I was reminded of Emily recently when I ran into her husband.
It has been 19 years since I first met her, and I thought of her in her bikini and of her bare
feet padding along a dock. I thought of Emily in a
long gown with a leg-long slit on one side, wearing sexy and strappy heels that
showed off her gorgeous feet.
While I chatted with Pete at a boat show, I knew right then
that I could not wait to go somewhere and masturbate to my mental images of beautiful and sexy Emily!
I remember when Emily and I first met. It was a beautiful
September weekend in 2000. Temperatures were around 80-degrees that day and
there was hardly a cloud in the sky. I had been doing a little bit of work on
my sailboat, which was parked in front of my yacht club. My attention was
diverted by another boat approaching the pier. It was crewed by five women,
several of whom were very cute. However, I was taken by the captain who turned
out to be Emily. Emily, I learned, was 38-years-old at the time. About 5’7 –
5’8”, she had a tomboyish look about her. She wasn’t remarkably beautiful in a
model sort of way, but she had this outdoorsy air with lean legs and a
well-defined body. I could tell because she wore a bikini top with running
shorts covering the bottom. Her medium-brown hair was up in a kind of bun but
when it was down, it went halfway down her back. She had square, sexy shoulders
capped by a wonderful smile.
I watched as the boat docked in the slip next to mine. I
could not take my eyes off Emily. I wanted to get to know her and make her a
masturbation muse. Emily was captaining a borrowed boat for that weekend’s
ladies regatta. She and her crew sailed about four hours down the bay to get to
our harbor. A cheery and friendly woman, she wore these wire-framed eyeglasses
when not in her sunglasses. The eye wear accentuated the pleasant features of
her face.
I made sure I was down at the dock the next afternoon when
the girls brought the boat back from the day’s races. I wanted to check out
Emily and the other gals she had on board. When they returned, my masturbatory
senses were not disappointed. Emily had discarded the white shorts from the
previous evening and was in full bikini mode. It wasn’t a string bikini, but
close. An orange and white number, the fabric looked like an orange-swirl ice
cream. I tried to pretend I wasn’t looking but I’m sure I was obvious. The
other girls all wore shorts and shirts and deck shoes. Emily, as the
helmsperson, could get away with such skimpy attire and flip flops. I felt my
cock jump as her beautiful feet and leg landed on the dock a few feet from me.
I realized I had to masturbate to this lovely view right
then and there, and I had the perfect opportunity to do so. The cabin windows
of my boat were tinted enough that on a bright day it was difficult, if not
impossible, to see inside. I sauntered down the hatch, pretending I was doing
chores. Instead, I quickly stripped and positioned myself on the main cabin
berth to get a view out the port window of the girls next door. Emily, running
around in her orange-swirl bikini and flip flops, got most of my attention. My
cock was rock hard as I moved my hand up and down. I gazed up and down Emily’s
nice, long legs. Looking up past her pretty ass and sexy back, I fantasized
about fucking this MILF from behind. I gripped my penis harder, pumping for
maximum pleasure. Emily turned around, showing off her tight abs and the front
of her sexy legs. She appeared to smile right at me, and that almost caused me
to spurt right there.
I then came to the realization that although the girls could
not see me through the port window, the main hatch offered a slightly better-lit
view of the inside of my cabin. If someone were to walk down the dock past my
boat, they might be able to catch a glimpse of my naked self in full
masturbatory enjoyment. It would be only a dark, quick glimpse but knowing this
made this session so much more exciting. One of the girls could have jumped up
on the dock to borrow my hose and could look inside and see me making love to
my cock while taking in their beauty. This realization made the pleasure
coursing through my member that much more intense. My heart beat faster. Emily
and crew folded sail and coiled lines. Emily kept walking up and down the dock
to her truck and back. Each time, I could hear her cheap flip-flops slapping
against her pretty feet. That’s a sound I love, and masturbating to this view
of her walking in her bikini while hearing that thwack, thwack was incredible.
I wanted to scream out loud how much I love to masturbate and how much I was
enjoying Emily. I kept my mouth shut so I would not be discovered but the urge
was almost too great. After about 20 minutes, the girls had the boat all
cleaned up. Emily had hosed the vessel down and the water droplets clung to her
tanned and toned body. I realized she would be leaving for the evening, and I
pumped hard and shot off an incredible load of semen while Emily coiled the
hose. It was a beautiful orgasmic end to a wonderfully voyeuristic masturbation
session.
I was drenched in sweat from being below for so long. I sat
there for a minute, covered in my own sperm, gathering my breath. There was a
dinner that night for the sailors. I had not planned to attend, but I made up
my mind right there that I had to go. I cleaned up the semen, put my clothes
back on and raced home. It didn’t take much to convince Cheryl to go to the dinner;
she didn’t want to cook that night, anyway. We went down to the clubhouse at
the appointed time. There was Emily; hair down, lovely smile, sun-kissed body
in a tight t-shirt, shorts and those cheap flip flops. I drank in the view and
thought about how I had masturbated to her just a couple of hours before.
I chatted-up Emily over the course of the event and we
became very friendly. She had a husband and two young daughters who were also
at the dinner. We talked about boats and sailing and family. I enjoyed her
pretty smile, and I kept stealing glances down her sex legs to those pretty
feet. Hearing that thwack, thwack when she walked in those flip-flops reminded
me how much of a masturbator I am; of how I spent a chunk of the afternoon
naked on my boat, spying on her in her little bikini. I felt the dopamine rush
a masturbator feels when he even thinks about wanking his cock.
The next day was Sunday, and Emily and the girls would leave
the race course and head right home after the last race. That meant I had to
get down to the boat early to see them off. Of course, I got there before any
of them and hid inside my boat, naked with a ready cock. All of the girls
looked cute, but Emily was the best. She donned her orange-swirl bikini, and
this time eschewed the flip-flops. Masturbating to her pretty barefoot image
was so nice. I spurted my jizz just as they were pulling out of the slip. I
don’t think they even knew I was on the boat.
I didn’t see Emily again for the
rest of the year but I could not get her out of my masturbatory mind. I kept
playing those images of her back again and again, pumping my cock to Emily on a
weekly, if not daily basis. By the middle of winter, I still thought about
Emily but my masturbation to her was less frequent. The images were getting too
hazy and the thrill was less, until January when she came to our banquet to
collect her trophy for winning the regatta.
All of the masturbation pleasure and my masturbation crush on Emily came
rushing back. When I got home from the banquet, I masturbated to her until I
fell asleep. I continued to masturbate to her for months afterward.
Over the
years, Emily and I have remained friendly. I only see her a couple of times per
year, but each time I drink in enough of her beauty for masturbation fodder
that it lasts me for months. I’ve also managed to either take pictures of her
or get pictures of her that I use for my masturbation. She is such a good muse.
Now just turned 58-years-old, Emily maintains that outdoorsy beauty and slender body I
became enamored with when I first saw her. In the intervening years, she got
divorced and remarried. Her girls are grown. She and Pete own a beautiful boat
that they sail up and down the bay. Sometimes they stop in our harbor and
socialize with our crowd, even going to dinner with Cheryl and I.
As I gaze at Emily, I marvel at her cuteness and think of my
masturbation infatuation with her. I always can’t wait until I can get
somewhere to make love to my own cock over her. Masturbatory Love.
