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This set of stories are meant to be read as chapters in a book. If you haven’t read the previous chapters of the Great Loop, I recommend you do to better understand the characters.

All characters are fictional. Obviously, many of the place locations are real.


Sorry for the delay in this chapter. Family, holidays and other issues reduced the time available for writing. Please enjoy this chapter.


I was waiting for my baggage at O’Hare International Airport when I felt 4 arms wrapping around my back. It was Jill and BJ. They were laughing and we hugged and kissed as we waited. Eventually all my bags were accounted for and we left for the girls house.

Back at the house, it wasn’t long before we were all naked and reacquainting ourselves with each others body. After a rousing session of sex, we spent time catching up on all that had happened since we last saw each other. Jill was almost done with her continuing education classes for her Physical Therapy License, BJ had been promoted to a supervisory position, and I, of course, had sold the business.

When I had called the marina and told them I’d like Second Chance back in the water by April 15 they had no problems. Most of the maintenance had already been completed. I would need a few days to get everything organized on the boat and I wanted to take it for a test run before entering the Illinois River and continuing my trip. While back on Long Island for the winter, I had spent time planning this summers boating. I set a goal of departing on May 1 and reaching the Gulf of Mexico by Christmas. To start the trip, I had to get to the Illinois River from Lake Michigan. The scenic route would take me right through downtown Chicago which would be really cool, however, you have to be able to pass under a 17 foot high bridge. Since my boat is 18ft – 8 inches high with the radio antenna down, that wasn’t an option for me. I had to go south of Chicago to what’s called the Cal-Sag route.

Since it was early April, Jill arranged time away from the club. We used the tickets she gave me for Christmas and toured the Oak Park historical district of Chicago. We got lucky and the day our tickets were for was a beautiful spring day. The trees were starting to bloom, the sky was blue, and the sun was shining. The tour started at Wright’s first house where he lived with his wife and children. Next door was his studio where he and his staff developed some of his most famous structures. The most fascinating room in the house, to me, was the playroom. It has a barrel-vaulted ceiling that is 15 feet high, the windows are at the height of a child, and above the fireplace is a mural that is based on The Arabian Nights. The studio was also interesting, especially the way he used windows and light.

After touring the home and studio, we took a guided walking tour of the area and saw seven other homes he had designed. Fortunately, the group consisted of only 6 people. I say fortunately because I seemed to monopolize the guide with questions. It was a wonderful day. While taking the walking tour, two houses were of real interest to me, the Frank Thomas and Arthur Heurtley houses. I told Jill that I would like to come back and tour them also if we had an opportunity. I also told her that I wanted to tour the Frederick C. Robie house. She said the Heurtley house is a private home (I missed that during the guided tour – duh) and does not offer tours. She would see what she could do about the others.

A week later, we were touring the Thomas and Robie homes. I thought to myself, she must have some pretty good contacts.

After the boat was in the water, we took the totes down to the marina and began organizing the boat. I brought my clothes down, except for what I needed around town, and put them on board. I had to rethink how I organized the closet because Jill would have her clothes as well. I hoped not too many. I also checked out all the maintenance work I had had done. All appeared well. I started watching the weather closer so we could take the boat out for a day and check everything out.

Towards the end of April, a window of opportunity appeared and I asked the girls if they wanted to go for a boat ride. Both got excited. BJ would have to arrange for the day off which would be difficult because she was in the middle of tax season, but Jill was getting ready to leave the club for the summer so that wouldn’t pose a problem. When the day arrived, we were at the boat early. Jill showed BJ around while I started the engine and let it warm up, I pulled fenders, thru off the lines and eased out of the slip. I pulled over to the fuel dock and topped off the fuel tanks and put water in the water tank. Slowly, we left the harbor, motored past Navy Pier and headed for open water.

There weren’t many boats on the water because it was early in the season and the water was still cold. Also, it was a week day. After the engine was up to temperature and Antep Bayan Escort running smoothly, I had Jill take the helm and I went below to check for leaks and other potential problems. I didn’t find any. The sun was warm and after we got out from the coast a ways, BJ pulled off her top and enjoyed the sun on her bare boobs. Jill wasn’t far behind her. They certainly can be a distraction. After about 4 hours, we headed back to the slip, tied off, secured the boat, and headed for home. BJ said, “Now I understand the fascination Jill had with being on the water. I’m definitely going to join you for a week or two this summer. The rolling of the boat and the sun on my boobs got me all wet between my legs. Are you going to do anything about that, Jim?”

“I think I can handle that task. I may need some help from Jill though.”

Back at the house, it wasn’t long before Jill and I were licking BJ’s legs and pussy. She had a massive orgasm. Jill and I shared an orgasm as well and then we all slept together in Jill’s bed.

We only had a week before my planned departure. Jill had sorted out her clothes and I was pleasantly surprised that she didn’t try to bring her entire wardrobe. She would be traveling light. I also wanted to use the tickets Jill had given me to visit Taliesin in southern Wisconsin before we left and Jill wanted to spend a day with her mother before we left.

Jill was able to get the date for our tickets to Taliesin changed and we headed north to Spring Green, Wisconsin. Once again we lucked out with the weather. Sunny and warm. It was a great day for touring the 600 acre estate. I was surprised to learn that the estate is privately owned and only guided tours are allowed. Normally, they start May 1, but Jill had done some magic and we had a private guided tour. Wright was forced to leave Chicago with his mistress and went to Taliesin. There the story gets complicated but is worth reading about.

Later in the week, we went to see Jill’s mom. I tagged along even though I didn’t want to. Her mom was a nice lady, but seemed perpetually sad. There were two casket trifold flags in the living room on the mantle. One belonged to Jill’s dad and the other to her brother. I didn’t know the story behind them but waited to we got in the car before asking about them. As we were leaving, Jill’s mom said to me, “take good care of my daughter. She’s all I have left.” I promised I would.

Back in the car, I asked Jill, “What was she talking about, you’re all she has left and what’s the story about the tri-folds?”

“Those flags are from my dads and brothers military funerals. Dad was a career Army man and died in Iraq. It broke mom’s heart. Two years later, Tommy, my brother and a Navy Seal, didn’t survive a mission. We don’t know what happen because the mission remains classified. That almost killed mom. They’re both buried at Arlington Cemetery. My mom visits them every Memorial Day. I used to go with her, but don’t anymore. She spends the day talking to them, crying, and it isn’t very much fun. I imagine the markers have tear stains on them. I remember the funerals. I cried and cried at my dad’s and all I could think about was not going to the planetarium with my dad any more. I was in college”.

“Tommy and I were the closest of friends. I was the only person he allowed to call him Tommy. We confided every thing in each other. Whenever we wrestled or shot hoops, he always let me win. The only sport he wouldn’t let me win was swimming. We raced at the club all the time. I almost beat him a couple of times and he just laughed at me. He intimidated many of the boys that would come over to take me out on a date. Most of them didn’t ask me out again. He was both very protective and very supportive of me. I loved being seen with him when he was in his dress uniform. He was so handsome. Didn’t you notice the picture in my bedroom? It is of my dad in his dress uniform next to my brother in his dress uniform. They are also side by side in their fatigues with their weapons and other battle gear. I miss both of them, wish I could change things, but I can’t, so have moved on. I think they’d both agree with that. So, I’m my mom’s only child. She would die if anything happened to me. If she had her way, I would be living at home with her and she would be way over protective of me. I do try to see her once a week when I’m in Chicago. When I told her I was going with you, she cried and was worried she wouldn’t see me again. I told her I would call her every week and come home when I got the chance.”

She had tears in her eyes. I said, “Hey, I’m sorry, I didn’t know.”

I hugged her close and then we drove back to her place. I immediately went to her room to look at the photos of her dad and brother. They looked like fine men. I said a quiet thank you to both of them. Jill came in, slipped an arm around me and we just stood there for a couple of minutes without saying anything.

That night, we made love with passion and joy. I think we were both glad to be alive and with each other. BJ was still working all hours finishing up taxes.

The next two days were hectic as we finished getting the boat ready, Jill took care of some last minute things and chased down the status of her Physical Therapy license. Our last night at Jill’s, I took BJ and Jill out to dinner. After dinner it was all out sex. BJ wanted to “store up until I see you again.” We ate her pussy, sucked her nipples, fingered her, fucked her and gave her several orgasms before we all fell asleep. The next morning, was a tearful goodbye for Jill and BJ and I got a passionate hug from BJ before she left for work. She was going to pick up Jill’s car at the marina later in the week, so we made sure she had a set of keys.

Finally, we were off. It was great to be on the boat again, and even better to be on the boat with Jill. We headed south to the Cal-Sag route. As we left the lake, I realized that for the next 7 or so months, I would be on rivers or man-made lakes. I wouldn’t see open water again until I got to the Gulf. I explained this to Jill, but she was excited to be underway and looking forward to seeing all the sights along the rivers.

We eventually merged with where the Chicago route would have taken us and the next obstacle was ‘The Bridge’. It was about 3 miles down river. ‘The Bridge’ is a fixed bridge that is 19′ 1″ above the water. If you can’t clear it, you have to make a U-turn and you can’t complete the Loop. My boat is 18′ – 8″ so I should clear it with inches to spare. As we approached the bridge, I slowed to as slow as I could go, lowered the radio antenna, took a deep breath and proceeded under the bridge with no problems. Next up was a huge sign saying “DANGER” that warned we were entering the US Coast Guards’ Electric Asian Carp Barrier Field. This barrier creates an electric field that shocks the fish and prevents them from getting to the Great Lakes. We were required to wear a Type 1 PFD while transiting this barrier.

Asian Carp are huge fish that weigh as much as 150 pounds and start jumping out of the water at the sound of a passing boat. After we got south of the barrier, we got into a group of these fish and they started jumping. A few landed on the bow and slid back into the water, but I can’t imagine how much damage they could do to a smaller boat or a person if one were to be hit by a carp.

After clearing this area, we settled down to cruising the water way. Only 297 miles on the Illinois River to the mighty Mississippi. We stopped for lunch at a restaurant that had docks and walked around a little before continuing on down river. Brandon Road lock was the first lock that we came to. These locks were much larger than the locks on the Erie Canal because of all the barge traffic on the river. This was also Jill’s first experience at locking thru. She was nervous, excited and full of nervous energy as we approached the lock and rode the water to the new level. As the water lowered, the clams that were attached to the walls would spray water as they equalized pressure. Jill thought they were pissing on her until I explained what was happening. Then she laughed it off. We spent the night tied to a sea wall. Together, we enjoyed a drink and a light dinner before heading for bed. Jill called her mother and BJ and told them of the days events and the locking thru experience. As we undressed for bed, Jill put her arms around my neck and kissed me with passion. Afterwards she said, “I am soooooo glad we are doing this! Now, make love to me.” Most of the time I do as I’m told, and this was one of them.

The next day, we woke with our usual round of oral sex and then headed on down river. Jill would have stopped at every little community we passed if I’d have let her, but we needed to move along. We passed under the Interstate 55 bridge and passed the Kankakee River. Coming up were the Dresden Island lock and the Marseille lock. Sometimes we got lucky and was able to enter the lock after a short wait, other times, we circled and waited longer for our turn to enter the lock.

We spent the night at Starved Rock Marina that had all the services we needed. We ate dinner at the Captains Cove Restaurant and then Jill called her mother and BJ to tell them about our day. We met other Loopers that made suggestions for places to stay, eat, and sights to see. The conversations also included kids, grandkids, and the typical where you from, what do/did you do, etc. Jill was enjoying it immensely. In bed that night, Jill rode me cowgirl and reverse cowgirl style as we pleasured each other.

The next morning, I woke to Jill stroking my morning wood and kissing me. We pleasured each other before having some coffee and moving on. I can’t say it enough, there is no better way to start the day! The day was rainy with thunder storms in the area. There was also a cool breeze blowing so we stayed at the inside bridge as we motored along. Jill would occasionally rub my cock thru my pants and I would cop a feel of her braless boobs in return. The traffic was light on the river with some barge traffic, so we did have to pay attention to what was happening around us. We were also seeing a lot of Bald Eagles. I got my new camera out and started taking pictures while Jill was at the helm.

As we cruised down the river, we stopped at a variety of interesting towns and villages and took in the sights and local food. Jill is even more social than I am and really enjoyed meeting new people and kids. She had a way with everyone that made it easy to talk to her. We met a lot of interesting people with all different kinds of stories to tell. I kept thinking I needed to write these stories down and maybe someday write a book, but it never happened. One couple we met had their 3 children with them and had been living on the boat for 2 years. They were doing the great loop in the opposite direction from us. The mother was home schooling the kids, dad was a writer and could work from the boat, mom had some sort of business where she did free lance editing, proof reading, typing and office services that allowed her to work from the boat as well. The kids were 14, 12, and 9 and were all very well spoken, intelligent, and polite. I enjoyed asking them questions and learning just how much better educated they were than many public school kids.

As we got closer to Peoria, I started watching for the Illinois Valley Yacht Club. I needed to stop there to fuel up since that was the last place for diesel fuel until Grafton and the Mississippi River. After finding the club, we filled our fuel tanks, pumped out our dirty water tanks, got fresh water and enjoyed another evening meeting new people, having a few drinks and then going to dinner with some of our new friends. My computers screen saver file was growing with each stop as I continued to add photos of people we met.

We got to Peoria and found the Peoria Transient Marina that a Looper had told us about. The docking rates were great and the water front was outstanding. There were restaurants, a museum, and a theater within easy walking distance. We had a choice of restaurants, picked a seafood one and had an enjoyable dinner. Back at the boat, we enjoyed a glass of wine before heading for bed and a wonderful night of pleasure. Jill has the most wonderful skin. Smooth, firm, and very enjoyable to kiss, touch, lick and even rub a cock on. I couldn’t get enough of it that night, Finally she pleaded with me to fuck her and I did making her cum several times before I dumped a bucket full of spunk in her pussy. We kissed some more before falling asleep.

We spent another day in Peoria, walked around the Peoria Riverfront Museum, checked out the theater, ate at a different restaurant and then explored some more. Back at the boat we had a happy hour with some fellow boaters and then went to a steak house for dinner as a group. That night, Jill climbed on top of me and used every four letter word she could think of as we both came together.

We settled into a routine. The morning started with blow jobs and pussy eating. Breakfast was coffee and whatever we could find. While on the water we watched the banks for wildlife, other boats, talked about our hopes, dreams, past and anything else we could think of. We took turns at the helm. After stops in Beardstown, Naples and Hardin and lunch at the Illinois Riverdock, we reached the mighty Mississippi River and got a slip at the Grafton Harbor Marina. This is a 200 slip marina with a nice general store, restaurant, showers, and laundry facilities. There was about two dozen loopers there while we were there. Some were going our way, others were going the opposite way. All were excited to share information about places to see, things to do, restaurants, good and bad marinas.

The showers were awesome. Jill and I took long hot showers together, sometimes very early in the morning or late in the night so that we wouldn’t disturb others with our love making. I loved fucking Jill with her hair all wet and her body all soaped up. She would rub her soapy boobs against my back to wash my back which invariably led to bending her over and sliding my cock in her pussy from behind while I leaned forward and played with her boobs and nipples. Drying each other off was fun as well.

BJ flew into St. Louis and met up with us at the marina. She was going to be with us for the next two weeks or until we got to Louisville. As she was running down the dock, Jill was running up the dock. When they met and kissed the passion was palatable. They got more than a few shocked looks from people along the dock. Walking towards the boat, they were both talking and I don’t think either heard what the other said. Jill had her arm around BJ’s waist and BJ carried her bag. Once on the boat, I too, got a passionate kiss from BJ. I was sure that there would be a lot of wagging tongues around the marina now! BJ also had a surprise for Jill, her Physical Therapy License had finally arrived in the mail. Jill screamed with glee and kissed both of us.

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