Anal with our mfm friend ....
We've done it many many times with him over about 4 years.
Several months into him joining us, I'd say 10th - 12th time in about a year. It got more comfy and relaxing with each visit.
Her and I had tried anal 4 times ever in 20+ years, always when she was ......, never went well.
One night he's with us, she's super turned on like normal, he's doing her from behind pulling her hair..like he had times befor, she likes it. He reaches for the lube, normal, puts some on his dick, normal, he says "they" are gonna try anal. I knew she'd say no way. I'm 6+, he's 8+. He slid a finger into her butt hole, she just stayed put. He lined up, SLOWLY started to push in, she let's out a loud deep grunt. Took him I'd say longer than I full minute to get it in, he went SLOW. Looked like her eyes were gonna pop out but she didn't make a sound. He starts to pump SLOW. I've never her herd her grunt that way, he pulled back, ...grunt, he pushes in...grunt.... in and out about 20 full length, slow pumps. I'm thinking WTF???? He pulls out, she loudly says woha... he pops it back in and she's into it. She tells him don't pull all the way out. Again I'm like WTF does that mean???? He gives her another 20 25 slow full length pumps, says he can cum, she says yea. He unloads in her butt, stays there for another minute, finally pulls out, she flips onto her back and says WOW.
Talk about catching me off guard......
Since then he's done her butt many times, I have too. When he's with us anal can be part of the fun. Just her and I not so much.
All good but ..... WTF ?