I suggest the Fun Factory Bootie. It's small, comfy, good for beginners, silicone, a good price, and won't go to waste if you don't move onto bigger things / anal sex with the hubby. You can wear this one around, during masturbation and even during sex. I love the Bootie! It's one of my very favorite toys.

Before you start with toys, try playing with a finger first! Because you can feel what's going on, it's easier to know if you're taking it slow enough. If you're worried about your/your partner's fingernails, you can always use finger cots.

Thanks EffinSara - i have done the finger thing actually. I really enjoy it, so I thought I'd move up into the world of small toys.

Victoria - thanks for that rec. I will check that out.

As long as you're not looking for a plug that will stay in, I recommend this for anal play:
link

That links to my review. It's cheap, it lays flat, it's flexible to not hurt, and it has a great flared base so you don't have to worry about it. It's slim enough to not hurt, but you'll know its there.

I have to 2nd Victoria's Bootie recommendation. I've used many different anal toys and it really is the perfect first time toy, small, uber-comfy, stays in, works very well for extended wear and is easy to keep clean.

Thanks for the posts - this is just the info I came here for! To add another question, what are your thoughts on anal beads for beginners? Is it better to try out plugs first? I've used my finger before, but it's awkward to reach and I want to try a toy but don't know what kind is better to start with.

Beads are somewhat awkward and could be irritating. I vote for something smooth and gradual as a first toy.

If you do go for beads, get one of the solid silicone "bead sticks" - safer, cleaner, easier to use.

Good choice starting off with a finger.
I'm in favor of a soft plug (silicone!) as a first toy. Small, most have a gradual taper that you can slowly relax around, and they're flexible so there isn't much risk of messing up and causing pain (provided you go slow). A second option would be a small(ish) smooth dildo or probe - but these tend to have a more abrupt end on them.

I would definitely suggest focusing on anal dildos. Anal beads seem to be more of an acquired taste and, in my opinion, don't give you the full experience or training a dildo would.

Depending on what you want and how comfortable you are you also don't have to use an anal plug first. I went straight from finger to dildo and had no problems or hiccups.

I also support what ScottA said about using a soft material(silicone or maybe even jelly if you don't plan on keeping it forever). You wont regret it!

I actually am in the same boat as holly hox and ruby miracle! I have played with myself and my ex boyfriend wanted to try anal but we never got past the head of his penis! I'm new to the community and have actually bought a few anal toys and waiting for them to arrive and be able to review them. I still consider myself a beginner because I haven't been masturbating a lot lately (health reasons affected my libido which sucked!) and have recently gotten my "modjo" back and looking to have some fun!

I've ordered a set of anal beads and a starter kit that includes a dual stimulation vibrator and an anal attachment (I've been very curious and interested in vibrating anal toys, any thoughts on those?), warming anal lube and a plug. I do have a jelly butt plug that my ex had gotten me to try to get used to anal bfore he tried but honestly, I was able to get half in at one point and hated the feel. I think it was just that it wasn't as rigid as I'd like it to have been so I feel anything above jelly would be a better alternative. I also ordered an enema kit that I saw a lot of people had been recommending for anal play so as not to have the messiness involved.

Hope this helps and I hope to hear how your adventures go and what you decide to get!

I have a few vibrators I use anally as well. They are pretty pleasant

I agree with ScottA, silicone is great for anal. I do like the other materials he mentioned, too, but the silicone is nice since it usually has a bit of give to it.