You’re obviously wise enough to realise that what you see in porn often fails to square with reality, or you wouldn’t have asked the question in the first place. Having said that, yes, some women do really enjoy anal sex as it gives them the feeling of being very “full”. Other women may enjoy anal play but not necessarily be keen on having full anal sex. And some women are not keen at all. You won’t know until you ask.
It mightn’t be a bad idea to approach the topic after sex as opposed to beforehand – less pressure. When suggesting something new it’s often better to broach the topic like: “Have you ever wondered what…” instead of a “I want to…”
If your girlfriend isn’t totally against the idea but is worried about pain, you could try suggesting butt plugs to begin with. You should also get one for yourself. A man’s prostate gland can be stimulated through the anal wall and most guys find this really pleasurable.
Anal sex should not be painful. If it is, you’re going too fast or not using enough lube. Taking your time and using plenty of lube are the two golden rules. Go slowly. And by slowly I mean really slowly. It takes time to for the anus muscles to adjust to the new sensation.
Get a lubricant designed for specifically for anal play. Use plenty. Then use a bit more. The anus doesn’t self-lubricate. Most sex shops have them, if not, look online. Remember you need a water-based lube, as oil-based lubes are not safe to use with condoms.
Use a condom. Anal sex carries a greater risk of spreading STIs as the skin of the anus is thinner than the vagina.
Use a fresh condom if you move from the anus to the vagina. If you’re in a monogamous relationship and both have been tested for STIs and are no longer using condoms, you need to wash your penis thoroughly before switching between anal and vaginal sex. Bacteria from the anus can easily
give your girlfriend an infection such as cystitis (bladder infection).
Some people are concerned that anything anal can be a bit dirty. Obviously it can be… All sex shops sell douches specifically designed to clean the area.