The first day was far better than expected. After talking to David for a few weeks and meeting him to make sure he felt safe for his wife, I made all the arrangements and directed him in what to do to prepare. She came willingly. David was a good cuckold husband. He loved his wife and knew she needed to have fun with someone like me. They had been sharing her for many years, but she never had a lover or Bull to bring out and let her experience her true, submissive side. So, David put her on a plane to me for a week, neither of them knowing what was in store.

When she arrived we set sail on my sailboat, a forty-one foot sleek and elegant boat inside and out. She was easy to sail, capable of the Caribbean trip we had begun, but still comfortable and finished like the yacht she was. Most people name their boats after the things they do or enjoy the most. I named her “If You Dare.” Finding women who are not afraid to be daring, then pushing them to do the things they fantasized about and helping them enjoy it was what I enjoyed the most.

We had set sail from Miami Saturday morning and headed straight across the Gulf Stream to the Bimini Islands. I explained to Tana that we would enjoy the vacation, enjoy each other, and explore her submissive side. I told her we would do it in steps and that at any point we could stop. Day one was to let her feel comfortable with me. It seemed after just an hour into the trip she was as comfortable as she needed to be. We had played on the deck midday, she let me take her on the beach after we anchored, and she gave herself to me again before we slept. Day two would be a little different.

My alarm went off early at 4 am. We had awhile before reaching Nassau, and I wanted to be there in time to enjoy some time in the city. She stirred, but I kissed her and told her I wanted her to sleep as long as she wanted. I climbed out of bed, dressed quickly in some shorts and a t-shirt. As always, I went straight to the Navigation computer. We hadn’t drifted any considerable amount. The moon had set and the sun was hours from rising, so it was much darker than last night and the wind was much more calm. We were still headed into the wind so I raised the mainsail three-quarters of the way. I went to the bow and raised the anchor, and quickly stowed it, I would clean it after daylight. Back in the cockpit, I let the bow fall off away from the beach and trimmed the main to catch a little wind and ease up on our speed. I raised the main the rest of the way and trimmed it a bit tighter. I unfurled the jib and let it out using the light air extender. The course was set and entered into the autopilot. I set the marine turbine up and let it begin to recharge the batteries. We were off again.

I grabbed some juice and a bagel and sat back and relaxed. We had about one hundred miles to go today. I suspected the wind would pick up and we’d make seven to ten knots, though the first few hours would be slower. I made myself comfortable and nodded in and out of sleep for the next three hours. I would wake enough to ensure we were clear of danger, and then get ten minutes of sleep. The sun rose around 6:30. I debated waking her but knew an early flight, a lot of sun, and a lot of fun had worn her out. So I let her sleep.  We’d have more to see the next few days.

Tana finally woke and made her way to the cabin door. She looked a beautiful mess, but that look on her made me smile. She asked if she could shower and get presentable, and to my surprise she remembered and put a “Sir” at the end. I had told her yesterday that we would go a little further. That she was to call me Sir at all times today. “I am very pleased to hear you call me that Tana, of course you may get presentable. I would like you to wear the white bikini David provided for you. No top. You may wear a cover up if you wish. Take your time baby.” She smiled and turned back into the cabin. The wind had picked up as expected and so had our speed. Life was good.

By the time she had returned we had moved well out of the line of protection from the wind the small islands provided. The wind had picked up as suspected and we were headed further east . She stepped up out of the cabin wearing the white bikini as directed. She had opted for a hat instead of the cover up, much to my pleasure. Any sailor knows its not easy to look your best underway, but she looked stunning. As she got closer I realized she smelled fantastic as well. It wouldn’t take long for a little heat and salt spray to change that, but for right now she smelled as good as if she had come straight from a spa. I told her to grab herself some breakfast, she had the next watch. Breakfast in hand she came back to the helm. I did a little turnover, the course we needed, and then set the alarms in the computer and what they meant. I told her I was going to take a nap and clean myself up. I went below and crashed for forty-five minutes, then showered.

I came back out on deck to find her getting into the sailing. She was working to keep the sails trimmed, which is not an easy task on a boat this size for a beginner. When she saw me I saw a look of relief come over her. I took over and she plopped down. I told her everything looked great. The wind had picked up and she had adjusted the trim to keep from rolling me out of the bed, but she had obviously kept up speed.

We sat and talked about many things-hobbies, families, experiences and anything she came up with. Time just passed so comfortably. When the conversation got to our experiences her questions became much more specific. She wanted to know all the things I had done. I answered everything honestly and openly. She sat up and was much more attentive. She delved into why and how I felt what I did, as much as what I had done. I watched her as she asked and listened. I watched her closely, noticing when something was exciting her. It showed in how she crossed or squeezed her legs, and how her lips tightened or parted. Of course I played to those signs. Including more detail, telling it more like a story than just a list, and it had the affect I wanted.

I motioned for her to come over to me. Like a good girl she stood and walked over and stood in front of me. I reached up and placed my hands on her hips, leaned and kissed her stomach, and then slid her bikini down over her hips. My palms caressed their way all the way down the outside of her thighs, pulling the bikini down as they went. My hands left her bikini at her ankles and roamed their way up the backs of her legs. I’d watched her and looked at her legs before, but this was the first time I really felt them. I was both impressed and pleased with how toned her calves and thigh muscles were. Her ass was no different. My hands stopped there and held her ass. I kissed her stomach again then trailed a few kisses down from her belly button south. I enjoyed the smell of her, knowing she was wet. I stopped when I got to the little tuft of hair and looked back up at her. I could see she was wanting or hoping for more, but stood perfectly still. I told her, “Go sit in the bench seat in front of me and make yourself cum for me.”

“Yes, Sir” was her response. She held my eyes a little longer, then turned and did as she was told. I watched her turn and walk. She heard my “Mmm Mmm” and wiggled a little extra. She sat and laid back in the seat and moved her hands down between her legs. She kept her legs closed but I could see her hands moving slowly at first. Her right hand against her and her left on top of it. I could see her knuckles curling letting her middle finger apply more pressure. Seeing that and her hands movement up and down I had a clear picture in my mind of her one finger sliding in between her lips, moving low gathering more wetness and bringing it back to her clit. I watched her do this for a few moments and then looked up to her face.

I had held her face close, I had kissed her, and I had watched her face as she came from our sex, but I wanted to watch her face again. Her eyes stayed closed. She started with her lips closed, breathing through her nose. I watched her lick her lips knowing her mouth was getting drier. Her breathing was getting deeper, and she parted her lips to breath. Her head moved slightly side to side. Her eyelids would occasionally flutter. I was enjoying watching her, she was so sexy and natural.

I focused on her face, but out of the corner of my eye saw her body start to move, and I had to watch. Her stomach muscles tightened and her back arched. Then she gyrated her hips to curl upwards pressing against her hands. Her right hand focused on her clit, her left hand was obviously lower, at her opening. She moved like this for a few thrusts.  Then I saw her head tilt to her shoulder as her grinding and rubbing quickened.

From our fun yesterday, I knew her breathing would quicken and then stop when she was close. She was still breathing heavy but I noticed her pausing between each breath. She was getting close, her orgasm starting to build. My cock had been growing but now was straining against my shorts so I stood and walked to her. She had been surprisingly silent, her moans and groans and sighs suppressed.

I saw her breathing and knew it was near. I let my hand rest holding her cheek, “I’ve been watching you, cum for me now.” As soon as I said that her breathing stopped. She pressed her head to my hand and lifted her ass off the seat. Her right hand moved feverishly on her clit. And she came as I’d come to know, holding her breath and finally groaning and exhaling through her orgasm. Her hand immediately slowed as she came down. She looked up at me and our eyes remained locked as she settled down.

“That was beautiful Tana, Good Girl!”

I took her hands and brought one then the other to my mouth and licked and sucked on her fingers to clean them, tasting her. I knew how wet she would be between her legs, and the taste I got from her fingers made me want more. I had no previous intention to do it, but I knelt and let my hands open her legs. I leaned down and licked her softly knowing she would still be sensitive. I gently licked her lips and pussy. The amount of her wetness didn’t surprise me but pleased me. I knew how wet she felt as we fucked, And I had licked her in the heat of play, but this was the first time I licked her not to make her cum, but to enjoy her taste. A few licks and I moved over her and kissed her, and though she opened her legs expecting more, I stopped and went back to my seat.

When she saw I was done checking the boat she stood and walked to me. She knelt in front of me, sitting on her heels and put her hands on her thighs. I noticed how gracefully she knelt. At my age I know I could not get down that gracefully, and I wondered if she was just more flexible than I, or if she had to make an effort to do it as beautifully. She looked up and asked if she could please me.

I reached out and took a towel, folded it, and told her to put it underneath her. I knew the deck of the boat would get hard on her knees and ankles before long. I first talked about her positioning. “You have done wonderfully to come into this position. The most common submissive position agreed upon by most Doms is sitting like you are. The fact you put your hands on your thighs was good, but some will ask that the palms be up. Some Dom’s will be specific for your legs closed or open, some will require eyes up or eyes down. I will not make such demands on you until we come to a more formal agreement on our D/s relationship, if we decide to move in that direction. I will tell you however what I prefer, what pleases me.”

I continued by saying, “Your face is too beautiful for me not to want your head up, so I can see you and look into your eyes. I do recognize a time to be relaxed, and other times you may want to be more respectful. At those times I do enjoy your legs parted, your back straight, and your chest proudly out.” I stood and put my hand on her hair, bent down and kissed her forehead, and told her to remove my shorts.

She did as she was told. She undid the button and zipper. She avoided contact with my cock. It had softened after I walked away from her earlier, but started to twinge the minute I decided to stand. She wasn’t as teasing as I was. She put her two hands on my waist, just inside my hip bones, and curled her fingers into the waistline of both my shorts and boxers. She tugged them downward, watching intently as my cock appeared directly in front of her face again. She stretched the waistband enough to let the center of it slide down the length of my cock. When it was finally free, it twinged upward as she watched. She finally looked up at me as she took my shorts all the way to my feet. I stepped out of them, and she put her hands back on her thighs. I looked down at her and her eyes were on my cock, and I saw her first squeeze her thighs together, then realizing she opened them back up. I loved that she was remembering and complying without direction.

“I would like to make you cum, Sir” was what I heard as her eyes finally looked up again. I responded with a smile and said, “You may start with just your tongue, you may lick and kiss my cock, but you are not to take me into your mouth or hands.“

She slowly moved her face close to me. She put her mouth to the side of my cock, down at the base and kissed it there.  Then she stuck her tongue out and moved it to the underside. She turned her head and as she did her tongue slid from the base to the head slowly. She obviously knew how to make me and any man happy. She slid it right back underneath. As she reached the base she curled her tongue upward licking the base until at the top. Then she pressed the underside of her tongue against the side of my cock, the tip of her tongue still pointed upward. My cock was fully hard and sticking straight out by now. She slid the underside of her tongue down along the length again, pausing when she reached the top. She saw the pre-cum drop sitting there. So she let the tip of her tongue roam from the top and made a circle around the edge of my cock head. As she did she wiped the pre-cum with the bottom of her tongue. She moved her head back and I watched her close her mouth, obviously trying to savor the drop, no matter how small the amount.

She moved her head to the other side and repeated much of the same. After a few more licks I placed my hands softly on both sides of her head and guided her to look up. “You may now take it in your mouth, but you are not to use your hands. Make me cum.”

She looked in my eye and said, “Thank You, Sir” and smiled, then placed her mouth onto the tip of my cock and let it slide down. She made sure her lips were fully on my cock and her tongue rubbed the bottom of my cock as it moved inside her mouth. She slid back and then most of the way down again slowly.  She retracted back just as slow. She continued this slow steady and deliberate pace. It felt wonderful. My hands remained on her head not guiding or forcing her, just feeling her movements.

She moved her hands to my thighs and continued to service me. Her plunges onto my cock were creeping slowly further and further down my cock. And within just a few minutes she leaned forward allowing her neck to straighten completely and take my cock completely down her throat. She did not rush though. She kept a slow and steady pace which was working wonders on me. As much as I wanted to grab her and start face fucking her, I let her please me how she wanted.

She took me deep in her throat and held me there. I thought that felt great but then as she held me deep she started moving her tongue just slightly towards her lips and back. That little bit of movement felt crazy, and by my response she knew quickly that it was working. She stopped and took her mouth slowly off, and then right back down. She took me deep again and applied her little trick again and I groaned. She pulled off of me again, this time all the way off and looked up. “I’m glad you like that, Sir.” She swirled her tongue around my cock head again, then down she went. I didn’t need to thrust to get my cock deeper, she had my cock buried in her mouth each time now. But my hips instinctively started moving as my orgasm built. I was coming closer and closer.

My movements and my sounds gave me away and she picked up the pace. She started moaning as well. Whether she was excited she was pleasing me, or excited herself didn’t matter to me, I loved it. She still took me deep each time, but didn’t pause, didn’t tease. “That’s it Tana, God your mouth feels good!” she kept going, trying to watch me as she did. I couldn’t hold out any longer. I moved my hands back to her head, and pulled her deep and held her there briefly. My cock was pulsing and building. Her tongue moved again but this time she stuck it all the way out and was licking my sac. That did it.

I pulled my cock back and let the first shot of my cum hit her tongue. Then I pushed it back in and let the rest of my cum shoot as deep into her throat as I could. Her mouth was perfectly wet with spit but the added cum on her tongue made her mouth that much wetter and sloppier. As she swallowed, the rest shot down her throat, and her tongue forced some of the cum past her lips. After my twitching and shooting stopped, I let her slowly pull back off my cock. She sucked on it as she eased off it making sure not to waste one drop. When she pulled back she saw there was a bit of cum on the base of my cock. She moved to the side of my cock and went in and licked it off. She finally leaned back onto her heels. She looked up with a wonderful smile, a proud look on her face. She realized that one drop had escaped and hung just under her lip, and licked it up as seductively as she could. It may have been as natural a lick as possible to her, but to me it was incredibly hot. I sunk into my seat behind the helm and pulled her up next to me. She kissed my neck. I imagined it was because she was afraid to kiss me after swallowing me, so I turned my head and kissed her.

We continued on, talking, sunbathing, and relaxing. She continued to be a good sub. I made her prepare lunch, and we ate lightly again. At our present speed we would reach Nassau on or near schedule, leaving us a few hours to enjoy the city before my dinner and evening plans.