So I'm just gonna get straight to the point: My boyfriend told me that he would like to be pegged. We talked about it a lot, and it's both something we have never done before. We haven't been together too long, so firstly, should we be experimenting with other stuff first? We have both never really had any play in the anal area, which scares me. I have no idea how to initiate this kind of play. Like obviously we have to go buy a strap-on and stuff, but how do we transition from pretty normalish sex to me ramming something into his butthole? (What size or type of strap-on?! Where do you even go and buy stuff like that?!) Like what's the middle ground here?! Is there even middle ground? Would that make it easier if we were both experimenting with each other's butts? Also. How does one get ready to have something in their butt? I just keep picturing being behind him, with him bent over and me freezing because I have no idea what to do!

Scared Of Butts

A multimedia response... after the jump.

There is no middle ground, SOB. So watch this and have a few laughs...

...then watch Tristan Taormino's "Expert Guide to Pegging." Then fuck the living shit out of your boyfriend's hairy, adorable little butthole. Plow it like a queen, dude.