ANAL SEX: FEARS OF ANAL ENTRY
 
 

Now you'll want to learn to loosen it enough to let in larger sizes. It may seem at first like you anus has a separate personality, doing things in its own way. But this is only because you've separated it in your mind. If you get to know it better, it'll eventually make friends with you, and the separation will disappear. After using your finger to meet it, get to know your anus more intimately. You can trace warm wet rings around its outside; after inserting a finger you can massage it, pressing outward in a circle, tensing and calming it, trying to curl your finger around its side, feeling its touch through the skin - while exploring, if you act like you're shitting, pushing out, this will help even more. Practice stretching and tensing/calming your anus around your finger; you want to do this until it can be widened easily and painlessly.

Next you can insert two (or more) fingers, seeing how far you can bend them apart. Later, you might want to try a dildo (a straight, smooth, round tipped object like those found in sex shops). It's a good idea to use something that won't break, such as plastic or rubber. Glass objects can sometimes shatter, and a candle could snap in the middle leaving half stuck inside, so be careful... you don't want to become the next weird newsworthy object of humiliation! Otherwise, feel free to indulge, since you can only hurt your rectum with sharp objects or violent jabbing motions.

 
 
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