Have posted on some of this but some other memories have come to mind.
Yes, I did this with three women I dated. One was when I was just out of college, and she liked being told she was bad for her overtly sexual thoughts, and being punished, having her bottom spanked and then "inspected" over the next few days. During these inspections of her pink skin I began making her bend over then spreading her cheeks to look at her anus, describing in detail everything I was doing to her. I think the narration turned her on as much as the physical sensations. The second woman always said "but I'm a good girl" to persuade me not to cane her round bottom, but of course it always got caned with a long thick plastic dowel. When the punishment was finished, I would straddle her legs and spread her cheeks very wide open, first just looking at her anus but saying nothing, which caused her anxiety. Then I would lick her hole very gently, which she loved, and then would follow a deep fingering and then an ass-fucking with me always coming in her ass. The most recent was a girlfriend who was very anal-oriented, who used to think of anything butt-related as 'perverted' and 'disgusting' when she was younger, but who had developed a very naughty fascination with it around age 28 when we met. Her spankings were often paused so I could spread her cheeks and hold them open, silently, which usually made her squirm and ask "what are you doing? why are you looking inside my ass? noooo". If she was being caned as punishment then sometimes I would insert the tip of the wooden dowel in her anus. The dowel I used on her was finely sanded and oiled btw.
Many of the other women I dated liked the attention I gave their bottoms but few were willing to discuss it, being much to shy and embarrassed to do so. So what my fingers and tongue did to their bottom holes was always gentle and erotic rather than focused on punishment.
One other woman stands out because although she loved being rimmed, like for as long as I could do it, it was never a situation about punishment or something negative. She was so comfortable with her body. Her attitude was completely different from any other woman I've been with. We were colleagues in our 20's and became friends with benefits. No I LOVE YOU's just alot of sex. On just our second date, we were making out and the clothes began to come off. At one point I rolled her over onto her stomach to have a look at her ass, covered in sheer panties. She was tall, blond, in very good shape. It was a stunning view and I was dying to see her bare butt. She seemed so happy and relaxed that I gently gripped the waistband and said 'may I?' and she said 'of course' and so I pulled her panties down and off her legs. I think my breath stopped as her gorgeous bare bottom was exposed to my eyes. I began caressing it and she just turned her head to the side, closed her eyes, and smiled. I think we were both in heaven. The more I touched her round little pale ass and leaned in to enjoy the view, the more I wanted a more intimate view. She seemed so comfortable that I felt bold enough to go further. I laid both hands on her cheeks and gently spread them open, fully exposing her anus, asking 'is this OK?'. She quietly said 'yes'. Looking right at her very light pink and slightly wrinkled bottom hole, I said 'you don't mind that I look at you here?' And she calmly said 'no, it's fine' with another smile. That began many months of anal play between us, mostly me rimming and sometimes fingering her bottom, both of which she described as 'soooo relaxing' and 'like a tickle'. She definitely went to another place mentally when I focused on her ass, though if I eventually started touching her pussy too, she would slowly build to orgasm. The one and only time I tried to "punish" her, just to see if she liked being spanked, I spanked her during sex, one swat to her bare cheek, and she turned immediately with an angry look and said 'DON'T EVER DO THAT AGAIN'. So I definitely never did. Her bottom and anus were 100% for pleasure, not punishment.