The Work Contest Ch. 02

It was definitely one of the more interesting weeks of work I’ve ever had. All I could think about was the contest and what I thought everyone was going to act like once I had them in bed. I enjoyed the night I shared with Trudy. I had masturbated to her so many times, I couldn’t believe I actually fucked her. It was about what I thought it was going to be like. I was surprised that nothing really changed at work, nobody said anything about the contest and the awkwardness had gone away.

Friday night I met up with Jane for our “date.” Jane is also a little on the bigger side but her tits are huge, I think she is in her mid to late 40s. She has always flirted with me and I always thought that if I pushed it just a little or got her drunk I could have my way with her. We had a nice dinner, she was very excited to get her chance with me and she let me know that she wanted to win every award I was going to give out, best tits, best cocksucker, and best fuck. Even while we were eating she had her foot grinding away at my cock, I was amazed I didn’t come right there in the restaurant.

Once at the motel we went straight to the bed. She got on top of me and we kissed like we had been lovers for years. She had her tits mashed into me and was dry humping like no tomorrow. My 6” dick was throbbing at all the attention it was getting. I started working on taking her shirt and bra off, I just couldn’t wait to get those huge tits in my hands. The black lace bra she had on could barely contain them. I let them free and instantly started sucking away. They were easily the biggest tits I’ve ever had the pleasure to suck on.

Jane was working on taking off my pants and underwear while I was sucking away. She had them down around my ankles and took my cock in her hand. She was barely stroking it when I knew it was too late. Those tits were turning me on so much I was going to come. The best part was I didn’t even warn her. She was going down to put it in her mouth when I unloaded. The first shot hit her right in the lips, the next on the chin. I was hoping she was not going to be angry with me, but I knew she wasn’t when she sucked it all down. There was still a little on her lips as she came up and gave me a kiss. I apologized for coming without warning and she said she was only disappointed that it didn’t end up inside her pussy.

I hadn’t even taken her pants off yet and I had already come once. I took off her jeans and noticed a big wet spot on her pink cotton panties. I took those off carefully as I decided I’m keeping everyone’s panties from this contest. Just like Trudy, Jane had a real hairy bush. Again, I didn’t want to eat it, just fuck it. The wet panties had me hard again so I wasted little time in sliding my dick inside her.

Jane had the biggest smile on her face while I was on top of her fucking her. She started talking real dirty to me and then all of a sudden started screaming. She began yelling that she was coming and not to stop what I was doing. This went forever it seemed like. She then stopped yelling and begged me to come inside her. That was all I needed, I soon let loose for the second time. I then went down on her and ate all of my semen out of her pussy. She was a little weirded out by this, but I told her it is one of my favorite things to do. I explained that I enjoyed the taste of my own come, and it was even better out of someone’s pussy.

We were both pretty drained and decided to fall asleep. Unlike last week with Trudy, there was absolutely no awkwardness. Instead of getting dressed and leaving right then, Jane and I decided to stay the night together.

I woke up to the best feeling in the world, a woman’s mouth on my dick. Jane noticed I was awake and she told me that she hadn’t sucked my dick yet and she had to in order to win the award for best cocksucker. It was probably the fastest blowjob I’ve ever had. Since I was hard all night it took me no time to shoot my wad down Jane’s throat. She swallowed it all and told me she had to get home to her husband. I thanked her for the night and she told me to enjoy the rest of the contest.

Jane’s grades for the night were:

Breasts B+ (Too big to receive an A)

Cocksucking C- (Probably my fault since I came so quick that she didn’t get a B)

Fucking B+ (I loved how she was so loud, I hope the neighbors did too)

Next week I have Donna to look forward to. She is divorced, in her early 40s, great ass, but very small tits. Something about her always gives me great orgasms when I jerk off to her. Probably not a contended for best breasts, but I hope she makes up for it in the other two categories.