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Monday, June 8, 2020

Jackass July 2.0

Two years ago I opened this blog up to a free-for-all of kinky dares in order to see what would happen. (See pasts posts in July of 2018) While overall I would  consider that "Jackass July" mostly a success, I did sort of feel overwhelmed by it all and consequently did not do one in 2019. 

After a discussion with my "Monster-in-crime" Ana, we came up with something of a compromise. And so, I hereby lay out the challenge for "Jackass July 2.0, the 2020 edition":

Torturous teasing is a possibility that hasn't been suggested before.

As with last time, readers are welcome and encouraged to submit via comment, their suggestions for somewhat interesting, kinky, and generally challenging yet fun dares that they would like to see me execute and post. The rules are simple. Please do not waste your time suggesting anything that involves people unlikely to comply, try to keep them to me alone. Ana is away at school, so I don't have a video camera-person. Also, keep your dares limited to things that are feasible, generally legal, and somewhat safe and sane. That does not mean they can't be embarrassing, physically challenging  or even downright painful, or risky within reason. In fact a good dare might encompass most of these things. 

Could nipples be the focus this time?

The biggest departure from Jackass July 2018 will be that rather than Ana being the referee of the dares submitted, with nearly all of the dares being done, THIS TIME she will act as judge for the dares submitted. Once all are in, she will pick ONE. She will pick it based on her own preferences and her decision will be final......for those competing and for me!  (she has the option to pick a runner-up but only if something REALLY impresses her and makes her want to add it in.)

Anal invasions played a bit part in 2018. Will they again? What new twist might there be?

Frighteningly inspirational?

In 2018 I ended up with a piggy 2020 the year of the donkey tail?

Or will my tail be a different kind of danger?

Will the dare be a bit more orgasmic?

Or is it more likely that 'I'll' be the one getting fucked?

The winning dare(s) will then be executed by me, recorded as appropriate, and posted here along with credit to the author of it with all honors and bragging rights that go along with that. Dares will be accepted throughout June with the deadline being June 30th.  Readers can submit more than one.....but no more than three.

Let the party begin! Jump on in....because, like the boy here, it's my ass on the line after all!

If anyone wants to 'play' but has questions, just ask. If my answer seems cowardly, just say so and I will let Ana be the judge on whether it is. Also, as judge, this time Ana herself will NOT submit any dares of her own. And while I think it's unlikely, if all the dares submitted fail to impress my Monster, Jackass July will end without any dare being executed. Good luck. Be creative. Be mischievous. We are both looking to be pleasantly challenged!


  1. Coming up with a dare for you is similar to the struggle my kids have with buying me Christmas presents. In my case, it's "what do you get for the man who has everything?" In yours, it is "What do you dare the guy who's done everything?"

    Now, *I'm* the one who should really do this on my blog, given that it often seems like every commenter has explored more than I have.

    1. LOL, that's funny. Both observations are funny.

      Maybe I should post a list of possibilities that haven't been covered here so far?

    2. While it might get things going, I think that's too close to daring yourself. Though, how about this spin? As open and daring as you are, are there things that make you nervous or give you pause, such that the dare would actually challenge you and make you gulp a little before you give it a try?

  2. Gosh, i'm drawing a total blank. first, as Dan says, you've done way more than i could have ever dreamed up. second, with the lock down and lack of play (and any kinky talk at all) my imagination has all but run dry.

    I did like the donkey tail idea. perhaps something domestic. like cooking a special meal WHILE wearing the tail with nothing but an apron on (cooking can be dangerous to bare skin after all!). And then serving your meal to Rosa while you wait in attendance (with tail still in) and without being allowed to speak in words. You could make donkey sounds to make your queries known to her while doing so.

    1. Thanks for stopping by and leaving the first and so far ONLY suggestion. It's kind of cute. Let's see what else gets suggested and what Ana decides.

  3. Well, my Birthday present ( was quite impressive, and I enjoyed the clean up post ( as well.

    My creative juices have dried up a b it, but if I can think of something fun and original, I'll let you know.

    1. Thanks, dear. The unfortunate reality is that only one person has contributed so far and given the lack of traffic here lately, it might be unlikely that there are any more. If so, I might just discuss with Ana the possibility of cancelling the event due to lack of interest.