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What are the Chances?

"Sure, what goes around comes around, but why can't apply to the good things in life?"

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The house I was born in had belonged to my great-grandfather, then my grandfather and then my father. It had been a stately wood-frame house, but by the time I came along it had deteriorated and needed constant repairs. The neighborhood it stood in had deteriorated even more.

What had once been a nice middle-class neighborhood with single-family homes and small apartment buildings, which had been built later, was now a run-down, crime-ridden area with more and more boarded-up buildings.

My dad owned a small dry cleaning business, and never made enough money to keep up with the repairs our house needed, let alone affording us the chance to move to another area.

By the age of twelve I was hanging around one of the neighborhood gangs, and despite my mother’s protestations, I got more and more into gang activities. When I was sixteen I was a full-fledged member and had developed a tough-guy attitude and a swagger I never completely lost.

Also, when I was sixteen we were all away one day when the house caught fire and burned to the ground. We came home to a pile of smoldering ashes. The only thing we had were the clothes we were wearing.

It was determined the fire was caused by an electrical problem. The Red Cross came to our immediate aid, and being a business man, if a not very successful one, Dad had always paid the insurance premiums. When we got the insurance money we moved far away, to one of the new suburbs which had sprung up around the city.

We bought a small, solid house with a front and back yard. I got a dog, and the start of a new life. But it was hard to leave the old one behind. I was the new kid in a new high school. I didn’t know anyone, and my attitude and swagger didn’t make anyone want to get to know me. For most of the school years I had left, I was an outsider, a loner.

The bad-boy image was pretty popular with some of the girls, so I had dates and a couple of girlfriends for short whiles, but nothing serious. When I was nineteen I was still a virgin, doomed to masturbate forever, it seemed.

Three things happened that nineteenth year, which made big changes in my life. I was working at my dad’s dry-cleaning business, mostly using the steam-press, which I hated. One evening I took the bus into the city (I had no money to even think of buying a car). I was hanging out at a game arcade, playing a variety of video games. An older man in a suit (I now know he was fifty. The way I know that will come later.) was watching me play and began to make comments about how good I was at scoring.

He kept chatting me up, and I was flattered. He asked if I’d like to have a drink, on him. I said “Sure.” We went to his hotel room. He gave me half a glass of vodka – straight. There was no mix of any kind. I tasted it, and that was about it. I may have tried another couple of sips, but I didn’t want any more.

He took off his coat and hung it in the closet. We sat on his bed, as in this dump of a room there wasn’t even a chair. He put his hand on my crotch and squeezed it. I guess I could have slugged him, being the bad boy I was, but I didn’t. No one had ever come close to squeezing my cock before, and it felt damn good.

He unzipped my pants and pulled my already half-hard cock out.

“My god, Garth,” he said. “Where’d you get a dick like that?”

I think I probably smiled. You know where flattery will get you. He kind of pushed me back and leaned down and took my now throbbing cock in his mouth. My mind blacked out.

After bobbing his head up and down for several mad minutes he began pulling at my belt and unbuttoning the waistband of my pants. When he got them open he started on his own pants.

He stood up and pulled them off, saying, “Get out of those jeans. I want more of that dick.”

I didn’t know what that meant, but I wanted more of his mouth sucking my cock, so I pulled my jeans off. He got on the bed on his knees his arms folded in front of him and put his head on his forearms.

“Stick that big dick in my ass. I want you to fuck the hell out of me,” was what he said.

I’d never even thought about fucking anybody in the ass, let alone a man older than my dad. But I stepped up and aimed my cock at his visible, brown asshole and pushed it in.

‘Holy shit,’ is the first thing I thought.

This was a whole new experience for me. I had no idea sex could feel so good. Why hadn’t I ever done this before? Of course, the obvious answer was I’d never had the opportunity to fuck anything but my fist before. Now here we were, me in my T-shirt and Reeboks, and him in his brogans, dress shirt and tie, my cock shoved up his ass.

Even though I’d never fucked before, nature tells you what to do, and I did it. I was pounding away, but it didn’t take me long to cum. I’m surprised I hadn’t shot my wad the moment he’d put his mouth on my cock. But I did now, filling his ass with my teenage spunk.

When I figured my balls had been drained I pulled my cock out. He got up and motioned toward the bathroom with his head.

“You can clean your dick off in there,” he said.

I went in and washed my cock and took a piss. When I came out he was dressed again. He tossed me my jeans. I struggled back into them.

“I’ll give you a ride back to the arcade,” was all he said.

I guess on the ride back we must have said something, but nothing that stuck in my mind. He dropped me off and wished me well or something like that. I caught the bus home and most of that night lay awake wondering what had happened.

The second big change came a couple months after that. I was sick and tired of working in the dry cleaners and the way my life was going, or more accurately, the way it wasn’t going anywhere. I wanted to see the world, so without saying a word to my parents, I joined the navy.

After boot camp, or more properly RTC, in Great Lakes Illinois, I was assigned to the Pacific Fleet stationed on North Island in San Diego.

And then number three hit. My father dropped dead of a pulmonary embolism, leaving my mom all alone. There was a forth change which I didn’t know about yet, or maybe it was just an extension of the third. My mom started drinking.

During my four years as a navy man I saw only a small part of the world. We went to Hawaii on a training exercise, and another time to Guam. The rest of the time I was stationed in San Diego. But I did resume my sex education.

I fucked my first pussy at a whore house in Tijuana, and returned there twice. It wasn’t long before I had a variety of women of all ages willing to serve a young man in uniform.

As for guys, spread out over the four years I did some of that, too. I had two blow jobs when I was drunk (really), one in the men’s room of a bar, and the other in the alley behind a bar. Both of those I was standing up, or leaning against a wall, my cock poking out of my pants.

I fucked a fellow seaman in the ass in the middle of the pacific, which was pure insanity. And that was about it. Again, really!

While I was in Guam my mom, while drunk, fell in the bathroom, hitting her head on the edge of the bathtub. She lay there three days before a neighbor found her. That’s when I discovered how serious the drinking had become. The navy flew me home for the funeral.

When my service time was up I had no desire to return home. I sold the house and decided I wanted to see more of the world than I’d seen so far. I went north to San Pedro and got hired on a freighter. For two years I fucked in almost all the ports surrounding the Pacific.

And I should tell you that the Second Assistant Engineer on my ship who reminded me of Bluto, Popeye’s nemesis, sucked me off once and I fucked him once. It was weird, fucking an ape three times my size.

In Japan I got picked up by a German tourist. We went to his hotel room and I pulled my pants and underwear down to my knees and lay there watching him lick my cock and balls like they were candy.

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He also lifted my butt and licked my asshole. That was my first time for that.

And there was the slim, young kid in Thailand that was more like fucking a girl than a guy.

After two years I felt I’d seen all of the world I wanted to and I didn’t want to do this work for the rest of my life. I needed an education. I still had the money from the sale of the house and my mom’s insurance. I went back to San Diego and enrolled in San Diego State University.

I became a dedicated student, really immersing myself in the books. My rampant sex-life was put on the back burner. On occasion I got in bed with a girl I might have taken a liking to, but my ass fucking had stopped. In my third year I hooked up with a fellow female student I’d dated a few times and we rented an apartment together. About a year later the sex grew stale and we became just friends and roommates for the next six months.

During my senior year I shared a class with a guy named Mike Aziz, and we became friends. After graduation we formed a start-up IT company which took off and grew at a crazy rate.

We were raking in the money and were on top of the world. I got hooked on Las Vegas, and went there to blow off steam every chance I got. It was on one of these weekend trips I met Ada. Corny as it sounds, it was love at first sight. No girl or woman had ever hit me like that.

She was there with two girlfriends celebrating one of their birthdays. We were instantly drawn to each other. She said she thought my swagger was cute! I wasn’t offended. I thought it was funny. We spent every minute together. We couldn’t get enough of each other. Her girlfriends left and she stayed one more day. We got married.

I had been at the Treasure Island and she was at the Rio. We checked out and into the Venetian for a three day “honeymoon”.

At the end of the three days she went home to break the news to her parents. I returned to San Diego to take care of some important business. Aziz and I had been offered an obscene amount of money for our business. We said yes and turned everything over to our lawyers.

Ada lived in Louisville, which was in the general part of the country where I’d grown up, so I was comfortable with the idea of living there. I said goodbye to California where I’d been for the past twelve years and flew to Louisville, hoping my new in-laws would accept me.

I met Ada’s mother first, who embraced me and said to call her either Mom or Carol, whichever one I was more comfortable with. Ada’s father was working and couldn’t get away, but would be home about six, which gave me time to unpack, kiss Ada a lot and get settled in. Mr. Hughes came in the house, and I was stunned.

My new father-in-law was the man who I had fucked in the ass when I was a nineteen-year-old novice!

I didn’t know what to say. I’d never been at such a loss for words, but I realized he was looking at me trying to figure out where he’d seen me before. That gave me a very small out – at least for the moment. From there I didn’t know where this would go.

From that moment on, as the evening progressed, I felt I was walking on eggs, waiting for the shit to hit the fan, as mixed metaphors go. It turned out that evening went well, and so did the next two days. Saturday arrived and late that afternoon Mr. Hughes (he hadn’t said to call him Dad or Fred) announced he and I were going out for some male bonding, or some such shit.

We got in the car and engaged in small talk as he drove to I didn’t know where. I wasn’t familiar with Louisville yet, but we got to another part of the city after about twenty minutes. He pulled into the parking lot of a Holiday Inn Express.

“I keep a room here, just between us,” he said.

I didn’t know what to say. We got out of the car, went in and up the elevator and down the hall to a room. It was growing dark by this time. He clicked on a light and crossed to the window. He adjusted the air-conditioner under the window and closed the drapes.

I was standing there like a dolt. He turned around and began unbuttoning his shirt.

“It took a couple days to be sure, but I finally figured it out. Now I remember it well. This is going to be fun.”

I was still standing like a statue.

“Well, come on,” he said. “I remember that great dick you’ve got, and you know what I want. But this time I want your fine body completely naked.”

I guess I could have argued. I could have said ‘But you’re my father-in-law.’ I could have said ‘No way.” But to what avail? He had me by the balls, so to say. I didn’t want to do anything, or for him to do anything to damage my new marriage to Ada. I started getting undressed.

He got on the bed. “Lie here,” he said, patting the space beside him.

I lay there, propped up on a pile of pillows. In seconds he was down licking all of the area around my cock. I remembered the German in Tokyo, except Mr. Hughes was grunting as he slurped his tongue over my stomach, legs, balls and cock. He engulfed my cock with his mouth, went down as far as he could and gagged a couple of times.

He let my cock go to say, “You know you’re going to ram this big thing up my ass. You ready?”

With a wry smile I answered, “As I’ll ever be.”

He flopped over on his stomach and grabbed a couple of the pillows I’d been lying on. He shoved them under his pelvis, lifting his butt a foot. He spread his legs and reached back with both hands and opened his ass cheeks.

In my later years I’d learned to be prepared. I got my wallet out of my pants and pulled out a condom I had there. I didn’t know how many cocks had been shoved up that ass in the last twelve years.

I rolled it down over my cock. He didn’t object. I got between his legs and inserted my cock. It went in easily, but his ass was still warm and tight. I held myself up with my arms stiffened and moved my hips to ram my cock in and out.

When my arms got tired I pulled out and got off the bed. I grabbed him and flipped him over onto his back. I pulled him over to the edge of the bed and turned him so his butt was right at the edge. I raised his legs in the air and jammed my cock back in. I couldn’t help thinking, ‘Here I am, a thirty-one-year-old man fucking my sixty-two-year-old father-in-law. How did this happen?’

Even after twelve years I remembered something he’d said to me the first time I’d stuck my cock in his ass, and so this time I proceeded to fuck the hell out of him. He was moaning and grunting and tossing his head from side to side while jacking his cock. And I hate to, but have to admit, I was enjoying every moment of it.

One thing wasn’t like the first time. It took me about twenty minutes of ass pounding before I sent my load of cum spurting up my cock and into the condom. I wish I could have seeded his ass, but it was still a great climax. He’d come about five or six minutes earlier and was pretty worn out by the time I pulled my cock free.

I fell onto the bed beside him, staring at the ceiling. We lay there without saying anything for several minutes. He broke the silence.

“You’ve learned a lot since the last time. I guess you’ve had some practice.”

I chuckled. “Not fucking my father-in-law’s ass. This is a first for me.”

“Well, get used to it, because from now on I won’t have to go looking for a dick when I got one of the best under my own roof. I’ll get you a key for here.”

I didn’t have much of an answer for that. Jamming your cock in some guy’s ass feels great, of course. But fucking your father-in-law carries some sort of special thrill. So I guess from here on out for the next few years, my sex life is set. Besides my beautiful wife Ada, who I love, I’ll also be...

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