When the Boss is a Bear Ch. 02

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The Boss brings a friend.
2.3k words
4.52
68.3k
18

Part 2 of the 2 part series

Updated 11/01/2022
Created 12/08/2006
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Cymon
Cymon
10 Followers

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.

Cymon
Cymon
10 Followers
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9 Comments
cdCindy1cdCindy1about 6 years ago
please continue

I can't wait to read more of your adventures with Tony, John and other big hunky men. Please write more stories. I can't wait.

AnonymousAnonymousabout 13 years ago
I wish my boss would fuck me

I wish my boss (who is hot & looks like he has a big cock) would fuck me and let me suck his cock. Your story has inspired me and maybe I'll try & make a move on him to see if he wants me. I'm such a cock-sucking slut that I wish all the men in my office would fuck me hard.

Please tell us more stories. They are great.

AnonymousAnonymousover 14 years ago
Big

I was sitting in my office,computer on, looking at a video of a tranny taking a cock in her hole.My cock was rock hard as the guy shot his load all over her back.switched off, went home.Next morning on my desk was a package with a note,see me in my office after you have changed into these.What, i looked around, i opened the package, sheer panties and pantyhose.Then a note, do it, signed Gary.The office manager, i went into the mens, changed and walked back, knocked on Garys door.Enter, i did, close it,good we need to go out.I followed him to his car, off we went,as we went along he said drop your pants,what, i saw what you were looking at on your computer, you know the office rules re porn, now drop your pants, i did, his hand went to my pantyhosed leg, rubbing gently up and down,my cock hardening.He brushed my balls, you like it, i thought so as we pulled into his driveway and into the garage.Get in front of me and walk inside so i can have a look at your pantyhosed arse.I did, up the stairs, into that room, now sit on the bed.You keep your job as long as you do what i say as he unbuckled his belt and dropped his trousers to show a semi hard cock,pushing it towards my mouth.I opened as he pushed forward,first time, as he grabbed my head and moved it back and forward,his cock now hard, i gagged, he slowed, then a steady rhythym, until he stopped, pulled back.On your knees,look Gary i havent done this before, you heard do as i say, i turned, onto my knees, his hand rubbing my hosed arse, sliding between my legs, rubbing my balls, my cock hardening.Then he lowered the panties and pantyhose,a oily finger pushing at my hole, around, in, around, in further, then more oil, in further then a short wait, then bigger than his finger pushing at my hole, slowly, pain, my hole would not open, relax, push out, i did and the head of his cock magically popped in.Aaaaagh, geez, stop as he eased back, more oil, then in a little further, back, oil, in and he kept doing this until his cock was all the way in me.Allright, your very tight as he eased back, then forward,slowly at first, then a little faster,my hole adjusting, the pain still there but duller, my cock hardening as he fucked up into me.Then he grabbed my hips and the pace quickened as he really opened me up,my cock hard, i touched it and thick ropey cumm spurted out of me, my hole clenching Garys cock and with one final thrust he released his sperm into my now fucked hole.When it was over, he told me to put the panties and pantyhose back on.We went back to work.I have to wear panties and pantyhose to work everyday.We leave the office and he fucks my hole.Once he did me over his desk in his office, i must say i like my new work.

barbie_jo_69barbie_jo_69over 16 years ago

Very well written stories, super hot, love to read chapter 3

MichelleWhoIsMichelleWhoIsabout 17 years ago
You have my panties all wet!

Loved both chapters! Will you be writing more soon? I hope so!

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