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The Designated Driver Chronicles, Ch.3

Who would have thought this job could get weirder?
Have you read the first two chapters of this story? Perhaps you should just so you get the gist of the setting - or not. A special big time thanks to "NakedInSeattle" for his astute editing of this chapter.

It was late July and I'd become frustrated with the job - well, not the job so much but the boss. Still, lately my pick-ups were boring. They were also cheapskates. Besides being light tippers or not tipping at all, most said they had a special deal with my boss and that he would settle up with me. I knew that I was getting royally fucked and I didn't like it one bit. But I still had lots of time to revise and edit my manuscript and with each tweak, the story was improving.

The clients now were mostly Wall Street types and nearly all of their discussions were about money and how they were reaping it in. Since my sympathies ran with the Occupy crowd, their cavalier attitudes revolted me. One Sunday, as I drove one of these guys to a party, I listened while he fired a worker via overseas long distance. These were not nice people.

Working for this company was becoming exceedingly difficult. Simply put, the boss was either a terrible businessman, a wise guy or a liar. It was hard to tell. I was now dealing with bounced checks, short payments, withholding tips placed on credit cards as well as sending me to wrong addresses and calling me profanities when I called to verify the correct address. I'd now developed a client following and realized that the time had come for me to go out on my own. I called or emailed my previous clients to inform them of my availability. I also asked these people to pass my service on to their friends.

I received a call one day asking if I would drive three couples to a party on Shelter Island on Friday night. The client said it would be a late night and I would be well paid in cash. When I arrived at the house in East Hampton, I was greeted by several small children playing in the front yard with their nannies. The house was a modest affair with a spectacular view of Three Mile Harbor and the ambiance was very serene. I announced myself to one nanny who upon returning from the house explained that they would be a little delayed and that I should relax for a while.

I strolled around the property before inspecting the evening chariot, a three row Navigator, not my favorite ride but what the hell. After nearly an hour, the three couples came out, kissed their children and piled into the car. None of these people were particularly good looking. The men all seemed to be subdued and the women were clearly in charge. One woman, heavy set with gargantuan tits, actually barked when she spoke. Each man held a travel bag which I duly loaded into the back behind the rear seat. The women seemed very intimidating and bossy, but it didn't matter to me, it was just a job.

I drove them up to Sag Harbor first where they dined at B. Smith's. I strolled around the village and then along the wharf to ogle the immense yachts. It was a beautiful evening and Sag was hopping. An hour and a half later, they emerged from the restaurant. They'd been drinking and now the women really seemed to hold the reins, constantly deriding and ridiculing their husbands. As they got into the car, one wife told her husband, "Get in the last seat, you weak little man." My eyebrows raised.

Driving up North Haven to the Shelter Island South Ferry, I was told to drive to an address on Coecles Harbor. I was told that while they were at the party, I should stay in the car. I thought that to be an odd request especially since I sometimes like to stretch my legs and other times enjoy an outdoor piss. I simply nodded in understanding and minded my business.

The party was in full swing when we arrived. There were about twenty cars parked around the front of the house which was laid out with the rear facing a huge lawn that spread down to the harbor. With no moon and clouds overhead, it was very dark and a little spooky. As they exited the car, the women berated their husbands for looking rumpled. The husbands meekly fixed themselves. I noticed that as they walked toward the front door, the women led and the men followed behind.

I stayed in the car for a few hours doing some quality writing. Twice I got out, once to pee and once to smoke some pot. During my smoke, I heard strange noises coming from the house. Instead of party sounds like music and laughter, it was very quiet with the occasional sound of snapping, or slapping or something like that. My curiosity was piqued. What was going on here? I wondered.

Being high and adventurous, I crept to the side of the house where the sounds emanated. I peered into the large windows from behind a large landscaped border of hedges. What I saw made me smile. Hanging from a series of ropes and supported by leather restraints was a very thin man. He was naked with his back to me. A tall woman dressed in dominatrix regalia stood behind him spanking him with a riding crop. The man's ass was bright red from the beating and it sounded like he was moaning. In front of the man was another man on his knees obviously sucking the suspended man's cock. Behind him was another dominatrix holding him by his hair. I recognized her as my client, the barker.

I thought she looked revolting, not at all sexy. Her leather outfit did nothing to compliment her body. Her immense tits flopped over the bodice. There were leather straps that held the outfit around her massive ass. The straps came around the front and held her shaved pussy tight, making the lips extended and puffy. The thought came to me that this was a good thing because otherwise it would be the old "roll her in flour to find the wet spot" joke. Behind these people were other partiers all watching the action in earnest. Some of the husbands sat at the women's feet, some wore choke collars. I watched the action until the suspended man came, shooting his jizz all over the face of the sucker whose head was pulled back to make a perfect target. There was polite applause when the scene ended. I'd had enough. Watching the scene did nothing for me except wanting to pee again.

I snuck back to the car and standing beside it, re-lit the joint. Another driver strolled up to me and we smoked up. When my joint was beat, he pulled one out and we worked on that one.

"Pretty strange scene in there, right?" Apparently, he too knew what was going on inside.

"That it is," I said. "I'm glad they're having fun but this kind of shit does nothing for me."

"Me neither. You been here before?"

"No, this is my first job for these people. They told me to stay in the car but it sounded so weird in there, I had to see what was happening."

"I've taken my ride up here a few times. It's like their private S & M club. A few weeks ago, they held it outside around the pool. That shit was something to see, I ain't kidding. The good thing is that these people pay very well. I think they pay for your discretion."

Once we were nicely toasted, we parted ways and got back into the cars. I must have fallen asleep for a few hours before I was awakened by loud knocking on the window. I rolled down the window where one of the husbands asked if I was ready to take them home. I nodded yes and asked him if he would refill my travel cup with coffee. "Milk, two sugars," I ordered. He meekly agreed.

A few minutes later, the three couples emerged from the house. I took the bags and helped them into their cars. Driving back to catch the last ferry, the atmosphere was very subdued. Upon returning to their home, one of the husbands paid me 350 for the ride and a 100 tip. He asked me if I would be willing to drive them again.

"Certainly. Call me when you need me."

"Also, my wife would like to know if you might be willing to come for dinner one night. She took a bit of a fancy to you."

"We'll see about that. I would prefer to keep this on a professional basis. I usually do not socialize with my clients. I hope you understand but I do appreciate the offer."

I drove home that night happy to have cash to deposit into my account. My mind kept repeating, "Whatever floats your boat."

My boss called me the next day with a job. I told him that until he paid me what he owed me, I was hesitant to work for him as his debt to me was mounting.

"These people requested you specifically. Are you going to take this job or do I have to drop you? Look, this guy is a good and a big tipper."

"I'll tell you what, meet me tomorrow and pay me. Then I'll be more than glad to take the job." He reluctantly agreed and so I had him meet me at my bank where he paid me 700 in cash which I promptly deposited.

The job was a pick-up in Southampton. The client was another Wall Street tycoon who had heard about me from one of his friends I had driven a few weeks before. The job was only three hours long and the client was boorish, incessantly ordering me to 'make a left here, turn right here' as if he didn't trust that I knew where I was going. At the end of the job, he paid me 150 dollars and no tip. On my way home, I decided that I would no longer work for my boss and it was high time I struck own on my own.

My boss called me the next day wanting to know how much I was paid and how big the tip was. When I told him, he began to berate me. "You must have fucked up, you asshole. I heard this guy was big money."

"I've really had enough of you calling me names and talking to me the way you do. I've come to the conclusion that you are just full of shit. As long as we're even, I won't be working for you any longer."

"Look you, you owe me my cut of last night's job..."

"Sue me, scumbag." I hung up happy to be done with him. He tried calling me a few times after that but I never answered his calls. His voicemails were filled with threats and expletives which I chose to ignore.

Except for running some ads in the local papers, the week was quiet. On Thursday I received a call from a man in Wainscott who told me that I came highly recommended by Gayle (see Chapter 1). He needed me to take him into Manhattan on Friday afternoon. First, we would stop at his apartment, then I would take him to the airport and then drive his car home. I agreed to pick him up at noon.

A few minutes later, I received another call for a job on Friday night. In the next hour, I fielded several calls which filled my weekend. I had to turn down two jobs due to schedule conflicts. I was very glad to be on my own. The Friday afternoon job paid me 500 cash. The Friday night job added another 600. One day, 1100... not bad.

The Saturday night gig was the best of the weekend. I ended up pocketing a lot of cash for the weekend although the Sunday job insisted on using his iPad to pay me through PayPal. Financially, I had covered myself for a few months and there was still another month left to the season. I was looking forward to Labor Day.

But I digress. During the earlier part of Saturday, I bumped into a friend and splurged on a fifty dollar bag of pot. Very good pot. By the time I picked up my evening job, I was straight; probably the result of two cups of coffee.

The house was a killer modern affair with a second story view of the ocean. It was not unlike many of the houses along the eastern edge of Amagansett with great views, lots of decking, lots of glass and an infinity-edged pool. This particular home faced a long stretch of dunes. I pulled into the parking area under the deck. The car I was to drive, a new Range Rover, sat in the driveway. As I walked to the front door, a stylishly dress man bounded out of the house.

"You must be Richard. I'm Wayne. We have to make a stop to pick up my friend who lives in East Hampton. And from there, we're going to a party in Sag Harbor. I'm running a little late today so let's be off, shall we?"

"Sure." The client was obviously gay with his wildly affected gestures and his dramatic way of speaking. "Wherever you want to go"

"Ooh, how inviting."

We got into the car and drove to East Hampton. On the way, I learned a little about him.

"Do you live out here, Wayne, or..."

"Or am I a summer interloper? A citiot? Not likely. No, I've had this place for about ten years. I love it out here. I'm often in the city or bouncing to Europe but this is my real home."

"Do you mind my asking but what do you do?"

"I'm an accessories designer."

"I'm sorry, but what is it you design?"

"I can see that you don't know fashion, my friend."

"Oh, not in the least. I have rather pedestrian tastes. I'm a jeans guy... Gap, like that."

"Well then. I design handbags. I also have a line of exercise wear and another line of jewelry. I'm very good at what I do, dear man."

As we pulled into a house up in the Northwest Woods, Wayne was on the phone telling his friend to be ready and the friend was already walking out the door.

"Mason! You're looking raffish tonight!" They cheek kissed.

"Ray, we're going to a private party in Sag Harbor. A "Tea Party" on a yacht docked along the Long Wharf."

I was driving toward Route 114. Mason and Wayne were catching up on gossip. I was watching the dark roads carefully as the deer were out and about. I didn't hear Wayne speak to me.

"Sorry Wayne, I was concentrating on all the deer in the woods and alongside the road. Look, there's four right over there."

"Alright, I accept your apology. Do you know where this party is?"

"Certainly, Wayne. I'll take you right up to gangplank. May I ask you something? What exactly is a "Tea Party"? Is this a Revolution era reenactment?"

They both laughed at my naivety. "No, silly man! Do you know what a "Tea Dance" is?"

"Not really, Wayne. Is that like a late afternoon party. Something from an earlier era, like Victorian or something?"

"In our circles, a "Tea Dance" is often held in the Spring or Summer, usually in the late afternoon or evening but they have them at all hours now. It's a good place a score and meet new playthings. This particular party is being thrown by C--- K--- and it will be filled with beautiful people...the Gay A-List...which fortunately, my darlings, I am on."

"I'd love to see the yacht. It must be about one hundred and eighty feet long"

"We'll see, Raymond. If you're a good fellow perhaps I'll take you for a tour."

"Thanks, I'd love that."

The yacht was everything I'd imagined and more. As they exited the car, Wayne suggested that I take the tour now because, "...things could get steamy later." He suggested that we say that I have to use the bathroom. But I didn't have to say anything. Wayne said it all.

"Oh, aren't you looking good tonight... positively yummy!" he said to the greeter checking the names at the foot of the stairs. "This is my driver, he has to make a pee-pee... can you show us to the little boys room?"

I wanted to puke. The greeter pointed to the first doorway and I quickly made my way in, Wayne and Mason close behind. For the next half hour, we toured the incredible yacht. Several rooms were filled with dancing men. Several times, I plucked hors d'ouevres from trays. Wayne and Mason were already into their third drink by the time I made it off the boat. I did stop into the bathroom before I disembarked and that room was a whole 'nother scene entirely.

I walked back to car and eased myself in. I filled my little pipe, turned on the Yankee game, pulled out my Times crossword and spent the next few hours totally relaxed and preoccupied. I was glad to step away from writing for the night.

At about 1am, Mason and Wayne entered the car. They were both very drunk and apparently had just had a fight. The vibe in the car was deadly.

"Take Mason home, Raymond. His party is over."

I made it quickly back to Mason's house. He quickly exited and slammed the door on his way out. Wayne sat with his arms folded. He was simmering.

"Back to your place, Wayne or wherever?"

"My place," he snapped.

We drove in silence for some time until we reached the outskirts of Amagansett. Suddenly Wayne seemed to perk up a bit. "I'm sorry if I was cranky, Raymond (again with the "Raymond" crap), but I feel better now. That Mason is such a douchebag and a party-pooper."

"It's okay, Wayne. I get it."

"If you only could... You must be so stiff and sore from sitting in the car all night." He leaned in from the back seat, put his hands on my shoulders and began to massage me. "Does that feel good?"

"Yeah, Wayne, it feels great. Thank you. Let me ask you something, are you coming on to me?"

"Maybe. I know you don't play for my team but maybe, you know, you're just a little curious, a macho guy like you...

"What gives you that impression? Why do you presume my sexuality?"

He pulled his hands back. "Oh, come on. Give me a break! Don't tell me you suck cock!"

"Oh, I have. Not on a regular basis. I'm bisexual. I like women but I also like to do couples. That's my thing. And while I don't want you to feel insulted, you're not my type." I could tell that Wayne was stunned. He turned quiet as I pulled into the driveway.

"...and here we are."

"Could I interest you in coming in for some coffee... or maybe some smoke? I smelled it on you when I got into the car."

"Sure. I could use the john again, too." I figured that I already made my position clear to him and so a piss and a few tokes would be nice. He led me into the house and I spent a few minutes marveling at the art collection on his walls while he brewed some coffee. He walked into the living room with a lit bong. After a couple of powerful tokes, he took my hand and led me to the bathroom.

"I have to pee, too. I'll wait. Go ahead." I went to unzip but he was still standing in the doorway, toking. "Is it okay if I watch? I want to see your equipment." I smiled, unzipped and held my meat toward the bowl. "Ohh, Raymond, what a lovely dick you have. It's very pretty. Let me see it."

I pulled out my ball sac and continued to piss. When I finished, I shook it a few times. I could tell he was impressed. I walked out and he took my place. I didn't wait to watch but instead returned to the kitchen to make my coffee.

I was sipping the brew when Wayne returned. He looked at me seriously. "I like the way your cock looks... it's a man's cock. Will you let me suck you off? You don't have to do anything to me... I just think it would be nice to have a load of cum before bed. And, I'll make it worth your while."

Maybe it was the fancy pot I smoked but I let down my guard. "Yeah, you could suck me off, I could dig that... but that's all."

"Good. Very good. Take your coffee and come with me."

He grabbed the bong and took me to his bedroom on the second level. With a floor-to-ceiling view of the ocean in front of a massive king-size bed, it was impressive. We stood and looked out the windows while the bong passed back and forth. He refilled it and handed it to me. As I toked, I felt his hands run along my fly. He moaned and made little cooing sounds. I went to pass him the bong but he said, "No, you smoke it. I'm busy."

Slowly, he unzipped me and put his hand in to feel my commando cock. He took his time unbuckling my belt and pulling my jeans down. My cock sprang out hard and eager as it bounced off his cheek. He spent some time licking my balls and the underside vein of Mr. Happy. He spread my legs apart and licked my asshole for a while. "Mmmm, I love this. Does it feel good?"

"Yeah, Wayne, it feels very good. You're hitting all the right spots."

His tongue worked up my shaft until it engulfed the crown. He was very, very good. Several times, I felt his face against my stomach as he swallowed it down. I moaned, "Oh... so good."

"Yes, I'm the best," he said between gulps and slurps. "I love your cock... it tastes so good... give me your load, baby, give mommy your load... I love your cock..."

"You're gonna get my load in another minute, Wayne, just keep that up."

He began to stroke and suck at the same time. I could feel the throbbing. He was sucking and slurping harder, faster and wetter. His finger was wiggling around my sphincter.

"Oh, man, I'm gonna cum in your wet pussy face, Wayne..." My muscles spasmed and I felt my cum take the high-speed line from my balls to my piss hole where it burst into four or five express blasts into his mouth. I coated his throat and he moaned in appreciation. He held it in his mouth for several minutes until he cleaned the now limp organ before it slipped from his mouth. I fell onto his bed. "That was a great blowjob, Wayne. Thank you."

"No, Raymond, thank you. I really needed that." He sat next to me and massaged my inner thigh. He did this for a while until he got up and began to strip. My mind began to churn thoughts about having to reciprocate. Sure, I loved the blow job but as I said earlier, I'm not into prissy stereotypes, especially not Wayne. Fortunately, for me, the choice was made. Wayne naked was not a pretty site. His belly hung over the smallest penis I have ever seen.

"Don't worry. darling, you don't have to do anything. I was thinking about how much I enjoyed that thing in my mouth and that I'd like to suck you again."

"Thanks but I don't think I'm up to it."

"Let me determine that. I suck cock better than any other mere mortal on the planet. Let me prove it."

He began to lap my cock again and for quite some time, nothing happened. My cock lay against my thigh like a dead fish. I certainly couldn't blame Wayne for not giving it his best effort, that he did. It was when he began to run his finger along my taint and press it upward below the prostate area that my cock jumped a bit. He stuck a second finger into my ass and pressed down. My cock jumped again and began to rise to the occasion. He placed his mouth over and down the column a few times. Then he began to hum and between the vibrations and the prostate massage, I was stiff and hard. My eyes were closed. All was good in the world.

"Oh, your cock is so delish, I could do this for hours... but I have another idea..." He started to suck the meatus until it was swollen and red. I heard a cellophane package open before he slid a rubber over me. He squeezed and jerked me. I felt him move around the bed. When I looked up to see what he was up to, he was squatting over my dick and then, squish, I was up his ass to the hilt.

"I want to make love to you like time and space is ending."

"Shut up, Wayne, and just fuck my cock."

He was bouncing his ass up and down as I pushed up against his cheeks. Each combination of the down and up strokes caused him to grunt, then groan in pleasure. He began to sphincter-squeeze the root with each down stroke which resulted in the same sounds emanating from me.

"It feels good. Fuck me harder."

I pulled him off me and made him get on all fours. I got behind him. "You like the cock, don't you."

"Oh, yeah..."

"Say it louder. Let me hear you say what you want, Wayne."

"I want your big cock up my ass. Fuck me hard...Please, please!"

I just couldn't handle the begging so I stabbed his pucker and pushed myself all the in. He loved that. He squeezed me in his expert way as I pummeled his ass. And, it was good, I tell you. His ass had been down this road a few times before me and his asshole really knew its way around a cock. Soon, we were banging hard and furious, I knew I couldn't keep it up much longer.

"Wait. Change!"

Wayne pulled off me and rolled onto his back with his legs upright and being held at the ankles. His asshole was a rocking target. His tiny dick was hard and, you know what? It was still tiny. I leaned over him and pushed in again. Within a moment or two, we were back fucking like animals. His whole ass seemed to get tighter and his upstrokes went deeper than they had before. Suddenly, he began to whimper, a little whiny kind of noise with an occasional hiccup. How strange. Stranger still was his cute little button of a dick erupting long streams of cum all over his stomach and chest. He rolled higher in order to try to catch some in his mouth. He missed his mouth and sprayed his nose and cheek instead. Cum was also dripping off his chest. I was impressed by his amazing trick.

He rolled down and my cock literally popped out of his ass with all attendant sounds. He spun around, pulled the condom off and swallowed me with his patented slide-and-suck technique. That was it for me. My first shot landed somewhere near his larynx. He grabbed me by the balls and pulled me out so my next shots bathed his face. I felt like Robert Johnson as he squeezed my lemons 'til the juice ran down my leg. I collapsed onto the bed and couldn't move. I was wiped. Wow, what a fuck.

We must have nodded for an hour or two. I awoke having to piss. (Hey, it happens to guys my age!) Wayne was out cold, a snoring mess. I quietly went to the john to pee and shower. I quietly dressed. I also refilled his bong and tiptoed down to the kitchen. I pulled a Mango Snapple from the fridge as well as a plate of cheese cubes, sliced sausage and roasted peppers. I toked up a couple of times when I heard the shower running. In a few minutes, Wayne joined me.

"Good. I'm glad you finally found something to nosh on. Me? I think I'll have some absinthe."

"You enjoy, Wayne. I'm done here but before I leave we have to settle the bill."

"Yes, of course, my macho man. Let's see... how many hours?... Plus a tip... and then your tip in my ass... here, Raymond, sweet Raymond... You were worth every penny." He handed a wad of folded bills. As is expected, I discreetly put it into my pocket without counting it and then I thanked him for a lovely night.

"You are also a great fuck and easily the best cocksucker in the galaxy. You have a special gift, Wayne. Thank you for letting me experience it."

"I told you I could prove it. Now run home, silly boy, or I might have to have you again... and again." He cackled as I made my way out.

I got into my car and took a deep breath. I opened the windows as I pulled away. I lit a cigarette and sipped the last of the Snapple. My dick was stone dead. Hell, I couldn't even feel my groin. I turned on the radio. I idly pulled out the wad and turned on the overhead light - all one hundred dollar bills - ten of them. One fucking thousand dollars. Holy fucking shit.

All kinds of random phrases ran through my brain. "Sometimes you have to grin and bear it"..."It's a dirty job but somebody has to do it"... "Slide, Willy, slide!" and like that. I laughed all the way home, up the stairs to my room and onto my bed until I laughed myself to sleep.

There's still another month left to the tourist season, Chapter 4 will be along soon to take you for another ride, this time with Gayle and Reenie again.

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This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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