Date: Thu, 23 Oct 2014 07:10:57 -0700
From: ian wylde <wyldenights@yahoo.com>
Subject: The Erotic Adventures of Jack, the Omni-Sexual Detective, Installment 3

The obligatory disclaimer: This is a work of fiction.  As such, all
characters are figments of the author's twisted and deliciously dirty mind.
Any resemblance to actual people is strictly an unintentional coincidence.
If you are under eighteen or are offended by things of a decidedly sexual
nature, you shouldn"t be reading this.  For those under eighteen,
experience has taught me, as it will teach you, that life will mess with
your mind enough after you reach adulthood.  You really don't need a head
start.

Now, without further delay, back to the story!
                           6

                        Outside

As I said earlier, Zebulon sat in the middle of a chewed asphalt parking
lot.  A single street light illuminated the corner and a smaller, dimmer
lamp above the purple door showed where to enter.  Beyond that, it was
pretty damned dark, particularly in this one section, furthest from the
street near the nine-foot high wooden fence at the back, where sat a beat
up old picnic bench.  I stumbled toward it.

Time to take stock: I was at an adult bookstore late at night, wearing cum
fuck me pants, with an enormous erection sticking out for the whole world
(which at the moment consisted of fifteen or sixteen cars in the lot) to
see.  I'd recently had a large dick in my mouth, and I had come obscenely
close to committing the cardinal safe sex sin: unprotected sex with a total
stranger (or two, or twenty).

On the upside, my anal virginity (Izzy's Mom not-withstanding) remained
(for the moment) intact.  On the downside, I was alone in the dark with the
fuck me clothing and the erection and the delicious tingling in my mouth
and throat, and infused with enough sexual energy to light Manhattan.

I sat on the table part of the bench and adjusted my package (which had
thankfully subsided to the point where it seemed no longer about to explode
through the front of my pants) and tried to pull my tee shirt downward to
cover things as best I could.  This (of course) brought my hand into
contact with the pulsating, throbbing, tingling, blood-pumping,
mushroom-headed near-cause of my almost gang bang, which helped matters not
in the least, so I tried to focus on something else.

                            ??

If I seem a bit preoccupied with the notion of being fucked by several men,
it is only because as I write this part of my story (a number of years
later), I happen to be sitting on a pillow as a result of the fact that
last night I was the focus of just such a gang bang and my anus is still
quite tender.  Four men and four delightfully hard cocks found their
lecherous way into my warm and wet mouth and eventually up my tight and
willing ass.

It began as a simple photo shoot (although, given the overtly sexual nature
of the sessions, they're rarely simple), with me starting out in a
skin-tight one-piece black mini-skirt, black lace thigh-highs attached to
black silk garters over red crotchless panties and with a rather large red
butt-plug as a prop.  Ordinarily, I work with a photographer and perhaps
one lighting assistant, but last night for some reason I find myself unable
and unwilling to complain about, there were four in attendance.

It is possible the additional spectators came as a result of the fact I had
previously allowed the photographer to fuck my brains virtually out during
each of the first three photo sessions I'd done with him, but this is of
course complete speculation and since I enjoyed myself immensely, I see no
point in further investigation into his motives.  Let us move on to more
important things, such as me getting gang banged.

In any event, and in the course of the photo shoot, I found myself rock
hard, half naked and well-lubricated, with a butt-plug up my ass and
surrounded by four gorgeous erections.  What else could I do but remove the
prop, bend over, and invite them to come inside?

They didn't physically cum inside me, of course; that would have been
deeply dangerous, but...  You get the idea.

And for those who don't, I'll just say this: they didn't cum inside me, but
they did cum all over the outside of my body.

Izzy's Mom would have been green with envy.

I found the entire episode intensely satisfying, but as anyone who's ever
been penetrated in such a fashion can attest, it leaves a certain, shall we
say, afterglow that is impossible to ignore.  And so as I sit here
squirming while I type, my well-fucked posterior keeps sending signals of a
distracting nature to my memory circuits, which insert themselves into this
narrative of the very first time I experienced the act of penile
penetration.

I hope you can forgive me.

                           ??

Getting back to the night in question, the cigarette pack in my shirt
pocket seemed to be winking at me and I smiled, remembering what was in
there.  I flipped it open and pulled out the half-joint and my lighter,
already tasting the skunkiness and feeling the warm glow.

Darkness is a blanket wrapped around you, keeping you safe and hidden.
Lighting a joint in the darkness is like turning on a searchlight and
aiming it at those horny men sitting alone in the dark in their cars with
their nasty thoughts.  I suppose I could have been more conspicuous had I
thought about it, but perhaps not.  Maybe a bit of neon blinking out an
invitation to just come and Do Me, Do Me, Do Me...  But of course, I
remained oblivious to such things, my mind being filled with lust and hard
cocks covered in my own saliva, and repeated fantasy (up to that point)
fuckings of my ass, and the doobage I was about to smoke.

A medium-sized camper sat in the shadows about twenty-five feet from my
picnic table.  Its front windows pointed toward me, covered with what in
daylight hours would be a sun screen, hiding whatever might be in there.
Light showed from inside as the passenger door opened and then winked out
as it closed again.  A man stood there bathed in shadow, motionless,
looking in my direction.  I should have left well enough alone but of
course, I didn't.

I took a deep hit off the joint and leaned back onto the table with one
hand supporting me from behind.  The movement pulled the tail of my shirt
upward and a languid stretch of my legs finished the job.  If the guy at
the camper didn't take the hint, he was brain dead.

As if proving cerebral functionality, the shadowy figure headed my way,
looking around to see if anyone was watching.
 No one was – except perhaps whoever may or may not have been inside the
three other nearby cars pointed toward me.  I took another hit off the
joint, spreading my legs ever-so slightly, and watched him approach.

He didn't say a word as he halted his forward progress about six inches
from my out-stretched limbs.  He stood there slowly letting his eyes work
up my body, pausing about halfway to stare at the focus of my arousal.  I –
casual as could be – took another hit off the joint and spread my legs a
bit more.  He smiled, like a hungry manimal who's just found his late night
snack, and looked me in the eye.  I held out the joint to him and he took
it.

Passing it back to me, he nonchalantly as you please dropped his hand into
my lap.  I thought this quite a nice thing for him to do.  He proceeded
with this maneuver by sliding that hand across the outline of my hardon and
down onto my tingling scrotum.  He rummaged around for a bit until I once
again offered up the joint after taking a deep hit.

I blew out the tasty smoke and stretched like a feline, thoroughly enjoying
the sensations my body transmitted to my Medulla Oblongata.  Animal brain
in overdrive, I set about adjusting my clothing.

Somehow, the long tee shirt I'd been using in a vain attempt to cover
things had lifted upward, revealing quite a lot.  Not sure how that
happened.  I rectified the situation by revealing a good portion more of my
flat belly and the waistband of my sweats.  I surveyed my newest fashion
statement and judged it to be adequate for the circumstances, but needed a
second opinion.  Luckily, I had one right there.

"What do you think?" I asked.

"I think I want to fuck your brains out," he replied, offering to return
what little remained of the joint.

I declined both.  "Pleasant thought," I said.  "But it's not going to
happen."

"That's disappointing."

"It's not a total loss, though."

"Is that right?"

"Yes," I replied.  "I'll be happy to give you a sloppy wet
 blowjob."

                            ??

As I said before, Izzy's Mom gave me one of those on the eighteenth
anniversary of my birth.  But it wasn't until three years later, on a
Friday night three weeks before the Friday night I gave my first sloppy wet
blowjob that she demonstrated to me exactly what one was.

"To give a good blowjob," she began, "you need three things: a hard cock,
which you so delightfully have," she continued, planting a warm kiss on my
tip.

We were in her livingroom with me in one of the overstuffed chairs and
Izzy's Mom on her knees between my legs.  Izzy was at his father's.  She
wore no shirt; I wore no pants; together we made one fully-clothed human
being.

I had nonchalantly asked her about it (cocksucking), knowing full-well I
intended to put her information into practice just as soon as I turned
twenty-one.  She did not know this, however.  I eventually told her about
my more-than passing interest in the art, but on that glorious night, she
thought the question to be mere curiosity, and so explained it as one who
truly enjoys what they do, rather than as a teacher trying to instruct her
willing student.

"You need a nice wet mouth," she proceeded, sliding hers over my head and
proving it was indeed nice and wet.  She slurped it up and down to about
the middle of my shaft, sucking and drawing saliva up from her throat,
taking her time, warming up to something I knew would be akin to a
religious experience.

"And you need to love what you do."

                            ??

Izzy's Mom loved what she did, both in her personal relationship with me
(and presumably others) and with her website.  This, I think, is what made
her the most popular of the seven women involved.

Ninety-nine point nine-nine-nine percent of all the non-lesbian/all-girl
and/or sado-masochistic porn I've ever seen (and with Izzy as my friend,
I've seen a lot), regardless of subject matter, follows the same exact
pattern: suckee, suckee, suckee, fuckee, fuckee, fuckee, guy pulls out,
money shot all over the other person's face...or ass, or other
strategically-placed cumshot, but more often than not, it's right straight
into—and all over—the kisser.  The subject could be straight sex,
anal sex, tranny sex, any sex, but the format is always the same.

I think it was Noel Coward or one of those other ever-so witty writers from
the Nineteen-Thirties and Forties, who said they saw nothing overly
objectionable about pornography (and back then it was all a very big no-no
that could result in a prolonged prison sentence), except for the fact that
it was exceedingly dull.

All fiction is fantasy, and in order for the fantasy to work, a certain
suspension of disbelief is required.  With the obligatory cum facial,
however, more often than not, the expression on the recipient's face says
loud and clear the woman really isn't into it: her eyes and lips are
squeezed tight, her posture and bearing looks like she's about to run away
while lying down, and she generally looks as if she'd rather be calculating
her taxes.  But the money shot is expected, it's the de rigueur ending, and
so the recipient steels herself for the inevitable, and right there is
where the suspension of disbelief falls apart.

And since almost every porno ends in the same way, there is no surprise,
nothing unexpected, nothing to separate one movie – one sex scene –
from another.  Pornography is kind of like comedy would be if every comedy
ever made ended with a pie in the face.

Okay, granted, most viewers of porn don't give a shit, but I do.  I love
variety (which I suppose has something to do with my choice of sexual
partners).  I also love women.  I love seeing women in the throes of
pleasure (especially if I've given it to them).  Nothing turns me on more
than a woman who's enjoying the hell out of herself, and so when I see
women (or trannies or whomever) screwing up their faces to receive the
money shot they do not enjoy, it bursts my voyeuristic bubble.

Izzy's Mom, on the other hand, absolutely loved having cum shot all over
her face.  For her, it was a transcendent experience capable of bringing
her to orgasm without any manual stimulation whatsoever.

Seeing it, seeing the delight in her eyes, the hungry, horny, deliciously
loving it smile on her face, damn-near has the same effect on me: it almost
makes me cum just watching.  And that, my friends, makes all the difference
in the world.

                             ??

The legendary George Burns was asked shortly before his one hundredth (and
final) birthday to explain his longevity.  After first tossing off the
joke, "whiskey and cigars," he said the secret was waking up every morning
to do something you love.

Love's physical manifestation is affection, and the ultimate form of
affection is sex, if you do it right.  When you're affectionate with
someone, you take joy out of their presence, and you give them pleasure in
return, be it a hug or a warm handshake or a playful swat on the behind.
Who doesn't like a good hug?  Or a nice spanking...?

There are essentially two ways to have sex with someone: fucking and
lovemaking.  The mechanics are the same and both offer infinite variety,
but the difference lies in one's attitude.  Fucking is about getting off,
which is nice, but if you're in it just to get off, then you're only in it
for yourself.  Which is fine, if that's what you want; everybody needs a
little self-gratification from time to time.  I've always thought that men
had it best in that even bad sex is as good as masturbation, as long as you
cum.

For a woman, however, bad sex is pretty much just bad sex and the odds of
orgasm are diminished at best.  But if you approach it with affection and
love, two things are going to happen: she's going to get off, and then
she's going to absolutely fuck your brains out, which I've always found
highly entertaining.

When you love something (or someone) your heart is in it, and if your heart
is in it, the rest of your body will follow.  With love, there isn't a
whole lot you can't do; without it, there isn't a whole lot worth doing.

                           7

               In And Out (and In And Out)

Inside of the camper, dimly lit by a small lamp above the stove, we stood
side by side at the back, looking down at the bed, neither of us saying a
word.  After a few moments of somewhat uncomfortable silence, he placed his
hand at the base of my neck and began sliding it downward until it came to
a rest on my behind.  He gave me a squeeze and with gentle persuasion
pushed me onto the mattress.  I moved to the back wall to give him room,
but he did not immediately take advantage.  Looking down at me, he
unbuckled, unzipped and then dropped his pants, kicking them off his
ankles, and stood there slowly stroking himself.

I lay there in my skin-tight pants, thrusting my hips forward, my cock once
again throbbing like, well, quite a bit like a throbbing cock, actually.  I
offered just as big an invite as I possibly could, but he seemed interested
in a different part of my anatomy.

"Roll over," he said softly.

I hesitated.  "We're not going to do what I think you want to do," I said.

"I know," he replied.  "But does that mean we can't play?"

Instead of answering, I smiled and rolled over onto my belly.  The pressure
on my erection proved to be a bit much, however, so I arched my hips,
sticking my butt into the air.

He seemed to endorse the maneuver.

He demonstrated this by gently playing his hand along the contours of my
bottom.  "You have a very nice ass," he said, giving it a tender squeeze
and slipping his fingers between my cheeks.  It felt wonderful.

"And you have a very nice cock," I said, and he did.  It wasn't near as
large as the one I'd so recently had in my mouth – perhaps six inches
long and maybe one-and-a-half in diameter; just a tad bigger than the toy
Izzy's Mom had used on me.  It started me thinking.

But first things first: I scrunched closer to the edge of the bed (and what
waited there for me between his legs) and began to administer a blowjob
such as I hoped he'd never had before.  Slurping and sucking, sliding and
swallowing, bobbing my head up and down, pulling his probe in and out,
swirling my tongue from side to side, I created a geometric series of oral
shapes the like of which Pythagoras himself would have been astounded; a
polygon, an isosceles triangle, a veritable dodecahedron of cocksucking.  I
twisted and turned in every cardinal direction: north, south, east, west,
south-southwest, northeast, three points to starboard and another five to
port.  I could have travelled the world, circled the globe, circumnavigated
the planet Earth with my mouth on his yummy erection, but he had other
things in mind.

He pulled out with a pop like a champagne cork, and then took hold of my
waistband and began pulling downward.  The cool night air on my naked flesh
sent jolts of electricity up my spine, through my head (bypassing my
previously busy mouth) and then made a bee-line to my testicles.  He
grasped my hips and pulled me upward.

With one continuous stroke, he slid his tongue from my balls to my perineum
to my anus.  He probed there with the wet oral appendage for quite some
time, and I happily let him, sticking my butt out and up in order to
provide maximum ease of access.  By and by, the muscle began to relax and
open.  He inserted a finger.  Then he inserted two.  He worked his digits
in and out slowly, opening me still further.

We had done all of this without sound, save my own moaning (and the
preceding sucking noises).  Finally, he broke his silence.

"I have a condom."

"Fuck me," I said, throwing caution to the wind and basic intelligence out
the damned window.  Hey...At least it was safe sex.

                           ??

Rationalization, thy name is Jack...  Or maybe it's Jack's Dick...  Either
way works.

                            ??

He produced a condom from some unknown location (probably a shelf) and
fumbled it, dropping the package onto the bed at my side.  I took pity on
the poor man and proceeded to bite it open.  He seemed content to allow me
to take over, and so I did, removing the rubbery sheath and slipping it
onto his engorged member.  For good measure, I ensured its placement and
fit with my once again wet mouth, sliding his now latex-tasting organ in
just as far as it would go, the condom's reservoir tickling the back of my
throat in a most amusing manner.

This seemed all fine and good, but his rock hardness had a previous
engagement with a different orifice.  Reservations had been made, the
ma๎tre de had been called, the bus boy had placed the water, bread and a
chilled dish of butter slices (calling to mind a certain scene from Last
Tango in Paris – although the thought of a naked Marlon Brando is best
avoided at all costs) onto the table, and the chef busied himself in the
kitchen with all manner of sensual delights.

I wanted it.  Truth be told (or at least the kind of truth seen through the
horny filter of a libido rushing toward warp speed), I needed it, needed to
be speared, to be penetrated, and so I removed him from my mouth and once
again presented my ass to him in open invitation (no RSVP required).

He crawled upon the mattress and knee-walked into position behind me;
grasping my hip with one hand, while playing his cockhead across my waiting
anus with the other.  Here it was, the moment I'd dreamed of during more
masturbatory sessions than I cared to count, even going so far as to
fantasize about it as Izzy's Mom had done her thing with fingers and
occasionally toys.  My penis hung like fresh salami in a butcher's shop
filled with blood and delight and tasty potential.

After applying a generous amount of lube to the necessary areas, he slapped
the head against my entrance a few times, rubbed it around the general
vicinity for a few moments, played with and teased it until I damn-near
told him to just get on with it, and then slowly pushed inside.  Electric
shots of pleasure pulsated outward from my ass to my pounding heart and
then swirled within my infinitely aroused brain pan.  It felt huge, hard
and outstanding.

Slow and inexorable, he slid inside until his pelvis rested against the
tingling flesh of my cheeks.  He held it there for a moment then just as
slowly pulled it all the way out again, leaving me with an odd,
empty-yet-filled feeling.  I arched my back and thrust myself towards him
like a rutting animal.  He returned the favor by pushing back inside.  The
man – my still-unknown temporary lover – wriggled his hips in a
more-or-less circular motion, as if stirring my rectal bowl, stretching my
muscular anal guard.  He paused.

"What do you want me to do?" he asked in a hoarse whisper.

"Fuck me," I replied.  "Fuck my ass."  Okay...I know...Not the most
creative or original of answers, but what can I say?  I found myself caught
up in the moment.  Linguistic legerdemain had taken the night off.  I'd
waited for this, dreamed of it during innumerable sessions of video
ass-fucking at Izzy's house, masturbated over it who-knew how many times,
but nothing could have prepared me for the raw, unbridled, carnal pleasure
of actually being pounded, of having his pelvis slap against my ass as he
slammed into me, his testicles swinging against mine with each thrust, his
fingers biting into the flesh of my hips as he filled me, probed me, fucked
me.

                           ??

In my fantasy, the act – this initial foray into gay anal sex – went
on and on, building in intensity, bringing me to the edge and then backing
off, slowing, prolonging the delicious experience until I screamed for
release: Insert Tab A into Slot B; You put Tab A in, You pull Tab A out,
You put Tab A in, and you shake it all about; You do the Hokie Pokie and
you turn yourself around; That's what it's all about.  Repeat as necessary
– or desired – or just for the fuck of it.  This, in any case, is the
theory.

The reality, however – and this I suppose is the essential nature of
reality, that despoiler of most things erect and/or wet – proved to be
somewhat different.

                           ??

I had just gotten into a smooth rhythm, meeting his thrusts with backward
motion, grinding into him as he pounded me, and I had yet to even begin
stroking myself, when all-of-a-sudden, he shuddered, pulled out, ripped the
condom from his pulsating meat thermometer and came, the hot, thick goo
spraying across my back, as if he'd squirted me with a turkey baster.

                           ??

Over the years – and I'm telling this tale quite a bit of time after the
fact – I've often wondered why I bother fantasizing.  The reality rarely
meets (let alone exceeds) the fiction.  It has a few times, and I remember
those all-too brief moments with warm fondness and furious masturbation,
but this is the exception far more often than the rule.

Ah well...  And still we try.

                            ??

I walked home (after more or less begging the man to wipe my back with a
none-too clean towel he'd scrounged from a malodorous pile on the floor of
his RV), feeling generally unsatisfied.  And yet, as I strode down the
sidewalk through the summer night, with the first rays of dawn peaking
above the horizon, I couldn't help but admit the experience had been
entertaining, enlightening, dare I say, transcendent.

Well, perhaps not.

I'd given my first blowjob (although, not to completion) and I had received
my first true fucking (I wasn't counting Izzy's Mom's amusing
machinations).  My ass felt rather delightfully worked, and my as-yet
un-milked object of soon-to-be masturbation still throbbed within my tight
pants and oozed with pre-cum.  Granted, this left a noticeable wet spot in
the general vicinity of my crotch, but with the long tee-shirt once again
pulled down into the proper position, the only one privy to this fact was
me – and I wasn't talking.

And okay, yeah, the experience hadn't been all it was cracked up to be.  It
had not matched the fantasy.  I had not been satisfied.  But it had still
been fun.

In spite of how unlike the fantasy it had been, regardless of my lack of
orgasmic release, forgetting the technically unsatisfying result, the fact
remained: my ass felt fantastic.  And like a girl who loses her virginity
amidst the blood and the pain and the ineffectual, inexperienced fumbling
in the backseat of her boyfriend's father's sedan, I knew I'd been doing
this again.

I did not, however, know that the next time would be with a lesbian.

...To Be Continued...

Dear Reader, I hope you are enjoying this story.  I truly want - in fact,
need - your input, as I am looking at this with the goal of getting it
published.  Any and all comments and/or CONSTRUCTIVE criticism would be
greatly appreciated.  Thanks for reading, and if you can spare a bit of
change, by all means support Nifty!