well, we were having sex and he suggested we change positions and asked if we could do anal so i said yes and we went right for it. preparation seems like the good route, though, and wish i'd done it beforehand. during it, i wasn't really sure what to do/what to expect, and the feeling was pretty strange and uncomfortable (it was also during the middle of the day and in front of my open windows that look onto harvard dorms, so paranoia about people seeing us probably didn't help either). i think you're right about it being a gradual process, though, so it should feel better in the future. what did you do to prepare?
Well I started with small things. Wasn't able to buy toys, but I had lots of sharpie markers, so I started with one there, slowly put it in at just let it sit there for a while, then work my way into moving it in and out. Became kind of like a routine every time I masturbated until I felt really comfortable with it and didn't have to put it in/move it slowly anymore. Then I moved on to two sharpies, then those jumbo sharpies and did the same process. To be honest it's probably better if you get the toys that are meant to go in that area like anal beads or butt plugs, but if you don't have access to those things, just use sharpies and other friendly shaped items. If you don't have lube, use your wetness or spit, but obviously don't double dip, haha.