Ben is Taken by Chicago's Best Ch. 03

Once the stream dried up, he grabbed hold of my ear as if I was a naughty schoolboy and pulled me to my feet. Picking up the handcuffs on his way, he dragged me into the bathroom, shoved me to my knees and cuffed my wrists behind my back to the water pipe under the sink.

"I'll be gone for a while, and I don't want you wandering off or phoning your pal Juan while I'm away."

At first, as I knelt on the cold tiles, I worried about being left to be found the next day, naked and cuffed on the floor of my bathroom by a shocked chambermaid! But I put that out of my mind soon enough, figuring he was just messing with my head, and I could do nothing but sit and wait patiently for his return.

Which, to be honest, was OK by me. The bastard was a real prick, but I had to admit he was showing me a fucking good time. Everything he'd done so far was exactly the kind of things I'd regularly beg guys to do to me. And really, he hadn't needed to put me in cuffs; if he'd told me to wait, I'd have done so without question. There's no way I'd have run off or complained to Juan or to anyone else; I was eager for more of the same. Plus, I loved being in bondage and being cuffed kept my dick hard the entire time I was left there.

Coming back after about half an hour he released me from the pipe, stood me up and cuffed my wrists again behind my back. Following him into the bedroom, I saw a large tray on the dresser piled up with beers, cigars, sandwiches, an ice bucket, and a bottle of Scotch. I figured he must have gone back to his own room to order room service and waited for it to arrive before bringing it over.

He ignored my questioning looks while pouring himself a large shot of whisky and eating one of the sandwiches. He'd taken a few gulps of the booze before he deigned to acknowledge my existence by pointing at the bed and ordering me to climb on it. I did so immediately and lay face down while he finished off the whisky and took his clothes off. Then, without a word, he came over to the bed, rolled me over onto my back and lifted my ankles up to his shoulders.

My sloppy cunt, still greasy from Tom's lube and three loads of cum so far that night, offered no resistance and let his cock pop right back where it belonged. To my disappointment, this was just a quick fuck to re-establish his control and to remind me who was boss. As if I'd forgotten! He pumped in and out of me a few times, slapping my boner from side to side with the palm of his hand, making me squeal.

Maybe he thought I was having too much fun, since he pulled out of me and took my balls in the palm of his big hand, squeezing hard while he stared into my eyes.

"I can smell that piss breath from here. Let's get that stinky mouth washed out."

After pouring what looked like the equivalent of four or five shots of whiskey into a glass, he sat me up and held it to my lips. But instead of meekly swallowing, I shook my head and kept my mouth firmly closed, ignoring for one dumb moment every painful lesson of my night so far. I'd been OK with sucking him off and being almost choked, with drinking his piss and with being fucked, but I was drawing the line at having all that booze forced down my throat! I hated the taste of Scotch and didn't want to be the latest in a string of stupid drunken boys.

Of course, my defiance lasted for less than a minute once he closed his hand around my throat and squeezed. I opened my mouth wide and obediently swallowed it down, managing somehow to stop myself from coughing it all up again as the spirit burnt my throat going down.

Since they were clearly not necessary, he took off the cuffs and dragged me by my ear over to the armchair, forcing me to my knees in front of him as he sat back to light a cigar and start on his own second glass of Scotch. Kneeling there in such close proximity to the cock that had been both punishing and pleasuring me all night, I tried to avoid staring too obviously at it, glancing down at the floor or across at the wall instead. But every time I looked away and then back, a knowing smirk crossed his face. Eventually he tired of the game and gestured at the erection sticking up out of my crotch.

"Can't get enough, eh pussy boy? All horned up with your mind on one thing?'

Without another word, he got up and shoved his cock, just as hard as ever, down my throat. I could hardly believe it; he was like a machine who'd stayed hard for two long suck sessions and three fucks and had cum twice in less than a couple of hours. Yet his fifty-something dick was still punishingly hard, some twenty years before Viagra was a gleam in a pharmacist's eye!

Just as before, his cock went in and out of my throat, cutting off the air to my lungs, making me tear up, gag and cough, until he eventually turned around, leant over the chair, and pushed his ass into my face. Soon I was happy to hear the sound of satisfied moaning from above me as my tongue licked up and down his crack and into his sweaty hole; so, hoping he wasn't paying attention I took the opportunity to grab my own needy cock and start jerking it. However, it wasn't long before he'd caught me and had gone to get the handcuffs from off the bed.

"Don't be playing with yourself while you're serving me, you little shite. Get those hands behind your back or I'll kick your balls so hard you'll be singing soprano."

Still a little frightened of him, I did what I was told. Moments later, with my wrists cuffed behind my back again, I took up again where I left off, driving my tongue all the way up his ass. Responding eagerly to the smell and taste of a real man, I dove in, keener than ever to give him a good time.

He rocked from side to side and grunted with pleasure as my tongue went up his chute. I continued to work on him until he turned and collapsed into his chair, picked up his smouldering cigar and his Scotch.

Down on my knees in front of him, watching him drink, I realised how much the massive slug of whiskey he'd forced down my throat was affecting me. I'd ignored it while obsessing over licking his ass, but now I was seriously drunk.

Seeing me looking cross-eyed at him and shaking my head to clear the cobwebs, he grinned and swallowed the last of his own drink before waving the open Scotch bottle at me.

"Pussy boy can't keep his eyes open. What's the problem, too much sex or too much booze? I think you need more of both."

He grabbed me by my hair and jerked my head back, holding the open bottle over my mouth. Even though I didn't want to get any more drunk, it was stupid to even try to resist, and just as I'd done all evening, I bowed to the inevitable and opened my mouth. He tipped the bottle over and poured more whiskey down my throat, making me sputter and cough, just like before. The moment I stopped gasping and retching, he ordered me to get back on his dick, which had remained as hard as ever. Fortunately, though, it seemed there were limits to "Mr. Studly" after all; he started pulling out and taking short rests, almost as if he was getting close and didn't want to finish too soon. I wondered; how long would he be able to keep it up?

I got the answer to that question when he got up, walked around behind me, and pushed me forward until my head and upper chest lay on the seat of the chair, with my arse up in the air. He poked a couple of fingers in me to check that my hole still hadn't dried out, then knelt up close and guided his hard shaft into me for the fourth time that night.

This was surprisingly gentle compared to the shellacking I'd gotten previously, but just as arousing. Even though he was less vigorous than before, it was still exciting to feel him inside me, while the booze was having its effect; reducing me to a state halfway between ecstasy and stupidity; groaning with neediness and giggling in the next breath.

His slow fucking motion seemed designed to keep me on the edge of an anal orgasm: almost but not quite there. I could feel the sweat pouring off him, and the heat of his body against mine, his hips and groin plastered against my back and his hands roaming over my back and my bum.

He continued to fuck for minutes on end, while I'd became so mesmerised and drunk that I didn't even notice that he'd unlocked the cuffs and that I could move my arms until he lifted me off my feet in a bear hug. While he held me tight against him and kept punching his cock up into me, I glanced down and saw that my own dick was as hard as his felt. Between Tom and the big guy, this was the fifth time I'd been fucked that nigh and I still hadn't cum. My desperate need for orgasm had snapped me out of my drunken sex haze and I was desperately close!

I guessed he was getting near the end himself and had taken the cuffs off to let me jerk myself off. I needed to get off really bad and having this big sweaty bastard hold me in a tight bear hug only got hotter. Grabbing hold of my cock, I jerked the foreskin back and forth over its head, with my hand speeding faster and faster in a blur of motion, until I screamed with relief as volleys of pent-up cum shot out of my dick and landed on the carpet, feet in front of me.

My extended orgasm made my ass muscles clamp down hard on his dick, helping his cock to respond immediately with his third load of the night. As he unloaded, he pushed my body forward and shoved me face down onto the carpet, keeping his dick inside me while pinning me to the floor with his sheer bulk, as we both came down from our orgasmic highs. When he eventually pulled out and scrambled to his feet, I stayed flat on the floor, not moving, almost comatose from the booze and the orgasm. Looking down at me, he gave me what sounded like a compliment, his only one that night.

"Man, that felt good. I didn't think I'd be able to cum again, but that hot cunt of yours squeezed it out of me, pussy boy. That's me done for the night."

He pulled on his clothes while I lay with my eyes closed, not willing or able to make the effort to get off the floor. I was already half asleep by the time he'd got dressed. He knelt beside me and startled me awake with a slap on the bum.

"Well, punk, I guess you're all done whoring tonight?"

When I whispered "yes, sir!" he told me he was going to pay me what I deserved for my night's work and shoved his fingers up my ass one last time. I was so exhausted that I didn't open my eyes or react, hoping just to be left alone, falling into a deep, drunken sleep before he'd even left the room, taking his Scotch and cigars with him.

The sun streaming through the window was what woke me the next morning, with a body aching from sleeping awkwardly on the carpet all night, a thumping hangover and a sore asshole. I knew I had to get up and drink water for my headache, but I couldn't even summon the energy to dot so. I just lay where I was, going over the events of a crazy night.

As I lay there, aware of morning wood, I rolled over onto my back, lifted my legs in the air, pulled on my hard dick and poked two fingers into my well-used hole, that soon felt something stuck up there, presumably left there when he shoved his hand up my ass as he left. When I withdrew them, I saw a greasy soggy mess of dollar bills, and once they were separated, I saw numbered four in total. He'd been in my room for about four hours, so I figured he was telling me I was worth the princely sum of a dollar an hour!

All in all, a fitting end to the first of what turned out to be many visits to Chicago!