So at the moment, we are at the stage of just trying with fingers but I think it's more psychological than anything.
That's a good start. Usually how I get my girlfriends to open up is during sex she may get hornier, so you can start by gently applying pressure against her hole with your thumb until it sort of just slips in. It really helps if she can cum doggy style, cause when she's having an orgasm, she'll really become more receptable to anal. Once the thumb gets in, I just hold it there until the first knuckle for a while. After a while, she'll forget it's even there and it'll feel like her hole has grown around your thumb. Then do the same with your dick, just apply gentle pressure against it until it slips in. Now what happens after that will seriously depend on your gf. Some of my girlfriends can take it deep, and some push me out of bed after shrieking in pain.
Hamsupgwai:
For WGs that you've listed, do they charge above what is on the price for anal, or is it assumed to be on the menu for the whole package deal?
My experience with WGs (random walk-ups to non 141 girls) is that you can just point at her butthole and ask her "if you do this", since I didn't know the euphemisms for anal in Chinsese at the time like I do now.
During sex, I politely inquired and she told me that she can, but I'll have to add money. Being that she took a while to make up a number in her head, I'm assuming it's not a regular thing she does. Added $300 for it. We went at it for a while, tried both doggy and mish, and she finally said no, she couldn't take it anymore and if there's something else we could do, but still ended up paying the extra $300.
My advice, go after the ones that are experienced and prepared for anal, else you'll just lose your money.
I would love to find a WG that actually likes anal. I've read some girls actually do, though I've never met one in my life, caucasian or not. Maybe my best luck will be with a Thai girl or Russian girl? Any advice on this one guys?