An Instructional Tease: Anal for Beginners
Now, I want you to take another shower. Make sure you're turned on first, of course. Watch an anal porn video, stroke yourself, then hop in the shower when it's done. In the shower, touch yourself in the shower, feel yourself, and get your ass used to the sensation. As soon as you're done showering, while you're still in the bathroom, I want you to lube up your finger completely - you can never have too much lube - and slowly slide it into your ass. Get it as far in as you can. If it feels too weird, don't worry, just hold still for a minute, then try to get it all the way in. If it hurts, or feels like it's not going to go any further, then stop pushing immediately, and pull out, but if you use enough lube it shouldn't hurt.
When you finish, wash your hands, return to the tease, and continue.