My Indebted Slave


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Storycodes: M/f; D/s; punish; anal; toys; chastity; tease; sex; cons; X

WARNING! This story is only for adults over the age of 18 and contains Strong Sexual Content. It is intended as a work of fiction for ADULTS only, and the author does not in any way condone similar behavior. If you are under the age of 18 or 21 and reside in a state, country, or planet that prohibits such behavior, stop reading immediately!!

Archiving permitted, but only if you include this statement of limitation of use and notify the author by e-mail.

The author forbids you to make, distribute, or sell multiple copies of this story on paper, disk, or other fixed format.

However, individual readers may make single copies of the story for their own non-commercial use.


Attn: Readers please feel free to send an e-mail to me. I do want to hear from you!

I was seated at the bar, fuming in silence, glancing at my watch and the clock on the wall. My submissive and fiancé Jill was late for dinner, and I was wondering just where she was. Has she been delayed at work? Had a car accident? I had tried to call her on her cell phone, but all I got was a recording saying that number was out of service.

Usually, she was on time, but now she was almost an hour late. I was just about to leave and get driven over to her house when I saw her run into the bar, her hair and jacket a mess.

“Good evening, Master,” she quietly greeted me, kissing my cheek.

“Where were you?” I asked, “and your phone is out of order.”

“They repossessed my car, and I guess I missed paying my phone bill too,” she sighed, “at least I got my car back.”

“Your car got repossessed?” I asked, bewilderment in my voice.

“Well I did get behind in my payments, Master.”

“How did you manage that?”

“Just carelessness,” she answered.

Just then the hostess called my name, and we were conducted to a table for dinner. I ordered for both of us, and we made small talk during dinner, not once touching on her finances.

I lived not far from the restaurant, and could walk. Jill had to drive to meet me, accounting for her lateness. As I was helping her with her coat, I changed the plan for the night.

“I want to see your finances,” I demanded, giving her my best Dom voice, “Let’s go to your place tonight.”

“Yes, Master,” Jill answered, a sound of dejection in her voice.

Jill drove her Lexus in silence, and I decided to let the radio play. No sense in questioning her until I knew the whole story behind her car and phone.

I hung our coats in the hall closet, while Jill made coffee in the kitchen. Then she produced the classic shoe box (one that I had bought her a pair of fetish high heels) filled with her bills.

I sighed, took a gulp of coffee and started work. Shit!

“How much do you make a year?” I asked.

“Fifty thousand, Master,” she answered.

“Well between your car lease payments, rent, credit card bills, store cards, unpaid utility bills you owe nearly that much. You’re broke, unless you have a big bank account to pay all this off.”

“No sir, just about five thousand in savings.”

“How could you do this?” I demanded, “you’re a College graduate from FIT, you should know how to handle money?”

“I don’t know! It just seemed so easy, to charge everything, then just pay the minimum. And they give you more credit each time!” she cried.

“My older brother went broke the same way, I’ve seen this before. Before your creditors start calling we’re going to a counseling firm to arrange repayment – either that or you declare bankruptcy.”

“You’re taking me?” she asked.

“I’m your master and your fiancé, darling. I’m very angry for two reasons. One, making me wait tonight without a call, the restaurant did have a phone, you know. The other for concealing your debts – we are getting married, and this would have killed any chance we would have had to eventually buy a house. Are your upstairs neighbors still on vacation?”

“Yes, Master.”

“Good. I want you naked, in the bedroom in fifteen minutes, after you’ve attended to your toilet. Understood?”

“Yes, Sir!” she answered.

Jill has been my submissive ever since we met at a party. She has been a good lover, partner, and submissive, enjoying my use of her immensely.

“Now go!” I ordered, patting her on the bottom as she bounced out of the living room of her rented apartment.

Glancing at the pile of bills on the coffee table, I exhaled silently. If Jill thought what I would do tonight was going to hurt, then the suggestions that the Credit Counselor was going to make would hurt even more.

After placing the bills back in the shoebox and giving Jill enough time to prepare herself, I entered her bedroom. She was naked and kneeling on a small throw rug next to her bed. Jill was thirty-five, five foot six, one hundred and thirty pounds, brown haired, with moderate sized breasts and nicely rounded thighs. Her lower lip trembled in anticipation of our little scene.

“Are you ready, darling?” I asked.

“Yes, Master,” she answered.

While she kept some of our toys in her apartment for when I would sleep over, I decided that a little harsher medicine would be called for this evening. I sat down on the bed, and removed the leather belt from around my waist.

“Over my knees, Jill.”

She quickly complied, her breasts swinging as she placed herself on my lap. With the fingers of my right hand I traced the beauties of her nakedness. From her neck and shoulders, down her back (her skin was soft and perfumed) and along her ribs, to her bottom. I grasped each buttock in my hand, pressing on her flesh. Then I reached between her legs to her sex, and inserted my fingers inside, finding that she was already wet with desire and anticipation.


“Yes, Master.”

“Do you accept my use willingly?”

“Yes, Master.”

I dried my fingers on a tissue, then folded the belt in my right hand. Jill looked at the belt with an expression of both anticipation and dread.

“Kiss the belt,” I ordered.

“Yes, Master!”

Once she kissed the belt I struck a moderate blow across her bottom, making her jump slightly. With just the slightest pause, I rained a series of strokes across her white bottom. Her flesh reddened very quickly as the leather made one mark after another.

Sometimes I make her count each stroke, other times she would be gagged and her hands bound behind her back. But my silent fury at her irresponsible behavior made me just want to punish her without any other implements.

“Oww! Oww! Oww!” Jill cried as her bottom grew red and her flesh warmed up from my punishment. 

I gave Jill more strokes than normal, just so that her bottom would be smarting all weekend – a reminder of what she had done.

“Oww! Oww! Oww!”

I stopped short of blistering her flesh – she is a business executive, after all, in a responsible position. I wondered just how her colleagues might react to know that their director of marketing was naked over her boyfriend’s lap, getting hit with a belt till she was in tears!

“Oww! Oww! Oww!’ cried Jill, tears running down her cheeks.

I stopped, and presented the belt to her lips. She kissed the leather, her cheeks flush with excitement.

“Dry your eyes then I want you kneeling on the bed – I’m going to take your bottom!”

Jill really doesn’t like anal sex, in fact I only do it very rarely. Only to show my extreme displeasure with her. So she knew why I wanted her bottom this evening.

After drying her eyes with a tissue, she removed a box of condoms and a jar of lubricant from her night table. I quickly undressed, folding my clothes on a chair. I’m forty, still well muscled, but I have to watch my weight.

I took the lubricant on two of my fingers and inserted them into Jill’s flaming red bottom. Her ass was warm to the touch, and I knew that she would be reminded for days about our session this evening. Her hole was tight at first, but I gradually inserted my fingers, loosening up her tense anal muscles. She always kept her bottom clean, for the rare occasion that I might use her there. Like tonight!

“Oooooh! She moaned, in anticipation of my rod.

Finally, she was ready. I cleaned my fingers, then unrolled the condom onto my stiff cock. Then, doggie style, I grabbed onto her waist, and slowly inserted my erect and stiff organ into her nether hole.

“Aaaah!” cried Jill.

Forcing a prick into an asshole can tear the tissues within, leading to all sorts of health problems. Unlike the vagina, which can stretch to accommodate a man’s penis. So I gradually inserted my cock into her hole, pushing but not forcing my manhood into her.


I began a very gradual pistoning action with my cock, slowly removing, then pushing myself back into her bottom, each time making Jill moan and buck. Also I held her waist tightly so that she couldn’t escape my attentions. Her skin had collected a slight sheen of sweat from the exertions that I was putting her through.

After what seemed like hours my rod stiffened even more, and I came inside her bottom. Jill moaned as she felt my cock pulsate inside the latex, fully impaling her on it’s stiffness.

“Ahhh!’ I cried, withdrawing my limp cock from her bottom.

I removed the latex, and threw the condom into a wastebasket. Then I stood up, and motioned Jill to lay down on the bed. After a short trip to the bathroom where I cleaned the come off my cock, Jill was in bed waiting for me.

Joining her under the covers, she placed a condom on my already stiffening rod. She opened her legs, and I plunged between her thighs. Her slit was already wet with excitement, and I had no trouble inserting myself all the way up to my balls. I pistoned inside her, rocking back and forth, giving her the climax that she desired so much – and I wanted to give her.

“Aaaah!” we both cried in unison, as she was brought to climax so quickly. We rocked together, our sweat mingling as one, our naked bodies bound by lust.


Later we lay together, after I had fucked her to a second climax. I could see that her bottom was still tender by the way she gingerly laid her bottom on the mattress.

“I love you, Jill.”

“I love you, Master,” she answered.

“The credit counselor may hurt more than our session this evening,” I cautioned Jill.

“Yes, Master.”

Soon she passed off into sleep, soft snores escaping from her lips. There are many forms of bondage. Marital, financial, sexual. I hoped that Jill would understand what was going to happen next.

Having already gone through this with my brother, I understood what was going to happen next. Jill and I arranged an appointment with a non-profit credit counseling service. I told her to bring last year’s W2 form; her last pay stub, and all of her credit cards and bills.

Just before leaving her house, I suddenly ordered her to place a medium sized butt plug up her bottom. The plug would be a constant reminder of my displeasure regarding her financial position; and she would be fidgeting in the car during the entire time we would be at the center.

The woman counselor commented on my thoroughness, and it didn’t take long. In exchange for setting up a payment schedule (and not charging anything else) her creditors would not dun her paycheck or call her.

Jill sat, shocked, as the woman laid out what she had to do. Cut up all her cards. Not charge anything more. Make all payments on time. Buy new things in cash. Make do with less. Hopefully, once she had cleared up all her debts she could resume “normal” life again – this time without charging herself into near bankruptcy.

During the entire session, Jill had trouble remaining seated. With the plug up her ass, she was very uncomfortable for the hour that we were there.

When we went to leave and I thanked the woman counselor, I got the distinct impression that she knew what was up Jill’s ass – and that she was a submissive herself!

Jill had gone to the beauty parlor with a girlfriend, but her friend had to leave suddenly. She had called me to pick her up, and since I was available, I agreed.

“You look very nice darling,” I said in the shop as I helped her with her coat.

“Thank you, Daniel,” she replied.

We walked outside, and spring was in the air.

“Daniel, my Lexus goes back next month. Could you help me find a new car?” she asked.

“I already found you one, sweetie,” I answered, “in fact, let’s go by my place to see it.”

Jill looked excited that I had bought a car for her. Her joy quickly dissipated when she saw that it was a Plymouth Reliant.

“You must be joking?” she asked, looking at it.

“The owner was a senior who lived around the block and took ill. The car has just seventy thousand miles, and it cost a few hundred dollars. No collision, no car payments, you’ll pay off your debts a lot sooner,” I advised.

“But this is just so – ugly!” she pouted.

“Be glad you’ll have something to drive – if you buy a new car, the creditors would say you’re breaking the agreement by spending too much. Besides, you work in Manhattan and take the train every day. This baby is perfect for the station!”

“No, Master!” she pouted.

“In that case, I’ve created a torment especially to show you the value of money. In the house, please!” I ordered.

Jill looked at me, concerned. What form of devilry had I planned for her?

“Place your arms above your head,” I commanded.

Jill was naked, wearing only her slave collar, and the slutty five inch spike heels which were her pair of “fuck me” shoes. She stood, silent and at attention, waiting for her next orders.

I locked a black leather belt around her waist, and attached a cross belt, attached to which were a dildo and anal plug. Lubricating her bottom, I slid the anal plug in first, followed by the dildo. Then I locked a black leather case to the belt, and turned it on. Locking the leather flap with a small padlock, there was no way that Jill could remove the device.

“Hands down.”

“Yes, sir.”

“Have a seat,” I told her, motioning to the table.

“Since you do not understand the value of money,” I began, “I was rereading Justine by the Marquis De Sade the other day, when I found the part where she had been kidnapped by the counterfeiter Roland. I therefore came up with this little torment on my own.”

Jill sat in silence, her hands on her lap, head slightly bowed.

On the table was a black plastic cover, which I removed to reveal a large canvas bag – and paper penny wrappers!

“Here is a bag containing fifty dollars of pennies fresh from the bank – from the Federal Reserve Bank in NY. Plus one hundred penny wrappers. Your task is to count and wrap them all – exactly! I’ll weigh each roll, then count how many pennies you are short or over – and you’ll receive a stroke of the crop, whip, or cat for each one.”

“Aaaah!” cried Jill.

“I see the dildo has just gone off. The battery powered dildoes up your cunt and bottom will go off randomly during the time you’re rolling the pennies; at varying intensities – just to make life interesting. Now start!” I ordered.

“Yes, Master!”

Jill opened the large bag, and spread some of the coins out on the table. Counting them in piles of ten, she began to stack them, ten at a time. I could tell when the vibrators went off as she appeared to shake with each sexual climax.

“Aaaaaah!” she cried.

Since I’m not a cruel or capricious master, I didn’t enforce any kind of time limit on her. The dildoes would give her enough agony as she raced to complete her task. I walked over to the kitchen, and drew myself a glass of water from the faucet, then one for Jill.

“Thank you, Master!” Jill cried, sweat running between her breasts when I gave her the glass.

“You’re welcome. Continue.”

While Jill rolled the pennies I decided that now was a good time to write my own monthly checks. I got out my stack of bills, my calculator, and checkbook. It was going to be a long – and enjoyable – session!

Hours later, Jill called me over and pointed to the stack of rolled coins on the table. Happy at completing her task, Jill’s brown hair was in disarray, and droplets of sweat glistened on her skin. She had endured one sexual climax after another, judging by the moans that she had made with the toys inside her.

“Stand up, darling,” I ordered.

Once she was standing I gave her a passionate kiss on the lips, while squeezing her fleshy bottom with my hands. I could feel the vibrations of the dildo up her ass, making her squirm.

I unlocked the belt, and removed the dildoes from her holes. She stood silently as she was freed from the instruments of her sexual torment.

The dildo from her sex was glistening with her juices, her sexual honey revealing just how many times she had climaxed from her task.

“Take these into the bathroom,” I said, disconnecting the dildoes from the belt, “and clean them, and then take a shower yourself. Then we’ll weigh the coins together.”

“Yes, sir!” she smartly answered, bouncing out of the room, dildoes in hand, happy to be free of the torment inside her. I quickly heard the sound of running water in the bathroom.

Since Jill is a frequent visitor, she has everything a woman needs here: toiletries, her own hair dryer, underwear, and a complete change of clothes.

I had purchased a small digital scale, and I took one of the rolls, opened it, and counted out fifty pennies. Then I inserted them back into the paper, and placed them on the scale, and noted the weight. I waited until Jill had freshened herself.

“Sit down and weigh each roll,” I ordered, noting the weight of the sample roll.

Jill proceeded to do as ordered, and when there was a difference she opened the roll, counted out the coins, emitted a little sigh, then continued. Each roll was numbered, counted, and any variance noted.

“Finished sir!” she announced.

“What was the difference, total shortages and overages?”

“Forty-two,” she answered glumly.

Each difference would mean one stroke on her flesh this evening in my little playroom/basement. I rent the ground floor of a two family house, and the owners (two seniors) let me use the basement as well. I have turned a corner of the basement into a small playroom.

“Get dressed,” I said, “time to look over your new car.”

Dinner that evening was steaks, then out for a movie, and a return home. Jill knew what was going to happen, and I could see that she was visibly excited by what was going to happen to her.

After freshening up, she stripped, and we went downstairs. My landlords were in Florida, so we had the house to ourselves. I had added sound insulation in the basement so that Jill could really express herself, and I had left the stereo playing in my apartment to cover her moans of pain and pleasure.

My “playroom” looked more like a workroom, as my landlords had never furnished the basement, or for that matter, converted it into an apartment. In one section I had placed faux brick wall coverings, and had built a bondage bench, with ceiling chains that I could hang Jill from.

Naked, she didn’t cover her breasts, but instead proudly displayed her body. I was dressed in a leather vest, black jeans, and boots. Jill was wearing nothing but high heels.

Placing bracelets on her wrists and ankles, Jill was soon hanging from the ceiling by her wrists. I ran my hands over her soft sensuous naked body, making her moan with pleasure and anticipation. Her softly rounded breasts filled my hands, and her nipples were hard. Her slit was wet with dew, as she was clearly excited by the prospect of being whipped.

“Are you ready, my darling?” I asked.

“Yes, Master,” she answered softly.

“Do I have your consent?”

“Yes, sir.”

I removed a flogger from a locked cabinet where I store some of my toys. It was composed of several broad strands of leather, which would mark but not really hurt. Slapping the flogger against my hand, the leather produced a satisfying thud when it struck my hand.

“Kiss the flogger,” I ordered, and Jill did so when it was offered to her luscious red lips.

Slap! Slap! Slap!

The flogger struck Jill’s flesh with a satisfying thud, leaving a dull red mark on her naked flesh every time it struck her body. Jill moaned as the flogger did it’s work, leaving her red hot as the session progressed.

Slap! Slap! Slap!

I flogged between her legs, and she opened them to accommodate my demands. Moaning softly, the flogger further warmed up her already wet sopping pussy.

Slap! Slap! Slap!

Her breasts soon received my next attentions. Jill had moderate sized real breasts, and I had ordered her not have any form of enhancement surgery. I liked my women real – not artificial!

Slap! Slap! Slap!

Her behind was soon red, and Jill would remember this session every time that she sat down at work this week the flogging that she had received. Inside my jeans my cock was rock hard, and I wanted to take her right then.

Slap! Slap! Slap!

“Aaaah!” Jill cried, tears running down her cheeks. The flogger had pushed her to the limits of orgasm, and I had delivered her ration of strokes.

“Are you ready, slut?” I asked.

“Yes, Master, yes!” she sobbed.

I released her and she fell into my arms, clinging to me tightly. Her scent was of her perfume mixed with sweat and that of her wet snatch. I pulled her over to a mattress I keep on the floor. Pulling off my boots, jeans, and vest, we were soon naked together on the mattress.

Jill lay down on the mattress, and seeing my enormous erection opened her legs to accommodate me. Unrolling a condom onto my rock hard shaft, I was soon between her legs, pumping away. The sounds of our passion, plus the faint sounds of the stereo upstairs, were the only sounds in the basement. I plunged away, completely oblivious to anything else. Excited by her ordeal, Jill and I both quickly came to climax, her moans increasing in volume and number as we reached the magic moment together.

“Aaaaah!” Jill moaned, “I’m coming!”

We came together, our thighs exploding in a fit of raging passion that left us both gasping with pleasure. Later that night, I would do it again, this time more languidly in my bed.

Jill waved goodbye to her leased Lexus as we drove away from the agency. Since her plates were up, we had registered the Reliant with new ones, and I would return her old ones.

“Sad?” I asked.

“I liked that car, master,” she answered.

“You just can’t afford it anymore, and besides, this frees up hundreds each month to get you paid off that much sooner.”

“I know, master.”

“It’s easy to get into debt,” I said, “but hard to dig yourself out. My brother did the same thing. Bought everything on credit, paid the minimum, used one card to pay another off. And then they just kept on giving him more damn credit, more cards, each time!”

“Good thing they don’t have debtor’s prison, master.”

“Would make a good BDSM novel,” I observed.


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