Jen: Route 66 Kicks-Chicago

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Şub 21, 2023 // By:analsex // No Comment

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[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. As such, the story may or may not totally conform to reality. With the exception of the historical places and persons, all other locations, characters, and events are fictitious. Any resemblance to actual persons, living or dead, is purely coincidental.]


The TV drama, Route 66 that aired its first of three season from October of 1960 through June of 1961, almost never actually took place on Route 66. The adventures of “Todd” and “Buzz” took place all over the country: from Maine to Florida, from the right coast to the left coast, and from the Canadian border to the Gulf. I decided to remedy that by telling some of the story of Route 66 and to tell it with full disclosure of Jen’s “kicks.” The complete story of Route 66 can probably never be fully told, but a check on the internet for the Mother Road or Route 66, will keep you busy for a long, long time. This is the first of a series of stories that I wrote in 2005, that will take Jen from Chicago to L.A. on “The Mother Road,” U.S. Route 66.

There is sex im the story, but not every other paragraph. If that is your interest, read some of my other stories or go to another author. The story is first and foremost about about the road, second the girl, and third the car. Enjoy. The author.


Hi! My name is Jennifer, but no one ever calls me that. I am known simply as “Jen.” The story I’m going to tell you took place more than forty years ago in the summer of 1963. I remember what happened, although some specifics have dimmed with time, but I still have my detailed diaries for that decade to which I can refer for most of those specifics. My diaries started at age five. I still keep one daily.

I had just turned twenty-three in February of that year and I bought the car in the last week of April. What a car it was, too. It’s a shame I didn’t hang on to that masterpiece of machinery instead of selling it ten years later–one of the biggest mistakes of my life! Such a rare car would be worth a lot of money today. This story is about me, a car, and a road.

So first, more about me. I was a pretty good looker in those days and not too damned bad yet, if I do say so myself. I was twenty-three years old, a flaming natural redhead with green eyes and a smattering of freckles–not too many, from my face to my boobs.

Speaking of boobs, I had an ample supply, to the tune of 38 D and all natural, too. This was near the top of my five foot, ten inch frame. Further down, my waist measured 28″ and my nicely shaped hips, 36″. My thighs and calves were shapely and toned, tapering nicely from my tight little rounded butt. Back then, I wore a size ten dress (eleven or twelve if I did not want it skin tight in places) and a size six EEE shoe.

I was into the women’s liberation movement, in both attitude and dress, even before it arrived officially with the NOW organization in 1966. That’s why I usually wore shorts, halter or tube tops (braless, naturally), either very skimpy panties or none at all, and went barefoot in sandals.

I could afford to roam around footloose and fancy free because I was an only child, living on a more than generous inheritance from my parents who had been killed in an accident two years before. It would be a number of years yet before I settled down enough to think about a job and/or marriage.

The little Illinois town I grew up in during the 1940s and 1950s had a population at that time of about 3,300 people. It was then and is even more so now, a bedroom community for those who worked in Peoria, a few miles away, especially those who worked at Caterpillar. I don’t remember a whole lot from the 1940s, but I do remember bits and pieces of that time.

Then there was the fabulous fifties! The tame fifties. Eisenhower would dominate the decade in the White House, and I started fifth grade in 1950. My grade school memories aren’t many, but they are mix of pleasant and painful.

High school occupied my time the second half of the fifties. Life in a small town high school of less than three hundred students was great, easy, and boring. Boys were boring, interested in only one thing beyond sports, scoring with girls. That is to say, getting to all the bases and scoring a home run was the goal. Only one boy made a home run with me. And that was just to satisfy my own curiosity, but my interest had been whetted for later.

That later was college, which for me, began in the fall of 1961, but only lasted two years. I was more interested in campus parties than campus study groups. I also began feeding my sexual appetite rather frequently at some of those parties and I lost interest in gaining either a B.A. or an MRS. very quickly. So, with my parents dead and me terribly bored, with that generous inheritance, that was the end of school for me.

I decided to cut loose any way I could. Beylikdüzü escort A few years later into the decade brought the women’s liberation movement and the so-called sexual revolution and I embraced them, body and soul. Independence! Empowerment! Sexual freedom and Equality! Those were heady thoughts and heady times, especially for women, believe me.


Ahhh, then second, we come to ‘the car.’ I usually referred to it (her) as ‘Swifty’ or occasionally as ‘Miss Swifty.”

“Just what was this stupid car?” you ask.

Well, the stupid car was a 1963 Corvette.

“And what.” you ask, “was so damned special about a 1963 Corvette?”

Well, I will tell you what. Miss Swifty was a 1963, all black Corvette, split window coupe with red interior. And not just any coupe, but the Z06 coupe. General Motors only made 199 of the Z06s and the entire split window coupe line, only that one year. And of those 199, only 50 of them (mine was one) were delivered with the big, N03, 36.5 gallon fuel tank.

She had the L84 FI, 327 cubic inch, 360 horse power engine with the G81 positrac rear end. Other parts of the $1,818.45 Z06 option package, added to the base price of $4,257.00 were: the M20 four speed tranny; special, heavy duty racing suspension; special big brakes unique to the Z06; and the P48, knock off wheels. It has been reported that there are only two sets of these P48 wheels in existence today.

The option list went on, but you get the idea. This car really was not meant for the casual street driver, but instead for serious track or rally racing. the $6000 plus price tag was a lot of money, a lot of serious money in 1963. Yet today, I get wet pants thinking about that car.


And finally third, there is the road–a road that exists now, only in memory for the most part. And that is a fading memory indeed for the average person old enough to even remember the road–except for the Route 66 fanatical fan club nuts, like me.

There is more than you ever wanted to know about this famous old road on the internet, in books, and in museums all along or near its once famous route. So I need only tell you a brief overview here.

Ever since the debut of the horseless carriage at the opening of the twentieth century (actually, the earliest prototypes, somewhat earlier) the demand for better roads drew increasingly loud clamors. An especially growing demand began for an automobile connecting road across the country to match the cross country route for trains.

Legislation for such public highways first appeared in 1916, with revisions in 1921. But it was not until Congress enacted a more comprehensive version of the act in 1925 that government executed its plan for national highway construction.

Officially, the numerical designation “66” was assigned to the Chicago-to-Los Angeles route in the summer of 1926, thereby acknowledging it as one of the nation’s principal east-west arteries. From 1933 to 1938, thousands of unemployed young men from virtually every state were put to work as laborers on road gangs to pave the final stretches of the original, two lane road.

As a result of this monumental effort, the Chicago-to-Los Angeles highway opened in 1932, linking the two cities with a two thousand, four hundred mile, meandering highway that came to be called the “main street of America” because it connected the little hamlets along the way, not just the big city hubs.

Once John Steinbeck’s novel, The Grapes of Wrath and the movie made from it were history, the term “Mother Road,” became the most often used nickname for Route 66. The road was finally reported as “continuously paved” in 1938. Changes in routing and upgrades have marked the history of Route 66 ever since, up to its final abandonment in favor of the new Interstate Highway System that replaced it.

Route 66 had become outdated as unlimited access highways were now out of vogue for high speed, cross country driving. The poorly maintained vestiges of the mother road finally and completely succumbed to the new, limited access Interstate System in October 1984 when the final section of the original road was replaced by Interstate 40 at Williams, Arizona.

The influence of the Mother Road on American Culture, as the road became lined with motor courts, Burma Shave signs, two pump service stations, and curio shops, is well documented in books and on the web. Just a couple of examples: from the old tourist cabins came the growth of the modern motel industry, catering to the motoring public; and from the one pump grocery store, came the growth of the modern, corporate, individually recognizable brand “filling stations” and monster truck stops.


Oh yes, I was going to tell you a story, not give you a history lesson on cars and roads. To the story then. Several things influenced my thinking that started me on the road (pun intended) trip that is the body of this story.

One of those influences was Dinah Shore, a popular singer in her heyday in the decade of the fifties. I was out to “See the Beylikdüzü escort USA in your Chevrolet,” as the Chevrolet ads from that era used to say in print and Dinah Shore said in song.

But I was really out more to flaunt my independence–especially my female independence. And just maybe I would fulfill some of my fantasies along the way. A little sight-seeing along the way would just be icing on the cake.

A second influence was the old TV show, Route 66, staring Martin Milner and George Maharis. For you younger readers, that was an old CBS program that ran for sixty minutes every Thursday night of the winter television season from October 7, 1960, until the end of the season on September 18, 1964.

Nelson Riddle was commissioned to compose a new theme song rather than pay Bobby Troup royalties for his 1946 song, “Get Your Kicks On Route 66.” The program was the story of two guys in a new, 1960 Corvette (they got a new one each tv season) finding themselves and adventure (a new one each week) while cruising down, what else, but Route 66.

Only later, much later, did I discover that the show was actually filmed in other locations–very little of it on the actual Route 66. I thought, Damn, now that’s the life for me! And why not a trip down Route 66? Thus the genesis for my 1963 adventure. And so, on to my story about that adventure.


I had been living with my parents until I graduated high school in the spring of 1958. After that, I slummed around for three years, living in my own apartment. Bored, I enrolled at Bradley University in the fall of 1961, shortly after the death of my parents.

But as I already mentioned, my interest were more in the campus parties than in the campus study groups. Although my grades were still passing, I was bored and affected by the influences revealed above, I decided to quit school, sub lease my apartment, sell the house, buy the car, and hit the road. The house sold very quickly. I took what personal stuff and whatever, and put most of it in long term storage–sports cars do not have much luggage space. My car, with the big gas tank, had almost zilch for stuff.

By the second week of April, I was on the train to Chicago. Train? Yes, train. My local, hometown Chevy dealer did not have the car of my desires in stock. Worse, he said it would take a minimum of three months to special order one and get it to the dealership. But, he did find a Chicago dealer who could have what I wanted in a week to ten days.

Great! The eastern start/end of Route 66 was in Chicago and I would have had to drive from my home town to Chicago anyway to start my trip. So, the plan was, I would take the train to Chicago, rent a room for a time, pick up the car when available, and spend some time sight-seeing while I waited.

I boarded the early morning Rock Island Rocket at the Peoria Rock Island depot on Water Street and and walked up the aisle to an empty seat. I took the inside, window seat. I found it interesting that at this late date, the Rock Island line was one of the very few that still carried a full dining car and a reserved seat parlor-lounge-drawing room car.

A few minutes after I sat down, a handsome young stud stopped in the aisle, leaned over and asked, “Is this seat taken?”

“No, no one is sitting there.”

“Do you mind if I sit there?”

“No, I don’t mind, please sit down,”

He sat.

“My name’s Robert, but I prefer to be called Bob. What’s your name?”

I replied, “My name’s Jen.”

Bob was giving me quite a visual look over as he was getting acquainted with me. It was obvious he liked what he saw. His gaze, innate to most men, seemed to be centered more at chest level than anywhere else, but I didn’t mind. I began flirting with him in return.

I was decorously dressed, one of those blue moon things, in a below the knee skirt, blouse, and sweater, but that didn’t mean I couldn’t let the skirt begin to ride up or that I couldn’t unbutton the blouse further to reveal more cleavage. There were other feminine wiles I used to flirt with any man. Bob was no exception.

Bob said, “I’m a marketing analyst consultant. I’m on my way back to the home office in Chicago. What about you?”

“Oh,” I replied, “I am starting an extended vacation. I’m going to Chicago to see some of the sights while I wait to pick up my new car.”

“Do you know yet where you will be staying?”

“I am going to get a suite at the Palmer House,” I replied, “It’s already booked and waiting.”

“That’s great. I’ve an apartment not too far away, close to my office. Maybe I will see more of you around town.”

Bob made that last comment as half question, half statement. He seemed to be fishing around rather than straightforward asking to see more of me.

“Anything’s possible, Bob. Maybe you will and maybe you won’t.”

The ride was a long one since the train speed had to be held down drastically due to the deteriorating track conditions and the fact that it made frequent, local stops. The trip to Chicago formerly took Escort Beylikdüzü two and a half hours. Now the trip took double that. Amtrak was still eight years away.

Bob and I talked and flirted the whole trip. I learned that he was twenty-six, single, and on career track aimed at upper management.

We were sitting near the rear of the nearly empty car, so we were relatively isolated from the few other passengers for much of the trip. Bob took advantage of this situation to aggressively move from flirting to hands on petting. He put a hand on my thigh and, meeting no resistance from me, moved to the inside of the thigh, albeit, over top of my skirt.

Emboldened, he moved under the skirt to my bare skin , bare because I was wearing ankle socks. Bob’s hand moved upwards fairly quickly. When he reached my bare and wet pussy, he paused in startled surprise. I may have been decorously dressed on the outside, but as usual, I was braless and pantyless on the underside. My pussy was also bald as a rock.

Oh, I know shaved pussy wasn’t the fashion of the time, but then I was never one to follow fashion conventions. I was prepped, read shaved, for minor surgery a few years back and liked my bald pussy so much, I kept it that way.

“God but you feel delicious,” Bob said, “and you’re so wet!”

He had turned to me and nibbled at my neck, jaw, and ear. His right hand was caressing my pussy folds. His middle finger was sliding up and down my slit and his other fingers were on either side, quickly turning my pussy into a raging hot inferno.

My nipples had erected as soon as Bob touched my leg and now he had my clit standing out at full erection also. My clit is not so large, but it erects a full inch or more out of its hood when I am aroused. It was doing so now. Again, I got a startled look of amazement from Bob. I quickly worked up to a moderate orgasm and drooled pussy cum all over Bob’s fingers and hand.

The conductor entered the car from the other end, so Bob quickly withdrew his hand. I got my skirt back down some and laid the newspaper I found when I first sat down, over my lap. The conductor asked for our tickets. Bob had to keep his pussy drenched right hand down and give his ticket to the conductor awkwardly, with his left hand.

The aroma of my cum was hard not to miss even so, but the conductor punched the tickets and walked on through into the next car without comment. With the conductor gone, Bob picked my hand, placed in on his crotch, and placed the newspaper over top of it.

“My turn,” he said, “give me a hand job and finish me off with your mouth.”

I got Bob unzipped and reached in through his boxers and grabbed his very stiff and throbbing cock. He moaned in pleasure as I took hold of it. His cock throbbed even harder after I got my hand in motion. That cock was about average size, probably nor more than seven inches long and just nicely thick–I could just get my hand around its uncut circumference.

Slowly, I pumped that dick up and down as I reached my other hand in and proceeded to tickle and play with his balls. A moan of pleasure escaped Bob’s lips as I increased the pumping tempo a bit.

“SHIT!” Bob suddenly muttered as another passenger entered the car from the other end. I kept pumping as the passenger kept coming towards us.

“Damn,” Bob said, “stop until he gets by.”

I did, but I kept my hand around his cock, withdrawing the other hand. Bob gave me an evil look and quickly spread the displaced newspaper back on his lap.

As he passed by, the male passenger paused a moment, and with a smirky grin, said, “Having fun are we, kids? I wouldn’t mind having some of that action myself!”

I shot right back at him, “It’s a long, boring trip, come back in half an hour and you might get your wish.”

Startled, the man gave a more lustful grin this time and walked on through to the next car.

Bob looked at me and asked, “Are you crazy?”

“No,” I replied, “just horny as hell.”

“But a Black man?”

“Why not? Isn’t variety the spice of life?”

“Jesus!” cried Bob, “What are you, a nympho?”

“Probably,” I answered. “I need sex often and a lot of it!”

Bob lifted the newspaper and I resumed pumping up and down on his cock. It had gone partially limp at the intrusion of the passenger, but I remedied that in short order. I slowly built up the tempo until I was pumping furiously, slamming my hand up and down and squeezing tightly on his balls again.

Suddenly, Bob groaned, “Jesus, Jen, I’m almost there, blow me now!”

I leaned down and engulfed his man meat with my mouth. I sucked, hard. Then I swirled my tongue around the helmet head and stuck my tongue in his pee hole. That did it–Bob erupted in a cataclysm of cock cream into my mouth and throat. I managed to swallow nearly all of his cum, leaking only a small amount onto his pants and boxers. Bob shivered as I sucked his cock completely dry.

We sat up and adjusted our clothing and then just sat in contemplative silence for some time. When we started conversation again, Bob freely admitted that he had neither time nor interest in a wife and family at this particular point in his life. He intimated without actually saying so, that if he needed a woman, he had no trouble picking one up in the city.

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