Jen: Route 66 Kicks-Chicago

I think he said something like, "There are lots and lots of young, good looking country girls coming into the city every day, looking for jobs, adventure, romance. I sometimes give some of them what they're looking for. After all, skirts are a dime-a-dozen in the big city!"

Yeah, I thought, love 'em and leave 'em, you callous bastard. I wonder how long is the trail of broken hearts you've left behind?

Up to this point, I'd thought Bob a pretty decent guy. I was changing my mind rather quickly. Although my sexual behavior was not much better than his, at least I was up front about it and not callous about it as was Bob. A plan began forming in my mind and a smile grew on my lips. Bob misinterpreted that smile and paternally placed his hand on my thigh again and let it rest there.

Ten minutes later, the male passenger who had so rudely interrupted us earlier, returned--with two buddies in tow.

"My name is Ron and these two are my buddies, Jim and Ted. I told them what was going on back here and that I had an invitation to the party. They said they would like in on the action too, if that's all right."

Bob stared at me in shock.

I replied, "Ok, but a blow job is the best I can do for you this time."

"Suites us," said Ron, "right guys?"

"Oh Yeah!" Jim and Ted answered in unison.

Bob was still staring at me in complete shock. He hadn't said a word. He just sat there, eyes bugging out.

"All right then," I said, "Bob, you take the window seat and I'll kneel on the floor between the seats on the aisle. Jim, you and Ted sit in the seats across the aisle and wait your turn. Ron, you're first. Dig your cock out and step up!

The possibility of someone walking in the door behind us and getting caught only heightens the thrill. Ron unreeled his black cock like a hose. That damned thing just kept coming out and rising taller as it was exposed. Ron's dick was long, really long, longer than anything I had ever seen and I have seen an awfully lot of cock. And it was very thick.

I think now, that if there had been the internet back then, Ron would have made a lot of money on a giant dick site. That cock was a real monster--and a half. Well anyway, I had a hell of a time with it, fun hell of a time, that is. I stroked and sucked, bit and chewed, licked and slurped and even deep throated a large portion of the damned thing. Jesus, what a cock.

Ron finally convulsed into a mind boggling orgasm, spewing shot after shot, though not a lot of total volume, of cum into my mouth and throat. Hot and ropy, just the way I liked it. My second load in an hour and two waiting to go. God but I loved cock!

Ted, also black, stepped up for his turn while Ron put himself back together again and sat down to watch. Ted's cock dropped down to a barely average five or six inches and was already oozing pre cum. He was so horny from watching that he didn't last long before he blew his load.

If he was at all embarrassed by his size after seeing Ron in action, Jim, who was white, must have been miserable. Jim's cock was barely four inches long at full reach, but it was nearly as thick as Ron's. Embarrassed or not, he also was horny from watching and blew equally quickly as Ted.

The guys put themselves back together, grinned hugely and said, "That was really great, thanks!" They retreated back through the car and out the other end to the next car forward.

"Jesus H, Christ on a crutch," was all Bob could mutter.

******

After more than an hour of silent, further travel, as we were finally pulling into the station, Bob came out of his pout and said to me, "Jen, why don't you share a cab with me? It is not out of the way to drop you at the Palmer House on the way to my office."

"Ok by me,"

As the cab neared the Palmer House, I laid my hand on Bob's thigh, rubbing it lightly, and said, "Would you have time and would you like to be my sightseeing guide for a couple of days?"

Bob nearly jumped out of his seat. I don't think he expected me to be still interested in him and he was eager to accept. He was speechless, but nodding his head yes.

"Then why don't you call for me about noon tomorrow, in time to take me out to lunch. Then I would like to start out with a tour of Grant Park and downtown."

Bob finally found his voice again as he replied, "That sounds terrific, Jen. I have quite a lot of accumulated vacation time. I can easily take several days of it immediately. I don't know your last name or room number though, Jen."

The cab had pulled to a stop at the curb of the Palmer House as I said, "I will be in the lobby, waiting for you. Meet me there."

Before he could answer, I gave his cock a squeeze through his pants and exited the cab. My skirt hiked well up as I struggled out of the cab. The doorman got a real eyeful of my bald pussy as I did. Brittany Spears didn't invent that one, ha! He ushered me inside without a backward glance from me.

The next day went well. I slept late. In the shower, I got to thinking about the day before and found my pussy tingling. Both hands grabbed a boob and started playing. My nipples immediately popped erect. My pussy let me know it needed some TLC as well. I lowered my right hand to quell some of its stirrings.

My palm cupped my pussy mound and I boar down really hard. Fingers spread to encompass both lips while my middle finger slid up and down my pussy track. That brought some real groans from my throat, deep growls, really. The finger sank deeper into my folds.

Oh God, but that felt good! The finger went deeper, then disappeared completely into my vagina. My pelvis humped my finger like mad. Pussy cream was coating my finger. My mind was whirling with thoughts of the blow jobs from yesterday. Then, my thumb found my clit.

BOOM! ORGASM! Oh, SHIT, did I cum.

I finally came down off my high long enough to finish my shower. I stepped out of the cubicle and dried off in front of the floor to ceiling mirror. I took my time and admired each part of my body as I dried it. The body would do.

I then made up my face and dressed with time left to spare before I had to go downstairs. So I called the Chevy car dealer to tell them I was in town and how to contact me. THe car wasn't there yet, of course. Then I went downstairs for my appointment.

Bob and I had lunch in the Palmer House. The afternoon was spent walking around in Grant Park, holding hands, kissing, and some groping, all part of the menu. A late afternoon or early evening cab ride around down town to see the sights, including Al Capone's old headquarters building, the New Michigan Hotel and a late dinner at The Berghoff on Adams for German cuisine, were bringing the day to near closing. Bob had trouble at dinner, keeping his hands and feet to himself, but I didn't totally discourage him. I wanted to keep him on the hook for a bit yet.

In the cab on the way back to the Palmer House, Bob got a little more playful. I was able to restrain him, for the most part. All Bob got was a boob and nipple grope and a quick pussy grope under my skirt.

Just as the cab pulled up to the hotel, I said, "Bob, surprise me with a morning activity and then I want to spend the rest of the day at the Art Institute. Pick me up at nine."

With that, I quickly exited the cab, giving the doorman another great shot. before he once again ushered me inside. He gave me a really big smile.

Promptly at nine on day two, Bob picked me up in the lobby and said, "I took up your challenge of last night and I have booked us a Wendella boat tour of the Chicago River to see the architectural sights of the city from a different perspective."

I thought that was a capital idea and said so. That left us more than the afternoon for the Art Institute. But first, Bob took me to lunch at a nearby, upscale restaurant. We left the Institute just ahead of closing time and took a cab to Vivere's for an early Italian dinner.

The next cab ride took us to a Jazz club which occupied our time until well after midnight. Bob groped around on me some, but the place was too crowded and the music too good for him to get away with much and besides, I strongly discouraged him. I wanted to concentrate on the evening and dancing. Bob consequently sat around in half a funk most of the night, drinking way too much while I enjoyed the music and the people.

Bob was well under the influence by the time we got back to the Palmer House. I decided to have him spend the night and managed to get him up to my room without attracting undue attention. My doorman who appreciated my shows, helped me with Bob.

Once back in the room, we stripped naked and climbed into bed. Bob only got as far as putting his arm around me and groping my tits for a few seconds before he passed out for the rest of the evening.

I was up, showered, and dressed the next morning before Bob woke up. When he did struggle awake, I told him, "Bob, I want to spend the day at the Shedd aquarium first and the rest of it at the Field Museum of Natural History. Sooo, you had best get home and clean up and pick me up back here in two hours. Best hop to it, fella!"

While I busied myself in the sitting room, among other things, ordering him a taxi, Bob hopped to it as best he could, groaning into his clothes. The front desk called to say the taxi had arrived just as Bob finished dressing. I shooed him out the suite door.

The phone rang again--it was the Chevy dealer. My new 'Vette would be ready by nine thirty a.m. the next day. Ok! Day three was it; I could now put the rest of my plan into action. Love 'em and leave 'em Bob was about to find out how it feels.

We spent a long, tiring, but for me, at least, enjoyable day at the museum and aquarium. The afternoon still had several hours left in it yet when I told Bob, "I changed my mind about the plans for tonight. I don't care how you do it, but I want you to get us on the beach somewhere on Lake Michigan as quickly as possible. You can have all of me you want--in the water!"

I just didn't tell him that my idea was to have a good fuck in Lake Michigan at the start of my odyssey on Route 66 and another in the Pacific Ocean at Santa Monica at the conclusion of my trip.

"And in between, you ask?"

Well, we'll just have to see what happens, won't we!

"What?" croaked Bob. "What did you just say?"

"You heard me, now get cracking!"

Bob must have wanted me pretty badly by then, because he got us onto a beach. It was early in the season, so the beach was deserted except for a couple sunbathing quite a distance away. I didn't think they'd be a problem.

I said, "Race you into the water!"

My clothes diappeared in a flash. I beat him, but not by much. But he did get a fine view of my bare ass. After a lot of fooling around and teasing, Bob finally got what he wanted. He pulled me to him and we clinched in a tight embrace.

Bob's mouth got busy on my neck and the side of my face, my nose, and my mouth. We were in the water just over waist deep, so he next got busy on my exposed tits. He did a good job on the nipples all around and between them with tongue and teeth. While he was doing this, his right hand was busy on my ass and his left hand was working overtime on my pussy. Both hands were, of course, under water.

I also had both hands busy between our two bodies, playing tunes on his stiff dick.

"I'm starting to get close to the limit, Jen, hop on before I blow."

I grabbed him around the neck while he grabbed me with both hands under my ass and lifted me up to his waist. The buoyancy of the water helped. I freed one hand to guide his cock to the target and sank down on his pole. We began thrusting into one another with vigor. I have to say it, but I have had far better fucks than Bob. He is great in the preliminaries, but he cums up sucking for the real fuck.

I also have to say, fucking in water is not all it's cracked up to be. Water doesn't lubricate as well as natural body fluids, at least for fucking. That may have been part of the poor fuck with Bob, but he really wasn't all that good with his pecker.

Since we never got past the foreplay before, this was my first actual fuck with Bob. Too bad. Bob managed to get himself off, but he never managed to make me orgasm with his dick, only earlier with his hands and mouth. After he climaxed, Bob's dick deflated completely and dropped out of my pussy.

We spent a very little time in post coital holding and hugging, the water was just too damned cold and we were freezing. Consequently, we ran back to the beach to dry off and dress.

I said, "Let's go back to the Palmer House and have dinner there. You can drop me first and then go to your place to clean up and dress for dinner.

Later, after a truly wonderful dinner, I once again invited Bob up to my room, "for drinks," I said. Since I had had all of Bob I wanted by now, I slipped some knock out drops into his drink and sat beside him on the couch. I guess I'm more callous than I thought about some of my partners.

It didn't take long before Bob dropped his face onto my shoulder--out cold. I stripped him down to his shorts, laid him out on the couch and covered him up with a light blanket. He would be out for about twelve hours. I spent a comfortable night alone in the big, king sized bed and was dressed, packed, and standing at the front desk by eight thirty the next morning. I had hung the "Do not disturb" sign on the door knob after I had pulled the door shut.

As I completed checking out at the front desk, my taxi arrived. The bell hop carried my luggage to the cab and I gave the driver the address of the Chevy dealer. I made a clean get away. Bob had developed some feelings for me and I wondered how he would deal with the situation.

I paid off the cabbie in front of the Chevy dealer and walked into the building and asked for the manager. A middle aged, very good looking man came out and said, "Hello, my name is Richard. What may I do to help you this morning, Miss?"

I said, "My name is Jen O'Connell and I believe you have a car ready for me, yes?"

"Oh indeed we do!" exclaimed Richard. "Please, step into my office where we can deal with the paper work and then you can be on your way!"

The paper work took forty minutes or more. I gave him the name of my Peoria banking institution to check out and there were interminable papers to fill out. Richard accepted my bank draft for the full amount of the car and the car was brought out front, full of gas as requested. A temporary license paper was affixed to the rear window and I was finally ready to go.

I shook hands with Richard as he wished me happy motoring. He had a wistful look on his face as he eyed my legs and crotch when he helped me into the Vette. I gave him a long look between my legs as I took my time and slowly settled down behind the wheel. It was difficult to get down into that low car and sit on your butt with your legs nearly straight out in front, parallel to the floor.

When I turned the key, the Vette engine growled to life through the dual exhausts, full duals from the headers back. It was an unbelievably gratifying sound. I revved up once and backed off, shifted into first gear, and was off, burning rubber from the start and with each shift thereafter. God, what a car.

Finally! I was on my way. Lead me to the starting line.

But which one? The start of Route 66 has moved a few times. Originally, the road began on Jackson Boulevard at Michigan Avenue. In 1933, the start, and the Chicago end was moved east onto the reclaimed land for the world's fair to Jackson and Lake Shore Drive. In 1955, Jackson Boulevard became one way, eastbound, west of Michigan Avenue and Adams Street became the westbound U.S. 66. However, the start remained on Jackson at Lake Shore and that is where I started my Route 66 adventure.

The opening segment of the "Mother Road," Illinois Route 66, stretched out for 290 miles ahead of me to the Mississippi. Interestingly, its (Illinois Route 66) original two lanes were completely paved before the official inauguration of the overall route in 1926. Much of the rest of the original road, in 1926, was still either dirt or gravel.

Anyway, I drove west on Jackson, past Buckingham fountain just to the south and turned right (north) onto Michigan Avenue, passing the historic Santa Fe building at 224 South Michigan Avenue. I continued until I could turn left (west) onto Adams Street. passing the Art Institute just north of Adams on Michigan Avenue. Orchestra Hall sat on the corner of Michigan Avenue and Adams. The route continued on over the South Branch of the Chicago River with Union Station at the intersection with South Canal Street.

At an elapsed mileage of two point six miles, or as I will express it throughout the story, two point six miles past go, I crossed Ashland Avenue and turned southwest onto Ogden Avenue. Very quickly that led me into Cicero, once a main part of Al Capone's empire. Next came Berwyn, and then Lyons, still on Ogden Avenue.

Entering Lyons I had to turn left (south) onto Harlem Avenue, which is also State Route 43. This was the post 1928 alignment. Before that, the route continued on Ogden. At about a half mile down Harlem, I had to turn right onto Joliet Road, wind my way through Lyons, and then cross the Des Plaines River.

It was really too early to make too much of a judgment about my new 'Vette, but I had driven enough to come up with her name: Miss Swifty or just Swifty, for short. And was she ever swift! Those fuel injected horses would really move if I put my foot down. Once out in the open, away from the city streets, I did put my foot down several times. Ya Hoo! Go Swifty, go!

By design, Route 66 connected all the little hamlets along the way that it could. There are a lot of them on the way to Joliet. Another route realignment occurred in 1940 at Joliet, but I'll not go into detail on it.

On Joliet Road, I managed to find my way to the White Fence Farm restaurant, in business since 1954, and had an excellent chicken dinner at a little after high noon. Back on the road again, I reached Wilmington at fifty-eight miles out of Chicago or, as I said I'd call it, fifty-eight miles past go.

It was at Wilmington that I decided to get onto the newer, post 1940, four lane Route 66 for the rest of the trip to Bloomington. The original two lane only existed in short segments by the small hamlets anyway by that time.

I wanted to let out Swifty and let her run when I could, and I needed a more open and a straighter road for that. I also needed fewer close spaced little towns for now. The four lane modern version of the road would be much better. I intended to get off at selected spots to see the sights.

"Why," you ask, "does the older, two lane Route 66 (and other roads) meander and wander so much?" Well, as I have said at least twice already, the original Route 66 was designed to connect many of the little hamlets as well as the larger population centers. That's one reason.

A second reason was, money--or rather the lack of it. I did do some research before leaving on this trip, for a variety of reasons, one of which was so I would know points of interest to stop and gawk. But in the process of this research, I remember this statement by Mr. Cyrus Avery of Tulsa who was one of the founding fathers of the original Route 66. He stated the reason for the meandering better than any others I have heard or read about.

He said, "Highways were routed around hills instead of through them, bridges were built eighteen feet wide, section lines were followed despite the right angle turns, because these things made roads cheaper. There wasn't any of this big earth moving machinery then, and we could build miles of roads for what it would have cost to cut through one little hill. If we had made bridges two feet wider, we couldn't have built as many bridges--we had just so much money and there never was enough."