Here's a dare for you, hope you enjoy and post a report.
Find something that you can both put in your asses, but it has to be as big as possible (double ended dildo, big candle, big can of air freshener
). Get naked, on all fours, ass to ass. Put that thing between you, so it rests against your assholes. Now start to push at each other, trying to get the thing into the other's ass as deep as possible.
The first one to give up or quit or whimper or pull back (you need to decide) loses. If you manage to get your asses to touch (with the thing within your butts), start bumping at each other as hard as you can for 1 minute. If you still can't make one of you quit, then it means the thing was too small and you both lose (or can make another round with some bigger toy).
Now, the prize for the winner & the punishment for the loser is as follows: get into the 69 position and the loser has to bring the winner to orgasm orally, while the winner is vandalizing the loser's ass with their weapon of choice (might be the same thing used above or anything else). The longer it takes the loser to please the winner, the longer the punishment.
Note: if you don't have any toys suitable for this dare, you can try the following variant. Get into the position as in this video:
http://www.pornhub.com/view_video.ph...key=1427734212 and start fingering each other's asses simultaneously, adding more fingers as you go. E.g. 1 finger for 1 minute, then 2 fingers, up to entire fist. All other rules just as above.