text: It should not hurt at all if you do it properly. Lots of lube it to first rule, and communication is the second. Water-based lube works the best as long as there is no spermacide in it because that can irritate the tissue.\n\nYou can use fingers or sex toys to progressivly work up to what ever size you need, just to stretch out a little. \n\nIf there is any discomfort or pain is where communication comes in. If there is friction tell your lover to stop and add more lube, and if there is pain, try stretching out some more. \n\nOf course, there is a small percentage of people, who can't do it with out pain, so if it doesn't stop hurting, maybe it just isn't for you.\n\np.s. There are many products out there that go by some variation of the name "anal-eaze". This will numb most of the nerves, and make things easier, though it also makes it harder to receive the pleasure from the act.