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Might need to stop every so often to check on how she's taking to it. Is she going to be able to wrap her hands around you AND that backrest? The more I keep thinking about "where's she going to put her hands", the more I think of losing the backrest and make her put her hands around you. That way there's no worry about side pressure on the milk crate, and you could have her push against you for back support.
Any way you decide to do it, I'm sure you will more and likely be trying several different arrangements.
Any way you decide to do it, I'm sure you will more and likely be trying several different arrangements.