Raising the Stakes on a Dare

This parallels my other story 'How To Thank Tech Support'. You don't need to read either to enjoy the other, but more information is revealed if you read both.

****

I'm a 30 year old woman with short red hair. I work at an investment firm on the third floor. This was where we broker deals and make large sum investments for our rich clients. And we get 10% of the earnings -- so there is a lot we'd do to make sure our clients closed the deal and didn't go to another broker. I've sucked a few cocks in my time, my clients always came back to me.

Another thing we often did was play dares with each other -- for large sums of money. Just the other day we dared the one girl to strip down naked and walk out on the balcony. She had a hot body with a tight ass and pert breasts, she got a rise out of everyone that day. And she scored a couple grand because of it.

I was chatting on skype with one of my male collegues down the passage. He was an attractive man, well built, dark hair, light tanned skin. We had the webcam on, and he was trying to think of something he could get me to do for two grand.

He asked me to show him my pussy and let him record a video of me playing with it. It was a fun idea, but I wasn't about to give him something like that just for money, so I suggested that I'd do it for the money and a video of him playing with his cock.

We agreed to it, and we always honour an agreement. So I switched the cam to record, and so did he. I started by standing up. I had a tight top on, showing off my pert breasts and aroused nipples and I didn't have a bra on. I had a leather miniskirt on. I hiked up the skirt to reveal red lacy panties. I lowered them down and brought the webcam in for a closeup showing off my pussy that many guys have said was the cutest they'd ever seen. I shave, leaving only a small strip of hair above it.

My collegue stood up as well and opened his pants. He pulled out his cock, which quickly hardened, and started stroking on it. From what I could see he had a very attractive slightly thicker and not too long cock with a nice mushroom head. I always have the most fun with those, the feeling of it moving in and out of my pussy is always sublime.

I lifted one leg and made sure the cam got the best action shot. I pushed in a finger and started rubbing my pussy and used my thumb to stimulate my clit. I went for the quick finish and brought myself to cum as quickly as possible.

I told my collegue that he must have something better than this. He said that he'd pay six grand to see me suck cock. I asked him whose cock I should suck, and he said that maybe I should invite someone up from the geek squad downstairs. By that he meant the hardware maintenance nerds. He typed a grinning smiley as he said that any of those virgins would be thankful for a blow.

It was easy to simulate a problem. I figured I'd unplug the webcam cable, this would let me fiddle with it under the pretense of checking it, so that my collegue would be able to watch. I called down to the department and asked for a guy to be sent up urgently, making up an excuse about an important conference.

It didn't take long for one of them to show up. He did look like a bit of a nerd, and he had that self-conscious nervous posture that gave away his lack of experience. But at least he was somewhat cute.

I could see him looking me up and down, probably memorizing my figure for a jerk fantasy later. I pointed him to below the desk where the computer sat, and watched him crawl under. His ass was looking back at me, and it was a good looking one as well.

I leaned back and made sure my legs were spread. I could still feel the moisture on my pussy from the fingering earlier. He quickly found the problem and plugged in the cable. As he crawled back out he looked at me and I knew he saw my pussy. He was completely nervous and stammering.

He got up and moved behind me as I moved the chair back to the desk to check the webcam was working. He'd sat down on the window sill, and I couldn't have planned it better. I made sure the cam was running and made sure my collegue was watching. I pointed the cam to look at where the guy was sitting on the sill.

I turned back to him and told him it seemed to be working fine. I rolled myself forward on the chair slowly. I told him how much I appreciated it that he'd fixed the problem. Before he'd realized it, I had him trapped against the sill between my legs and I put my hands on his knees. I asked him if there was anything I could do to show my appreciation, but he wasn't bold enough to ask. He stamered something about not needing any thanks. I thought it rather sweet under other circumstances, but right now I was trying to get him to pull out his cock and ask for a blow.

I'd have to try something more direct. I told him I know I saw him looking at my pussy. I asked him if he'd enjoyed the view. He started stammering more. So I moved my hand to his groin, and squeezed gently. I could feel his cock already hardening. I undid his pants and pulled out his cock. It was a nicely shaped and decent sized one. I told him that I liked it, and especially the fact that it wasn't circumcized. Its simply not natural to go snipping around one's genitals.

I started stroking it, moving the skin up and down. He seemed paralysed by the circumstance, I think he really had never had this happen to him before. I decided to make it something really memorable for him. I put my mouth down around his cock and started sucking on it, moving my head up and down. I moved my tongue around the underside of the head, and then I lifted my mouth off and licked the underside of his cock down to his balls. It didn't take him long, I could feel him about to cum. I moved my mouth back onto his cock and felt his cum spewing out his cock. It was a decent amount, more than most guys. I had to swallow twice to get it all down.

I told him that it was nice, and he should be proud of himself. I carefully pushed his cock back into his pants and zipped them up. I then told him I needed to get on with the important meeting and got him to leave the office. He mumbled a thank you, which again I found very sweet, as he stumbled out.

I moved back to my pc and asked my collegue if he'd enjoyed the show. He was stroking his cock and said it was amazing. I was horny as hell so I asked him if he'd like a fuck if we made the figure he owed an even ten grand. He quickly said yes, and I invited him to my office. He almost raced down the passage. Luckily we have smoky glass that doesn't allow you to see into the offices.

I pushed him into the chair, and undid his pants. He hadn't even bothered zipping them before coming here. I pulled out his cock which was already oozing precum, and gave it a quick lick. I then sat down on top of his lap and slowly lowered myself onto his cock. His cock felt great inside my pussy, that mushroom head stimulating my pussy.

He lifted up my top and started licking my left nipple. I leaned my head on his shoulder and put my arms around him. I then ground up and down, feeling his cock penetrating me. I was so horny from the experience that I quickly came, and as I did he began groaning as well and I felt his cum entering my pussy.

I whispered into his ear that I'll refund half if he licked his cum out of my pussy before leaving. He said it was a deal, and I stood up, holding my pussy closed with one hand. He quickly stood up and I sat down on the chair, leaning back, spreading my legs. He got down between them and licked at my pussy. I relaxed my muscles and let his cum flow out, and he lapped it all up. He then stood up again and asked me to give his cock a quick cleaning. I leaned towards it and licked it all over, cleaning off his cum and my juices. He closed up his pants and retreated out the office. Unlike the kid, he didn't say thank you - but then, he did pay five grand for the experience.

I made sure my clothes were straight, and sprayed on some perfume to take the smell of sex away. I couldn't find my panties, I think my collegue must have pocketed them at some point. Then I checked my video folder and made sure all the action was saved. I even had a nice image of my collegue with his cum running into his mouth. We might always honour agreements, but we were never above a little blackmail.