tagGay MaleWhen the Boss is a Bear

When the Boss is a Bear


Tony put the beer back on the bar.

"That was a long day eh?" he said shaking his head. I nodded agreement as I sipped my own beer.

Tony was a self made man. At the age of fifty now, he had built up his own paving company over the past ten years into a thriving business and still insisted on being present at any new contract meetings. For the past year I had handled his accounting, payroll and general office management. Tony insisted on bringing me along whenever he went to meet clients on new contracts.

We had spent the day in meetings with the roadworks staff for a mid-size town about a four hour drive from the city where we were based. It had been a long drawn out day wading through bureaucratic red tape and reassuring various administrators that we could bring the project in on time and on budget. This is where Tony and I worked best as a team - he had the firm handshake and years of experience while I could spin out numbers and schedules that satisfied the most exacting clerks.

We'd finally wrapped up about six pm and Tony had decided he didn't want to make the long drive back on the rural roads at that hour. So we booked into the one decent hotel in town. The hotel only had two rooms left, a suite and another with a twin bed. Tony offered me the suite but I passed and he shrugged and booked us in. Then we hit the pub downstairs for supper and drinks. We had some laughs and the beer went down good.

Around eight we headed off to our respective rooms. I stripped down and decided to watch some TV for a while before I hit the sack. About twenty minutes had passed when the phone rang. It was Tony.

"You gotta come up and see this room. For a town way out in the boonies, this is something, got a hot tub and a big TV. I got some beers. Come on up!" Since I wasn't that sleepy yet I agreed, pulled on sweatpants and a tshirt and headed upstairs.

Tony met me at the door in a thick white hotel bathroom. It looked like he was otherwise naked. He handed me another robe and said to get comfortable while he got the beers. 'Ok,' I thought, 'what the hell'. I went into the bathroom, tossed my clothes and put on the robe. When I came out Tony handed me a beer and waved his hand around the room. I whistled. He wasn't kidding.

It looked like the hotel had invested most of their money in this one room. Big screen TV, hot tub (already bubbling with hot water), a small kitchenette and a king size bed. We settled on the sofa in front of the TV - Tony had some sort of porn movie running. I was cool with that. Tony said it was the only decent choice on the pay-per- view menu. I was a little surprised when the guy fucking the girl suddenly found himself being fucked at the same time by another guy but after a while I found myself fascinated. All the players seemed to be having a great time fucking and being fucked.

"Hey", said Tony after a while, "how about we watch this from the hot tub?"

"I didn't bring a bathing suit", I said with a shrug.

"Me neither," laughed Tony as he stood up and dropped the robe. Tony was about five foot six, stocky solid build with a bit of a belly. He had clean-shaven face but otherwise was covered over the rest of his body by thick black hair. I couldn't help noticing his cock. It was probably about five inches and thick. And hard. It kind of looked like a big thick hairy sausage. Sounds crazy but that was what flashed through my mind. He grinned and climbed into the hot tub. Unlike Tony, I was tall and slim, a good four inches over his height but he had about forty pounds on me.

I realized I was starting to get a good buzz on from the beer as I tossed my robe and climbed in next to him. The steaming hot water felt so good, I put my beer down and leaned my head back, opening my eyes now and then to check out the action on the TV. By now the girl had put on a strapon and was pounding one of the guys in the ass as another guy drove into her cunt.

"Pretty hot huh?" asked Tony. I could only nod as I watched this fuck sandwich in progress. The whole girl-guy-guy thing was giving me a raging hardon and I wished I could just take it in hand and stroke it, but I wasn't sure how Tony would take it.

I know what you're thinking and looking back, I should have realized I didn't need to worry but at the time... well you get the point.

Suddenly I felt a hand on my thigh. Startled I looked at Tony. He had a smile and a quizzical look in his eye.

"Great movie?" he asked again. I looked back at the TV and his big callused hand slid further up my thigh. My cock was standing straight up now in the surging jets of water and Tony's hand soon found its way to it. I felt his thick fingers close around it and begin to stroke it. Man it felt good. His hand around my cock, the hot water gushing around our naked bodies and these three people on TV fucking and sucking every which way.

Then, although my eyes were still glued to the TV and as if it had a mind of its own, my hand reached over for Tony's big cock. I found it and began stroking him. His cock felt marvelous. Thick and strong and soft. Not like my longer, slimmer and almost hairless cock that Tony was managing so expertly.

The TV snapped off and I turned to see Tony put down the remote, never missing a beat as he worked my rod. He smiled, leaned over and pressed his lips against mine. I hadn't done this with a guy for many years. I found myself kissing him back as his tongue pushed between my lips and began exploring my mouth. Our tongues dueled each other as I moaned and he grunted. He kissed me harder and I met his intensity with a hunger of my own.

At last he broke our kiss and told me to sit on the edge of the tub. By now the timer on the hot tub's jets had expired and the whirlpool of water was calming but I barely noticed. As soon as I had lifted myself dripping out of the water and sat on the edge Tony had slipped between my legs and grabbing my cock again guided it into his mouth. It felt better than any blowjob I had received from a woman and maybe even better than a few pussies I'd fucked for that matter. I instinctively put my hand on Tony's head through the shock of thick curly black hair as his hot mouth slid up and down my cock. It was heaven.

Time after time he'd bring me to the edge then back off, nibbling the head of my cock and sucking on my balls to keep me from cumming, he was totally in control. He lifted my legs over his shoulders and proceeded to lash his big tongue between my cock and my ass. A few times I felt the tip of his tongue dart a little way into my hole. I was moaning and quivering the whole time.

Finally he slipped out from under my legs and took me back into his mouth. As I watched my cock slide in and out of his mouth I sensed this time there would be no turning back. I felt his strong hands reach around and grab my asscheeks hard, his fingers digging in as he began to deep-throat me. I'd lost all control at that point and Tony knew it. He stepped up the pace, driving my dick in and out of his mouth eagerly. As he felt my balls tense up and heard me gasp he went deep on me and held my cock right up against the back of his throat as blasts of my seed exploded out of me. Tony swallowed every pulsing load as I called out his name in lust. He eased off at last and stroked the last drops into his mouth.

Then he looked up. "Up for more?" he asked with a grin. I was still shaking but I managed a weak nod.

"Good," he said, "let's get out of here and towel down a bit."

I got out of the tub and quickly dried off. Tony went to his bag and I watched every muscle ripple in his big hairy back. He came back smiling and held out a pair of crotchless black lacey panties.

"How would you feel about wearing these for a bit?" he asked.

I thought about the girl in the movie. "Ok," I said with little hesitation. He smirked.

"Kind of like the idea don't you?" Tony said with a leer to which I nodded with a faint smile of my own.

"I knew it, bought them with you in mind", he replied in a husky voice, "go ahead, snug them on."

I quickly slipped them on while Tony watched approvingly. He went over to the king size bed and lay on his back spread eagle.

"C'mere baby," he said, "suck my cock". You didn't have to ask me twice. I was on the bed between his legs in a flash. I couldn't resist running my fingers through the hair on his belly and chest. His eyes closed when my fingers reached his chest. I got the message. I began playing with his nipples, rubbing, twisting and teasing them. Tony was making small guttural sounds in his throat. I leaned forwarded and closed my lips over one nipple. He arched his back, pressing his chest against my face and his nipple hard in my mouth. I licked and sucked it, gently nibbling it between my teeth now and then.

"Yeah baby, that's it, I like that," murmured Tony in a deep voice, his eyes still closed.

My hand found his fat cock and stroked it slowly while I worked his nipples, switching between one and the other every few seconds. I loved the feel of his chest hair against my face and in my mouth as my tongue slid back and forth across his chest from one nipple to the other.

When I felt I had done all I could for his nipples I moved back down to his cock. I looked at it in my hand, so thick and big. I wanted it. I lowered my mouth to it and took him deep into my mouth on the first stroke. Tony groaned and lifted his hips trying to get even deeper. I fought the sudden gag reflex and made my throat muscles relax, letting his cock sink in until my nose was right up against the lower half of his round belly. His hips sank back onto the bed and I started in sucking his juicy cock. I felt his hands settle on the sides of my head as he began to slowly fuck my face. We went at it like this for several minutes until Tony stopped. I looked up.

"I need to be inside you now," he said breathlessly.

I looked down at his big cock and thought of my long untested ass. "I don't know if I can handle that Tony," I said uncertainly. He nodded.

"Don't worry, I'll go slow, we'll take it easy and I'll quit anytime you say so."

I looked down again at his beautiful wet cock, still shiny with my saliva and felt a flame of lust lick through my body.

"Alright," I said looking into his dark eyes, "I'll try."

Tony slipped off the bed and went to his bag a second time. He came back with several condoms and a bottle of lube.

"Came prepared I see?" I said with a smile.

"Always ready, that's me. Now get on the bed on your hands and knees."

I quickly complied, fighting back the nervousness.

"Don't worry. I'm gonna loosen you up some first. You'll see, you'll love it."

I felt him pull the panties down. I looked back over my shoulder and watched as he squeezed a big dollop of clear lube out of the plastic bottle. He smeared some between my cheeks and started working it into my hole. Gently, slowly, he began working the lube in deeper with one finger. I spread my legs a little wider.

Tony paused. "Ok?" he asked. I answering by spreading my legs a bit wider again. I felt his chubby finger go back to work on my ass. Before long he had me loose enough to admit a second finger. Tony worked the two fingers in for several minutes, stretching and pushing. Occasional glances back told me he was stroking himself with his other hand at the same time. When he had managed to get two fingers all the way in with no protest from me he stopped.

"That should do it," he said, "I think you're ready now." He quickly slipped on a condom.

He pushed a last big dollop of lube into my ass then poured more into his hand and worked his cock in it. I looked straight ahead and focused on relaxing. I felt him slid my panties back up over my ass. The silky material felt great as it moved up my thighs and I wiggled my ass appreciatively. Tony chuckled. I felt him gently spread my asscheeks and then I felt the head of his cock at the entrance to my manhole. For a second I almost panicked it felt so huge back there but Tony had done his work well and as he began to push it seemed to slide easily. That feeling didn't last long.

Soon enough his fat hairy cock was stretching my ass, pushing to gain deeper entry. I dropped my head as the pain got worse. Tony saw it and pulled out slowly. He worked some more lube into me and onto his sheathed cock. He seemed to be waiting. I lifted my head and pushed my ass back toward him. Once again I felt his cock slip into the slit in the panties and push against my hole. I realized I really wanted him in me and I was determined to have him this time.

Tony pushed in steadily, my ass yielding more readily this time. As his cock went deeper I fought against the growing pain, against the feeling that he was going to split me wide open. When I thought I couldn't take it anymore and I was going to have to make him stop at all costs, he was suddenly through and I felt him fill my ass. And I do mean fill. It felt like there was a massive pole up my ass, it still hurt but the pleasurable feeling of being filled was rapidly overtaking the pain. He stayed that way for a few moments, giving my ass time to adjust to his thick rod.

I gradually became aware of the feeling of his hairy chest on my back and his big hairy thighs tight up against mine. I moaned softly. It was like having a bear on my back.

I felt him begin to slowly pull out and I wanted to yell at him not to quit now. But he wasn't quitting, not at all. He went back a couple of inches then pushed in again. He kept up this slow leisurely fuck for several minutes. All the time he was grunting and saying things.

"Yeah baby, what a hot ass..."

"Nice and tight, just the way I like it..."

"Taking it like a good little slut, yeah..."

I soon found that he liked it when I would push back to meet his thrusts now and then. His hands often caressed my asscheeks through the silky material of the panties as he pumped his cock in and out of me. Once in a while he would sink deep into me and stay there and I would feel his stubby fingers searching out my nipples and pinching them lightly. It was marvelous.

My lust soon grew to the point that I wanted his cum and I picked up the pace as I pushed back onto his cock. He got the idea and began fucking me faster, harsh growls and moans coming from him. My own moans were coming hot and heavy as he really got into it, pounding my eager hole. I cried out as I came again. Tony paused and quickly grabbed my cock, catching some of my cum and rubbing it across my nipples. Then he was back at it, more urgent than ever. I was desperate for him to cum.

"Come on Tony, fuck me. Yeah fuck me so good. Cum baby, cum..."

Tony growled and grabbing my hips, began driving his thick cock into me hard and fast. Now he was fucking me like a wild animal, grunting and slamming into my ass and I was loving every minute of it. We were both moaning and howling and then he came. He drove it right in to the hilt and exploded. I could feel his body cover me as he filled the condom, then he suddenly pulled out, pushed me on my back, ripped off the condom and let his cum shoot across my naked body. I watched with delight as ropes of his seed landed on me and as they landed I was smearing them all over me - on my cock, my stomach, my nipples, my face. Tony shuddered as the last spurts jetted out then he collapsed on top of me.

I wrapped my legs around his waist as his lips met mine and we kissed lovingly. He slid his furry body a little up and down on mine mixing his cum with our sweat. Finally he rested on top of me as I caressed his back and kissed him softly. After a few warm, delicious minutes he rolled off and we went to sleep but he was "up" again early and gave me another good morning fucking before we had to shower and checkout.

As we left the room he gave my ass a hard squeeze and said with a lewd grin, "Next time, we try stockings. Or maybe some nice latex?" I couldn't wait.

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