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I'm not a fan of long necks - although they can't be too short. For us about 1-1.5" is good. What matters to me is a nice taper on the leading side.

Some anal plugs are much too abrupt for comfortable insertion - especially for beginners. We like the B-Bomb most.

I can't keep a plug in well if it does not have a long enough neck.

It depends on what you consider short and long and opinions will vary. As a general rule, the plugs with really short necks will tend to pop out.

Doc Johnson Classic Butt Plug Royal - Too short for me. It tends to pop out.

Sasha Grey Signature Series Sexy Spades Large Tantus A-bomb These are comfortable to me and stay put. I use all three on a regular basis.

Since you are a beginner, I would suggest not buying the plugs that I referenced above. I was just using them as an example.

Get an Njoy or Mood naughty.

Honestly, I think the Tantus Neo would great for a beginner. The tip makes insertion easy, the girth isn't overwhelming, the neck is fantastic, and the base is super comfortable.

I agree with Trysexual about the Mood naughty plugs, they're not too big, the neck is slim, and the base is made to sit comfortably. Plus, they're less expensive, so you can figure out what works for you without breaking the bank.

*I've worn both for upwards of 2 hours with no discomfort.

The neck on the original mood naughty is great, but it is much shorter on the mood naught 2 and 3. Just keep that in mind.

The neck is important for retention ease. Too short of a neck will leave the plug holding the anus open from the inside, which triggers your "relax" reflex. An inch or so of length is usually enough.

The other important thing to look at is the contours of the "bottom" side of the body. It's going to be opening up your anus just the same as the top, so get one that's gradual. An abrupt change in size can also be uncomfortable all the time you're using the plug, especially in a hard material.