tagGroup SexThe Designated Driver Chronicles Ch. 01

The Designated Driver Chronicles Ch. 01


The following story is full of all sorts of sexual antics of many proclivities. If you are underage or at all squeamish, why are you reading this? Go read something else! If you are reading this, enjoy it and give it a score. All feedback welcome.


For those of who have read my previous stories, you pretty much know where I'm coming from but for those of you who haven't, let me introduce myself. My name is Ray. I am a mature man living in the resort paradise of the Hamptons. I am also bisexual having been turned out about ten years ago; not long after my divorce. I do not publicize this fact and in my public life, I am recognized as a pussy hound and a masculine, straight guy. However, given the right circumstances, I can enjoy myself with both sexes. It's all good as far as I am concerned. Over the years, I have come to prefer sex with uninhibited couples the most. ...Hands everywhere...mouths everywhere...organs everywhere - you get the picture.

I took a job this past summer to make some extra cash. The job was a unique driving service where I drove the client's car while the client(s) drank and partied wherever and whatever with they desired. From restaurants to bar-hopping, I crisscrossed the East End. The money was very good and the tips were even better but, for me, the best aspect of the job was that I could be alone for several hours quietly editing and revising the novel I have been working on for the past few years. With no distractions and in their luxury car, I did a lot of quality writing.

All of my clients were extremely wealthy. Many Wall Street 'one-percenters' rent estates for a month or for the summer season out here. Money means nothing to these people; they are dripping in it. In some cases, this summer crowd spends thousands of dollars to rent, sometimes in the six-figure range. It was my job to pick them up, drive them around and take them home safely. Some of the clients were nice, normal human beings but most were arrogant and contemptuous toward me, as if I was below them. For the most part, these people still tipped very well; perhaps they were showing off...whatever. In one particular case, the client was a real bastard but he still gave me a two-hundred dollar tip for five hours work. Not bad, right? Still, as I drove home that night, I mildly regretted that I didn't punch him out. Instead, I smiled and collected my cash. I mean if these assholes want to pay me large sums of cash for my minimal labor, I am there to catch it.

I was an excellent driver, if I do say so myself. Sometimes I was a tour guide, sometimes I was a concierge and sometimes I was a babysitter. With only a couple of exceptions, all my rides were very complimentary toward me and they told my boss as much. Soon, I was handling the special clients like celebrities, movie stars and billionaires. I worked four or five days a week but considering the money I was making and the progress I was making on my book, I could have easily worked everyday.

The cars I drove were amazing. My personal car is an old Nissan but on the job, I drove all sorts of fabulous cars. Unfortunately, some of my clients had Aston Martins or Ferraris in their multi-car garages but I never got to drive those. One client even had a Tesla Sportster but I could only look and drool over it. Another client had a Fisker in the driveway. By far, the coolest car I drove was a new Bentley Mulsanne. That car had every option possible and it handled like a dream. The back-up and side cameras were so cool that sometimes backing up seemed like a video game. In this neighborhood, there are no Hyundais, Kias or Subarus; God forbid the neighbors seem them behind the hedgerows!

Since I was always super careful with these cars, I never had the opportunity to open them up on a highway. Some of these babies were fucking fast, too. I drove plenty of SUVs,too - Cadillac Escapades, Lincoln Navigators, and others by Lexus, Infinity and Mercedes. I hated the Mercedes, whether sedan or SUV. All the Mercedes cars handled like tanks. The Caddy Escalades (especially one extended cab model) and the Lincoln Navigators drove like lumbering semis. The best SUV/Truck I drove was actually a GMC Yukon XL Denali. That sucker handled the best, was extremely comfortable and had the best navigation system in the class. Other cars I liked included the Audi A6, the Audi Q7, a Buick Verano, a Chrysler 300S and the Lexus LS Hybrid. Indeed, this was a cool job.

After about two weeks of chauffeuring mad partiers around, I was asked to drive a married woman from Southampton to a dinner party. I picked her up at her rental house on Gin Lane facing the ocean. It was some impressive mansion with a pool, a tennis court and a Mercedes GL550. Gayle was very pretty, very sweet and very well behaved on the way to her dinner party to meet some old girlfriends. I learned that her husband was a wealthy hedge fund CEO who helicoptered in and out of Manhattan. He did the usual commute; he flew out on Friday night and flew back on Sunday night. Many wealthy couples do this and I suppose it works for them. And as the summer progresses and the wives become lonelier, they have a tendency to step out. But this ride was still early in the season and while I really enjoyed this women and even fantasized a bit over her super-fineness, I maintained control.

The ride to the party went very well. I learned that Gayle had a full-time nanny watching her toddler and that on this night, she felt free for the first time in a long time. I figured her to be in her late thirties. She was in perfect shape with all her tennis lessons, jogging, horseback riding, paddle surfing, spinning class and yoga. Several times, she leaned into me as she spoke and I could admire her gorgeous 36Cs flashing me under her designer blouse. But I maintained control and kept my place.

The dinner party was at Nick and Toni's, one of the best and most expensive restaurants in East Hampton. It lasted for four hours and so I had plenty of quality time to write while I sat parked in the lot. I was so involved I never heard her or her friend as they returned to the car. I quickly put my book away into my shoulder bag and got out to open their doors. Both seemed quite tipsy.

"Ray, do you mind if we take my friend home? She lives in Water Mill."

"Not at all. It would be a pleasure."

"What were you writing, may I ask?"

"Oh, just a novel I'm working on."

"What's it about?" I gave her a thumbnail synopsis and while she seemed attentive, I could tell she was somewhat inebriated.

Reenie was about the same age, very hot and in the same boat with the husband situation. During the ride, the two women sat in the back, complained about their husbands and were catty about their dinner partners. Their lips were plenty loose from all the booze and some of the stories they told were so raw that I was pleasantly entertained in the front seat. Frequently, I would peer into the rear-view mirror to ogle these four beautiful breasts beneath their loosely buttoned blouses.

"Can you believe how fat Doris is?"

"I loved Caroline's Laboutins. Weren't they gorgeous 'fuck me pumps'?"

"Ellen looks like shit after three kids. Her tits are so saggy they probably hang down to her navel." A quiet giggle escaped my lips.

"You must be cracking up listening to us."

"I admit that I am amused."

Gayle mused, "You must drive all sorts of characters. You've probably heard some wild stuff."

"Yes, I have but as most of these people are pretty drunk when I take them home, I take it all with a grain of salt."

Reenie seemed bolder than Gayle and she asked me a question that gave me pause. "Ray, let me ask you this. What do lonely horny wives do out here all summer?"

"That's an interesting question. Usually, they hook up with the gardener, the tennis pro, the pool guy, you know, like that. I don't think you two are the type to go to the wild bars of Montauk. You're both too classy for that unless, of course, you are cougars."

Gayle seemed embarrassed by my answer but Reenie pursued the conversation. "Cougars, huh? Well, I could be. So where do classy dames like us go?"

I thought for a minute before deciding to give them an honest answer. "Hmmm. There's always 'Ladies Night', that's a possibility. We locals call Wednesday 'Ladies Night' because Wednesday night is usually pretty slow and the nightspots become very intimate. Sometimes, I will go to a good restaurant or a chi-chi bar on a Wednesday night. See, Wednesday is hump day. The woman is horny because her husband has been gone for a few days and won't be back for a few more and so she is looking for a discreet hook up. I like these women because they know exactly what they want and they want you gone before sunrise."

Both women became quiet as if they were pondering the possibilities. Finally, as I approached her house, Reenie spoke. "Will you give me your card? Perhaps I might use your services some Wednesday night." Smiling, I gave her my card and said nothing. The two women said their goodbyes before Gayle hopped into the front passenger seat. She seemed a bit subdued.

"I'm sorry if I embarrassed you, Gayle. I thought that Reenie was a bit over the top and so I hit her with the truth. I hope you are not offended."

"No, I'm not offended...just a little shocked. I will admit that the idea of it is very enticing especially since my husband is such a bore in bed. He's probably too tired from tapping his secretary during the week to give me anything of quality on the weekends. Mostly, I satisfy my needs myself."

"Woody Allen says that at least it's sex with someone you love."

She laughed at that and I felt her mood lighten. "If I wanted to go out on Wednesday night - but very discreetly, do you think you could drive me? You seem like a nice guy and I'm impressed by your honesty. Could you keep it secret?"

"My lips are sealed. What happens in the Hamptons, stays in the Hamptons."

We were now approaching her house. You could hear the waves crashing on the shore and breath the salt air as we drove down Gin Lane. There was a palpable sexual tension in the car.

"I've never cheated on my husband. Never. But since the baby was born, our sex life has disappeared. I know he's fooling around."

"Do you still love him?"

"Honestly? I don't really know anymore. It's like he's tired of me and me of him."

"Then there must be something wrong with him. From the short time I've been with you, I think that beside being beautiful, you're sweet and very good-natured. You've also got a killer body. He must be crazy or bored. Perhaps you should try to rekindle the romance."

"To tell you the truth, there was never much romance in our marriage so I doubt there's much to rekindle. For some months now, I've been thinking of divorcing him."

I pulled up to the garage. "I'm sorry to hear that, Gayle. I think that at your age, you're peaking now and it is a shame to waste all that energy."

"You're a good guy, Ray." I turned off her car, got out and opened her door. She clicked a remote and the garage door lifted and a light went on. As she got out of the car, her walk was unsteady and a bit wobbly.

"May I help you?" I took her hand and guided her to the door. She opened her pocketbook, pulled out her wallet and handed me a fifty-dollar bill.

"Thank you, Gayle, that's very kind."

"I think you're worth it, Ray. You got my mind racing. Do you need anything before you go? A drink perhaps"

"I could use a glass of water. Also, may I use your bathroom?"

"Certainly." We entered her house and she steered me to the john. I went to close the door when she stopped me. "May I watch? You've made me very very excited."

I looked at her incredulously. "You want to watch me pee?"

"You've made my mind race...I'm so curious. I really just want to see your penis. It will help me cum when I get into bed."

"Sure, whatever I can do to help. I'm working for you tonight." I unzipped and pulled out my seven-inches. Her eyes never left it.

"You have a nice looking cock."

I looked at her as I peed. "And you have a great body." I finished peeing and went to zip up when she leaned over and stopped me. She reached out and held my cock. Slowly, she stroked it and it began to stiffen. I reached over a softly fondled a tit.

"Yours is the first cock I've seen or touched in many years, that is except for my husband. You're bigger than him. I like the way it feels."

I took her hand away and pulled her into my arms. I kissed her and felt her melt into me. "Wait. I have an idea." She took my hand and led me to a servants room above the garage. She pushed me onto the bed. "You've been eyeing my boobies all night. Well here they are." She stripped off her blouse and slowly removed her white lacy bra holding each breast seductively. I got up from the bed and took her in my arms again.

"I think it is you who should be on the bed." I picked her up and gently set her down. Then I slowly and deliberately removed my clothes down to my underwear. My cock was pushing against the cotton and she could not take her eyes off it. I walked over to the bed and slowly removed her skirt. She wore a pair of lacy white bikini panties that had a large wet spot covering her crotch. Her juices were flowing and her pungent aroma filled my nostrils. I lay down next to her and we began to kiss. Her hand wanted down into my underwear and began to stroke me again. My hand found its way into her panties and I cupped her lightly haired mound. She arched her back in response to my touch. Slowly, I made my way down to suckle her beautiful breasts. Her nipple was hard between my lips as I flicked my tongue over it.

She was urgent. She needed to cum and cum hard. I felt her need and made my way down to her sopping pussy. Pushing on the top of my head, she was moaning in anticipation. I buried my nose into her muff and pushed my tongue into her hole. It seemed like only a moment later when she began to rock back and forth squeezing my head between her thighs. "Oh, yeah. Oh, yeah. There. Yes." She hiccupped and pushed her cunt into me. I felt her juices running down my chin as she erupted in an explosive orgasm. I felt her vagina open up and suck me in deeper. I pushed myself away and quickly tore off my underwear shoving my cock into her. She responded with a deep animal growl. "Oh. Oh. Soooo good, Ray." With each stroke, I pushed deeper and rotated my hips. "Don't cum in me." Obviously, she was not all that drunk.

I felt my orgasm coming on so I pulled out and began to jerk it. "No. Let me." She spun around and took me into her talented mouth. I erupted instantly filling her with my cum cocktail before releasing a deep sigh of pleasure. We both lay there spent from this quick but exciting screw. She crawled up to me and we held each other. I leaned over to kiss her but she pulled away.

"You don't want to kiss me. My mouth is full of your cum and your mouth is full of me."

"So?" I leaned in and kissed her firmly, snaking my tongue into her. "We taste pretty good, I'd say."

"No one has ever done that to me before. My husband would never do that. He won't even go down on me. And that felt so good. I haven't had that since I was in college."

"There is so much more I would like to do to you. You are sooo hot."

"But not today, Ray. You have to go and I have to look in on my baby and go to bed."

"I want to do this again, Gayle."

"And something tells me that we will but not now. Now, you have to get out of here." We both dressed quickly. I tried to kiss her again but she gave me a quick peck and sent me packing. But before we left the room, she handed me a one-hundred dollar bill.

"I can't accept that, Gayle. Consider your orgasm my tip to you."

"No, Ray. I didn't tip you enough before. You're worth every penny and more. And besides, you are a great fuck." She shoved the bill into my pocket. As I drove home, I marveled at my good luck and considered how much I loved this job.

The next day, my boss called me to say that Gayle had raved about me and would use me again. I smiled at the thought.

I worked a few more days on some small drives when I got a job to pick up a vacationing couple, June and Peter, from Los Angeles renting an oceanfront mansion on Flying Point Road. This house was a modern glass cube overlooking the Atlantic. The couple both worked in the film industry as editors and both had won Oscars for their efforts. They were both in their early fifties and both were in excellent shape. They were a handsome and stylish pair. I immediately noted June's fine braless rack. It was a very warm evening and until the Bentley's air conditioner kicked in, I noticed beads of perspiration in her cleavage. They were celebrating their twenty-fifth anniversary and I drove them out to The Crow's Nest in Montauk. After their dinner, I took them to The Surf Lodge for more drinks under the stars. At two in the morning, they were finally done and ready to go home. I found that this couple was very similar to other couples in that I picked them up sober and drove them home stinking of booze. And like other couples, their backseat conversation was enlightening and very amusing. I drove with a huge smile on my face from their lewd chat.

"I think I'm in love," said June. "That gorgeous little thing dancing with the hula hoop was amazing."

"That she was. I kind of liked the lead singer. He was hot."

My eyebrows could not go any higher. They must have been pushing against my hairline. Then they started to make out. As I glanced into the rear-view mirror, I saw Peter playing with a breast he had liberated from her blouse.

"Keep your eyes on the road, Ray." Peter jokingly admonished me.

"Yes sir, but it is difficult."

As I drove, I had to contend with moans and all sorts of pleasurable sounds. I found myself rubbing my dick through my pants. We pulled up to their house and I stepped out to open their doors. I did nothing to conceal my stiffy.

"Looks like we turned you on. You liked that, didn't you?" Peter was grinning.

"I can't say I didn't."

They walked away from me and had a little conference before returning to me. Peter handed me a one-hundred dollar tip. "June and I would like you to stay a while. Would you like to smoke a joint with us and then go for a swim?"

"Thank you but that would not be very professional of me, sir."

"Fuck that. You're off the clock. Come on, let's have some fun," June was persuasive.

"Yeah," said Peter, "Don't play hard to get! And don't call me 'sir'! 'Sir' was my father!"

A short time later, after smoking a powerful blunt and a couple of glasses of wine, I found myself in their moonlit pool, skinny-dipping with them. I swam over to the side, dried my hands and relit the joint. I watched as they played touchy-feelie with each other. They swam over to me and pressed me between them as June took the joint from me.

"Oh look, he's so stiff!" Her small hand caressed my cock under the water. Soon, his hand joined hers. "Ooh, look, he likes that."

"Do you mind that I touch it?" Peter asked. "June and I both like it all. How about you?" I reached over under the water and squeezed his short fat little cock. "I guess that answers that."

"Come on, let's get out. I want to watch." June sure could be persuasive. We got out of the pool and Peter pushed me down on a lounger. June handed the joint back to me and sat down on a lounger next to me. Peter got down between my legs and vacuumed my cock into his mouth. I sat back toking up and enjoying the scene. June watched her husband as she idly diddled her pussy. I reached over and took her hand placing it up to my nose before sucking her fingers.

Peter knew what he was doing. Each time I felt my orgasm rising, he squeezed me to hold me off. June's hand furiously rubbed her clit. Suddenly she stopped and said, "Take a break. I have to go to the bathroom."

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