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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.
Love,
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…
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.
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.
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