A few weeks ago I had met David for the first time. After weeks of chatting that meeting was meant to build the final trust needed for him to share his wife with me, his beautiful wife of more than 25 years. The meeting went well, as expected. Men are drawn to trust and follow me. Women are drawn to trust and want me. I don’t say that out of arrogance, I’ve known I was a true Alpha male since I was 21. My early experiences both in my professional life and my sexual life helped me understand my natural openness and integrity went much further than any arrogance.
Before we met David had a particular encounter he wanted for his wife Tana. But as we began communicating he developed two other potential options. He explained them all to me. I told him I would chose the option and set things in motion. Leaving him to wonder and imagine. David was a cuckold. He lived to please his wife. I could have told him some specifics of my plans, but I’ve learned by not doing so I would further feed his own anticipation and excitement by forcing his own mind to naturally fill in details that met his desires.
Before the night ended I had watched Tana walk in to meet him. I saw the demonstration of the love I knew they had for each other. The simple hint of excitement they each showed as they spotted each other for the first time after a long day. The looks they gave each other as they sat. Her knowing he had met me, him knowing she knew.
David was excited and proud that he had taken steps to soon give her a wonderful time. He was confident he had done well and all would be a tremendous result. He also knew he might be involved, or left out and teased, but the thought of both excited him.
Of course, my first sight of her was spent taking in her beauty. I was as taken by her as every other man in the bar, most of them half her age. She was tall, fit, perfect curves, with a gorgeous face. But the way she was put together and carried herself made her more attractive to me than her physical beauty. I watched her walk in head held high, wearing heels, a pencil skirt, fitted buttoned white shirt, and perfect hair.
I could tell she knew she could ask him questions about the meeting, but I could see she was toying with him. Making him keep his excitement built up inside, not able to share it with anyone. She gave him looks that could have been mistaken as bitchy teasing by someone who didn’t know the dynamics of their cuckold relationship. But I knew it was a loving tease, one that let him know she was letting him do this for her, but that she could completely change anything at any time. And they both knew he’d do anything she wanted.
As I left she was reading the note I had given for her. “Tana, David has entrusted me with giving you another wonderful HotWife encounter. Though there are surprises ahead, you will have a wonderful time! Until we meet, smile for him as I know how much he loves you.” I wanted to build her excitement as well. But the planning had already begun in my head. The time, until we met would be as exciting to me as it would be to both of them. All for different reasons.
Two weeks later I mailed the envelope I addressed to David to let him continue to feel like he was making all the preparations for her surprise. I also wanted to help keep the cuckold dynamic strong, I was making him send her to me.
In the envelope was a plane ticket for Tana to Miami for the coming Saturday. It also contained instructions. He was to present the ticket to her and tell her the week was set. He was to tell her he would do the packing for her based on my instructions. And lastly he was to help her prepare by ensuring she had any appointments she wanted, hair, manicure, pedicure, or waxing. Based on our email discussions I knew she would want them all.
I had arrangements to make myself. A week with Tana would be wonderful. But I took three days prior off as well to prepare. I arrived in Miami and made my way quickly to the marina. Walking down the dock was always immediately relaxing. I get a rush of excitement when I see her. I named her “If You Dare”. Some would consider this a boat, some a yacht. I would never say my boat was as beautiful as Tana, but it is as exceptional when compared to other boats as Tana is when compared to other women.
It’s an Alerion 41, red hull and blue freeboard. With two cabins it sleeps 4 in very nice luxury. Sleek wood trim and expensive furnishings throughout bring out comfort and style. It is a comfortable and easy sailing vessel. I have no idea if Tana has sailing experience, but I have no problem handling it alone, with Tana’s help we could go anywhere. Checking out the boat itself would take just a day. But arranging for provisions, then charting and registering my routes and destinations would take time. I stowed my gear and began the preps.
Friday evening arrived and all was set. The weather forecast could not be better. The destinations would all be accessible and based on slips available around them it did not appear my choices would be overly crowded.
I had just showered and was ready to relax. I grabbed a rum & coke and relaxed in the pit. It wasn’t long after that I felt the vibration and looked at my phone. David texted just as instructed. “My wife will be with you tomorrow as scheduled.” The exact message he was instructed to send, at the precise time. I knew that meant every other instruction was followed.
I looked up at the clear sky and took in the moon. I have always had an odd fascination with the moon, but tonight I looked to verify. The moon was in a Waning Gibbons, meaning nearly full. We would have nearly a full moon for the entire trip. I took a sip and pictured Tana standing on deck, and the moonlight shining off her body. I closed my eyes and relaxed. Enjoying the thought, the mental picture, and my drink. This time tomorrow it would be more than a mental picture.
Saturday morning arrived and I watched the limo pull to the end of the pier. I had sent it to meet her at the airport, so as soon as the driver texted they were leaving the airport, my excitement peeked. To anyone at the marina I looked as cool and collected as ever. There was never a time I felt nervous or worried. I am always sure things will go wonderfully, in part because of my planning, and in part because of my personality. I’ve had women come up to me and tell me more than once I had a look of confidence. The first when I was 23, she had to be in her 40s. But that doesn’t mean I don’t get excited about opportunities to enjoy a wonderful woman. That she is someone else’s wife is even better.
The limo stopped, and the driver opened the passenger door letting her out. She stepped out and looked every bit as beautiful as I remembered. I did not give David instructions on what she was to wear while traveling, I knew she would travel as the classy woman she was, and I was not wrong. She stood there in her yellow sundress, and modest yet sexy shoes. As she waited for her bag from the trunk, I began to reduce some of the mooring lines. I knew the driver would walk her to me. This let me keep her anticipation building for just a few more moments, again letting her desires and fantasies fill in the unknowns I was presenting her with.
With just two mooring lines left in place, and ready for a quick departure, I stopped and stood on the dock waiting for her. Looking at her for the first time, and as the driver directed her to me and the IYD, she was able to see me for the first time. I caught her smiling as I looked up at her, From a distance I could not tell if it had a tint of evil grin, or a blushing nervous grin. It didn’t matter to me, she was smiling.
I walked to her and took her hand, not to shake it as a greeting, but to hold it as a sign of affection. I looked at her and smiled, “I’m Bill, welcome aboard the “If You Dare.” I helped her take the small step on board, still holding her hand.
She continued to smile as she climbed on board, “I suspect that is a very fitting name.” she said with a little laugh.
I grabbed the bag from the driver and as he walked away, I stepped on board and answered back, “Indeed it is, and thank you for being daring.”
“David didn’t tell me much, but I’m sure you know that. So yes coming here did take a little nerve, but he was so excited for this I could not back down. If he had shown one sign of nervousness I might have felt different.”
I answered her as I walked her into the cabin carrying her bag, “Yes I knew he would feel empowered as a cuckold to set you up with something he knew would be so wonderful for you, and this week will be wonderful! I also knew unlike your past encounters, giving you to me for an entire week would be thought of as a big step in his submission to you, and to me, so here we are.”
The main cabin area was pretty simple to explain. The steps led down to the dining and kitchen area, as well as the internal cockpit. I told her I would teach her a bit about sailing as the week went on if she wanted. I pointed out to the rear of the steps was the aft stateroom. I showed her the head (restroom) and then led her to the main stateroom.
I placed her bag on the bed, noticing the lock as I had instructed David. She caught me looking at it and laughed. “Yes he told me I was not allowed to see what was packed inside.”
I pulled the key out of my shorts pocket and handed it to her. “He loved surprising you didn’t he?” I asked in a tone that she knew I knew the answer. I wanted her to know that everything I do was designed to build upon this experience, for her and for him. The smile told me she was getting it.
I opened the closet and showed her there were a few things already there for her. A black dress, A white sundress, and a few wraps and cover ups already hung, next to a couple pair of slacks and fresh starched shirts for me. I pulled out a drawer from the storage area next to the closet and showed her there were a few bathing suits. “I have all my stuff in those two drawers” pointing to another storage area. “I’m going to go up to the cockpit area. If you have any questions or concerns before we leave you can come and we will discuss them. If you are daring, you can take a few minutes to unpack then come up and we will talk about a few things and then cast off.”
I gave her a quick glance before I moved towards the door, when she spoke I stopped and looked back at her. “David told me so little, but that he trusted you and wanted me to have fun. He told me he thought in just a short time talking, he felt you understood what I wanted and what would make me happy, so I am trusting him, and you.”
I smiled and she turned and reached for the lock and began opening her bag, so I left her to it. I knew there was little in there, so it shouldn’t take long. Most of the space was taken up by toiletries and make up, a few sandals and summer shoes. The only clothing he was to pack for the entire week were, a few bathing suits, assorted lingerie, two summer short or skirt outfits, and one outfit for her return trip home.
Of course it didn’t take her long and I had just pulled the tray from the refrigerator and walked back up to the cockpit. I was thrilled to see the big smile on her face as she climbed up out of the cabin. Still wearing the yellow sundress I took her hand for the last few steps and realized she was barefoot. I had no doubt she would go along the trip, but of course that was a good sign she was getting comfortable.
I let her sit on the recliner and of course showed her the tray of snacks, cheese, bread, grapes and pineapple, and some Italian meats. I knew she enjoyed wine so I had fully stocked the wine cooler. I had pulled a white wine based on the cheeses I had and popped the cork. I looked at her and didn’t have to ask if she’d like a glass. By now it was almost noon so I knew she was hungry, but the sigh and smile were enough. I handed her a glass and poured one for me. I sat and started the little welcome speech I had thought through for weeks.
“First let me tell you I am thrilled you are here and I am taken aback by how beautiful you are. I am glad I waited to see you walk into the bar a few weeks ago, if I had seen you for the first time today I’d be fumbling around in shock.” I took a sip of wine and watch her accept the compliment graciously.
“I’m sure you called David after you landed and we will call him again before we leave. I have a relaxing trip planned. There will be hours at sea broken up by rest and relaxation at some of the most beautiful beaches you’ll find. I’ve picked a few stops for their seclusion, and a few stops so we don’t have to cook every meal.”
I watched Tana as she selected a piece of bread, meat and cheese and handed it to me, and then fixed some for herself as well. I took a small bite so she would relax and eat something. “Now of course I know about the relationship you and David have. I know he is a loving husband and wants you happy. I know he is not a cuckold in the extreme fashion, but I do know your relationship goes beyond just a hot-wife or sharing situation. I knew sending you to me for a week, not knowing what I had planned would be a big risk for him, and you both. But I knew he enjoyed the nervousness, maybe even fear. Like you yourself said, had I sensed any hesitation I would have shifted plans to ease the large jump of this trip from your normal encounters.”
As I talked I watched Tana relaxing more and more. She stretched her legs out on the cushions and leaned back. Still watching me and listening intently. I am a legs and ass man, I cannot deny it. And when she leaned back and hiked the bottom of her dress just a tad to let the sun warm them, I caught myself sighing. And she caught me too, causing us both to laugh a little.
“Now for you, this trip will be a mix of a true Caribbean vacation, a weeklong sexual encounter with a man other than your husband, and a slow exploration of your submissive side.” Her head was leaned back in complete relaxation until she heard the last five words.
She remained in a relaxed position, but she clearly was now not wanting to miss a word or inference. “You are completely safe and I will never force you to do anything you don’t want to do. You will have safe words and I will stop immediately if I hear them. We will ease you in starting with simple instructions and control, and as I see how you react, we will go further and further. There are two staterooms on board. If at anytime you feel I am not someone you wish to play with, I will move to the rear stateroom, and we will discuss a slow or immediate return.”
I stood and looked down at her as I moved around the helm to her. Her eyes never came off me, and I purposefully broke eye contact to let my eyes move down her body. I sat down next to her, brushing against her legs purposefully. I took another piece of bread and cheese and handed it to her and taking another for myself.
“The relaxation part of this trip has already begun. When the last rope is cast off and we are underway, the vacation part will have begun. When the third part of this week starts is up to you. When you are ready, I want you to come to me and kiss me. Whether that is an hour from now, or two days from now, or not at all, it is completely up to you. If David was right in all he told me about your fantasies, and I suspect he was, this is the perfect opportunity for you to learn, to explore, and to experience as much about dominance and submission as you want.”
I looked at my watch and though we could sit at the dock and talk for hours, the sooner we left the more time we would have at anchor by nightfall. I knew she was hooked. I didn’t think that as arrogance, it was what she wanted, and what I wanted to give her. I was pleased. I admit my ego is fed when plans work out, when I am able to get into women’s heads enough to know what they want, without coming right out and asking them, and devise a way to give them exactly that.
This trip was a special boost as what I was doing to David was also an ego boost. I took another handful of food and ate giving her time to ask questions, but she sat, ate, and smiled. I left just enough silence that I knew her mind was racing, at one point I swear she was blushing.
I stood and reached out for her hand. “Now before we leave you need to go get your phone, and we will give David an update. We will have cell service only intermittently.”
She took my hand and I helped her stand. She walked past me to the cabin and I made a few preps to clear the air in the engine compartment and start the engine.
When she returned I held out my hand and said “We will take three pictures to send him.” She handed it to freely and I opened her camera app. I helped her climb up on deck and told her to hold onto the mast. I knew it had a nice view of Miami in the background. I took that picture then helped her back to the stern.
We will also let him know what the boat’s name is. I leapt onto the dock and got the second picture of her, standing above the vessels name in gold and the blue hull, her yellow sundress looked perfect, catching a slight breeze. David would see her smile as holding a tint of naughtiness, as did I. I leapt back on board and helped her back to her seat and handed her the wine glass. I sat down close, one arm around her, and held out the camera to take the obligatory selfie.
I handed back her phone, “I suggest you call him, you can go below if you’d like privacy.” She took the phone, and a large sip of wine. She asked if I minded if she facetimed him, of course I didn’t mind. She contacted him and they began their talk and I watched her while making last minute preps, trying to contain my smile.
“Hello darling, yes I’m fine, well the limo brought me to Bill’s yacht, we’ve had a little wine and lunch, and he told me what’s in store and I while I wanted to kill you the last two weeks for the secrets, I am going to have to thank you big time when we I get home. I heard David ask what was in store.
She responded, “Well I don’t think Bill told you his three part plan, a great vacation on a yacht in the Caribbean, a weeklong wife sharing experience, and an exploration of my submissiveness.” I literally heard his gasp and excitement. He asked when he would hear from her again. Tana looked at me not knowing how to answer and tilted the phone slightly, asking for help in answering and inviting me in view. I stepped over next to her to get in the video feed with her.
“Hello David. We will be sailing the Caribbean for a week. We will have days of seclusion, and days in port. I will ensure she checks at least once every time we move into cell coverage, which I suspect will be no longer than two days apart.”
As I was talking Tana had raised her free arm and put it up over my shoulder and wrapped it around my neck. I had a few more words with David and finally said we were about to shove off. Tana looked back at the phone, arm still around me, and both of us still in frame. “David I love you and thank you for this, but I do want you to know that for the next week I am his”, and she turned to me and kissed me. It wasn’t just a peck. Her mouth met mine and I didn’t hesitate to kiss her back, opening her mouth with mine and letting our tongues meet. My arms wrapped around her, hands on her waist. Her free hand moved to the back of my neck wanting the kiss to continue, and it did.
When our lips finally separated she looked up into my eyes and sighed. I knew she remembered what that kiss meant. She turned to the phone but leaned her head against my chest. “Good-bye David.” She ended the call, but didn’t move. I didn’t either, it felt good to hold her.
I knew the idea of giving herself to me was both new and important. I raised one hand to her head and brushed her cheek and ran my fingers into her hair. I felt her wrap her second arm around me, holding me. It felt like a wonderful hour long hug, but of course it was just moments. I kissed her again, just as passionately before easing my hold on her. She looked up and said “It felt good to say that.”
I leaned down and whispered into her ear softly, “I know.” I then leaned back and told her “but it’s time to get this journey underway.”
I told her to stand at the helm and just hold it steady unless I told her differently. I reached into the engine controls and started the engine. I then leapt to the dock, undid the bow line from the dock cleat and held it in my hand, then I made my way to the stern line and undid it. I leapt back on board holding both lines and we were underway.
I stepped down and took the helm, put the engine into gear and moved out easily towards the channel. Tana stood close to me. Once in the channel I told her to take over again, watching her for a few moments. “Make slow and easy corrections, I’m going to grab the fenders and lines, just holler if you need me.” After just a few more moments I climbed to the deck and pulled in the three fenders and stowed them. Then I wrapped the bow and stern lines I had thrown on board and put them in one of the storage bins.
I moved back to the cockpit and made my way behind her, my right hand on her waist, my left hand reaching for my wine glass. We had eaten most of the meat and cheese so I started back into the fruit. I fed her a bite or two as I let her get the feel of steering. The slow speed was enough to get just a little breeze through her hair and help the dress flutter enough to be inviting.
We came across our first boat heading the opposite direction, Tana looked over smiled and returned their waves. As our bow hit their wake it lifted and then plunged just enough to catch her off guard. Her legs buckled just a bit and she leaned back into me and I caught her and held her steady. I knew she remained back against me more than she needed but I didn’t stop her. I kissed her neck, “time for you to go below and get out of that dress, and put on a bathing suit.”
As she stepped around the helm I took off my shirt. As I set it on the seat I saw that she was looking back. She turned at the entrance to the cabin and paused. Her eyes lowered as expected, but she peered and studied me longer than most women would, knowing she would be caught looking.
I’m not a gym rat or a hard body, but for my age I do feel pretty good about myself. The tan may show a bit of grey hair on my chest but I work out and run regularly. I may not look calendar ready but pretty close. My pecs, abs, and leg muscles are all defined well enough to be seen. She finally looked back up and flashed a big smile as she turned and went below.
After a few minutes I saw her appear out of the cabin. I am sure my eyes spent as much time enjoying her as she did me earlier. She had chosen a blue bikini, not overly modest or revealing, one David had packed. But she looked spectacular! She had a white cover-up as well, open in the front, flowing down to her thighs.
I knew she worked out and I had no problem admitting she was more of a knockout for her age than I was. She had beautiful red hair to her shoulders, her natural posture accentuated her shoulders and chest. Her breasts were least a C cup and perkier than any I have seen on a woman her age. Her stomach was like mine, the abs were there, but not exaggerated. And her legs were long and toned, to my liking and beyond. I knew she rode horses and suspect that had helped keep her legs so shapely. I had taken a seat behind the helm and she came over to me and curled up into me. Life was very good!
The trip under power would take another thirty minutes before we were in open water so I took this time to let her get to know me. I told her to ask anything and we had a great conversation. She started with the usual things you would ask a new date. We talked about my sailing experience and the planned trip and I gave her some brief info, but little details. Just as she was getting into the sexual questions we hit the breakwater and it began to get a little rougher as expected.
When we were in deep enough water I turned out of the channel to get the sails up, knowing we might take a little longer than usual.
I then showed her that we could raise it by power but her first time she needed to do it the old fashioned way. I started hoisting the sail and had her keep the rest in its flaked position. I reached and pulled several times before I caught her staring, causing her to blush. When it was near the top I had her come pull the last few feet.
I stayed right behind her making sure the waves didn’t catch her off guard as she reached and pulled. She did it easily, and I said either the workouts or lifting those saddles had paid off. The Jib was curled so we didn’t have to hoist it. I took her hand and back to the cockpit. I turned off the autopilot and turned to catch the wind. The mainsail lit up and we heeled slightly, so I killed the engine. A few minutes later we unfurled the jib and trimmed both sails. We had a good steady breeze and we were set, heading east. The wind heeling us over perfectly, our speed was above what we needed to keep on schedule.
I let her take the helm and gave her a little instruction on how it would handle differently now fighting both the wind gusts, as well as the water. As we headed east we’d have to cross the Gulf Stream to get to our destination.
As she had the helm I pulled the chart up on the navigation computer and zoomed out so she could see the destination, South Bimini in the Bahamas. “We have about a 7-8 hour trip so we should be there by dinner time, and then we’ll anchor, rest and relax.”
I walked around the helm, and grabbed some suntan lotion. Tana had a beautiful tan already, but being in the sun all day we would both need it. “If you get too much sun we can put up a canopy but I imagine for now you want soak up a little.”
I made sure she was ok with the type of lotion and began to apply it to her shoulders first. I leaned and kissed her neck, almost sucking, whispering in her ear after, “I wanted to taste your skin before I put this on.” Then covered her back rubbing it almost like a massage, feeling her skin, and muscles. I followed with her arms, she moved to let me cover her well. I then reached around her and began applying lotion to her stomach, and then her ribs.
I put more lotion on my hands, this time moving down from her neck. I teased and paused at the top curve of her breasts, then suddenly moved lower over both of them at the same time, moving under her bikini top. Her head fell back against me and she breathed deep. I was rubbing in the lotion in as sensual a way as I could, and smiling. I briefly caressed her already hard nipples before I removed my hands and straightened her top. “This will not be on much longer.”
I squatted and began getting her legs and feet. Her legs were wonderful, perfectly toned, and immaculately smooth. I got to her upper thighs and she spread her legs slighty allowing me access. I covered every bit of her thigh, my fingers going just slightly into her bikini bottom. I covered her from crotch to hips, then back along her ass, ensuring I got slightly inside, in part to allow for movement of the bathing suit, and in part because I just wanted to. When I finished I handed her the bottle and asked her to help me out.
She did pretty much the same, starting on my shoulders and back. She did the backs of my legs next, and yes she reached her hands up my shorts but not completely to my ass. She then moved around in front of me, between me and the helm and started on my chest. I could say she did a thorough job ensuring the lotion was rubbed into my chest, or I could be honest and say she was enjoying touching me. I was enjoying it just as much. When I asked if she was going to do my thighs she blushed knowing she gotten carried away. She put more lotion on her hands and knelt in front of me putting lotion on my legs.
As she moved to my thighs I asked her “what makes you think you are submissive?”
She kept rubbing slowly thinking, and finally looked up and said, “Because I always want to please my lovers more than anything. Even David, I only tease and taunt him because he wants it. I don’t know if that is a good answer or not but it is what is in my mind.”
“That is a perfect answer. We will push that and explore that. You will find out there are many types of submissives. Perhaps we will get far enough to find out exactly what you need from a Dom/sub relationship.”
Her hands had moved inside my shorts again. I could see her looking directly at my crotch. I couldn’t tell if she was trying to see more what I was like, or whether she was fantasizing. I told her to take my shorts down.
She did as she was told, and though she did it slowly it was not out of hesitation, it was out of excitement. There was almost a tremble in her hands as she undid the button and zipper. When she slid my shorts down and exposed my cock she took a deep breath, and looked at me. I’m not hung by any means, my cock is six inches, maybe a tad more. I’ve been told it was thicker than normal. I’m no porn star but compared to the husbands and others I’ve seen in threesomes, I would say I am thicker than average.
She looked up at me, and I put my hand on her cheek, and caressed it softly as I moved my hand to the back of her head. I gave just the hint of a pull and her hands moved from my hips to my cock. It was partially erect when she lowered my shorts, but with her hands, and impending mouth it was now growing harder and harder. I almost laughed when I saw it looking like it was growing directly towards her mouth. She noticed too and smiled before taking me in.
Immediately the warmth of her mouth felt great. She took the entire head in and paused, then slowly slid down my cock. I instantly knew she was good at this, and it was wonderful that she took her time.
We had a full week ahead and she was calm and relaxed. She started moving up and down my cock. Taking it out and licking the entire shaft at times. Holding the base and playing with my balls, doing everything perfectly. She wanted to please me and it showed. This was her proving to me she was ready, maybe even thanking me for what’s in store. I let her do as she wanted with me. My hand moved occasionally on her head but never pushing or thrusting. It felt so good but I stopped her and pulled her to her feet and kissed her, my cock hard against her waist. “I don’t want to cum just yet baby” and pulled up my shorts.
I spun her around and showed her the horizon, boats heading in towards Miami all around us, none were closer than a mile or two from us, so I undid her top ties and exposed her breasts. I turned the autopilot back on and sat, pulling her to sit, her back to me, her ass on the edge of the seat between my legs.
I kissed the back of her neck, sucking and nibbling my way around. She leaned back into me and my hands were massaging her tits. Her nipples had been hard for some time now, but I was able to feel just how hard they were. And they were bigger than most women’s, not odd, just round and longer, sticking out further. I fingered them gently and firmly, deciding I wouldn’t get rough yet.
Eventually I moved my hand down to her crotch, as a good girl she opened her legs as my hand reached her waist. At first I moved it over her bathing suit, pressing soft at first, up and down over her entire crotch. Then I raised it to her waistline and slid it inside. I felt the soft tuft of hair which I knew would be manicured.
I touched her, she was wet, much wetter than I expected. I stroked her pussy up and down, circling her clit few times, then down to wet my fingers again. Her hands were on my legs, as she squirmed she squeezed. I loved the easy effect I was having on her. I let my other hand grab her hair and hold her head gently but firmly, as I picked up the pace, and moved her closer to orgasm.
I knew she was ready to feel my fingers inside her but I made her wait, going as slowly as she had with me. I started running up and down her pussy with my middle and ring finger. As I reached her clit I’d let it pass between them, then as I reached her entrance I let them circle the edge and dip ever so slightly in.
Her breathing had quickened and she began to moan, and I knew it was time. The next time to her hole I moved both fingers inside her. She was wet enough that there was no resistance and they went into her as deep as I could reach. I moved them in and out now, my thumb taking over the attention to her clit. She began to lose control and one hand moved to mine and was trying to move it deeper inside her. But I held firm, my thumb now strumming her clit like a guitar string as my fingers curled back and forth against her G spot.
She came without a scream but it was intense. As her body began to tense she took a deep breath. I could then feel her bear down holding that breath, feeling her legs tighten from calves to thighs. Her ass raised just slightly off the seat, her thighs not only flexed but squeezed against my hand. And then she came, marked by a moan and a long exhale. I held my hand still, applying pressure but no more movement, letting her come down.
I moved us to get more comfortable, keeping Tana between my legs leaning back against me. The sun and the heat kept us warm despite the wind off the sails. We relaxed a few minutes and I began a little more detailed discussion.
“Today we will ease into things, you have free reign to move and speak and ask anything. Tomorrow we start a little more serious, there will be more rules.
You ARE a submissive, I can tell, and I am certain you will enjoy the trip and our exploration.” We spoke for an hour or so, covering some things she had heard or thought she understood. She asked great questions. Like David had told me she obviously wanted this, not just for the pleasure, but more importantly for the understanding of herself.
She didn’t understand how she could treat David how he wanted, and still be submissive. She also didn’t know how far she wanted to go, simply to please men, or to be controlled by men. She had been tied with neck ties before, but never experienced real bondage.
She had never considered discipline or pain, but was curious if she’d enjoy them. We talked about how she had learned what she knew, and of course the Grey novels. We talked about the contracts, that a more controlling relationship might require one, but that we would not need one for this trip, unless she wanted one. By the time our trip was over we would be able to help guide her from here, whether that included me or not.
I told her she was not to put her top back on, that we were on our way to an anchorage that should be secluded. We should arrive with enough daylight to enjoy a swim, dinner and to just relax. She could put her cover up on if she wanted, but not button it.
We had gone through the snacks and finished off the bottle of wine. She curled up into me and closed her eyes and I could tell she was relaxed. I told her to sleep if she felt like it, and pulled out a small pillow I kept in the seat storage, and a blanket if she wanted it. She took the pillow but stayed curled up to me, her hands slowly caressing me as she eased into sleep. I took the blanket and covered her up, and put my shirt back on, the sun was wonderful, but we would get our fill.
She slept for more than an hour, an early flight, nervousness, and the few hours of sun we’ve already soaked up all took their toll.
The wind kept steady and we were making good time. A happy groan, followed by a stretch marked her rising. She looked up and smiled and thanked me for letting her nap. She stood and stretched some more and then moved back towards me and kissed me.
I watched her move below and as suspected entered the head. When she returned I offered her a water bottle which she accepted. I looked at my watch and the Nav Computer and told her we had about two hours to anchorage. She stared at me for a bit and asked, “What are we going to do for two hours?” She said with a clear sense of naughtiness, standing there topless but proud.
With the autopilot on I took her hand and led her up on deck and headed towards the bow. She was watching her step and still hadn’t seen them until I stopped at the main mast and held her, and pointed to the pod of dolphin swimming with us. About ten rising up out of the water and curling back down easy, sometimes coming completely out of the water so she could see the streak of light yellow at their faces. At the speed we were cruising the boat was still heeled slightly and riding the waves easily, and dolphin often were drawn to the noise and liked to play in a boats bow wake.
I put my arms around her to let her watch for a bit. “I’m sure you’ve seen them from the beach, but have you ever seen them this close?”
She responded as she leaned back into me. “No, they’re so beautiful.”
I was paying them little attention, and began to hold her more from passion and lust than to simply steady her. I could tell she sensed it too and did not resist it, so I let my hands begin to caress her. I started with her waist and stomach, then her shoulders, and then her breasts. It didn’t take much for my cock to begin to flood. I had given her hours of being a gentleman, but it was time to let her know there was much more to me than that.
With her still leaning back into me, I moved a foot between hers from behind and guided her legs apart. My hands then found their way to her hips and moved her bikini bottom down to mid thigh.
As before I found her wet, and her hips moved to meet my touch. I fondled her as before, bringing her close to orgasm, but stopping. I pushed her bottoms lower and she moved her legs back together to let them fall. I grabbed them and stuck them in my pocket so they would not blow overboard.
I turned her around and placed a hand on her head and she immediately began removing my shorts as I had wanted her to. My cock was in her mouth again, and it felt just as heated and wonderful as earlier. I tossed my shorts into the cockpit as she moved her mouth on me. This time she was more eager and raw. She looked up at me on occasion, I knew it was not to see my approval, she knew she was performing wonderfully.
She wanted to see me happy, see me enjoying it. And I gave her what she wanted. I didn’t give her the look of a grateful teenager as I suspected many men would have based on how well she sucked cock. I gave her the look of a man in control, getting what he wanted, and approving.
Again I wasn’t ready to cum in her mouth just yet. I wanted to be inside her, I WOULD be inside her. I pulled her up again and kissed her.
Then I moved forward to the edge of the cabin roof to the small built in pad for sunbathing allowed me to sit with my feet on the main deck. It took little guidance for her to straddle my legs facing me and sit on my thighs. She moved closer so I could feel her crotch at my cock while her hands were on my face. We kissed as I moved my hands to her ass, pulling her hips up against me, then sliding her pussy up along my cock and back down. I could feel how wet she was with my cock. It slid easily, and just this movement would make me cum if I wanted, but after a few more thrusts of her hips and my cock, I didn’t want to wait any longer to be inside her.
This time as my hands raised her hips up, I did not lean back and let her press my cock down. Instead, I raised her higher and leaned foreward keeping my cock upright.
She knew immediately and stopped her kiss, looked directly into my eyes as my hands moved her perfectly over me. I was pulling her down but she was pushing herself down just as much, and my cock was engulfed by her. Her pussy could not have felt better, but the look on her face as she felt my cock enter her made me happy. Her hands on my shoulder, her mouth open, breathing and gasping, and her eyes locked on mine.
I knew the pleasure she was feeling was from more than just the first feeling of my cock. It was the buildup of the last few weeks, the anticipation and the surprise the trip, the beautiful day we’ve had so far and the build up to this moment all fed into her feelings.
We both moved, as much in synch as any two people could be. We both moved for the others pleasure as much as for our own pleasure. A few more thrusts from both of us and she was finally able to close her mouth and kiss me again. I kept one hand on her ass to help lift and lower her.
My other hand moved to the back of her neck holding her kiss tight, then grabbing her hair. I pulled her head back and sucked on her neck, then lower to her breasts. I took one then the other in my mouth, sucking, nibbling, and biting softly. As soon as I did her moans and sighs became louder. Her hips moving with more intensity. I felt her ass clinching as she was trying to milk my cock and move her clit against my groin.
It was obvious every thrust was bringing her closer, and that thought alone hit me and my orgasm began to take over as well. One hand still in her hair, I moved the other from her ass to her neck. I grabbed it firmly, not choking, not yet. I pulled her face back to mine but I knew her breathing would not allow her to kiss me without impacting her orgasm. I let it build inside her as mine was.
Our foreheads were resting against each other’s. Her breathing stopped, and her movements stopped, her thighs squeezing against mine. I lifted my ass off the deck and pushed as hard as I could into her and she came. Her breath exhaling as she moaned, but her body still tense. The feel of her entire body cumming, mixed with the sounds of her exhaling, and the wonderful moan she let out drove me over the edge.
I came inside her. I pumped more and more of my cum into her, having not cum in days I knew it’d be a lot. Her already wet and warm pussy became wetter. With my last few spurts, her hips were now grinding slower and slower. I could feel her trying to draw the last from me, squeezing with her legs, abdomen, and pubic muscles. We finally stopped and she fell against me. My cock was still in her and still hard as I held her to let her come down off the high. A few minutes of breathing and I sensed another slow grind to her hips, and I smiled.
But I stopped her, put both hands on the sides of her face and looked into her eyes, then kissed her. After a wonderful few moments I broke the kiss, moved my hands from her face to her hips and lifted her off me. I paused her there for a moment. I let any cum of ours not buried deep inside her, or that pulled forward with the removal of my cock, drip out of her and onto me.
I moved her hips up and back towards my knees and she moved with my direction. She stood between my legs leaning forward to keep her face close to mine, so I moved her hips downward and she knelt between my legs as I wanted. As she was moving to her knees I moved a hand back to her hair grabbing it and pulling her ear to my mouth and told her to clean me.
She didn’t hesitate. She had one hand on my cock softly guiding it, allowing her to move her tongue along it. She licked me, cleaning me, just like she was licking a melting ice cream cone. When my cock was clean she began cleaning any other cum from my groin area. And at the end she took me inside her mouth again, completely. I sensed she was letting the saliva build inside her mouth, could tell her mouth was wetter than normal.
As she slowly withdrew her mouth from the head of my cock, she looked at me and swallowed. If I had been younger my cock would definitely have been hard again just from that look. But reality is we were both beyond our teens, twenties, and thirties. I was beyond my forties, but that didn’t mean I was done with her yet.
I stood and pulled her quickly to her feet and towards the bow. I had her hold the mainstay facing out over the bow. The boat had now pulpit or railings here, so she held on tight. I stood behind her, one hand on the mainstay as well, the other around her waist. As the boat heaved up and down slightly we were now being hit with spray, but strong sunlight.
My hand moved from her stomach down to her, and quickly I pushed two fingers deep inside her. I moved my fingers to scoop any wetness from her I could, my cum or her wetness. I pulled my fingers out, drenched and wet. I smeared the cum I had pulled from her, all over her lips and clit and began an attack on her. Rubbing and caressing softly, but moving faster and harder against her clit.
She moved her legs to meet the waves and her sensations, leaning back into me for more support. I didn’t know if she had ever cum standing up, but I intended for her to do so quickly. Her body did not disappoint me. She was still sensitive from our fucking and within just seconds she was moaning and breathing as a woman enthralled does.
I continued fingering her, rubbing her, circling and teasing her. I pushed my fingers back inside her from time to time. Her body jerked both from my touch and with her eyes closed the shock of the occasional spray catching her by surprise. After such a short time with her I could already tell she was building to another orgasm, which suited me fine. I wanted her to, and I wanted her to know I could get her off quickly, when ever I wanted.
I didn’t want her to fight it, and she didn’t. One of her hands let go and moved to my neck, as I was leaning in to kiss and suck on her neck. Her legs parted and she squatted and ground against my hand. I took the hint and buried my two fingers in her again and let her grind her clit against my palm.
After just three or four grinds like this she came. Standing as she came this time her legs tensed completely. She tried to grind against my palm but her thighs were squeezing so hard I had difficulty keeping the pressure on her clit. But that didn’t lessen her orgasm. As soon as she was over the peak a small scream came with her exhale. I stopped my hand and let her come down again. We stood like this for a moment, taking in the sun, and spray, and the sounds of her pleasure.
I walked her back to the cockpit, reaching into the cabin to grab a few bottles of water. We sat and drank them, both tired and still breathing harder than normal. I put my shorts back on and offered her the bikini bottoms. She took them but held them, not putting them on yet.
We discussed how good that was. She hadn’t cum standing before, she had thought at first it would be difficult, but cumming and trying to not fall over completely seemed to make it stronger for her. I knew this would be the case, she was not the first woman I made cum standing. I could tell she was even more excited for the week ahead.
I sat behind the helm watching the navigation computer, still on autopilot. She sat curled up against me, and we were perfectly comfortable with my arm around her holding and caressing her.
Thirty minutes later we saw land. She stood and walked up on deck to watch. She put her bottoms on, I knew because she naturally expected to see others. She didn’t know I had picked a secluded area. I took us off autopilot and moved along the coast to ensure we found a sheltered area with a good bottom for anchorage as well as perhaps some swimming and exploring.
I asked her to come take the helm and she did. I showed her quickly how to watch for plotted shoals or sandbars on the navigation computer, but to always keep her eye on the depth gauge. If it began to jump up and down to let me know, or if it became less than 20 feet.
I moved forward and prepared the anchor, pulling it our of its storage, leaving the controls on deck so it would release with a push of a button. Back in the cockpit I watched for the right spot and finally told her to turn into the wind. I released the jib line and began to furl the jib sail. As soon as the jib was in, we turned slightly and the mainsail gave us a little speed to take us the rest of the way in. I could have used the engine but decided not to bother. With 4 knots of speed I sent her to the bow, told her what button to push when I asked.
She was ready and we had moved to a water depth of ten feet so we turned into the wind again. I began lowering the main as we slowed.The sandy bottom was what exactly I wanted so as we came to a stop I told her to let go the anchor. The splash hit and anchor line fed out perfectly, the wind pushed us back and set the anchor firmly.
We were set for the night.
