While I think that something happened in Painted Black given Tedd's lack of black teeshirt underneath after the pounce. Although it is probably not full sex (although this is the closest they've gotten so far) probably got pretty intense and involved a lot of close contact on the floor with nudity involved. Grace would want to go farther then they went before and given that there was probably some minimally clothed making out off screen during the Sexy Shirt Swap and her lack of qualms about nudity.
Outside of that Tedd wouldn't try to sleep with her unless he felt that she was ready given his with morals status as his lack of skill at hiding it. He'd probably have a major "What have I done!?" moment if he ended up feeling that he pressed Grace into sex.
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