It's been a few days since day 2 but here it is.

On day 2 (yesterday) we had 4 challenges. The first was to shake the best milkshake in your (clean) ass. The next challenge was to see how many pool balls could fit in your ass. The third was a rimming challenge, we were trying to see who could last the longest while being given a rimjob. Finally the fourth was to go out into the local shopping mall and get as many guys to fuck your ass as possible. (I'm only posting the first two challenges in part 1 to avoid this post being too long.)

The first challenge depending on how you look at it was probably the kinkiest. I wanted to replicate one of the challenges from the original "anal olympics" post however it's been deleted. I did however find a comment talking about making ass milkshake. Prior to the competition I went out and bought a boat load of stuff needed to make milkshakes including (ice cream, milk, chocolate, cookies, toppings, cherries, cum, and frozen fruit). We all spun some wheels to see what ingredients we would be using and how long we had to shake it up. (I should note that I bought mint and rocky road ice cream too but somehow we all ended up with vanilla ice cream) Alyssa's ingredients were as follows: Vanilla Ice cream, frozen strawberries, crushed oreos, sprinkles, and we also decided to make cum the required ingredient.
My ingredients were as follows: Vanilla Ice cream, sprinkles, cum, milk, and dark chocolate.
Finally Sarah's ingredients are as follows: Vanilla Ice cream, cum sprinkles, chocolate chip cookies, milk, cherries, and frozen mango.

I volunteered to go first and I had only 30 seconds to shake my shake. I laid upside down against the couch with my ass facing the ceiling as Sarah Spreads my hole as wide as it will go. Alyssa on the other hand was scooping the ingredients in. Once everything was in and the plug sealed it up my timer started. I usually try to grind and twerk and stuff of that nature when I'm with other guys but this might have been the hardest I've ever shaken my ass. In the end it did get pretty shaken up. I got back into the starting position with my ass to the ceiling and this time Sarah and Alyssa were doing the same thing. To speed the process up we decided to do them both and have the judges fill them up with their ingredients. Sarah had a minute while poor Alyssa only had 15 seconds. Once their timers were done they laid against the couch with me and we removed our plugs waiting for the judges to taste our creamy asses. Surprisingly I got first and Alyssa got second while Sarah got third. Apparently they thought Sarah's thick ass would make it taste better.
To clean up Each judge took their sweet time fucking our creamy asses and cumming in them. We then licked their cocks clean and drank the milkshakes out of each other.

The second Challenge was to see how many pool balls we could fit in our asses. For this Sarah bought 2 sets of pool balls since we didn't expect to need more than 32. Since Sarah bought the sets it was only right for her to get first use right? Well she thought it was fine and got in the doggy style position. It was fine until the first 5 went in. After the 7th she tapped out. Alyssa was up next and although not being very experienced with large dildos she regularly puts pool balls in her ass. This gave her a slight advantage and ended up with a total of 16 balls (a full set). Finally there was me, I don't want to overbearing but 16 seemed a bit too easy to beat. After the first ten I was already starting to feel it. I however set out to beat 16 and I was gonna do it. I managed to get 23 before needing to push them back out. I couldn't see it but because of how fast the pool balls shot out of my ass the judges were laughing for 5 minutes straight.
I don't think I need to say this but The second challenge I got first, Sarah got last and Alyssa got second.

Part 2 will be up in an hour or so