So I've had anal sex with other women before but my wife was scared to try it. Having popped a couple of anal cherries, I told her other guys didn't know how to make it not painful. One night while having sex I decide to lick my finger and insert it into her ass. I did it slowly while she was riding me. She began to buck back and allow my finger in her ass. She enjoy it so much she had a hug orgasm. So the next weekend we went out and bought a butt plug (medium size) and some lube. So we used it that night and while she rode me again, I fucked her ass with the butt plug. So a few weeks later, she got drunk so I took advantage and told her I was going to fuck her ass. Well, liquid courage made it easy for her to say okay. So I played with her ass with my finger until she was ready and I slowly entered her ass. I told her that she had to relax and once she did, she began to back up against my dick. I dropped a huge load in her ass. I fuck her ass about once a month and she loves it 😁