Have you read the first two chapters of this story? Perhaps you should just so you get the gist of the setting - or not. The following story is full of all sorts of sexual antics of many proclivities. If you are underage or at all squeamish with different variations of sexual pleasure, why are you reading this? Go read something else! If you are reading this, enjoy it and give it a score. All feedback is welcome. A special big time thanks to "LarryInSeattle" for his astute editing of this chapter.
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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 woman really seemed to hold the reins, constantly deriding and ridiculing their husbands. As they got into the car, one wife told her husband, "Got 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, relit 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."
