Have you ever tried or successfully fucked yourself in the ass? I've tried many times & just can't quite seem to do it. I can get the tip of my penis there, but it just never quite pops in. I've seen videos of it & they make it look like it's not really all that difficult. I'd absolutely love to be able to fuck myself, since my wife doesn't have much interest in sex.
Ohhh. Not quite where I thought you were going.. But in the neighborhood. I have tried it, especially in the last couple weeks since I seem to be Lubed and clean.. Why not? I can only get the head part way if I'm not all the way hard at the time... If I continue, it lead to a painful orgasm for me.. My wife also has very little interest in sex and I have no interest in cheating.. Beyond fantasy anyway. So, during solo time it never hurts to get creative.
I haven't been able to but I've managed to insert our boyfriends cock into his ass. His 9 1/2" was quite easy to get in but we tried and tried to get my 8" in mine without success.