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2020 DIY Christmas Challenge Results Kicking Off the Holiday Season!

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I wanted to start off the holiday cheer with lots of DIY Goodies for everyone to read!

This should be the first of MANY Holiday blog posts that will take you through until Christmas Day, and you never know .. perhaps beyond it! Right now I have a caption for everyday but one through to Christmas Day, but perhaps I'll make one more before time runs out on me, as I still have a few ideas left from last year. 

And while I received only a few submissions, they had lots of quality work attached to them, so let's get the ball rolling with the parameters of the challenge:

I haven't done a DIY Challenge in quite some time, apparently February of 2018, was the last time I offered it. Since it's Christmas of a shit-astic year, why not try to bring some cheer into the last vestiges of perhaps the worst year ever .. 2020! So here is a caption setting .. and a sentence that must be included in the caption, "We'll she'd (or she's) done it this time!"

And, I'll go first because, why not? I made my caption last, and deliberately didn't look at any other submissions because I wanted to make sure that mine wasn't influenced by someone else's, and if I did come close to another plot line .. it'd be fun to compare how we saw the picture I provided.


I really had nothing in mind when I created this caption setting, other than, at the time I thought I might use it for Nadine, who loves women in boots .. but I am pretty sure I made the setting right after Christmas .. and ended up not using it then, which is why I had it all set up already for the challenge.

So, to me, this was a blank slate, and I took advantage of that by just staring at it until I came up with something .. and since her handbag looked sort of like a clipboard, I thought "she" was canvasing the neighborhood in support of something, and the lack of mask (it's honestly the first thing I see in any picture I see now, "why aren't they wearing a mask!" made me think, "The War on Christmas" narrative that I've seen read its ugly head over the last few years.

and from there, I just started writing, and it all seemed to fall into place. I love the melting pot idea of her part of town, and needed to work with it, and why not through in some witches and pagans? My GF was Wiccan, and she LOVED the non-religious parts of Christmas, so I had to work that in. Plus, it sort of has some elements of The Christmas Carol worked in, with a redemption story of sorts.


Caitlyn Masked was the first to send me something, and it was sweet of her to actually use my caption setting, instead of making the rest of us look like mere amateurs with her graphic design work! In a way, I think it works for the best, as we can focus on her story, since the feel for the captions are now analogous. The plot is sweetly touching, while still retaining her core TG ideals. Well crafted, and I'm always happy when Caitlyn posts something new. So Merry Fucking Christmas to all her fans .. there's a new caption from her under your figurative tree!


Sally Bend, the author and captionist, also submitted something to me (submit to me, Sally!) that is much naughtier than mine by a long shot! Sally was also naughty by not putting in the sentence "We'll she'd (or she's) done it this time!" that was supposed to be in the story somewhere! I guess I'll have to spank her ass until it is a red as that sweater! That'll learn her .. maybe! Either way, you don't usually see many Christmas captions that involve cuckolding, and then sharing the hunky man in a Santa suit with her now female hubby. I'm sure that guy's name isn't Tiny Tim by any stretch!

So for now, that is what I've received by Sunday morning, which is when I wrote this blog post out. If there any more that arrive down my chimney before Monday morning, I'll add them in here, since I believe in making this holiday season special for everyone that drops by my humble online abode.

Please comment down below on the captions, and discuss what you liked about each one. All of us took some time to create something that will hopefully put a smile on your face. It'd be great if you could acknowledge their time and effort!


Well, she is standing at a front door, but you just know she wants Santa in her back door!

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