Diminutive or smaller creature to hide in pocket [3.5]

[InterstellarPro]

One of my players wants to use his toad familiar to act as a spy. He wants to slip the toad into an enemy's pocket without the enemy noticing. Will this be a Hide check for the toad, a sleight of hand check for him, a sleight of hand check for his toad, or some combination thereof?

What if he wants to toad to hop in the enemy pocket of its own volition? That obviously would not be the wizard's sleight of hand check. So, would it be the toad's hide check, sleight of hand check, or both? (This is different because in this case, he is not physically putting the toad in the enemy's pocket).

[Kayblis]

I believe there isn't a RAW answer to this question. Therefore, this is my opinion:
As hiding a living being inside a pocket is hard, I'd call for a Hide check at -10 or -15, depending on size. Sliding the frog in there would be a Sleight of Hand check for the master, just like the usual skill, but the frog jumping there without being noticed... I'd treat it as a Move Silently on top of the penalized Hide check above. There are many ways to rule this, maybe using Tumble to avoid being noticed, but it depends on what you think would fit.

[InterstellarPro]

I believe there isn't a RAW answer to this question. Therefore, this is my opinion:
As hiding a living being inside a pocket is hard, I'd call for a Hide check at -10 or -15, depending on size. Sliding the frog in there would be a Sleight of Hand check for the master, just like the usual skill, but the frog jumping there without being noticed... I'd treat it as a Move Silently on top of the penalized Hide check above. There are many ways to rule this, maybe using Tumble to avoid being noticed, but it depends on what you think would fit.

I appreciate the advice, but I am not sure I understand how you came to that decision. Specifically, why would it be difficult to hide a living being inside a pocket?

D&D is not typically set during an era of skinny jeans. In most medieval settings, clothing tended to be looser-fitting. A mage would likely have layers of robes, and any pockets would be unlikely to come anywhere near his skin. An average toad weighs less than an ounce, so it is very unlikely that someone would notice its weight. So, I would think the clothing type of the target would be a bigger modifier than the size of the creature being stowed on the enemy.

[Kayblis]

I see your point. The main idea behind my thought process is that living beings aren't exactly motionless - you shift and move naturally in a tight space almost as a reflex. The Hide skill is used to hide from sight at a distance, and Move Silently to make less sound as you move. Yes, it would be hard to notice a small frog from weight alone, but remember it has to adjust itself from time to time. It's an animal, not a trained and patient rogue consciously doing his best to stay hidden all the time.

[InterstellarPro]

I see your point. The main idea behind my thought process is that living beings aren't exactly motionless - you shift and move naturally in a tight space almost as a reflex. The Hide skill is used to hide from sight at a distance, and Move Silently to make less sound as you move. Yes, it would be hard to notice a small frog from weight alone, but remember it has to adjust itself from time to time. It's an animal, not a trained and patient rogue consciously doing his best to stay hidden all the time.

Actually, the toad's intelligence is almost as high as the party rogue's. At 5th level, a toad familiar has an intelligence of 8. It is no longer a simple animal, but a magical beast. I do take your point, though. Even just the toad's breathing would be some minor movement that could be noticed over time. I'll have to consider this further. I think the initial placing of the toad would be a simple sleight of hand check if the wizard does it. I think it would be a hide/move silently if the toad does it himself (maybe modifiers based on how tight or loose the target's clothing is, ranging from +0 for baggy wizard's robes to -10 for nothing but underwear (I think we have all had a creature of some sort on our back without realizing it until someone points it out, although it is typically an insect, I can see a slightly larger creature trying to hide being able to pull it off).

[InterstellarPro]

So, here was what I came up with. This is not play-tested, and probably needs some tweaking. I am erring on the side of making it possible, but difficult.

New skill uses:

Sleight Of Hand
Check:
Plant a small item (or a creature) on a person. This has the same DC and modifiers as the check to Lift a small object from a person.

Hide and Move Silently
Check:
You may attempt to hide on the person of a creature at least three size categories larger than yourself without their knowledge. Make separate Hide and Move Silently checks opposed by Spot and Listen checks. The types of clothing worn by the target may provide circumstance modifiers to these checks. For example, it is next to impossible to hide on the person of someone who is naked, but much easier to do so when they are wearing flowing robes or baggy clothes.

Does anyone have any suggestions for other modifiers for this check? I don't want to make it impossible. It is a creative use of his familiar, and I want to reward that. But, I also want to maintain some degree of realism, so right now, I think it is too easy for the toad to succeed. Should I negate the toad's size modifier to Hide checks? That would make it fairly difficult for him to succeed (relying only on his dexterity). But, that does not make a whole lot of sense. A creature that is size category Fine should definitely have an easier time hiding on a creature without being noticed than one that is size category Diminutive, so there should be some size modifier to Hide. Maybe a flat -10 (negate most of the size bonus) for attempting something that is nearly impossible for most creatures?

[DeTess]

So, here was what I came up with. This is not play-tested, and probably needs some tweaking. I am erring on the side of making it possible, but difficult.

New skill uses:

Sleight Of Hand
Check:
Plant a small item (or a creature) on a person. This has the same DC and modifiers as the check to Lift a small object from a person.

Hide and Move Silently
Check:
You may attempt to hide on the person of a creature at least three size categories larger than yourself without their knowledge. Make separate Hide and Move Silently checks opposed by Spot and Listen checks. The types of clothing worn by the target may provide circumstance modifiers to these checks. For example, it is next to impossible to hide on the person of someone who is naked, but much easier to do so when they are wearing flowing robes or baggy clothes.

Does anyone have any suggestions for other modifiers for this check? I don't want to make it impossible. It is a creative use of his familiar, and I want to reward that. But, I also want to maintain some degree of realism, so right now, I think it is too easy for the toad to succeed. Should I negate the toad's size modifier to Hide checks? That would make it fairly difficult for him to succeed (relying only on his dexterity). But, that does not make a whole lot of sense. A creature that is size category Fine should definitely have an easier time hiding on a creature without being noticed than one that is size category Diminutive, so there should be some size modifier to Hide. Maybe a flat -10 (negate most of the size bonus) for attempting something that is nearly impossible for most creatures?

Another things you could consider is letting there be a chance of failure (somewhere around 25-75%) separately from an unpenalized hide-check. A small frog could probably go unnoticed if its slipped into an outer pocket of a jacket and sits very still, provided the owner of that pocket doesn't need to get anything out of it. This encourages either more shenanigans to keep the mark from picking stuff out of that pocket, or make this a strategy of last resort, rather than a standard trick to do any time they want to tail someone