Date: Fri, 13 Apr 2001 23:34:48 -0700 (PDT)
From: Juliette Messina <picummings@yahoo.com>
Subject: Pain & Pleasure: My First Night with Jack

I'd been tied up before, but never like this.  Never
for so long, or in so much pain.  I'd hoped that I'd
pass out from the pain, but that didn't happen.  My
body seemed to be on fire: every muscle hurt, but I
didn't pass out.

I'd come here the night before to turn a trick.  The
guy who picked me up had said he liked it kinky, and
that was cool.  I'd done kinky before.  He told me he
wanted to fuck me, and that was cool, too.  I'd been
fucked before.  What was especially cool was the
money.  He told me that if I "endured" the night, he'd
give me $500.  That was more money than I'd ever seen
as one time.  To get it I'd have to be totally
submissive and do whatever he wanted: no questions; no
arguments.  Some of it would hurt, but there'd be no
danger.

For $500 from one trick, I figured I could stand
anything.  And, then, I sort of liked this guy.  I
mean he was a little weird, a little intense, but I'd
done a lot weirder.  He seemed real straight-forward,
like he wasn't pulling any punches.  He wanted me to
know what I was in for.  The $500 wasn't going to be a
walk in the park, but, hey, six hours and it'd be
done.  I could deal with this, and I could really use
the money.

When we got to Jack's house, he took me downstairs to
the basement and told me to strip.  Then he left,
locking the door behind him.  Okay, no foreplay, I
thought, right to business.  I took off everything and
sat on a long table in the middle of the room, waiting
for him to get back.

The room was pretty scary, but I figured it was set up
that way: he wanted me scared.  There was stuff you'd
expect to see in an old dungeon: iron manicles,
handcuffs, ropes, whips, stuff like that.  There was
an 8-foot cross (in the shape of an X) leaning against
one wall, with manacles attached to each end.  This
was either pretty funny, or pretty scary, and I wasn't
sure which, so I was scared, wondering if I'd made a
mistake.

When Jack got back, he told me to lie down on the
table on my back, and tied my arms and ankles to the
four corners.  Then he went and got a razor and some
shaving cream from somewhere, and set them on the
table next to my butt.  He told me he was going to
shave my dick, balls, ass, legs, everything but my
head, and waited for me to respond.  I thought about
the money.  "Yes, sir," I replied, sort of
uncertainly.

Shaking the can, he squirted out the shaving cream and
spread it all over my dick and balls, squeezing my
balls as he did it.  I gasped, I guess, because he
looked up at me and smiled sort of threateningly.
Then he started shaving.

I'd just turned 18 a couple of months before, but I
guess I looked younger.  I was sort of a late bloomer,
which made business good.  I'm about 5' 7", I guess,
blond sort of long-hair, and pretty skinny.  I don't
have much body hair, none on my chest, or butt, and
not much on my legs except up around the thighs, and
Jack shaved that away along with my pubic hair.  By
the time he was done, I was completely hairless, and
thought to myself that this guy really was kind of
kinky.

When he was done, he sort of stood there and looked at
me for a while, admiring his work, I guess.  Then he
went and got a bottle of oil, and started rubbing it
on my dick, masturbating me.  It felt really good, and
I felt a little more secure, and got a terrific
hard-on.  But as I got close to coming, he stopped.
Guess he thought it was too soon.  He was into this
dominance thing big time, and was in control.

After he'd shaved me, he went and got a thing that
looked like a long tube with a syringe on one end,
like they use to give you shots, but no needle that I
could see.  He showed it to me, moving it in front of
my face so I could see it.  "I'm going to stick this
into your dick," he said.  "It's called a cathetar.
It'll probably hurt a little as it goes in."  Again,
he waited for a response.  Again, I thought of the
money and said "Yes, sir."  I figured this was not
going to be fun.

And it wasn't.  He guided the tip of the tube into my
dick, and started pushing it inside me.  It felt like
sandpaper.  I was breathing hard, but trying to stay
still so as not to cause myself any more pain.  When
he'd gotten most of it inside, I realized that I
couldn't control my bladder.  Piss was starting come
out the other end of the tube.  He clipped the tube at
the end, though, to stop the flow, and injected
whatever what in the syringe.  I felt an expansion in
my bladder, and looked at him sort of nervously, I
guess. "We're filling a little baloon at the end of
the cathetar with water to keep it inside you.  It
can't come out now unless I let the water out."

Once he'd filled the balloon, he removed the syringe,
and attached the other end of the tube to what looked
like one of those intraveneous bags you see in
hospitals that was hanging from a hook in the rafter.
It had some kind of liquid in it, and the liquid
started to go into me through the cathetar.  After a
few minutes this got pretty uncomfortable, like I had
to pee real bad, and so I started to try to push the
liquid out again.  I could do this if I pushed real
hard, but I couldn't keep it out.  If I relaxed, it
just flowed back in me.  Jack thought this was pretty
funny, and watched me try to get the liquid back out.
Finally, I was so tired I just gave up, and let the
liquid flow.  By the time the bag was empty, I was
really uncomfortable, and kind of squirming on the
table to find a more comfortable position, but there
wasn't one.  I just felt bloated and had sort of a bad
stomach ache, but I could stand this, I thought, if it
didn't go on too long.

Jack disconnected the bag, crimped the end of the
cathetar so none of the liquid could get out, and then
went for another tube that looked the same as the one
that was in my dick, but was larger.  "This one's for
your ass," he said.  "Yes, sir," I said, sort of
panting.

Jack spread a little grease on this second tube, and,
reaching between my legs and moving my balls out of
the way, guided it up inside me.  This one hurt less,
but went in a lot deeper.  Really, it just sort of
felt weird, like I had to take a shit or something.
Then he started squeezing the air-bulb on this one,
and my bowels seemed to fill up.  He smiled down at
me.  "Another little balloon," he said, "to keep it in
place."

Once he'd inflated the balloon, he removed the
air-bulb and went to get a big rubber sack with a hose
coming out of it.  It was wet.  He hung this from the
same rafter over the table, connected the hose to what
was in my ass, and released a clamp that had crimped
the hose, preventing it from leaking.  I felt a flow
of liquid up my ass.  It felt okay, at first, but
pretty soon started to hurt real bad.  Real bad.  I
was already bloated from what he'd put up my dick.
This made that feel a whole lot worse.  My stomach
ache got to be almost unbearable.  I watched as my
belly started to rise, as though I was pregnant.
Again, I tried to push back the liquid, but the effort
hurt so much with each push, that I finally gave up,
knowing it was futile.  The water kept flowing into
me, making my belly bigger and bigger.  I had to shit.
 I had to get it out.  Finally, the bag was empty and
I was crying, begging him to let it out.  "This is
only half-a-gallon," he said.  "Do you really want me
to let it out?"

I thought about the money.  I needed it really bad.  I
owed someone money who would do stuff to me a lot
worse than this if I didn't pay up.  But, the pain was
terrible.  "No," I finally said though my tears, "I'll
be okay," hoping I could get used to the pain.  But
that wasn't going to happen.

Jack disconnected the hose, crimped the end of the
tube up my ass so nothing could leak out, put away the
water bag, pulled up a chair, and sat down by the edge
of the table to watch me for a while.  I just kept
squirming, trying to stop the pain, but it wouldn't
stop.  I think it was the way I was lying, on my back,
with the weight of all that liquid pressing down on
me.  I don't know.

We stayed like this, me squirming, Jack watching, for
a long time.  Finally he got up and started rubbing my
dick again.  This time the feeling was terrible.  With
each stroke, the cathetar moved inside me, scraping
the inside of my dick, causing terrible pain.  But, it
got hard anyway, in spite of the pain.  Finally, Jack
put his hand on my belly and started to push, sort of
gently at first, but then harder.  I screamed and
started to cry again.  Jack smiled and stopped
pushing.

After a while, he untied my ankles and wrists, and
told me to stand up.  This was real hard and real
painful, but I made it, hoping that another position
would relieve some of the pain.  It didn't.  The pain
got worse.  He told me to stand up straight, and to
put my hands on my head.  Fetching a steel restraint
that looked like it had come out of the dark ages, he
clamped my wrists at each end of the pole, securing it
in the middle around my neck.  So, my arms, bent at
the elbow, were held level with my chin and each about
a foot from my head.  I looked like I was in a
stick-up.

Next, he attached two chains to the steel bar and
hooked these to one of the rafters.  Then he made me
bend my knees slightly, and clamped a chain attached
to the floor to my balls.  I couldn't straighten my
legs without pulling on the chain attached to my
balls, which caused great pain, and I couldn't kneel
completely on the floor because the chains attached to
the bar holding my hands and neck wouldn't allow it
without choaking me.  I had to support myself with the
strength of my thighs.

Jack stood back and admired his work again, watdhing
me sort of hanging there, but really supporting my
weight with bent legs, unable to straighten them
without pulling on my balls.  He smiled.  "Just
getting you ready for later," he said.

Before leaving the room (and he was gone for what
seemed like forever), he attached two steel clamps to
my nipples, their sharp teeth cutting into my skin.
Each clamp had a chain that hung down, and he attached
these to a ring that he fastened around my dick.  As
the weight of my dick pulled the chains, the clamps
got tighter, making me scream from a new source of
pain.

"The best answer," he said, before leaving the room,
"is to think happy thoughts.  Give yourself a hard-on
so your dick will rise.  Of course, the hard-on will
make the cathetar move in your dick, and that won't be
pleasant, but if you can keep it up, that pain will be
much less than what your flaccid little dick will
cause your titties."

There was really nothing I could do.  My legs ached
already, and I had started to sweat both from the
warmth of the room, and from the exertion of
supporting my full weight with my thigh muscles.  I
tried just dangling from the bar that held my hands
and neck, but the bar tightened around my throat,
choaking me.  I tried standing a little straighter,
figuring that I could endure a bit of pain in my
balls, but as the chain pulled my balls downward, the
nipple clamps got tighter too, and this was more than
I could stand.  My stomach was terribly cramped.  I
was having spasms of pain as the liquid injected up my
ass made its way up into my bowels.  I had to pee and
shit worse than I'd ever had to before, and I couldn't
do either.  I was stuck, wishing I'd never come home
with this guy.

After maybe 45 minutes, Jack came back into the room
with a ball gag which he forced into my mouth, and
buckled behind my head.  Then he started stroking my
body, running his hands over my chest and belly,
massaging my inner thighs, squeezing my balls, gently
at first, then more firmly.  I was crying.

After maybe 15 minutes of this, he unfastened the bar
that held my wrists and neck, and let me kneel on the
floor while he removed the chain from my balls.  Then,
lifting me to my feet, he pushed me against a huge
8-foot cross, spread my legs wide apart, and tied them
to hooks on the beams.  Next he tied my hands above my
head, forcing me to stand on tip-toes that barely
touched the floor.  When I was secured, he began to
tie my balls, separating them in the ball sack and
tying each ball separately and tightly, and attaching
a small metal weight to each which dangled against the
front of my legs.  The agony continued as he left the
room for another 45-minute break.

When he finally returned, I was nearly exhausted.  He
untied my wrists and ankles, and removed the metal
weights from my balls (though he left them tied).  He
then handcuffed my wrists in front of me, and told me
to kneel over a large pain in the corner.  He began to
remove the tube in my ass, warning me to hold my water
until he told me it was okay to dump.  I did my best
as he slid the tube out of my ass, and then released
my load.  As my bowels drained, I felt some relief,
though my belly still ached from the liquid in my
bladder.  I hoped this would be next, but he made no
move to remove the cathetar.  Instead, he filled the
rubber enema sack again, and inserted another tube up
my ass, filling me once again with half a gallon of
water.  Removing the tube, he told me to let it out
right away, and we continued this process five more
times, each time filling me with a half gallon of
fresh water.  By the time I'd expelled the fifth bag
of water, it was coming out clear, as though there was
nothing more to clean out.

"Clean enough," he announced.  He took me back to the
long table, and told me to lie down on my stomach with
my dick poking through a four-inch hole bored in the
middle of the table top.  This was incredibly painful
as my bladder was still full, and I was lying with the
weight of my middle on my bound balls.  He tied my
wrists and ankles to the corners of the table, and
then moved back and began to strip off his own
clothes.  It was time to be fucked, I guessed, and,
sure enough, he lifted my belly, forcing a pillow
under my middle to raise my ass higher in the air.
Then, reaching under the table, he adjusted the
cathetar somehow.  I wasn't sure what he'd done, but I
heard slow drips hitting the metal bottom of a pail
that he'd placed under the table, below my dick, so I
assumed he was releasing the water in my bladder, very
slowly.  Finally, straddling the table, he forced a
greasy finger up inside me.

Despite the pain, I was very excited.  In fact, the
pain seemed to increase my excitement and the
sensitivity of my body.  He took his time preparing
me, inserting first one, then two fingers into my ass,
finally driving a third one in up to the knuckle.
He'd begun to breath hard, anticipating what would
come next.  Finally, I felt him move his body into
place, and felt my ass part as he began to penetrate
me, resting his weight against my back, pressing me
harder into the table, compressing my aching bladder
and increasing the flow of liquid from my dick.

He fucked me slowly, rythmically, each thrust driving
my belly against the table and releasing more liquid
from my now fully-erect dick.  He was taking his time,
hoping to deflate me, I guess, before he came.

Finally, I felt his body go rigid as he thrust deeply
inside me while, at the same time, reaching under the
table and adjusting the flow from my dick.  Suddenly,
a solid stream of urine hit the pail, and I felt my
bladder empty just as his hot load began to fill my
bowels.  I moaned with pleasure and relief, wishing
that I could come too, but knowing that, with the
cathetar still in place, this was impossible.

When he was done, he climbed off me, and untied my
wrists and ankles.  He ordered me to turn over, and
retied me to the table on my back.  Releasing the
water from the cathetar, he began to back the tube out
of my hard dick, causing me a lot of pain.  But, when
he'd completely removed the cathetar, he began to suck
me while pulling gently on the chains connected to the
nipple clamps, again mixing pleasure and pain in an
irresistible combination.  I came without much
coaxing, my come searing the inside of my dick like
molten lead as it flowed from my body.

This was both the most painful and most electrifying
orgasm of my life, an experience we sought often to
recreate in coming months.  I was scared of him, never
knowing what he would do to cause me pain, but the
pain was always consumated with unbelievable pleasure,
making each experience worth enduring.