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Before I begin telling you what I'm about to tell you, I think you need to know a little about me and who I am. My name is Wilson. Yeah, that's my first name. I was never fond of it, because most people thought it was my last name. Wilson Montgomery was my full name, though my friends just call me Monty.

As you can see, I'm all puma, with both my mom and my dad being pure bloods. Here in Wildwood, that wasn't always the case. The problem with being pure bloods though was that after a few generations, you found your choices of a mate to be coming close to inbreeding unless you branched out a little.

My parents moved to another state the year after I graduated. Since I was an only child, that meant they ended up leaving just me behind. I mean, I could have gone with them, but all my friends were here, and I had gotten a job on the sly they hadn't known about.

It had been the usual; blah blah blah about going to college. That was great and all, but I was far from being the brainy type. I was athletic and had been on the football team at Wildwood High, but I knew I wasn't good enough for a scholarship anywhere. Some of the other guys might make it, but not me. And I had looks, which not everyone had. And those looks had attracted both sides of the gender line.

It was, therefore, a good thing I swung both ways.

So. My job. I was an exotic dancer at a club a few miles outside of town. It was pretty nice really, with a few big-assed bouncers and everything. It was clean, and the cliental was more upscale than you might expect. There were private rooms for doing whatever, and the booze was classier than run-of-the-mill beer and cheap vodka.

I made some damn good money doing what I did. I danced on the stage, and I did tricks in private. On slow nights, after closing, sometimes we paired off and did each other. It was cool. And the money. Did I mention the money? I was never going to be a millionaire, but I didn't have those kinds of aspirations, so it was all good.

So then, you have an idea where this starts. But boy, wait until you get to the ending.

I was working one night when I saw a gentleman I recognized, but not from being a regular here. He was a businessman, and I even knew who he worked for. He was a partner in Bruin and Associates. I knew who he was because he had a couple of daughters, one of whom had graduated with me. Bonnie. Bonnie Behrman.

She had run off and gotten married like a week after school was out that year. I hadn't seen her since. And this was definitely her old man. And he was getting soused to beat the band. He was the uptight kind; you know, I mean even right now he was still wearing his tie and suit jacket. He was a big beefy sort of animal that left you wondering if he was as tough as he looked.

While we were on stage, we wore masks; those silly masquerade ones that didn't fool anyone. I think half of the customers would have been better off wearing them, for they had more to lose if discovered than we did. The dancing gig took us from one stage to another, and if we found a mark, we would slip off and make room for someone new. I danced around in front of him for a while before he seemed to even notice.

Of course, a tail across the face can do wonders.

He looked up at me with blurry eyes, which then struggled to focus. This guy was three sheets to the wind, and it was only just past seven in the evening. His eyes cleared up as he looked at me.

"Hey!"

I leaned down.

"Hey yourself, big guy."

"You available?"

"You have the cash?"

He pulled out a small wad. Flipping through it, he asked me,

"What will five hundred bucks get me?"

"Mister, just about whatever you want!"

"Really?"

"You're damn right!"

"Here?"

"Out in the open? I don't think so. Boss frowns on that. I'll see what rooms are available."

I came back a few minutes later.

"If you're still willing, I have the place."

He got up and teetered a bit.

"I'll follow. You lead."

Now I'll tell you, I was looking forward to the money, but I was actually looking more towards what we would end up doing. This guy had been married for decades. Bonnie had been kind of attractive, for a bear. I wasn't hooked on one body type, because everyone was different. Here, on stage, you could find everything from antelope to porcines. Sometimes a carnivore just wanted to fuck an herbivore just to say they had crossed the line.

Honestly, there were no lines to cross. Sex was sex and if you got paid for it, it was all the better. I had fucked nearly everyone who worked here, though curiously enough, not the boss. And each one had their bright sides, and each one had their faults. It was a matter of looking past the latter, and not being dazed by the former.

This big ole boy, now he was going to prove interesting. I knew who he was, and yet, I was pretty sure he had no idea who the hell was behind the mask.

I ushered him into the room and locked the door. That was a little dangerous, but as I said, our clientele were generally of a higher class than you might normally expect from a place like ours. Keeping up standards made for a better workday, at least for me. I didn't need the seedy low-life types trying to nail my ass. Who the hell knew where their dick had been?

So this guy sat down on the edge of the bed and looked at me. Now that he was here, he looked completely lost. I thought that was adorable. Here was the big executive type, and he wanted something different and didn't even know how to ask for it.

"So, Papa Bear. What do you want to do first?"

"I don't know. I've never done this before."

I gave him a genuine smile, showing my white teeth, followed with a lick of my tongue around my lips.

"I doubt that big guy. Or did you mean in a place like this."

He sighed.

"I mean outside of my species."

"Sex is sex. Anything else you have to say about it only complicates matters. You have the money and I have the goods. I don't charge by the hour, but every minute that passes is wasted time."

"You seem to know your stuff."

"I'll tell you what. After it's all over, you can make that call. Right now, unless all you want to do is talk, I'd suggest you get undressed."

"Yes, that would be best."

Despite having a desk job, this guy was still pretty ripped. I think it came with the territory. I didn't have to exercise to look as good as I did, but it sure as hell helped. He stripped down, looking almost embarrassed to be there down to his fur. I figured I needed to be the ice breaker, otherwise we'd be sitting here all night. Five hundred bucks to do nothing might seem like a bargain, but it would be a boring bargain.

"So?"

"I don't know. What do you recommend?"

I sighed.

"You need to relax. I think a little foreplay might be in order."

Before he had a chance to question what I meant, I spread his thick hairy legs and went for the prize. He had a decent half- boner showing, though I was thinking it was just a nervous one. For his size, I would say it was medium in length, though on the face of it, it was a formidable weapon. I mean, this guy was at least three times my weight and a foot taller, so use that scale for reference.

I didn't give him a chance to argue. I grabbed that slab of semi-erect bear-meat in one paw, while my other one went to his balls. I gave him a tickle and found a couple more inches suddenly showing itself. That was more to my liking. Little cocks were great when you first started this business, but once you learned how the handle to bigger ones, the small stuff was for the rabbits and the hares.

I leaned in and took the head of it in my mouth, sucking him slowly as I wove my tongue back and forth across it. He groaned and grabbed my ears, though thankfully didn't go full berserker and ram my head down over it before I was ready. That really sucked when customers did that. It took training to get your throat to accept something bigger than your average meal and even then you worked up to it.

I kept working over him, slowly going farther, and thus taking it deeper and deeper until I had the whole thing down. My gag reflex had been subdued a while back, and it was part of the reason I could make a bit more cash than the others. His cock was hot, and I tried to imagine him banging his wife with that thing. She was built to take it, and that diverted my mind to some of the others here at the club. Sally the Bobcat; she would have been screaming with that thing rammed between her thighs. I was well built, and I looked bigger than I was due to my physique, but this thing was a total powerhouse.

It didn't take long for him to blow. I could feel him tensing up within minutes, so I relaxed the best I could. Sure enough, his grip on my head went from mild to ferocious in seconds, and his strength was enough to take it clean off. He slammed it repeatedly against his body until his cum nearly made me choke with the intensity of it. I hadn't been face-fucked that fiercely in a long time.

When he was done, he let go of my head and pulled out of my mouth, seemingly embarrassed by what he had done.

"Sorry..."

I finished swallowing and wiped my mouth.

"You're just getting what you paid for."

"You don't mind?"

"Not a bit. So, what's next?"

He thought it over for a moment.

"How about some anal sex?"

I went to a drawer and pulled out the lubrication. I was definitely going to be in need of that before the night was going anywhere. I turned around to find him stretching out on the bed, face first into the pillow. I stared at him a minute before concluding that he had meant that he wanted anal sex as in him personally.

"Hey big daddy; are you wanting me to do you?"

"Is that alright?"

"Sure thing. I thought you wanted it the other way around."

"Maybe later. I don't think I could keep it up right now. Maybe after a little attention I might be able to."

"Your choice. I aim to please."

I started by fondling his balls, running a finger across his butthole with my other paw. He was definitely uptight, for every time I tried to slip inside, he clamped down like a camera shudder. It seems that part of him wanted to be violated, and the other half was having reservations about it. For a big guy his ass was one hell of a knotted-up hole. I was kind of excited to be the first to take his cherry, but unless I just rammed it in, that wasn't going to be happened anytime soon. And I was even taking into account that this guy was at least partially drunk.

I put the opening to the tube of lube up against his sphincter and gave it a squeeze. The clear gel flowed out until there was enough to smoothly ram a baseball bat up his ass. He wiggled a little at the coolness of it, but remained stoically still.

"Hey papa bear. You need to relax, or this is going to a horrible time for you."

"I wish I could relax. Everything in my life stresses me out," he mumbled, his voice slightly slurred from the depths of the pillow.

"You poor deer," I said, a bit condescendingly. "Maybe you should take a vacation."

His head came up.

"With my family? My wife ignores me, my daughters ignore me, and I don't really have anything in common with anyone anymore."

"Maybe you need to rethink your life."

Here I was giving advice to a affluent old bear.

"That's why I'm here. I don't normally drink, and I've always done what was expected of me. Now I'm doing the opposite."

"Gotcha. I just hope you don't come to regret it."

"Won't know until I do it."

"Good point. Alright big boy, relax that ass of yours, because I'm going in."

He dropped back down and clutched the sheets, while I got into a good position behind him. This was going to be far better for me than it was going to be for him, but whatever. Getting paid to pop a cherry usually worked the other way around.

I worked the head of my cock around his tightly clamped ass, getting all nice and lubed, and then, without warning, shoved it in hard. He let out a startled roar as I slammed my hips into the effort, figuring if he was going to get pissed, I was done for regardless. I pushed in all the way balls-deep, digging my nails into his fur and throwing my weight on him in an effort to slow down any retaliation he might take.

To my surprise, he settled down quickly. I lay there just clutching him, still not sure what plans, if any, he might have for my demise. But there was nothing.

"You ok?"

"Yeah. Not so bad once you're in."

"Good. I thought you were going to take my head off."

His ass squeezed down around my shaft.

"I'm not that tight, am I?"

I saw he still had a little sense of humor. That boded well. I didn't think his type had it in them.

"Papa bear; for one, I was talking about the one on my neck. As for the other, I fucked a vixen in the ass who wasn't as tight as you. Now just relax and let me see what I can do about making this pleasurable for you. I'm beginning to think you're just here for some punishment."

"maybe..." came a small voice.

"Too bad. Now hang on."

I pulled back, feeling the tautness of his rectum along my shaft. He was so damn uptight that the head of it wedged against his insides. I could have pulled it out, but with just a light touch, it remained pressed against his sphincter. He groaned a little as I did that, a noncommittal sort of noise. I couldn't tell if he liked it or hated it. But as he was holding still, I decided to just go for it.

You know, it isn't often you get a customer who wants to get fucked. When you do, you're getting paid to screw, not be screwed. And when that happens, you make it last a good long while, because that's usually what they do. I started out slowly, pulling back and shoving in again with slippery ease. My grip on his hide was solid, and I was sure my nails were leaving marks. Great thing about fur; if you were careful the marks never showed.

That big butt of his was quite the pad to lean against, and despite knowing he had a desk job, I was equally aware that he naturally came well-muscled. He hadn't been bench-pressing or lifting weights, I assumed, but he was still a hunk of beefy bruin.

I found I was feeling particularly sexy being the dom to such a large client. A lot of times, someone got hurt because these guys just didn't recognize their own strength. But he was laying here as docile as could be, so I took matters up a notch.

I pulled my cock all the way out, and then shoved it back in. He grunted and clutched the sheets, his claws tearing into them a little. I did it again and again, until that hole of his finally began to cave in due to my persistent ramming. The whole of him seemed to sink against the mattress as I pugged away. I had no idea what the hell was going on inside of his head, but as my concern was with the opposite end of his body, I focused on things there.

Ten minutes in and he seemed to have passed out or gone off to dream land. I was wise enough to know that if he woke up disoriented, I was going to get the shit beat out of me if he had no idea where he was or that he had asked for what he was receiving.

"Hey papa bear..."

"Yeah?" he replied groggily.

"You still good?"

"Feeling great!"

"Ready for more?"

"Go for it, little kitty."

I took that as a bit of an insult. My stature might be smaller than his, but for my size, my cock was proportionally bigger than his.

Yeah, like that ever mattered in life.

I tore into him with a full-blown rage, in part to defend my honor. Little... If he wanted little, he could have taken up with Buckley, the stag. Nice long one, he had, but thin. Worked for the right types. But this old bear would hardly have noticed it.

I was going to make him beg me to stop. Yeah, I knew better than that.

My testicles were slapping up against him, beating against his fur like a pair of wrecking balls. My cock was going as deep as I could get it, each inward thrust poised to be harder than the last one. After five minutes of nonstop slamming, I heard him let of a sigh and knew that I was having the opposite effect on him. He was getting into it with each passing second.

I let go of him and changed tactics, moving my paws to his huge set of balls and fondling them as I had before. He grunted and dug in even harder as I played with his family jewels, even as I was reaming out his ass.

This guy had been living the wrong life all of these years.

Funny thing was, I saw it more than you'd think. These guys would grow up conservative and repressed, doing everything expected of them, and in the end, making everyone happy but themselves. I didn't know if he was secretly gay, or if he just had never had a chance to experiment when he was a kid. You know how bears are. Often touchy and grouchy. Not the younger ones mind you. Just the older ones.

Oh well.

Time to make it count.

I turned it on to full rape-mode, putting my full weight into fucking that ass of his. His grunts were now timed with every slam I gave him, and despite the abuse his hole was taking, his repression (or whatever) was keeping it as cinched tight as a locker-room gym bag.

All the better for me.

He came before I did, because like I said, he needed to get his nuts off pretty damn badly. I let him blow his wad on the bed, focusing on what I was doing. His rhythmic contractions however, were a little to strong to ignore, and while I held back for a minute or two, I finally had to succumb to the urge and I launched a load of feline cum into his ass with as much gusto as I could.

When I was done, I fell forward against his posterior, gasping for breath and feeling pretty damn euphoric. Funny how bears weren't really my type, but this fella had gotten my interest. And yes, a large part of it was breaking him in. I had shown the ways of bisexuality to any number of my classmates before I had graduated, and a few even after that event. I was the go-to guy for such things around here, though that had tapered off as fewer at the school remembered who I was.

Anonymity had its advantages you know.

Anyway, I was resting there, my cock still inside and still pumped up for action. I didn't know what was next on his agenda, though I doubted it was anything concrete. I waited a moment or two before broaching the subject.

"Anything else you'd like?"

He pushed himself up to speak.

"I don't know. You up to taking it?"

"You up to giving it?"

That made him pause.

"I think so. Twice is more than I've done in six months."

"I guess we can find out."

I pulled out, listening to him groan and then sigh once I was clear of his hole. Some of my cum dribbled out, but it clenched up as tight as before, halting the leak surreptitiously fast.

He got up and turned around.

"I made a mess on the bed."

"Sheets get washed after every use. And that's why."

He smiled shyly, an unusual look on his intimidating face.

"I'd get in trouble at home for that."

"Well not here. How do you want me?"

He looked me up and down.

"Any way I want?"

"Unless you've you something dangerous in mind, I aim to..."

"...please, yes I know. If I'm on my back and you're on top? Would that work?"

"Cowboy? Sure. What's the matter, afraid you'll hurt me?"

"Maybe. You are kind of skinny."

"Thanks for noticing. Just remember that I'm just fine for what I am. A puma is never supposed to look like anything else but what it is."

He tittered a bit.

"I like you kid. A bit mouthy, but in a good way. Kind of a breath of fresh air compared to the people I normally deal with."

"I like you too, for some odd reason. I guess I felt a little sorry for you. You look like you have it all, and when you get right down to it, you've hardly got anything."

He smiled ruefully.

"You seem to get it. I like that. Wish others in my life did."

"Not for me to handle I'm afraid. I'm kind of a here-and-now sort of guy."

"I bet you are."

He pulled the top sheets off, leaving the fitted on the mattress. From there he rolled onto the bed and lay on his back, sucking in his stomach a little.

"Can you fit?" he asked me on all seriousness.

"On your belly or over your cock? The answer is yes to both."

"Good, good."

He was a little limp after having two loads removed, but a liberal application of gel in my paws brought him back to life in no time. I rubbed plenty over my own ass, knowing I was going to have to work at getting it back to normal when I was done, and assumed the position. Since he was a little lost at how to handle this, I worked his tip to my hole and pushed back, sitting up as it slowly slid I n.

"Oh fuck! You are one tight little kitty!"

"You, papa bear, have just been fucking the wrong holes for a long, long time."

He looked at me as I struggled to get down all the way over him.

"Wasn't always the case."

I was making a face as I twisted and rotated to get down all the way over his meat.

"Do tell."

"Not much to tell. At home, we just sort of lost interest in sex a long time ago. We used to have some great times together."

"Things can get old. Ever try to spice it up?"

"I used to. Everything I tried just seemed to make it worse."

"I don't know what to tell you big guy. You seem to me to be a lot of fun."

"All I do is just sit at desk all day. There's no fun in that."

By now I had wiggled all the way down and my ass was at the screaming point. It was going to be one hell of a ride if he decided he wanted to let loose with his wild side.

"But you obviously have a lot of money."

"Kid, money has never bought me happiness."

I grimaced just a little as he pushed me down and pulled me back up. He actually gave me a kiss on the nose.

"No?" I asked through tight lips. "I would think that at least it would put you in a better bargaining position. I can think of a lot of things to do with cash to make someone happy."

"You'd think that, wouldn't you? Everyone sees what I am and not who I am."

"And who are you?"

He sighed.

"I'd know anymore kid, I really don't know."

"Not sure I can help with that either."

"Not asking you to. Just hoping to take the edge off before I have to go home. Told my wife I was working late. This wasn't quite what I was planning, but it's been fun so far."

"Glad to be of service."

"You're a good kid, for a cat. Never had a lot of use for them before but I think maybe I've been a little too stodgy."

He was shifting my whole body back and forth, and those massive arms had a ton of power in them. And yet, for the time being, he was being pretty gentle. For a bear that is. I had read the police reports about problems with ursines, and they were not a fun bunch to deal with when they got riled up.

"Thanks...I guess."

"Wasn't an insult. I'm just seeing what I've been missing."

"Good for you papa bear."

He shut up after that and rocked me back and forth over that cock of his. I had taken more...once...and I was finding myself a little overwhelmed as I had that time. But a horse he was not, so I had that going for me. I'd come out of this walking straighter than that time.

He moved his paws until he was almost hugging me, clutching me like I was some oversized doll. I could feel his chest rumbling as he hummed some tune to himself, all the while rubbing his paws across my back as he worked me over his meat. It was weird, and yet sort of nice. Most of the clientele just had you bend over, they fucked you hard, and once they came, they dressed and left without saying much of anything.

This guy was different. I was having trouble seeing what problem his wife had with him. He seemed pretty nice on the face of it.

I knew I was in for a long ride though. Two wads gone meant the third would be slow to come. As long as he was playing nice, I figured I'd be fine. By the time he cut loose, my ass would have acclimated to having his great big sausage rammed up there.

"Hey kid?"

"Yeah?"

"I ain't hurting you am I?"

"I'm holding my own."

"Good. I don't like hurting nobody."

"Appreciated, I'm sure."

He kept stroking my fur and humming to himself, which I found odd, but a nice kind of odd. It was like he was in his own little world, and I was just there to act as a prop while he considered where his life had gone wrong.

After a while he let go of me.

"Hey kid, you mind taking over for a while?"

"As in?"

"You do the work. It's your ass I'm fucking, but I don't want to hurt you. You'll be more likely to stop before you get hurt."

"That's a considerate thing to do. I'm tough and flexible though."

"Trust me kid, this will make me feel better. Just do what you want until you get off. If I get off too, then great."

"Whatever you want. Can I ask what this is all about?"

"Sure kid. Telling you won't matter none. You see, my first time was with a classmate of mine. Another bear like me, of course. We got ourselves a dirty magazine, and while it had all kinds of females in it, there was a photo of a Black Bear sow taking it up the ass from a Grizzly. We both thought that was so cool. It was a couple of weeks before it dawned on us that we both had assholes."

"You did each other?"

"You bet. Got the lotion and ran off to the woods."

"And?"

"You know kid, I like ladies real good. Got two daughters if you need proof. Not sure I'd say I'm gay, but those first times with my buddy have never left my head. We fucked each other silly. And you know what? We never had any qualms about it. We shared in everything. I did his ass, and when I was done, I rolled over and he did mine. Even had a competition once to see how many times we could do it in a day."

"And?"

"The record? Fourteen. I was never able to best that."

"You fucked fourteen times?"

The old bear laughed. I could feel the rumbling in his belly from more than one place on mine.

"That was the number of times we each lost a load sonny. The total was twenty eight. Nothing more and nothing less."

"I'm hardly in a position to call you out on it, but really?"

"Yeah, really. We here horny as hell and that worked perfectly for taking the edge off the old hormones. But then his dad got reassigned and they left town. I was depressed for months."

"I bet. It's hard losing your best friend."

"You got it kid. Ever since then, it was do your schoolwork; and learn to be productive; and blah blah blah. I put myself into it because I had nothing else to look forward to."

"And now you're miserable," I acknowledged, laughing silently at his use of blah. I got what he was saying..

"Pretty much. But this is nice. It brings back some pleasant memories."

"Glad I could help."

"Yeah. You're a good kid."

"Thanks."

The conversation lulled after that, but I earned a new respect for this guy, He might seem to have it all, but he lacked those things that really counted. I made good money, and that was nice, but I had friends too. Seems like this guy didn't have any.

I rode his cock for a good long while, finally getting to the stage where it was enjoyable for me. I think he understood that, and after a while, took over again. It was a silent exchange, as he reached out and pulled me down, at the same time bringing up his knees and holding me tight.

Let me tell you, when a bear puts his body into action, there is not much to compare, size for size. The stimulation was so intense that I immediately had a rock-hard erection, and the soft slippery fur of his belly was exciting it even more. When he put his back into it, I felt as though I was going to be able to pass bricks for the rest of my life. That huge hot cock of his was driving into me like a freight train, with my hole now so stretched that it was going to take some serious exercises to put it right again. I envied him his tension, and that ability to snap back shut again like nothing had happened.

When he came, it was so copious I could feel each spray coming from him, until I was just sure that I was never going to make it to the bathroom before it all leaked out. The combination of his arms and his hips was nearly what I would call devastation, and all the while, I was feeling myself build to the ultimate climax.

I came on his fur, my balls so tight they hurt. I shot my load like someone had overloaded a musket. My ass tried to spasm, but there was no room for it. My partner grunted and shoved his way in until I just wasn't going to be able to take any more. Then, with a little cry and a sigh, he pulled out and hugged me close.

After that things seemed to get a little awkward. I don't think he had come here for anyone to listen to his story. I had. He went and got cleaned up, came back and got dressed. Only then did he look at me.

"Thanks kid. I didn't mean to dump my life in your lap."

"You dumped more than that in another place, so I'll call it good."

He pulled out his wallet.

"Here," he said as he handed me another hundred dollar bill. "I think you earned a little bonus."

"Uh. Thanks?"

"You went above and beyond. I respect that."

"Thanks papa bear."

"No, thank you. Will you be here any other time?"

"I normally work Tuesday through Saturday. I get here at five and I leave at three in the morning."

"Good to know. I might look you up again some time."

"Ask for Monty."

"I can do that."

With one last look at me, he smiled and walked out the door. I went to the bathroom and showered, put my speedo back on and went out to tell the boss I was done with work for the night. He didn't give me any shit. He saw who I had taken into private and didn't question my reasoning. That gave other dancers an opportunity to make a few bucks too.

I went home and chilled for a while, before calling it a night.

So at this point you probably think this story is finished. Fate can be tricky. Fate can be funny. And fate can sure as hell be the biggest joker in the world.