At first let me say that I checked the spoilers before I started the dare.
Like everyone I can only enjoy things within or slightly over my limits.
You cant exspect people to accept in everything.
Your dice at
http://www.bgfl.org/bgfl/custom/reso...s/dice/six.htm was very strange I got 6,1,1,1,1 and than 6,6,6,6,4
Instead I used
www.random.org and got 2,1,2,5,4
As you said: "let's go"
[Round #1]:
2. Spank your ass 20 Times MEDIUM Hard with your hand
this wasn't too bad 
[Round #2]:
4. Smack your genitals 3 Times Really hard with a belt or a hairbrush
ouch! pain, or mild pain in sth. I only do as punishment and this was a good one. I never smacked my clit with a hairbrush before and I dont look forward to du this anymore.
[Round #3]:
2. insert an object/dildo in your ass, you can use your spit as lube.
I used a textmarker. I sucked at it and than it took me some time to bring it in with out much pain. (anal is also sth. I normally only do as punishment)
[Round #4]:
5. Insert your finger in your ass, fuck yourself for a minute, than lick your finger
gross! okay to to get my finger in was pretty easy. The textmarker strtched my hole before. To lick at it afterwards was my first ass-to-mouth-experience ever! I was nearly puked and immediately brushed my teeth.
[Round #5]:
1. Play again
Even though this dare was not was I exspected and more like a medium punishment to me I will follow the order
Will report again when done.
Btw. I just did your dare because I like your mix of random sampling and pretended tactical playing. I hope you wont charge me If I copy this in some kind?
great ideas! great dare!