Waxenboy, herpes is a virus and cannot be "caught" by going from ass to pussy.
If neither partner has herpes, then neither partner will get herpes just from engaging in sexual behaviour. However, as faeces contain a number of nasties, you shouldnt go from ass to pussy or ass to mouth. The easiest way I have found to bypass this issue is to wear a condom for anal sex and then remove it if you wish to move to the vagina or the mouth.
Gopherhkyfan, anal sex can be a really pleasurable experience, but you need to make sure your partner is relaxed. It helps to lube up a finger or a smaller vibrator/dildo and use that first in the ass to get them use to the sensation. I personally can only orgasm sexually through anal sex. Its amazing if you do it right.
And Gr8stuff, most toys that are specifically made for ass play have a flared base to ensure they dont get 'lost' along the way... But yes caution is advised! Theres something you dont want to go to your doctor for!