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Obviously, one should never, ever use an oil-based lubricant with condoms, since any oil degrades latex almost instantly.
However, I have, in the past, occasionally used olive oil as a lube for handjobs and for anal-- in situations where I am with a partner with whom no condom is necessary-- and have never had a problem with it: works well, and in the case of HJs, makes for an easy transition to BJs. When I've used it as lube for anal, I've always suggested the girl wash thoroughly afterward, and use the shower spray to spritz a good spray up the butt, which generally gets most of that oil (and jizz) out of there pretty completely and quickly.
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Dull sublunary lovers love,
Whose soul is sense, cannot admit
Absence, because it doth remove
That thing which elemented it.
(From "A Valediction: Forbidding Mourning" by John Donne)
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