There's been a lot of advice over the years on this area and despite its being over a weekend and off the road I don't believe its possible to avoid one of you losing out unless you SORN as RT says and reverse it soon after..
However be careful. We did that for a sale within the family as we waited to sell the old car before taxing and insuring the new one for which we posted off the SORN. As luck would have it we sold the old one right away while the SORN was in the post.
I called the DVLA to see how to tax and unSORN the new car immediately.. However the SORN'd car was then in limbo as the DVLA hadn't received the form in the post but couldn't promise to intercept it or cancel it, or put a marker on the file.
Their advice was it was probably OK to tax the new car but to check online daily to ensure the SORN wasn't enacted. And then call them if it was!
As it happened it was OK but it was a faff to keep checking and with ANPR cameras sniffing about I'm not sure if we were at risk of being pulled over.
So if it were me in your situation I'd just suck up the double payment by effecting the sale/tax/insurance on the relevant day and either you lose out by paying for June or the buyer does by paying from May. Nuts but there you are.
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