tagMatureThe Work Contest

The Work Contest


I finally did it. I asked my girlfriend to marry me and she said yes. We are both 24 and had been together for a few years. This morning I was going to tell all my coworkers that I was now engaged. I had no idea that the response from a select few would give me more pleasure that I could ask for...

Wednesday afternoon one of my coworkers Kim came up to me asked if I could join her and some other women I work with for drinks on Friday night. They all wanted to hear how I proposed first hand and not passed along through the office. Out of everyone I worked with I had easily masturbated the most to Kim. She is in her late 30s with a great set of tits on her. Even a few times I had snuck off to the work bathroom to do it because I couldn't wait until I got home. I told her that I'd love to and she could invite anyone else that was interested.

I showed up at the bar and much to my surprise there were six women there. And each one I had fantasized about while I've masturbated. I'll give you a few details on each, in order of how many times I've jerked off to them...

Kim, married, late 30s, nice chest, I think she is wild in bed.
Donna, divorced, early 40s, great ass, very small tits,
Trudy, divorced, mid 40s, a little plump, but always shows great cleavage
Jane, married, mid 40s, big, but huge tits, flirts with me the most
Teresa, married, late 40s, no tits, but I bet can suck dick like a pro
Heather, newly married, early 30s, big ass but a great rack

I gave them all the details and we joked around about everything for a few hours. After a few rounds of wine and beer the talk turned to sex. Everyone gave me a hard time reminding me that I was stuck with only one pussy the rest of my life. I was real drunk at this time and I opened my big mouth and asked if I could still keep masturbating to all of them. After a few minutes of a very uncomfortable silence, Donna spoke up and asked if I really jerked off to them. I told her all the time, even sometimes in the work bathroom.

I was so red with embarrassment at this time that I said I had to get home. I spent the whole car ride home hoping that all would be forgotten by the time I got to work on Monday.

Monday morning I went straight to my desk and opened my e-mail. There was a message from Kim to me and everyone else that was at the bar Friday, the subject was...The Contest. It said...

Dear Nick,

Thank you for a wonderful night on Friday. We all wish you and your fiancé lots of happiness. However we want to apologize for giving you a hard time about only having one pussy for the rest of your life. To make you feel better the six of us came up with a little contest that hopefully you will want to be a part of. We all will give you one night with each of us, anything you want to do sexually with us goes. All we ask is you tell us who was the best fuck, the best cocksucker, and who has the best tits. Think it over and if you agree respond to this e-mail with the word yes. Nothing will be spoken outside of e-mail.


Kim, Trudy, Donna, Jane, Teresa, and Heather.

I hit reply and typed the word yes in instantly. All I would have to do is press the send button and the contest would be on. My dick was already leaking precum and was asking to be played with. I pressed send and walked into the bathroom to enjoy another orgasm thinking about the contest.

It was now Thursday and nothing had been spoken about the contest, I was starting to think it was a joke. Then I received a new e-mail from Kim with a schedule of who I'd be with when. The next six Friday nights I would be enjoying a new coworker's pussy. The order went Trudy, Jane, Donna, Teresa, Heather and Kim. For each of these six "dates" the woman would take me out to dinner and then we would go to the nearby motel to spend the night together. After the final date I had to send out an e-mail with the awards that I had promised to give out.

Friday night I met Trudy and we had a nice dinner together. It was more awkward than I thought it was going to be. Trudy has a great personality and I've always thought out of everyone at work that I had the best chance of fucking her. She is a little on the bigger side and has saggy tits, but she does like to show off her cleavage more than anyone in the office. Over dinner she told me she didn't care about the best tits awards, she knew she had no chance, but she wanted to prove she could suck and fuck better than anyone else in the contest.

We wasted no time at the motel and were tearing each other's clothes off right away. I told Trudy how I loved her cleavage and how I enjoyed jerking off while thinking about it. She unbuttoned her blouse and undid her bra. I was right about the saggy tits but they were still nice. I took one in my mouth and the other in my hand. Trudy immediately noticed the bulge starting to grow in my pants. She took down my pants and underwear and started to slowly stroke my 6" cock. My hand left her breast and moved down to undo her pants. I made sure to keep her panties on and slid my hand down the front of them.

I wasn't surprised when my hand felt the hairy bush inside her panties, but I was amazed at how wet everything was. Trudy started to moan as I rammed two fingers inside her. Then she pushed me down on the bed and started to suck my cock. I haven't had a lot of blowjobs in my 24 years but this one was nice, not the greatest, but still real good. Trudy took her mouth off my cock and asked that if she swallowed my load would she have a chance at the best cocksucker award. Before she could even put my dick back into her mouth I started to come. The first blast landed on her cheek, then she quickly put it back into her mouth to eat the rest of my cum.

I was still hard and was ready for some pussy. Trudy laid down on her back and I removed her panties and was careful to put them where I could retrieve them later. I wanted to keep a treasure from each meeting in this contest. Since this contest was all about me and her pussy was so hairy I decided to not go down on her. Instead I slid my dick inside Trudy.

It took only minutes until she was moaning and moving all over the bed. I knew I had given her a very pleasurable orgasm. But I still had a ways to go. We switched position and Trudy got on top of me. She rode me while I kept feeling those saggy titties. I started to get that feeling where my money shot was soon approaching and I wanted to cover her tits with my cum.

I grabbed her and threw her back down on the bed and went to town on her pussy. I was getting ready to bust my nut and I pulled my cock out and shot another fantastic load all over her tits. I then moved up next to her and licked all my cum off of her tits.

We just had a great time together, but then it was pretty awkward. Trudy started to get dressed and was a little mad when I said I was keeping her panties. She finally let me when I told her it might help win an award. They were a nice black satin pair, kind of big though. She got dressed and gave me a nice kiss on the cheek and thanked me for the night and left. I was still laying naked on the bed with her panties in one hand and my cock in the other. I masturbated while smelling her wet panties and thinking about what had just happened. Then I grabbed a piece of paper on the nightstand and wrote down her grades for the night.

Breasts C+
Cocksucking B-
Fucking B

I got dressed and started to think about my "date" with Jane next Friday...

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