How do you prepare for pegging?
First and foremost, lots of foreplay. They should be throbbing before you even think of moving to their ass. Lots and lots of lube. If you think you have enough lube, you don't, use more. Start with one finger and insert it slowly. Curl it JUST A BIT to get them used to that pressure. Ask them to squeeze as hard as they can, then curl it some more, gently. Tell them to relax, add another finger, clench again, but this time, separate your fingers like scissors. This is what will actually stretch them. Repeat until they've taken three or four fingers, then you can use a toy or your cock, depending on size. You don't want to go straight from fingers to your biggest. You need to work up to it, so start small. If you have an average-sized cock, you can use that, but go slow. Press the head against your ass and slowly start to apply pressure. Again, depending on size, it might slip right in, or they might need time to slowly stretch around it. Once the head is in, don't think you can go all out and start thrusting, you have to get the rest of it in first. Slowly apply pressure, tell them to clench and relax. Each time they relax, you should feel them pull you in a bit more, until you're as far as you can go depending on your and their anatomy. From here, let them adjust to the stretch, then rut into them gently, not pulling out, just moving inside. Once they're comfortable with that, pull out almost all the way - leaving the head inside - and then push back in all the way. Let them adjust to that, and then you can start going harder.
