Sailing with Samantha

Anthology of Sailing - Story 6: Sailing with Samantha

I would never have been in this weather if it hadn't been for my brother, Bob. There was a big age difference between us but we always got along, even as children and now as adults. He was a bit unusual but a really nice guy. He waited until later in life to get married and his wife Maryland, was gorgeous. She had 3 daughters from a previous marriage and Bob became an instant husband and father. The girls: Amy 14, Molly 16 and Samantha was 19.

It had been a long sail from Chicago and the forecast was for light showers but not something that Sapphire couldn't handle. I had purchased Sapphire 2 years ago. I had a fair amount of sailing with it in the past 2 years but it was all mostly fair weather, picking the days I would sail fairly carefully. I would occasionally go out in a mild thunderstorm, just to get some heavy weather sailing experience but I always leaned toward caution and never put myself or the boat in harms way.

I spent the summers sailing the boat around the great lakes. As a university assistant professor, I get a lot of time off during the summer and decided the best way to relax is out on a boat all by myself, catch up on the latest technical literature, shoot some photos, listen to some music and write research papers. Living on the great lakes gives me fairly easy access to Chicago, Detroit and hundreds of small towns along the shores of Lake Michigan, Huron and Superior.

I had sailed into Milwaukee to visit my brother, at his request. I really didn't know Maryland and her daughters very well, other than meeting everyone at the wedding and what Bob had been texting me, so this was a chance to get to know everyone.

"Hey bro, how are you doing? How's married life?" I asked giving him a giant bear hug. "Give your younger brother the good and the bad."

"Well, after the wedding Maryland became an animal. Whenever the kids are away or when they go to bed Maryland wants to fuck. She has the same sex drive I do - always on. Even when she's feeling un-sexy, she'll just grab me, get on her knees and blow me. My cock has never been happier," Bob replied.

"So what is the good," I smiled at Bob.

"Funny, you asshole," Bob glared at me. "The bad is really bad. Maryland and Sam fight all the time. They can't be in the same room together. Life in the house when Sam is there is a holy hell. Worse, I've turned into the referee. I swear someday someone is going to get hurt. Sam is so angry with the world, she lashes out at Maryland because she married me and her friends went off to college, her real dad treats her like crap - she is a mess. I have to separate the two."

Bob paused for a minute. "So, you are headed north for a few weeks and then back to Chicago?" he asked.

"Yup, that is the plan," I replied.

"Would you do me a huge favor and take a passenger? Look, I've got to separate those two." I could see desperation in Bob's eyes.

I thought for a second. "Hell yes, I'll take Maryland. It is damn decent of you to finally think about your brother for a change," I smiled at him.

"Fuck you! I'm talking about Samantha you moron." He shook his head.

"No! No fucking way. She's a bitch, She's toxic. She should be in a mental ward getting help, not on my boat," I swore at Bob.

"She's really cute," Bob replied.

"So is a puma but I wouldn't put one on my boat with me for 3 weeks," I shot back.

Bob looked down and I thought he might cry. "Bro, I really need this. I don't know who to turn to. I'm desperate - it's going to destroy my marriage. I've got to have help with this and you're family. I've never asked you for anything - please help me," he begged.

I put my arm around him. "Okay, okay, I'm there for you. I'll do it but I've got a couple of rules, No drugs, no alcohol and no cigarettes. Maryland needs to strip search her before she gets on my boat. I don't need to be dealing with chemically induced behavior along with her normal behavior.

Bob grabbed me and gave me a hug. "You are the worlds best brother. I love you bro."

"Well you owe me big time for this," I hugged him back.

"We don't really know about the drugs but fairly certain she hasn't been doing alcohol or cigarettes," Bob commented.

There was a lot of screaming at Bob's house that evening despite the fact I was there. Maryland came up to me and gave me several hugs and even kissed me on the cheek once, for being the best brother-in-law.

The departure in the morning was carefully choreographed. I arrived at the boat with Bob about 20 minutes before Maryland and the girls. Bob helped me get the boat ready and then waited for Maryland to arrive at the parking lot. Bob grabbed Sam's luggage and they all walked to the boat.

I helped her on board and then closed the lifeline so she could not easily leave. I moved the boat about 10 feet out of the slip and stopped. It was at this point Sam realized her luggage was still on the dock. She started screaming when she saw her mother zip open the bag and start removing the contents.

Out came bras, panties, shorts, tops, shoes, cigarettes, pint of whiskey and a zip lock bag full of pills. Maryland calmly put the clothes and shoes back in the bag and zipped it back up leaving the remaining contents on the dock. Sam want ape-shit, screaming every swear word she knew at her mother at the top of her voice. We were attracting a lot of onlookers as boaters poked their head out to see what all the commotion was about.

Bob grabbed the bag with just the clothes and shoes and ran it down to the end of the dock. I put the boat in reverse and Bob gave the bag a huge heave and it landed in the cockpit. I shoved the boat into forward and we headed out of the harbor.

Sam went berserk. She continued to scream and swear at her mother and Bob. She stomped her feet and made hand gestures at them as we motored away. She finally broke down and began to cry.

"Why did they have to take the only things in life that I really enjoy?" she sobbed.

I waited a minute. "Because I asked them to," I replied to her question.

She sat up. "You! You mother fucking son-of-a-bitch. God damn fucker! Why do you hate me?"

I paused, "I don't. I actually like you. I want you to grow up and be smart, caring and a contributing member of society."

She gave me a scored look. "Well that is not what I want. I'm an adult. I should get what I want."

"Life has so much to offer. Yes, there is pain but dulling the pain with drugs and alcohol also dulls the joy in life. The joy overwhelms any pain we have in life. The joy of falling in love, accomplishment, creating something, watching new life and yes even sailing a boat," I smiled at her.

"Fuck you! Sailing is bullshit. This whole thing you are doing to me is bullshit," she lashed back at me.

There was about 5 minutes of silence. Then I asked, "how badly are you addicted to the booze, cigarettes and pills?"

"What the fuck are you talking about? I'm not addicted, you fucking moron," she lashed back.

"Good," I smiled back at her. "Tomorrow should be a good day then. There are 2 empty cabins at the stern of boat. Go ahead and pick which ever one you want. There is also a head, back there. That one is all yours, I have another one in the master cabin."

She gave me a look and then grabbed her bag and went below.

I unfurled the sails, shut the engine off and headed the boat north. I trimmed the sails and then set the autopilot. I did some clean up work and then checked the AIS, radar and other systems to make sure they were working.

I did a quick check for traffic and then went down below and the aft port cabin door was closed. It was almost lunch time so I made two sandwiches. I put them both on plates. I knocked on Sam's cabin door. "Lunch is on the table, if you are hungry."

"Fuck off, asshole!" came the reply from the other side of the door.

"Okay, fucking off," I said quietly to myself. I grabbed my sandwich and headed for the cockpit.

I had several things I needed to do on the boat so the afternoon was filled with sailing and chores. When supper time came, the uneaten sandwich was still on the table. I heated a pot of stew for 2. I filled a bowl and headed for Sam's cabin and knocked on the door.

"Hey, I have some wonderful stew. Time to eat," I said but I got no reply from the other side of the door.

I opened the door and Sam was curled up in a ball, shaking slightly. I sat on the edge of the bed and brushed her hair lightly with my hand.

"What's up Sam? You feeling okay?" I asked.

"Oh sure," she said but it was obvious she was lying.

"Do you think I'm pretty?" she asked.

"Oh, of course you are. You are pretty on the outside but beautiful on the inside also," I answered and continued to brush her hair.

"Do you like my tits?" she asked.

I paused in shock. "Okay, what is this all about?" I asked.

She looked up at me with those sweet blue eyes. "If you give me a beer, I'll let you fuck me."

"Okay, sit up. You haven't had a thing to eat all day. Time for stew," I said, grabbing her and sitting her up in the bed. I reached for the bowl of stew and dipped the spoon into it and held it to her lips. She looked at it for a second and opened her mouth. I pushed the spoon in and dumped the contents.

"Mmmm, that's good. Did you make this?" she asked.

"Yes, its my grandmothers recipe," I replied.

"Yum, it is delicious. I don't remember Bob talking about your grandmother, what was her name?" she asked.

"Uh... Dinty. Come on now, less talk and more chew," I said as I shoveled another spoonful into her mouth.

She finished the bowl, spoonful by spoonful, and a large glass of water. I let her snuggle against me for a couple of minutes and it was apparent that she was feeling better. I grabbed a bucket and a towel and placed them on the floor next to her bed.

"Feeling better, sweetheart?" I asked kissing her lightly on the forehead. "Things might get a little rough for the next couple of days. I'm here for you. We'll get through this together, I promise." I kissed her again on the forehead.

The next 3 days were horrible. She was vomiting, had diarrhea and constant shakes. I brought her up to the cockpit so I could constantly keep an eye on her, while I sailed the boat. It was warm and I gave up trying to keep her in clean clothes. I fashioned a towel diaper with duct tape and kept her bra on her. I cleaned her skin with a washcloth and then draped towels over her because I knew I would be changing them in an hour or two.

I laid down with her and she grabbed me and the shaking stopped. It was the only relief I could give her except for some over the counter pain medicine. She would fling the towels off her, open her arms and just mumble please, please until I laid down and wrapped my arms around her. I had to stop every 30 minutes and get up and check for traffic.

The evening of day 3 it looked like we had turned a corner. That following morning she got up from the cockpit cushion, where she had been lying, threw the towels off her, and walked bottomless down to her cabin. I checked on her about 15 minutes later and she was fast asleep in her bed. I draped a sheet over her.

About 3 hours later I heard some noise and her shower was running. About 30 minutes later, Sam stuck her head up from the saloon and looked into the cockpit. She was freshly showered and her long blonde hair was washed and perfectly combed.

"Wow, that is the prettiest smile I have ever seen," I said.

Her smile got even bigger. "I have a bit of a problem. My clothes are all soiled and the only thing I found to wear was your button down shirt hanging in my closet." She slowly climbed the stairs and revealed her outfit.

"Holy shit!" I exclaimed as my mouth dropped open. The shirt was way to big and the sleeves were way to long and Sam had rolled them up. The material was slightly transparent and the sun streaming into the cockpit showed the perfect naked form of the woman standing in front of me. She was absolutely beautiful. Her perfect C tits had just a hint of sag but her thin waste accentuated them even more. Her skin was flawless and her cheeks had just a tint of rosy red. She was a goddess.

"You like?" Sam smiled and turned a slight shade of red.

"It never looked that good on me," I smiled and raised my eyebrows.

"Can I keep it?" she asked.

"Ahh, sure. Oh god, don't let your mom or dad see you wear it like that. They'll kill me," I panicked.

"Deal," she said and came over and wrapped her arms around me. "Thank you for taking care of me. I feel good."

I wrapped my arms around Sam and rubbed her back, waist and lower regions, "Yes you do," I said.

I heard a slight giggle and realized I had said it out loud. "Oh, I'm so sorry," I whispered in her ear.

"Don't be. A girl has feelings on the inside and the outside. It's good to know a guy can admire both," she whispered back.

We held each other and hugged a lot longer than we probably should have. She rubbed her hands around my back, waist and lower. I knew she didn't have any panties on under the shirt and I stopped at the bottom of the shirt. Four days ago she told me I could fuck her for a beer. She wasn't just vulnerable, she was fragile and any mis-step in my direction could push her back into drugs and alcohol.

I released her and gave her a kiss on the forehead. "Hey, how would you like a crash course on sailing a boat?"

"Sure, what's the hurry," she smiled at me.

"Nothing. You seem to be feeling better and I could really use a nap," I smiled back at her.

"Oh, ya. Between sailing the boat and taking care of me..." she trailed off her words and looked down at the deck.

"Hey, worth every minute of it." I took her hand and squeezed it.

I showed her how to steer the boat, what our course was, how to set the autopilot, read the AIS and the radar. She promised to wake me if she had a question or problem. I went downstairs, set my alarm for 3 hours and fell into my bed. The next thing I remember my alarm was going off.

I staggered out of bed and grabbed a drink of water. I looked out and above the stairway into the cockpit and Sam was at the wheel and smiling and humming a tune. She was barefoot with both feet planted firmly on the deck. The wind was lightly blowing her blond hair behind her and it was also blowing the transparent shirt, revealing her legs and hips. She was beautiful. Sam had a bunch of dirty towels piled up in the center of the cockpit and a bucket of water where it looked like she had been rinsing them out.

I saw her put the boat on autopilot and then walk over to the pile of towels with her back toward me. She then bent over the towels. Her shirt rode up her back and there it was.

"Oh my god," I moaned.

Sam quickly stood up and turned around. "Oh I'm so sorry. I didn't realize you were awake," she said as I quickly climbed the stairs.

Then she got this impish look and stared directly at my crotch. "So is that morning wood or did you really like what you saw?

My face turned instantly red but she handled it wonderfully. She put her arms around me and gave me a hug. She whispered in my ear. "Some women are flattered when a man complements her not just on how she feels but also on her looks. Thank you"

Again we hugged a lot longer than the typical hug. This time she stood on her toes so she could whisper in my ear and the shirt rode up over her butt. My fingers reached over the edge of the material and pressed into her fleshy ass.

I spent the rest of the day teaching Sam about sailing. She was a sponge, learning everything she could and asking amazing, intelligent questions. She learned in 4 hours what a normal person would learn in 2 weeks.

"Okay smarty, let me ask you a question. The apparent angle of the wind is 30 degrees and the apparent wind speed is 12 knots and the boat is moving at 6 knots. Then what is the..."

"The true wind speed is 7.4 knots at an angle of 51.8 degrees," she smiled at me.

I was stunned and looked over at the chart plotter - she was right. "How did you do that?" I questioned.

"Well, when you think about the angles and the speeds, the answer is kind of obvious. Isn't it?" she asked.

A little shocked. "Not to me," I replied.

I pulled out my phone with a calculator and gave her 5 more questions which she answered perfectly and within a second each. "Oh my god, Samantha you're amazing. Does anyone else know you can do this?" I asked.

Sam looked down. "No, I didn't want anyone calling me a nerd or geek. Girls aren't suppose to be good in math."

I came over and gave Sam a hug and brushed her hair out of her eyes. I looked her in the eyes. "Sam, you have a gift that I don't have, most people don't have. Only a very tiny fraction of people can do what you just did. The person that told you that girls weren't suppose to be good in math, fed you a pile of horseshit. It is wonderful when girls are good in math. I wish more girls would study math - it would make the world a better place."

We got that weird look that a man and a woman get just before they are about to kiss. I realized this was not what Sam needed right now so I pulled her closer and put her head on my shoulder. We stayed that way just enjoying each others warmth.

"Can we talk?" Sam broke the silence and I broke the hug and pointed to the port cockpit bench.

I sat next to Sam. "Do you have a girlfriend?" she asked looking out over the water.

"No," I replied.

"Why not?" she asked and continued to look out over the water.

"I don't really know. I like women that I have things in common with. I like women that are just as smart or smarter than I am. I'm not really into sports but I think a lot of women are because guys are. Women sometimes intimidate me. Especially the beautiful ones. I don't understand how they would go out with someone ugly like me."

"You are not ugly!" Sam instantly snapped. "I think you are very handsome." She paused. "Do I intimidate you?" she asked.

I turned and looked at her. "You are one of the most beautiful women I know but the rule states that you can not be intimidated by a women that vomits on you. So no. The rules say I can not be intimidated. I don't make these things up." I smiled at her.

She turned and finally looked at me with a big smile. "Yes you did - you made that up! Did I really vomit on you?"

"Yes, I was wearing that shirt you're wearing now," I tried to look sincere.

She looked down at her shirt and I started to laugh.

"Look," I started to speak, "I'm a really direct guy. Tell me if I'm right. Are you trying to figure out if you are girlfriend material?"

"You really are smart. Yes, something like that," she shyly looked at me.

"Sam I really like you and I could see us as girlfriend/boyfriend but we have some other people involved in this and that is your mother and my brother. I don't think the age thing is a big deal but your mom might," I said.

"Oh ya, mom. I have a lot of apologizing to do to her, don't I?" she winced.

"Nope, I am an authority on apologizing to moms. It is really simple. When we get back to port, the second you step onto the dock, you run as fast as you can to your mother and give her the biggest hug you have ever given to anyone. Then whisper in her ear, 'I'm sorry.' Guaranteed she will be crying like a baby. Stay off the booze, drugs, cigarettes and help with chores around the house and you are golden."

"Well I ain't ever doing any of that shit again. I was pretty fucked up wasn't I?"

"It's not important where we have been but it is important where we are heading now," I smiled at Sam.

"Speaking of the future. Tell me about college. Was it a lot of parties like they show in the movies?" she asked.

"Nope, not for me. It was a lot of work - class, studying and homework. There was never time for parties. I worked my ass off," I replied.