Stowaway Surprise

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When I’d left the dock I’d thought only of a moderate wind and the warm sun. I had one full week off from work with no obligations or appointments and in fact, no real plans at all other than spending as much time on the water as possible. Of course, most of my summer was spent on the water but it was always jammed between the regular hectic routine of life. This week would be different. No schedule. No compromise. No rules to hem in any fun and relaxation I might find.

The seeds for a week such as this had been planted in my mind in the waning drab days of March. It had been a trying year with rotating lockdowns and a workplace that seemed busier than ever. Dreaming of a solitary week on the water was sometimes the only thing that helped me to maintain a minimal level of sanity.

My intention had been to simply point north toward Lake Huron’s expansive horizon and see where the wind would take me. Unfortunately, wind was in short supply at 10am on this day and so I made the decision to motor out as far as I needed to find wind. If none was to be found, I’d still have the pleasure of a nice motorboat ride with some great tunes and a jug of gin and tonics that I’d mixed up this morning with some fresh limes. It wasn’t more than 5 minutes past the entrance to the lake and my t-shirt and shorts were discarded. One of the great things about sailing is the privacy it affords and with it, the opportunity to spend hours on end in the open weather without the need for any clothing whatsoever.

The wind built to a respectable 10 knots and finally I was able to set the sails. The boat settled in on a comfortable close reach and I engaged the auto-helm so that I might focus in on the warm sun and by now, my third G&T. Stretched out in the cockpit I considered opening my phone to catch up on current events but thought better of it as I considered that I am totally unencumbered and unaffected by any such events when I’m on the water. Not another boat was in sight and the shorelines of two countries were drifting further away as I adjusted my heading to 25 degrees off north.

As I lazed in the sun I noticed that my right hand had found its way to a familiar embrace around the base of my flaccid cock. It hadn’t been intentional and to be truthful, I didn’t even notice moving it there. Obviously, this routine had become so automatic that it occurred without thought. As early as I can remember in my sailing years, the privacy of sailing the beautiful blue waters of Lake Huron had often been my best opportunity for uninterrupted self-pleasure and exploration. As a much younger sailor, I would often head out in a small dingy sailing as quickly as possible until I reached that distance that put me out of sight and earshot of the beachgoers and other boats so that I could begin stroking myself to usually multiple orgasms.

A comfortable 10 degrees of heel and hardly any waves. The warmth of the sun beating down on my naked body was so intense that I’d already begun to think of my first swim. This was the setting as I felt my cock begin to harden within the all too familiar grip of my right hand. There was no need to rush and no fear of interruption as at least for the moment, I seemed to have the entire lake to myself.

Mostly long, slow, low pressure strokes to encourage my cock that it was time for some solo action with the guaranteed promise of a happy ending. I was a long way from needing the firmer grip. The rapid strokes that shake my balls like a pair of maracas. No, that would wait. First would be the almost indescribable pleasure of the long buildup. For the benefit of those not possessed of male genitalia I will do my best to describe it.

At first, there is a mild stirring sensation. Then a generalized wave of pleasure begins as your cock thickens and stiffens in your hand. There is a pleasurable feeling of the skin stretching on its own as it takes a more rigid form. That is the feeling that makes you want to stretch it even more. It is at this moment that the urge to grip with full strength is the most tempting and often the hardest to put off.

Just a little firmer and a bit quicker. That is canlı bahis what a cock is craving at this moment. Time and again you try to convince yourself that you can increase the pleasure without cumming too quickly but years of practiced stroking has taught you that once that hand begins to fly for real it becomes harder and harder to slow down and prolong the pleasure. And as if that wasn’t enough to deal with, that moment arrives when notice your balls tuck in tighter to your body as if acting on their own to control the violent swinging and slapping against your thighs. Unfortunately, this is yet another autonomous reaction that only heightens the general sensitivity and need to start moving things along quicker. All of this and the mind hasn’t even necessarily begun to imagine whatever scene will be created to force that cum to start building and racing toward the necessary eruption.

This is the male masturbation moment when great will power is required or the pleasure will simply be too much to ignore and though an orgasm is going to be the ultimate result either way, the buildup of the long, slow process is always way more satisfying than the quick ‘cum and get me to sleep’ type that is never as powerful.

I was at this very difficult masturbation crossroad when the sound of a throat clearing caused me to freeze like a deer in the headlights. My hand had come to a crashing halt and as my eyes opened I was completely and utterly shocked to see your naked form standing on the top stair of my companionway.

“What the fuck?”

“A stowaway, I guess you could call me. Remember, you said I could sleep on the boat whenever you weren’t using it. Just so happens that I decided to do so last night and only woke up when I heard you step onto the boat. I was waiting for you to come down below but you never did. When I realized that you were heading out I figured you wouldn’t mind some company on the water and thought it would be a funny surprise I was just about to come out to reveal myself after we left the harbor but froze when your clothes were thrown down at my feet and I realized you were naked.”

“Of course, I don’t mind having your company for a sail but, ah — I just thought I was alone and obviously… I was kinda in the middle of a private mo–“

As if I hadn’t had enough surprise for the day, your next move took the situation to a whole new level. Without speaking you began to strip naked as I watched with a growing almost animalistic passion. This was a body I wanted to see. Every detail. Would it match the images I had created in my mind on so many occasions over the years when you would unwittingly become the focus of my masturbation fantasies?

“Since I crashed your party, perhaps you’ll be more comfortable if I join you? My fingers can match you stroke for stroke and unless I’m wrong about how much men enjoy watching a woman pleasure herself, I’d say you are going to be very happy that I showed up!”

I couldn’t think of any response but noticed that my hand had once again, begun moving on its own. There was a dryness in my mouth as I watched your right hand teasingly move down between your legs. That moment your index finger began to push between your sexy lips and rub your clitoris in a rhythmic pattern almost sent me over the edge. When you slowly reached further and sank two fingers into your cunt I could see the slick wetness and understood that it was the wetness you needed for lubrication.

My mind was racing in all directions at your unexpected intrusion. Part of me felt frozen and could have instantaneously jerked myself to a powerful orgasm but I certainly didn’t want this to end quickly and other ideas had begun to emerge from the darker regions of my imagination.

“Come out here and bend over for me. Seeing as it was you who came uninvited and wanting to join me, I think it only reasonable that I decide where this is going to go. I’d suggest that you may want to brace yourself on the doghouse for what is about to happen!”

I was surprised when you did not speak but even more so when you did not hesitate. Obviously, I had made my desires clear and equally bahis siteleri so that you had decided to submit to my demands. I could feel my heart racing as I knelt behind you and simply took a moment to stare at the beautiful female body that was being offered to me — seemingly without reservation.

With your feet shoulder length apart I had a perfect view of your already reddened and engorged pussy lips. The protective hood of your clitoris had begun to recede allowing just the smooth, shiny pink tip of your clit to peak out. I looked on with utter fascination as a clear droplet of your juices began to run down the inside of your left thigh.

And so it was, that I would start with the thighs. Just gentle teasing caresses with the tips of my fingers to begin with. Up and down each leg. Getting closer but never close enough to the treasure. My full hands covered and squeezed the firm cheeks of your ass. Squeezing them together before stretching them apart to reveal you at your most vulnerable. Though you could not possibly have known it, today was the day that I was going to capture a prize that I very much desired and I was fairly certain that it would be a new and surprising experience for you.

After considering whether you had been sufficiently teased by my fingers I began to kiss every inch of your legs. I began down at your firm calves and slowly worked my way north where we both wanted me to end up. My fingers grazed the outer lips of your cunt while being careful to deny you the direct contact with your clit. As my kisses moved upward my index finger of my right hand began to tease your opening which in truth, had begun to open on its own. The thumb of my left hand found a ready supply of lubricant which had literally begun to pour out of you, and soon you were feeling the incredible sensation of a swirling pattern on the tight wrinkled skin of your asshole.

Soft moans had grown to a more guttural response and at that moment I knew that I could have you in any and every way that I wanted. No longer able to continue with the teasing due to my own needs, I decided to begin giving you some of what you wanted and obviously needed. Two fingers curled up inside you to cup and press behind your pubic bone while my thumb began to attack your clit. And knowing this is certainly not the first time you would have experienced this exact pleasure, I decide it is time to take you to a new experience.

I can tell that you are enjoying my fingers and I’m looking forward to observing your reaction as I make my next move. Sure enough, it was as good as expected. At the very moment my tongue pressed against your sphincter I heard you take a deep breath and felt your body tense momentarily. But as my tongue began to swirl and probe your body seemed to override whatever hesitations might have begun to form in your mind.

My tongue and fingers began to alternate the assault on your ass. I’m certain that by now, my intentions had become clear and no obvious resistance was being offered and we both new exactly what was about to happen. One finger first and with more insistence. Up to the first knuckle and then the second. Your hips began to move back toward my invading finger which signaled that it was time to add a second. Experience had taught me that introducing one to anal pleasure for the first time must be both measured and calculated. There would be stretching of course and perhaps a little discomfort not unlike any first attempt at intercourse. But a woman’s ass demands equal measures of pleasure and patience.

As I rose to stand behind you I imagine that you were expecting me to part your cheeks but I wasn’t quite ready yet. First, I had to experience the warm slick walls of your cunt. And so with just a moment’s hesitation at your opening I then thrust as hard and as deep as possible until I felt the head of my cock collide with the ring of your cervix. This was not the time for a slow build up. We both needed to fuck so very desperately and I was pounding you as hard as I ever had. Incredibly, your hips push back to take every insistent thrust. Both of us had begun to scream aloud to an audience bahis şirketleri of only us two. The sound of our wet slapping flesh was more intense than I had ever noticed.

I couldn’t possibly say how long we had been fucking like that but it seemed as though at least half of an hour had already passed. It was obvious that you had gotten dangerously close to cumming several times but I was keen to see that you would have to wait for it. I certainly wasn’t about to deny you but that ultimate pleasure would have to wait until the time of my choosing. And allowing you to cum with me deep in your pussy just wasn’t in keeping with my plan.

Without warning, I quickly pulled out and repositioned the head of my cock up against the nervously tight ring of your ass. There I simply paused. There was a mutual silence for the moment but each of us were breathing as though we had just run a marathon.

“You know that I am about to take your ass?”

You didn’t speak or look back over your shoulder but I saw your head nod in agreement.

“You want me to fuck your ass, don’t you!”

Again, and without hesitation, another nod.

“You may find this uncomfortable at first but I’m confident you will come to enjoy it and in fact, crave it once you have been taken in this way properly.”

No words from you but no apparent hesitation either.

I began with just the slightest pressure at first. Pushing the tip to see how much work it was going to take to have your stretched around me. Just a little more at a time. Slow but insistent. I hear you grunting and trying to stifle your reaction — perhaps just for your own benefit. A slight but noticeable stinging sensation I imagine but you seem every bit committed to that act as I.

When it seems right, I force in the entire head and can feel your tight ring clamp tightly around it. That’s the big move that has to start it all and I know from experience and intuition that a moment’s pause is necessary to allow your ass to become accustomed to its first ever cock.

I don’t ask but demand that you tell me you want me to fuck your ass. To my surprise, you shout your reply as if calling for help. I tighten my grip around your hips and again notice as the breath gets caught in your throat.

“You have had some time to get used to the stretch and the fullness. In a short moment you will feel me pounding you so deep and so hard that you will never ever forget this moment. But to start, it is you that will make it happen. Push those hips back and slide your ass all of the way to the bottom of my cock!”

It seemed as though the shaft of my cock sunk into you one millimeter at a time. The tightness was almost unbearably pleasurable but I managed to summon enough mental control to ignore the instinct to cum. As the wantonly spread cheeks of your ass finally pressed against my hips I knew that you were finally ready. Reaching around with my right hand, I began to rub your clit as my cock started to thrust in and out of your no longer virgin ass. I encouraged you to cover my fingers with your own and rub with me. I wanted to feel my fingers underneath yours. I wanted to be taught to understand your technique, your motion.

It was at that moment that I witnessed your discovery of a new type of pleasure. Any hesitation had disappeared and your hips willing thrust back to meet my every push inside you. Your fingers moved over your clit with a desperation I had never witnessed. Over and over my cock pushed in and out of you and I knew that neither of us would be able to last much longer. Out of the corner of my eye I noticed something that would bring the memory of this experience to a whole new level.

Without warning, I reached over and grabbed a winch handle. It was likely no more than 4 inches long but of suitable girth for my intentions. As I thrust the rounded handle between your wet pussy lips your entire body exploded in orgasm and mine along with you. I felt the rhythmic pulsing of your ass around my cock and couldn’t remember ever having been squeezed so hard. Jet after jet of my sperm shot into you as your own wetness exploded.

As I tried to catch my breath and started to consider just how amazing my orgasm had been, the only thoughts in my mind focused on how I would take you again and again and what new possible sexual adventures we might discover together.

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