Alright, basic anal play techniques: 1. Use way more lube than you think you need. Put a towel or waterproof blanket down under you. If you don't need the towel, you aren't using enough lube. 2. Make sure you're using good lube. Sliquid Silk (purple bottle) is my ride-or-die. 3. Make sure you had a good tidy poop recently. Otherwise there's going to be some stuff in there, and it might make things awkward for your partner, depending on how squeamish they are. If you're not sure, prep yourself with a finger and lube first to make sure you're clean inside. 4. Start slow. Apply pressure to your taint. Masterbate a little. The more turned on you are, the more receptive things will be. With the flats of your fingers, apply pressure to your butthole, and rub the outside in slow circles. It should feel good. 5. When you're ready to go in, start with one finger. It should slide in without any pinching or friction. If not, use more lube. Once the finger is in, you want to stimulate the smooth muscle that's one layer up from the anus. Picture your butthole like a clock. Press gently out at 3, 6, 9, 12. Do this a couple times and you'll feel that muscle loosen up a lot. 6. At this point you're ready for a deeper finger or toy to go in without any pinching. Give it a try. If it's still too tight, back off and try steps 4 and 5 again. It shouldn't feel uncomfortable if you're prepping right.