I have a pretty average length cock but it’s fairly girthy. I wouldn’t say absurdly girthy but thick enough that regular condoms feel like stretchy wrappers if I even try.
During a hookup with a tinder babe, she got a little wild after I ate her ass for a long time and asked me to stick my dick inside; I wanted to oblige because I’d fucked her sweet tight pussy raw till she couldn’t handle any tongue on it so I tried my best to ready her little rosebud apart for my cock. I did have lube as well but it doesn’t really stretch the butthole like training in advance does.
I wasn’t able to get my head inside and she kept muttering “I’ve had big dicks inside my ass before this is so strange”. I guess girth isn’t the same as length but we kept trying for a while and eventually I ended up bending her over doggy style and sliding my dick inside her pussy and keeping it there while inserting my finger inside her ass. She really enjoyed it and eventually thrusted back against me but very gently as opposed to the rough fucking just many minutes before.