I've been after my wifes cute asshole for decades. I got as far as tonge,fingers and small buttplug, but she was reluctant to let me put my cock in there. I even tried working her from the small buttplug , to a dildo about the same size as my cock. She was too aprehensive for anything bigger than a finger and told me that if is so easy to relax and take a big hard cock in your asshole, then Show me how easy it is by taking a dildo in my ass. This was a major impass. Early in our marraige she pulled this and had me eating my own cum. If I took a dildo in my ass and didn't scream in angony, then she might try it. Hmmmmmm. I felt it was good if it went either way, so I agreed. I made sure I was prepared and lubed up inside and out. I begged her to be gentle with me She pulled out a modest dildo, smaller than my own dick, lubed it up and eased it into my asshole, with a twist. She had a very intent look in her eyes and she began fucking me with long strokes, poking the head in and out, then back deep again. She asked me if I was enjoying it, because I wasn't hard. I had to explain that I was a little nervous, exposing myself to her will as she fucked my ass. We got into a nice rythum and I told her that I was going to cum. She lit up and started to fuck me harder. I was stroking and started to shoot cum everywhere, over me. She Loved it. Especially seeing my ass fucked and catching the huge load all over me and my face. True to her word, she did try it, but didn't like it. However she did like doing it to me and said she would do it anytime. Was it worth it? You bet it was.
Tell her you want her to do it to you again and you'd love to get inside her again. Many women who try a few times get to really love anal. Then they wonder why they waited to try it. I've read articles where women said they come harder while doing anal.
My 1st wife was reluctant but did try it. Our first couple times were inexperienced failures that she didn't enjoy, she wasn't relaxed enough. She didn't give up on the idea as about a month later we tried again in the "spooning" position and I made penetration slowly. She let out a sigh as my head entered. I paused to hear her say go in deeper. I did, and then she began pushing her ass against my cock as we got into a slow, pleasurable pace and I was fully inside her and released my load. After that evening she evolved into an anal queen, wanting me to fuck her ass a lot. After 28 years together and at least 1,000 times in her ass she was always tight and could take it in just about any position. I remember doing her ass at a concert one night as we were standing in the crowd...so hot!
The most she would let me do is eat her ass and use a small butt plug on her. Respecting her wishes, she didn't want any more than that, but she didn't have an issue with putting a big dildo up my ass. If that's as far as she wanted to go, it was cool with me. I never expected her to turn the tables on me and get into fucking my ass.