The Chauffeur
Copyright 2006 Herb Cat. Do not reproduce or distribute this story without the author's permission.
Please note: this story depicts oral and anal sex between males. If any of these offend you or are illegal to publish in your jurisdiction, or you are under the age of 18, read no further.
The characters, locations and incidents in this story are fictional. Any resemblance to actual events or locales, or persons, living or dead, is entirely coincidental.
As an author, I welcome feedback on my writing. Please send any comments about this story, positive or negative, to Herb_Cat@mailcity.com. Thank you.
The Chauffeur
I've been Mr. Herrington's chauffeur nearly a year now and I'm workin damn fuckin hard to keep the position as long as I can. I mean what's not to like about this job?!
When the agency sent me out for the interview, I wasn't expectmuch. I'd had three, maybe four, rejections already that week alone. Couldn't get a job as a fuckin dishwasher even. Noone liked the fact that I'd spent time in the joint. Herrington was willin to overlook all that, though as a man of considerable means he would have had plenty of cause to worry about some ex-con wanderin around his home. Maybe it was the fact that he had had his own scrape with the law. All those speedin tickets and DWIs were what lost him his license in the first place and sent him lookin for a chauffeur.
I remember it was fuckin hot the day I pulled my '89 Mercury into his driveway the first time. He greeted me at the door in a robe, flipflops and swimsuit. Just about to take a swim, he told me. Great day for it, I said. Come on, join me, we can talk in the pool, he said. I stammered somethin about not bringin my suit but he was insistent and I figured I better humor him if I didn't want to blow another interview.
So I followed him around back and got my first look at that fabulous pool. He took off his robe and flipflops and dove in. I got my shirt and shoes off, and took the wallet and keys out of my khaki shorts. Then I climbed down the steps. Feels real nice, I said, on such a fuckin hot day. I immediately wondered if I should have used such language with my prospective boss. Shit yes, he replied, and I smiled.
As we paddled around leisurely, he began askin what I knew about cars. And he explained why he was suddenly in need of a driver. I began to relax. Cars were my thing ever since high school. Cars and tight asses. I boasted I could retune any engine, and make it purr like a baby.
All the while we talked, I was studyin Herrington. I figured he was about ten years older than me, (fifteen I later learned). He kept himself in shape, probably worked out. And I loved how his speedo clung to his buttocks and package. I guess he was lookin at me too. After he exhausted the car talk, he remarked that my khakis looked uncomfortable in the water. Why didn't I slip them off. I stammered that I wasn't wearin any briefs that day. In truth, I didn't own any briefs. Never felt like wearin them. He chortled. Said he often didn't wear briefs, loved the feelin of trousers rubbin on his skin, on his cock. I remember even now, he actually said cock. He continued, But not in the pool. Wet pants just don't ever feel good. With that he pulled down his speedo and released his pent up mantool. Then he reached over and pulled my khakis down my legs. There, don't that feel better? Fuck, yeah, I told him.
Bare assed he took off down the length of the pool and I swam after him, like a hound dog retrievin a stick. After four quick laps, he hopped out on to the pool's edge and let his legs dangle in the water as he grabbed a couple towels from a nearby chaise. I sat beside him and he handed me a towel. I dried my face, hair and chest and draped the towel over my shoulders. He began tellin me about the job. I could live in the apartment over the garage. I was to keep his Jag, Hummer and Bentley all in top workin order. Then I was to be on call to drive him at any hour any day. When he told me what he'd pay me, I sure as fuck had no complaints. Plus, he said there'd be some extra perks. Boy, were there ever!
I tried to act cool, like I was deliberatin his offer, but in less time than it took him to finish gettin dried and stand up, I told him I'd take it. Good! He reached down and shook my hand. His thick dick was inches from my face. Unthinkingly, I opened my mouth. Then comin to my senses quickly shut it tight. Hell, young fella, nothin feels as good after a strenuous swim than a good blow job. Go on, have a taste! I opened my mouth again and engulfed his uncut head with my lips. I closed my eyes and suckled him in. I was in fuckin heaven! I had just been given a job, a real fuckin job. I had just been given a place to stay, and now I had a huge fuckin cock in my mouth. I licked his shaft up and down, I licked his balls, still tinged with chlorine. He turned, and straddled my face so I could lick his asshole. He spread his legs and pulled his cheeks apart so I could do more than lick; I suckled his asshole. He was groanin in ecstasy. Then he backed up and I took his cock i! n my mouth again. After a couple minutes, he pulled out, his cock now swollen to a full nine inches and throbbing. He let loose a series of cumshots that showered my chest. Young man, you're hired! You are fuckin hired!
From that first day, I loved workin for Herrington. The cars were a dream come true. The apartment was real comfortable. And Herrington seemed ready for a blow job at least twice a day. He had me fitted for a uniform, instructin the tailor to make sure the pants were good and tight. I drove him to his club, to his office, to the stores, and out to the country just for a spin in the Jag. I kept all three cars clean and hummin. He had me ditch the Merc. It just didn't look right parked beside the Bentley.
Herrington lived alone. His business manager came by every other day. He had a cleanin lady come in once a week. He sent his laundry out. He managed to rustle up his own breakfast, and nearly always went out for lunch and supper, usually meetin someone and doin business over the meal. When he had a party at his home, he had it catered. But most of the week there wasn't another soul around. I began walkin around the place buck naked. For one thing, I didn't see why I should get my clothes all greasy workin on the cars. For another thing, I knew Herrington loved watchin me wiggle my bare ass.
So one day about the third week, there I was with my head inside the hood of the hummer, loosenin the plugs, when I felt somethin hard pressed against my asshole. I just closed my eyes and whispered, Oh, yeah, fuck me, Boss. And he did. He plowed into my tight ass so deep that only his big balls kept him from goin further. When he pulled out, he erupted all over my back, even gettin some splooge on the Hummer's engine. Don't worry I'll get that cleaned up, Sir. Forget it, young man, now it's your fuckin turn. And he meant it literally. He stuck his head under the hood and positioned his ass to get fucked. Yes, Sir, whatever you say, Boss. After that, he made sure that we had a fuck some time at least once a day. If the day was too busy, then at night he insisted I sleep with him in his bed, so we'd get in the fuck we both needed.
Sometimes we'd be drivin late to some important business meetin and he'd have me stop on the side of the road, get in the back seat and sit on his pole, fuck the damn meeting.
After six months, Herrington remarked that I had a birthday comin up. Got somethin special planned, he winked at me. Of course, I was excited. On the day I turned 26, he had a fabulous meal sent in. All my favorites. And a big gooey cake. But I knew there was somethin else coming. After we finished dinner and the caterer had left, he suggested we get comfortable in the pool room. I knew that comfortable meant buck naked. We laid down on the pool table and 69ed a while, when I realized there was someone else in the room. I turned and beheld this magnificent stud. Not just any hunk, mind you, but Jason B, the star of a dozen skin flicks which I had jerked off to repeatedly. I had a small collection of DVDs in my apartment and those with Jason B were practically worn wafer thin from so much use. My mouth fell open. Herrington explained that he had Jason flown in from LA just for me. I turned and kissed my boss on the lips and immediately Jason attacked my cock still wet wi! th Herrington's saliva. Happy birthday, my boy.
Jason sucked me off, then I sucked him. He fucked my ass, then I fucked him. And Herrington watched it all smiling. C'mon Boss. Get over here. Herrington didn't need a second invite. As I pulled my cock out of Jason's ass, Herrington stuck his in. Then I shoved my cock in Jason's throat. I don't know which sucked harder, Jason's mouth or Jason's hungry ass. The Boss and I kissed again as Jason swallowed our cocks into both ends. The evening continued with circle sucks, double fucks, and everyone rimmin everyone. I laid down on the pool table thinkin I was fully spent, when Herrington grabbed the remainder of the birthday cake and pushed it down on my cock. Then both he and Jason went to work eatin it off my cock all three of us laughin like little boys. In the mornin I drove Jason to the airport in the Bentley and even though he had a flight to catch, I took time to pull over for a roadside fuck.
Speakin of the airport, I was often dispatched to meet some important businessman at the airport and bring him back to Herrington's home or to his office. The deals being negotiated were always at least seven figures. I'd stand outside the baggage claim area in my chauffeur's cap and jacket, boots, and of course those tight tight pants, holdin a sign for "Mr. Philips" or some such big wig. A couple of times that first year, the Boss gave me instructions before headin off to the airport to be sure that the client is well-taken care of. I understood what that meant. To secure the deal, Herrington had promised said client a tasty piece of ass. My ass. I'd take a certain route from the airport that allowed me to pull over in a discrete location. I'd get that talented ass of mine into the back seat and have it properly stuffed with a big fat cock. The next week, I'd find my pay envelope stuffed with a big fat bonus. Herrington once started to apologize to me, sayin he hated t! he idea of pimpin me like that, but I shut him up. Fuck, it's business, Boss. And what's more, it's fuckin great when you can mix business with pleasure! After that, Herrington seemed to have lots of clients who required that little extra incentive to close the deal.
About once a month, Herrington would have me take the Bentley and we'd cruise down State Street, until he found a whore boy that suited his needs for that night. The kid was always excited about gettin picked up by a Bentley, and I know he doubled or tripled his askin price. Herrington didn't care; he was always generous to his clabbers anyway. I'd drive them to whatever motel the lad did business with, and once they were safely ensconced in their room for the evening, my time was my own. I usually headed for a leather bar where my uniform and boots were always a magnet for leerin eyes and gropin hands. I could always count on findin a good tight asshole there -- or two or three -- before I needed to get back to pick up the Boss and his date. When we'd drive home after such a night, we'd both be well-satisfied. Of course, that never stopped us from havin another fuck back home.