So i’ve found myself intrigued by the idea of inserting a banana into ones anus. I kept wondering how it would feel and how it would work. While chatting with a guy on a sex chat, he asked why I didn’t try it myself, and in effect dared me to do it…so I did…twice. After much discussion with the person, the dare was to insert an entire banana up my ass and leave it in with the aid of a butt plug for a period of 1 hour. So here’s a dare that might interest any of you who are into anal and some mild elements...

For the past two weeks I have had a bad cold which has turned into a bad cough and asthma. For this reason I haven't really felt like doing any anal with my new toys. I did, however, get to try them out one day when I was actually not feeling too bad.

I got a bright purple 6 inch dildo that is thicker than my current anal dildo, but thinner than my oral dildo. The one I use for oral is just a bit too big. I can get it in my ass but it takes a lot of easing it in. The new dildo is much...

I'm looking for a way to wreak havoc on my pussy and ass. I will be your slave. If I can't do the dare I'll take your punishment.

In the past I have done a little bit of anal. Nothing more than an enema and then poking around in there for a bit (fingers or marker). A little while ago I bought a buttplug (small metal one with the jewel thing in the end). I never got around to using it until yesterday because of a number of factors.

I cleaned my ass out and then got ready. It felt really good pushing it in. It sat nicely and I could do other things while it was in. I think I left it in for about 20 mins before taking...

All of this is fact. Some parts may have happened at different points to how I remember them now.

A friend (male) and I have had a set of dares going for a while now. It started years ago when we were playing Minecraft a lot. We decided that we would do a diamond finding challenge and the loser had to complete a dare. I managed to win (may have used an xray pack, but not sure now). I believe that dare was quite tame. If I remember rightly he had to lick my feet when we were next hanging...