Best wager you've had

[cufan86]

Originally Posted by Yorkie11

Well I was asked to keep a couple of you updated. We did indeed go out again with the same basic wager. This time it had to be different pics. The extra bit was that if one of us won all 3 formats then the pic had to be more graphic. It was up to the loser to determine how far the went. We also decided that if some one wonby a considerable margin (we decided on 10pts,10strokes or 6 holes) then the loser had to send the winner a picture for him to enjoy at his leisure. Unfortunately for me I lost all three this week. In fact I had such a shocker that at one point I was in danger of losing by ten. Luckily he mucked up the last 2 holes. Playing again on Thursday......

Tremendous. How about describing the photos you showed.

Also, are you going to tell us about the other bet you mentioned previously?

[JonScores]

My wife and I attended a state college, where we graduated. We have friends at this stage of our life that went to "The University" for our state. Our colleges play each other every year for State's bragging rights. I have to admit that they have won more frequently over the years than our college. However, I had a feeling about this particular year and felt certain we would win. We invited the other school's couple over as was the norm. They started talking trash about how they would win for the 4th season in a row. I said, "Oh, yeah, let's put something on this year's game." My buddy agreed and said, "What do you have in mind to lose." I responded that I bet that every time my school scored that they would lose an articleof clothing and sit the remainder of the game without that article of clothing." They said,"Will you guys do the same?" I said that we would. Then my buddy asked, "What if you run out of clothes?" I responded that he could screw my wife." He looked over at my wife, who looked a little astonished at what I had proposed, but somewhat reluctantly agreed. He and his wife agreed the same. Then we set the ground rules. Each person could wear only a shirt, pants, underpants and socks. No other articles of clothes would be accepted. My buddy said,"Bring it on!"

The game started,and our side scored a touchdown first. They removed their socks. Then the other team scored, and we removed our socks. During the second quarter, both sides scored, and we all had to remove our pants. That left the girls in their shirts and thongs and the guys in their shirts and DVD's. In the third quarter both teams scored again, and we all had to take off our shirts. That left all of us topless with the girls in their thongs and nothing else, and the guys in their DVD's. Finally, in the 4th quarter, the other team scored, and my wife and I had to remove our underwear, and go nudey. Our friends laughed their ass' off at this scene. However, the next possession, our team scored, and they had to become nude. So, there we were all nude watching the final 5 minutes of a tied game. Our team had the ball, and we drove almost the entire length of the field, but our quarterback threw an interception at their 18 yard line with 2 minutes and 15 seconds left in the game. Sadly, their team drove the ball down to our 15 yard line with only 3 seconds left. Then they kicked a field goal with no time left for our team left to respond. My buddy said, "All right, I get to collect." My wife said, "Oh, my God."

My buddy told my wife to come over to him and lay back onthe floor. With his wife and I watching, he spread her legs out with her on her back on the floor and started kissing her tits and working down to her pussy. She laid back as he started eating her out. She began breathing heavily, and I think in a way that she was enjoying it. Then he worked his way back up her body and started kissing her as he traveled up. Then he took his member and entered her pussy. He exclaimed, "Man,you are really wet!" That, I think embarressed her, since she was not supposed to be enjoying it." He took her legs and tossed them over his shoulders and commenced to giving her a tremendous fucking. She couldn't help but to scream out in her ecstasy. Finally, both collapsed in a heap as they climaxed together almost simultaneously. He slowed pulled out of her as his cum came dripping out of her pussy onto the carpet. She just laid there in her nudity totally exhausted not moving a muscle. She was exhausted from his fucking. He got up and grabbed a beer out of the cooler and said, "Thanks for the bet!"

I think his wife was a little pissed off that he enjoyed himself so much. She looked at me and said, "Well, I feel sorry for losers. I think you need a little consolation prize. How would you like to fuck the shit out of me?" I looked at my buddy, and he said, "If she wants it, give it to her." We were all nude, so it was easy to go over to her and replicate my buddy's approach with his wife. Then we commenced to fucking. I nailed her from the rear first. By now, my wife was up and watching the action. I fliipped the lady over after dog fucking her and went to the missonary position. I pumped her good in that position. Then I pulled out and asked her to suck my dick, which she did for a good while. Then I tossed her back on her back and threw her legs over my shoulders and fucked her until we both came. I left her exhausted on the floor, and grabbed a beer and downed it. My buddy said,"That is the first time I won a brt and lost it just a little later." We both laughed as I looked down at his wife dripping cum all over our rug. Both ladies got up and went to the shower to clean up.

In the meantime, we all said that this should be an annual event. Not a one of us disagreed. We all had a great time! So, bets are on!

[eugene0]

I was about 23 and was at the local bar. It was a slow night and I was talking to the bartender. I could feel sexual attraction but she was married to an iron worker/ biker and he was a friend. We started playing darts when she tells me if she wins I must take off an article of clothing. If I win she’ll do the same. Starts out pretty tame and we kept mental score in case someone came in. Pretty soon it is really close and she locks the door and turns off the lights so we can “end” the game. We tally up and she is down to bra and panties, I’m done to shirt and underwear. She loses 2 straight and is now naked. Early 90’s so she has a dark landing strip and 5-7” with b cup. She flat out tells me that there will be no sex but she wants to see me masterbate. So I start taking the remainder of my clothes of and start stroking my cock. As she is watching me she starts doing herself and is really wet. She yells that she wants to taste me, so I cum on her lips. She is now married to one of my friends and we have never spoken of that night.

[1michael]

The neighbors wife came over our house and told my wife & I about what they did over the week-end!
It seems like they belong to a Bowling League Team along with 2 other neighbor couples!
During the game I guess they all were drinking and after the game all 3 married couples sat around at a table near the BAR and were still drinking more!
The couple that lives on the street behind our house is Dave and Lori, but while sitting around Lori kept on asking Dave for some Money cause she wanted to buy a new outfit for some place they were going in a matter of days!
Dave kept on saying she has enough outfits to wear and he wasn't going to give her more money for another!
We had neighbor Judy over the house and telling Us about this adventure, she said that Lori just kept on bringing Up the subject and it was upsetting to Dave! So after awhile in the BAR the Jukebox was playing and it gave Dave some naughty Idea! He told Lori if she got on top of the table and danced with her Top off for 1 Song he'll give her $50 bucks and put the money down on the table! Lori said No, then the other 2 hubby's pulled out $50 each and put them on the table! Judy said she told Lori that she could buy a nice outfit for $150 bucks, but Lori said she isn't going to expose her tits in front of all the people in the BAR / Bowling area for FREE even if the hubby's are paying to see them! Judy got her nerve up and said if Lori won't do it, she'll do it if they still let her have the Money and they did! So Judy said she went on top of the table and took her Top off while her hubby went to play a song on the Jukebox! While my wife and Judy were talking I went thru our collection of Records and pulled out the Stripper and put in on for them to hear! I walked up and asked Judy to show Us just how she Danced for a 3 minute record and dared her to do it again!
She did and my wife & I both were amazed an it didn't cost Me a Dime!
Judy later put her top back on, but not her BRA!
I never did ask nor find out what did her hubby say to her when she walked into their house carrying her BRA in her hand after leaving out house?
Maybe I'll take Up Bowling or just go to watch them now!

[kajuk]

In Louisiana, there are video poker machines in pretty much every restaurant and bar. When I lived in Louisiana, I had an ex who was very sexual and fun. She never once turned me down for sex or turned down an idea of something to do that was sexual. We frequently went to a local bat that was close to the house. One of the first times we went together, I said, Let's make a wager? I handed her $20 and said, Let’s each put $20 in the video poker machine. If you double your money or more, you win. If I double my money or more, I win. The winner gets to be the master for the night, and the loser has to be the slave for the night. If she wins, she gets to keep the money. If neither of us won, it was a wash, and there was no winner. (no master or slave). She was game and seemed to love the idea, and was excited to play

The first night we played, I won. It was a warm spring night. She was wearing a pair of black denim shorts and a very thin nylon blouse. As soon as I won, I said, OK, Slave, go to the restroom and remove your panties and bra. With a very large smile, she obediently went to the restroom and came out holding her panties and bra. It was obvious for everyone to see what she had in her hand, and she didn’t seem to mind. Her double D tits were visibly bouncing and swaying as she walked to me. She put them in my hand, I told her to go to the bar and order us some drinks as I walked outside and put them in my truck. When I walked back in she was sitting at the bar and the light was just right I could see the silhouette of her tits through her shirt. The material was so thin I could almost make out her areola and nipples through her shirt. As we sat at the bar, we talked about what she was going to have to do as a slave that night. While sitting there it turned me on seeing both men and women looking at her tits through the thin material of her shirt.

I told her I wanted to fuck her asshole when we got home but I wanted to do some daring things before we got home. She was very happy and enthusiastic to be my slave for the night and seemed almost giddy to be doing it. I put my hand on her leg and tried to reach up inside and touch her pussy but her shorts were too tight. I told her to spread her legs so I could get my fingers to her pussy. She did as she was told, and it looked almost vulgar as we were in public. We were sitting on bar stools, and it was so obvious what we were doing. I reached up and stroked her pussy with my pinky finger and I could feel she was getting wet. Because we were in public and before it caused a scene, I told her to put her legs back together. We stayed at the bar for a while and had a few drinks and we had a really great time. I could see she was feeling tipsy, so I said it was time for us to go home.

When we got outside to my truck, I told her to remove all of her clothes because I wanted my slave to ride home naked. She did as she was told and got completely naked right there in the parking lot with the lights shining on her and cars passing by. When we got into the truck, I told her I wanted her to masturbate all the way home. My goodness, it was hard to drive while she was masturbating. She put her feet up on the dash, and her legs were spread wide as I drove through the city. As I was driving, I noticed how the as we passed by the street lights how it would light up her beautiful body,tits and pussy. As we had to stop at a couple of red lights, she never stopped what she was doing even though there were cars all around.

When we got home, she didn’t put her clothes back on and walked up to the door obediently and waited patiently as I unlocked the door to let her in. I have no idea if any of the neighbors saw, but they knew me as the wild bachelor and would not be surprised. We went directly to my bedroom and she happily gave me her asshole to fuck. After she had several orgasms, I got to cum by pulling my dick out of her ass and shooting my cum on her big tits. She rubbed my cum into her tits and we fell asleep. After that night, it became a regular thing for us to make that wager. We called it the “usual”. Sometimes we played it a little differently. Sometimes she would win, and sometimes we would make the reward for the winner a little different but it was always something sexual. We dated for a little longer than two years, and over that time, we made that wager more times than I can count. We had to break up because she had some problems I could not deal with, and I could not help her with. I hated to see her go because she was such a sexual persona and never once turned me down for sex. Here are a few pictures of her so you can see what she looked like

[Melbourne_Couple]

My closest friend's sister knew that I had a bit of a habit of doing nude runs back in the late 90's / early 2000's. I did one on a night that she hadn't come out with us & she was a bit annoyed that she missed it. So, she made a bet with me that I would do a run just for her & it hinged on the result of how many votes a certain footballer received in the Brownlow Medal that year (an Aus Rules medal for the best footballer). I made a bet that I knew I would lose.

A couple of weeks after the count, she sent me a message saying that she was house sitting my friend's place, it was a warm night, so she wanted to cash in. I obliged, did the run out in the street & then ended up sitting around with her, naked, until she told me that I better leave as her boyfriend mightn't be happy with what might follow if I stayed.