I’ve had a few messages about this series, mostly queries or requests about upcoming stories. Perhaps the most common is whether I’ll write about the biggest cock I’ve ever had. Don’t worry—I will get to that in due course, and believe me when I say it’s a doozy. But I’m going to sit on that one for now (so to speak), and instead I’ll share the story of the biggest dick I’ve ever fucked.

(By the way, I do love hearing from readers, so if you like my stories, please shoot me a message. I especially love hearing about the effect my story had on you, the more explicit the detail the better.)

So: not the biggest cock, but the biggest dick, by which I mean the douchiest asshole whose manifest flaws I managed to look past for the sake of sex. His name was Roland, and his cock was perfectly lovely—somewhere over six inches, slim, and with a wicked curve. The only problem with that cock was the dick it was attached to. Roland was an aspiring actor and model and was quite possibly the most beautiful man I’ve ever encountered in real life. Think: young Rob Lowe, but even prettier, with dark eyes and perfect cheekbones, pillowy lips, and the kind of body one imagines was developed in a lab with the express purpose of getting men hard and women wet.

I met Roland while I was working my first job out of university. I’d been hired at a medium-sized talent agency. My double major in English and commerce was my ticket in: commerce got me the interview, English got me the job. They needed someone who could write proper sentences to compose and edit publicity briefs, talent bios, press releases, and so on. It was tedious work, but it was a paying job, and it put me in proximity of a lot of good-looking people. Not all of them were the talent: my boss Fred was a failed actor turned agent, a tall fit man of indeterminate race who wore his pants slightly too tight. Alas, he was married and very hetero. My best friend in the office was Naomi, a Jewish girl of the sort I’ve always found irresistible: curly hair, glasses, dusky skin, and amazing breasts. We flirted outrageously, and she made no bones about the fact that she found me attractive, and also that she was devoted to her boyfriend. But she loved to hear the tales of my sexual escapades, which I recounted to her often over drinks. Hearing me talk about fucking men and getting fucked was a massive turn-on for her, and more than once she drunkenly said that if ever she was single she wanted to slide between me and some other guy.

(That, sadly, never happened. She married the boyfriend, and last I heard they’ve got four children.)

We bonded over many things in the job, but there was nothing we were more sympatico on than our loathing of Roland. Roland was at that point a model, but wanted to break into acting, and Fred was determined to help him. He was supposed to be the agency’s golden ticket: Fred was convinced he’d be the Next Big Thing who would mint money for the agency as well as raising its profile. Naomi and I were sceptical: though we hated ourselves for finding him so attractive, we’d watching his audition tapes, and he was terrible. Wooden, dull, and above all dumb. Not a thought in his pretty little head.

Thing was, he was convinced of his brilliance, and he already acted like he was an A-lister. He was haughty, dismissive, and was by turns condescending and nasty to the office staff, all of whom he treated like the help. And from what we learned, he couldn’t take criticism—both getting snippy at it, but also baffled. So convinced of his overweening talent, he couldn’t grasp what was being told to him. Fred hired a succession of vocal and acting coaches, all of whom threw up their hands in frustration.

“He can’t even get laid half the time,” Naomi confided to me one evening, the vodka tonics slurring her voice. “That’s what I hear. Drunk women throw themselves at him, and go home with him, but if they sober up enough to actually listen to him speak… it must be like ice water on the crotch. So many women either book it out of there before anything happens or are all like, ‘Can we just cuddle?’”

I’d heard he liked men too, but in the few times I’d spoken with him I got nothing—no sense that he’d even registered my presence, never mind the usual subtle appraising glance I was accustomed to.

Then one night we had an office Christmas party. Fred splurged to rent out a fancy local bar, inviting all our current as well as prospective clients. It was a fun night; I got chatted up by a handful of men and women, thought it was all just flirtation that ended abruptly when people realized I wasn’t an actor, model, or someone in the agency with clout. Sad to say, being just a notch above office gofer wasn’t much of a panty-loosener or a boner-maker. Certainly not in that industry, which is one of the reasons I didn’t stick with that job for long.

I improbably ended up at a table with Naomi, a few of our co-workers, a matronly woman who had played mothers on several sitcoms… and Roland. Why he deigned to sit with us, I don’t know. Nobody at the table was overly pleased to have him there, as he was going on and on about his favourite topic—himself. It was late in the evening. Everybody was a bit drunk, tired, and starting to think of how to extricate from the table to go home. I myself was waiting for a long enough pause in Roland’s story about his latest modelling excursion to the Cayman Islands so I could stand up and take my leave. I thought I had it when he broke off to down the dregs of his drink. Before I could move, he slammed the glass down on the table and declared, “I need to get laid! Who’s coming home with me?”

Now he had our attention. He looked around the table once, and then again, finally coming to rest looking at me.

“You!” he said. “You’re cute. You like men, right?”

Dumbly, I nodded. Out of the corner of my eye, I caught Naomi staring at me in horror.

Roland stood, a trifle unsteadily. “Come, then.”

Part of my mind was screaming at me to tell him to go and fuck himself, but the truth of the matter is that I was drunk and horny and my cock had hardened to half-mast the moment he looked at me. I glanced at Naomi as I rose and shrugged apologetically. Her mouth thinned, but I also caught an amused glint in her eye. She shook her head, absolving me, but I knew I’d catch hell from her.

I also knew she’d want to know every last detail.

Roland was waiting for me at the coat check. He looked me up and down as I approached, his expression appraising. Though he didn’t say anything, his expression said, You’ll do.

Which was both humiliating and exciting.

He didn’t speak as we took a cab to his apartment, but stared out the sleet-streaked window. It didn’t even seem like he was aware of my presence. I was half expecting him to exit the cab and leave me to pay for it, but he paid—and tipped badly. The cabbie gave me a look, and again I found myself shrugging in wordless apology.

Roland’s apartment was nice, clean, and small. But it was more stylishly decorated than I could afford, and was pretty much a shrine to his own beauty—framed black and white images of some of his photo shoots decorated the walls, all of them showing him in various stages of undress. My cock, which had softened in the cab, hardened again at the thought of not just seeing that body for real, but touching it.

He paused in the middle of his apartment and turned to me. “Like what you see?” he asked.

I nodded. He smirked.

“Well then. Let’s do this, shall we?”

Without preamble, he untucked his tight-fitting button-down shirt and pulled it over his head. He then unbuckled his belt, undid his pants and slid them off, underwear and all, standing in front of me totally naked. It had taken just a few seconds, before I could say anything or get a grasp on what was he was doing. Suddenly there he was—not so much a Greek god, perhaps, as the kind of beautiful youth who made the Greek gods lose their shit. This was the kind of physical perfection that would distract Zeus from his usual obsession with nymphs.

Roland was tall, about an inch taller than me, with broad shoulders and a torso that tapered down to a slim waist. He was hairless—by nature or by design, I never would know—with perfectly sculpted and ridged pecs and abs, long elegant legs, and (I would soon see) an ass you could set your watch to. His cock was just shy of being flaccid, plump enough that it was obvious some blood was going to it. He was uncircumcised, with a trimmed thatch of black pubes and decent-sized balls.

He leaned back against the counter, arching his back slightly and thrusting out his hips in an obvious gesture to what was expected of me.

Though I hated myself for it, I immediately sank to my knees even as I tore at my clothes. He sighed as I grasped his soft cock between my fingers. I moistened my lips and kissed the tip, sliding my tongue out slightly to graze the underside. I lifted it, kissing and tonguing down, feeling it stir and swell.

Those days, it wasn’t often I started out on a flaccid cock. Most guys were hard by the time the pants were open, so this was an interesting thing for me. I took him entirely in my mouth, swirling my tongue against the loose flesh, feeling the satisfaction of it becoming engorged. All the while Roland murmured, saying, Yes, that’s good, yes, good boy.

When his cock was halfway hard I slid my mouth off and gave it a few strokes. It was a decent size, and a nice thickness. It was, in fact, the perfect size for sucking. The best thing about it was its curve: it hooked sharply up and to his left, the kind of bend that would usually make me want nothing more than to get fucked by it.

But by then, I’d already started to entertain other thoughts.

Somehow, while I sucked him, I managed to shed my sweater and shirt, and I had my pants open. My own cock was hard and leaking. I stroked it while I sucked him. Dammit, he even smelled good, and the precum I licked from the tip of his cock was delicious. I looked up, hoping to meet his eyes while I slid my tongue up his shaft, but he had his head thrown back. He was moaning by now, however, his breathing quickening. I let my hands slide up and down his perfect thighs and creep around to cup his perfect ass. I fondled his balls and ran my fingertip over his puckered hole, eliciting a gasp of pleasure from him.

I brought all my technique to bear. I was determined to give him a mind-blowing blowjob, not because I liked him or wanted to impress him, but because I decided my revenge on him was to make him beg.

My favourite part of a blowjob, aside from feeling and tasting a guy cum in my mouth, was in those moments when he came close to the edge. I had become quite good at reading the signs—the quickening breath, the cock swelling, the little whimpers, a tightness in the thighs. When I wanted to edge a man, I could make it exquisite torture. I felt Roland getting close, so I backed off a bit, taking my mouth off his cock and feathering the tip of my tongue up and down his shaft. With my fingertips, I traced the outline of his cockhead, smearing the precum around. I let my hand drop along his length, cupping his balls and snaking my slick fingertip out to tease that tender skin between his scrotum and his hole. He hissed a low yesssss, and then moaned as I pressed my fingertip against his sphincter, tracing the ring of his hole, at first gently, then more insistently, all while I kissed and licked my sloppy way up and down the base of his cock.

He started murmuring, inarticulate sounds of appreciation that became more plaintive. His cock was swollen and throbbing and desperate for release, enough that he tried to stroke himself. I slapped his hand away gently and he whimpered. Please.

Instead of responding, I grabbed him firmly by the hips and turned him around. Before he could protest, I spread his cheeks and snaked my tongue in to slide around his hole. He gasped and pressed his ass against my face. With my hand I fondled his balls and ran my thumb along the underside of his cock. Oh god oh god oh god, he bleated.

When I finally rose to my feet and pressed myself against him, he twisted his head around, his mouth seeking mine. I obliged, kissing him. He kissed me back, hard, desperate. “What are you doing?” he gasped as I wrapped my arms around his ridged chest and rested my own hard cock in the cleft of his ass.

“Tell me what I’m doing,” I hissed in his ear, and he shuddered.

“Fucking me?” He sounded somehow both confused and hopeful.

“Maybe. Do you want me to fuck you?”  I slid my cock, slippery from my saliva, up and down his valley.

“Oh. Oh. God. Yes.” He was, I could tell, surprised. But also desperate. I suspected he’d been so worshipped by his previous lovers and fucks that he hadn’t been reduced like this in ages.

My cockhead found his hole. As soon as I eased it past his sphincter, he growled and pressed back until I was hilt-deep in him. “Oh, fuuuuuck,” he moaned. “Oh yes. Fuck me.”

I obliged, grabbing him by the hips and fucking him hard, pressing him down across the counter. I leaned back slightly so I could enjoy the view of his perfect ass, impaled on my cock. His swimmer’s back was ridged with muscle, shiny with sweat as it arched in his ecstasy. I slowed my pace, letting him feel every inch of me as I slid in and out of him, pausing at the top of my stroke until he begged me to stick it back in him.

I’m not sure how long I fucked him like that. I brought myself to the edge twice before slowing down again. The third time, he put me over the edge, begging me to cum in him. With one last, deep thrust, I cried out as I came. He grasped the edge of the counter, pressing back against me, whimpering.

As much as I wanted to collapse against him, I couldn’t forget the state of his cock. I wanted to make him helpless, and I had, but my basic, primal desire for cock wouldn’t let me be overly cruel. Flipping him around again, I sank to my knees, and there it was—tumescent, leaking, throbbing with a visible pulse. I slid my mouth over it as Roland cried out yet again.

He didn’t last long. One, two, three times I swallowed him. On the upstroke of the third, his cock swelled and exploded, disgorging salty-sweet cum I swallowed greedily, lapping it off his softening cock.

He pulled me to my feet and kissed me deeply, his tongue swirling about in my mouth. Wordless, he took me by the hand and led me into his bedroom.

We barely spoke. I fucked him again twice that night, and some time before dawn he called me a cab. I went into work the next morning with some trepidation; about half the office had called in sick. Naomi was there, terribly hung over but insistent that I share every gory detail. We took and early and very liquid lunch, and I told her the whole sordid tale. She forgave me for going home with the agency’s biggest asshole on hearing what I had done to that asshole.

And Roland? He went back to being Roland. He never said a word to me about that night. Nor did he change in his behaviour to me at all—which was at once a relief and a bit irksome. Eventually, he ditched our agency for a bigger one, but he never had the success he expected. He moved out to L.A. and made a few forgettable movies.

I do, however, occasionally watch the one in which he played a surfer and spends the better part of the film in a speedo. I never make it through the entire thing, but when I jerk off during that one scene, it’s better than porn.