The Work Contest Ch. 04

With the start of week 4, I was now officially half way through the contest. Six of my coworkers all wanted a piece of me before I got married later this year and they were definitely getting some great sex with a horny younger man. So far I was lucky enough to fuck Trudy, Jane, and Donna. The three left were Teresa, Heather and Kim.

I arrived at work Monday morning ready for the new week leading up to my "date" with Teresa Friday night, however something came up so the schedule had to be rearranged. I received an email from Heather saying that she couldn't wait anymore and that she had to have me this week.

Heather is the youngest of the women in the contest, probably in her early 30s. My favorite part about her is her great rack. Those tits always looked perfect in her tight little tops. If I had to guess I would say 34C. The one thing I couldn't ever figure out is why her ass was so big, she seemed very fit. I had jerked off to Heather on occasion (Kim and Donna were my favorites) but that all changed one day when I left a meeting with her. I got up first and as she leaned over the table to get something I saw the smallest white thong rise above her pants. Panties are one of my top turn-ons (especially thongs) and this was an unbelievable sight. I went straight into the bathroom and jerked off. It didn't take long until I was shooting the cum from my six inch dick into the urinal.

Monday afternoon Heather stopped by my cubicle and said that we needed to have a quick meeting in the conference room. I followed her in and closed the door between us. She told me that she has been so horny for me after hearing about the "dates" from the other women that she has been fingering herself nonstop. But what was most important to Heather was winning the awards for best fuck or best cocksucker; she knew she was in good shape for the best breasts award. She asked if there was anything she could do to earn some extra credit.

One of the unofficial rules of the contest was no sex except for the Friday "date." So I tried to think of something else. My proposition to Heather was that every afternoon she would take off her panties and bring them to me and that I would be able to keep them. Heather agreed and since she was wearing a skirt, she reached underneath and peeled off a pair of black thongs while also giving me a glimpse of her neatly trimmed pussy. I grabbed the panties and noticed that they were very moist.

I laid them neatly on the table and spread them out so the wet part of the crotch was on top. I stood up and pulled my cock out. Heather was very surprised at this but also very excited. I leaned over the panties and started to beat off. While I was stroking my dick I saw Heather slip a hand under her skirt. Once I saw this I knew I was done. Three long ropes of cum shot out with most of it landing on her black panties. I put my cock away and thanked her for the panties and said that I done with them.

Heather grabbed her panties and to my surprise put them back on. Just like Donna last week, she was going to walk around the rest of the day wearing her cum filled panties. I let Heather know that I wanted to do the same thing the rest of the week except for Friday. I wanted to build up my supply of jizz for the "date," so Thursday would be the last day I would jerk off into her panties.

My afternoon meetings with Heather continued for the rest of the week. Each time the same exact thing happened. She would give me her panties that she was wearing that day and I would lay them on the table and beat off while making sure most of my cum landed in the crotch of her panties. Then Heather would wear them the rest of the day. Everyday Heather was wearing a thong, Tuesday was pink, Wednesday was brown, and Thursday was sheer white.

By the time Friday arrived I was ready to move beyond jerking off into her panties, I was ready for her tits and pussy to be the target of my cum. The two of us decided to get dinner on our date right after work so we could maximize our time fucking that night. During the work day Heather was wearing a tight blue blouse and black pants. I was dying all day trying to picture what thong she was wearing. But when we showed up at the restaurant Heather looked a little different. I noticed she undid a few buttons on her top and took her bra off. She looked so hot showing off some nice cleavage and her nipples seemed very excited to see me.

The conversation at dinner was about sex and the contest, nothing else. Heather wanted to know about the other dates and where the girls stacked up against each other in terms of the awards for best breast, best fuck, and best cocksucker. I was hard the entire time and even had a small wet spot on the front of my pants from my precum.

We didn't fool around at all until we were in the hotel room. But once we got there, there was no stopping the two of us. I instantly grabbed Heather and kissed her, she returned the kiss and we made out like we were both in high school. Her nipples were still visible through her shirt and I couldn't wait any longer to get them in my mouth.

I undid the few buttons remaining on Heather's shirt and saw two of the most amazing breasts I've ever seen. These were perfect, no sag, at least 34C, and fantastic nipples that stood straight out. We kept kissing and I massaged her tits with both of my hands. Heather broke the kiss and took off her shirt. Then she got down on her knees and undid my belt. When she pulled my pants and boxers down at the same time my cock pointed straight out towards her. First she just looked at it and admired it. Then Heather wrapped one hand around my dick, leaned forward, and took the head in her mouth.

It was obvious to me that Heather has sucked a few cocks in her life. She slowly devoured my six inch cock until she had the whole thing in her mouth. Her other hand was massaging my balls and I knew it wasn't going to be long until I shot my load down her throat. Heather's head bobbed up and down a few times and then I announced that I was ready to cum. She didn't stop her sucking and I let it shoot. It felt amazing to shoot my wad into her mouth.

I didn't know if she was going to swallow, but I wasn't going to let her. I pulled her up and went in for the kiss. I can't get enough of kissing girls after they sucked my dick and still have my semen in their mouth. Heather was surprised by my move but I think she enjoyed it. After we each swallowed all of my cum she led me over to the bed.

We removed the rest of our clothes except for Heather. She only had on the black thong that I jerked off into on Monday. Heather laid on the bed and spread her legs and had me take a close look at her panties. Not only were they soaking wet, there was a very evident cum stain. She said she hadn't washed them since Monday and wanted to surprise me with them again today.

I crawled next to Heather and started sucking on her nipples. Then I moved my fingers down to her pussy. I kept the panties on and forced my hand inside them. This may have been the wettest pussy I've ever felt. Two of my fingers easily went inside and it didn't take long until I was fucking Heather with three fingers.

Heather moaned that she was ready to my dick inside her. I carefully took her panties off and saw a pussy that was begging to be fucked. I got on top and slid inside her. I took my time and fucked Heather very slowly. With each thrust I slowly picked up the speed until I was pounding her pussy as hard as I could. She was screaming my name and then yelled that she was coming. That was all I needed. I kept fucking and was soon ready to pop. As I got closer I pulled out and aimed my dick towards Heather's tits. Since I already came once I didn't shoot it that far. My cum ended up in a small puddle near her belly button.

I was exhausted by this time but my dick wouldn't soften. It was probably because I was laying next to a hot woman that I just fucked and I couldn't take my eyes of the pool of cum I deposited onto her. Heather and I talked about the contest for awhile. She wanted to know every detail from my other "dates" again and she shared with me what the other women told her. It sounded like no one wanted this to end but there were only two weeks left.

Heather and I fucked a couple of more times that night before we went our separate ways. She talked me into fucking her doggy style, which was ok for except for big ass. I did cum inside her that time. Then the last time was another missionary fuck. My dick was done by that point which was too bad because I really wanted a titty fuck so I could bust my nut all over those magnificent breasts.

Heather's grades for the night were:

Breasts A (The perfect set of tits)

Cocksucking B+ (I wish I could have lasted longer to enjoy it more)

Fucking B (Nothing special, but a very solid fuck)