Sailing with a Beautiful Model

Anthology of Sailing - Story 3: Sailing with a Beautiful Model

I was going to merge my two favorite things, sailing and photography by splurging a little and hire a model for the day. I had seen Kristy's bio in one of the modeling websites and she listed as a special skill, sailing.

I don't typically hire models unless there is a customer that wants something specific photographed with a model and I typically pass the costs of the model back to the customer. This was different however, I didn't have a customer that wanted photos but thought it might be fun to spend the day sailing and taking pictures on my boat.

I bought the boat, a new 54 foot sailboat, two years ago and have taken plenty of photos of it. However, I have not had a beautiful model on it and taken photos. There is something about a beautiful girl and a boat that seems to bring out the beauty of the boat, water and surrounding area. I was hoping it would be a nice day for sailing and I was looking forward to meeting Kristy.

I have always sailed the boat by myself, except when I have guests on for the day or perhaps a couple of days. Most sailboats require a couple of people to sail but the boat I purchased was specifically designed to be sailed single handed. With the electric winches and all the sheets right there at the helm station, it is simple to handle all by myself. Docking is sometimes tricky but the guy in the next slip to mine is real good about giving me a hand whenever he sees me pull in. A little planning in other areas and I manage pretty well most of the time.

I sent Kristy an e-mail and she called me back with some questions. She seemed really nervous about the job and I guess I don't blame her. Models can be easy prey for a crazy person that wants to take advantage of a pretty girl in a remote and secluded location. She seemed very uneasy about getting on a sailboat with me alone. She asked me for someone she could call and get a reference and was looking for someone she might already know.

The first person I named was Tom Franklin and she immediately said she knew him and had done a couple of shoots with him. She said she would call me back to set up a time.

I had known Tom for a really long time. He is a bit of a practical joker but we are really good friends. About two hours after talking to Kristy, Tom called.

"Hey, asshole. Someone by the name of Kristy called me and wanted a reference on you," Tom said.

"Ya. I'm trying to get her on my boat to take some pictures but she seemed nervous about the job," I replied.

"Well, I can't say I blame her. You already sound like a pervert over the phone. I told her you would probably rub up against her a lot but only expose yourself once or twice," he said with a sincere voice. "But then I told her that your junk is so small that she probably wouldn't even notice."

"Well, I can always rely on my friends to have my back when I need it," I said incredulously.

"I'm there for you dude. Hey, you are going to enjoy working with Kristy. She is a doll. One of the best models I have ever worked with. You have a customer that wants this or are you doing this for fun or you finally going to pay some girl just to get on your boat with you?" he asked, clearly enjoying this.

"Just going to take pictures of the boat for my portfolio," I said, trying to answer the question and then realizing he didn't really want an answer.

Just then my phone buzzed. "Hey, gotta run. Thanks for the reference - I think. Bye."

"All day with just Kristy and your sailboat. Lucky fucker. Bye," Tom said.

I pushed the talk button on my phone. "Hello this is Jim," I said.

"Hi Jim. This is Kristy Kowalski, the model you contacted about working on your sailboat."

"Hi Kristy. How are you?" I asked.

"Just fine. Look, I contacted Tom Franklin and if the job is still available I'm definitely interested." I could hear for the first time some excitement in her voice.

"So Kristy, I have to ask this. How much sailing experience do you have? There will just be the two of us. I might need you at the helm while I'm setting up and getting things ready. I realize that is not standard modeling duties but hope you wouldn't mind, if you have the expertise," I inquired.

"Mind? I would love it! I've been sailing since I was 5 when my father put me in a little Sun Fish sailboat. My family has a 22 foot Catalina which I sail all the time. This is an opportunity to merge my two favorite things sailing and modeling," she said, clearly excited about the planned activities.

"Wow, that is great. I think this is going to work out wonderfully. My boat is a little bigger than the Catalina but except for some fancy equipment, the principles are all the same," I said. Now understanding what a great fit this could be and it could be a good day of sailing and photography.

We agreed on a date next Tuesday and agreed on a price for Kristy's time. She recommended some things that she could bring and wear and then asked about makeup.

"None, nope, no makeup. The only thing I want you to wear is sunscreen. Just sunscreen," I said and the phone went silent. I suddenly realized what I had said and corrected myself. "With your clothes. Sunscreen with your clothes."

"Oh, of course. Sunscreen with my clothes," Kristy acknowledged.

We both hung up our phones looking forward to next Tuesday.

Tuesday morning arrived and I took the opportunity to tidy the boat and make it perfect for the days photo activity. At precisely 9:00 Kristy came walking up the dock to the boat. I'm not sure who took her pictures in her portfolio but they did not do her justice. She is beautiful in her pictures but in person, wow. I was stunned by her beauty.

I introduced myself and grabbed her bag and then offered a hand to help her on the boat. She took it but didn't really need it as she hopped onboard, well accustom to getting on a sailboat. I handed her a model release form, she scanned it, signed it and then looked around the boat.

"Oh wow! You have electric winches and a furling main sail and everything is running back here to the helm so you can single hand the boat!" She was like a kid in a toy store for the first time. Examining all the wonders and cool things that were on the boat. She turned and faced me.

"It is the prettiest thing I have ever seen." she said

"Kristy, you are shaking." I commented a little surprised.

"Sorry. I've seen a lot of boats and there is something special about one that is perfect - she's amazing. Can I touch her?" She asked excitedly reaching for the wheel.

"Yes, of course. In a little while I'll have you at the helm. However, first we are going to have a safety briefing and then I'll show you around the boat. After that we can talk about the shooting plan while heading out of the harbor. Okay?" I asked.

"Sounds good," she smiled at me.

I put her bag down below and while down there she asked me to grab her phone. When I returned I handed her the phone and she put it in the nearest cup holder.

"The first point of safety is to not get fingers, hands or arms between the boat and a firm object. You can not fend off this boat like you can a 22 foot Catalina. The only way to stop the boat is with the engines or a line and a cleat," I said.

"Oh, good point. I guess a boat this size can not be pushed around," she said, now understanding the purpose of the safety briefing.

"Second, life vests to be worn at all times the boat is underway and you are up on deck. The exception today is while taking a photo. The last thing you need to do before I shoot is take off the vest and the first thing after is to put it back on. The vests are actually really nice and we'll probably do some shooting with them on. The vests are in that hatch - help yourself," I said pointing to the nearest hatch.

Kristy walked over and opened the hatch. "Oh wow. These are awesome."

"Yup, Coast Guard approved, self inflating. Why wear something that is bulky, uncomfortable and not stylish," I smiled at her.

I showed Kristy the rest of the boat, helm control and other things that I thought she might need to know. I started the engine, uncleated the lines and slowly backed it out of the slip. Kristy watched with great interest and asked the occasional question as we pulled out of the marina.

We started talking about the days shoot and while we did I stepped back and let Kristy take the helm. She gave me a kiss on the cheek and took the helm and she was just beaming. I grabbed my camera and began shooting photos. She took us out into the harbor and into deeper water.

I stood next to Kristy and asked her to bring us into the wind. I then pressed a button and the winch nearest me began spinning and main sail began to unfurl. I stepped over to the port helm and hit a button. The jib unfurled and began flapping in the wind. I pulled on the jib sheet and motioned for Kristy to turn us to port, which she did.

"So do you remember how to set the engine to neutral and turn it off." I motioned to the lever next to Kristy.

She did indeed remember and the boat became silent. Kristy then looked up at the tell-tales and sheeted in the main sail. She also made a slight course adjustment and the boat began to pick up speed.

"Well done," I smiled at Kristy.

"I love this boat! It handles better than any boat I have ever sailed and it is so simple to sail, super responsive, well balanced. It is wonderful," she was beaming.

I grabbed my camera and snapped a few pictures of Kristy at the helm. Her long blond hair was blowing in the wind. Her blue eyes against the blue water, her feet were planted wide like she was never going to leave and her hands were gripping the wheel all gave the illusion she was goddess of the wind and sea. I thought it might be fun to try it again later with her in a swimsuit.

I let her sail the boat for about 15 minutes and showed her the autopilot and suggested she get changed for the first setup. She set the autopilot and went downstairs in the saloon to change.

"Help! Jim, I need your help!" I heard from below a few minutes later.

I quickly checked the auto-pilot and then checked for traffic. I headed down below.

"Oh my gosh!" I said in surprise. There stood Kristy completely naked except for a bra. She had her head tilted back and seemed frustrated.

"I was changing and caught my hair in the clasp of my bra and can't get it unhooked. Please help," she said.

I fumbled with the mat of hair for about 2 minutes.

"Is there anyway we can get you in the cockpit where there is better light? I'm having trouble seeing," I finally said.

"I can't imagine why. I'm showing you almost everything I have," she said with a little sarcasm in her voice.

Kristy shuffled to the ladder. "Make sure I don't fall," she said.

"I'm right behind you. There is no way you are going to fall. My guardian angel insists accidents that happen to me do not involve beautiful naked women falling on me," I replied.

"Stop trying to make me laugh. Wait, are you back there?" she asked with some concern in her voice.

"Yes, I'd be counting freckles on your butt if you had any back there. Is all your skin flawless?" I asked.

She finally made it to the cockpit and said. "I wouldn't know. I don't make it a habit of staring at my butt, like some people," clearly frustrated by her predicament.

Kristy was now facing me and I could see her frustration. "Okay, turn around and let me se... give it another try." I fumbled and almost said the word 'see'.

My blunder brought an instant change to Kristy. "Nice save there captain." She smiled and turned a 180.

About 30 seconds later I had the bra unhooked but still hadn't gotten the hair out of the bra. Kristy felt the bra loosen and started to move her head back into a normal position.

"Whoa, your hair is still caught in it. Careful," I warned her.

"Well, help me off with my bra," she said, anxious to finally resolve the problem.

"Now that is a phrase I don't hear near enough in my life," I smiled.

I grabbed the offending area of the bra to ensure it wouldn't damage the hair and continue hurting Kristy. i pulled it off her shoulders. She slid her arms out and I handed it to her still attached to her hair.

"Thank you, I really appreciate your help," she said, now feeling bad for the attitude she gave me while I was helping her.

I stepped back finally looking at Kristy. "Oh wow! Blue eyes that are bluer than the water, hair that is more golden than the sunlight." I was like a boy seeing a woman for the first time. Examining all the wonders that stood in font of me. I looked into her blue eyes.

"She is the prettiest thing I have ever seen," I said

"Jim, you are shaking," She commented.

"Sorry. I've seen a lot of women and there is something special about one that is perfect - she's amazing. Can I touch her?" I asked excitedly reaching for her face.

Kristy paused and then a huge smile crept over her face as she realized the verbal duel that was repeating itself. "Oh you are good, very good. So, do you think we should have a safety meeting? You don't want to put a finger or hand in the wrong place," she smiled now getting into the flow of it.

"Well, not something I would want to single hand," that's for sure.

Kristy rolled her eyes. She then gave me an impish smile.

She focused back on the task of freeing her hair and in a few minutes she accomplished it. She held the bra in her hand and then threw both hands out in the air and off to her side showing her hair was no longer attached. "Ta Da! Got it!" She puffed out her chest at the same time.

I was caught completely off guard and stepped back and fell onto the bench behind me.

"Wow, you really are nervous around me!" Kristy said with some surprise, realizing that this grown man was acting like a little boy.

"Hello. You are drop dead gorgeous, have a great personality, smart, and you love to sail. I might be a little shallow but that hits a lot of high points for me." I started to gain some of my composure back and smiled at her.

I continued feeling a little bolder that she had not covered up yet. "So, do I hit any high points for you?" realizing it was a stupid thing to say as soon as I said it.

Kristy paused probably a lot longer than she needed to but clearly was going to milk my mistake for all it was worth. "Well... ah... er... you have nice tastes in sailboats," she said with an over amount of enthusiasm. "Uh... And you are really good with knots... or bra's. I'm not exactly sure which," her enthusiasm now dwindling.

She was crushing me and saw the expression on my face. "Okay, lets see what kind of photographer you are. Why don't you take some pictures of me right now," she smiled and gave me a wink.

My mood instantly changed and I quickly grabbed my camera.

She looked at the bra in her hand and dropped it on the deck. "We won't need that." She gave me an impish smile and then turned serious after I took the first shot. "These are just between you and me - no one else sees these?"

I quickly promised and began taking pictures of the naked Kristy. She got into the playful spirit of things right away and began doing a pole dance on the mast and putting lines on her like she was tying herself up.

She then got weirdly serious and laid down on a bench cushion and gave me a classic "pin-up" pose. She slowly opened her legs allowing me to photograph her completely shaved pussy. She went from classic nude to almost pornographic.

She reached down, opened her pussy lips and whispered. "Do you want to take photos of my virgin pussy?"

I almost dropped my camera. I moved in and began clicking away.

Then she whispered in a sexy voice, "don't forget about my happy clitty." She moved her finger down and began rubbing her clit. She got this dreamy look on her face, closed her eyes and began moaning softly.

I didn't know if this was an invitation or what it was but I had never been so aroused in my life. I put down the camera and moved my tongue closer to her pussy. When I made contact she moved her hand away and placed it at the back of my head. I gave her pussy about 6 licks from bottom to top, carefully avoiding "happy clitty." She started to moan even louder.

Then I took a long lick across the top of her her clit. "Oh Fuck! That's awesome!" She screamed at the top of her voice. I began an assault on it rubbing my tongue across it as fast as I could. Kristy went nuts. She was thrashing her head back and forth and moaning incoherently.

Suddenly she stopped and screamed. "I'm going to... I'm going to... I'm going to..." Her body tensed and got rigid as a board. "OH FUCK!!!" she screamed as her body began to shake violently. I hung on, giving her clit the tongue lashing she so deserved.

"STOP! STOP! it's too much," she screamed as she tried to wiggle out from my grasp. She laid there panting for a second trying to catch her breath.

She laid there for a minute not saying anything and then put her hands over her face and cried out, "oh my god I'm a slut."

I quickly laid down next to her and wrapped my arms around her and just held her. "Now, what is all this talk about being a slut? Is this something that you do often?" I said.

"No. I've never done anything like this before," she said refusing to look at me.

"So doing it once makes you a slut?" I asked I bit incredulously.

"No, but we just met. It can't be right what I just did," she started to look toward me.

"You just met my boat and yet you felt perfectly comfortable taking the helm and using it," I replied.

"But it is a thing. It was built and designed to be sailed." She was now looking at me making her point.

"I don't know how to tell you this but your lady parts were designed to do exactly what happened. They were designed to give you pleasure so that is what you did. It is society that makes up these silly rules about time lines. The thing about being an adult is you can live your life or you can let society live your life for you - it is always your choice," I replied.

Now smiling, "so do you always use other peoples words to convince them that you are right?" Kristy asked.

"You knew you were not a slut. You just wanted me to tell you." I paused for a second. "So what are the rules about how long people should know each other before they kiss?" I asked looking into her blue eyes.

She reached up, grabbed me and pulled me to her. We kissed for a few minutes, letting our tongues find each other. I felt a wind shift and the sails began to luff slightly.

"Excuse me," I said getting up. "The other lady in my life needs attention," I gave a weak smile.

"So this is what I'm competing with for your attention," sounding a little jealous.

I stopped and looked back at Kristy, who was completely naked and propped up on one elbow looking incredibly sexy. Just then the wind shifted back, the sails filled with wind and the boat picked up speed. "Nope, you compete with no one or no thing," I said returning to the bench and Kristy's arms.

"Make love to me," Kristy said with a pleading voice. "Make me a woman."

I paused for a second and looked into Kristy's eyes. "Okay, I might sound a bit conflicted here," I paused again brushing her golden hair off her face. "This is something I am going to remember for the rest of my life. It is such a special thing. I need to remember more than just the act. I need memories of you - your laughter, tears, likes, dislikes, favorite foods, what makes you happy, the stupid thing I did that made you angry. I need those things to be part of the love we share."

She looked at me and then a smile crept over her face. "Dammit! Adding - nice guy, thoughtful, smart, mature, caring. Shit, your list might be longer than mine." She continued to smile at me. "Hey, what about the pussy licking a few minutes ago? Isn't that a bit intimate?"