My wife and I celebrate our wedding analversary every year since taking her anal cherry on our wedding night. It's always been a part of our sex lives: toys, fingers, fists and cocks. SexysubWifee can orgasm from anal and I love a good prostate massage, milking me dry.
IMO in my experience stretching is never necessary. With proper attention that sphincter will relax and expand to allow Homer a little play ground for a while. And as the back and forth motion continues it relaxes with the bliss of pleasure. Just my experience. It is addictive when done correctly.