Water-based and silicone-based lubes work well with both latex and polyurethane condoms. Apply lube to one finger and gently insert it without moving it around in order to condition her to the sensation of something being in her anus.
Many couples prefer a thicker lube (a “gel” rather than a “liquid”) for anal sex. Once she is comfortable with being dilated, slowly start to move your finger in and out and around.
If you’re self-conscious about your lover seeing your anus in full for the first time, why not gently shave or wax the skin between your butt cheeks?
It may take some time to get it just right, but if you follow these 10 steps, you will both have lots of fun trying.
The most important aspect of anal sex is communication, so be sure to talk to your partner about your anal desires before, during, and after your first session of anal sex.
Flick the tip of your tongue rapidly over the opening, or try inserting your tongue as far as it will go pushing and stroking it back and forth.
Try brushing your lips over the spot or sucking hard on the anus. Since the anal region is not self-lubricating, anal lubricants are extremely helpful for making penetration more comfortable and pleasurable. The sphincter muscles around the anus will not allow things to pass through easily unless you start small and take it slowly.
Clenching your anus can enhance the sensation for your partner. Stimulating other parts of her body during anal sex can help make her feel more relaxed and provide a greater thrill for both of you.
While thrusting in and out, reach around and finger her clitoris.
My article Which Anal Sex Positions Are Best for Beginners?
describes several anal sex positions, and tells you which ones are best for beginners and why. When you’re ready for penetration, take one or both of your hands and use your fingers to pull your butt cheeks gently apart.
Breathing deeply and talking him through what you’re feeling will help keep you both stay relaxed.