The Stupidest Bet

I can't believe that I lost that stupid bet!

For the last few years, I have worked as a crew leader for a roofing company.

I know what you're thinking; why would a pretty, thirty year old woman, choose to spend her summer days, reshingling roofs?

Well, it's not really complicated. I like to be outdoors, the work keeps me in fantastic physical condition, allows me to maintain an awesome tan and I get to have fun teasing the horn-dog guys I work with.

I do tease them often, wearing the shortest booty shorts that I can find and usually just a bikini top, to work. Every once in a while, I've been known to let a nip slip, but nothing more revealing than that.

But I'm not above the verbal jabs of 'lockerroom talk', that guys always seem to get up to. I love to see the look on the faces of my crew, when I talk about some crude sex act. Invariably, the guys seem to find it necessary to readjust themselves, after some of my raunchy talk. I love that.

Well, now my big mouth has gotten me into a bit of trouble...Last week, I made stupid a bet with another crew leader.

Joe's crew is the company's second most productive team, right behind my guys.

Wednesday afternoon of last week, my crew had completed three jobs and Joe's crew was only finishing up their first job.

"Hey Joe, I don't think you're gonna catch us this week." I gave him a condescending smirk, as our crew's worked to unload the truck's from the day's work.

"Yeah Carly, you got a pretty big lead on us," he said. "But I think we're gonna have a strong finish."

"Care to put some money on it?" I asked. "Make it interesting?"

"Now Carly, you know my wife would kill me, if I lost money on a stupid bet."

I laughed.

"Hey, now we could make it a little more interesting though," he said. His devilish grin made my nerves tense.

"Now Joe," I said. "You've been trying to get in my pants for years. I've told you that we are both married and I don't cheat on my husband."

"I know, I know," he held his hands up, to forestall my practiced response. "I had something else in mind."

"Yeah? What's that?"

"I thought maybe we could wager something as a reward for our crew's."

I should have known, from his smile, that he rigged the contest somehow.

Joe had set up small jobs for Thursday and Friday, for his crew. My crew spent both days completing a single job, on a giant house, near the beach.

By week's end, Joe's crew had finished up five jobs and my crew had only finished four.

When I made the bet, I knew there was no way I'd lose. It would seem that Sam, the company owner wanted to watch me pay off the bet and the two men had calluded against me.

Now, I'm standing behind Sam's desk, in his office, with the company owner, our receptionist Shirley and two full crew's of employees; sitting and waiting for the show I'd promised.

I don't welsh on bets, so I knew I'd go through with it, but damn.

Sam's desk was completely cleared off, for the show. Now a ten-inch, flesh colored dildo sat, suction cupped to the middle of the desktop.

I stared down at it, my eyes big, my nerves wound tight.

I took a deep breath and climbed up, on top of the desk. My Redwing work boots leaving dirty prints on the veneer finish of the desk.

Reggie, one of my crew, pushed a button on a Bluetooth speaker, he'd brought in. 'Porn Star Dancing', by My Darkest Days started playing.

I gave him a sarcastic smirk. Then, as if on their own, my hips started to sway to the music. I guess stripclub dancing is like riding a bike, because I immediately fell into my old routine.

I spun away from the guys, shaking my round little ass at them, then I started rolling my skin tight booty shorts down, past my hips and down my thighs.

My feet, naturally spread and I bent at the waist, pushing the shorts down all the way. I stepped out of one leg and then spun and kicked the shorts to my boss.

Now I was standing on my bosses desk, wearing only work boots and a bikini top, with nine coworkers and my boss, staring at my bare shaven twat.

They all cheered, having never seen my pussy before.

I knew that my already wet twat must be glistening in the light.

A couple of the guys pulled out their phones, to video; but I put a quick stop to that. They wouldn't get a video of today's show, it would be a one time show.

My hips girated and rolled, then my knees bent and I squatted down, just above the head of the monstrous dildo.

Now, I've riddenguys with cocks that were bigger than this fake phallus, but not by much. This thing was almost the same size as my wrist, it was a bit intimidating.

I reached between my legs, wrapping my fingers around the thick head. The dildo was already oiled up nicely, thanks to my preparation.

Placing the tip, at the entrance to my vagina, I gently pushed.

Pop! The thick head sank effortlessly inside me.

I felt the pressure, stretching me from the inside. A rush of erotic adrenaline filled my body.

My face and chest burned with embarrassment, when I looked up, into the eyes of my audience.

The embarrassment quickly faded and left me with only wanton desire, as I slid my soft pussy lips down the shaft of the dildo, sinking three quarters of the shaft, in my first attempt.

I placed my hands on top of my knees, pushing upwards, with my feet planted firmly on the desk; extracting the toy almost entirely, before pushing my body back down again.

My eyes closed a my head tilted back, relishing the feeling of being filled. I continued, slowly pumping myself up and down on the fake cock, four or five more times.

My ecstasy was temporarily interrupted, by the oohs and ahhs of the guys watching me.

When I opened my eyes again, I found several of them had pulled out their phones and were now filming my exhibition, disregarding my earlier warning.

By that point, my sexual desire overpowered my inhibition.

I've always been a bit of a closet exhibitionist. Now with all of these people watching me, the exhibitionist side really flared up. My slut-side was about to really show.

With my sexiest grin, I looked directly into my bosses camera phone, then I relaxed and slid all the way down the shaft of the dildo.

I pushed my feet apart more and slid them out in front of me a little, allowing me to lean back, resting my weight on my hands. My full pussy was now totally exposed to everyone in the room.

I glanced around the room and saw that none of the guys, or Shirley, were able to resist rubbing at their crotches. My desire ramped up even more.

I can't remember having ever felt so exposed, or turned on. I knew that my pussy was soaking wey.

I started to pump up and down the dildo, in earnest. My moans quickly filled the small office, as my excitement built.

Wanton desire pulsed through me, like I was a purely sexual being.

Shifting my weight to one hand, I freed up my other hand to push my bikini top out of the way, allowing access to my aching nipples. I squeezed my breasts, one at a time, then tweaked my nipples, pinching and pulling at them.

I felt the orgasm building, the burning in my clit and labia became almost unbearable, as I could think of nothing, but cumming in front of my coworkers.

When the orgasm finally rocked my body, I collapsed, backward on to the desk.

Even as waves of my ecstasy rolled over my body, I remember feeling the head of the dildo push out of my well-fucked cunt.

Screams of pleasure accompanied the shuddering orgasms, that pulsed through me.

When I finally started coming down from the organic high, I looked around at the room full of coworkers.

Every single one of the men around me had pulled out their cocks and were stroking them shamelessly, as they watched my slutty display.

My boss, who was standing directly in front of me, was covered in my ejaculate, as I had squirted a copious amount all over the man.

Gathering my courage, I slowly sat up and smiled shyly at the two crews.

•••

That was three weeks ago.

Every Friday since then, I seem to have to pay off some debt to the guys. I've never had a job that felt this rewarding.