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-   -   Making bets and/or making deals (https://forum.oneclickchicks.com/showthread.php?t=273451)

kajuk 03-05-2026 09:40 AM

Making bets and/or making deals
 
Making deals and/or bets (wagers)
I was single for most of my adult life (about 45 years), and I learned a long time ago that I could get women to do fun things by making deals with them. I have many, many stories. I will keep it to just a couple for this story, just to keep it short.

I'll never forget this one particular girl I was dating in the year 1990. She was extremely gorgeous. She looked almost exactly like Merilyn Monroe, except my girl had much bigger tits. I'm not good at guessing tit size, but I'm guessing 40F or FF. She was a real party animal and loved going out a lot to the parties and clubs. My girl had played extras in a few movies. Not a big star, but now you can get a good idea of how beautiful this girl was. She has since passed away. God bless her soul. She was not a modest girl, but on the other hand, she seemed to dress down to try to cover her tits when we went out. No cleavage, even though she had one of the most beautiful cleavages I had ever seen.

One night, we were getting ready to go out. I don’t remember what we were having a friendly argument about, but I said Let’s make a bet. She agreed very quickly. I said if I when you have to wear a mini skirt with no panties. She said fine and if I win, she said something like I had to wash her car. The bet was on, and I won. She acted as if she was hesitant, but I could tell she was excited. Several times that night, while at the club, she parted her legs and flashed her pussy at me in that crowded place. On the way home, she said, that was fun. From that day (night) foreward we started making bets a lot.

Then I learned that if she wanted me to do something for her, I would say I’ll make a deal with you. At first, I would say show me your tits and I'll do it. She would smile and lift her shirt, and I would act as if I was seeing them for the first time, and she enjoyed it. It led us to more fun things and more sexy and sometimes X-rated things. She actually started bringing it up herself, saying if you do “blank” for me, I’ll give you a blowjob. With her, it was a very fun game between us, and it led to a lot of fun.

One day, we were at the grocery store. There were some jumbo shrimp on sale. She said oh I want these so bad, but I'm short on cash. The light went on above my head. I said, I’ll make a deal with you. She smiled and knew immediately what this was going to be. I said you pull your tits out and pull your pants down and masturbate on the way home, and I'll get them for you. She didn’t even hesitate and said OK.

On the way home, before we even got out of the parking lot, she pulled out those massive tits. I got so excited. Knowing that some people could possibly see. Then, when she pulled her blue jeans down over those curvy hips, I almost came in my pants right then and there. Damn, that was so fucking sexy! When we got home, we were both so horny that we had to have sex before we put the groceries away.

Though I do have pictures of her, I do not have any sexy pictures of her. I will not post any pictures of her on this forum out of respect for her and her family, and kids.

From that experience with her, I learned to start making bets and deals with every woman I dated over all those years, and every one of them did it and enjoyed it. I will write another story with pictures laterwith other women. I just ran out of time for now.

city slicker 03-24-2026 12:09 AM

I'll have to try that with my wife.

kajuk 03-24-2026 01:01 PM

This is another deal I made with my current woman. I wrote this a while back. One of my weaknesses is not being able to write humor. As you read this story, think of it as a humorous situation. One humorous part was the young man stumbling over himself to help so he could get more time to look at my woman, and the second part was the woman at first being angry and then later becoming flirty with my wife.

https://forum.oneclickchicks.com/sho...&postcount=494

GRITS 03-29-2026 04:22 PM

Baseball & football season
 
1 Attachment(s)
We often have "select friends' over for football & base ball games.....the bets are on quarterly or innings scores...the winners get to have private time w me in the quest room for 15 min.......

OzHarley 07-11-2026 07:14 AM

Bets or Deals
 
Very common with us, we are always making bets and coming up with different payments.
We are very used to our likes/dislikes/limits, so its always about pushing the edge of those.
Sometimes non sexual, lunch, dinner, etc. Often nudity/sex involved.
The old dare added as a penalty for losing a bet.

Its fun. Adds some excitement. Bit of a thrill.

kajuk 07-23-2026 10:41 AM

Last week, my wife was out of town on a business trip. The bank locked her debit/credit cards, so she was without money and not able to eat. She called and asked if I would Cash App her some money. Of course I said it'll cost ya in a joking way, and she said Of course, it always does. What do you want? I said How about a good 69 till we both cum? She said OK you got it!

supersmoothy 07-23-2026 02:32 PM

Several days ago, we made a bet on a future event about whose outcome we both feel very sure, even though we predict it will go in different ways. We'll know who wins in about a year's time. I asked her what she offered if I won. She replied "whatever you want". Now I have almost a year to decide what payment to demand. :D Any suggestions are welcome.

kajuk 07-23-2026 04:10 PM

Quote:

Originally Posted by supersmoothy (Post 3663667)
Several days ago, we made a bet on a future event about whose outcome we both feel very sure, even though we predict it will go in different ways. We'll know who wins in about a year's time. I asked her what she offered if I won. She replied "whatever you want". Now I have almost a year to decide what payment to demand. :D Any suggestions are welcome.

It's hard to make a suggestion without knowing y'all's dynamic. If you win, she has to pose nude, and you post pics of her here. That's my vote. But other suggestions have her ride nude as you drive down the highway or have her flash your best friend. I can think of about 100 more, but again I would need to know y'all's dynamic.

nigbo 07-23-2026 05:23 PM

Lost bets
 
My wife can be very stubborn & will not back down.
Arguing one day about something trivial - she was wrong - as ever!
I said I’ll bet you a month of blowjobs you are wrong.
She took the bait.
I had a very enjoyable month.
Now she’s a bit wary of betting

OzHarley 07-25-2026 10:09 PM

Sports Day Bets
 
Quote:

Originally Posted by GRITS (Post 3623890)
We often have "select friends' over for football & base ball games.....the bets are on quarterly or innings scores...the winners get to have private time w me in the quest room for 15 min.......

We do the same. BBQ with our wicked friends. Game on. Bets as we go on scores or things happening.

We have one great couple who support the arch enemies of the team we support, so when ever they play is a 'slave for a day bet'. Losing team has to provide two slaves, one of each, (doesn't have to be the same time) to the other team at a date chosen by the winning team. Slave duties limited to 'helping' out around the house!


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