welling whispered in his ear.  “This is going to be so good.”

Michael inhaled sharply and glanced up at Ackles.  This had to be a joke.  They were going to laugh in his face if he panicked now.

Ackles crept forward on his knees and rubbed the head of his dick against Michael’s lower lip.  Michael focused on Ackles’s taunting face.  He was not going to let them get one over on him.

He stuck his tongue out and licked Ackles’s dick.

Ackles hissed.  Michael stopped himself from squealing and running away, but just barely.  He’d licked another guy’s dick!  Fuck, he’d drunk too many beers.

He started to laugh at his own reckless, alcohol-prompted behavior when Ackles’s dick pushed past his lips.  He jerked and was stopped by the hand on the back of his head.  His eyes flew open wide as Ackles adjusted and braced Michael’s head between his palms and began thrusting his hips.

Ackles’s dick stroked a short way into Michael’s mouth.  The flare of the dickhead bumped against Michael’s teeth on the rock back.  Michael exhaled noisily through his nose, his lips stretched around Ackles’s girth.  There was no way this couldn’t be classified as a blowjob.

And that was a finger touching his asshole!

Michael tensed as Welling’s wet finger probed him.  Welling rubbed his other hand in circles on Michael’s lower back.  “Mnmm!” Michael exclaimed around his mouthful. 

“Let me in, Michael,” Welling said, pushing his finger against Michael’s clenched asshole.  “This will be so good.  I promise.”

“Maybe he can’t take it,” Ackles said, thrusting a little deeper into Michael’s mouth.  “Maybe he wants to wuss out.”

Michael definitely had too much to drink, because his dander rose at the goading.  He knew he could take anything dished out and then turn around and do it better.

Welling’s finger pressed insistently at his asshole.  Michael let him in with a defiant glare at Ackles.  Ackles chuckled as Welling crooned, “Oh yeah, that’s it.  Let me open you up.”

It felt bizarre having fingers up him that didn’t belong to a doctor.  Michael gripped the arm of the couch a little harder and exhaled heavily at the stretch and slight burn.  He drooled around the dick in his mouth.  He swallowed the excess saliva and Ackles moaned and jerked his hips.  Ackles’s dickhead bumped against Michael’s upper palate and Michael tasted bitterness.  He recognized the flavor of pre-come from tasting his own in the past.

Michael grunted when he felt a more painful stretch of his asshole and closed his eyes.  Welling was actually finger-fucking him, while he blew Ackles, in his trailer on the Smallville lot.  He’d had this dream before, but it usually involved him, Allison and Kristin on the couch.  Allison had such great ta-tas and he had a standing bet as to how wild Kristin was in bed.

“Jenson,” Welling said.

Ackles pulled his dick out of Michael’s mouth and Michael slurped obscenely.  His lips were sore in the corners and jaw hurt a bit.  Ackles’s dick bumped Michael’s chin as he was tugged forward and rested his forehead against Ackles’s abdomen.  The stitched hem of Ackles’s t-shirt scratched his skin.

Michael knew what was going to happen next, when Welling’s fingers disappeared.  He tensed, staring downward at the ugly orange and brown weave of the couch cushion.  Was he really going to allow Welling to fuck him?

Welling’s dick pressed against his asshole and Michael’s heartbeat sped up in panic.  “Relax, Michael,” Welling said, cupping Michael’s hip.  “Pretend you’re taking a shit and push against me.”

“Fuck, what am I doing?” Michael said, and bore down. 

His body seized in pain as Welling’s dickhead popped into his asshole.  He bit down a cry, clenching his teeth.  He pressed his forehead hard against Ackles’s abdomen.  Tears stung the corners of his eyes.  It was like a knife had been stabbed into him.

Ackles’s rubbed his shaved head soothingly, while Welling massaged his thumbs around his clamped asshole.  “It’ll feel better once you relax,” Welling said.

“How can anyone relax with an iron pole up their ass?” Michael ground out between his teeth.  “Fuck.”

“Just keep pushing against me,” Welling encouraged.

Michael sucked in several deep breaths and bore down again.  Welling slid deeper inside.  He felt as if he were being torn in two.  “Jesus, fuck.  Gay people like this?”  

Welling laughed, causing him to rock in and out slightly.  “The first time always hurts.”

“You could’ve warned me.”

“We wouldn’t be doing this,” Welling thrust further into Michael, “if I had.”

Michael grunted and dug his fingernails into the arm of the couch. 

“This is his first time?” Ackles said.  His dick jumped and hit the underside of Michael’s chin.  “Sweet.”

They fell silent, the only sound being Michael’s pained breathing.  His body adjusted around the dick filling his ass, which wasn’t as wide as Welling’s fingers had been but somehow felt more monstrous.

Welling began to move, drawing back to the dickhead and then sliding in again.  His hands held Michael’s hips, as he set a slow, steady pace.  Michael exhaled with each thrust in, accepting the stretch and pain.  He had no idea how gay men could enjoy it.

Ackles fingers slipped around under Michael’s chin and he urged Michael’s head up.  Ackles grinned jovially and pressed his dickhead against Michael’s mouth.  Michael opened his mouth wider, taking Ackles in.  Ackles cupped his hands on either side of Michael’s head and fell into rhythm with Welling.

The paper of the hundred-dollar bill scraped against Michael’s palm as he braced his hands better.  How far would you go?’, he heard Welling say in his mind.  Apparently, he’d become a gay whore for a C-note.  Either that, or Six Beers Queer wasn’t just an urban legend.

Michael drooled around Ackles’s dick, closed his eyes, and imagined the picture he made, being tag-teamed by two fit men.  They’d probably make a lot of money in the porn industry, if it were being taped.  Welling and Ackles certainly had stamina.  Michael’s jaw ached and he was getting a crick in his neck.  His ass burned and throbbed with the beat of his heart. 

Welling’s rhythm faltered, finally, and his fingers tightened on Michael’s hips.  His thrusts sped up.  Ackles fucked Michael’s face a little faster, too, and Michael figured he was enjoying Welling’s decent into orgasm.

Welling made a sound like a helium balloon deflating and shoved as deep as he could into Michael.  Michael felt Welling come, dick pulsing inside his ass.  It was wild, and really, really weird.

Welling slumped against him, breathing heavily.  “Fuck, Michael.  I knew it would be great.”

Michael would’ve answered waspishly if his mouth wasn’t full of dick.

Ackles slowed his pumping, sliding his dick almost lazily between Michael’s lips.  “My turn.”

“Yeah,” Welling panted slightly.  “Okay.”

Ackles removed his dick from Michael’s mouth and climbed off the couch.  Michael worked his jaw and slurped drool.  He could feel Ackles’s hands holding his head still, even though he’d let go.  If Michael had bruises…

“Ow.  Shit.  Fuck.”  Michael cursed, scrunched his eyes shut, and gritted his teeth, as Welling pulled his dick slowly from Michael’s ass.  It hurt.

Something brushed against his cheek, and he opened his eyes as Welling sat on the couch.  His glistening dickhead poked above the waistband of his underwear. 

“Hey,” Welling said, cupping Michael’s jaw.  He leaned in and began kissing Michael sloppily: licking drool from Michael’s chin, sucking hard on his lower lip, thrusting a tongue into his mouth.

Ackles stuck his dick inside Michael with a moan.  “You broke him in good.”

Michael was broken all right: broken in the head.  His ass was fucked again while Welling played kissy-face with him and he was letting it happen.  What else had been in those beers?

Ackles didn’t last long, which made sense considering he’d fucked Michael’s mouth for ages as a prelude.  Welling was still molesting Michael’s mouth with his tongue when Ackles finished. 

“Where’d you toss your condom, Tom?” Ackles said.

“Garbage can under the desk,” Welling said and sucked on Michael’s lower lip some more.  He half-pulled, half-urged Michael around the arm of the couch.  Michael kicked over several bottles as he was yanked onto Welling’s lap.

“Yeow!” he howled when his ass hit Welling’s thigh.  He arched his hips and bit the inside of his cheek at the sharp pain radiating from his asshole.  He heard Ackles laugh and gave the finger in that direction.

“Here, scoot down a little,” Welling said, manhandling Michael.  Michael cracked open an eye and shot him a dark look.  “Put your butt between my thighs, so you’re not sitting on it.”

“This is great,” Michael said sarcastically, adjusting himself across Welling’s lap.  He leaned against the arm of the couch, his ass hanging between Wellling’s thighs, his jeans tangled around his ankles.  “How will I ever repay you for making my ass feel like it’s been through the meat grinder?  Wait, I know.” 

Michael slapped the hundred-dollar bill against Welling’s forehead, hard.

Welling took the hundred, crumpled it up, and tossed it at Ackles above Michael’s head.  “Hand me that,” he said, pointing to something.  Ackles did.

It was a pocket-sized tube of KY Jelly.

Michael narrowed his eyes.  “You planned this, didn’t you?”

“Fuck, yeah,” Ackles said from behind him.  The cap clinked as another bottle of beer was opened.  “We’ve been working for days on a way to bone your ass.”

Welling flipped open the top of the tube and squeezed some of the clear gel into his palm.  “I came up with idea to dare you into it with that game.”

“And I bought the beer,” Ackles said.

“You two are—fuck.”  Michael clenched his hands on his thighs, as Welling started jacking him.  His head dropped back as his dick came to attention.  He let out a moan.  “You’d better keep doing that.  You owe me.”

“No problem,” Welling said in a deeper than normal voice, and Michael rolled his head on his neck to look at him.  Welling stared at Michael’s dick as he jacked it.  He licked his lips.

Michael’s mind delved into a fantasy involving Welling’s fat lips wrapped around his dick and shuddered in excitement.  He opened his mouth to demand it and released another moan instead when Welling did a twist-buff move with his wrist giving his dick paroxysm of joy.  Welling’s fingers wrapped around him just tight enough, getting him off with strong, quick tugs.

He rolled his head again, resting his chin on his chest, and looked down his body.  He watched his shiny dickhead poke in and out of Welling’s grip.  The skin on his shaft slid with the strokes.  He leaked pre-come from the reddened tip.  The slick sounds of the lube added to the hotness of the handjob.

He felt his balls draw up and his hips moved in conjunction with Welling’s jacking.  Orgasm rested on the rear of his tongue.  He dug his fingers into his thighs, his breathing becoming ragged.  The cords in his neck stretched tightly and he grunted with the strain for release.

His eyelids slammed shut when he started coming with a jagged sound in the back of his throat.  He shot onto Welling’s hand and his own legs and abdomen.  His body shuddered hard in pleasure, as Welling milked him dry.

Welling let go of him when he became too sensitive.  He was wearing a very stupid grin when Michael opened his eyes.  Michael might have to slug him after he caught his breath.

Welling shifted under him and Michael felt his renewed erection press against the side of his leg.  Michael looked at it a moment, then looked at Welling.  “You don’t think you’re going to fuck my ass again with that thing.”

“No.”  Welling touched Michael’s lower lip.  “I’m going to fuck your mouth.”

“Pull back his legs for me,” Ackles said, dropping to his knees beside the couch.  He set a pillow on the floor beside him.

“Now, wait a minute.”  Michael’s protest fell on deaf ears, as Welling lifted Michael’s legs up and back, with Ackles’s help.  Michael was curled with his sore asshole exposed.

“This will make you feel better fast,” Ackles said, and pressed the mouth of his half-empty beer bottle into Michael’s asshole.

“Hey!”  Michael felt cold liquid pouring into him.  “What are you doing?!”

“The alcohol will absorb right into your bloodstream,” Ackles explained.  “You’ll be drunk and feeling fiiine in no time.”

“God, that’s kind of hot,” Welling said, staring intently.  “I think I have a kink.  I wouldn’t mind watching you fuck him with the bottle.”

Ackles grinned devilishly.  “Slick it up and I will.”

“Oh, no.  No, no, no, no, no.”  Michael pushed his legs against their hold.  “Ass-virgin here.  Vanilla sex only.”

Welling pouted.  Ackles finished emptying the bottle, popped it out, and patted Welling’s knee.  “We’ll wait until the alcohol hits and try again.  In the meantime…”

“In the meantime,” Welling repeated, and slipped out from under Michael.  Ackles put the pillow under Michael’s ass and they lowered his legs. 

Michael hissed when his ass touched the pillow, but it was much better than the scratchy cushions.  “What are you going to do to me now?” 

Welling pushed his jeans and underwear down his thighs.  His dick flopped free, curving erect from his pubes.  He hoisted his leg over Michael and straddled him on the couch.  One foot on the ground, the other knee depressing the cushion by Michael’s shoulder, Welling rubbed his dick along Michael’s cheek.  “I want to fuck your mouth.”

Michael had given up his ass and mouth already to these two, as was their plan.  He could call it off now without being called a wuss or losing face.

Welling’s bangs hung over his eyes, as he stared fixedly on Michael’s lips, brushing the tip of his dick back and forth against the seam of Michael’s mouth.  “Michael…”

Michael licked his lips and the tip of Welling’s dick, and opened his mouth.  Welling slipped inside with a dirty moan.

Ackles fingers tugged Michael’s balls and Michael moaned.  Welling cursed and thrust deeper into Michael’s mouth.  His dick was a thinner but longer than Ackles’s, and Michael nearly gagged.  He breathed out his nose and adjusted his head on the arm of the couch.  He kicked off his jeans and spread his legs, giving Ackles more play room, and brought his hands to Welling’s ass.  Welling braced a hand on the back of the couch, the other on Michael’s head, and started fucking Michael’s face.

The buzz of alcohol tingled along Michael’s spine and filled his head.  Ackles’s hand closed around his semi-soft dick and toyed with it.  He remembered then, for some reason, as Ackles was stroking him back to fullness, that he had a flight to catch. 

Welling screwed his hips and murmured, “I can’t wait to watch you get fucked by that bottle.”

Of course, it didn’t look like he’d be able to sit on his ass anytime soon.  But the next time someone asked him how far he’d go, he’d demand better beer first.


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