Position for first anal

With wife:

She was on her side and I was behind her. I caressed her clit and pressed my glans very gently against her anus, without any strength or violence. Under my tender stroking, she slowly opened and let my glans penetrate. She then pushed against me a little more and suddenly I was all in. We enjoyed the feeling of this intimate union for a long time without moving, until we slowly began to fuck. I continued to spoil her clit until she reached orgasm. The intense contraction of her anus then also triggers my orgasm.

with a male friend:

He was lying on his back with his feet on my shoulders. So after a careful penetration into his anus I could masturbate his penis in the same rhythm with my movement. He reached his orgasm before me, and I could intensely feel and enjoy the rhythmic contraction of his anus around my shaft. Seconds later I also squirt deep inside him.