Kaye's Trip to the Islands

Anthology of Sailing - Story 5: Kaye's Trip to the Islands

Kaye lay on her back and clutched and grabbed the sheets with her hands. Every muscle in her body tensed as she let out a scream and her pussy began squeezing my cock. That did it for me and I knew I couldn't hold it off any more. I pushed into her as hard and deep as I could and I shot out 35 years of lust, passion, desire, regret, and a dozen other emotions deep into the pussy of the goddess I had desired since high school.

It started in my freshman year of high school. I had transferred to a new school and there she was - the most beautiful girl in the world. It wasn't just me, everyone thought she was. Always voted prettiest girl in class for all 4 years of high school.

She was smart too. I was a bit of a nerd, taking physics, chemistry, advanced math and Kaye was always in my classes. I got to know her fairly well just from the fact we were in a lot of the same classes.

She always had her friends but she was never one of the popular kids that was stuck up and refused to talk to anyone outside of her circle of friends. If you did something that was cool or she liked, she always came over and said nice job or I really liked that.

Her casual ability to talk to anyone was also my frustration in having any meaningful relationship with her. I was massively shy in my freshman year. I couldn't even talk to girls unless it was in a group or we were laughing about about something silly. In my junior year I decided to try out for the school play and I got a part. This pushed me into social situations that helped get me over my shyness and I got better acquainted with my classmates.

I got bolder and went out on a couple of dates. Kaye on the other hand always had a boyfriend. She was always devoted to the guy she was dating and the few times I asked her out, she always refused indicating she was dating Tommy or Mike or Dave. She went out with the weirdest guys - not the captain of the football team or the guys you would expect the prettiest girl in school to go out with. She dated the bad guys or the guys that didn't get great grades or got in trouble occasionally or occasionally she did go out with someone that was actually a good guy and got good grades. She didn't really have a "type" and she didn't really have a filter concerning the guys she would date. It was good for me because I always thought there was hope for a nerd like me.

In the back of my mind I always thought if my timing was right I would have a shot at taking her out. Every girl I dated, I compared her to Kaye. I even dated our foreign exchange student from Norway. She was every bit as beautiful as Kaye and had a delightful personality. However, after a couple of months of dating, it become obvious I wanted to have something more than a causal dating relationship and she dumped me. She made it clear she didn't want that kind of relationship and thought it best that we end it now. Heartbroken, I realized she was right. If we had continued to date, I would have fallen in love with her and when she went back to Norway I would have been devastated.

When I broke up with the foreign exchange student, Kaye was dating someone new. We were in our senior year and unfortunately this relationship between Kaye and her latest boyfriend, Joe, looked serious. I had wasted 4 years and had not gotten a single date with the girl of my dreams.

I went off to college and about two months after school started I discovered Kaye was attending the same university I was. In fact, she was in the girls dorm in the same quad I was in. Her building was right next door to mine. I didn't know what her relationship status was or if she was homesick or what was going on but I decided I could let her know she had a friend next door if she ever needed to talk. The reality was I needed a friend. It was really hard to make friends in a nameless sea of people at a university that was so much larger than high school. My roommates were also jerks, so I tried to spend as little time in my room as possible.

As soon as I found out she was here I decided to do a drive by. I would say hi, find out the essential information about her life and be gone in 5 minutes. I could then plan my next move with focused precision.

The initial contact with Kaye had mixed results. She was really homesick - that was good, at least from my perceived perspective. She was still dating Joe - that was bad but it explained the homesickness. Joe had such poor grades that he was unable to get into college, so he was back home working as a welder or something like that. That was awesome news, I would convince her that university men were more interesting and were more her equal. At least that was my strategy.

About 2 weeks before the end of the semester, I heard about a charity volleyball game being played. It was to be just good fun with the winner being the charity that would get all the money from the admission. It was a Thursday evening so Kaye would be in the worst of her homesickness.

I knocked on Kaye's dorm room and told her I was looking for a date (that might have been the wrong word to use and my first mistake). I begged and pleaded but she would have none of me. Realizing she needed an exit strategy she asked her roommate, Mary, to go in her place and her roommate quickly agreed.

Fuck! I had a date with a girl I didn't know and didn't really want to go out with. Meanwhile, the beautiful and intelligent Kaye was back in her room being miserable but apparently that was better than being out with me. I was hurt and angry. What was so bad about me? It didn't have to be a date. We were just two old friends from high school. I wanted her so bad but I also just needed a friend.

However, Mary didn't deserve to go out with a jerk with an attitude. I put it all back inside of me and tried to let the real me come out and get to know Mary. Despite my rejection from Kaye I really did need a friend and looked forward to getting to know Mary.

We had a nice time. It wasn't the best date I have ever been on but it was far from the worst. I walked her back to her room and departed. I wasn't sure if I was ever going to ask her out again.

Loneliness and the fact that my roommates were complete assholes drove me to the realization I needed to spend time with a friend. The last thing I needed was to spend time with Kaye and hear how wonderful Joe was. I made a date with Mary to go get a burger and we had a great time. She wasn't as beautiful as Kaye but I didn't need beautiful, I needed a friend and Mary turned out to be the perfect friend. We agreed to see each other next year when we returned from winter break.

When I saw Mary the following year, Kaye was there showing off her engagement ring. I smiled and said "nice". Inwardly I thought to myself, "you stupid bitch. What do you see in this ignorant, lazy welder? You are so smart and beautiful - you could have what ever you want. Instead you are going to end up with kids and laundry and living in a tiny house just making ends meet. Please stay in school so you have a future".

Sure enough, about mid semester Kaye announced she was quitting school and getting married that summer. Mary was invited to the wedding and I went along as her guest. I never saw Kaye again until 3 weeks ago.

Kaye lived in a small rundown house and had two children. Two years ago she caught Joe having an affair with another woman. The kids now grown, she was by herself and working as a cashier at a local store in the town where we grew up.

Mary and I dated all four years of college and got married after graduation and before I started graduate school.

Mary died of cancer last year. I'm now VP of a software company, live in a large house in Texas, have more money than I know what to do with and I'm alone.

I decided after Mary died, to try and reconnect with family and old friends. Most of the family was back in Michigan near where I grew up. I also loved to sail. It was something that Mary wasn't really into, so I never inflicted my hobby on her.

I bought a 50ft sailboat in Michigan and decided in the summers I would sail the great lakes and stop in and see family and friends. I had friends and family scattered all over the state including the upper peninsula, this seemed like the perfect mode of transportation.

My sister lives a bit inland and I decided to rent a car for a couple of days. She lives the closest to the town where we grew up so I thought it might be fun to drive the old roads and maybe even look up an old high school friend.

I actually had Kaye's address. My wife had communicated with her and stayed in touch. We always sent a Christmas card but we hadn't heard from Kaye in 15 years. None of the Christmas cards we sent, ever got returned so we assumed she still lived there. I didn't have a phone number so I didn't know what to expect when I knocked on the door.

The woman that answered the door looked a little younger than me but it could have been Kaye. "Kaye?" I asked. She told me she was a roommate and Kaye was working at the local grocery store.

I headed to the local grocery store and instantly saw Kaye working a cash register. She was a lot older than I remembered her but I hadn't seen her in 31 years. I decided to have some fun and grabbed a snack and stood in her checkout line.

Without looking up she asked me if I found everything okay.

I replied, "yes, thank you Kaye. It's good to see you again."

She looked up with a bit of confusion and then her eyes got really big. She let out a scream that everyone in the store could hear and then sprang over the counter and grabbed me by the neck to give me a hug.

Her boss came over to find out what all the commotion was about and Kaye asked if she could go on break. She took me into a little break-room and hugged me again. She began asking me a thousand questions.

"Shhh. Dinner? Say yes and all will be revealed to you," I put a finger up to her lips to get her to stop talking.

She grabbed my wrist and pulled my finger back to her lips and gave it a kiss. "yes," she whispered.

"7:00. I'll pick you up at your house," I said and turned around and left.

At 6:58 I knocked on Kaye's door and there she was, dressed in the most amazing dress. Wow, she looked great. It was conservative, but the blue dress perfectly complemented her blond hair and the red scarf set off her blue eyes.

"You look fantastic," I said looking around behind her. "No roommate?"

"Funny, I'm not making that mistake twice," she winked at me. "You're going to have to put up with me."

"I like the sound of that," I said as we walked to the car.

"So, where is dinner?" she asked after we got in the car and adjusted our seat belts.

"Whitmire's."

"Really? How did you do that? They are booked up weeks in advance," she asked looking at me suspiciously.

"Turns out I have some connections," I smiled back at her.

We arrived at the restaurant and were seated at our table. "So, have you dated much since your divorce?" I asked.

"Does this count as a date?" she asked.

"Yes, I think it does," I replied.

"Then I have been on exactly one date since my divorce," she smiled back.

"You're telling me, the girl that had a date every weekend in high school, hasn't had a date in years?" I asked incredulously.

"It seems that I might have made a mistake in college by saying no to this guy and sticking him with my roommate and I lost him. So I'm a little more particular about who I say yes or no to. Just never met the right guy until today," she smiled at me.

We had a wonderful meal and a wonderful conversation. Time flew by and I looked around and realized we were the only ones left in the restaurant. The waiter came over and asked if we wanted refills on our drinks and I apologized for making him stay late.

"Kaye, wait, before we leave, can I ask you something?" I paused for her answer.

"Sure, what is it?" she asked.

"Will you go sailing with me?"

She looked a little surprised. "You have a sailboat? Sure, I can take a day off and go sailing. Where is your boat?" she asked.

"No. I want you to take a week or two or more and really sail with me," I said.

She looked a little stunned. "What size boat do you have?" she asked.

"50ft," I said a little sheepish.

"Never be embarrassed about things that you've earned. You sail it all by yourself?" she asked.

"I do, but now I think I can use a first mate. I'm just a little particular about who I ask. You're the first," I said.

"I don't know anything about sailing," she stated.

"Good! You won't have any bad sailing habits. I'll teach you everything you need to know. Part of the fun of being first mate is learning from a former classmate," I smiled at her.

She paused for a moment. "I think I have some vacation time. She paused again and then smiled. "Okay, I'm in. When are we leaving?"

"Tomorrow night," I stated.

"Tomorrow? I have a full shift and then I have to pack," she cried out.

"It's a boat, not a luxury resort hotel. It has a washer/dryer. Anything you don't have I'll get for you while we are on route," I smiled at her.

"Okay," she looked at me a little wary.

"I'm provisioning the boat tomorrow. Anything you want or can't eat or are allergic to?" I asked.

"I eat almost anything and I'm not allergic to anything that I know of," she replied.

"Beer, wine, rum, okay?" I asked.

"Yes, yes and yes," she smiled at me.

"I picked a good first mate. Fully qualified. I tell you what, I'll buy everything at your store. You can check me out and let me know if there are any problems or if I've missed something," I said.

We gathered our things, thanked the staff and left.

At 10:00 the next morning I entered the grocery store and 2 hours later I had $500 in provisions. Kaye sent me back into the store twice to get additional things I had forgotten. The manager didn't recognize me from the day before and was nice and closed Kaye's checkout line to allow me to checkout without anyone behind me. Two stock boys carried it out to the SUV.

I re-entered the store and whispered in Kaye's ear, "5:30, be ready."

Fully expecting to wait for Kaye to finish packing, the fully packed suitcase was at the door. Kaye gave her roommate some last minute instructions and we were off to the marina.

I pulled up in the guest space and a guy came up to me from the car rental to pickup the car. I signed the papers and grabbed Kaye's suitcase and headed for the docks. The boat was at the fuel pumps.

"It is all fueled, I topped off the water tanks and pumped the septic, sir," said the young attendant.

"Thank you. I'll be back in 3 weeks. Can you reserve a slip for me?" I asked of the attendant.

"Yes, sir. Would you like me to start the engine for you?" he replied.

"No I got it. Thanks again," I stepped on board and turned around and grabbed Kaye's hand and helped her on board.

Kaye stood there with her mouth open and just looked at the boat and the dozens of other boats in the slips around us. I started the engine and allowed it to warm up.

"Oh my god. I feel like I am a princess that has stepped into a different world," she said with disbelief.

"Well princess, most of the people here are just plain ordinary folk, typically really nice, down to earth people. Let me show you around the boat. It will take a few minuets for the engine to come up to temperature," I said.

I gave her the quick tour of the boat. When finished the engine had warmed up and I stepped off the boat and undid the bow and spring lines. The attendant singled up the stern line, I hopped back on board and he handed me the line. I pushed the gear into forward and gave it some throttle and the boat slowly slid forward and into the bay.

"It is going to take us about an hour to get out of the bay. My plan is to sail all night and get as close to Mackinaw as possible. Have you ever been to Mackinaw Island?" I asked.

"No," she looked at me.

"Okay, we need to fix that. I love Michigan but Mackinaw Island is the one place I hate the most. Everyone must experience it at least once, and then make up their own mind." I said.

"What's not to like?" she asked.

"Oh no. That is for you to determine. Maybe you'll like it, a lot of people do," I smiled at her.

I placed a call to the Mackinaw Island marina and reserved a slip for 2 nights. The wind was blowing out of the west about 5-10 knots and the forecast indicated it would hold for the next few days.

I unfurled the jib and the main and sheeted them out and allowed them to catch the wind behind us. I then shifted the engine into neutral and turned it off.

I motioned Kaye to the helm and gave her her first sailing lesson. We talked about jibing the boat, how to use the autopilot and a dozen other things. I knew from my time with her in high school she was going to be a quick learner and I was not disappointed.

I let her take the helm while I went below, turned on the lights and made supper. I returned about a half hour later with two bowls of stew. Kaye was smiling.

"This is awesome. I love it," she continued to grin.

"Well in about two minuets you are going to love it even more," I said.

We had cleared the bay and we were in Lake Huron. Time to set our course to the north.

"When I tell you, I want you to change course from 100 degrees to directly north. I'm going to sheet in the main sail and it is going to do a quick flip from one side of the boat to the other. You should never do this in high winds but tonight it should be fine. Okay, ready?" I asked.

"Ready any time you are captain," she smiled at me.

I hit the button on the electric winch and the main sail moved toward the center of the boat. It gave a slight thump as the wind caught it from the other side.

"Okay, bring it around," I ordered.

Kaye brought the boat around and I pressed the button on the other winch and sheeted in the jib. I also let out the main just a bit. The boat healed over slightly and picked up speed.

"This my dear Kaye, is sailing," I smiled at her.

She had her feet planted firmly on the deck, both hands on the wheel and her long blond hair flowing in the wind. "Well, I love sailing. Who knew," she said with a grin.

She was a sponge, asking all kinds of questions, learning all the controls and making sure she understood everything and how it worked. For three hours she was a whirlwind of questions and testing everything to figure it out. I thought she would stop after an hour but she kept diving deeper into the boats controls and systems. I kept thinking to myself, wow what an incredible person.

The plan was to sail all night. I would take the watch until 5 AM and Kaye would take it until noon. If there was any question, issue or concern she was to wake me up. Initially I was a little concerned about my plan but the past four hours convinced me Kaye could handle almost anything and most importantly she had good judgment and common sense.

At about 10:30 PM I turned on the auto-pilot and we settled down on the port side cockpit cushion. I could see the radar, AIS and I had a great view 360 degrees around the lake. I put my arm around Kaye and she nestled into my shoulder. About 10 minutes later she slumped over and I laid her head on my lap and lifted her legs onto the bench. She was now fast asleep on her side using my lap as a pillow.

I couldn't help stroking her hair and gaze down at the beautiful woman nestled in my lap. I was lost in her beauty and the thought of our upcoming adventure and how I might be the luckiest man in the world.

At 12:30 I needed to wake her. "Hey beautiful," I gently shook her, "I need to get up and make a slight course correction so we don't hit an ore carrier. You need to go below and get some sleep. Okay sweetheart?" I spoke gently.