Befor I was married I fucked every woman I could. Some liked anal, some were just ok with it, some said no way.
We've been married 20+ years, tried anal three times, never went well. All good.
Present time...wife and I enjoy mfm fun with a guy we know. We'd done it quite a few times over about a year and a half, we were all comfy together, good fun.
One night he's doing her from behind, reached for the lube. Said "they" were gonna try some back door... I knew she'd say no way but she didn't say anything. She stayed on all fours while he put lube on his dick and her butt hole. I'm thinking he'll try to slide it in and she'll pull away. She stays right there, he starts to push it in, she grunts like crazy. He went SLOW soon was all the way in. He took a SLOW pump, she grunted like crazy. He took about 10 super slow pumps all the way in and out. Looked like her eyes were ready to pop out. He pulled out, she flopped onto her belly and said WOW. I was like WTF just happened?
Next visit just about same thing. It was like is she OK with it? Just tolerating it? He pulled out she said FUCK.
Next visit, same deal, he's pumping SLOW, she's kinda into it. He speeds up a little, she's grunting, he says he's gonna cum, more grunting. He lets it go, pulls out, she says FUCK.
Anal has become a regular part of our sex with and without him. There's been nights him and I both have fucked her butt.