I had never tried anal before my current SO, its definitly different. One thing all the wise women on here will tell you is that it should never hurt. You risk causing damage later on down the line if it hurts.

They make dildos and plugs specifically for anal. I've got one of each. You always want to start small and use lots of lube. Start with a finger, move up to two fingers, then a plug, then a slender dildo or vibe. I don't know that a vibe is a good idea at first though b/c I would think that the feeling of "having to go" would just increase with something vibrating in there.

It can be a lot of fun, esp with double penetration (twice the fun!). My SO and I don't do it very often, but when we do I enjoy it. I think I've only cum once or twice when he's done it, but if I'm good and worked up when we start it feels really good.

If you SO will let you, try it out on him to. Its a strange feeling at first, but when your man is bent over and your doing him in the butt with a strap on from behind it definitly gives you a different perspective on doggy style. Speaking of... its been a while since Dave and I have explored that aspect of sex... I might have to pin him down tomm.