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Paying Off a Debt

"A young man discovers a unique way to pay back what he owes."

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Famous Story
Competition Entry: LGBT Sex Stories


My name is Burt. I’m a big good-looking twenty-five year old guy. I know I shouldn’t have included good-looking in that description, But I’m not bragging. I didn’t have anything to do with it, so I can’t claim credit for it. It’s just the way it is. After all, people have said it to me hundreds of times over the years. I said big. I’m 6’2” and weigh 210, but I’m solid, no flab.

I’ve been married a little over two years. My wife Patty is beautiful. She’s one of those petite perky types with a really great body. I’ve got a good job that pays well, which is important because we were able to buy a house, plus Patty likes clothes and stuff. But I decided I wanted to buy something for just myself.

That something was a Corvette. I’d always dreamed of one, so I thought, “Why not?” I had the money. The ‘why not’ was that I couldn’t afford one. Yeah, I had the money, but it was going to wipe out my bank account and really put us in debt. But I wasn’t listening to that voice in my head. I got it and I was happy. That is for a short while.

I was going too fast on a residential street, came up to a sharp curve, skidded into a fence, taking out the fence and half a dozen rose bushes lining it and slammed into the corner of the house.

It didn’t do much damage to the house – nothing structural – but really fucked up the car. I had a couple of cracked ribs, but I walked away. It was proven I hadn’t been drinking or using drugs, but besides having to pay the house owners, I was given a stiff fine - $1,500. Where in Hell was I going to come up with that kind of money. If I went to jail I’d lose my job, probably my house and maybe my wife. I was in deep shit.

After days of going crazy with worry and trying to come up with a solution I was at a loss. I confided to a buddy at work and he told me about a guy he’d heard about who made loans. Now the guy was a loan shark, but that obvious fact didn’t occur to me. I was so desperate I wasn’t thinking straight. Just how fucked up I was you’ll see. Anyway, I went to see the guy.

I first met his “assistant”, a guy named Moe. He was about my age and height, but was as thin as spaghetti. He looked like something from a Tim Burton movie, like originally he been two feet shorter and someone had grabbed his feet and hair and stretched him out. Even his face was long and thin.

I told him my problem and he took me to see the Big Man. He was about twice my age, and wasn’t so big. He was probably 5’9” but was nicely built. You could see he worked out. Whereas Moe was pale blond, this guy was dark and from his five o’clock shadow you could tell he was hairy. He had some sort of thick accent I couldn’t place. I imagined he was from southern Italy or Sicily, or who knows, maybe North Africa. He just said his name was John, which I didn’t believe for a moment.

I told him my situation and he agreed to lend me the money. I’m not going to tell you how much the interest was, because I’m already telling you things that make me look stupid. After getting the money I began thinking about the other problems I had. I needed more than just enough to pay the fine. I still had to pay for the damage I’d done to the house. Then I had a brilliant idea.

One of the things I like to do is go to the races, and I’ve always been pretty lucky. I could take this money and double it or more. Then I could pay “John” back and escape the interest payments.

The next day I called in sick and went to the track, not telling Patty – of course. There was a horse running in the second race named ‘This is It.’ I knew it was the one. I put the whole 1,500 on it to win. It came in fourth. The shit just got deeper.

The fine had to be paid, and soon. There was one solution, to go back to John and sell my soul to the devil. John wasn’t sympathetic. He was cold. Moe, who seldom opened his mouth, stood with a stone face. He reminded me of a weird statue. I was on the edge of panic.

John looked at Moe with an evil grin and said, “I think we’ve got one.”

I didn’t get it.

Then he said, “Moe and I are two-of-a-kind in one respect. We like ass. I don’t mean that figuratively, I mean we literally like to fuck ass. So Burt, let us fuck your ass and I’ll lend you another 1,500. Say no and you’re out of here.”

My mind couldn’t comprehend what he had said at first. I just sat there staring at him dumbly. I looked up at Moe. He actually raised his eyebrows a fraction of an inch.

My brain started to function and I said, “Are you saying that if I let you fuck me in the ass you’ll lend me $1,500?”

John frowned and said, “I think that’s what I just said. And that’s both of us.”

I sat still for another long minute, and then jumped up. “You’re nuts. What kind of sick bastard are you? Fuck you. I’m not anybody's bitch.”

John didn’t react. He just calmly said, “Well then, good-bye. You’re first payment is due next week. Moe, show him out.”

I looked at Moe and turned toward the door. I had gone about half way when I stopped. It was as if my feet wouldn’t go of their own accord. I stood there for about five seconds and then turned back around. “Who’ll know?”

“Nobody.”

“Where?”

“Right here.”

“When?”

“Right now. I’m ready, and I’m sure Moe is too.”

I glanced at Moe, but he still had the same non-expression. I was trapped. The ultimate humiliation. What other option did I have? In my current mental state I couldn’t think of one. My brain was scrambled. I couldn’t get my thoughts together. Time had ceased to move. Everything seemed unreal. I just mumbled, “OK.’

John said, “Come into the back room.”

He got up from behind the desk and Moe walked to a door and opened it. John put his hand on my back and gently pushed me to get me moving. Moe followed us into the room and closed the door.

The room had old Venetian blinds that were closed, casting the room in a soft glow. There was a couple of beat up chairs, a half empty bookcase and a big old-fashioned desk pushed up against the far wall. John and Moe at the same time began unbuttoning their shirts and pulling them off. I stood there stiffly, not thinking what to do.

John said, “OK Burt, get naked. None of this fucking with our pants around the ankles. This is the whole Monty.”

I numbly started getting out of my clothes, taking off my shoes first, as if exposing my body last would help matters. They were both completely naked and pulling on their dicks before I had my pants off. They patiently stood there watching me slowly pull off my pants, then my T-shirt.

I hesitated before pushing down my briefs, but knew it was no good postponing the moment. Both of their dicks were erect by the time I stepped out of my briefs. Mine was still limp. There was no way I could get aroused. I was scared shitless.

A couple of unexpected things jumped out at me. First I noted that Moe wasn’t as skinny as I had imagined. He was muscular, but with those long sinewy type muscles, not the bulgy kind. Along with my looks, Mother Nature had given me a nice-sized dick, but Moe’s was at least an inch longer than mine, and probably just as big around.

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John, however, was another thing. His dick was at least two inches longer than me, and maybe even three, and I swear it was as fat as a big cucumber –at the tip. And it got bigger as it went down. There was no way he was going to stick that thing up my ass.

Moe went over to the corner and picked up one of those quilted blankets that movers use to protect furniture and spread it on the desk. Did I say that Moe hardly ever spoke? If I hadn’t talked to him when I met him I might have thought him mute. He took a pillow from one of the chairs and tossed it on the desk. I was standing with my hands covering my meat and balls. I’m not sure, but I may have been trembling.

John said, “OK, come over here and get up on the desk. No, scoot down so you’re on your back with your head against the wall. Use that pillow for your head. Moe’s gonna loosen you up first.”

Moe stepped over between my legs. He had rolled a condom down over his long straight dick. He grabbed my ankles and raised my legs up in the air, put one of them on his shoulder so he could grab his dick, and took a step closer so his dick met my asshole. I wanted to scream before he even entered me. My mind was yelling, “NO, STOP, DON’T DO IT. NO!” But I squeezed my eyes shut and bit my tongue.

He pushed, gently at first, and then with more force, until my ass gave way and the head of his dick went in. There was a burning stinging pain that made me gasp. He held still for a few seconds and then slowly pushed in. It felt like he’d never stop. I thought his dick was going to come out through my throat.

The pain subsided, almost vanishing, but still stayed enough to let me know I had a big dick shoved up my ass. I have to admit that a lot of the unpleasantness was from the idea that a man was fucking me.

He pulled back a good six inches and then pushed back in. I kept my eyes shut and tried to make my mind think of something else, but to no avail. I was being fucked in the ass. I felt a movement by my side and opened my eyes to see John had gotten on the desk beside me.

He said, “Yeah, Moe, fuck that virgin ass. Nice and easy, let him enjoy it. Another cherry for your collection. Hey Burt, jack my cock while you’re having fun.”

I looked over at him and he had that evil smile again. I looked away, but then back at his massive tool. It was awkward but I took hold of it and moved my hand up and down. I couldn’t get my fingers to meet around it, and was amazed how warm and smooth it felt. When I beat off I never thought about how my dick felt to my hand.

There was a clock on the wall between the windows and I had subconsciously noticed the time when I got on the desk. I looked at it now and saw 12 minutes had gone by. I seemed more like half an hour - and yet at the same time no time at all. It was all part of the weirdness of the whole thing. By now there was no pain, just the feeling of being stuffed with a foreign object up my rectum. And the humiliation of me, a straight man, being fucked by a dude I hardly knew.

John, who had been making comments about how good it must feel to me, said, “OK Moe, I think he’s relaxed. Let me get in there.”

He got off the desk and I saw him putting on a rubber. Moe pulled out of my ass with a loud “pop” and peeled the condom off his dick. I was at least relieved that that meant he wasn’t coming back for seconds. For some inexplicable reason when John stepped up to my ass I grabbed the backs of my legs just above my knees and pulled them up so he could get to my asshole easier. I gritted my teeth and waited in dread for my ass to be torn asunder.

He pushed in and said, “Yeah, nice. Still tight and hot, a perfect fit for my cock.”

I didn’t feel it a perfect fit at all. I felt as if I was going to explode. It felt twice as big as Moe’s had. And yet there was something that felt good about it. Sort of like when you need to take a good shit. Not when you’re constipated and feel blocked up, but when you’ve got a gut full and are going to enjoy dumping it out. I don’t know how to explain it really – but it felt good.

And when he began fucking me in and out, what it did to my prostate was indescribable. I really started to like it. I realized that my dick was as hard as it had ever been. I didn’t want to moan or cry out or say “Fuck, fuck me.” What I wanted to do, or rather did, was smile. It felt good.

John said, “Look Moe, he likes it. Yeah, he likes my big cock up his ass. He likes getting fucked.”

Moe had taken John’s place on the desk, but hadn’t asked me to jack him. I glanced at him and saw he was jacking himself, really hard. I felt guilty from smiling and looked away. I took my dick and started jacking it too. I couldn’t have done otherwise. I was filled with lust, wanting to cum more than I could ever remember wanting to before. And I was excited with the prospect that John was going to dump his load in my ass.

To my surprise Moe got up on his knees and turned in my direction. John said, “Good, you’re ready. So am I. Do it. Let me see.”

Moe threw his head back and let out a funny sound and then looked back down at his dick as it spit out a rope of cum that landed squarely on my chest. It was followed by three or four more blobs, each one landing on a different spot on me. I don’t know if that had anything to do with it, but suddenly my jiz burst out splashing time and again on my stomach. I don’t think I’d ever cum that much before.

John said, “Oh yeah, that’s just about perfect.”

And then to my surprise he pulled his monster out of my ass, which suddenly felt like a vacuum. He pulled off the condom and jerked his dick a few times and shot cum onto my lower stomach, my pubes, my dick and my balls. I was covered with cum from my chin to between my legs. I couldn’t move. Once again my mind was confused. What had just happened? How had I liked it? Why was it over with so soon? What do I do now?

John was wiping off his dick with a cloth. He said, “That was fuckin’ good. Just what I needed. Get dressed and come on out and we’ll wrap up our meeting.”

He tossed the rag to Moe, who really didn’t need it and then Moe dropped it on my stomach. I lay there still while they got back into their clothes and then began wiping off the cum from my body, the best I could. I knew as soon as I got home I’d have to jump in the shower, but it was still too early in the day for me to go home. I’d have to sit in Starbucks for a couple of hours feeling the cum drying and smelling it. Oh, well.

I got the money and made the arrangements and left, my asshole twitching like crazy. I knew when I shit it was going to hurt and I’d have to be careful wiping my ass. Maybe I’d better stop at the drugstore and pick up something like hemorrhoid cream.

That was three days ago. My ass feels fine now, but I have trouble going to sleep at night and concentrating at work. I keep thinking how weird it is that I ended up liking getting fucked. I’m worried about all the money I owe John, and how I’m going to pay it back without telling Patty about it. About the loan I mean, not the rest. I haven’t had sex with her yet since then, and I’m a little worried about that too, but I’ll have to wait and see.

But there is one thing I’ve thought about. Since John seemed to really like fucking me, I’m wondering if I can strike a deal with him. You know, that he can fuck me on a regular schedule and knock some of the loan off each time, or at least do away with the interest. That’d be a good deal. What do you think?

Published 
Written by spinneroftales
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