Real life is messy. Literally. If you are playing in that area, accept that bodies aren't sterile. Keep a towel nearby, laugh if something weird happens, and move on. Maturity is sexier than perfection.

During foreplay, use a lubed thumb or finger to massage the external sphincter. No penetration. Just pressure. Do this while giving oral or a handjob. The goal is to associate anal touch with orgasm.

Use a small toy (or pinky finger) with tons of silicone lube. Insert just 1cm. Hold. Breathe. The sensation is intense pressure. Have your partner push out gently (like having a bowel movement) as you insert—this actually relaxes the muscle.

Watch any of our anal-centric videos. Notice the pace. Notice the communication. The couples aren't grimacing; they are breathing, using their hands, and checking in. If it hurts, you stop. Pleasure is the goal, not penetration.

Today, we are taking the pressure off. This is your judgment-free guide to exploring anal together.