This is probably not gonna be at all helpful, but scan the SPN Anonymous Kink Meme (http://blindfold-spn.livejournal.com/), rounds 1 & 2. I know there's at least a couple of fics I've seen there that'll scratch your itch. The reason I'm giving you such a vague response is that I've been scanning the meme off and on for about a week looking for a particular entry, so I've gone through so many I couldn't tell you where anything is specifically, lol. But 1 or 2, I'm confident about that part, haha.

Oh, you'll need to join the community to see entries.

Best of luck

That is a little helpful, actually, because I didn't think to look there. I'll go check it out, thanks! XD I hope I find some! :)

The rather adorably shy way you asked made me laugh a little, I admit. There aren't as many for bottom!Dean as there are for bottom!Sam, but these are what I've dug up:

http://blindfold-spn.livejournal.com/1037.html?thread=1317133#t1317133 - some pretty detailed hole!spanking in that one, probably the closest to your request.

http://spnkink-meme.livejournal.com/590.html?thread=124494#t124494 - more of a general bottom!Dean assplay!story, with mentions of spanking & hole!spanking in there.

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Tell ya what; if no more turns up, I will write some for you. New kinks are always fun =D

Edited 2012-05-18 09:07 pm (UTC)

It embarrasses me a little to make the request, it's kind of dirty, isn't it. o///o Oh my god! Thank you so much! :D *jumps on the fics* This has been surprisingly hard to find.

You might write some? *hugs* Ohemgee! That would be beyond awesome!

I don't have a rec for you but dude, i love coming across hole!spankings in fics. :)

As do I. :) Sadly it seems to be a rather rare kink.

I've only come across this with bottom!Sam, but anyone with less strict pairing requirements might enjoy it?
http://softbluebuddy.livejournal.com/110440.html#cutid1
Good luck!

well, I'm not much for bottom!Sam, but I'll read it anyway, because I adore this kink. Thank you! :D