Most problems the first time are about stress, too little glide lubricant, or a toy that’s too large—not about the technique itself. The preparations are therefore simple, but worth taking seriously.
Go to the toilet in good time and shower. No special emptying is needed for a short session with a finger or a small toy. Cut and file your nails if you’re going to use your fingers, or use a disposable glove; the mucous membrane in the rectum is thin, and a sharp nail can cause small injuries.
Put everything you need out before you start: lubricant, a towel, possibly a condom for the toy, and something to wipe yourself with. Choose a time when you won’t be disturbed. Lie on your side with your knees drawn up or on your back with a pillow under your hip—both positions make it easier to relax your pelvic floor.
Start on the outside. Massage the perineum with your fingers and a little lubricant, and then let a finger rest against the anal opening without pushing it in. Breathe out calmly; when the muscles let go on their own, it’s easier to insert the finger or the toy. The external sphincter muscle that sits furthest out can be relaxed on purpose, but the internal one only does so when you’re relaxed.