Debby's Debt

I hesitated, I knowed it was wrong, but everything that had happened to me in this room had me so befuddled. I knowed I should stop him, but I was feeling so good deep in my belly I didn't want him to stop, I wanted to see what else I never knowed about my own body.

Mr Mackay didn't give me long to think, his weight was all of a sudden off me and he grabbed a handful of my hair, pulling my head back. At the same time I felt something pressing into my backdoor. He was slowly increasing pressure, trying to squeeze in. His manparts was huge, I had no idea how he expected to fit that plum sized head up inside my tiny hole.

"Stop!" I cried, "It ain't going to fit. You is just too big Mr Mackay."

"Jus' relax sweetie, don't fight it." I tried, but the pressure was too much, It felt like his shaft were bending almost back on itself.

"Goddam you is so fucking tight," I heard him mutter. He ease up on the pressure and said, "Darlin', I want you to try something for me. I want you to push like you is trying to push me out rather than worry so hard about letting me in."

"What?" I didn't make no sense to me, but I was feeling that queer warmth in my belly again and was willing to try anything. I pushed against him and I felt him ratchet up the pressure again. All of a sudden I could feel myself opening up like a flower and little bit by little bit I could feel him squeeze into me. He groaned with pleasure, and I cried out as I felt a sharp pain like I was splitting in half. Then he was inside me. He stopped moving, he was pulling hard on my hair so I was forced to stare up the ceiling. The pain was real bad at first, but I passed after a little while and I relaxed a might.

He pulled out a little and I gasped, then he pushed into me a little deeper. It felt very strange, but not as bad as I imagined. With each slow stroke he pulled back till he was almost out of me, and then pushed a little deeper until he were inside of me so deep I could feel his plums bumping my nethers. I ain't never felt so full in all my life. The pain was near gone now and I was starting to feel stretched in the good kind of way, like when you raise your arms up over your head when you first wake up in the morning.

"Oh God," I heard him moan, "Oh God, Debby," He sounded right choked up.

I winced a little as his weight shifted then asked, "You okay, Mr Mackay?"

"Debby, darlin' I ain't never felt anything like this. You is so tight, yet softer and warmer that apple pie. I feels so good It's making me right emotional."

"Emotional?" I thought, "My little butt was making a tough important man like Mr Mackay all emotional?" I felt a little pride all warm in my chest.

"I'm sorry, darlin' I'll pull myself together. This is going to go an awful long way to resolving what you owe."

I weren't really listening to him though. I was starting to feel that strangeness overcome me again. I weren't just laying still no more, I was sliding back and forth on the desk. There was hardly no resistance what with is being so slick and all, and I was able to slide up and down him.

All of a sudden there was a sharp crack, and a sharp pain on my left ass cheek. Did Mr Mackay just paddle my ass? "Yeeha!" He cried, "That's it darlin' work my cock! You really is something special. I is going to give you a special reward."

My cheek was still stinging when I felt his hand sliding underneath me. Though my back passage was full to bursting with him already, his thumb was now pressing into my other entrance. I was so sopping wet it slipped in with hardly no pushing from him. Then his fingers was pressing into me cleft, searching until they found my most sensitive spot. When he touched it I moaned and bucked hard against him. He gripped me even tighter and began to move his hand in time with his hips. It were like there had been a hole inside me that I didn't even realise was there, and now it was full I wanted to stay this way forever.

He was going torturous slow, and it was driving me crazy. I began to push back harder and deeper. Bucking against him, sliding wildly on the wet desk. I was out of control, it was like my body was no longer mine. Using his hands and hips he guided me, still pulling back on my hair on occasion, like he was reigning in a wild horse.

"That's it Mr Mackay, that's the spot. Please don't stop," I said between gasps. He let me ride him, pushing myself even higher, right up to the very edge, and then he pulled back and slowed me down. I cried out, it was far worse than the pain of him entering me. I felt a all of a sudden empty as he pulled out of me.

"Please don't stop!" I felt like crying.

"Alright, darlin', but first I want you to beg."

"Please!" I cried, meaning it with every inch of my little body.

"Please, what?"

"I don't understand. Please carry on."

"I want you to say: 'Please sir, fuck me in my tight little virgin asshole."

Now, I don't abide much with cussing. The words he said was right scandalous to me, but I was positively rabid to have him give me my release again, I would have done most anything.

"Please, sir," I whimpered, " Fuck me in my tight little virgin asshole. Fuck me real hard!"

With one hand he pulled back my hair hard so I had to arch my back. My breasts was dripping wet and my nipples tingled something fierce now they was in the cool air, no longer pressed to the desk. With his other hand he took a hold of one of my breasts and squeezed. Gentle at first, and then hard. He tugged on the nipple, pinching it, making me cry out. His voice was in my ear then, his breath all hot on my neck, "Debby, darlin', You is just full of surprises. I think you and me is gonna get along just fine." All I could says I response was a long moan.

Then his hand was off my chest and he was guiding hisself into me. I thought I was ready for him, but he were so big I gasped with pain as he pushed in deep and I was stretched almost to the point of breaking. But the pain turned into that delightful full feeling. He pushed deep as he could go and waited for me to catch my breath, then he began to thrust again in a slow and gentle rhythm.

I gave a little squeal of pleasure as his thumb found my entrance again and his fingers began toying with my little swollen nub. It were surprising he could keep such good control, I was slippery as a wet fish. His strokes into me was long and deep, while his fingers was working in tight circles. It weren't hardly any time before I felt myself approaching that cliff edge again. Once more that despicable Mr Mackay slowed up his pace, waiting to just a moment before I thought I was going to die with frustration, then stroking again. He kept doing this for what felt like hours, my poor body was aching. I were so excited and frustrated at the same time I felt like crying, but at the same time I didn't want him to ever stop.

Slow, ever so slow, I teetered on the edge. I could feel he were real close too. His breathing was all ragged and he was losing control of his movements. He slammed into me real hard, right up to his plums, then again and one last time, so hard that shifted heavy desk a few inches forward. He stopped there, his full weight on me, driving into me as deep as he could. Then I felt him buck and shiver and something thick and warm was pumping into me, filling my innards in unabated stream of pleasure. It were enough to send me tumbling over the edge too. I near blacked out from pleasure that ran through me like a white hot poker, and continued to glow like a cooling firebrand for a long time after. My nails dug grooves into the hard surface of his desk. My belly and nethers were pulsing something wonderful.

Mr Mackay fell back into his chair, his member making a real satisfying slurping noise as it pulled free of me. I could feel his seed running out of me like a punctured grain sack. I lay there a good long while afore I regained my wits.

Real slow I raised myself up off the desk. My behind felt like I had been riding a bucking bronco across the county. But it hurt in a good way, if you can picture that. I pulled my skirt down and straightened it out, it was creased something awful, but there was no hope of fixing that in Mr Mackay's office. I tucked my bosoms back into my shirt and did up the buttons. The material felt rough and wonderful on my tender nipples, it fanned the fading glow still present in my loins, causing it to flare up a might.

I did my best to clean up the mess he had made of my face. There was no rags or nothing in his office so scooped off as much of his congealing fluid as I could with my hands. Now I would be lying if I didn't lick my fingers a little just to taste him again.

I was looking for my drawers all over the place, only to see them peeking out of Mr Mackay's pocket. He was still laid back in his chair, eyes closed. I would have thought he was dead if I couldn't see his deep breaths puffing out his moustache.

I stole up to him real quiet and reached out to take my drawers back, but his big hand caught mine and held me tight. His voice was low when he spoke: "These belong to me, darlin'. They's part of your payment."

"But Mr Mackay," I protested, "I can't go outside without no drawers on. It ain't decent."

"Darlin', ain't you learned nothing from what I's trying to teach you?"

"Teach me?" I found the notion very confusing.

"Alright, I was mostly jus' trying to fuck you, but there was an important lesson in there. Afore I was the man I is now I was right 'decent', as you said. I was a tailor. I didn't earn much, but I worked hard, went to church on Sunday and saw to it my wife were cared for. I was poor and downtrodden, but folks would say, 'that Archibald Mackay, he is one decent man. Do you know where that got me?"

i shook my head. I kind of just thought Mr Mackay had always been rich. He continued, "It made me a broken and broke-ass man. I was dirt-poor and tired. I thought I had the love of a good woman, but she runned off with the preacher and left me alone in my misery. So, do you know what I did?"

Again, I shook my head, he carried on, "I decided right then and there that what folks reckons is decent could go fuck itself. I sold everything I had and started a small lending business. I always knowed it was easy to make money like that, but never done it 'cause most folk reckon it ain't a decent way to make a living."

"I took what little I had and started lending it out, charging a healthy interest. It took a long time and I had to be real persuasive in getting people to pay back. But after a good long while I owned this here bank, then the hotel, the shops and a fair few farms. Now I take what I want, fuck who I want. I don't give a damn about what folks reckon is decent and, yet, they all line up to lick my boots."

I thought back to before our 'meeting ' and the line of all the town's most important men coming, hats in hand to meet Mr Mackay in his office. Then I thought about my folks, young and miserable, gone to their graves after a short lifetime of ceaseless toil and hardship.

Afore I came into Mr Mackay 's office had I not been sure of what was decent? Why then was it that, while everything what we done was wrong in every way I knowed, it had felt so darn wonderful.

I walked out of Mr Mackay's office that day excited. Partly it were because of the cool breeze I could feel on occasion on my deliciously tender nether parts, and partly because I felt like I was a new woman.

I was worried at first that I was being corrupted by that there wicked Mr Mackay. But, just a few short weeks into my 'debt repayment' programme I came to realise that it were the other way around now. Mr Mackay was acting like Mutt Jefferson, who all folk knowed as addicted to that pipe they selled folks down at Chinaman Joe's place. Mutt was a sorry sight with his eyes deep as mine shafts, and he was always dirty. He stumbled around town like he was sleepwalking. Folk knowed that if you left anything of value lying around sure as anything Mutt would steal it and try to change it for some of that poppy smoke.

Well, Mr Mackay were like that, only his drug was my ass. He would follow me around town when I came a shopping, he even came out to the farm a time or two. Though, I chased him away like he was a hungry stray. He was a well-respected man now and, though he said he couldn't care if folk didn't think he was decent, I knowed this was no all the truth. If folks found out he was planting himself once a week in the back porch of a girl young enough to be his granddaughter, his world would end. Folks would burn down his bank, take all his possessions and, if they didn't string him up, would drive him out of town tarred and feathered. So he had to at least look a might decent, even if he didn't act it when no one was watching.

So, though he begged, and bought me real expensive gifts, I kept our original agreement. Giving him access to my one-bud rose-garden only once a week. I paid off my debt in no time, but we neither of us talked of this, not wanting things to end just yet. Folks in town would have been amazed if they knowed I now owned my farm outright. They would have flat out died if they knowed about the jewels and gold trinkets I now kept in my safe deposit box at the bank.

Speaking of which, dying was exactly what Mr Mackay up and did one day while buried about 6 inches into me. I thought he was just suffering one of the many pleasure fits we gave each other of a Sunday afternoon. Only this time, he slid out of me and fell onto the floor. His fit carried on only another moment or two, and then he stopped moving, forever. His eyes wide and unblinking. I couldn't feel no pulse, and I knowed he was no longer in this world.

I done a bad thing next. I knowed what folk would say if I had called for help, given the state of both of us. So's I carefully dressed myself and put his pants back on. It was mighty tough work given how heavy he was. Once all sign of me being there was gone I snuck out. I left him there for someone else to find. His housekeeper did just that when she in on Monday.

There was a big funeral, to which the whole town came. There was even folks from out of state came to bid their farewells. I was sad to see the old boy go. He was kind, in his way, and he taught me an awful lot, not just about the birds and the bees. He also he a gift with that tongue of his that was a great loss to this world. No doubt the angels in heaven, or the demons in hell is enjoying it right now.

After that I came into quite a lot of money. Folks was surprised he left me most of his fortune. We was real secret about our arrangement, not even Ester knowed anything, so they just assumed it had to do with his love for my Ma, which most folk knowed about.

I was now the one people bowed and scraped to in town, and I ain't done a decent thing to get there.

And what about that boy Jacob Morton? Well, if'n I left things up to him we both be dead and buried afore he got up the courage to even squeak near me. So, one day not long after Mr Mackay passed I corenerd that boy in his barn. He looked like he was staring into the eyes of a hungry lion as a marched up to him and pointed a finger at him, real angry like, saying, "Jacob Angus Morton, I know you like me boy, and if you don't pluck up the courage to come over and court me I will take you across my knee and tan your hide, so help me I will."

That got him a stuttering and a stammering. But it weren't nothing compared to how he reacted when I pluged my hand into his pants and grabbed a hold of his manhood. It was every bit as huge as I had dreamed it, and it was hard enough to crack an egg on.

"Now don't you try telling me you ain't got a crush on me when you is carrying this around in your pants just having me near you." He moaned as I squeezed just hard enough to hurt a little.

"N-n-no Miss debby," he managed to gasp out, "I really like you an awful lot. I d-d-do, truly and h-h-honestly."

"Good," I replied, still craning my neck to glare up at him, " Then how comes it each time you see me you go a runnin off like your tail is on fire?" I have him a little tug so's his knees almost buckled and he grunted.

"I-i-i'm real sorry, miss debby. It's j-j-just that you is so awful pretty. I want's to talk to you, really I does. But any time I trys my mouth goes all dry and I can't get a word out."

"Well, you seem to be managing just fine and dandy now." I pulled him up by his root so's that he came out of his britches. It was my turn to gasp when I saw what he was packing. Mr Mackay was a big man, but that there Jacob Morton is a horse.

"Now why, Jacob Morton, has you been hiding this from me? It ain't right to deny a girl you says you like something so wondrous." He coughed and spluttered at this. These was not the words he expected to come from lips as sweet as mine. But if he was shocked by that he was considerably more shocked when kneeled down and used them same lips to plant a sloppy wet kiss on the great big the head of his manhood. He was whimpering like a puppy and I had scarce begun.

I swallowed him like I was poisoned and he was the cure. My tongue worked on him like I was sanding him down for a fresh coat of paint. He stood there, stiff and too scared to move, like if he did he would wake up from a dream.

I came at him so hard and fast that the boy scarce had a chance. In moments I felt him shudder and cry out and then my mouth was flooded with his seed. I do mean flooded, I made a note to talk to that boy about not believing everything his momma and the preacher says about hairy palms and going blind. I fair choked on the torrent that came out of him, but I swallowed down every creamy drop and licked my lips, wishing for seconds.

Then, after I tucked his member back into his pants, I raised myself off the ground, gave him a coy smile and placed a chaste peck on his cheek. I said to that boy, "now Jacob Morton, if you come across all shy when you thinks about coming over and courting me just remember, this is only the start of what I wants to do with you. I'll expect you over right quick, and dressed up smart, otherwise I might just set my eyes on someone else."

And wouldn't you know it, The next day Jacob Morton was a-knocking the door to to my house dressed in his sunday best and carrying the prettiest posy you ever did see. I gave his fine figure a careful looking over and came over all thoughtful. He was a man that knowed nothing about how to satisfy a woman completely but, and I grinned as I thought it, I was going to have a lot of fun training him up till he did.