This set of stories are meant to be read as chapters in a book. If you haven't read Great Loop 1, I recommend you do to better understand the characters.
All characters are fictional. Obviously, many of the place locations are real.
Debbie lay with her head on my chest as my cock softened in her pussy. We had just finished an orgasmic ride together and were coming back to reality. Wiggling her hips on my cock, "Jezz are you good. I can't get enough of you. How soon can you go again?"
Laughing, "In a while. How about some water or juice or something?"
We sat naked in the kitchen as we had a glass of something. I started telling her more about The Loop, things I had learned, my decision to turn over the daily operation of the business to Jean and Lois. I told her I was going to have Tony (her boss) start looking for a used cruising boat for me. I would email her the specs to pass on for me. She offered to house sit for me if I wanted someone in the house. Another thing I hadn't considered. The more we talked, the more my desire to make the trip happen came clearer.
Finally, she stood, slid into my lap, kissed me and we were off. We didn't make it out of the kitchen. I sat her on the island and ate her pussy until she was popping off small orgasms. Bending her over the island, I entered her and used every trick I could think of until she scrambled her brains with a huge orgasm and I blew my load deep in her. I carried her off to bed as she slowly returned to normal. A big smile, a kiss and we spooned as we fell asleep.
Debbie and I continued to see each other and every time it was sex. We went to hockey games and occasionally went to a show or dinner, but mostly it was the sex. Considering I was going to be leaving for 2-3 years, we were reluctant to make any long term commitments to each other.
I put together some specifications for the boat I wanted and sent it to Tony. I wanted it less than 40 ft with good sight lines. It should draw 3-4 feet of water and could not be any taller than 19' -1" in order to clear the lowest fixed bridge on the loop. I liked the looks of trawlers and tug style boats so he should focus on them and it should be completely self contained so I could live on board. We also established a budget.
I had an appointment with Ben.
"Jim, I didn't think you could do it, but you're down 25 pounds, your BP is down, you look great and Dr. Lindquist says your sex life is probably better than most peoples. Now, what about a vacation? Go to the islands, take a cruise, go to Europe, go to Hawaii, but take a vacation."
I told him about The Loop and my plans to be gone 2-3 years and turning the business over to Jean and Lois while I was gone. He almost danced a jig he got so excited.
"That's great, wow, would that be fun or what? 2-3 YEARS! I'm jealous. Good for you. When do you leave?"
"I haven't picked a date yet because I haven't sold the sail boat or found a cruiser to buy. There are a lot of pieces that have to fall into place yet, but I'll let you know when I'm leaving."
Now I was committed. People knew about the plans, no backing out now.
I spent less and less time at work and I adjusted both Jean's and Lois' salary to reflect their increased responsibilities.
I continued to research The Loop, I even went to the city to visit the NYC library and found a wealth of information; charts, books, diaries, blogs, and a host of other information that might be useful. I was reading everything I could find.
In early March, Tony called. An offer for my boat had been presented. He thought it was a solid offer, the buyer had provided a non-refundable deposit and could have a check in my hands within 10 days. We negotiated the price a little and then the boat was sold. First piece in place.
I also put my house on the market. Prices were beginning to rise and having an empty house for 2-3 years was not a good idea, nor was renting it. A house down the street sold for $750k and it wasn't as big as mine and hadn't been upgraded in years. I felt mine would sell quickly at an attractive price. Ten days later my house was in a bidding war. It sold for $25k more than my asking price and it was a cash sale. I had to be out by the end of the month. Second piece in place.
Tony was having a problem finding me a boat to buy. Either they were too big, too expensive, needed too much work, too old or weren't a tug or trawler style boat. He found one near Boston, but it was new and way over budget. I decided to look at it. I was anxious to get going.
I bought the boat. It met all my needs and was beautiful. I named her
"Second Chance"
. The dealer offered to have a captain bring the boat south to Long Island, but I wanted to do it when I could ride with him so I could learn the boat, the electronics, handling, the joy stick docking system, etc. We scheduled it for the end of April. Third piece in place.
Debbie helped me pick out appropriate dishes, glassware and deck furniture. She was a fount of information about the best places to buy charts, reference material and other material I would want on the boat.
I flew to Boston, wrote the final check and the boat was mine. The dealer had provided a recommended spare parts list and had stored the ones I had bought on board for me. I met the captain that would help me take the boat to Long Island. As we cast off, I let him take the boat out of the harbor before taking the wheel. He had me go through all the screens on both displays that showed charts, soundings, way points and all the other functions that were available to me. We found calm water and he had me move the boat with the joy stick as if I was docking the boat. What a joy that was! We spent the night at a marina in Rhode Island and he made me dock the boat and take it out the harbor the next morning. We crossed a rough Long Island sound, around Montauk point and down the south shore to Tony's marina where I docked it without breaking anything. We were met by Tony, Debbie, Jean, Lois and Ben even showed up. All got a tour of the boat and we had a drink to toast
"Second Chance" .
Debbie spent the night on the boat with me. We fucked in every area of the boat except the engine room. I am sure many people heard her orgasmic screams, but it was some of our best sex. She helped me organize everything I had bought for the boat and get it stored properly. The chief mechanic at the marina spent a couple days walking my thru all the systems on board. The AC/Heat, plumbing, electrical, and the engine and associated components. He showed me how to change fuel filters, water filters, and which fittings would most likely need tightening after a few hundred hours. He made sure I had all the necessary tools to do the basic maintenance that I would be performing. He also showed me some tricks of the trade.
Debbie spent the entire week on board as I was learning about the boat. When she arrived after work she would make me show her everything I had learned that day. That put us in some unique positions that made for some fun body contact. I learned that Debbie has very sensitive nipples. I used that to my advantage one night and spent almost an entire hour kissing, licking, pinching, pulling, rolling and playing with her nipples.
