Adventures of Sailing with Jennifer

Anthology of Sailing - Story 7: The Adventures of Sailing with Jennifer

My name is Tom, I live in a suburb just outside Detroit and last year I bought a sailboat, a 46 foot to be exact. I have been sailing for a long time and this was the boat I was looking to acquire for the past several years.

Sailing a boat like this can be a lot of fun and I have a couple of buddies that were more than willing to help out on the weekends. The idea was to get really familiar with the boat for a year and then take 6 weeks to do a big voyage and sail it from Detroit to Chicago and back again. Well, last year we learned the boat and now was the time for the big trip.

I had everything all planned, marinas contacted, created lists of supplies, arranged for time off from work and then the bad news happened. Bob had decided to change jobs and would be leaving for Arizona in 2 weeks. Jim decided he would get married and the new, soon to be wife, would not go along with the idea of Jim being gone for 6 weeks and she didn't want to go along as part of the crew.

I was stuck, I had a boat, plans, time off, arrangements made but no crew. I thought about canceling but I had too much time and effort put in at this point to give up. I also thought about going by myself, the boat is a dream to sail and many people have made that trip by themselves but safety is a big concern with me so I really wanted someone else along just in case there was an emergency.

I finally decided to place a personal ad in the nearby university newspaper, thinking there were plenty of able bodied guys at the university just looking for something to do during summer and a trip around the great lakes would be a good adventure. Interestingly, the only response to the ad I got was from a young lady by the name of Jennifer Walker who wanted to come out the next day and meet me and the boat.

Jennifer was a tall blue eyed blond who wore an over sized sweat shirt and sweat pants. She was very quiet and shy and didn't strike me as the type of person that would enjoy the wild open sea. Jennifer indicated that she was a graduate student in environmental biology and wanted a break from her thesis work. She had been looking for something that would be inexpensive and would allow her to get back to nature. She saw my ad and thought it would be perfect. She did have some sailing experience, her father had taught her as a child with a much smaller boat and she indicated she was looking forward to learning and working on a larger boat.

We talked a bit about the close quarters on a boat and the difference between us but she assured me that living with me for 6 weeks aboard the 46 foot boat would be no problem.

So a few days later Jennifer and I were off on our big adventure. The first thing that was obvious was she didn't have a lot of knowledge about sailing. She did know the difference between a line and a sheet and the main and jib but not much beyond that. However, she was a very fast learner and quite enthusiastic about the job of learning the boat.

We had light winds when we pulled out of my slip on Lake St. Clair and headed north for an easy crossing to Lake Huron. I took the opportunity to go over safety procedures with Jennifer and I was amazed at how quickly she picked up on everything. I even took the opportunity to do a couple of man overboard practices and after the third try she had it down and by fifth time I was confident that she could handle it in an emergency all by herself.

When we were done I had her furl the main and secure it and then showed her how to furl the jib. Once secured, I checked the GPS and I let her take the helm as we motored through the St. Clair River to Port Huron. She did a great job, I showed her how to read the depth meter, how to look at the channel and note shallow spots, what the marker buoys meant and the infamous red, right, return for channel navigation into and out of a port.

We made good progress through the river and found lake Huron clear and smooth. The sails went back up and we silently slipped through the water. Talking to Jennifer was interesting, she wasn't much into small talk but when we were talking about technical issues about the boat or the science of sailing she was all ears and asked great questions. Also, when her mind was challenged she perked up. I snapped off a couple of puns and she retaliated with a couple more, we went back and forth until I had no more. She was clearly having fun.

When it started to get dark we found a nice cozy spot and dropped anchor for the evening. We had dinner and I even opened a bottle of wine to celebrate our pending adventure. We were both tired from the days activity and I showed her the uniqueness of her berth and I headed to the V berth at the bow of the boat.

By 6:00 the next morning we were up and raising the anchor. We got the boat underway and Jennifer headed to the galley to make us some breakfast. She returned about 20 minutes later carrying 2 plates of scrambled eggs, toast and bacon. I had it on autopilot and was sitting on the port bench. She sat next to me wearing the ubiquitous sweats and wrapped in a blanket, facing away from the wind, eating in silence.

"You're not a morning person," I said breaking the silence.

"No, I don't function very well with out breakfast and a shower. Speaking of shower how does one shower on a boat?" she asked.

"Well there are 3 ways to wash," I replied. "You can simply dive into the lake, very cold especially early in the season. You can use the shower below, it is cold, cramped, slippery but it is private. Or you can use the solar shower any time after about 10:00. It is a bit public but very warm and refreshing - I use it when ever we have bright sunny skies."

"Well if it is all the same, the lake is calm and I only see one boat anywhere on the lake. I think I will go below and try the shower," she replied.

With that she gathered the plates and went below to take her shower.

About 10 minutes later I saw some large waves coming toward us that must have come from the ore carrier that went by. I hollered out waves coming in but Jennifer didn't hear because when the boat went up on the first wave I heard a scream, a very loud bang and a groan.

I threw on the autopilot and raced for the shower. I heard nothing except the water running. I opened the door, turned off the water and saw Jennifer laid out on the floor completely naked and not moving.

"Jennifer, are you okay?" I cried out waiting for a reply.

"I think so," she moaned as she opened her eyes and gave me a feeble smile.

"Help me up," she feebly extended her hand.

"No you don't, I haven't lost a first mate yet and I'm not going to today. We are going to do this by the book. Move your toes, now all 10 fingers, now right leg, now left leg." I voiced each command which she successfully completed.

It was only at this point that I began to relax and noticed the amazingly beautiful woman laying on the floor of my shower. She was about 115 pounds and had large firm tits. Her legs were long and thin and looked like those of a model. She was also a real blond.

I reached around behind her and pulled her up as she wrapped her arms around my neck. I held her close as I waited for her to unwrap her arms and stand on her own. As soon as she stood back I averted my eyes and grabbed a towel and handed it to her.

"So where does it hurt?" I inquired.

"Nowhere," she lied.

"I heard a loud bang. You hit something," I replied.

"It was nothing."

"Jennifer, I heard it in the cockpit. It was a loud bang."

She paused for a moment, "okay, okay, my butt if you must know," turning an amazing shade of red.

"Let me see," I directed, trying desperately to keep a straight face and not break into laughter.

"You're not serious?" she replied.

"Someone should check you for injuries and I don't see anyone else here," I said looking around.

"Okay," she agreed reluctantly. "I guess you have seen everything else I have."

I moved around to her backside and lifted the towel she was now wearing. "OH WOW!" I exclaimed.

"I hope that was a comment about my injuries and not my butt?" now seeing the humor of the situation.

Both cheeks were flaming red. I moved my hand to her tail bone and pressed lightly. "Does this hurt?" I questioned.

"No. What are you doing back there?" clearly getting her energy back.

I pushed on her hips lightly which got no response so I lowered the towel and returned to face Jennifer.

"Despite the red cheeks, which are going to hurt for a couple of days, the butt checks out A-okay," I smiled.

"Thanks," she replied sheepishly.

"Your welcome." I gave her a hug. "You scared the hell out of me - please be careful in the shower."

I returned to the cockpit, grabbed the wheel and disengaged the autopilot. Jennifer returned in about a half an hour dressed in sweats carrying a bag of ice.

She sat the bag on the cushion and then sat on the bag.

"Jennifer," I said, "you could sit directly on the ice. It would be better for you and you would keep your clothes dry. I promise I won't gawk, stare, leer or otherwise be a pervert."

"I know you won't, it is just so embarrassing," She commented.

"There is nothing to be embarrassed about. You have an injury and you are doing the right thing by putting ice on it," I replied.

With that she lowered her pants and underwear, sat on the ice and gave a big sigh.

We sailed on for several hours under light winds and fair skies. Finally I decided it was time for Jennifer to take the wheel while I got cleaned up.

"You feeling well enough to take the wheel while I clean up?" I asked.

"Yes captain," she replied with a smile and with that she rose, pulled up her pants and took the wheel.

I went below shaved and brushed my teeth. When finished I grabbed a towel and headed back to the cockpit to use the solar shower. I checked the temperature of the black bag of water and then used the wash off hose to add a little cold water. You can actually burn yourself if you let the water get too hot.

"If you're squeamish about nudity you can put it on autopilot and go below," I said with a smile but I got no reaction from Jennifer.

I adjusted the bag and removed my shirt, shorts and underwear. I then adjusted the hose, removed the clamp and wet myself with fresh warm water.

"My god, you're naked," Jennifer exclaimed from behind me.

I turned and faced her. "I believe it is customary and practical to take showers that way."

She never did look me in the eye as I reached for the soap and began lathering my body. I rinsed, then grabbed the towel, walked over to the the compass and remarked, "I think you might be a bit off course."

Jennifer turned beet red and exclaimed in frustration, "you make it hard to concentrate with your thing all dangling there," as she spun the wheel and brought us back on course.

"Oh, Sorry about the dangley thing. We've been together for a long time, we're kind of attached," I smiled. With that I grabbed my clothes and headed below.

The rest of the day went well. It was apparent that Jennifer was feeling some pain as she tried hatching several ice packs. We again found a nice anchorage for the evening and had a nice supper.

Just before we went to bed Jennifer came up to me, gave me a hug and whispered. "Thank you for rescuing me in the shower this morning and taking care of me this afternoon," and with that she kissed me on the cheek and went to her quarters.

The next morning the same scene unraveled. Jennifer came out carrying two plates of breakfast and then sat quietly wrapped in a blanket.

"How are you feeling this morning?" I inquired.

"A bit sore. Would you take a look at it and see how it is doing?" she looked at me.

"Oh god yes," I smiled.

"You're actually enjoying this aren't you," she scolded me.

"I wasn't yesterday, but I know you are going to be okay and I just can't resist seeing a little humor in it," I replied.

"Okay, I guess it is a little funny," she smiled. "It will probably be the story that we laugh about for the next 20 years," now breaking into a grin and laughing.

She stood up, dropped her sweat pants and bent over slightly. "No funny business back there, just look."

"Hey, I take my butt examinations very seriously... Whoa!" I exclaimed.

"What? What is it?" she cried.

"Well, except for two serious black and blue marks, that is one sexy tushy," I smiled.

"Would you get serious for a minute and tell me what is going on back there" she quipped.

"Unless you want me to feel around for knots or other things, black and blue is all I see," I replied.

"Okay, touch, but be gentile," she instructed.

I felt everywhere and I mean everywhere, it all felt like it should. I grabbed the first aid kit and got some lotion and gently rubbed it into the bruised areas.

"Oh wow that feels wonderful," she moaned. "what is that?"

"It is a topical anesthetic." I replied.

I pulled her sweats up and she returned to her seat, this time with a bit of glow in her eye.

"I am ready to do some sailing," she said... getting up and pushing me away from the wheel.

I wandered over an adjusted some of the lines and then took the solar shower down and filled it with water to make it ready for my mid-morning shower. The weather was perfect, the sky was clear and the winds were blowing from the west around 5 knots.

Jennifer sailed the boat for several hours and I finally decided it was time to take a shower. This time I went below and left my clothes in my cabin and brought up only a towel. I wet myself with the hose, lathered up and had began to rinse off.

"Can I use the solar shower?" Jennifer meekly asked from the wheel.

"Sure, I'll be done in a minute." I replied, turning around and facing her for the first time.

"No, I want you with me when I do, in case something happens," she explained

"Uh..., ya..., uh sure... Flip on the autopilot and come join me," I stammered.

She flipped on the autopilot and removed her top and pants. God was she beautiful. She walked over to the shower and held onto my arm. She held onto the boom vang and I gently sprayed water onto her everywhere, then I took the soap and scrubbed everywhere. When I got to her nipples I couldn't resist pinching and rolling them in my fingers. They rose to attention and Jennifer let out a little moan. I then rinsed her off. When finished she gave me a close hug and kissed me on the cheek. It was then that I realized I was packing some serious wood and it was sticking into her stomach. Jennifer noticed it also and let go and looked down.

"Whoa, It's that dangley thing again. It doesn't look normal - it's all swollen," she teased.

"Someone should check it for injuries, you're the only one around," I replied.

"Unless you want me to feel around for knots or other things, pink and a purple head is all I see."

"Okay, touch but be gentile," I smiled.

She tweaked it with her index finger, looked me in the eye and said, "if the shower had been colder you wouldn't be having this problem." She smiled, grabbed her towel, clothes and headed for her berth.

Oh, that was cold, I thought as I stood there stunned. I wasn't sure exactly what to think. I toweled myself dry, put on my clothes and released the autopilot and took the wheel.

A little while later Jennifer came up from below and sat on the bench near where I was standing. She sat quietly for several minutes before Jennifer spoke.

"I just want you to know I am really sorry about what just happened a few minutes ago. I didn't mean to be cruel or insensitive to your needs. I'm not like that, I'm really not. I just got caught up in the moment and the playfulness. I'm just not ready for that type of relationship in my life right now and not after 1 day on a boat. Are you okay?"

"Sure," I replied, "I guess I was a little stunned. Look, I wasn't expecting anything. I do want to be completely honest with you, however. You are drop dead gorgeous, you're very smart, have a great personality and frankly I find you very, very desirable. I'm sorry I let my feelings show - if you know what I mean."

"I understand, it's not something a guy easily controls. I'll forgive you, if you forgive me."

"It's a deal," I said. "Are we friends again?"

"We certainly are. Real friends are honest with each other and talk about and work through their problems. I think we have a good friendship ahead of us," Jennifer smiled up at me.

"Well friend, take the wheel, I have a couple of chores to do." With that Jennifer got up and pushed me out of the way.

"Hey friend, does this mean I can keep checking out your butt?" I smiled and twisted around to check out Jennifer's completely covered back end.

"Oh, in your dreams mister. I am hereby revoking all butt viewing privileges." She smiled and stuck her tongue out at me. "I thought you had chores to do, instead of standing around ogling at the first mate." We both laughed.

I spent the rest of the morning and afternoon doing various odds and ends on the boat allowing Jennifer to handle the navigation and the wheel. I also found a chunk of old plastic sheeting and constructed a shower curtain for the solar shower. I also did some fancy rope work and constructed a hand hold for anyone using it who might need something quick to grab onto.

Around supper time the winds came up hard and I quickly checked the charts and headed for the nearest cove that looked like it would provide safe harbor. Turns out it was perfect, the wind was landward and despite the wind the water in the harbor was calm. We quickly set the anchor, had supper and turned in early for the night.

The next morning the winds were still blowing strong. Jennifer did her usual wrapped in a blanket appearance and sat quietly next to me as I studied the charts.

"Jennifer, it could be a rough ride today, have you ever been seasick?" I inquired.

"No," she replied looking up from her coffee.

"I have some seasick pills. Do you want to take one?" I inquired.

"No," came the same reply.

"Okay, but if you start feeling queasy, let me know right away. We need to get one in you before you start throwing up," I said.

"I'll be fine," she replied.

We stayed in the harbor a couple of hours longer than we usually would and despite the wind the sun was shinning and I wanted to get my shower before a day that was sure to be long and hard. When the shower was warm I took my shower and Jennifer followed using the curtain I had rigged up the day before. When she was done she wrapped a towel around her and headed below to her berth. When she leaned over to go down the stairs, the towel opened up in the back.

"Wow, nice butt. Oh, sorry about looking," I shouted out.

When she got down the steps she turned around and looked at me. "A friend wouldn't have considered it necessary to make a comment," she smiled and pouted.

"Just being an honest and open, friend," I replied.

"Yes, well perhaps to a fault," she muttered.

When she returned we pulled up the anchor, headed out of the cove and set the sails. Within 10 minutes we were being pounded by waves, they were breaking over the bow and splashing us in the cockpit. I looked over at Jennifer and she was standing forward in the cockpit, looking at the bow and smiling. She was completely wet. For some reason she wasn't wearing the usual sweats but instead a T-shirt, shorts and no bra. She looked great.

I had the main and jib only partly unfurled and the boat was sailing like a champ. It was handling great and seemed to be well balanced. We were cutting through the waves like a knife.

Jennifer went below and about 10 minutes later returned with a strange expression on her face. She ran quickly to the side of the boat, leaned over the gunwale and then I heard it, "bleeeeck." I flipped on the autopilot and ran to her side. There she was vomiting out breakfast.