It was a steamy, smoke-filled night at Hernando's, and I and the other two guys had been dancing to the music on the small stage for twenty minutes. I was already down to the ten-gallon hat, the pinto pony vest, the cowboy boots, and the low-slung belt and six-gun holsters with the even lower slung eight-inch gun swinging in between and nothing else on when I felt the hand on the ankle of one of my boots.
The dude clinging to my boot looked cooler than a cucumber despite the heat and the indoor smog and even though he was wearing a suit...a finely tailored Brooks Brothers navy blue pinstripe silk suit that was cut close to his well-cut body. He looked like money all over. His pale blue dress shirt was as finely and closely cut to the perfect curves and bulges of his body as his suit was, and the gold studs in his shirt cuffs and his Rolex watch sparkled in beams from the strobing lights overhead. He was flashing a set of ultrawhite, perfectly capped teeth at me in a full-lipped, sensuous mouth. He also was flashing a fifty-dollar bill.
Having gotten my attention by grabbing my boot as I was undulating on the stage above him, stroking myself off, not far from giving the crowd the thrill it had come to see, he yelled up to me through the loud music and the din of cat calls and stale suggestions. 'You fuck me? More of this if it's good for me.'
Fifty dollars? His tie alone was worth four times that. An insult. I was having offers twice that high thrown at me by the plumbers and electricians sitting all around him. I crouched down and shot my load across the nice lapels of his $800 Brooks Brothers suit, and then I went home that night and fucked my bass-voiced boyfriend until he warbled soprano. And I did it for free.
Three nights later I was at my other evening job, the more humbling one, as a car hop at the Honeywell Hotel. They made me wear a monkey suit there; I much prefer my cowboy outfit at Hernando's. It had been air conditioned and I was watched when I wore that one. I liked being watched; I was built to be watched. Here at Honeywells I was invisible; just part of the service in getting into and out of the hotel in a jiff. But at least here I got to jockey Porsche Boxsters...at least as far as the parking lot over in the shadows beside and behind the hotel.
I was contemplating being invisible when a honey of a silver Maserati Quattoporte drove up to the entrance and out stepped . . . the suit from Hernando's. At least he was still noticing me. He picked up on who I was right off, and I was afraid he might take a swing at me for messing up his Brooks Brothers...but he didn't. He was all flashy smiles and knowing looks. And he had been slumming the other night. Tonight he was wearing a lustrous brown Armani suit, easily worth three times what the blue pinstripe the other night had been worth, and he had on an ochre silk shirt under that, a flashy silk tie, and diamond cufflinks. All just as expensively and closely cut as the suit of the other night was. The man was dripping money. It was almost like I could walk along behind him and pick up gold coins as he shot them out of his ass like a bunny with diarrhea.
Two hours later he reappeared through the hotel entrance. Another one of the car hops reached for his ticket, but he held off from giving it to the guy and looked around until he spotted me. He walked over, flashing that big, 'see what I've got and you don't' smile at me and handed me the ticket. But he also had $200 in folded fifties in the hand holding the ticket, and he wouldn't let loose of either of those or my hand as he said in a husky whisper, 'Shall we up the ante?'
I was going off duty then anyway. And two hundred bucks meant a lot to me...obviously far more than it meant to him. When I drove the Maserati around, I didn't get out of the driver's seat; I just leaned over and flipped open the passenger seat door. This was a signal to him, a gauntlet, so to speak. If we were going to do this thing, I was going to do the driving. I liked the idea of the $200, but if he thought he was going to get off as cheaply as that, he was mistaken. Tonight was going to cost him a whole hell lot more than $200.
He got in the passenger side without hesitation, and I fisted the stick shift and he fisted my stick as I drove him into the parking lot and back to the corner where I had my Chevy van parked. I clicked open the sliding side door to the van, and the suit got in without hesitation and whistled in appreciation. I had it outfitted for love. Smoked windows; floor, sides, and ceiling covered in padded sapphire blue velour; straps anchored strategically here and there, and an easily accessible sound system with speakers embedded all around. And that stool. He'd be introduced to the stool later.
I told him to take off his shoes in my home...just like they do in the Orient. And while he docilely did that, I climbed into the van, stripped off the hated car jockey's uniform, clicked the side door shut, and turned on the sound system. I selected Lebanese music with a good strong beat and a tortured-voice singer singing in a manner that would disguise most any yowling coming from inside the van. I planned on there being some yowling.
First thing I did was tie up the dude's right wrist to a strap in the ceiling of the van, a little behind the front seat. I didn't want him going anywhere or getting the notion he was going to be in charge. He hunched there, in his Armani suit, his free hand searching between my thighs.
I stripped the Rolex from his left wrist and, after entertaining him with how well balanced it was when I hung it on my hard cock and spun it around for him, I tossed it into one of his shoes. I didn't want the reminder of money ticking away while I worked here. Then I got his fist off my cock, where he had found a mushroom cap silver stud that flashed in the overhead bulb just as brightly as his diamond cufflinks did, and strapped his left wrist up to the ceiling.
I unbelted and unzipped him, and peeled the Armani trousers and Calvin Klein briefs off his legs. And I wasn't delicate about it. I heard a rip and so did he, but neither one of us showed that we cared. I was moving with determination and he was already wide-eyed and giving little panting sounds and murmured moanings. He had seen my eight inches in full erection already. He knew what I was packing for him.
He was crouched there on his knees now, panting, in fine silk socks held up with braces under his knees and above his well-muscled calves, but still fully decked out in suit coat, shirt, and tie. I crouched between his spread knees, letting my cock snake up under the tail of his shirt and bedevil his navel while our lips were heavily engaged in a sloppy kiss. I unbuttoned the two middle buttons of his shirt, just enough so that I could spread the expensive, rustling silk and expose a puffed up nipple. Then I lowered my head and pushed his tie aside with my chin and worked his nipple through the opening of his shirt with my tongue and teeth.
He was moaning for me. Begging to be fucked.
I raised his legs, one at a time, and tied them to straps in the ceiling toward the back of the van. He was trussed up now and hanging like a deer over a campfire, face up to the ceiling. I threw a leg over his belly and put my hands on the back of the front seat on either side of his head and clicked my silver cock stud against his white teeth until he opened for me and gave me head. He gave me good head, moaning and groaning all of the time at the length and width and hardness of me. This is what he was paying for. This is what he was going to get.
When I was bored with this, I pulled my cock out of his mouth and threw my leg back over him. He watched in eye-silted lust and interest as I opened a side glove compartment and took out a handful of condom packets. I opened a packet and rolled a condom onto my cock. Then I extracted a leather-studded cock ring and wrapped that around the base of my cock. The last item I pulled out of the compartment was a small bottle of KY. All the time he was whimpering for me, begging for me to get inside him.
He did look a little concerned then, though, when I reached up and undid the cuffs on his shirt on both sides and extracted his diamond cufflinks and then tied them with string to my cock ring. I was chuckling about him getting his money's worth out of this fuck. But he didn't seem all that amused.
He probably thought I was going to take my time and open him up real well for the fuck. But he was wrong there. I soaked down my cock with the KY and squirted enough into his hole for it to be beneficial for me. But then I was rimming him with my bulbous mushroom cap and pressuring his hole and making little forced entries and pulling back a little and then worrying the tight, unready hole again. And then, when I'd gotten the cap all the way in, I just thrust in and bottomed with one lunge. And he yowled to the velour ceiling, hitting a high A even stronger and truer than the Lebanese musician was doing on the background music. And he continued to yowl, first in pain and then in consuming desire, as I picked up the beat of the music and fucked him and fucked and fucked him.
As I fucked him, I bunched up that silk ochre-colored shirt of his in my fists and literally ripped it off his body, pulling the shreds of it from underneath his tie and the brown Armani suit coat. The dude didn't seem to care; he was swinging his body against my plunging cock with the beat of the music and warbling right along with the Lebanese singer. He came in great spoutings long before I did.
Sometime during the fucking, I felt the diamond cufflinks come loose and work themselves up the dude's passage with the thrustings of my cock. The dude gave little yipping sounds at this added fiber to his ass's diet, but he made no objection. He wasn't objecting to anything now except to the possibility that I might stop stroking his ass. I almost went on a laughing jag mid fuck at the image of how he'd be shitting diamonds for the next day or so. Thinking about that being close to the meaning of being filthy rich.
When I was spent, I leaned into him and encircled his torso with my arms and felt the fast beating of his heart next to mine through the shredded ochre silk until he had calmed down and I had started to reload. He was sighing and whispering endearments to me, telling me how good I was and hoping I wasn't finished taking him.
I wasn't finished. Not by a long shot. This wasn't nearly expensive enough of a fuck for this dude yet.
I released both his legs and arms, but I immediately turned him and reattached his wrists to straps at the base of the front seat on either side. He didn't object. He was licking his lips. I was giving him exactly what he was seeking from me. I pulled over a low, velour-covered stool with a hole in the seat and forced the dude down on top of it on his lower belly. His cock and balls were poked through the hole and he found that he was encased in a sleeve around his cock and sacks around his balls, which were the business end of a cock milking machine. I strapped his hips to the stool so he couldn't extract his cock and then turned on the machine. The machine started to slowly contract the sleeve around his cock and undulate over it, teasing his cock to engorge and discharge. And the sacks around his balls also contracted and squeezed in a fascinating rhythm. He seemed to like this, and began moaning almost immediately. He'd maybe have second thoughts after he'd shot off the first time and found the machine wasn't satisfied with that.
I crouched up where he could see me and changed the spent condom for a fresh one and lathered it down with KY. And then I was behind him, making him push his knees wide, his butt waving in the air. I straddled him, my thighs on either side of his waist, above his stretched thighs, my hands on his shoulder blades. And then I reared my hips back and thrust my sheathed cock inside him and pumped hard and fast.
He was singing a loud duet again with the Lebanese singer to the heavy beat of the music.
I tore the coat off his back while I was fucking him and the stool was milking him, and I put it in front of his face and tore the lining out. He didn't care. He was going over the moon with what I and the stool were doing to him. I pulled the expensive silk necktie around his neck to his back and used it as reins as I did a bull bucking rodeo exhibit on his buttocks. I could feel the diamond cufflinks churning around inside him and he could too. I could tell that by the screams of passion he was making. The Lebanese singer was reaching a climax in his yowling and so were the dude and I. The dude shuddered and came, and then moaned as he discovered that the stool wasn't finished with him. And then I gave a cowboy whoop and came as well.
After a second and then a third ride, and continuous attention from the stool, I was finished with him. I turned off the stool and untied him and he just huddled there in thank-you whimpers. As a parting gesture, I untied his necktie, rolled the spent condom off my dick, and wiped my dick and then his asshole with the silk tie and stuffed it in his mouth. His gaze told me that he was still in love. It didn't seem like anything I was going to do was going to tell this guy where he could stuff all his money, as far as I was concerned. Still, I figured when the semen had drained out of his eyes, he'd come to his senses and survey the damage I had done to all his expensive stuff and get a little mad.
I put my car jockey duds back on and made sure he could see where I was leaving the keys to his Maserati. And then I left him there, in the back of my Chevy van, and walked back over to the entrance of the hotel. Within minutes a studly black guy gave me a ticket and a look, and, when I'd driven around his shiny black Mercedes CLS55 AMG, we were driving off to his up-town penthouse apartment, where I fucked him silly and he fed me breakfast, begged for and received my bone a second time, and then brought me back to the hotel for my now-deserted Chevy van.
Two days later, I was dancing on the stage of Hernando's when I felt a fist wrap around the ankle of my boot. There, gazing up at me with love-struck eyes was the suit, now outfitted in a black sharkskin $3,000-plus Valentino, diamond cufflinks cleaned and polished and gleaming in beams from the overhead strobe lights...holding a wad of hundred-dollar bills in his other fist. Wanting me again.