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I rarely use backgrounds so I'm not familiar with them Any suggestions for BGs that would match Pinhead would be super appreciated! Buyable ones, that is x)

Maybe

or this: Private Outfit

Or

Another option: Private Outfit

Really like 's suggestion with the chains even if you cannot find a good backdrop.

That aside, maybe this? Outfit Not Found

Also, or seem like they could offer complimentary details to a more suiting backdrop.

thats a very smart usage of the chains :D I'll try to find a blue-ish background or foreground so they can blend in more

OH WOW!!!!! That one looks so badasss :o I'm a big fan of the Well-Hung Meat (hehehe), adds the pain/torture element I'm seeking

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here's two ideas for you~ i incorporated Lypsyl's idea of the chains in one :)