12 comments/ 85653 views/ 15 favorites When the Boss is a Bear By: Cymon 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. When the Boss is a Bear Ch. 02 Tony tossed the package on his desk in front of me. Simple brown paper wrap with a strip of packing tape to hold it together. It had been a month since my boss Tony and I had had our first night of man to man sex in an out of the way hotel on a business trip. That time he'd ended up putting me in a pair of crotchless panties and fucking me hard. I was beginning to think he'd tossed it off as a one- nighter, much to my disappointment. Tony and I had been finishing up the project schedule for the next contract that Tony's paving company was working on. I put my clipboard aside and looked down at the package curiously. Tony pointed to the small parcel and looked at me, a strange glint in his eyes. "Take it home, open it there, put'em on and wear 'em... all day tomorrow. Got it?" he asked looking at me intently. Mystified, I nodded and tucked the package under my arm. "Good," he continued in his gravely voice, "enough work today. You go home now." With that Tony bent over his papers and seemed to forget I was there. I shrugged and headed out. Tony was a self-made man, worked his way up from road crews to starting and building his own company. I'd grown used to his abrupt, seemingly gruff manner. I knew from experience that Tony was a hard man but fair and we found we worked well together. Me handling the books while Tony pulled it all together and made it work. As soon as I got home, I opened the plain, brown paper parcel. Inside, wrapped carefully in thin clear plastic was a pair of black, fishnet stockings. They were thigh high stay-ups with a back seam. Folded neatly under the stockings was a shiny, black latex panties. I quickly stripped off my clothes and put on the stockings and the panties. They fit perfectly - and felt marvelous. I admired the view in the full length mirror for while until I finally had to go and masturbate. I was careful not to cum on my new outfit or damage it in any way. The next morning, I climbed into my pickup wearing Tony's gifts under my jeans and red flannel plaid shirt. It made me feel secretive and sexy. When I got to the work site I parked my car at the far end and walked towards the big trailer we used as an office as we moved from job to job. At 6am most of the road crew were already there downing the last of their coffees before they got to work. All of them waved and we exchanged the usual greetings but I felt incredibly horny and wondered if they could read it in my face or hear it in my voice. And I especially wondered what they would say if they knew what I was really wearing under my dusty work clothes. I had the feeling as I climbed the steps up to the trailer that one guy in particular, one of the biggest fellows, our foreman John, was staring at me but I put it down to the sexual fever running through my veins. Inside I collected the schedule and inventory accounts for the day and went into Tony's office. He was already there of course. In all the time I had worked for him, Tony had always been the last to leave and the first one in every day. He nodded as I put the black coffee I had brought for him down on his desk. I waited patiently as he worked through a progress report form. Finally, he put down his pen and looked hard at me. "Well?" he asked, his eyes boring into me. I knew what he was asking. I stepped around to the side of his desk to where he could see, then I leaned over and hiked up one leg of my jeans a couple of inches, just enough to let him see the fishnet stockings. He grunted his approval, handed me the progress report to finish up and dismissed me with a wave of his hand. It was month end so I had my hands full with paperwork until about noon and by then Tony had left to meet with some suppliers. He got back around four and indicated he wanted me to hang around for a while - like I was going to leave anyway - I'd been like a bitch in heat all day and I wasn't about to go home feeling that horny if I could help it. Throughout the day I had grown more and more conscious of the stockings sheathing my legs and my cock straining against the latex panties. Just after five and Tony was still in his office and my lust was about to boil over. Then in walked John. 'Great,' I thought, 'another delay.' John nodded to me and smiled. "Hey man, don't let him work ya too hard," he said with a grin, "He still in there?" Again I saw that curious look in his eyes and I wondered for a moment if he could read the secret in my eyes. I quickly dismissed the ridiculous thought just as I had earlier this morning. "Hey John, yeah he's still there," I replied with a wave of my hand. "Great, he wanted to see me before I headed out," exclaimed John, "Might head out for a beer later if you're interested." "Sounds good, see you later," I answered as John headed into Tony's office, closing the door behind him. I heard the murmur of their voices for a while, then John came out, smiled at me and left. Tony called me in and told me to leave the door open. He folded his big, rough paws on his desk and said one word. "Strip." I was out of my shirt, jeans and work boots in a flash. Tony nodded approvingly. He motioned for me to turn around and I quickly did as ordered. I stood there with my back to him, slowly running my hands up and down my silk covered thighs, waiting. Finally he told me to turn around again. He was standing behind his desk, stark naked, his clothes tossed carelessly in the corner. Once again, I admired his squat powerful body, covered from the neck down with thick curly black hair. The furry covering still did not hide his rugged body and short, solid cock. Tony beckoned me over to the couch by the wall that he often slept on when he worked late into the night. Tony laid back and I quickly bent over his cock and went to work on it. I watched as Tony closed his eyes while I wrapped my lips around the head and tongued it hungrily. I felt his hand reach for my leg and begin caressing it through the fishnet stockings. That only fueled my lust and sent my mouth plunging onto his cock. I took him right up to the hilt, until my nose was deep in his pubic hair and the smell of his sweat and manhood filled my nostrils. My lips slid happily up and down along the length of his engorged shaft as I caressed his balls lightly. He grunted as his hand roved up and down my thigh. I sucked him greedily for several minutes, enjoying the feel of his rod pumping into my mouth until he pushed me roughly off him. Tony got up off the sofa and got a tube of lubricant out of his desk drawer. I knew what was coming. He bent me over the arm of the sofa and ran his rough hands lovingly over my latex panties. Then he yanked them aside and pushed a handful of the cold lube into my ass. Tony worked the lube in and around with a couple of his big fingers which also loosened me up good. There was a brief pause as he worked a condom over that delicious big cock of his and then I felt the mushroom head of his cock at the entrance to my hole. Tony pushed slowly in. There wasn't as much resistance as the first time he fucked me and I spread my legs wider to help him. A few seconds of pain and pressure and then Tony was in me. I moaned softly with delight at the feeling of his thick rod filling my tight ass. Tony stayed still, impaling me on his manhood, both of us taking a moment to enjoy the feel of our bodies joined like this. Inevitably and happily for me, Tony finally began to pull out and push in, over and over, working himself up to a comfortable rhythm. I tried to meet his thrusts but most of the time I just went along for the ride as he pounded into me. All the while he was grunting happily and his hands were caressing my legs in the fishnet stockings. There was a noise at the door behind us - I looked back over my shoulder and was startled to see John, standing in the doorway, buck naked and stroking a long wet cock in his hand while he watched Tony ram my ass. Tony glanced back at John briefly and acknowledged at him with a grunt. Two long strides brought John to our sofa where he deftly slid himself onto his back and under me, his proud cock right under my mouth and pointed upward, just begging for attention. John's long, strong body, unlike Tony's, was smooth and almost hairless yet still rippling with muscle. I was too overcome with lust and Tony's big cock deep in my ass to be bothered to stop and wonder at John's sudden appearance, and or the fact that he was naked no less! Tony went balls deep in me and held it there as I eagerly went down on John's long cock with my mouth. Tony resumed his jackhammer pounding in my manhole and John quickly caught the rhythm, lifting his cock into my mouth at the same pace. I felt like a complete and utter slut. My fishnet stockings were ripping under Tony's rough pawing but I was beyond caring - if anything they just made me feel all the more wanton. I briefly became aware that Tony had long since torn off my panties and discarded them with little ceremony when John had entered the room. John's hands clamped onto the sides of my head and he was soon wildly fucking my face, adding his own moans to mine along with Tony's guttural grunting. John suddenly pushed my mouth off his cock as ropey jets of his seed erupted from the head of his cock and sprayed all over my face. Spurt after spurt of John's cum splashed onto my face and hair and by the time his cum volcano finally subsided, my face was covered and dripping. This seemed to inspire Tony. As John slipped out from beneath me Tony picked up the pace and begin fucking me with greater urgency. John stood to the side, watching with an approving smile and stroking his cock back to life, as Tony drove long, brutal strokes into my eager ass. I glanced over my shoulder in time to see Tony throw his shaggy head back as he plunged in to the hilt and convulsed in orgasm, cum surely pouring into his condom. He stayed deep inside me as the jism pumped out of him in shuddering waves. John meanwhile, had also pulled on a condom and lathered his long, erect cock in glistening lube. As soon as Tony pulled out of me and stepped back, John was on me in a flash. I soon felt John's pole sink slowly into my manhole. His longer, slimmer cock was a different sensation from Tony's shorter, thicker rod but no less pleasurable and I wiggled my ass appreciatively once he was all the way in. Also unlike Tony, John's strokes were slow and measured, allowing me to savor his languid fucking style and give my well-used ass a chance to recover and enjoy the moment. John briefly caressed what was left of my fishnet stockings before reaching around to stroke my rock hard cock. I was so aroused that it was only a minute or two before I gasped and exploded into his hand. He smeared my own cum across my mouth and face and I lapped at the cum in the palm of his hand like a thirsty animal. Satisfied, John then reached forward and grabbed a handful of my hair while his other hand clamped onto my shoulder. His fucking took on a more frenzied and determined pace. He pulled my head back, lifting my chin high while his long, deep strokes became faster and harder. Tony was over by his desk, still naked and stroking his cock watching us silently. John began panting as I moaned and gasped each time his long rod plunged deep into me. Faster and faster, harder and harder, until I began to think my ass couldn't take much more. John pulled out, rolled me over onto my back, tore off his condom and let a stream of thick cum splatter across my chest and face. At the same moment, Tony, now standing next to me also let loose a torrent of cum over me. As the two men finally finished, they stepped back to admire their handiwork. My fishnets were in tatters, pools of cum were dripping off my naked body and face. John had a wide grin from ear to ear as he looked over at Tony who had a digital camera in hand and was snapping a couple of shots of me laying exhausted, wet and happy on his sofa. He grunted contentedly as he put the camera down and picked up his clothes to get dressed. John tossed me a towel and smiled. "Come on," exclaimed John, "get yourself cleaned up. I definitely owe you that beer. Man, what a great fuck you are." I mumbled my appreciation as I sat up and looked over at Tony. I could just tell by the look on his face he was already planning our next event.