For my wife it was always exit only. Then one day after I shaved her bare, front back, side to side, everywhere.....I licked her ass. She loved that. Then, as everyone has said, start slow. Tease it....massage it....and do it at the same time as her clit.
My go to move was two fingers inside on her G-spot, thumb or my tongue on her clit and then my ring finger massaging her ass...then eventually as I pump my fingers inside her the ring finger slides in....
Eventually she got used to toys, then my cock, then more and bigger toys in her ass. Eventually working our way up to a two man double penetration. Talk about a woman having an orgasm with that...holy shit.
Have patience, take your time, listen to her body responses and see how it goes. The wife that used to say exit only now loves taking it in the ass.
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