Story: The Gambler

By | February 22, 2016

I’ve always been an incredibly bad gambler, but I was hooked. For some reason, I just couldn’t stop. It cost me everything; my wife, my job, my family, and almost my life.

Six months ago, I was in deep. I owed a bookie over $60,000 and without a job I couldn’t afford to pay it off. He wanted $2,000 each month, but I was broke and desperate. I thought if I just hid for a while, he would eventually forget about it. I was wrong.

One Sunday morning, while sleeping in the back seat of my car, two of his goons woke me up to the worst beating of my life. They told me that I had 24 hours to make the first payment or I wouldn’t survive the next beating. Sore and bruised, I turned to the only person I knew that had that kind of money – my ex-wife. Kim hated me, but it was my only chance. I figured she wouldn’t just let them kill me. After all, we were in love once.

As I sat in Kim’s office, explaining the situation, I noticed an ever broadening smile on her face.

“Why are you smiling?” I asked.

“Well, it seems you’re finally going to get what you deserve.” she replied.

“If you aren’t going to help me get them off my back, at least loan me enough money to get out of town.”

“No. I have a better idea. I’m going to give you a job.” Her smile was nearly ear to ear now.

“What kind of job?” I inquired.

“One that pays exactly $2,000 a month.”

“But that’s only enough to pay the bookie. How will I eat?”

“You are going to move back in with me. You will clean my house and do anything else I tell you. If you don’t, I’ll stop making your payments and tell that bookie exactly where to find you. Do we have a deal?”

“Yeah,” I replied “whatever.”

She opened her top desk drawer and withdrew her checkbook. She wrote out a check for $2,000 and handed it to me.

“Be at my house at seven o’clock sharp.”

I accepted the check and hotfooted it to the bank. I cashed the check and went straight down to pay the bookie. At seven o’clock, I was standing at Kim’s front door. I rang the doorbell and she opened the door and pulled me inside. The house was as big as I remember it. Sixteen rooms, each with it’s own bathroom. The only thing out of place was the multitude of workmen hustling around one of the upstairs bedrooms.

“What’s going on upstairs.” I asked.

“It’s a surprise. They said it would only take a few hours and they’ve been here since three.” With that she turned and yelled to one of the workers. “How much longer?”

The worker seemed to be contemplating something and then answered. “About twenty minutes, ma’am.”

“Go into the master bathroom and take a bath. I’ll bring you some fresh clothes in a few minutes.”

I quickly made my way to the master bathroom and started filling the oversized tub with hot water. As it filled, I slowly removed my clothes and then sank down into the soothing water. A few minutes later, Kim came into the bathroom carrying several shopping bags filled with garment boxes.

“The workers just left. Your new room is all finished. Are you clean yet?”

“Yeah. I’m clean.” As I climbed out of the tub.

“Good. Let’s get you dressed.” She poked around in one of the bags and finally pulled out a large garment box. She opened it up and pulled out the contents. “How do you like it?”

I did a double take when she pulled out what could only be described as a maid’s uniform. “I’m not going to wear that!” I protested.

“Oh, yes you are. If you plan on living past the end of the month anyway.”

I was defeated. I gave serious thought to just picking up my normal clothes and leaving, but I knew I would never be able to hide from that bookie. I figured it could be worse so, reluctantly, I nodded my head in agreement.

Her smile was again stretching across her face. She pointed to the low bench on the other side of the room, “Lay down over there while I get you ready.”

As I lay there, she pulled out more boxes to reveal other, more embarrassing, items. I almost got up and left when she pulled out the giant cloth diapers. It took all of my self control, and sense of self preservation, to remain still.

“Lift your butt, so I can get these diapers on you.”

Almost in tears, I did as I was told. She placed two of the diapers under me and proceeded to fasten them into place. After she fastened the diaper pins, I heard a snap. I looked down to see that she had placed small padlocks into the pins. This was getting worse all the time. Next she grabbed a pair of frilly pink plastic pants and slid them over my feet.

“Stand up, so I can pull these up.”

As I stood up, I realized just how thick the diapers were. I couldn’t even get my knees to touch. She pulled the plastic pants up over my diapers and then placed a padlock on the waistband behind my back. There was no way I was going to be able to remove them myself.

“Isn’t that cute?” she asked no one on particular. “Now, let’s get your uniform on, shall we?”

As she picked up the uniform, a single tear ran down my face. This was the most humiliating thing that ever happened to me. She pulled the dress over my head and into place. It was obviously cut just for me. As Kim was zipping it up the back, I looked down and noticed that it was cut incredibly short. The lacy petticoats held it up in such a way that my diapers were easily seen. Even when I stood straight up, the bottom half of my diaper was clearly visible. My spirit was broken and I began to sob uncontrollably.

“Quit crying, you little baby, or I’ll give you something to cry about.”

I tried to stem the flow of tears, but it wouldn’t stop.

“That’s it. You’ve just earned yourself your first punishment.”

She grabbed me by my ear and pulled me up the stairs to the newly designed bedroom. When I looked in, I was shocked. It looked like a medieval torture room. Among the many things that I saw was a padded sawhorse, a pillory, a doctor’s examination table, a chair with a hole where you would normally sit and many other bizarre contraptions. She led me over to the pillory, and without saying a word, pushed my neck down into the largest hole. Next, she place my hands in the appropriate places and pulled down the top board. After locking the board in place, she walked out of the room. I stood there, bent at the waist, for what seemed like hours. My whole body ached, including my bladder. I held it for as long as I could, but soon I realized it was a battle I couldn’t win. I figured I would just let a little out to relieve the pressure. However, it didn’t work that way. As soon as I let it go, it wouldn’t stop.

I stood there in my soaked diapers until I noticed that the light no longer showed through the window. At this point Kim walked in and immediately noticed that I had wet myself.

“Looks like someone piddled in their pants.” she teased.

“Let me out of here, you bitch.” I yelled. “This hurts.”

“What did you call me?” She was pissed. “If you think that hurts, wait till you see what I do now!”

She left the room and returned only a minute later with the belt I was wearing earlier. She folded it in half and without uttering a single word, began beating the backs of my thighs. After only a few lashes, I was screaming at the top of my lungs. Undaunted, she kept up the assault until she was satisfied that I had learned my lesson. I guess it was probably about thirty strokes.

After the beating, Kim attached leather cuffs around my ankles and linked them together with a short piece of chain. Next, she lifted the board which held my neck and wrists. As soon as my hands were free, I started rubbing the backs of my now bruised thighs. This didn’t last long, however, as my hands were cuffed in the same fashion as my ankles.

“It’s 10:30, time for you to go to bed. Tomorrow, you learn how to clean my house.”

Again, she grabbed me by my ear and roughly pushed me into the cage in the corner of the room. It was the size of a single bed and had a very thin mattress. She lay me on my back and attached the chain on my wrists to the head of the cage. It would not, normally, have been too uncomfortable, but I really needed to rub my thighs. As I tried to get comfortable, Kim walked out of the room and shut the door. It only took a few minutes to fall asleep.

I awoke the next morning to a very full bladder. I knew by now that it was pointless to resist, so I relaxed and let it go. With the wetting from the previous night combined with the mornings, I had serious doubts about the plastic pants preventing leaks. However, with the thickness of the diapers, it was all contained.

The room was devoid of clocks and I couldn’t gauge time by the sun with the curtains closed. Not knowing the time, I simply waited to be released. Hours went by and Kim was nowhere to be seen. I started having horrid thoughts that she had died in her sleep or something and that I would be stuck in this condition until I starved. Several times I had to pull myself from the edge of panic. Postive that this was just her way of torturing me, I relaxed a little and even took a little nap.

Before long, I felt the inevitable pressure of my bowels. Not prepared to take that final leap into humiliation, I held back for as long as possible. When the pressure turned to pain I gave in and lost control. The diapers didn’t give a single inch. Soon the mess was spread well up into the front and back of the diapers. I felt disgusted with myself and the smell had me on the verge of vomiting. Only a few minutes after this most shameful act, Kim returned. She was wearing a business suit, which made me realize that she had left me this way while she went to work. As soon as she entered the room she knew exactly what had transpired.

“Ohh…” she wrinkled her nose ”…that’s disgusting!”

After opening the cage and unlocking the chain that held my hands to the cage, she led me to the bathroom adjoining this room. This room had obviously been refurbished the previous day also. In one corner was a large changing table with straps that were obviously meant to immobilize whoever was on it. On the other side of the room was a shower. Not an ordinary shower though. This one had several shower heads placed in a circle and a device hanging from the ceiling to hold the hands above the head.

After I was pulled straight into the shower and my hands were secured above my head. Kim then unlocked the plastic pants and pulled them off. Next, she removed the diaper pins and let the diapers fall to the floor. Wearing a rubber glove, she picked up the filthy diapers and threw them into a diaper pail designed to keep the stink in. Hot water suddenly shot out of all the shower heads at once as she turned the handle. The water was under incredible pressure and felt like pins hitting my skin all over. Kim used a detachable hose to clean the parts of me that the shower heads couldn’t reach.

A not so soft towel was used to dry me off after the shower and I was then led to the changing table. After she finished strapping me to the table, she proceed to spread depilatory cream over every area of my body but my head. I soaked in it for about ten minutes and then she wiped away all my body hair. My legs were then pulled up so that my feet were positioned above my head. It was very uncomfortable, but it didn’t compare to what happened next.

“With your diaper on last night, I couldn’t use the belt on your butt. I had to settle for your thighs. Now I’m going to show your butt what it missed out on.”

Again she pulled out my belt and begin spanking my ass with all the strength she could muster. I was crying and pleading with her to stop after only ten strokes, but she wouldn’t stop until she had delivered the full thirty that my butt had missed the night before. I was balling as the spanking ended.

The spanking was over and Kim wasted no time in getting my diaper ready. She placed two thick diapers under my butt and began to pull it up between my legs, when she seemed to have a brainstorm. She walked into the other room and returned moments later. I began screaming when I saw what she was holding. It was a large penis shaped butt plug.

“Stop screaming, you baby, or I’ll give you another spanking.”

I stopped screaming and began pleading with her. “Please don’t do anything too harsh. I’ll do whatever you want. Please don’t use that.”

“What kind of deal is that?” she asked. “You’ll do whatever I want anyway. I’m going to use this on you, because you’ve already demonstrated that you can’t hold your bowels and I don’t want you stinking while I eat.”

She then dipped the head of the plug into a jar of vaseline and placed the tip against my anus.

“We can do this one of two ways. You can relax and let it in slowly or you can resist and I can push it in quickly.”

I tried to relax, but every time she started pushing my sphincter would convulse. Never had I had more than my doctor’s finger up my ass and my ass didn’t like the feeling. Kim started getting angry and impatient.

“I’m tired of playing with you!”

And with that she started forcing the intruder into my asshole. It hurt like hell. I thought I was going to split in half as she continued to push it in. I finally got a little relief when the plug came to rest on the narrow base designed to hold it in place. Even though it was thinner than the rest of the plug, it was still thick. I hated it. I tried pushing it out, but it wouldn’t budge. Kim then released my legs and pinned the diapers into place. The click of the locking diaper pins signalled my inability to remove the unwanted passenger in my rear. A pair of yellow plastic pants was then pulled up over my diaper and locked also.

“How does that feel?” she asked, patting the front of the diapers.

My ass hurt, both on the inside and the outside. “It hurts.” I replied.

“Good. It’s suppose to. Your uniform is all sweaty, so you’ll be wearing only diapers until I get it cleaned or get more clothes, whichever comes first.”

I was unstrapped from the table and helped up.

“Go down to the kitchen and wash the dishes. I’m going to order pizza and if you haven’t finished the dishes by the time the pizza guy gets here, I’ll use the cane on your backside the next time I change you. Understand?”

“Yes, ma’am.” I scrambled to the kitchen and realized that she had taken every dish out of the cupboard and wiped grease all over them. I was only half way through the pile when the doorbell rang. Tears started to come to my eyes when Kim entered the kitchen.

“Answer the door and get the pizza.” She held out a twenty dollar bill.

“I can’t answer the door like this!” I pleaded.

“Yes you can. Now do it!”

Reluctantly, I walked to the door, money in hand. The look on the guys face when I opened the door sent a stab of embarrassment through my heart. I paid for the pizza and returned it to the dining room.

Kim was sitting at the head of the dining table with a broad smile across her face.

“Have a seat and eat some pizza.”

This was obviously another torture method, because as I tried to sit on the hard wooden chair I winced from the pain of the spanking I had just received. In addition to the welts on my ass, the monstrous intruder inside my ass sunk in even deeper as I put my weight on it.

“Don’t be such a whiner,” she said after I let a particularly pronounced whimper, “that slight discomfort you feel now is nothing compared to the caning you’ve earned.”

I nearly burst into tears at the thought of being caned, but didn’t want to give her the satisfaction. So, I just endured it all and ate my pizza.

“Finish eating quick and get back to those dishes. I’ve got some work to do. If you’re finished before I am, I might decide to go easy on you for your first caning. Understand me?”

“Yes ma’am.” I said, almost desperate to get on her good side.

I gulped down the remaining pizza and then quickly finished off the dishes. Kim seemed to still be hard at work in her office, so I decided to try and worm my way onto her good side even more. I swept and mopped the floors and started dusting the furniture.

“Good to see how quickly you’ve learned your place.” she commented as she walked into the room. I hadn’t even heard her come downstairs. “I know you’re trying to impress me, but I’m not going to change my mind about this. You hurt me too many times during our marriage and it’s time for payback. So get used to it.”

I knew she meant it and I also knew how long it would take to pay off my bookie. I was already miserable after only one day and I had years to go.

Seemingly reading my mind, Kim spoke up, “It might not be years, but it will be however long it takes before I think you’ve changed your ways. If that takes five years or five days is completely up to you.”

I promised myself right then that I would do whatever it took to get back to a normal life.

Kim dished up some ice cream and kicked back on the couch to watch a movie. She didn’t tell me to do anything in particular, so I just continued cleaning anything I could find. At 8pm, Kim comes into the bathroom where I was cleaning the tub and states plainly, “Bed time.”

I followed her up to my new room where she had me bend over the edge of the spanking bench. I expected the promised caning and fought to hold back tears. Instead, she unlocked my plastic pants and reached her hand down the back of my diaper and roughly pulled the plug from my ass. My plastic pants were then locked back in place before she sent me to the cage. No restraints and no words, she just pulled up the side, locked it in place and left the room after turning off the lights.

Not being caned was a definite bonus, but I quickly realized that my bowels were churning away. Having that plug in my ass for half the day seemed to have stretched me out and I knew I wouldn’t be able to control my bowels for long. Within a few minutes, I had messed the diaper I was going to be wearing all night.

To be continued…

Leave a Reply

Your email address will not be published. Required fields are marked *

This blog is kept spam free by WP-SpamFree.