Hypnotism aboard a sailboat leads to sexual exploration
By: Date: 2023.01.19. Categories: Sex Stories Tags: , , ,

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

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

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

“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

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

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.

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