Ok so I just started maybe a couple months or so ago with anal play. Thinking about this just about made me not wanna do that anymore. 
Never mind I take that back. It feels to good 
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I haven’t had issues with plugs so far. All have flared bases and don’t tend to move much when inserted. One thing that does help put my mind at ease is tying a ribbon around the base so it acts like a retrieval cord just it case. I tend to only do this with new plugs and once I’m familiar with them and trust they won’t go traveling, I stop adding a ribbon.
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I tried that when I started playing now needing more girth the bases are wider and sometimes uncomfortable for prolonged wear I find. Once you find a comfortable compromise stick with it in my opinion
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I’m starting to find that too. As I’m moving to bigger plugs they also need to have a bigger base and although the plug may be comfortable internally the base starts to chafe after a while. A T bar base is OK but glass plugs, which I prefer, don’t have T bar bases.
Me and the OH @Steffi.O have yet to encounter this, but when I told her about it, she was kinda shocked and she is now abit hesitant to use our metal jewel plug.
Might be a case of no long time wear and regular checks 
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Not wanting to be “that guy” but maybe they have very loose bu… Orifices lol.
I agree with what people advise, flared base or T base
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Don’t think it is necessarily an issue of the size of base (a large flared base would be pretty uncomfortable to walk around with I would have thought) but the flexibility of the material.
The prostate massagers all seem to be made of a hard material and there is no way the base is going to get sucked in. The jewelled metal plugs all have bases relatively small compared to the widest part of the toy so you are always going to need to be careful if you are being active. As for the softer material plugs whatever the shape or size of the toy you will need to be careful.
The larger the girth of the toy then the more you have stretched the entrance so more care needs to be taken (in my opinion).
A fairly large (length wise) sex toy which is designed for insertion that doesn’t have a flared base should be fairly easy for the body to eject in a natural way if it goes a bit deep (anally).
For me, the issue with the jewelled metal plugs is the base which can cause discomfort if worn for a while.