The Designated Driver Chronicles Ch. 02


I suggest that you read the first chapter of this story just so you get the gist of the scene – 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 “Larry in Seattle” for his astute editing of this chapter.


I was making pretty good money driving rich people around the Hamptons. Some jobs were just a few hours long while I waited for my clients to have dinner and drink way too much. But that is what I was there for. As I mentioned previously, if wealthy people wanted to throw large denominations in my face, I would keep my mouth wide open and not miss a morsel. Most of these people wanted a driver who kept his mouth shut and looked straight ahead at the road.

Sometimes, I couldn’t help myself especially if moans were coming from the back seat. Quick glimpses caught several blow jobs, many unencumbered breasts and even a squishy pussy or two. My favorite antic was when the wife, dressed in her hottest and latest designer outfit would wait until I opened her door and then slyly exit with her legs spread and gives a lovely panty glad beaver shot for the driver. That seemed to be a regular thing as very few of these women seemed to have any shred of decorum.

I was also having problems with my boss. Sure, he assigned me to good jobs but I had to contend with bounced checks, boozy diatribes and wildly erratic behavior. I quickly resolved to leave his employ and set up shop on my own. I just needed a few more bucks to run some ads. I decided to work through July before I claimed August and September for myself. I also kept my mouth shut and ran as many jobs as I could.

On Tuesday, I received a call from Reenie, Gayle from Southampton’s friend (See Chapter 1). I recalled that job where I drove the women home after a dinner party at Nick and Toni’s. I recalled that both were “Summer Rental Widows” as their husbands spent the week on Wall Street before flying out to be with their wives on the weekend. I also recalled that Reenie was very interested in stepping out during the week and this recollection brought a big smile.

After some small chitchat, Reenie got down to what was really on her mind. “Listen Ray; are you free to drive me tomorrow night?”

“Yes, I am. Am I taking you and Gayle out?

“Actually no and I’d prefer if Gayle knew nothing about this.”

“Sure, not a problem. What do you have in mind?”

“Well, I was interested in seeing what “Ladies Night” was all about. I was thinking that perhaps you could take me to a few well-heeled bars. I don’t know if I’ll accept any pickups but I’d love to flirt.”

We arranged a nine o’clock pickup at her home in Water Mill. I figured that I would take her to East Hampton first and then take things from there.

“There’s one more thing, Ray. I want to keep this extremely discreet. I don’t even want your boss to know. I’d rather just pay you cash if that’s all right.”

This made me quite pleased. Considering the problems I’d been having with my boss, I was glad to be expanding my business privately – especially in cash.

Wednesday turned out to be a weather nightmare. All day long, a warm rain fell from the sky with occasional gusty winds. I doubted that Reenie would keep the reservation so I called her at five o’clock to find out. She told me that I should pick her up at the assigned time.

I drove up to her house fifteen minutes early. Her black Audi Q7 sat in the driveway in a large muddy puddle. The rain had not abated and the forecast was for the storm to intensify, to continue through the night and on into the next day. I knew that this night would be a washout for business and it would probably end up early for me. I parked behind her car and raced toward her front door. I was soaking when I rang the bell.

Reenie opened the door wearing an incredibly low cut blouse and a tight skirt showing a lot of leg. Her tanned chest and deep cleavage would definitely snare any guy regardless of their horny potentiometer.

“Reenie, if there is anyone out tonight, you’ll definitely catch them.”

“So you don’t think anyone will be out tonight? Is this still a good idea?”

“I’m sorry to say that I don’t think so. It’s really miserable out tonight. I suspect that most people will be watching TV or a movie tonight. And this weather will also destroy your makeup. Perhaps it would be better to go cruising on another night, a nicer night.”

“I’m disappointed but I have to agree. Why don’t you come in and we’ll drink some wine.”

I doffed my wet jacket and followed her into the living room. Decorated with beautiful furniture, impressive art and a tall cathedral ceiling, the room looked out onto a patio and pool which overlooked a large pond. Lightning lit the room several times and thunder shook the house.

“Aren’t your children frightened?”

“No, my Ümraniye Escort children aren’t here. My husband took the week off to visit his parents in Coral Gables. He took the kids and the nanny with him.”

“Why didn’t you go?”

“Beside the fact that I cannot tolerate my in-laws, I have a showing beginning on Friday that I must attend.”

“And what are you showing besides your great cleavage?”

She laughed. “Caught your eye, huh? It’s my art that I’m showing…at a gallery in Bridgehampton. I’m very excited. I always do well. Would you like to see some of my work?”

I followed her into her studio, a large open room with floor-to-ceiling windows attached to the garage. There were several canvases stacked against a wall and another canvas, a work-in-progress on an easel. Her art was nice but not ‘drop-dead’, if you know what I mean. They were colorful abstractions of landscapes and a bit too busy for my taste. However, I made a big deal over them and complimented her.

“I’m curious, Reenie. What do you charge for something like this?” I pointed to a canvas with shades of green, blue and purple.

“I average about $65,000 per canvas. My market has become stronger over the last three years since I started painting in this direction.” The number astounded me. I could never justify that kind of money for something I considered mundane. Not that I am an art connoisseur but as a local, I am used to the art of Pollack, De Kooning, and Ernst. Comparatively, this stuff was crap.

We talked about the creative process for a while when she pulled me back into the house. “Let me show you some paintings I did a few years ago.” She led me into a large room empty except for the canvases hanging on the while walls. These paintings were far more interesting to me as they were a bit more linear abstracts of still-lifes, portraits and nudes. As I walked around the room, I quietly considered each painting. I thought they were pretty good but at a journeyman level. One painting stopped me cold. It was a fairly representational painting of a nude sitting before a tall mirror. The subject had her legs spread.

“Somehow I thought you’d like her. That’s a self-portrait I did eight years ago. My eye was still evolving.”

“I like them all, Reenie,” I lied, “but the technique is so different that it surprised me.”

“Yes, I understand. I think I became distracted by the detail.” My eye focused on the well-defined vagina and I nodded in understanding. “Now, I think I need more wine. I think we’ll postpone my adventure for another night.”

As we strolled back to the living room, I was taken by the silence and our feet clattering along the floor. Reenie came out of the kitchen with an opened bottle of chardonnay. “I started without you, I hope you don’t mind.”

“Would you like to smoke some pot?” I held up a fat joint.

“Oooh, that would be so nice…and so naughty. I haven’t had pot in years.”

I lit it and drew deep before I passed it to her. She toked up and immediately began to cough. “Don’t smoke it so deep, Reenie, your lungs aren’t used to it. Just take little hits.” She followed my advice and soon we were quietly staring out at the pond and the heavy rain pelting and dripping down the windows. She refilled our wine glasses and sat down next to me. She placed her hand on my arm.

I sensed a new familiarity. “Is it horny in here or is it just me?”

“Gayle told me how you satisfied her after the last job. Have you got any of that for me?”

I smiled and took another hit. I casually looked her up and down. She was very pretty and her large lips looked made for a blow. She was a little bit chunky in a lovely Rubenesque manner. She was top-heavy; her breasts were large and heavy, I imagined the large nipples beneath her blouse. Her butt and legs seemed almost spindly in contrast. She looked like a fun roll in the hay.

“Like what you see?” I smiled and nodded.

She rose and dimmed the lights down to a glow. Turning to me, she told me to stand up. I stood as she walked around me, observing me from different angles. She ran her hands around me, feeling and then squeezing my butt. Her hands ran along the inside of my thighs and she pressed her hands around my package through my pants. She stood in front of me and opened my shirt, lightly scratching my chest. She tossed my shirt onto a chair and then began to systematically disrobe me. My pants fell to the floor and I kicked off my shoes before kicking the pants aside. Her hands caressed my body. When she lightly traced my cock through my boxers, she moaned.

“I’m too dressed. Stay there.” I took a sip of wine and toked up as she stood in front of me and undressed. After slowly unbuttoning her blouse and removing it, I was stunned by the sight of her 38DD breasts encased in a lacy blue bra. They were large and gorgeous and she knew it. She seemed to preen as she reached behind and unclasped the bra. Her large breasts spilled out into her hands. Her nipples were as large as I had imagined with silver dollar sized circles emphasizing her İstanbul Escort long hard nipples. “Like them? I see you do.” My cock was now straining against my cotton drawers. She slowly unzipped her skirt revealing matching blue panties. There was an obvious wet spot in the crouch. She slowly stepped out of them revealing a well-manicured pubis and delectably large, damp fleshy lips. Indeed, this woman could only be described as voluptuous. For a woman with three children, her thirty-five year old body was exceptional. Now I moaned.

Stepping out of her shoes, she walked behind me and pressed herself against my back, her nipples nearly piercing my skin. Slowly she lowered herself until her lips were kissing the small of my back. Her hands returned to my inner thighs and traveled up to my heavy, juice-laden balls. “Mmmm,” she sighed her approval. She pulled my underwear down and caressed my sack before fondling my dick. Now she turned around and grasping my ass, ran my cock along and into her cleavage. I was sporting a full woody now and as it popped up out of her cleavage, she lightly kissed the tip. I went to touch her but she pushed me away saying, “Not yet.” She pushed be back onto the couch and crawled on top of me.

“Now, you can touch me.” We kissed politely but soon we were swapping spit and sucking tongue. My cock was hard and erect as she positioned herself so that my cock ran along her lips to her ass crack. Slowly, we moved in a gentle dance. Her tits were so large and so full that I couldn’t get my hands around them.

“You have amazing breasts. May I kiss them?”

“Yes, please. They’re very full right now…my period is coming…I get so horny before I get my period…kiss them…suck on them…” I lowered my face into these beauties and licked them. I grasped them and pressed them into my face feeling her soft flesh against my skin. I took one nipple between my lips and began to suck on it as though I was a nursing babe. I could tell she loved that by her moans and the arching of her back. With my face buried in her, my hands traveled down to her taut-muscled cheeks. I squeezed her ass and pushed her into me. “I need you in me,” she whispered. She sat up and slowly lowered herself onto my love pole. “Oh, that’s good…that’s very good…your cock…” I arched up pushing myself deeper into her canal. In return, she pushed down and groaned. “Don’t cum too soon, this feels so good…Hold on…Don’t come in me…”

“I’m vasectomized.”

“Then do it…do me…cum inside me…fill my cunt…don’t cum too soon, make it last.”

“You fuck me at your pace. I’ll stay hard for you.” She smiled.

“Good. You are considerate, I like that. You be my toy, my pet cock.” She, oh so slowly slid up and down, pushing me into her until she bottomed. Dripping along each stroke, it tickled as her juice rolled down collecting around the base. She was very deliberate in her movement and, loving slow sex as much as I do, we were enjoying every moment. She leaned over and placed her hands at my sides lowering herself just enough to lightly brush the hair on my chest. Several times, I pushed up as she bottomed and she moaned, softly kissing my lips. Her auburn tresses caressed my face. “I love your cock. You know how to fuck me…nice and easy…nice (upstroke)…and easy (down as far as she could go).” She wiggled her ass causing her vagina to slightly twist around my cock. This caused me to moan again and her to smile.

We fucked like this for what felt like hours but probably was no longer than a few minutes. Soon her breathing picked up and her strokes were more forceful. When she bottomed, I could feel her walls squeezing me and pushing the helmet against her front wall, probably her G-Spot. I responded by more forceful upstrokes which caused my dick to quiver. Soon, her deliberate strokes became wild and wanton. She was lost in the sensations and rising into her orgasm. My hands moved down to her ass as I helped her flop up and down. I placed my right thumb into her juicy lips and onto her small peanut and pressed my palm into her pubic bone. I measured her panting and moaning as she rose and fell. “Oh…my pussy…” She was flooding my crotch and her body was now perspiring. “Yessss…oh…oh…ah, ah, ah.” I pressed my thumb onto her clit with more pressure and she heaved a huge sigh before exploding. This was it, she was peaking. Her entire body shook and she pounded my cock mercilessly. I could no longer hold myself back.

“Damn…yes…oh my God…ahhhhhhhhh.” Squish, squish. She sat up and arched backwards as she came. I started to shoot streams of cum straight up into her. Grunting and pushing into her, my orgasm would not stop. I must have launched one hell of a load into her. When I finally felt myself empty, my body released all its tension and I fell back onto the couch. She fell with me until her breasts smothered my face. We lay there utterly satisfied. I looked out at the window as the rain loudly pelted the glass. While we fucked, I never noticed the sound.

“Reenie, that was great.” Words Anadolu Yakası Escort finally escaped my lips. “For me, that was as good as it gets.”

She looked up at me and sweetly kissed my lips. “And I can confirm that. That was great. That was easily the best fucking I’ve ever had. I don’t know whether it was my pussy or your cock but we certainly did do it right. I’m still vibrating inside.”

“Oh!” She squealed as she felt me slip from her. I sensed that she was concerned about the resultant mess on the couch. I merely smiled at her and flipped her over onto her back. I knelt on the carpeted floor and pulled her hips toward me and into my face. “But…” I ignored her and engulfed her cunt, my tongue slithering inside. She tried to push me away yet I persevered. My tongue slid out, covered in our juices which were now spilling from her pussy down her crack. I laved her and pressed the tip of my tongue around and into her back door. She gasped. With my nose against her clit, my mouth wide open and my tongue traveling from hole to hole, she was writhing in ecstasy. I slipped down to work on her ass, pushing my tongue into her and licking the rim. My nose was dripping from the fluids seeping from her cunt so I moved back up and whipped my tongue in and around her canal. She was humping my face with her hands holding my skull and pushing me down harder. I felt her pussy squeeze as she began to cum again and I was rewarded with a huge glob of my cum saturated with her sauce. Her bucking and moaning increased until the flood was released. I waited a few minutes until she settled down before I slid back up along her body, over her hard nipples and to her lips. As I went to kiss her, she pulled back. Undeterred, I kissed her again. This time, she opened her mouth and sucked on my tongue, covered in our cum. A dollop of my cream passed into her and she liked it as we sucked face. Finally, she stopped. Pushing me off the couch and onto the floor, she lay next to me.

“I can think of the last time I came twice…no, that’s not true. Often, after sex with Donald and after he falls asleep, I finish myself off. Sometimes, I go into the computer room with my vibrator and look at porn. But you! You did me so good. I think you could still keep going.”

“Is the night over?”

“No, not as far as I’m concerned.”

“Good…because I’m not done yet.”

“Ooh,” she teased, “do you have plans for me?”

“It’s a possibility.” She giggled.

We rested a few minutes before she began to talk again. This time she was very quiet. “Donald has never kissed me after he goes down on me…and certainly not with our cum in his mouth.”

“Did you like that?”

“Yes, I did. I liked it a lot. It seemed so animal, so uninhibited. It tasted good, too. Your cum is very pleasant. You must maintain a good diet.”

“No, I don’t at all. Maybe it tastes like that because it’s sperm free. I don’t know. I can’t distinguish any difference.”

“You mean you taste your cum?”

“Sure. Usually, after I jerk off, I lick my fingers. Don’t you taste your cum?”

“No. I never thought to do that. I guess I’ve never been curious. I will now though. I like the way I taste.”

“And so do I.”

“Do I taste different from other women?”

“Reenie, each woman tastes different. Actually, let me change that to each person tastes different.”

“You mean to tell me that you’ve tasted other men, too? My God, you are something.”

“Yes, I am. I’ve been in all kinds of sexual combinations and I like them all. You’ve never been with another woman?”

“No, never. Once when I was in college, my roommate came on to me but I refused her. I will admit though that at times in my life, I have been curious.”

“You should try it. You’ll love it.”

“Perhaps I will. When Gayle told me about the two of you, it made me very horny. It made me wish I had stayed in the car. I fantasized about the three of us…but I was more of a passive receiver.”

“What I find interesting is how similar your situation is to Gayle’s situation. You’re both in unsatisfying relationships and cold marriages. You both experienced things with me that your husbands have never done and won’t do to or for you. You’re both curious about a lot of things. And with me, both of you were very responsive as opposed to what you told me about sex with your prudish husbands. It was as though because it’s a secret, you can let go.”

“Maybe…I’ll have to think about this. But right now, I’d rather think about this!” Her fingers curled around my stiffening shaft. Slowly, she lowered herself to my crotch and sucked me in. She touched me in a way that made me sense that she was discovering cock for the first time. She made giggling sounds as she sucked on my balls. When she began to rim me, she giggled again. When she took me between her lips and pushed her index finger up my butt, she moaned. She was into this and it felt divine. She sucked on the helmet and stroked me. She could feel me pulse in her mouth and she increased her speed. As my cum filled her mouth, I groaned and she giggled once more. After letting me flop out of her mouth, she laid down on top of me. Grinning, she leaned down and shared her snowball, letting my cum fill my mouth. “I love this,” she cooed. “You are such a good lover.” She snuggled into me and we slept for a little while.

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