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Assuming the pants in question are within 10 feet of the caster (20 if a sorcerer is using the distance metamagic on Prestidigitation for some reason) and the caster is targeting only a cubic foot region strategically positioned to embarrass the victim.

Is it possible to target something worn/held by an unwilling creature with Prestidigitation?

If so then does this provoke a saving throw/attack roll or does it happen automatically?

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Is it possible to target something worn/held by an unwilling creature with Prestidigitation?

D&D 5e rules say what they mean and mean what they say.

You instantaneously clean or soil an object no larger than 1 cubic foot.

Doesn't put any limits or restrictions on the spell other than its volume.

If so then does this proc a saving throw/attack roll or does it happen automatically?

D&D 5e rules say what they mean and mean what they say.

There is no mention of a saving throw so there isn't one.

As an aside, well done on an imaginative use of the spell - have advantage and some inspiration.

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  • \$\begingroup\$ Comments are not for extended discussion; this conversation has been moved to chat. \$\endgroup\$ – SevenSidedDie Jun 23 '16 at 6:58
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No, and even if you could it wouldn't be as cool as you might think.

Pants are more than a cubic foot. So . . . no. The spell description is clear: it is not the volume of soiling that is limited to 1 cu.ft, but the object being soiled.

But even if the spell were cast on the pants of a pixie, notice that the spell does not provide for the caster to specify the form of the soiling - either the shape of the stain or the type of soil. It is not fecal material, it is merely generic "soil". And it is not concentrated on any specific part of the object. The effects of the spell (if allowed at all) is that the man has dirty pants. In a royal audience, this might be a big deal. In a tavern right after quitting time at the mine, it might not be noticed at all.

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  • \$\begingroup\$ I changed 'area of soiling' to 'volume of soiling', but upon reflection, I'm not sure whether you meant the concept of 'area of effect', rather than physical dimensions. \$\endgroup\$ – user117529 Apr 16 '16 at 21:12
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In addition to pokep's point about "soil" not referring to feces it would be completely impossible anyway in almost all cases--you would not have a line of effect to the target. The underwear will be under their pants and unreachable. (You could, however, put a brown color on the panties of a woman wearing a short skirt indiscreetly.)

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  • \$\begingroup\$ Assuming you were somehow able to "indiscreetly" get a line of sight to them... \$\endgroup\$ – Dan Henderson Apr 18 '16 at 20:51
  • \$\begingroup\$ @DanHenderson That's why I specified wearing it indiscreetly--in other words, offering you a view so you have line of effect. \$\endgroup\$ – Loren Pechtel Apr 19 '16 at 0:54
  • \$\begingroup\$ Oh, right... Whoops! indiscretely. Derp. 😛 \$\endgroup\$ – Dan Henderson Apr 19 '16 at 2:39

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