Never, because it scares me and it sounds like it would just feel uncomfortable

Just after you've told them they're fat and repulsive. Works a treat.

I was drunk so I just kind of blurted it out. Luckily the chick was a skeeze, so while she didn't agree, she at least didn't let that stop her from getting railed in the traditional way.

Pretend to be really frustrated/annoyed about her being on her period. As if it's a selfish act, in an attempt to empathize with you she might just give in.
I've never really seen the appeal. I slept over at a girls a few weeks back who didn't want to have sex with me (imagine that) and I tried to convince her anal was a natural compromise.
Didn't work. Ended up giving me a blowjob. But blowjob's are so boring and don't really do anything for me so she ended up having to lick my ******* as I jacked off.

I tell you guys, getting your ******* licked is the future. A must try. It sort of tickles but at the same time feels good, but you know it's taboo so you feel naughty about that, then you childishly remember someone's licking your bumhole so you giggle because it's a ridiculous concept, all the while trying not to fart whilst imagining it probably tastes absolutely rancid.
It feels like little bubbles are entering your *******, like letting a goldfish blow into a little hole. It's therapeutic.

Sorry for my outpouring I have went really off topic. In conclusion Rez, forget giving her anal and get her to stick her tongue up your anus. You'll thank me later.

Just talk to her normally about it because if you want to do it right and not hurt her in the process. You have to do all the prep work.

By not bringing it up at all.

If he doesn't bring it up. How will he ever know if she is willing to try. Not everyone is against it.

I didn't say everyone is against it. I always thought that most girls wanted to suggest it first so I guess I should have said "maybe let her ask" or something like that. But yeah, I guess the guy has got nothing to lose if he asks outright. I think some guys think they can sway their girl's opinion about anal sex, which is what I have a problem with.

My earlier statement was a pretty flippant one, so apologies for that.

No problem your comment just came across prud ish/sexually repressed. If he is in a relationship with her. He should be able to communicate with her and find out her opinion on anal sex. It seems like he doesn't even know that yet so there is nothing to sway. Just be adult about it and ask her up front. Also if she isn't into anal keep going and see what else she might be into that isn't just vanilla sex.