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Conning Colin: A Gay Romantic Comedy by Elsa Winters, Brad Vance (24)

Henry

Henry held onto the strap on the 6 train, staring absently at the ads for cheap dentists and trade schools that lined the subway car. He liked to spend this “zone out” time on the subway with his noise-cancelling earbuds in, thinking about… stuff.

And as much as he tried to think about his screenplay, what he needed to write next, it wasn’t happening. His mind kept going back to last night with Colin.

He had never, ever bottomed for a client. He’d had lots of requests for it, sometimes shyly, sometimes arrogantly, but his answer had always been a pleasant but firm no.

The rule had given him things he needed – it had kept “Hamilton” in control, not just physically (and in this job, you didn’t really want to put yourself beneath a stranger’s hands if you could help it) but psychologically. Hamilton was the top, the dom, the upper class, the ruling class. Once someone could fuck you in the ass, he thought wryly, there wasn’t much else they would be shy about asking for.

And, bottoming was something he’d kept for himself, for his own pleasure, and as part of the firewall that separated Henry from Hamilton. When Henry was getting fucked, he was always Henry. When he was fucking, even for pleasure, there was a tendency to let Hamilton do the driving, especially with strangers, if only because he was so good at pleasing men with his advanced skill set.

So why had he let Colin fuck him? It hadn’t come about the ordinary way, that was for sure, no conversation, no negotiation. Colin the actor had just suddenly inhabited the role of a top, a gentleman speaking to his valet, master to servant, and Henry… Hamilton… both of them had responded enthusiastically to the scene, totally fucking turned on. He believed Colin was a gentleman and a top, had always been one, had always fucked his valet with the absolute assurance that his requests for blow jobs would be joyously accommodated.

And Colin was such a fast learner! Henry had read Colin’s hesitation before penetrating him, his uncertainty about what to do, and Henry had Mrs. Robinson’d that inexperienced dick right where he wanted it, had made Colin fuck him just the way he liked it.

Before the appointment, Henry had resolved to double down on Hamilton, to harden the mask, to tighten the reins, to bet the Virginia Horse Farm he pretended to come from that he could firmly and permanently steer Colin away from the truth of Henry.

And in the morning, he’d done just that – woken up, exchanged blurry pre-caffeinated civilities with Colin, showered, knocked back a cup of room service coffee, dressed and left, all as Hamilton, his high finish and bright smile in place the whole time.

And Colin hadn’t done what Henry had feared, hadn’t taken advantage of last night’s events to try and change the dynamic between them, hadn’t started acting like they were… something other than provider and client. Colin had been just as friendly and polite as he had, and they’d given each other a chaste goodbye kiss and Hamilton had walked out, the mask falling as Henry walked down the hall, trying to figure out what the fuck had just happened.

It was almost as if… No. Yeah. Go on. Almost as if he’d been disappointed when Colin had been as businesslike as himself. As if he’d hoped Colin would say, what?

They’d crossed a bridge last night, no doubt. And Colin, he could have marched an army across it this morning if he’d wanted to, laid claims on Henry and Henry might have just waved a white flag and acquiesced to all of them. Which was the most disturbing part of all.

He laughed to himself, and was studiously ignored by the other strap-hangers. I’m the hooker with a heart of gold, falling in love with my customer.

It wasn’t true. He was stunned, and yeah, pleased with how good it had felt. But why had he been both relieved and disappointed this morning when Colin hadn’t done what Henry had steeled himself against? When Henry had actually, for just a moment, hoped they could both stop pretending to be someone else.

* * *

And honestly, the timing couldn’t have been worse. He was on his way to Cameron’s studio, to film the final, the ultimate “Dillinger” scene. At last, at last, the Most Str8 Dude In NYC was going to consent, for a big pile of cash, to get his dick sucked on camera by another dude.

The story arc had left thousands of paying customers exquisitely frustrated long enough, gay dudes jerking off to a video of a straight guy jerking off. Unlike other porn sites that featured “straight boys,” the men on Cameron’s site never sucked a dick onscreen, ever. It was the site’s appeal – once you took a dick, after all, how straight were you?

“Hey, sorry I’m late,” Henry said to Cameron as he flew in the door, breathless, tearing off his suit at Superman speed.

“Late night?” Cameron asked, knowing Henry would only be in a suit in the morning for one reason.

“Yeah. My regular. It was… a weird night. Not bad, just…” Henry shook his head. “It’s gonna take me a few to turn into Dillinger this morning, is all.”

“Don’t sweat it, your co-star’s late, too. Delays on the 5 train,” Cameron added as he adjusted the lighting around the bed.

“There’s a shocker.” Henry paused. “So, favor to ask. Can you put on some gay porn and dub in the sound of the straight porn?”

Cameron grinned at him. “Really wore you out last night, huh? Yeah, if you need that extra stimulation, we can do that.” His brow furrowed. “Can you stand the sound of the straight porn? I can run gay porn on your TV but have the…”

Henry winced. “Please, no. Screaming orgasmic women are going to do some serious damage to my erectile function today.”

“Okay. I can add a track in post with the screaming orgasmic women.”

Henry sighed. “Thanks.” He dug out his raggedy Mets t-shirt, as soft and thin as a t-shirt can only be when you’ve worn it for a decade, or bought it made that way for $80. He put on paint-stained jeans, grey-soled white tube socks, and pulled Dillinger’s now-trademark Von Dutch trucker hat down so his eyes were half hidden.

He looked at himself in the full length mirror, getting into character. There was something about Dillinger that turned Henry on, a lot. Just looking at “him” in the mirror, as if he was someone else, inhabiting a body like Henry’s but not Henry’s. Would Henry cruise him on the street? Oh yeah. Would he turn and look back if Dillinger held his gaze? Hell yeah. Would he get hard at the thought of sucking the chrome off the straight man’s bumper? Fuck yeah!

It was why Dillinger was the most successful character on the site: Henry had taken one of the objects of his own desires and became it, knowing that what he desired was what so very many other men wanted, too.

Henry was disappearing into Dillinger, his cock starting to throb both as Henry (turned on by the stranger in the mirror) and as Dillinger (the queasy thrill of knowing he was about to get sucked off by a dude). He sprawled on the bed, watching the gay porn on the monitor as Dillinger would, watching another dude getting sucked, seeing the look of drugged pleasure on the top’s face and thinking, A mouth is a mouth, right?

It was working out for him, the bottom’s late arrival. And Cameron picked up on it, like an astute director. He checked his phone when it chimed, and started filming.

“You nervous, Dillinger?”

“Nah,” Dillinger grunted, his hand passing over his crotch, adjusting a swelling package.

“You don’t care what your buddies are gonna think, seeing you get blown by a dude?”

Dillinger’s knowing, cockeyed grin charmed the camera. “Shit, if they’re watching this, they’re the ones who are fuckin’ gay, right?”

“Or they’re thinking about doing a shoot for us.”

Dillinger nodded. “It’s good money, man. ‘Specially when you’re gonna be jerkin’ off anyway.”

The recruitment drive over, Cameron moved on. “Your cocksucker is on the way up right now, you ready?”

Dillinger’s hand stayed on his package this time, kneading it. “Fuck yeah. I haven’t jerked off in three days, like you said.”

A flicker crossed Henry’s mind – Henry had blown an epic load last night, so he wasn’t sure whether or not Dillinger would be able to do the same. Cameron’s White Whale was a cum shot the likes of which hasn’t been seen since the 1970s, when young studs were able to shoot huge gouts across the room. Nobody was quite sure why porn stars couldn’t pump ‘em out like that anymore.

There was a knock on the door, and Cameron turned the camera to it. He answered the door and the young contest winner came in, with a natural hesitance.

“Hey, Stefan, come on in.”

Thanks…”

This guy wasn’t a pro. Cameron had run an essay contest (submitted with a photo, of course) for would-be deflowerers of Dillinger’s gayginity. He and Henry had sifted through over a hundred qualified applicants (and hundreds more for whom, well, hope sprung eternal). Henry had zeroed in on Stefan right away.

“That guy. That’s the kind of guy Dillinger would six-pack,” Henry said definitively, referring to the old (wishful) joke that the only difference between a straight man and a gay man is a six pack of beer.

Stefan was in his early 20s, with dirty blond hair, wide green eyes, and a slim smooth body. He had the kind of looks that remain boyish into a man’s 40s. He’d been given Cameron’s standard caveat about probably never getting a job in banking or whatever if he did porn, the Internet is forever, et cetera. Stefan didn’t care, since he worked in high-end streetwear marketing, where having been in a porno was probably a plus on his resume.

“Hey,” Stefan said tentatively to Dillinger.

“S’up,” Dillinger replied, his eyes not leaving the monitor and the porn.

“Go ahead and get comfortable, Stefan. You ready to suck some straight cock today?”

“Y… fuck, yeah,” Stefan said, stripping quickly.

“Awesome. Get to it, man.”

Stefan crawled up the bed between Dillinger’s legs. He undid the buttons on Dillinger’s jeans, and Dillinger arched his hips to let Stefan pull them down.

“Oh fuck,” Stefan whispered when Dillinger’s half-hard cock flopped out. Cameron moved to the side of the bed to get the shot of Stefan putting his hand around its fattening girth and stroked it slowly, amazed.

“That’s it, get the feel of it. You ever been jerked off by a dude, Dillinger?”

“Yeah, sure, when I was a teenager. Circle jerkin’ and shit.”

Feels good?”

“Fuck yeah,” Dillinger said, encouraging Stefan. He finally looked at the young man who’d been staring up at him adoringly. “Put your mouth on it.”

Stefan had his lips wrapped around the shaft before the sentence was complete. Cameron came in for a close up, Dillinger’s soft sigh signaling his approval.

Dillinger wanted to put his hands on the cocksucker’s head and shove his dick down that throat, but Cameron had told him to let things take their course. You could see Dillinger’s desire to do it as his hands rose, moved towards that head, then settled back down again.

“That’s right, just let him suck it, let him get used to that big fucker.”

Dillinger was hard in no time, and Stefan started really sucking it now, taking an inch at a time, then two, teasing the shaft, his eyes on Dillinger’s face, slack now with pleasure.

“Suck my dick,” he growled, impatient, his hands flying now to the back of Stefan’s head, pushing him down on it, thrusting up at the same time, careless of Stefan’s pleasure or comfort.

Stefan choked as Dillinger’s head popped into his throat, but he was a trooper, and Dillinger stopped, without withdrawing, to let the gag reflex pass. When it did, he thrust again, rough, demanding, Stefan nothing but a receptacle. The look on his face was cruel, and the camera lapped it up, the snarl, the hot reckless desire.

“Fuckin’ take it, o yeah…”

“Mmggphh,” Stefan replied, several times, before Dillinger let him go and he flew off, gasping for air, the camera on his red sweaty face, his eyes glittering with lust.

“You like that shit?” Dillinger muttered, putting his fingers in Stefan’s mouth, fishhooking him.

“Fuck yeah!” Stefan said around the hard rough fingers.

Dillinger pulled them out and slapped him, lightly, testing to see what his response would be. “You like sucking straight dick, don’t you?”

Stefan’s response was “Fuck yeah!”

Dillinger slapped him again, a little harder. “Fuck yeah what?”

“Fuck yeah, sir!”

“Take that shit down your throat,” Dillinger commanded, and Stefan had little choice when Dillinger took control.

“You like that, Dillinger?” Cameron asked. “Getting blown by a dude?”

“Oh hell yeah, man. Gotta get a little rough with him to get off, though.”

“You okay with that, Stefan?”

“I love that shit,” Stefan slobbered.

Dillinger was up on his knees in a flash, fucking Stefan’s face, embedding himself deep in his throat, then pinching his nose till he turned red and the gags got too intense.

He let Stefan off his dick for just a few seconds, a couple gasps of air, then it was time for another thrust, and another. This time he pushed in and out, letting Stefan breathe, but he kept his hand on Stefan’s throat, tightening the hole as he fucked it.

Cameron pointed the camera at Dillinger’s face just in time for a shot that would launch a thousand loads. Dillinger’s snarling persona suddenly disappeared, a look of shock on his face, of recognition as he looked down at Stefan, and then the pure astonishment a man feels every time the pressure inside him mounts and mounts.

“Let’s see it, man,” Cameron reminded him. “Let’s see you blow that fuckin’ load. Stefan, get ready, dude, here it comes.”

Dillinger reared back on his haunches, the tension of it adding to the power of his building orgasm. His eyes remained riveted on Stefan’s face as he jerked his dick, so unbelievably turned on by it that you’d almost think he was, you knowgay.

And at last, Cameron was rewarded, his quest fulfilled, by a 70s level cum shot, the first spurt arcing over Stefan’s head, and the next splattering his eager face, until Dillinger shoved his dick into Stefan’s mouth to dump the majority of his load inside his hungry receptacle.

His balls finally emptied inside out, Dillinger fell backward on the bed, exhausted. Stefan fell by his side, glowing, clearly chafing under his strict orders from Cameron not to jerk off.

“How was it, dude?” Cameron asked his no-longer-entirely-straight star.

Dillinger grinned. “Fucking amazing.” He put a big-brotherly hand on Stefan’s head and tussled his hair, and the bottom looked up at him adoringly, and on that Cameron faded to black.

* * *

“That was insane, dude,” Cameron said, counting out the bills to Henry after Stefan left. Dillinger had stayed in character the entire time he was there, just to make sure Stefan wasn’t tempted to spoil the illusion with a tell-all posting on the Internet.

“Yeah,” Henry said distantly.

“What’s wrong?”

“Not wrong, just…”

The truth was, and Henry couldn’t avoid it, the look of surprise on his face when he came wasn’t just the standard omigod I’m gonna cum surprise. In that moment, he realized why he’d selected Stefan, why he’d gotten so hard for him, and why he’d shot so spectacularly.

The young man wasn’t a dead ringer for Colin, but he was definitely in the running.

And what did that say about Henry, about what was going on behind the mask, when the type it took to get him off was suddenly the same as Hamilton’s best client?

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