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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, istanbul escort 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.
“You keep that up any longer and I’m gonna cum without you even touching my pussy. Now fuck me hard. PLEASE!”
The next morning, there were a few people on the dock that gave us knowing glances. I had chosen May 10 as departure day for no special reason other than to have a target date and that date was coming soon. I stopped by the office to see how Jean and Lois were doing. Everything was going well. They gave me hugs and kisses and wished me a good trip. We set up to call on Mondays for a maximum of 15 minutes to deal with any issues that may come up.
Without Debbie’s knowledge, I arranged with Tony for her to have a week vacation. I thought she might like to spend the first week of my trip with me and I wanted an extra set of eyes as we went thru the waters around NYC to the Hudson River and points north.
Debbie spent my last night on the boat with me. I ordered Chinese and had it delivered. We were naked almost before we finished dinner. I used every trick I had learned to pleasure a woman that night and during a mind blowing orgasm, she passed out. It took a few minutes, but she regained some semblance of awareness as she stared into my eyes and smiled. I got a great hug and kiss from her before she sucked my cock in and sucked my balls dry as powder. The next morning was another loving session before my friends started showing up for my 10:00 departure.
The engine was at idle when I pulled out a bag of traveling clothes for Debbie.
“It’s traveling clothes for you. I arranged for you to get a weeks vacation so you could travel up the Hudson with me, if you want that is.”
“A vacation? on this boat? You’re kidding right?”
“No, but you better make up your mind quick. I’m casting off in about 5 minutes. Here comes the gang now.”
“I’m in, all in!”
She jumped into my arms, wrapped her legs around me and dry humped me as she kissed me.
Tony said, “I take it you told her and she’s going with ya.” He was laughing.
Tony cast off the lines and I moved the boat away from the dock. I was on my way!
There was no time table for this trip. I was going to stop and see local attractions and take as much time as I wanted. My goal for today was to get as far up the Hudson River as possible to get away from the bulk of the commercial traffic on the river in the NYC area. I had Debbie looking for marinas to call and arrange for dock space for the evening in addition to helping me watch all the marine traffic.
We passed Lady Liberty and entered the river. The Erie Canal was 134 miles away, but with all the sights and history along the river, I thought it might take me several days. The estates of the Rockefellers, VanderBuilts, Franklin Roosevelt, Martin VanBuren and others would be interesting esenyurt escort to visit. In addition, I planned to have dinner at the Culinary Institute of America (CIA) one evening.
It was going to take some time adjusting to boat speed as opposed to 70-80 mph like on land. At first, I wanted the boat to go faster, it was taking for ever to get anywhere. After a couple of hours, I began to sit back and enjoy the scenery, the other boats, and everything that I had never seen from this perspective. Passing under the Verrazano Narrows bridge and later the Tappan Zee bridge was cool. Usually I was driving over them.
Debbie disappeared from the bridge and returned a few minutes later in a pair of shorts and a very tight tee shirt. It was obvious she had lost her bra. She also brought me a cup of coffee and as she placed it in the cup holder, she rubbed her tits along my back and arm.
“Hope you find this restful today. You’re going to be a very busy man tonight!”
Laughing, she sat down next to me and we started talking about which marina to call for tonights docking. The conversation had a lot of sexual undertones that had both of us laughing and enjoying the day. We chose our preferred marina, Debbie called and made arrangements for the night. We were to call on the radio when we entered the harbor and they would direct us to our assigned slip.
The dock hand had just finished tying off our lines and making us secure for the night. Debbie reached over, rubbed my cock and said, “You did good.” The banter got ratcheted up a notch as we prepared to go to dinner.
Dinner was at a small local restaurant that we walked to. We both had a couple of glasses of wine which seemed to bring on the yawns from both of us. I think being outdoors in the sun all day, the knowledge that after months of preparation I was finally on my way, along with the wine had made me very tired. I think it had the same affect on Debbie. We got back to the boat, undressed, had some sex and fell asleep. The night was not nearly as wild as I, and I think Debbie, thought it would be.
The morning sex was a little wilder than the night before, but I wanted to get going so we saved ourselves for later. Working our way up river, we passed the US Military Academy at West Point. I was surprised that my depth finder showed the water to be a little over 200 feet deep. I never realized how deep the Hudson River was, but I never gave it too much thought either. We found a place to stop for lunch that had a nice transient dock and enjoyed a leisurely lunch before getting back on the river. It was a beautiful May day, with bright sun and moderate temperatures. Debbie came back on the bridge in a VERY tiny bikini top. She rubbed my cock to assure that she was getting the desired response from me. She was. She also got some whistles from other boaters which caused her to laugh, standup, wave, and of course, give them a better view of her tits.
That evening, we found a slip that was near the CIA, Roosevelt and VanderBilt mansions. After dinner at a local diner, Debbie and I returned to the boat and slipped out of our clothes. We spent a couple of hours enjoying the pleasures of each others bodies. I continued to practice the things that I had learned from Holly and it always brought both of us a great deal of pleasure. It always started with the kiss and progressed from there. I played with her nipples and had her squealing before moving into a 69 position so I could enjoy her pussy as she sucked my cock. I loved the taste of her pussy. After getting her off with my tongue and fingers, she climbed aboard me and we chased orgasms until we both were worn out. Together we lay sweating, covered in cum and enjoying our post orgasmic glow as we drifted off to sleep our bodies intertwined with each other.
Debbie woke up the next morning with my head buried between her legs eating a wonderful pussy breakfast. She came as she woke up. She then devoured my cock and had a creamy protein shake for her own breakfast. I recommend this as a great way to start a stress free day.
First item for the day was the VanderBuilt Mansion. The mansion is a beautiful example of the Gilded Age and we enjoyed the tour of the house and the gardens. Our guide was an older woman but I enjoyed walking behind her and admiring her assets. Debbie punched me in the arm when she caught me. I just laughed and winked at her as I tried to pinch her ass.
The Roosevelt Home was closed for the day for maintenance so we explored Hyde Park and the Rhinebeck area and wondered thru antique shops. I called the CIA for reservations but they were booked for the evening. I explained our situation and that I had hired several of their graduates for my catering business and they became a little more accommodating. We got a reservation for the next evening.
Back on the boat, Debbie and I were naked again and really got into it. Again, it started with a kiss, but this time I continued to kiss and lick my way all around her body. She arched her ass in the air beylikdüzü escort when I kissed it and rimmed her back door. I also had fingers in her pussy and my thumb on her clit which brought a very loud scream of pleasure from her. I hoped the neighbors weren’t listening too close. I moved on to kiss and lick her pussy and again she screamed as she came. Kissing my way up her body, I again teased her nipples before she grabbed a handful of my hair and dragged me up to her lips saying, “Now fucking fuck me. I want your cock buried deep in my pussy and I better cum several more times before you dump your load.” I think I counted four orgasms before I blew my balls deep in her pussy.
The next day we toured the Roosevelt home. Our guide was a woman about my age with a nice figure. My arm got black and blue from Debbie hitting me every time she caught me admiring the guide.
Dinner at the CIA was all I hoped it would be. The students are the servers. We had a very attractive young lady serve our drinks and I flirted openly with her. That got me a kick in the shins, but she provided outstanding service and seemed to enjoy my flirting because she flirted back. A young man served us our bread and rolls and Debbie did the flirting. I was tempted to kick her shins but thought better of it. Each course had a different server and we flirted with all of them. It was a wonderful way to spend a couple of hours and we enjoyed ourselves immensely.
On the way back to the boat, Debbie asked, “Have you ever been in a threesome?”
“Not yet, would you like to have one?”
“I’ve thought about it a few times, but If I were, it would be with two guys. I’m not ready to try a girl.”
Back at the boat, our loving was a little more intense. The next day, Debbie was catching a train in Poughkeepsie that would take her back to the city. She screamed with each orgasm and I worked her up to one brain scrambling orgasmic ride that caused her to pass out for a few minutes.
The next morning was a slow fuck and breakfast together. At the train station, we kissed, hugged, promised to stay in touch and I said I would see her this winter when I came back to the Island.
The train left on time, we waved as it pulled out of the station and I realized I was going to miss her.
There is much to see along the Hudson River and I took my time and saw a lot of it. I also met a lot of other people in various stages of doing The Loop. They called themselves ‘The Loopers’. Many offered advice and suggested places to stay, see, eat and were generally a group of very nice people. Most were married couples with kids or grand kids that would join them for a weekend, a week or two and sometimes for the entire summer. Opportunities to meet single, dateable women seemed to be limited to shore bound women at various venues along the river. Occasionally, one would want to see the boat, but nothing sexual happened.
It took me to mid-June to get to the entrance to the Erie Canal. I wasn’t sure if I was excited or dreading entering the canal. I was going to be entering the first of six locks that would lift Second Chance about 180 ft above the Hudson River and then another 16 locks that would put me in Oneida Lake near Syracuse. Timing between the locks is based on speed limits that the canal imposes on boaters so getting to a lock early by speeding just makes you wait longer.
As I approached the first lock at Albany, I slowly entered with bumpers out and a hook to help hold the boat when the water swirled in and wanted to move the boat. A 36 ft boat is a lot of boat to handle by oneself thru the locks. As I struggled with getting the boat under control, a voice yelled out, “Hey mister. Do ya need help getting that boat locked thru? We’ll help if you let us ride with ya to Syracuse.”
Looking up, I saw two young girls looking at me. They didn’t look to be out of high school and my first thought was JAIL!
“We’re students at SU and looking for a ride. This is more fun than going the Thruway. Sure you don’t need help?”
“OK, I could use the help, but it’s a slow ride to Syracuse.”
“We did this last year, had a ball. When you get to the top of this lock, we’ll board. We’ll go get our bags and be back in a few minutes.”
As the lock gate opened, I moved to the sea wall and the girls threw their bags on the boat and jumped on.
“Hi, I’m Julie and this is Amy. You are?”
“HI, I’m Jim.”
“How far you going on the ditch?”
“All the way to Buffalo. How old are you two?”
“I’m just turned 22 and Amy will be 22 next month. I’m a law student at SU and Amy wants to be a sports broadcaster.”
“Ya, I want to be the first woman to do play call for a NHL game. I think that would be so cool. Do you like hockey?”
“I have season tickets for the Islanders.”
“Wow, nice. We best get going or we’re going to miss the next lock opening.”
We began to work our way thru the locks. It was obvious that they had done this many times. They worked together without a lot of words, yelled instructions to me on the bridge and we worked our way thru the locks. Even between locks they kept a banter going that made me laugh. They wore tight jean shorts, tee shirts although you could see a bikini top under the shirts. Both were about 5-7 or 5-8 tall, and well proportioned. Altogether, they were easy on the eyes.
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