The Work Contest Ch 03

I was now a third of the way through the contest with my coworkers. The six older women I worked with seemed to be enjoying the contest as well as I was. I would notice them whispering or talking behind closed doors quite often. This week’s “date” was one I was really looking forward to. Not that Trudy or Jane were a disappointment or that I never really wanted to fuck them, that wasn’t it at all. It was that this week was Donna’s turn. She is divorced, in her early 40s, great ass, but very small tits. But there is something about her that has given me so many great jerk off sessions.

Monday morning I was minding my business in my cubicle when there was a knock on the wall, I looked up and it was Donna. She came over and gave me a kiss on the cheek and asked if I was ready for Friday, I said I couldn’t wait. What she did next was shocking. She sat on my lap and grinded her ass on my cock, it lasted for only 30 seconds but it was amazing. She got up and left without saying anything. I left right after her and made my way to the bathroom where I stroked my six-inch dick for a couple of minutes before coming.

I didn’t see Donna again until Wednesday morning when she dropped off a brown bag on my desk and told me it was a present to get ready for Friday. After she walked away I looked in the bag that she gave me. It was a pair of black thong panties. When I pulled them out to look at them I noticed they were still a little warm and that there was a little wet spot in the crotch. Did she just take them off and give them to me? It was possible. I wasn’t totally sure what I wanted to do with them. I thought about it for a few minutes and then snuck off to the bathroom. I wrapped them around my cock and stroked myself for a while. I was getting ready to shoot my load so I carefully laid the panties down on the counter and aimed for the crotch. Since panties are one of my top turn-ons I had a huge load. I then folded them up so none of the come could escape and put them back in the bag.

I was just going to drop off the bag on Donna’s desk and leave but she was there. She asked if I didn’t like the present and I told her I loved it and it was now her present. Donna took a look in the bag and didn’t notice anything until she started to pull them out. When she saw all the cum in them she flashed me a huge smile and proceeded to put them back on under her skirt. She thanked me and said that she couldn’t wait for Friday. I was truly shocked at was she just did and it gave me another hardon knowing that she was walking around with a load of my semen in her panties.

I didn’t think Friday was ever going to come. After jerking off into Donna’s panties on Wednesday, I had stopped masturbating for the week. I wanted to give it all to her on our “date.” We had both arrived at the restaurant at the same time. I watched Donna get out of her car, waiting to see what she had on. She had on the shortest skirt I’ve ever seen her wear, and also a very sexy top. We gave each other a hug and she started to rub my cock through my pants. I suggested we skip dinner and head straight to the hotel. She kept rubbing my six-inch dick and said that sounded fabulous to her.

Once at the hotel I couldn’t take my eyes off of Donna’s short skirt. Her legs looked unbelievable. And I was also wondering what kind of panties she had on underneath it. We started to kiss and Donna whispered in my ear that she needed my dick in her mouth now. She got down on her knees and undid my belt and pulled my pants down to my ankles. I had a wet spot in my underwear from my precum. Donna grabbed them and pulled them down as well. My dick stood straight out and was begging to be sucked. She took it all in her mouth and started bobbing up and down on it. I always thought she would be good at this. She would alternate between sucking and licking it like a lollipop. It wasn’t going to take me long to come. I hoped she wanted in her mouth, because I sure did. A few minutes later I alerted Donna that I was ready to pop, all she did was keep sucking and gave me a smile, I knew that was the go ahead I needed. I moaned louder and let my semen fly down her throat. The feeling was unbelievable. Donna swallowed my come like a champ and all I could think about was the award for best cocksucker had just been won.

Donna stood up, kissed me on the cheek, and thanked me for letting her suck my dick. It was definitely one of the greatest blow jobs I had ever received. So good in fact, that my cock was still rock hard. She grabbed it and told me why she liked fucking younger men so much. I told Donna it was getting ready for her pussy.

She climbed up on the bed and got on all fours and asked if I minded fucking her from behind. Of course not I told her. I got behind her and hiked her skirt up around her hips. This revealed a gorgeous white thong that looked so good on her ass I didn’t want to take it off. Instead I moved it to the side so I could slide inside her. My six incher had no problem getting inside Donna, as her pussy was sopping wet. I started fucking her pussy very slowly, even though I just came in her mouth, I knew I wouldn’t last much longer inside her pussy. I started to increase the speed and as I did that her moans became louder. Donna started screaming for me to pound her as hard as I could. Of course I couldn’t say no. She said between her screaming and moaning that she loved feeling my balls slap against her. I was nearing the point of no return when Donna screamed out that she was coming, I just kept going. All of a sudden her moaning stopped and that is right when I unloaded inside her pussy. It felt so fucking good. We both collapsed onto the bed and held each other’s sweaty bodies. A few minutes later we fell asleep.

Donna and I fucked five more times that night in between more sleeping and talking. By morning I was drained, I had come seven times last night and with all the hard fucking my dick was pretty worn out. It was truly an incredible night together.

Donna’s grades for the night were:

Breasts D+ (Very small, but still decent to suck on)

Cocksucking A (Unbelievably good, she definitely has had a lot of practice)

Fucking A (An older woman who just loves to fuck, my dream woman)

Next week I have Teresa to look forward to. She is married, in her late 40s, nice ass, but very small tits (about the same as Donna). Teresa and I are close friends so I think it is going to be somewhat awkward. She has told me that she has only been with her husband. I can’t wait for her tight pussy.