Date: Wed, 17 Jun 2020 19:12:11 +0000
From: "ckid2772@hotmail.com" <ckid2772@hotmail.com>
Subject: Caught Midnight Swimming

*****

Caught Midnight Swimming
By Ryan S     [ckid2772@hotmail.com]

*****

My first encounter with another guy happened in the summer between my
freshman and sophomore year in high school. The circumstances were a bit
strange, certainly not your average first experience. He was a neighbor
who caught me naked in his pool, and maybe 15 to 20 years older than me.
This is the story about that summer and in particular the night it
happened.

To start with, here is some information about me at the time in order to
help you visualize this. I was 15, turning 16 right at the end of summer.
I was about 5'7 at the time, and maybe 145 pounds. I was into sports, a
lot of different sports, and weight lifting, running, so I was really
fit. Like really in shape, I was really proud of my six pack abs at the
time, I was pretty impressed with myself honestly. I had hit puberty at
around 13 and by the time I was 15 my body was pretty defined, much more
so than others my age. It was an ego boost, not to mention my physique
made me one of the top athletes in my class. Despite that rapid
development in muscle mass, I couldn't grow a beard at all, and had
little body hair - just the beginning of some on my shins, under my arms,
and a patch right above the base of my cock - which is uncut, and at that
time measured about 6". The rest of my body was naturally hairless,
including my ass and my nuts.

Over the school year I had met my first girl friend, gone through all the
bases, including having sex for the first time, both oral and vaginal. My
limited experiences had been fun, pleasurable, but after all of that I
knew I had a stronger preference for guys than girls. I had been into
Lycra since I was 13 or 14, particularly guys in bulging speedos or
wrestling singlets. At around 14 I actually bought a shiny blue speedo
that I liked to wear under my clothes, and concealed my cock which was
hard almost all the time when I wore it. That was fun. Anyway, I wasn't
stupid so based on what I liked to jerkoff thinking about, I had a
feeling that I was at least bisexual, and my first girlfriend experiences
really helped clarify things. By the time summer was coming up I had
broke up with my girlfriend, for a number of reasons - the main thing was
I just wasn't that into it while she told me she was falling in love, and
I didn't think that was fair to her given I was totally questioning what
I really wanted.

That breakup might have been a bad plan, because I went from having an
outlet for my sexual energy to only solo action. That had been fine
before I found out what it was like to have a sexual partner, but now I
was even hornier than before. The summer time was always a mixture of
being around friends from school, sleep overs, swimming, and playing
sports... including time spent in the locker room with the other high
school guys. Some of my peers definitely caught my eye before - well,
mores o that summer than ever before given my budding sexuality. By July
or so I was literally humping my pillows and masturbating in front of
mirrors. I remember putting that blue speedo on, putting my pillow on my
bed, and watching myself hump it while my speedo clad butt flexed as I
thrust back and forth. I had a great bubble butt I thought, and still do
actually. God, I was an awful horny little monster. Eventually I found
myself doing other things - pent up sexual energy comes out, and in this
case the limited outlets I had couldn't get the desire out of me fast
enough. I was fantasizing about ways I could seduce my friends, even
thought about finding an older man at a local hotel or a cruising area I
had heard about to find someone who wanted to pleasure me. At sleep overs
with my friends I was jerking off at night while the others slept, I
wanted to unzip one of my friends pants to see his cock while he slept,
but he woke up when I poked him slightly to see if how deeply he was
sleeping. I could go on and on, maybe I'll say more about some of that
stuff another day. What's funny is I didn't really watch much porn, at
the time high speed internet wasn't common, there was no xtube or
porntube. Maybe with porn I would have been more satisfied, I don't know,
bottom line was I was insatiable, out of control!

To understand the next part, you should know about the layout of my
neighborhood. It was a suburban area, set with houses pretty close
together, with some trees between the properties. The roads of each
street ran parallel to the next, with a main street running
perpendicular, connecting those parallel streets. My parents' house had
houses on either side, and there were houses behind my house, which were
on the next parallel road over. There were a few parallel streets like
this, and I had a friend who was a couple streets over. I often walked
from my house to a friend's house, through the small wooded areas between
houses, and across a couple of these parallel streets. On the way there
was a house with a bit of a larger property, with a pool that had a fence
around the pool area.

I had walked through there many days and nights before, and I knew a
married couple lived there. I didn't know them at all, since they were a
couple streets away, and they were younger than my parents, no kids, but
I had seen them as I passed by. I went walking by that pool late at night
as I went home a number of times that summer, and I noticed the pool area
really dark, and I started thinking about how hot it would be to go
skinny dipping in that pool. I don't know why I thought this was a good
idea... but again, I was horny as hell, and looking for sexual outlets to
alleviate that. Anything could capture my imagination and make me horny,
and this idea began to become a fixation. I made a determination that I
wanted to swim nude and that was the place to do it, so I guess you might
say I started casing the place.

When I went by the house day or night, I spent some time observing. They
had a garage that fit one car, you could see in it from pretty far away
to see if a car was in there. I could see that the front had a sensor
light, but the back area did not. A number of other things, but you get
the idea. I saw the husband, I'm guessing he was in his early 30s, could
have been late 30s. At the time he seemed "old" because he was likely at
least 15 years older than me. As a youth observing an adult, he seemed
really tall to me. Realistically he was probably just over 6 feet, slim
to average build for someone in their 30s, dark hair. His wife a blond,
definitely a pretty lady - not that it mattered much to me.

Towards mid-summer I noticed late one night there was no car out front,
so at least one car was gone. All the lights off in the house. The pool
area was dark, but lit by the moonlight. Perfect opportunity. I was so
horny, I didn't hesitate much at all. The fence was wood, too high to
scale, so had to go through the gate on the side. The latch was metal,
but not very noisy as I was careful, and I slipped in. There was a
circular table with chairs, and then 5 or 6 long deck or pool chairs
positioned on the side of the pool. I stripped down and laid my clothes
on a long one, and proceeded to get into the pool. It was warm actually,
and I slipped in, my cock had been half hard at the thought, as I felt
the water enclose around my body I got rock hard. I gently whirled around
in the water, even thrusting my hips like I was fucking, I loved the free
feeling of being naked, the water flowing around me, touching my body all
over. I observed that it was really quite dark, despite the moonlight,
and I figured no one would be able to see me now that I was in the water.
I crept to the side of the pool, walking in the shallow end, where there
was a jet stream. I put my cock to the water jet, and it felt great, I
did this for a few minutes. My cock was rock hard all that time, and I
figured I had been there 10 minutes or so, and I ought to get moving. I
grabbed my cock right there in the pool and started jerking off my uncut
cock. I've rarely been as hard as that in my life, the first time I was
really adventurous about sex, and it wasn't long before I felt my orgasm
tickling my spine. Naked in that pool I started spasming, and I felt my
balls unload into the pool. I didn't bask in the afterglow much, instead
I moved quick now that I was done. I put my clothes on, just shorts and a
T-shirt, slipped on my shoes, put my socks in my pockets and jetted out
of there.

No problem. I got home and thought about what I had done, it was really
fun, I was satisfied for now, but knew I would want to do it again. And I
did, like 3 more times. It didn't really get old. Same scenario, one car
gone, looked quiet. I avoided nights when there were two cars, and
sometimes a TV on in the back room facing the pool, so no go on those
nights. I jerked off lying on the long pool deck chairs, shot my load on
the concrete around the pool. The little freak I was a the time liked the
idea of claiming that territory, shooting my juice in the pool, around
it. I wore my blue speedo over, feeling the tight Lycra suit cling to my
body was also a turn on. That pool was my little sanctuary those nights,
where I could release all that sexual energy. It was a relief to feel
satiated after those night swims.

Mid to late August I went one more time, it really wasn't different from
the other times to start. I had worn very little clothes this time,
shorts, T-shirt, shoes. No sox, and no underwear. I had snuck out of my
house, at about midnight to do the deed yet again. I left my clothes
lying on the table near the pool. I swam nude in the moonlight and it was
really warm, so I got out to enjoy being naked in the open air. I had
brought a towel, and I was laying on it, on one of the long deck chairs
and masturbating. Then from the darkness by the pool fence, near the
house a voice said, "what do you think you're doing?"

I froze in sheer panic, like a deer in the headlights, with my cock in my
hand. After a moment, I covered my hard cock with my towel, and squinted
into the dark. A figure moving around the fence line to the gate, I was
freaking out inside, but unable to move pretty much at all, nowhere to
run since there was only one gate and I was naked with my clothes on the
table. He rattled the gate latch and entered into the moonlight. That had
been the problem, the back door to the house, angled such that the moon
light didn't touch there, and I didn't hear the sliding door open I
guess. I don't know. I could make out the silhouette of a man in the dark
as he approached me, still lying on the deck chair covering up as best I
could, it was obviously the neighbor though I couldn't see his features
at all.

I honestly don't remember exactly what he said when he approached and
started talking. It was a questioning complete with reprimand, like my
parents might say to me. What are you doing here? I think he asked if I
was naked under the towel there and who I thought I was. I remember him
saying it was trespassing. Then what caught my attention and snapped me
out of my stupor was when he asked, "You live around here right? You
parents probably don't know about this I'm guessing."

At this point I had that awful feeling in the pit of my stomach, you
know, when you're in big trouble. And I stammered something like "I'm
just visiting a friend, I saw the pool and wanted to swim. I didn't have
a swimsuit, I'm really sorry." He told me, "I think I've seen you around
here before, admit it, you live around here, tell the truth." So, I came
clean and I basically begged him not to tell my parents, I'll never do it
again. He said "thanks for being honest" and went on to tell me how he
had cameras around the place, and he knew I had been there before. I was
mortified, he didn't say he had seen all the jerking off I had been
doing, but I figure even if the cameras weren't night vision he must have
seen it in the moonlight. At the time cameras at homes like this were
really uncommon, none of my friends' houses had cameras. I hadn't thought
of that at all. In fact, today I wonder if he even actually had cameras,
or just saw me once or twice, and determined his own master plan.

This conversation was quick, I'm sure, but it seemed like forever talking
to this shadow figure in the night. I couldn't really even see his face,
the way the moonlight was put the shadow on his front, while I was basked
in moonlight, so exposed and vulnerable. He told me I was lucky his wife
didn't catch me, she was away for the night, she doesn't check the tapes,
he wasn't sure if he should tell anyone about my trespasses or not. I was
telling him again I was sorry, and I asked him if I could get dressed and
go. At that point he said, "hold on, hold on. Look, I've got you on tape
here, this could be a big problem for you... but I don't really want to
see you get into trouble. Maybe you can do some stuff for me. What do you
think?" The pit I had in my stomach unfurled somewhat at this glimmer of
hope, I felt an immediate sense of relief, like "there is a way out of
this". Doing some chores for this guy, whatever, no problem, and I said
something like "Oh, that would be great"

He chats a bit, putting me more at ease as he goes through some
chit-chat. "So, you like the pool? It's nice out here tonight don't you
think?" That kind of thing. Then he asks if my parents are expecting me
home, and I say I really ought to go but at least their asleep, I tell
him I sneak out sometimes. At that point, he says basically "Ok, so
here's the deal. You're going to close your eyes for a little bit, be
quiet, and you're not going to tell anyone about tonight at all. You know
I've got you on tape here multiple times, so it would be bad for you to
tell anyone you were here. And I won't if you won't. You have to give me
your word you won't say anything, and I promise to not say anything
either" I was a little confused by the detail of what he was saying, the
close your eyes bit was confusing in particular. It was an easy decision
to agree though, what choice did I have, so I said okay sure. I even
thanked him, I was relieved this looked to be working out somehow. He
asked me again to promise, and I said absolutely 100%, I promise.

The shadow in the dark says, "ok great! I want you to just lie back,
relax and close your eyes, and keep them closed." I followed his
directions and lay back in the deck chair, and I heard him walk next to
me. He moved the back of the long chair and sort of rattled it, and it
collapsed such that the deck chair was totally flat. He told me that I
should keep my eyes closed, he was going to give me a bit of a massage. I
don't recall exactly what my thinking was at that moment, but nothing
coherent. His hands went onto my body, rubbing my shoulders, my pecs,
then down to my calves. My genitals had been covered by the towel, as he
massaged he gently brushed back the corner of the towel, and I knew my
cock and balls were exposed now to the now cooling night air.

My mind was racing, the surprise of getting a massage from this guy who
caught me, totally butt naked in front of him, but I was enjoying the
massage he was giving at the same time. His hands worked their way up to
my quads, then he moved up and massaged my abdominals, as he got to that
area the massage became more of a light caress, and he worked down lower
and lower, his finger tips touching into my pubic hair above my cock. My
breath caught a bit, I realized I was holding my breath, I forced myself
to breathe and relax. I now figure he was watching my reaction, to see
just how far he could go, his fingers stroking through my light pubic
hair, the base of my penis. I felt my penis stiffening, coming alive. I
could feel my cock twitching and starting to go from hanging between my
legs to growing, moving to the side, he touched it a bit with his finger
tips as it stiffened, and then up it went, pointing up as it got hard. He
must have taken this as a blessing to go further, and I didn't feel the
need to object. In any case, we had already made a deal that I needed to
keep my eyes closed and be quiet so he wouldn't tell anyone about my
trespassing. As my cock was coming alive he moved his hands down and
started fondling my balls. I was caught between shock of what was
happening and enjoying the pleasure of being physically touched by
someone else, hadn't experienced that in months. It was kind of dream
like.

"Keep your eyes closed" the man's voice said. I peaked a little bit,
opening my eyes ever so slightly, but I was lying back anyway, so only
could see up, he was just a shadow above me. He might have had his cock
out by then, I really don't know for sure. I closed my eyes again, and
felt as one hand pulled slightly on my balls, the other one moved to my
cock. He grabbed it lightly, and started a light stroke, more of a caress
of my cock. Then he grabbed more tightly, I think maybe he realized I was
uncut at that point, the foreskin allows a good stroke with no lube, and
he started doing it with a tight gip, it felt good, and at this point I
was still startled but really enjoying the pleasure. He didn't stroke me
long like that, maybe a minute, then his hands moved around again,
massaging while feeling me up all over. I remained totally hard, my cock
standing straight up along my stomach, I could feel it lying there as he
massaged. Then he said "going to flip you over" and he helped me sort of
roll over while lying on the long deck chair. My hard cock didn't make
the maneuver easy, I had to grab it and position it up as I lay down on
my stomach now, the deck chair had those sort of plastic straps that
support your body, so at least it gave a little as I lay there on my
towel.

I was like putty in his hands now, as he massaged my shoulders. Similar
routine as when he did the front, working the upper body first,
shoulders, neck. Then down to feet, which felt great, and my calves. Then
up to my mid back, worked my spine - going up and down my spinal cord, he
used his knuckle for that, I felt tingles up and down my spine. He was
moving pretty quick now, maybe knowing I couldn't be out there forever. I
wasn't thinking much about anything at this point, other than the
massaging, and my cock still being really hard, pinned down underneath my
body. My mind was relaxed I was now patiently waiting for what he might
do next sexually to me.

His hands moved up my legs to my hamstrings, and then he started
massaging my butt, and then he grabbed each leg by my calves and spread
my legs a bit. His hand slipped up between my now expose balls and he
fondled those. Then I felt one hand reach under my pelvis and he sort of
manipulated me with his other hand to get me to lift my hips, I could
kind of feel how he wanted me to position, so it wasn't too awkward as I
followed his wordless guidance. In this position, hips slightly lifted,
my face on the deck chair to the side, my cock was free, he fondled my
testicles with one hand, and with the other he reached between my legs
gently grabbed and stroked my penis. He pulled my cock such that it
pointed downwards, and I was so hard I had to sort of move my hips
further up, because my dick wasn't that flexible in that state of
erection. I was spread out enough such that I could feel the air against
my exposed anus.

I think he was sort of straddling the long deck chair, I could feel his
legs touching mine a bit while he stood like that, then I felt him sit
down on the chair behind me. And he released my balls with his one hand,
still pulling at my cock with the other. Then I felt his breath on my
exposed my hole. I bet he was smelling to see how clean I was, he was
probably sniffing, who knows. I must have passed the test because it
wasn't long before I felt him licking, sort of tentatively a first, then
all around my hole and my balls. My god, I was in shock again, no one had
ever done that to me before. It felt really good, and I started to moan
softly, more like a whimper, from the pleasure. He stopped for a moment
and whispered, "Try to stay quiet and relax", he stopped stroking my cock
at this point too, I had been feeling the need to cum right about then so
good move on his part. He put both hands on my glutes, and he spread my
cheeks apart. Then I felt him bury his whole face in between my cheeks, I
could feel his nose in my crack, and him licking, poking at my tight
hole, until I could feel his tongue going in and out. It went pretty
deep. At this point in my life I didn't know anything about my own ass,
so I wouldn't say I was totally opened up for him, but he managed to get
his tongue in there pretty good. It felt really deep anyway, and it felt
ridiculously good.

At this point, he's moaning slightly as he's doing this, he's taking his
face away from my ass and coming up for air once in awhile. As he comes
up for air he's whispering, more to himself than to me I'm sure, saying
"yeah" and "fuck, yeah" he definitely took one hand off my butt, and I
figure he was masturbating because he was kind of vibrating on the deck
chair behind me and breathing heavily as he's licking my ass like there
was no tomorrow. I feel him tense up and moans pushing his tongue deep in
my hole deep, it sounded like a deep satisfied sigh, him exhaling through
his nose which is buried into my crack. Hard to describe, but you get the
idea I hope. He definitely shot his load at that point, and he takes his
face from my ass and is sort of panting, breathing heavily. He
recuperates for a little bit, no more than a minute. I'm still in the
position with my hips raised off the deck chair I'm lying on, breathing
deeply as well, cock rigid, eyes closed face to the side still. I wanted
more, maybe he sensed that.

He reaches between my legs again with one hand, grabs my cock once more
and starts stroking it again. I can feel he has his hand positioned such
that his thumb is towards my balls and he's bending my cock down again,
and now I'm moaning, and he doesn't bother to hush me at this point.
Maybe he knew I was being as quiet as I could be. He continues to milk my
cock, pulling at it, and he put his tongue back up my ass, penetrating me
with it. And I have that feeling in my stomach, not dissimilar than the
knot of fear I felt when he caught me earlier, and it builds as he's
licking my hole and milking my cock straight down. That tightness in my
belly has my whole body trembling, my cock is starting to get stiffer as
I get closer and this only increases the tightness of his grip and he's
tugging at a steady but quick pace.

He stops bending my dick down and instead let's it pop up to it's natural
position. He changes his grip so his thumb is towards the tip of my cock,
and he's stroking it fast with a hard grip, faster and faster. His tongue
somehow seems to go deeper inside me. My body stiffens and then I feel
every ounce of that tightness channeled through my cock, it's like a
convulsion as I moan and I feel myself shooting. The first spasm felt
like an explosion, I gasped a little when it happened, then I could
practically feel the cum gushing out, then shot, and another. Probably 5
or 6 spasms before I was fully empty. I'm sure I was shooting ropes of
cum. As the convulsions relented I collapsed down, my hips flattening
out, which kind of pulled my butt away form his face. His one hand was
beneath me clutching my cock. He released his grip and somehow was able
to get his arm from beneath me.

Detail at that point is difficult to recall exactly. I was lying on my
stomach still, eyes closed, totally spent and my cock softening. He was
sitting on one side of the pool chair, next to me. Slowly stroking my
lower back and by butt, down my legs. Could have been 5 minutes could
have been an hour for as far as I was aware. Eventually he says something
like "Don't worry, I won't tell anybody you were sneaking in here. But if
my wife were to catch you it might be a problem, so you need to stay out
of here. You had better get going, your clothes are on the table over
there." I sort of snapped out of the moment, and realized again that I
was naked at some guy's house, and I was definitely out later than I
ought to be. So, I grabbed my stuff and put on my clothes, occasionally
glancing as my neighbor was watching me from where he sat, still a shadow
in the night. The last thing he said to me as I started to exit the pool
area was "Remember your promise. And don't forget that I have you on
camera here multiple times, so if you were to say anything about our
deal, I would just show them the tapes of all the times you came here.
Nobody would believe you, I can edit the tape of tonight if I had to." He
picked up something and approached me, it was my towel, which he handed
to me. And off I went.

I scampered back through the side lots of the houses and snuck back into
my house with no problem. It was late but I remember it not being as late
as I expected, though I don't recall what time. I had some of my own cum
on me, but no chance to take a shower as it would have woken up my
parents, so I got right into bed. I lay there thinking about what had
happened, I was still turned on and my cock started to get hard again and
I took care of that, shooting another load, surprisingly large
considering I had just cum like 15 minutes before. After that I fell
right to sleep, dare I say that I was totally pleased with myself. I knew
I would want more, especially now that my little haven was off limits.
That was my only regret.

I never went back to the pool again, though I sometimes saw him while I
was walking back and forth to my friend's. He never seemed to notice me
as I walked by, it could be he didn't recognize me from his video camera
or the dark night encounter. Maybe he just didn't want to draw any
further attention, best to leave it forgotten. I'd like to think he would
have wanted to do more, but alas, within a year I saw his wife with a
baby stroller. I think he took the opportunity when he could and it was
to risky after that. That night was one of the best sexual experiences I
ever had, it's still something I fantasize about. I love a good dark room
or late night encounter to this day. And eventually I did find another
older guy who was willing to service me in similar ways and more. A story
for another day perhaps.

*****

/END