Have done lots of anal play with my wife, fingers, toys, my cock. She’s usually ready for it when her pussy is wet and excited and she’s had a clitoral orgasm and a few from her pussy. Her tight little asshole opens up a bit and lets me use it. She just this past week took the widest plug she’s ever had in her ass and it felt amazing to fuck her with that in her asshole. She usually orgasms at least once from anal play, she’s loud and noisy, grunts, pushes her ass back. Not too much awkward stuff unless you count it becoming messy which will happen sometimes but she never has any problem with that. Anal play is a big part of our sex life for sure.