Pain and Pleasure

Story by AnonymousMan on 3 Oct 2006

Readers: 5092 Score: 6.9 (37 votes) PDF

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.

Top


Rate Story (Choose rating between 1 (worst) and 10 (best).)

Bookmark and Share

blog comments powered by Disqus