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.