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Should work just fine - Bootie seems to stay in pretty well.

The biggest problem with wearing any plug during vag. sex (probably the only problem) is the plug coming out during orgasm, but that isn't too much of a problem really. If you're worried just put down a towel.

It doesn't slip out if this is what your asking. The hooked end prevents it from slipping out during sex or even orgasm.

I was just wondering if it was even doable. Some people have mentioned the base being very long and obstructing the entrance to the vagina.

Well, I've tried it and it popped out like crazy. Maybe because of too much lube, and I was very relaxed. I was also on top rather than in missionary. I didn't find that it got in the way of my vagina, though.

Anal toys popping out is very much a personal thing - some people orgasm so strongly that there is almost nothing that will stay in.

If you're having problems with the base obstructing the vagina there's nothing wrong with taking sharp scissors or a very sharp knife and trimming off a bit. I find that fingernail clippers help with the "final" rounding of the new edges.