Hypnotism aboard a sailboat leads to sexual exploration

I had only met Phil earlier that week, in a local bar and grill. I was alone, and so was he. We began to talk as we ate and drank, and learned we had many common interests. For one, he had a sailboat and I loved to sail but had no boat.

As we continued to talk, the TV over the bar showed a short segment on hypnotism. I said I was trying to learn hypnotism, while Phil expressed skepticism that it was even real. One thing led to another. We moved to a booth in the far corner and I was able to hypnotize him and leave a post-hypnotic suggestion in his mind. I woke him, said it was no use, that I couldn’t hypnotize him, and we finished our drinks while arranging to go sailing on the coming weekend.

Saturday morning was clear and warm, but nearly windless. Still, I convinced Phil that we should go out. Perhaps the wind would pick up later in the morning. We motored out miles from land and other boat traffic. Perfect for privacy, I thought to myself.

Phil was standing by the tiller, steering with his right hand and talking. He was wearing a T-shirt, shorts, and boating shoes. He had a good slim physique, and the bulge in his shorts held my interest. Here goes, I thought. Then, aloud: “Phil-boy, Phil-boy, the sailorman.”

Instantly, Phil stopped talking and he stared straight ahead with a blank expression on his face. Man, this just might work! I continued: “Get yourself naked as fast as you can.” Phil immediately stripped off his clothing and shoes, and resumed steering. From my seat across the cockpit, I could see he was well hung, uncircumcised, and quite hairy.

I went below, stripped myself naked, and brought out my digital camera, tripod, toiletry kit, and a pail of warm water. First, the camera: “Phil, smile until I tell you to stop.” He adopted a warm smile and I took a few pictures of him standing there. “Put your left foot up on the cockpit seat, with your left hand on that knee.” This opened up his crotch nicely, and the morning light was perfect for several more shots.

I moved his clothing and shoes and sat directly in front of him, shooting several close-ups of his soft cock and hairy balls. Due to the warm weather, his scrotum was hanging loose and his balls were plainly visible in the sac. Shooting with my right hand, I took photos of my left hand fondling his balls, gripping the top of his bag, and holding his cock, including stripping his foreskin back off the head, which I found fascinating.

I put the camera on the tripod and used the self-timer to take a few shots of me fondling his genitals with both hands, both close-up and showing the whole situation from a more distant viewpoint. My own body is nothing to be ashamed of, and I enjoyed having photos of myself naked.

With my camera hand-held again, I ordered: “Get a full erection, but slowly.” As Phil’s cock grew longer and thicker and began to rise, I took a series of close-up shots in sequence. The last shot was of his full erection, with the foreskin pulled back off the head by the length of the shaft. What a marvelous cock he had! With the camera again tripod-mounted, I took a series of shots with me fondling his balls while stroking his long cock, and ended with a shot of me taking the head into my mouth. My mind was swimming with ideas.

I moved to the other cockpit seat where the light would be better for what I had in mind. “Phil, engage the self-steering and come stand over here, right in front of me.” He complied, and his erection and ball-sac were just a foot in front of me.

I admired the intricate pattern of veins while preparing my toiletry items. First, I used small scissors to cut most of the hair from his genitals, throwing the hair overboard. Then, using warm water, I soaped his genitals, taking pleasure in the feel of everything as they slipped through my fingers. “Put one foot up on the seat beside me.” This opened up his crotch, and I soaped back to his asshole.

I wiped off most of the soap and added shaving cream, working it into the hairiest spots. Then, using a safety razor, I proceeded to carefully shave the base of his cock and the front and sides of his scrotum. Then I noticed his scrotum was contracting and there was a drop of pre-cum glistening on his cockhead. Oh, oh. “Phil, you cannot cum except on my command.” Still smiling, he nodded. “You can stop smiling for now,” I added.

“Move here beside me. Lean your elbows and left knee on the seat cushion, with your right leg and foot braced on the cockpit sole.” This gave me a full view of his ass and the back of his scrotum, which I proceeded to lather up and shave, including the area right around his asshole. I noticed his asshole contracted whenever my fingers moved across it, which gave me more ideas.

I finished my shaving and wiped all remnants of lather from his crotch, then dried him. I took a rearview picture of the completed job, with his balls hanging way down.

Then, I applied a lubricant generously to his asshole, rubbing it in and gently inserting a fingertip, then two. His sphincter was fighting me. “Phil, relax your asshole.” Immediately, I could insert three fingers completely into him. Reaching forward between his legs, my left hand found his cock, still erect and pointing away from me. I attempted to bend it downward and backward, but it was too rigid. “Relax your erection half way — still long, but not so stiff or thick.” His cock relaxed in my hand and I pulled it back beside his ball sac and up into his ass crack. The length was good; the head extended nearly three inches past the anus.

With my left hand, I held the shaft against his crotch. With the fingers of my right hand, I pressed the cockhead against his lubricated asshole. Slowly, it disappeared into that brown wrinkled hole until all of the extra length was inside him. “Phil, tighten your ass to hold in your cock.” I could see the sphincter grip his cock shaft.

“Get erect again, but not enough to pull your cock out.” His cock quickly became thicker, straining to open up his asshole. I cleaned my hands and took a few pictures from various angles. Then, with some sympathy for Phil, I said, “Phil, you can cum four spurts now.” His cock moved and his ass gripped, and he moaned four times, then rested his head on his forearms, breathing hard. His nuts had risen part way, but now resumed hanging low from the heat and the exertion.

I played with his balls with both hands, pulling them down gently, pulling them apart sideways, and feeling the internal cords between my fingers. With the camera in my right hand, I shot a few photos of my left hand holding his balls loosely and with my entire hand gripping his ball sac above the balls — it was hanging that low. And that gave me another idea.

“Soften your erection and loosen your asshole.” Phil’s cock began to pull out of his ass. With a pop, it came out, then swung forward. I pulled it back down to vertical and washed it well with soap and water. Then, my attention returned to his balls. I noticed the right one hung slightly lower. I gripped it and gently pulled it back and up, and it reached an inch beyond the asshole. The left nut reached the ass, but just barely.

I returned to gently pulling down on the scrotum. Then, before they could retract automatically, I pulled the right one to the asshole and pushed it in! “Tighten your ass,” I commanded, and the right ball remained trapped. The left one was a small problem, requiring some effort on my part to get it into position. Finally: “Loosen your ass,” and I held the left nut just inside the anus. “Tighten your ass,” and the sphincter slid over the ball and around my finger, which I removed.

Phil was moaning and panting. I quickly cleaned my hands and took some pictures. I noticed how, with his scrotum pulled back out of the way, his cock hung down like one large teat on a cow. So, I lubricated it and began to “milk” it with both hands. Phil was panting more heavily now. “Get fully erect now,” and his cock swelled in my grip. I had to have pity on him. “Phil, you can cum now, all you want, but don’t let those balls out of your ass.”

Although his body wanted to contract his scrotum as he came, his ass held it tight. I wiped my hands and photographed his cock spurting a growing pool of cum on the seat cushion. Finally, he was done. “Loosen your ass,” and his balls came sliding out to hang by his spent cock. I washed his scrotum, cock, ass, and entire crotch area, and dried it, while Phil recovered from the experience. Then I cleaned up the pool of cum. “Lie down and rest a while,” I commanded, and he complied. I think he even fell asleep for a short time.

While Phil was resting, I searched through some lockers on the boat and found a supply of quarter-inch rope, which I brought to the cockpit. “Phil, wake up now. Stand here in front of me and get a full erection.” He complied. His scrotum was still low, and I began winding the rope around it, pushing his nuts tightly to the bottom. Then I wound the rope around his big cock in a close spiral, until only the head remained showing.

The result was that both his cock and his balls extended forward from his crotch. I tied off the ends of the rope and took some pictures closeup and of Phil standing at the tiller with his genitals neatly wrapped and protruding. Although this took only a few minutes, both his cockhead and his balls were turning reddish- purple, so I removed the rope right away to restore blood circulation.

“Phil, we’ve been out here for hours. You need to take a piss, and I’m going to hold your cock while you do it.” I placed my camera on its tripod in the cockpit, aiming it forward along the well-lighted side deck. I placed Phil into position, told him to get an erection and smile at the camera and start pissing when I ordered him to.

I turned him so his cock would be in profile, sticking out over the safety lines, then set the self-timer. As I tripped the release, I sprinted onto the cabin top, said, “Piss now!” and was on the far side of Phil, gripping his cock and grinning at the camera, when the camera took our picture. “Stop pissing!” Well, this is not easily done, but Phil obeyed me. I reset the camera and repeated the events necessary for another shot. In review, both shots turned out well — sharp and clear, with a stream of piss arcing far overboard and my hand encircling his hard shaft. This time, I let Phil finish his job. We both returned to the cockpit.

“Phil, you can stop smiling now. Tell me of any sexual fantasies you have.” He thought for a few moments, then said, “Most of my fantasies have come true today, but there is one more I can think of. Sometimes, I wonder what it would feel like to do anal intercourse on someone.” For at least ten seconds, I considered the formidable thickness of Phil’s cock, which was still erect. I stroked it, gauging its circumference.

“Phil, lose half of your erection — still stiff, but not so large.” The result was not quite as stiff as a full erection, but would do the job. I took a tube of lubricant out of my kit and applied it generously to his cock and to my asshole and the area around it. “Lie down on the cockpit seat, cock up.”

He did, and I straddled him, supporting my weight with one knee and the other leg extended. Here goes, I thought to myself. I had Phil hold his cock in place, because both of my hands were busy holding my ass cheeks apart. I settled onto his cockhead and slowly kept increasing my pressure onto it. I could feel my asshole opening very gradually, and wished I could self-hypnotize myself to relax my sphincter! Very slowly, I lowered myself further, then stopped, raised myself slightly, then resumed my descent.

I repeated this each time the pressure seemed unbearable, but my ass was slowly stretching to accommodate Phil’s half-erect cock. Then, due to my awkward position and the length of time that was passing, I suddenly got a terrible cramp in one leg! Without a thought, I took my weight off that leg — and down I went! My ass was burning, but Phil’s cock was entirely inside me. I massaged my cramped leg for a few minutes as I sat there, impaled. As the cramp eased, so did my ass pain.

Experimentally, I put weight back onto the leg and raised myself six inches. This left a good three inches of cock still inside me. I settled back down. Phil’s eyes were closed and there was a slight smile on his lips. I reached for my camera and hand held it for several shots, hoping I was aiming it back at us well enough to get some decent photos. I began raising and lowering myself rhythmically, slow at first, then speeding up. “Does that feel good, Phil?”

“Oh, yesssss.”

“Do you want to cum, Phil?”

Eyes still closed, he nodded vigorously.

I settled at the base of his shaft, reached behind my ass, and gripped his balls. “Phil, I want you to get a full erection and cum until you are done.” This may have been a mistake on my part! His cock got thicker and longer and thicker and longer, until I thought I might be damaging myself permanently. But the pleasure on Phil’s face, combined with the feel of his pumping, throbbing cock inside me, made it worthwhile. I could feel his hot cum filling my guts. Finally, he seemed to collapse, and his erection began to shrink slightly. I took advantage of that opportunity to raise myself up and off him. There was a popping sound as his cockhead passed out of my poor, sore ass. Surprisingly, I noticed no trace of blood. My sphincter had stood the test! I cleaned Phil’s cock and caught most of the cum that was draining from my ass as I sat down gingerly, first on one cheek, then the other.

By now, it was late afternoon. “Phil, turn the boat around and head for home.” Our trip back to port was uneventful. As we neared the shore and other boat traffic, I ordered Phil to get dressed. I got dressed, “Phil, you will have no memory of what has happened today. As far as you can remember, we had a nice day sailing, and you will want to do it again next weekend. When you see your shaved crotch, you will not be surprised, because you will remember that you have been shaving yourself for years. By the middle of next week, it may start to itch, but this will not bother you. I will shave you again next Saturday.”

Phil nodded in understanding.

“Now, close your eyes. On the count of three, you will be wide awake and excited by the great sailing we’ve had today. One, two, three.”

Phil opened his eyes and began talking excitedly about the sailing. It had been a great day for me, that’s for sure, and I was looking forward to next weekend! I was already compiling a mental list of toys to bring along. Maybe I’d even bring along another person; whether a man or a woman, it opened up many possibilities…

THE READER may wonder why I didn’t fuck Phil’s ass. Well, I’m not equipped to do that. Didn’t I mention that I am a woman? I suppose I just forgot.